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Pentatonic

Author: 

  • Pentatonic

Organizational: 

  • Author Page

Audience Rating: 

  • General Audience (pg)
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Pentatonic

A Glimpse of Panties

Author: 

  • New Author
  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Caught with Consequences

TG Elements: 

  • Panties / Girdles

Other Keywords: 

  • Jukebox

Permission: 

  • Posted by author(s)

A Glimpse of Panties.

By Pentatonic

It was Saturday, about mid-afternoon, when Joe called. “Dave, I hate to bother you, but the jukebox sounds like shit, and I’m expecting a good crowd this evening. Do you think that you could look at it?”

Joe was a good friend of mine who ran a bar. When he decided to buy the place he was a little short of cash, and I bought into and owned a part of it. Joe had an old AMI jukebox, that I had found and rebuilt for him. Since it was a 1959 model J, there just weren’t a lot of people around who knew how to work on it.

“Tell me a little bit about the problem,” I said, “is the sound distorted?”

“Yeah, and it isn’t as loud as it should be. Could you come over and look at it today?”

“Ok, but no guarantees that I can fix it before tonight. I have plans for tonight, and I need some time to get ready,” I added. I didn’t say what my plans were or why I needed time to get ready. I suspected that Joe knew that I was a transvestite, and that tonight was a meeting of my local TV/TG club.

When Joe called, I had already enjoyed a long bubble bath, and had put on a gaff, panties, bra and camisole. If I were going to go the Joe’s place, it didn’t make a lot of sense to change my underwear, so I just put on a pair of jeans and a loose sweat shirt, and grabbed my tools and some parts which I might need. I decided to take a spare amplifier with me, in addition to my other stuff, “just in case.”

When I got to Joe’s place, I listened to the ailing jukebox, and decided to start with replacing the stylus. “Joe, when’s the last time you replaced the stylus?” I asked.

“Don’t know. You should know, since you did it.” he replied.

“Okay, I’m going to start with the stylus, since that is the easiest,” I explained, “you need a new one anyway. It’ll only cost you $15. Replacing a stylus is relatively easy, and I was done in about five minutes.

I selected a record. It sounded just a bad as before. “Well, the easy fix didn’t do it,” I said with a sigh. “Now we’ll have to try something else.”

“Help me get the jukebox out from the wall,” I asked Joe, “I’ve got to get to the amplifier compartment, which is on the back at the bottom of this sucker.” We moved the jukebox out about six feet, and I noted with dismay all of the garbage that was on the floor where the jukebox had been. “Don’t you ever move the box and clean under it?”

“Every once and a while,” Joe said defensively.

“Could you get a broom and do it now? I may have to lay on my stomach to access the amplifier, and I don’t want to wallow in this garbage.”

When the area was cleaner, I moved my toolbox and the spare amplifier behind the jukebox. “I don’t want to have to get up and down, so I’m going to need your help handing stuff to me.” I said.

I decided to look at the amp with the jukebox on, to see if all the tubes were on. When I squatted down, my jeans dropped in the back and my shirt rose, exposing the waistband of my panties.

“Interesting underwear,” Joe commented.

“Well, when you called, I was in the middle of getting ready for tonight, so I just threw on the jeans and shirt and came here,” I explained, “I didn’t want to have to start all over.”

“I think that I am just going to replace the amp, and I’ll take your amp home and fix it. I’ll be back later and put your amp back in and take my amp back home,” I explained. I replaced the amp, turned the jukebox back on, and it worked.

“You’re good, even if you dress funny,” Joe said. I just scowled in return. “Just joking,” Joe said with a smile, “let me buy you a beer.”

While sitting at the bar, I explained that I was a member of a transvestite and transgendered group that met every other week.

“How come you never asked to meet here?” Joe enquired. “You know that we have a party room in back that might meet your needs. I can even have some food brought in.”

“I wasn’t sure how you would feel about us being here,” I responded.

“I feel great when I hear the cash register ringing,” he said with a big smile.

I talked it over with others in the group, and we decided to have a 50's party at Joe’s bar. I had fixed Joe’s amp, and I decided to swap it out on the night of the party. So, there I was, in a circle skirt, blouse and heels, laying on a blanket this time, behind the jukebox. I smiled at the comments made by patrons of the bar, about a cute chick fixing the jukebox.

After that, Joe said that I would be welcome at any time, dressed or not. I took him up on that, and every time I went to the bar, I went dressed, sometimes joined by other members of our group. The group started meeting at the bar, and it became known as a TV/TG friendly place, much to Joe’s pleasure in the increased business, all resulting from a glimpse of a pair of panties.

Gene or Jean?

Author: 

  • Pentatonic

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

Gene or Jean?


By Pentatonic

TG Themes: 

  • School or College Life
  • Sweet / Sentimental

TG Elements: 

  • Corsets
  • Fancy Dress / Prom / Evening Gown
  • Performer/Entertainer

Gene or Jean? - Part 1.

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Sweet / Sentimental
  • Voluntary

Permission: 

  • Posted by author(s)

Gene or Jean? - Part I.
By Pentatonic

Chapter 1 - It All Started in the Bathroom.

My name is Eugene, ‘Gene’ for short. I have three sisters who, when it all started, were 19 and 17, and 13. I was 15. I am the only boy. Mom and Dad must have had some kind of routine, since all of our birthdays are in August. I always view the Thanksgiving turkey with some suspicion - you do the math; how many months from Thanksgiving to August.

There are never enough bathrooms or hot water in a house occupied by three teenaged girls. Accordingly, I plan my bathroom visits with care around their expected bathroom use. Sometimes it works and sometimes it doesn’t.

This time it didn’t. I was getting ready for bed and was in the shower when I heard the bathroom door open. I should have locked it, I thought. “Hey, I’m in the shower,” I shouted.

“That’s Okay,” my oldest sister Nancy, responded. “I won’t take too long.” In my family “not too long” is not only inexact but also relative,

“Yeah, but I’m through with my shower, and I want to get out and go to bed,” I said.

“Who’s stopping you?” was her rejoinder. “Just remember I’ve seen you naked lots of times.”

“But that was many years ago,” I protested.

“So?

“So get out.” I commanded. It didn’t work. I thought, what the heck, turned off the water, pulled back the shower curtain, and climbed out, stark naked and dripping wet. I quickly grabbed a towel, but not fast enough to prevent Nancy from seeing me in all of my glory.

She was leaning over the sink, doing something with her eyebrows. However, she was doing that while wearing my robe.

“My robe,” I sputtered. Nancy ignored me. “I need it,” I said. “How would you like it if I used your robe?”

“You’re welcome to it any time you want, it’s hanging on my closet door with my nightgown,” she said with a snicker. “In fact, maybe you should. You’d look cute in it.” Her robe was a filmy thing that was sort of see through, that she wore over her nightgown.

‘If that’s the way you want it, so be it.’ I thought, and holding my towel I headed for the bathroom door.

“Your towel should be tucked in around your armpits,” she said, “to cover your boobs.”

“But I don’t have any boobs,” I asserted.

My sister just chuckled. “But don’t you wish you did?”

On my way to my room, I passed Nancy’s bedroom. The door was open, and hanging from her closet door was the aforesaid robe and the nightgown that goes with it. A wicked impulse, driven from her comments about her robe, drove me into her room. I picked up her robe and nightgown. The felt so smooth and soft. My wicked impulse also drove me to put both on. Wow, what a reaction. I now knew why my sisters liked these kind of robes and nightgowns. Suitably, or maybe unsuitably, attired, I went back into the bathroom. My sister was still there.

I really had to use the toilet. “I’ve got to pee,” I announced.

“No one’s stopping you,” she answered. So I stood in front of the toilet, and started to pull up the hem of the nightgown. “No!” she loudly asserted, “If you’re going to wear my nightgown, you have to sit while you pee.”

So I sat down on the toilet,

“You know, you look really cute in my nightgown and peignoir,” Nancy exclaimed, “You’re welcome to wear the nightgown to bed. Just don’t get any stains on it.”

I just gave her a dirty look. As chance would have it, my other sisters, Emma and Gloria, were passing the bathroom at that time and heard the exchange between Nancy and me. Uninvited, they entered the bathroom. It was a tight fit and the door could not be closed.

“My, oh my,” Emma exclaimed, “doesn’t that look nice!”

There wasn’t enough room for me to stand, so I stayed sitting on the toilet with the nightgown draped around me. “He’s going to wear the nightgown to bed tonight,” Nancy said, “so I’ll just keep his robe.”

“Wait just a blinking minute,” I complained, “I’m not wearing this to bed, and I want my robe back. Anyway, I have my pajamas in my room, so you can have this stupid nightgown and robe back in a minute.”

“Gloria,” Nancy said, “you know what to do,”

Gloria chuckled and quickly exited the bathroom. I shortly found out that she had taken and hidden all of my pajamas. When this was disclosed, Emma said with a smirk on her face, “Well, Gene, I guess that you don’t have a choice now, Enjoy your night in a nightgown,” and with this parting shot all of my sisters exited the bathroom, chuckling. I was so flustered that I didn’t contemplate any alternatives to my pajamas.

With the bathroom finally all to myself, I turned to look in the mirror. The nightgown had narrow lace shoulder straps, with lace trim at the neckline and hem. The rest of it was smooth satin like material. It actually didn’t look too bad, except for my lack of boobs. I then went back to my room and climbed into bed.

Chapter 2 - The Morning After.

The next day was a Saturday, so no one had to get up early. My parents were out of town for the weekend, and had put Nancy in charge of the household, which I thought was like having Dracula guarding the blood bank. When I got out of bed, I could feel the hem of the nightgown swish around my calves, which was not a bad feeling. Not having my own robe, I put on Nancy’s peignoir.

When I went downstairs, all of my sisters were in the kitchen. Nancy was fixing breakfast, still wearing my robe. “I want my robe back, NOW!” I demanded.

Nancy chuckled, “But I need it.” she said.

I turned to Gloria. “Where are my pajamas?”

She chuckled. “Somewhere.” she said.

I was really aggravated. “I’m going upstairs to get dressed,” I declared.

“If you do, you’re not getting your robe or pajamas back,” Emma declared.

Faced with the evil cabal of my sisters, I plopped down in a chair at the table. My action provoked a response from Emma, “That’s not how a lady sits down in a chair. First, you smooth out the back of your nightgown under you and then sit gently on the front of the chair with your back straight.”

“But I’m not a lady,” I complained.

“But with a little help you could look like one,” Emma responded. Her comment met with a murmur of approval from my other sisters.

Suddenly there was a flash of light. It was Gloria with a camera. “This will look great on the bulletin board at school,” she commented.

Emma stood behind me and began to fiddle with my hair. I have honey blond hair that comes down to my shoulders. “Maybe a french twist,” she said.

Gloria left the room and returned with a comb and hair brush, which Emma used on my hair. “You really should use a conditioner,” Emma commented, “it would make your hair more attractive.”

“I don’t want attractive hair,” I complained. At this time, I vowed to myself to get a haircut today.

“Sit still,” Emma commanded, “or those photos will be emailed to all of your friends, including Sandy,” Sandy was a girl I really liked.

Faced with unfavorable consequences, I sat still and let Emma do what she would with my hair. After a few minutes, she handed me a mirror, and said, “It’s a french twist. How do you like it”

“I don’t,” I responded.

“But it looks so cute,” Gloria said.

I had enough. “When Mom and Dad come home, they’re going to hear about this,” I threatened .

“And if we tell them that we caught you wearing Nancy’s nightgown and peignoir?” Emma responded.

“You wouldn’t lie to them, would you?” I rejoined.

“Well, we caught you, in a sense, and you are wearing Nancy’s nightgown and Peignoir, so it wouldn’t be a total lie, just a little bending of the truth,” Emma argued.

“Okay, you’ve had your fun,” I announced, “now let me get dressed.”

“No, we’re not finished yet,” Emma said, and with that she put a box of makeup on the table.

When I saw it and recognized what it was and it’s intended use, I shouted, “No way!”

The camera flashed again. I could see blackmail in the works. Emma told me to turn my head, and began to apply some mascara and eye shadow. Then she did something with an eyebrow pencil and crowned it all by applying some lip color. Another flash from the camera. Emma handed me the mirror to let me see the finished product.

I had to admit to myself, that I didn’t look bad. “Okay, now you’ve had your fun, I want to take off this stupid nightgown,” I announced.

“Okay,” Nancy said, “but on our terms, not yours. Let’s go up to my room.”

When we were all in her room, Nancy handed me a pair of pink panties with lace trim and a little rose in the front. “Put these on, and you can take off the nightgown,” she said. So I put on the panties and took off the nightgown. Emma, who was behind me, put a bra around my chest and fastened it. She rolled up some pantyhose which she put in the cups of the bra. This was followed with a half slip, a short denim skirt, and a sleeveless blouse. Everything more or less fit, because Nancy and I are about the same size. Nancy then produced a pair of shoes which almost fit.

“Don’t even think about changing clothes,” Emma said while making a menacing gesture with the camera, “Go downstairs and wait in the living room.” With that, we went downstairs

One by one my sisters left to get dressed. When we all reassembled in the living room, I noted that they were all wearing jeans. “How come I’m the only one wearing a skirt?” I questioned.

“To let you show off your legs,” was the response, “and you do have good looking legs.”

“How long am I going to have to wear these stupid clothes,” I complained.

“As long as we want you to,” Emma responded.

“With you three, that could be all day,” I complained.

“All day? Now that’s a great idea, Gene,” Nancy said, “thank you for the suggestion.”

“NO,” I moaned, but by now I was getting used to the skirt and blouse. In fact, I liked the way they felt, not that I would ever admit it to the evil cabal.

Chapter 3 - Girl lessons.

My sisters then decided that I had to learn how to walk and act like a girl, a process which dragged into the afternoon, by which time I was actually beginning to like wearing a skirt. However I lived with a fear that someone would drop by and see me like this. Then came something worse.

“Maybe we should take Jean to the mall, so she doesn’t have to borrow my clothes,” suggested Nancy.

“You know, you don’t have to pick out a girl name, Emma volunteered, “just remember, when we call you Jean, it’s spelled J E A N.”

I wanted to put a stop to all of this. “I don’t think that Dad will like this,” I announced.

“I don’t know,” said Nancy, “he might think you’re kinda cute.”

“Jean IS cute,” responded Emma, “she looks a lot like you, Nancy, and you are definitely cute.”

“Well, Mom won’t like it,” I said.

“I don’t think so,” Nancy commented, “Don’t you remember all the times Mom dressed you like a girl for Halloween? I think she’d like to see you as a girl.”

So I remained dressed as a girl until I remembered that Nancy had a date that evening, and he should be arriving soon. “Look, give me a break,” I said, “Nancy’s date will be here soon, and I don’t want him to see me like this,” and I gave the skirt a little flip.

My sisters finally relented, and I went up to my room. With nothing better to do, I turned on my computer and played games until it was time to go to bed. ‘Oops,’ I thought, ‘I don’t have anything to wear to bed except for that stupid nightgown.’ I suppose that I could have used my ingenuity and found a sweat suit to use as pajamas, but I actually looked forward to the way the nightgown felt, so I put it on. While so attired, I thought that I might like a glass of milk and some cookies as a bedtime snack, so I put on the peignoir and went downstairs.

Emma and Gloria seemed to have the same idea, so we shared a plate of cookies and drank some milk. “You know, you really do look cute,” Emma said. I just grunted a reply. “Before you go to bed, you should remove your makeup and let your hair down.” I had forgotten that I was still wearing makeup and that my hair was still in a french twist.

“How do I get this stuff off?” I asked.

“Let me show you,” responded Emma, and she did.

When I woke up the next morning, I noticed that my robe was hanging in my closet, and my pajamas were neatly placed on top of my dresser. I have to admit that it was with a bit of reluctance that I took off the nightgown. I had liked sleeping in it. However, I took it off, grabbed my robe and headed to the bathroom for a shower and shave. Once dressed, I headed downstairs.

It was like yesterday never happened, None of my sisters even hinted at what had happened, although I did note a bit of a smirk on Emma’s face. Today was Sunday, and that meant going to Church. A main motivation for me was that Sandy might be there.

Chapter 4 - A ‘Girl’ Day.

A few weeks later the parents were again going to be away for the weekend. That Friday night, as I was getting undressed for bed, I noticed that the nightgown and peignoir were laid out on my bed. I couldn’t resist putting them on, and I then went downstairs for a bed time snack.

“You win,” Nancy said to Emma.

“Won what?” I asked.

“Emma bet that you would wear the nightgown and peignoir, and I bet that you wouldn’t,” Nancy replied.

“You like the way they feel, don’t you?” suggested Emma.

“Yeah, I do,” I admitted.

* * *

The next morning I went downstairs for breakfast, still wearing the nightgown and peignoir. All of my sisters were there, with sneaky smiles on their faces. It was then I noticed that there was a box of makeup, combs and a hairbrush on the table. “How about a girl day, Jean?” Emma asked.

“No, I don’t think so,” I replied.

“Then how come you’re wearing a nightgown and peignoir?” asked Gloria.

“I donno,” I answered. I didn’t want to admit that I liked wearing them.

My sisters wouldn’t let it drop, and I finally outwardly relented to another ‘girl’ day, but at the same time secretly enjoying it.

“First order of business is Jean’s body hair. It has to go,” announced Nancy. So I was given a container of hair remover, and told to follow the instructions. I was also given some shampoo and some conditioner, both of which had a perfume smell. When I stepped out of the shower, Nancy was waiting for me with a pair of pink panties with lace trim and a pink terry cloth robe. Emma handed me a towel.

“Pat yourself dry, don’t rub.”

I held the towel in front of me. “How about some privacy?” I asked.

“Girls aren’t modest in front of other girls, was Emma’s response, so I did as I was told.

As I was putting on the panties, Nancy suggested that I tuck a certain part of my anatomy back. After this, I was standing wearing the robe and with a towel wrapped around my wet hair.

“Slippers,” Gloria announced, “she needs a pair of slippers.”

“I have just the pair,” Emma announced and went to her room.. She returned with a pair of slippers decorated with some kind of feathers, and with a bit of a high heel. Naturally, they were pink. My sisters had picked out some clothes for me, which included a denim skirt the hem of which was halfway up my thighs, a long sleeved cotton blouse with ruffles in the front, tan pantyhose, a pink bra, and Nancy’s shoes.

“The ruffles help hide your lack of boobs,” Emma said helpfully, and she then began stuffing the bra.

While this was going on, Nancy was blow drying my hair and brushing it out. After Emma had finished fussing with my bra, she started applying makeup to my face. “Just a little mascara, lip gloss, and some work with the eyebrow pencil,” she declared.

At last I was allowed to look in a mirror. Although I would never admit it, I liked the way I looked. More importantly, I liked the way I felt. I was beginning to enjoy this, and I smiled at my image in the mirror.

Gloria caught this. “She must like it,” she crowed, “I saw her smile.”

The heels took a bit of getting used to, but I made my way safely to the kitchen.

“Okay, sis, You ready to do some shopping?” Nancy asked. I just nodded my head.

Emma found a jacket for me to wear, and my sisters and I piled into Nancy’s car.

I enjoyed the shopping trip, the attention which I received from my sisters made me feel pampered. At the end, I acquired two skirts, three blouses, two tops, a pair of skinny jeans, a belt, three pantyhose, two panties and a bra.

“There’s a special at one of the cosmetics counters,” Nancy announced, “let’s get her some of her own makeup.” The sales lady at the cosmetics counter was most helpful and I acquired a bag of cosmetics along with some helpful hints on applying it. The last stop was at a discount shoe store, where I acquired a pair of black flats, a pair of low heels in shiny black, and a pair of casual shoes.

Chapter 5 - Caught.

When we arrived home, we saw my parents’ car in the driveway. “Okay,” I said with some self-satisfaction, “I’ll let you explain what is going on to our parents.” I could see Mother looking at us through a window. She met us at the door.

“Is that you, Eugene?” she queried. I just gave her a weak smile. “Nancy, Emma, Gloria, suppose you tell me what’s going on here.”

“Isn’t she pretty?” Emma asked.

“She is,” Mother answered, “but that doesn’t answer my question. What have you done to your brother?”

“We were just having some fun, and we wanted to see which of us she resembles most.” Nancy explained.

“And?” Mother asked.

“Nancy.” Emma responded.

“I could see that with my own eyes.” Mother said, “My question still is ‘why’?” She turned to me. “How much of this was your idea?” I just mumbled some incomprehensible sounds in response. With that she noticed the bags from the stores.

“What’s in the bags?” she demanded.

“Some clothes,” Nancy said in a quiet voice.

“Whose?” Mother asked, only to see downcast eyes and no audible answer. Undaunted, Mother pressed on, “Your brother’s?” Emma just nodded. “Let me see,” she demanded, and my sister unloaded the bags on the kitchen table. “I don’t see any boy’s clothes here,” she commented.

Mother began to pick up each item and examine it. “I do admire your taste in clothes. But right now I want to talk with your brother, privately. You three go to your rooms and stay there until I call for you.” My sisters trooped up the stairs.

“Okay, Eugene,” she said, “tell me your side of what’s going on here.” By her use of my full first name meant that I was in trouble. Softly, and a little shamefully, I recounted the events which had started in the bathroom with Nancy, and ending with today’s shopping trip.

“So, why?” she asked, and I recounted the taking of pictures and the girls’ threats to publish them on social media. “Did you let a little blackmail cow you into doing all of this? I’m disappointed that you didn’t come to me when it started, You should know that I would have put an immediate stop to it.”

“Yeah, but,” I countered, “they said that you would believe them and not me.”

“And you believed them?”

“Yeah, I guess so.” I responded.

“There’s got to be more to this than you’ve told me,” Mother declared. “Answer me truthfully. You like dressing up as a girl, don’t you?”

Unable to answer, I just nodded my head.

“How long have you wanted to do this?”

“Ever since you dressed me as a girl for Halloween,” I answered.

“So, are you trying to blame me?” she said angrily.

“No, I’m not blaming anyone. I can’t help how I feel.”

“I want you to go to your room while I discuss this with your Father,” she commanded, “and take these clothes with you. I want them neatly put away in your dresser, or neatly hung up in your closet. By the way, keep on the clothes you are wearing until I say otherwise. Now go!”

I trudged up the stairs, only to be met by my sisters in the hall. “What happened?” whispered Nancy.

“Mon’s going to talk to Dad about this,” I whispered back, “I think we’re all in trouble.”

“I think that we should all obey Mom and stay in our rooms,” Nancy observed.

“Are you going to change?” Emma asked.

“Mom told me not to,” I whispered back.

With that we all retired to our respective rooms, to await our fates.

Chapter 6 - Consequences.

About a half an hour after being sent to our rooms, we heard our Mother summon us to come down to the living room. Dad had an unhappy look on his face but said nothing as we entered the room. Mother, as chief prosecutor, had us stand lined up by age. “Your Father and I are disgusted and disappointed with all of you, and here is what we are going to do about it.”

At this time, my Father spoke up, “I’m disappointed in you, Gene, for letting this happen. Further, I’m disgusted that you would want to dress as a girl. So, here’s what’s going to happen to you. You will dress in girls’ clothes except when you are at school or in church. I hope that will discourage your cross-dressing by getting it out of your system. We’re grounding you partly as a punishment, but mainly because I don’t want you galavnting around town in a skirt or dress. I’m afraid of the consequences of people seeing you as a girl, so your grounding is partly to protect you.

Now was not the time for me to say that being made to dress as a girl was hardly punishment; it was something I wanted to do, so I kept my own counsel.

Mother then focused on my sisters. “As you girls probably surmised, you are all grounded indefinitely,” Mother asserted. While your Father is disgusted with Gene’s cross-dressing, both of us are really angry that you attempted to blackmail your brother, regardless of the fact that he was so stupid to let you get away with it. I want you to know that any current or future hints of blackmail will be dealt with severely. Now, your Father will accompany each of you, one at a time, to collect your cell phones and any cameras which you might have. They are to be considered to be contraband, and if any of you fail to surrender all cameras and cell phones, your possession of contraband will be dealt with in a severe manner.”

She paused for a few seconds, and then said, “Nancy, go with your father and give him all cameras and cell phones.” As Nancy and Father left the room, Mother glared at the rest of us, and commanded, “You three stand where you are, and no talking with each other.”

One by one we all accompanied Dad while he collected our cell phones and cameras, all of which were deposited on the coffee table. Mother had kept us standing in a straight line, with no talking. She then stood next to Father and delivered an additional edict. “Your Father and I, knowing you to be clever children, suspect that you have uploaded some of the pictures to the hard drives of your computers. To prevent any dissemination of the illegal photographs, your Father has disconnected the wireless router,” she announced. With that Dad held up the wireless router. “We will attach anti-theft devices to all of your computers, to prevent you from taking them to a free wi-fi location.” she added. “Now, under your Father’s supervision, you will delete any photos of Eugene in a ‘compromising’ position which you have on your hard drives. When this is done, you will swear that you have no further photos. If it later turns out that some of these photos turn up, the consequences to all of you will be severe. Is all of this perfectly clear to you?” My sisters and I mumbled our assent.

Mother was not finished. “I want you to voluntarily delete any offending photos from your digital cameras and cell phones. Your Father and I will supervise this, starting with Nancy. Nancy, pick up your phone and any camera you have used in the last six months. The rest of you can sit down, separated from each other, and there will be no talking.”

The process of purging the photos took all the rest of the day and evening. I can honestly say that all of us were sufficiently afraid on the consequences that we deleted all of the prohibited photographs. When this was done, Mother had a final order, “All of you will promise that you will not take any photos of Eugene, without prior permission and supervision from either your Father or me. By the way, Eugene, that includes any ‘selfies’ you might take of yourself.” With that we were dismissed to go to bed immediately.

* * *

The next morning Mother marched into my room, unannounced and without first knocking. She immediately went to the closet to see that my girl clothes were properly hung up. She then went to my dresser to make sure that my other girl clothes were properly put away. “Okay, Eugene,” she finally said, “since you seem to like wearing skirts and dresses so much, every afternoon after school you will dress completely as a girl, under garments included, and remain that way until you go to bed. When you go to bed you will wear a nightgown. On the weekends, you will completely dress as a girl, except when you go to church. Is that clear?” I gave her my assent. “Nancy will supervise your compliance with this rule, and report any infraction. If Nancy fails to inspect you every day after school and at bed time, you will have to report her failing to either your Father or to me.”

The severity of the measures imposed by my mother were sufficient to cast a prison like gloom over the household for the next week. By the next Saturday Mom and Dad appeared to be satisfied that all blackmail photos had been located and deleted from our computers. However, my sisters and I all noted that before deleting any photos, Dad had copied them to a thumb drive. We wondered what he did with them.

Gradually, our cell phones were returned to us, and we were allowed limited relief from the grounding order, mainly to be able to attend after school activities. We were allowed to study with classmates, either at their house or ours. A few days later the wireless router was reconnected.

The next weekend the grounding edict was lifted and life more or less returned to normal, or at least as normal as can be expected in a house with four teenagers. On Saturday morning Mother took me aside.

“I’m no longer going to require that you wear girls’ clothes when at home, but, tell me, honestly, if you like wearing them?” she asked.

“Well, sorta,” I mumbled.

“Okay, get your sisters back in this room,” she commanded. When we were all assembled, she said, “Gene no longer has to wear girl’s clothes, that is, unless he wants to. To make sure that there is no undue coercion, I will have to approve of the same in advance. Now as to what Gene may wear; it must be modest, not tarted up. I was going to suggest that he wear nothing more risque than what you girls wear, but I realized if I said that you would dress like a bunch of hookers just to get Gene to look the same. So, here it is, Gene may only dress as you would when going to church. Do you understand? I want you to obey the spirit of what I have just said; no looking for loopholes.”

At that time I was wearing a skirt and blouse. “May I keep these on?” I asked Mother.

“As long as you like,” she responded, “but you might not want to while you Father is around, because he doesn’t like it.”

“How about at night?” asked Emma, “she, I mean he, has been wearing one of Nancy’s nightgowns when you were away, can he wear that?”

“If he wants to,” Mother answered, “Nancy,” she continued, “are you able to spare a nightgown?”

“No problem,” responded Nancy.

“Maybe we should buy Gene his own nightgowns,” Mother replied.

“She, I mean he, likes to wear a matching peignoir,” rejoined Emma.

“We can get him a matching peignoir,” Mother added with a smirk.

“I want to make sure that no one knows about this,” I interjected.

Mother laughed at this, and said, with a touch of sarcasm, “You mean that when you went shopping with your sisters you managed to become invisible?”

“That was different,” I responded, “everyone thought I was a girl.”

“And your point is?” Mother propounded.

“I don’t want any of the kids at school to know, I answered, “especially Sandy.”

So, everything returned to an even keel, at least for a time.

Chapter 7 - My Secret is Discovered.

Even though I didn’t dress as a girl for the majority of the time, I did like the way panties felt when I wore them, and frequently I would wear panties under my male clothes. This was all well an good until that fateful day. I had invited Sandy over to study french pronunciation from a program on my computer. I was wearing pink lace trimmed panties under my jeans, and somehow one of the cables for the computer became unplugged, and I bent over to plug it back in. Sandy was sitting next to me, and my jeans were a bit low on me, When I bent over Sandy spotted the waist band of my panties.

“What are you wearing?” she announced.

“Nothing,” I responded.

“No, it’s not ‘nothing,’ it looks like you are wearing panties under your jeans,” and with that she pulled up my t-shirt, exposing the entire waistband of my pink panties.

“You are wearing panties,” Sandy exclaimed, “Why?”

“I’m being punished,” I temporized.

“For what?”

“I’d rather not say,” I answered.

This bothered Sandy, and when she went downstairs to get some refreshments, Mother was in the kitchen, and noticed concern on Sandy’s face. “What’s the matter, dear?” she asked.

“Gene said that he’s being punished, but won’t tell me why,” Sandy responded, “it’s not like Gene to keep secrets from me.”

“He’s not being punished,” Mother responded.

“Then why is he being made to wear panties under his male clothes?”

“Oh, he is?” Mother responded, “just wait a minute,” and with that she called out, loud enough to wake the dead,” Eugene, come down here this minute!”

“Oh (bad word),” I said to myself, “I’m in deep (same bad word) now.” With that, I walked down to the kitchen.

Mother got right to the point. “Why did you tell Sandy that you’re being punished and have to wear panties under your jeans?”

“I donno,” I mumbled. A moment of silence followed.

“Why don’t you tell the truth? You know that your Father and I despise lying.” Mother asserted. She waited for my answer, but I said nothing.

“Why don’t you tell Sandy that you like wearing girls’ clothes?” she said, since I had not answered her previous question.

“Is that true?” Sandy said with a look of incredulity on her face.

“Yeah, I guess so,” I mumbled. I could imaging Sandy running out of the house, never to be seen with me ever again.

It didn’t happen. Rather, Sandy asked, “Could I see?”

“You have my permission,” said my Mother. “When he wants to dress as a girl, he has to get my permission first,” Mother confided to Sandy, “but you’ve got to promise to keep this a secret.”

“Okay,” answered Sandy.

“Why don’t you go to your room and get dressed?” Mother asked.

“Can I watch?” asked Sandy.

“Only if I’m also in the room,” said Mother. So all three of us went to my room. After undressing except for my panties, I went to my dresser and retrieved a bra and camisole, and some foam rubber breast forms which I had fashioned for myself. I put on the bra without any problem, inserted the faux breast forms and pulled the camisole over my head.

“He did that pretty quickly,” Sandy observed, “I bet that this is not the first time.”

I responded with a frown, and then went to my closet. Sandy stood up and moved next to me. In the back rack of my closet were my girl clothes. Sandy made humming noises when she saw the clothes. “May I pick something out for you to wear?” and without waiting for an answer she picked out a red and blue plaid kilt and a sheer white sleeveless blouse with ruffles.

“I have to wear a slip and pantyhose with that skirt and blouse,” I commented, and went back to my dresser where I took out a slip and pantyhose. I sat on my bed and gathered the legs of the pantyhose in a rose and slipped one foot in, after which I brought it up and did the other foot in a similar fashion, followed by pulling them up to my waist and then smoothed them on my legs. This caused a reaction, and I turned around so my back was to Sandy and tucked a part of my anatomy back between my legs.

“It’s obvious that you’ve done this before,” commented Sandy. I just grunted in response.

“Girls don’t grunt,” my mother said reprovingly. I just gave her a dirty look back as I put on my slip, and adjusted it. I then put on my blouse, and wrapped the kilt around me and fastened it, I then pulled up the hem of the kilt, reached under it, and pulled the tails of my blouse down to make it fit correctly. I returned to the closet and, squatting down, not bending at the waist, I took out my pair of flats, which I then put on.

“No heels?” asked Sandy.

“SHE is more comfortable with flats,” Mother answered, with emphasis on the female pronoun, “but maybe you should wear your heels for Sandy.” I changed into the heels. I walked back to the center of the room.

“Wow, you handle those heels well,” commented Sandy.

“Practice,” Mother commented, making sure that there was no doubt that I had dressed this way on prior occasions.

“I like the way her butt sways when she walks,” commented Sandy, now adopting the female pronoun.

“Okay, you two,” I said, “are you satisfied? May I change back to my regular clothes?” With that I sat on the bed, first smoothing my kilt under my bottom, and gracefully sitting on the edge of the bed, with my back straight, as I was taught.

Sandy chuckled. “The way you put you girl clothes on and move in them, I’d say that what you are wearing are your ‘regular’ clothes. Don’t you agree?” she said to my Mother.

“You saw what I saw,” my Mother commented. “Actions speak louder than words. Keep on what you are wearing.”

Mother suggested that we return to the kitchen for a snack. As we were walking to the kitchen, there was some hardwood floor which we had to cross, Naturally, my heels made the unmistakable clicking sound, which caught the attention of my sisters. I heard a snickering sound behind me, only to discover that my sisters, one by one had entered the kitchen..While they said nothing, the smirks on their faces said it all.

“I had nothing to do with this,” my Mother said in the way of a lame excuse, “I only gave my permission. All of this was Sandy’s idea.”

“I saw that she was wearing panties under her jeans, and one thing led to another,” Sandy said to my sisters.

Emma finally spoke, “She is a good looking girl, isn’t she?”

“Why don’t you give us a twirl,” suggested Nancy. I frowned at her.

“Yes, please,” said Sandy, enjoying every minute of my discomfort. “And, yes, she is good looking. Maybe she would look better with some makeup and her hair fixed in a girl style,” Sandy added, “I’d like to see the whole look.”

“Jean,” Gloria asked, “where are you hiding your makeup and hair stuff?”

“Yeah, where?” added Nancy. Mother looked at me, expecting an answer.

“In a box, top shelf of my closet,” I said with reluctance. Gloria went upstairs and returned with the aforesaid box, after which Nancy attacked my hair and Emma started with the makeup.

“Day or evening look?” enquired Emma.

“Go for evening,” responded Nancy.

“Don’t I have a say in this?” I asked.

“No,” answered Emma, who then turned to Sandy and said, “She’s pretty good at applying her own makeup, but on this occasion she can’t be trusted to do an ‘evening’ job.”

When Nancy and Emma were finished, I remained silent, stood up and clicked my way to the full length mirror in the hall. What I saw was a good looking teenage girl all dressed up for a date. While in the hall, I heard Nancy tell Sandy, “The best part is that her girl name sounds just like ‘Gene’ only it’s spelled differently.

“Why don’t you two finish your studying,” Mother suggested, “and then we can go out for pizza. My treat. Girls,” she said to my sisters, “why don’t you get a little more dolled up?”

She took Sandy aside, and whispered, “His Father and I hope that this is a phase which he will outgrow if we let him dress like this.” She was wrong.

Dinner at the pizza place was more or less normal, but only if a bunch of boys leering at us was normal, which my sisters assured me was indeed normal. “Mom being here restrains the boys somewhat,” Nancy confided to me.

For our next study session, Sandy insisted that ‘Jean’ be her study partner. I complied with her request, and was rewarded with some kisses. I told Sandy that when dressed as ‘Jean’ I tried to avoid my Father, since he did not approve.

Like a genie, or should I say ‘Jeanie,’ once being released from her bottle, wasn’t going to be ignored or forced back in the bottle. A part of me, which I genuinely enjoyed, was now free.

Gene or Jean? - Part 2 - French Class

Author: 

  • Pentatonic

Caution: 

  • CAUTION

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • School or College Life
  • Sweet / Sentimental

TG Elements: 

  • Corsets
  • Fancy Dress / Prom / Evening Gown
  • Performer/Entertainer

Other Keywords: 

  • CAUTION Adult encouraging minor to crossdress

Permission: 

  • Posted by author(s)

Gene or Jean? - Part 2 - French Class.
By Pentatonic

Chapter 8 - The Project for French Class.

Author’s Note: Some of the dialog that follows would naturally be spoken in the French language, but all of it is presented in English.

I was in the college prep program in high school, and had elected to take French to fulfill my language requirement. By my second year I was beginning to enjoy learning French. Part of that was due to the teacher, Mademoiselle Vert. Roughly translated, her name in English would be “Miss Green.’ Mlle Vert, aside from being very attractive, was a superb teacher, and this made her classes interesting.

My Aunt Lucille by marriage was originally from Quebec and spoke French. Since she and my uncle now lived only a short distance away, I was able to practice my French with her from time to time. In addition to this, she had a collection of what I loosely called French ‘cabaret’ or ‘art’ songs, some of which are hauntingly beautiful. With my Aunt’s help, I acquired recordings of many of these songs, along with scores and lyrics. I really liked Plaisir D’Amour written by Jean Paul Martini in the 18th century and Parlez-Moi D’Amour which was written in 1930 by Jean Lenoir. Among my other talents, I could play the piano and easily sight read most scores. I also had a good singing voice, if maybe a little higher than most of the other boys in the school.

One day, Mlle Vert announced that each student was to do a project as part of the grade. The scope of the projects was quite broad; it just had to be about France or the French language. Naturally all projects were to be presented to the class, and the use of English was forbidden. I knew immediately that I wanted to sing either Plaisir D’Amour or Parlez-Moi D’Amour or both. My Aunt was excited when I told her about the project. “You already know the accompaniment and melody,” My Aunt said, “but, mon cheri, your pronounciation must be perfect. Unfortunately,”she added, “my pronunciation is what is used in Quebec, not Paris.”

I finally decided on Parlez-Moi D’Amour, and submitted an outline of my project to Mlle. Vert. “That sounds wonderful,” she said and then added with a wicked grin on her face, “so are you going to dress up as Lucienne Boyer when you sing it?”

I frowned, “Hardly,” I replied, “a male may sing it.”

“But it would be wonderful if you did it as Lucienne Boyer, since she made it famous,” she said.

It was then that I noticed that Sandy had overheard that conversation. I hoped that she either didn’t understand what was said, or would just ignore it.

I decided to change the subject. “Could we get a piano or keyboard for this room?” I asked.

“I’ll see if we can,” she replied.

Shortly after choosing my project, I happened to mention it to Sandy, and we met at lunch to talk about our projects. Sandy didn’t mention what she had overheard about me dressing like Lucienne Boyer, and I most certainly wasn’t going to.

I asked about her project. Sandy had decided to do a presentation on French fashions.

“Do you have a color printer?” she asked.

“Yeah, why?” I answered.

“Because my printer is only black and white, and I want to print out pictures of fashions, and they will look better if in color,” she replied.

“How about Saturday afternoon?” I asked, “And you can hear my song.”

“That sounds great,” she said with a smile.

* * *

That Saturday I met Sandy at the door, with my sisters hovering around in the background. I had told them of Sandy’s project, and they were interested. As for my project, they couldn’t seem to care, since I was always singing and playing the piano. Sandy asked about the song I was singing and I showed her the score. It had a picture of Lucienne Boyer on the cover. I then played a recording of Lucienne Boyer singing the song. Hearing a female voice, my sisters suddenly became interested.

“So you’re going to sing a girl’s song?” Gloria asked with a snicker.

“It’s not a girl song or a boy song,” I instructed her, “both females and males have recorded it.”

“But are you going to sing it as a girl?” Gloria asked, ignoring what I previously said.

I just gave her a dirty look in response.

However, Sandy picked up on this exchange. “Didn’t Mlle. Vert suggest that you dress up like Lucienne Boyer when you sing it?” she interjected. Now my sisters were as interested in my project as a bunch of vultures looking at a fresh kill. This conversation was quickly getting out of control.

I tried to calm things down. “She said it as a joke,” I asserted.

“But you admit that she suggested it,” said Emma, with a wicked smile on her face.

“She wasn’t serious,” I said.

“How can you be sure?” Emma said, “after all, you do make a pretty girl.”

“As good looking as I am,” chimed in Nancy.

Sandy gave me a questioning look. “Just ignore them,” I told her, “we’ve got to work on our projects.” Finally, my sisters went away.

Chapter 9 - Preparations.

I found out from Mlle. Vert that she could not get a piano or keyboard for her classroom. “Don’t worry,” I said, “I’ll record the piano track to a CD and we can use a CD player for my project. I’ll still be live for the vocals.”

I began to work on my vocal range. Because I had not been doing a lot of singing, my range had shrunk. Only a lot of practice would do the trick. I decided to transpose the score to my highest tesseratura possible. This turned out to be a high tenor, or maybe a low alto. I liked a husky sound for my voice on this song.

Getting the correct vocal range was a minor problem compared with getting the pronunciation correct. This involved working with my aunt and listening to recordings time and time again.

Finally I had the music and pronunciation down pat. Only the presentation was still up in the air. My preference was to sing it as a man. I could wear black slacks, a black long sleeved turtleneck top, a black vest, left open and a black beret. I already had the slacks. I hoped to find a vest at the thrift store. I would have to buy the turtleneck, but I could use it when I dressed as a girl, same with the beret.

On the other hand, there was the image I had conjured up when listening to Lucienne Boyer’s recording. In my mind I could imagine it being late at night and being in a cellar nightclub in Paris, dark and smoky, where a beautiful chanteuse would come out from behind a curtain and sing one of these songs. I could imagine it was 1930 with Lucienne Boyer singing Parlez-Moi D’Amour.

Then there was hard reality. Unfortunately my presentation would take place in a high school classroom, with florescent lights, and obviously no tobacco smoke in the air. Furthermore, there was no beautiful chanteuse. I would be the one doing the singing, and I was no Lucienne Boyer.

I related all of this to Mlle. Vert, and told her I would prefer to sing it as a man. The alternative just seemed to be too difficult. My image of 1930 Paris didn’t comport with reality. “That is a beautiful image you created, mon cheri,” she said. “You know, I can get some room dividers to create a back stage area. We can turn off the lights and move the chairs so the light from the windows would shine on our pretend stage. You could start your CD of the accompaniment, and step out from behind the room dividers, and sing.”

“I guess that would be the best that we can do,” I said, “we’ll just not mention that we are pretending it’s 1930, and not mention Lucienne Boyer. I’m sure that none of the other students have ever heard the song before, let alone have heard Mlle. Boyer sing.”

“I don’t know,” Mlle. Vert said, “there was a movie some years ago where a boy was transported back in time to the 1930's in Paris, and Parlez-Moi D’Amour was part of the sound track.”

“I remember seeing the movie,” I said, “that’s probably where I got my image. However, I checked out the soundtrack and the song was an instrumental. No vocals.”

“Anyway,” I added with a cynical smile, “I presume that my grade on the project will greatly depend on how well I pronounce the lyrics, and not on the quality of my voice, or what I wear.” Mlle. Vert just smiled.

Mlle. Vert wasn’t going to let my image of 1930's Paris go. “When I was a little girl, my Grandmother had a recording of the song, sung by Lucienne Boyer, and I listened to it time and time again, and fell in love with it. I too had an image to go along with the song, and that image included Lucienne Boyer.”

“How is your voice?” she then asked.

“I’ve exercised my voice and I can sing high tenor and maybe even alto in addition to baritone,” I answered.

“Then maybe you can sound like a beautiful chanteuse?” she asked.

“I don’t know,” I answered, “anyway I have recordings of the song sung by a man, so I could do it as a male.”

“Yes, but I am captivated with the image you created, and I see it being sung by a woman,” she said.

“But I’m not a woman,” I replied.

“Your voice range is not too far off,” she said.

She then looked carefully at me, and finally said, “You probably could make a reasonable looking woman. Have you ever dressed in women’s clothes?”

I really didn’t want to truthfully answer this question, but I remember my Father’s advice, ‘When in doubt always tell the truth.’

Finally I admitted that I had.

“And how did you look?”

“I don’t know for sure, Okay, I guess,” I answered.

“Do you have any pictures?”

“No, but my parents might.”

I paused for a few seconds, and then asked, “I can’t very well wear a dress to school, so where could I change?” By asking this I had just moved singing as a girl from the improbable into the possible.

“We could get more room dividers, and make a sort of backstage changing area.” she suggested.

“I’d need help changing,” I said.

“Who are you thinking about?”

“Sandy,” I answered.

“Think about it, and we’ll talk about it later,” she concluded.

That night at supper I mentioned what Mlle. Vert and I had discussed. As expected, this caught the full attention of my sisters. “After supper, why don’t we check out the Internet?” Emma suggested.

Emma’s search resulted in several possibilities. One that my sisters liked was made of black polyester, with an A-line gathered skirt that flared out a bit. The bodice was tight fitting and made of lace, with a solid under part which went up to the bust. The lace top covered the solid part and had a vee neckline. It had lace 3/4 sleeves.

Included in the description were the sizes. Unfortunately my waist was too big and my hips and bust too small. When I pointed this out to my sisters, Emma suggested a corset. I wasn’t too sure about this.

We showed the picture to my Mother. “Do you have a dress like this?” Nancy asked.

“I don’t but why don’t we check with your Aunt?” suggested my Mother.

I didn’t like the way things were going. While I really liked wearing a dress in private, wearing it in front of the whole class was more than I wanted to do. “Look,” I said, “men have sung this song, so this whole idea of me trying to be a woman is not necessary.”

“It should be okay if you tell everyone it’s just a costume,” said Emma.

“I could do that, but most of my fellow students would ignore the costume part and only remember that I wore a dress,” I observed, “and give me all sorts of grief about it.”

Then I remembered about Mlle. Vert’s question about pictures. “Mlle. Vert asked if I had ever dressed in women’s clothes, and when I admitted that I had, she asked if I had any pictures, which I do not. Did you save any of the pictures?” I asked my Dad.

“I did.” he said, “Let me look at what I have and I will select a suitable one, if there is one that is suitable. Obviously one with you wearing a nightgown is not suitable.”

Mother was getting into the spirit of things. “Why don’t we check with your Aunt, and if she has something suitable, you could always get dressed, and your Father could take a picture.” She gave me an appraising look, and said, “Emma might be right, you might need a corset.”

At the mention of a corset, I gave my Mother a frown.

Later that week Mother and I visited my Aunt. She went to the back of her closet. Hanging in a garment bag was a black cocktail dress, with a knee length flared skirt, similar to the one we had seen on the internet. Also in the garment bag was a black corset. “You want to see if you can get into this?” she asked.

“I guess so, what’s the harm in trying.”

“Okay, ” she said, “Strip down and put on these panties.” She handed me a pair of black panties. In preparation, I had brought a black bra and my home made breast forms. I went to the bathroom and put on the panties and my bra, with the breast forms. When I returned, my Aunt gave me a knowing smile, and said, “It seems that you have worn women’s clothes before.” I just nodded my head.

Mother wrapped the corset around me. It had bra cups built in, so I took off my bra. The corset had garter straps, and fastened in front. In back were the laces. Mother fastened it, and began to pull on the laces. “Try this, and we’ll see how far we have to pull it.” With that she lowered the dress down on me, and tried the zipper. Of course it wouldn’t zip.

“I think another two inches should do it,” she said, and began to pull really hard on the laces. I complained about not being able to breath, and how uncomfortable it was. None of my complaints deterred my mother from the two inches. At last she was finished, and this time the dress was able to be zipped up.

“This corset is designed to enhance your cleavage. Put your forms in the cups, and let’s see what we have.” True to its design, it gave me a hint of cleavage. “I don’t think that I have any black hose, so you’ll have to get some. You might want to think about getting real breast forms.”
The next day my Mother and I went shopping. I put on the corset and my Mother laced it up. I then I put on my half slip, which was white, and my kilt. On top, I wore a camisole and a sheer sleeveless blouse, leaving the top buttons unbuttoned.

“You’ll need black underwear and a black slip,” Mother commented.

Suitably attired, my Mother and I went shopping. The black slip and hose were no problem. Then we went into a shop that had all sorts of under things.

A clerk approached us. “May I help you?” she asked.

“Yes, my son needs some breast forms. He has to wear a costume where he is a woman.”

“Oh, I see,” she said, “and is this your son?”

“Yes,” Mother replied.

“Come into the back room, and take off your blouse and camisole,” the clerk requested, which when I did, she noticed the corset. “You came prepared. What size are you looking for?” she asked.

“B cup,” my Mother answered.

“We have quite a few gentlemen customers. Let me show you the forms that most of them like,” and with that she took a box of breast forms off from a shelf. “These can be glued on, and the join line concealed with makeup. They come with instructions, and I can provide you with the correct adhesive and removal solution.” With that, she slipped a pair of forms into the cups of the corset. “These look like a good fit,” she commented.

My Mother grimaced at the price, but bought them along with the adhesive and remover.

Once back home, it was time to try everything on. My sisters insisted on helping, even though their help was not needed. I took off all of my clothes, except for the corset and panties. I then carefully put on the stockings. “Put the suspender straps under your panties,” my Mother suggested, “It makes it much easier when you have to use the toilet.” When this was done, Mother cinched the corset a bit tighter, despite my complaints. I put on the black full slip and a pair of shoes. Then it was time to put on the dress. To my amazement, it fit and could be zipped up.

“Let me do her hair,” Nancy insisted.

“I’ll do her makeup,” Emma said.

Mother joined in and applied some makeup to my chest to give me a hint of cleavage. I went to the mirror to see the final result, and was pleased with what I saw. I looked like a young lady about to go out for the evening to a night club.

“Okay, picture time,” Father announced. When this was done, Father went to the computer and printed out one copy each of two different photographs. “Just for your information, I have erased all of the photos from my camera and the computer, so don’t even try to find them.” He put the two photographs in an envelope and handed them to me. “For Mlle. Vert,” he explained.

When this was done, he announced, “I am not at all happy with this, and I hope that your Mlle. Vert doesn’t like them and this whole idea is abandoned.” He paused for a second, and then said, “However, after seeing the photographs, I’ll bet she loves them.”

Before the start of school the next morning I pulled Sandy aside and showed her the phonograph and briefly explained what was going on. “Wow, is this you? You’re gorgeous!”

I told her that I would give her a more detailed explanation after school.

After French class was over, I gave Mlle. Vert the photographs. “Oh, these are wonderful. You just have to wear this dress when you sing the song.”

Over the next few days, Sandy and I practiced getting me dressed, my hair done, and makeup applied. We decided that I would wear the corset, breast forms, hose and panties under my school clothes, and I would wear a bulky flannel shirt to cover everything up, since otherwise the corset and breast forms gave me an unmistakable feminine figure.

Chapter 10 - The Performance - Chanson Francaise.

Mlle. Vert’s classroom was not being used during the period before my presentation, and Sandy and I were able to arrange the room dividers to provide a secure dressing area. The desks had already been moved to face the impromptu stage. Mlle. Vert gave Sandy and me notes to give to the teachers of our classes immediately prior to my presentation, asking that we be excused from those classes. Sandy and I had a whole period to get ready.

Just before French class was to begin, Mlle. Vert arrived into the classroom, accompanied by Mr. Freund, the Principal; Ms. Morris, the Chorus Director; and Mr. Hanes, the Head of the Drama Department. Mlle. Vert told me that she had invited them to my presentation. “The chorus is planning to sing some works in French, and they wanted to hear your pronunciation and see your stage presence.” she explained.

When the class was assembled, she announced that everyone was to imagine that they were in a night club in Paris in the 1930's, and with that the overhead lights were turned off.

I started the CD player and slunk out of the backstage area. The class went up for grabs when they saw me, with a greeting of catcalls and whistles. I had anticipated that this might happen and had recorded some introductory music before the start of the song. Everyone quieted down, and the actual song began. I flashed everyone a big smile and began to sing, using a slightly husky voice, the following lyrics:
Parlez-moi D’Amour
Redites-moi ces mots suprêmes :
Je vous aime...
Which roughly translated into English are:
Speak to me of love
And say what I'm longing to hear
Tender words of love
I had brought a single rose, which was in a narrow vase on the so called stage. I picked it up, and moved forward, toward the principal.

With a sexy look on my face, I brushed the Principal’s cheek with the rose when singing, in French, naturally, ‘Tender words of love.’ The Principal’s cheeks turned as red as the rose, and everyone applauded. I then moved around the room, singing to each one of the boys, individually. The boys smiled; the girls gave me dirty looks.

Towards the end of the song, I moved toward the back of the stage, and at the end of the song, everyone applauded, especially the Principal. Well, maybe not everyone, some of the girls just glared at me. During the applause, I made a curtsey, and went back behind the room dividers.

Mlle. Vert then addressed the class, “I’m pleased that you enjoyed the song. Let’s have a round of applause for the Principal for being a good sport.” During this applause, the Principal stood up and beamed a smile at the class.

Mlle. Vert continued, “Would our chanteuse come back out, along with her, I mean his, wonderful assistant?” and Sandy and I came out for a curtain call.

“I want you to know that Gene played and recorded the accompaniment, in addition to singing. Would you like to hear it again?” They did, and I repeated the song.

“Does our chanteuse have anything else?” she asked.

“I prepared another song, Plaisir D’Amour, by Martini. Would you like to hear it?” They did, and so I performed it.

There was still some time left in the class period, and Mlle. Vert invited the members of the class to quietly discuss the songs and the performance among themselves, “In French,” she announced, “I don’t want to hear a word of English from any of you.”

While this was going on, the Principal and the chorus and drama teachers came up to me, along with Mlle. Vert, who then said, “The French only does not apply to the faculty and administration.”

“Thank you,” the Principal said, “because I took German in school.”

The Chorus Director looked at me and said, “You’re not in the chorus, are you?” and before waiting for an answer, she added, “I can always use a strong female voice like yours,”

“Unfortunately, I’m not female,” I responded.

“You certainly had me fooled,” she replied, “In any event, male or female, I could certainly use your voice, so will you join the chorus?”

“Wait a minute,” the Drama Teacher said, “How about me. She has stage presence, a strong voice, good moves, and I have lots of parts for her.” He paused for a moment, and then continued, “Did I hear you correctly, that you are a boy?”

“I am,” I responded.

“Then why sing as a girl?”

“Mlle. Vert and I listened to Lucienne Boyer’s recording of it. It was her song, and to get the right atmosphere for the song, I sang it as a girl.”

“Who did your costume and makeup?”

“My Mother did the dress, and Sandy did my makeup and hair today,” I answered.

“Even if you’re lured into the chorus,” he said, looking at the Chorus Director, “I really could use both of you backstage doing costumes and makeup. So promise me you will.”

“Okay,” we both replied.

Word spread about my performance, which was a good thing, because I wouldn’t have a chance to change out of the dress until after my last class, which was Health. Interestingly, the health class was studying sex education in general, and on that day, transvestites. Being dressed as I was, a lot of comments in the class appeared to be directed to me.

I was happy when I returned home and was able to take off the makeup and especially that blasted corset. Of course, that didn’t happen right away, because, as you can guess, Mother wanted to take pictures.

The next day, Sandy asked me to take a walk with her. “Gene,” she said, “the way you got dressed and undressed, you’ve done this lots before, haven’t you?”

“Yes,” I answered.

“And you have your own girl clothes.”

“You’ve seen them,” I reminded her

“How often do you dress like a girl?”

“It depends,” I said, “sometimes I dress when I come home from school, and stay dressed until I go to bed.”

“And what do you wear to bed?”

I didn’t answer this question, which probably was as good as admitting that I wore an nightgown.

“Gene, do you like being a girl?”

“Yeah, but I like being with you as a boy more.”

* * *

Author’s note: The English translation of the songs are as follows:

Parley-Moi D’Amour:

Speak to me of love
And say what I'm longing to hear
Tender words of love
Repeat them again
I implore you speak to me of love
Whisper these words to me, dear
I adore you.

I want to hear,
to hear those words that are so dear
I want to hear you say I love you
By all the little stars above you
Your voice is like a fun caress
It thrills me till I must confess
I long to hear the voice that brings me
Such thrilling love and happiness

Plaisir D’Amour:

The pleasure of love lasts only for a moment,
The pain of love lasts a lifetime.

You’ve left me for the beautiful Sylvia,
And she’s leaving you for another lover.

The pleasure of love lasts only for a moment,
The pain of love lasts a lifetime.

As long as this water will run gently
Towards this brook which borders the meadow,
I will love you, Sylvia told you repeatedly.
The water still runs, but she has changed.

The pleasure of love lasts only for a moment,
The pain of love lasts a lifetime.

Gene or Jean? - Part 3 - Consequences of Chanson Francaise.

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Sisters
  • Voluntary

TG Elements: 

  • Corsets
  • Fancy Dress / Prom / Evening Gown
  • Performer/Entertainer

Other Keywords: 

  • CAUTION: Adult encouraging minor to cross-dress

Permission: 

  • Posted by author(s)

Gene or Jean? - Part III - Consequences of Chanson Francaise.
By Pentatonic

Chapter 11 - After Chanson Francaise.

Well, I had admitted that I liked being a girl at times, but that I liked being a boy when I was with Sandy. My project, or maybe my performance was no secret, and most of my friends and acquaintances thought it was funny. On the other hand, a few people thought it was perverted, and made no secret of that.

I was even hit on by a few boys who admitted that they were gay, as if my cross dressing in some way made me gay. I gently corrected their misapprehensions. What was more interesting were the number of girls who hit on me. They made it clear that they wanted me as a girlfriend, since I looked sexy as a girl, and I had my male parts. I told them that I already had a girlfriend.

To everyone, I made it plain that my motivation to wear a dress had nothing to do with sex or my gender; I was motivated by getting an ‘A’ on my project.

“Yeah, but you seemed to be enjoying wearing a dress and acting like a girl. Way too much for just an ‘A’ it seems to me,” one of my male friends said.

“Well,” I responded, “I thought it best to act the part as well as I could. I always want to do my best.”

“Yeah,” he replied, “but you make one sexy chick. If I didn’t know better, I’d ask you out.”

“I don’t think that Sandy would like that,” I said in return, “and I’m not into boys.”

* * *

Mlle. Vert was most effusive with her praise. “I’d love to see you do it again,” she said, “It was one of the best projects I’ve ever seen or heard. By the way, your pronunciation was superb, even if you had a slight Canadian accent.”

“That came from my Aunt. She helped me with the songs, and she was born in Quebec,” I said. “I hope that the Principal wasn’t offended with me teasing him,” I said.

“On the contrary. He said that it’s been a long time since a pretty girl flirted with him. He really enjoyed it,” she said. “By the way,” she continued, “he wanted me to remind you that the school has a talent show at the end of the school year, and he hopes that you will sign up for it and repeat your performance.”

“I’ll think about it,” I said. I wasn’t too sure of it. Most of the contestants were garage bands, and some students singing covers of current songs. “I might do better if I gave some of them voice lessons and did their piano accompaniments, rather than performing myself”

“Oh, I almost forgot,” she added, “Ms Morris said that she would be glad to accompany you on the piano for the show, if you want.”

“I think that she wants to do it to get me into the chorus,” I commented.

“Yes,” she said, “she mentioned that too. She hinted at the possibility of some solo parts.”

“As a boy or as a girl?”

“I don’t know,” she answered, “you’d have to ask her.”

Chapter 12 - The Chorus.

Two days later, at home room, the teacher handed me a note. “From Ms. Morris, the Chorus Director,” he said.

The note asked me to show up at the next chorus practice, and gave the time and location of the same. ‘What the heck.’ I thought, “I’ll give it a go.” That is how I joined the chorus.

The chorus practice was after the last class of the day, and held in the auditorium.

I trooped into the auditorium with the chorus members. Ms. Morris saw me, and called out, “Eugene, can you come over here for a minute?”

She was smiling when I walked over to her. “I almost didn’t recognize you without your dress and makeup,” she commented. “I’m so glad you’re here.”

“What part do you want me to sing?” I asked, “and don’t I have to audition to join the chorus?”

“You already did, in your French class,” she said, “you’re so much better than almost all of the chorus members, and it appears that you can read music.” I admitted that I could.

“Where are the baritones?” I asked.

“Baritone?” she asked incredulously, “I’m thinking tenor, Come over to the piano, and let me check out your range.”

As we walked over to the piano, she called out to the assembled choristers, “I’ll be with you in a minute. Quietly look over your music until then.”

She played some warm up exercises, both up and down, and I sang them. “Well, I’ll be,” she said, “you have a great range. How did you do that?”

“I worked on my range for my French class project. I wanted my voice as high as possible, given the fact that I was wearing a dress when I sang,” I said, with a smile at the end.

Ms. Morris looked at me. “you really can sing baritone, but you also can sing tenor and even alto. Want to see if you can sing mezzo? I bet you can.”

“Okay, I’m game to try, but my tonal quality in the higher ranges is not that pretty,” I volunteered.

After a bit more singing, she said, “You’ve got the range. We can work on tonal quality. Why don’t you sing tenor for now. We always need tenors. Here is the score for the first number.”

She handed me the music, and called out, “Fred, wave your hand, we have a new tenor.” I went to where Fred was standing.

“I’m Fred,” he said, “I can sing either first or second tenor, and after hearing you, it appears that you can also. By the way, this piece is a medley with a tenor duet starting at measure 59. Are you willing to sight read it as second tenor?”

“Okay,” I responded, “If Ms. Morris wants me to. I don’t want to supplant the second tenor who’s been singing it.”

“Don’t worry,” he said, and he called out, “Hey, Joe, will you let Gene try the second tenor part, just for now?”

“No problem,” responded Joe, “You’re welcome to it, Gene.”

“What’s going on in the tenor section?” called out Ms. Morris.

“Gene’s going to sing second tenor for the duet starting at measure 59. Joe says it’s okay,” answered Fred.

“Are you comfortable sight reading it?” Ms. Morris asked.

“I’ll give it a try,” I said, “let me look it over for a few seconds.” It looked like a pretty simple harmony.

“Okay,” Ms. Morris announced, “we’ll start at the pickup to measure 59.”

So we sang the duet. I listened to Fred and blended with hm. It actually turned out pretty well.

“That was pretty good, great sight reading” Ms. Morris said, “but Joe, you’re not off the hook yet. I haven’t decided where I want to put Gene.”

So I sang with the tenors for the rest of the practice. When we were finished, Ms. Morris said, “Tenors are hard to find. Several of our tenors are girls, so I’m not going to waste your voice in the baritone section. I haven’t ruled out some counter-tenor solos for you.” A smirk crossed her face. “Of course, we could put you in a dress and have you sing an alto, or maybe a mezzo. solo,” she said with a laugh. “But for now, it’s a white shirt and tie, and the tenor section.”

I assured her that I was satisfied with singing tenor.

* * *

At supper that evening, I recounted my chorus experience, except for the remarks about the dress. “Ms. Morris said I have a great range, and can actually sing a higher part, like counter-tenor.”

This comment was not lost on my sisters. “So, you could sing a part wearing a dress,” Nancy said with a smirk.

“If you coached us, we could sing as an all girl quartet,” added Emma.

“With matching dresses,” chimed in Gloria.

My Dad was non-plussed. “Girls,” he said to my sisters, “enough of that.”

I couldn’t restrain myself, and got a jibe in against my sisters. “I might be flat,” I said, pointing at my non-existent breasts, “but you girls have a tendency to sing flat.”

“I can’t let you get away with such comments,” Dad said. “You will refrain from any digs at your sisters. They all have pretty voices.”

Ignoring the reprimand, I cast a smirk at my sisters. “Dad!” Nancy complained.

Chapter 13 - A Touch of Drama.

The drama department was casting its spring production. It was a conjured up musical with songs from various musicals and a thin plot. Mr. Hanes, the head of that department, was openly recruiting singers from the chorus. Ms. Morris referred to this a ‘poaching.’ “You can’t steal all of my best singers,” she complained.

“But I need them,” Mr. Hanes retorted, “I’m just borrowing them. I’ll return them after the production.”

“That’s what you always say, but you return them one or two short,” complained Ms. Morris.

“I can’t help it that they find the stage more exciting than choral singing,” Mr. Hanes replied with a smug smile.

As I expected, I was one of the choristers who was drafted. “But I thought that you wanted Sandy and me to help with costumes and makeup?” I said.

“Well, I’ve changed my mind,” he answered. “Ms. Morris let it slip that you were doing voice coaching and playing the piano, and I need both of those talents. Anyway, you won’t voice coach during performances, and then you can then work back stage with Sandy.”

“But what about the concert?” I asked Ms. Morris.

“You don’t really need the practice.” she noted, “You could come in cold and still sound great. Anyway, if I don’t let the drama department steal you, Mr. Hanes will mope around with a sad look on his face, and get everyone depressed.” she said with a laugh.

So I began voice coaching. I worked with all of the singers, and played the piano accompaniment for the practice. As a result, I learned all of the songs, and would sing along with the singers on occasion. Several of the songs were sung by an all girl trio, in harmony, sort of like the Andrews Sisters or the McGuire Sisters. Teaching the girls to sing harmony was a real task, but finally it all came together. Mr. Hanes was pleased with the results.

The costumes for the girls’ trio were very short tan skirts and white blouses with big chiffon sleeves. Because the skirts were so short, they had to wear matching panties and pantyhose. The 4 inch heels turned out to be ill-advised. At the practice before the dress rehearsal, one of the girls tripped and fractured her tibia. Mr. Hanes was frantic. “Where are we going to get a replacement?” he moaned. “Anyone have an idea? I’m desperate!”

“How about making it a duet?” someone suggested.

“I’d rather not,” he moaned.

I was sitting at the piano, ready to play the accompaniment for this rehearsal, since the orchestra wouldn’t join us until the dress rehearsal. One of the girls turned to me and softly said, “Too bad you’re not a girl, Gene, because you know our songs as well as we do, and you have a pretty voice.” Although she said this softly, it wasn’t that softly, and Mr. Hanes heard it between moans.

He strode over to us. We were afraid he was going to be angry with the interruption, but he wasn’t. “Stand up, you three,” he commanded. When we were standing he looked at us carefully. I was about as tall as the other girls, and being slender, looked to be about the same size. “Get someone up here from the costume department,” he commanded.

I began to get a funny feeling about this.

A few seconds later, Sandy appeared on stage. “Sandy, we have a problem,” he said, and explained the nature of the accident. “We need another girl to fill in, and the only likely candidate is Gene here.”

“But he’s not a girl,” Sandy said.

“Aside from that minor point, he’s the most reasonable replacement.” Mr. Hanes said to Sandy, “Will he fit in the costume, and can you make him look like a girl?” Sandy smiled at what Mr. Hanes had just said.

“Wait,” I complained, “the fact that I’m not a girl is hardly a ‘minor point’,”

Mr. Hanes and Sandy ignored what I had just said. “Yes, as to both of your questions,” Sandy told him.

“Well, then do it!” Mr. Hanes announced, and with that he turned to other problems.

Sandy took me to the dressing room. “This is going to be fun,” she said to no one in particular. “Gene, call your home, and see if anyone can bring over your bra and breasts. Maybe your corset and some panties and pantyhose, too.” All of my sisters were overjoyed to comply, after Sandy told them what had happened.

When my sisters arrived, they gave Sandy my clothes. Sandy directed me to put on my panties, panty hose, bra and breastforms. Luckily my sisters had also brought one of my camisoles. “For obvious reasons, we know that all of these are exactly the correct size,” Emma said with a chuckle.

I put on the blouse, which being loose, was no problem.

The skirt fit exactly, as Gloria observed as she zipped it up for me.

“Now the shoes,” Sandy said, “walk carefully, since these shoes have already claimed one victim.”

Nancy and Emma had me sit while Nancy did my hair and Emma did my makeup. When they were finished, they ordered me to stand and they stepped back to admire their handiwork, “Let’s go show her to Mr. Hanes,” Sandy said.

Mr. Hanes was surprised, amazed and pleased, all at the same time. “You’ve saved the show,” he exclaimed. While that might have been an exaggeration, it was nice to hear.

The production went well, and all sorts of family members, relatives and friends came to hearme sing and see me wiggle my bottom, strut my stuff, spin and show off my panties.

Chapter 14 - Recording a CD.

The talent show was called ‘Riverwoods’ Got Talent,’ which was modeled after a popular television show. It was set up as a contest, and there was a panel of judges consisting of Mr. Freund, the Principal; Ms. Morris, the chorus director; Mr. Phillips, a local record producer and Ms. Stone, the local newspaper’s music and art critic. The prize was a recording session. The audience was also allowed to vote, based upon the level of applause for each contestant.

I wore a dark blue pleated skirt and sheer blouse and all the necessary undergarments, including that nasty corset. I chose a pair of two inch heels for stability and comfort. Mom loaned me some costume jewelry. My sisters and Mom helped me get dressed and do my makeup and hair. While I knew that they derived some pleasure making me look like a girl, I also knew that they did it as an expression of sisterly love, something that I really appreciated. This didn’t prevent them from making the occasional snide comment, however.

I came in second place, so no free recording session. Well, I was pleased with second place. I had never even thought of recording my entries, because I performed en femme, and didn’t want to publicize my cross-dressing any more than I already had.

One can imagine my surprise when I received a telephone call from Mr. Phillips a week after the show. “I’ve viewed the video of the contest, and I’m impressed with your singing. I talked it over with some of the people I work with, and they think that there may be a market for a CD of French cabaret songs. We put together a list of additional songs to make a CD and to sell as singles on the internet. By the way, how old are you?”

“I’m fifteen,” I replied.

“Are you interested in making a CD?”

“I hadn’t planned on it, but now that you mention it, it sounds like fun,” I answered.

“In that case, why don’t you and one of your parents come down to the studio this Saturday to talk about it?”

“Sure,” I responded, “but why one of my parents?”

“Because we might want you to sign a recording contract, and you’re too young to sign it by yourself.”

“Oh,” I said. I paused for a moment, and then said, “Before we get into a recording session and a contract, there is something about me that you need to know, but I want you to keep it a secret.”

“What’s that,” he said with some concern in his voice.

“You’ve seen me perform as a girl. However, I’m not a girl, I’m a boy,” I confessed, and I told him how it came to be that a boy was singing dressed as a girl.

“Well, you fooled me,” he said, “not that it matters. It’s your voice that counts. We will need photographs for the CD cover and publicity, but having seen you, that will not be a problem. You make a sexy looking girl. Do any of the other panel members know?”

“The Principal and Ms. Morris,” I answered.

“It didn’t seem to bother them, so I’m not going to let it bother me,” he said. “Ten on Saturday okay with you and your parents?” I checked with Mother, and it worked for her.

“How do you want me to dress?” I asked.

“If it wouldn’t be too difficult, like you did at the show. Same outfit, same makeup,” he added.

When I finished the call, I explained the nature of what was proposed, as I understood it. My sisters had heard part of what was going on, and demanded to know all of the details. “So, my male sister is going to be a female recording star,” Emma commented, with a wicked smile. I stuck my tongue at her in response.

“Can we go along?” Nancy asked,

“Probably not a good idea,” Mother said, “But you can help her get ready.” There was that female pronoun again.

“How about it if she goes to a beauty shop on Friday afternoon?” Nancy suggested, “and get her all glammed up?”

“Wait a minute,” I interjected, “we’re not that far along yet.”\

“Yeah, but first appearances are important,” Mother added, “I’ll see if I can get her an appointment after school on Friday.”

* * *

For my trip to the salon, I wore a skirt and blouse, along with all of the necessary undergarments, including that cursed corset. Sally, the beauty shop owner greeted us when we walke in. “Now I know about Nancy, Emma, and Gloria,” she said, “but I never heard about Jean.”

“Neither had we, until a few months ago,” my Mother said with a big grin.

“But she’s your daughter,” Sally said, all confused.

“Not exactly,” Mother said, “she, or rather he, is my son.”

“Such a pretty girl can’t be a boy,” Sally said, “so, what are we here for?

“We’re going to talk to some people who want to produce a CD of her singing French cabaret songs. We want her to look as sexy and female as possible.”

“Wait a minute!” I exclaimed, “I have to show up at school as a boy on Monday, so no bangs, no highlights, and no curls. I want a style which I can make look male.”

“Those are tough conditions,” said Sally, “but I think we can do something.”

‘Something’ turned out to be pretty amazing. My hair was pulled back and some of it tucked behind my ears. The rest of it, despite what I had said, was trimmed to about shoulder length with a curl at the end. The crowing touch was a hair band. Sally explained how it could be converted to a male look. I liked it.

“Your ears are not pierced,” commented Sally, “We could do that here. A lot of boys have their ears pierced.”

“That’s a good idea,” Mother said, and my ears were pierced.

On Saturday, I did my makeup with a lot of ‘help’ from my sisters. While I wanted more makeup than normal for a daytime look, I didn’t go overboard. I wanted a slightly sultry look.

We carefully selected my outfit for the day. Pantyhose and heels were a definite. Unfortunately, so was the corset. I wore the same outfit as I wore for the talent contest, a dark blue pleated skirt and sheer blouse.

* * *

The recording studio was not what I had expected. It was on the second floor of a building whose first floor was a photograher’s studio. It had been an apartment many years ago, and the studio itself was two rooms, with a glass window between them. The main room had some kind of sound absorbing materials on the walls and ceiling with microphones and wires all over the place. There was an upright piano on wheels in the corner. I hoped that it was in tune.. The smaller room was the control room, with all of the recording equipment. In the back of the space was a small office. The kitchen, from the days as an apartment was still there, with old appliances and a beat up kitchen table. The most important thing was the coffee maker, and that was new.

Mr. Phillips greated us at the top of the stairs. “I’m so glad to see you here. I think we have a winner here.” He introduced us to the others present. “This is Joe, our electronics expert, and this is Steve, who handles the mics. Over there,” he said pointing, “is the photographer whose studio is downstairs. With him are some other helpers. We’re waiting for the co-producer who is arranging the funding for this take.”

Mr. Phillips looked me up and down, with the smile on his face growing. “Are you sure that you’re a boy? You could fool anyone.” He then called the photographer over. “How does she look? Any sign of a boy here?”

“Looks great,” the photographer said, “no sign of a boy.”

“Okay, gang,” Mr. Phillips said, “let’s start this with a look at Jean’s performance at the contest.” Joe turned on a video monitor, and started my part of the show. “We’re going to only do an audio CD. However, if we make it big, we might want to do a music video later,” Mr. Phillips added.

When the video of the show was finished, Joe said, “They could have done a better job with the mics. I see that you didn’t use a mic when you sang. We’ll have you use one when we record,” he added.

“Okay,” Mr. Phillips said, “What are you going to sing?”

“I prepared three songs,” and I handed him the scores. “Two of them are what I sang at the show; Parlez-Moi D’Amour, and Plaisir D’Amour. I worked up a third one, La Vie En Rose, if we have time for it.”

“How do you want to do this?” Mr. Phillips asked, “you said you would do the piano accompaniment.”

“I was thinking of laying down the piano track and then combine it with me singing. I even worked out two vocal parts so I can sing melody and harmony,”

“Why don’t you run through the piano part, and I’ll arrange the mics when I hear what it sounds like,” Steve said, “then we can do the vocal parts.”

The songs are not long, so I did three takes of each of the songs. “Now do you want me to do the duets?” I asked.

“Sure,” Mr. Phillips said, and we did.

During the recording session I saw a new person in the control room, who I assumed, correctly, was the co-producer, Mr. Nicholas.

When we were finished, Mr. Phillips said that he had to talk with Mr. Nicholas, and that there was coffee and cold drinks in the kitchen. He also suggested that we go downstairs for some photographs, which we did.

Mr. Phillips and Mr. Nichola were waiting for us in the kitchen when we returned from the photography studio. The Photographer came up with us and handed some digital photos to Mr. Nicholas. He gave Mr. Phillips a thumbs up.

“Let’s talk,” Mr. Nicholas started out, “We like your singing, and would like to produce a CD, and arrange for some on-line sales of individual songs. “We would like to record between fifteen and twenty songs to fill the CD, so we would like you to select either those or some other songs, all in French. We have a contract for you to review, which is conditioned on you doing the additional songs as well as the ones you did today. Additionally, we are going to send your picture and the recording of the three songs to an associate of mine in Montreal, for his opinion as to the market in Quebec. He might release demos to test the market.”

“The contract has all of the financial details, and you should look at them carefully,” Mr. Phillips added. “If the songs are only a marginal success, most of the money will go to recovering our production costs. Your share depends on how well the sales go.”

“And if it’s a total bust, who pays your production costs?” Mother asked.

“In that case, we absorb all of the production costs,” Mr Nicholas replied, “but I think it will be a success, based on what we heard as of now. Take the contract to your attorney and get back to us.”

“Well, that just about finishes it for today. Do you have any questions?” Mr. Phillips asked.

“Yes,” I answered, “can I get a copy of what was recorded today and some copies of the photographs?”

“Certainly,” he replied. “Just remember that you may not sell copies of either. We reserve those rights for advancing the costs of production. Joe, give her a CD of the session, and here are some digital copies of the photos.”

“Thank you,” I said.

“Okay,” Mother said, “You’ll hear from us in a day or so about the contract. Thank you for all you’ve done.”

With that, we all shook hands and Mother and I returned home, only to have to go over all of the details of the session with my sisters and Father. All of them loved listening to the CD. My sisters liked the photos, my Father did not. “Gene, as you well know, I don’t like you dressing as a girl. I understand why you’re doing it for the CD, but that doesn’t affect how I feel.” He paused for a moment. “Having said all that, I do have to say that you make a beautiful girl,” he added with a smile.

* * *

It didn’t take me long to select another seventeen songs. What took time was arranging the accompaniment and getting the pronunciation exactly correct. For that I sought out my Aunt and Mlle. Vert.

When everything was correct, I called Mr. Phillips and arranged to record the other songs. When Mother and I arrived at the studio, Mr. Phillips and Mr. Nicholas were both there, with big smiles on their faces. “We’ve heard from Montreal.” Mr. Nicholas said, “As you remember, we said that we might released them there, and the three songs you already recorded doing well on internet sales. There appears to be a demand for the CD.”

“Then let’s get the rest of the songs recorded,” added Mr. Phillips.

* * *

A few weeks after the CD was released, I received a surprise call from Ms. Stone, the critic for the local paper, who had been a member of the panel for the talent show. After introducing herself, she said, “I noticed a piece in the trade paper saying that a CD of cabaret songs has been released, and was doing well for a foreign languge recording. The name of the artist rang a bell, and I finally connected you with the CD. Are you aware of this?”

“To the extent of the royalty checks I’ve received, then the answer is yes,” I responded.

“I liked your singing at the talent show, so I ordered the CD, and I like that even better. I also did some checking, and spoke with Mr. Hanes at your school. He related an interesting fact, that you jumped in when a girl broke he leg, despite the fact that you’re a boy . I saw that production. I always thought you were a girl, until Mr. Hanes told me differently.”

“Well, I’m trying to keep that fact from wide distribution,” I said, “that’s why I told Mr. Hanes to not announce that I was taking the injured girl’s part.”

“But now you have a CD with the picture of a very pretty girl on the cover,” she said, and then paused, “so whose picture in on the cover?”

“Mine.”

“Oh wow, if your story got out, now that would be news,” Ms. Stone said.

“I hope it doesn’t,” I said. “After all, a CD of foreign language songs has to have a very limited audience.”

“Not in Quebec,” she responded, “sales are doing very well there. I wouldn’t be surprised if you had requests for personal appearances.”

‘Oh, (bad word)’ I thought.

“Anyway,” she continued, “the reason for my call is that I’d like to do an interview of you.”

“I’d rather you didn’t,” I said.

“Well, you don’t have to allow an interview, but there is enough material available for me to do an interesting article even without an interview,” she said with the hint of a threat in her voice.

“If I do an interview,” I said, “could you agree to, and keep certain items out of the article? As and afterthought I added,” and no photographs”

“Wrong. My editor and I want photos.”

“With me as a boy or as a girl?”

“Your call,” she said.

“Okay, I’ll do the interview as a girl,” I agreed, and I did.

When the article appeared, it was titled ‘Local chanteuse a hit on the international scene.’ I was identified only as ‘Jean.’ with no last name.

There was very little fallout from the article. It appears that most of the students at my school weren’t interested in French cabaret songs. Mlle. Vert was interested, and had me autograph a copy of the article, as I did for Ms. Morris, Mr. Hanes and the Principal, Mr. Freund.

Four out of the other five members of my household were happy to have a sister and daughter who was a minor celebrity. My Father wasn’t.

And then there was Sandy. “I’m really pleased for you, but I can’t brag that my boyfriend is a noted female singer,” she complained, but with a smile.

* * *

Over the summer I was asked to go to Montreal to promote the CD and to give some concerts, which turned out to be a lot of fun. I even did an interview on a local television station, and sang one of my songs. My Mother went with me, even though my sisters really wanted to go. I celebrated my sixteenth birthday there. One neat thing about my trip was that I was able to use some of my royalties to buy clothes for the trip, female clothes that is. Naturally, my sisters demanded that they accompany me on my shopping expeditions.

I had to get a passport which identified me as ‘Eugene,’ a male, so I had to travel as a boy. When I packed my suitcases, I was sure to put boy clothes on top, so if my suitcase was opened, a bunch of frilly girl clothes would not immediately be visible. As it was, I didn’t have any problem at the borders.

It appeared that I was better known in Montreal than in my own home town, a situation which I liked.

However, my musical career was only beginning, which meant that I was spending more time as a girl than I had before. As can be imagined, this led to certain situations which needed to be resolved.

Gene or Jean? - Part 4 - Looking for Answers

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • School or College Life

TG Elements: 

  • Corsets

Other Keywords: 

  • Recording a CD and music video Counseling

Permission: 

  • Posted by author(s)

Gene or Jean? - Part IV - Looking for Answers.
By Pentatonic

Chapter 15 - Am I a Boy or Am I a Girl?

As a result of dressing as a girl for my French class project, I was spending more and more time as a girl. While Sandy had been enthusiastic about my cross-dressing at the start, she seemed less and less in favor of it as time progressed and I spent more time en femme. She wanted a boyfriend.

My Father just didn’t like it. He was reluctant to discuss my cross-dressing; he left it to my Mother to tell me of his concerns. “Your Father had hoped that your cross-dressing was a phase and that you would grow out of it.” she said, “Now he thinks that you might be turning into a girl. He thinks that you are more girl than boy, and he wants you to go to counseling.”

Sandy shared my Dad’s concerns. Therefore, I agreed to go to counseling.

Because my Father was going with my Mother and me. I decided that wearing my boy clothes would be a good idea. The counselor shared an office suite with several other professionals in a building downtown. Nothing really fancy. We told the receptionist that we had an appointment with Dr. Lisa Goodman and a minute later Dr. Goodman escorted us into her office.

“Now, why don’t you tell me why you’re here?” she asked.

“My son, Gene, likes to dress up like a girl, and I’m afraid that he wants to become a girl,” my Dad declared.

“Is that correct, Gene?” she asked me, “do you like to wear dresses and skirts?”

“I do, on occasion, wear a dress or a skirt,” I answered. I decided to not volunteer any information, so aside from answering her question, I said no more.

“So, do you wear any other girls’ clothes when you wear a dress or a skirt?”

“Yes.”

“What?”

“Everything,” I replied. This time I decided to expand my answer, “panties, pantyhose, slip, camisole, bra and heels.”

“How does that make you feel?” she asked.

“I like it.”

“You’re dressed as a boy right now. Why?” she asked.

“Dad doesn’t like seeing me in a dress or skirt,” I answered.

“Is that right, Mr. Torne?” she asked my Father.

“Yes.”

“How about you, Mrs. Torne?”

“You wouldn’t believe how cute he, or rather she, is when all dressed up in a skirt or dress,” my Mother answered.

“I take it that you approve of his cross-dressing?”

“Well,” my Mother started to say. She then looked at my Father and continued, “I know that my Husband doesn’t like it, so rather than saying I approve it, let’s just say I don’t object.”

“Do you ever help him cross-dress?”

“On occasion. However, my three daughters seem to enjoy helping him dress,” my Mother answered, “So he doesn’t always need my help.”

Dr. Goodman then shifted the conversation. “So, why are we here, and what do you hope to accomplish?” she asked all of us, in general.

“To find out why he likes to cross-dress, and to figure out if he wants to become a girl,” my
Father answered.

“Is that correct, Gene?” Dr. Goodman said.

“Pretty much so,” I answered.

“Why?”

“I’m curious, and I think that my girlfriend would like to know,” I responded.

“You have a girlfriend?”

“Yeah,” I answered.

“Are you and your girlfriend intimate? By that, I mean do you have sex?” she asked.

“Nothing outside of an occasional kiss and hugs,” I responded. From the corner of my eye, I could see that my parents were relieved with this answer.

“Gene, have you ever gone out in public wearing a dress or skirt?” Dr. Goodman asked.

“Yes.”

“Tell me about it”

“I had a project in French class, and I sang some cabaret songs in front of the class, and I wore a dress for it because I was imitating Lucienne Boyer. I then filled in for a girl who broke her leg in a musical being produced by my school and had to wear her costume, which included a mini-skirt. I also repeated the cabaret songs at a talent show held by the school. Each of these time, I wore female clothes.”

“How did that go?” she asked.

“Fine, no problem/ My voice range is high enough to sound like a girl.” I answered.

“Tell her about Montreal,” Mother interjected.

“What about Montreal?” Dr. Goodman asked.

“Well, based on my performance at the talent show, a record producer wanted me to do an album of French cabaret songs, which I did. The album and some singles were introduced in Quebec, because all of my singing was in French. The album has been doing fairly well for what it is, and I was invited to Montreal to promote the album and for some concerts. Naturally, I dressed as a girl for all of this. I couldn’t dress as a boy, because my photo as ‘Jean’ was prominent on the CD cover, and everyone expected to see a girl,” I answered.

“So you dressed as a girl when you performed. I can see why you did that. However, do you ever go outside as a girl when you aren’t performing?” she asked.

“Yes. When I shop for clothes, and sometimes just when I feel like doing it,” I responded.

Nothing further was said for a few moments while Dr. Goodman made some notes. She then continued, “Well, before our next session, I have questionnaires for each of you to fill out,” and she handed each of us a questionnaire. I could see that mine was thickest. “I want you to be totally candid with your answers, so it would be best if you didn’t share your responses with each other. If Gene knew that you would see his answers, it may affect what he says.”

Dr. Goodman then turned to Mother, and said, “I want Gene to have a complete physical exam, and to have some blood tests done. I have a list of what tests I want,” and she handed a paper to Mother. “I would like to listen to the CD, if possible, and would like to see some photos of Gene while dressed.”

With that, the session ended.

* * *

My sisters and Sandy wanted to know all about my counseling session. “Well,” said Emma, “do we have a new sister, or still have an icky brother?” I chose to ignore the question.

Sandy wanted to know if I was turning into a girl, for other reasons than those expressed by my sister. “I think we are growing closer,” she confessed, “and I don’t want to be a lesbian.”

The questionnaire was lengthy and comprehensive. I did note a lot of questions which related to whether I thought that I was a girl trapped in a boy’s body, and whether I thought that I should have been born a girl. I gave negative answers to these questions. There were a lot of questions about my sex life, which I found a little amusing, since to date I didn’t have a sex life. Other questions asked if I had ever dated or had sex with a boy. Some of the questions gave me an insight into other sexual practices, such as anal sex. I had never even heard about this before, not even in sex education classes.

The next counseling session was a continuation of the first. We all turned in our completed questionnaires. “I want to review the questionnaires before out next session,” Dr. Goodman said. She then turned to the results of my blood tests. “Gene, the tests show that you have a slight hormone imbalance. Other than that, all of the tests are normal.”

“What does the hormone imbalance mean?” I asked.

“It means that your estrogen level is higher than usual, and your male hormones are slightly lower. It’s nothing to be alarmed about, because the imbalance is not severe. I’d like to monitor it in the future.”

“Does this mean that I’m turning into a girl?” I asked.

“At this time, probably not, since the imbalance is slight. Your doctor noted that you have not started puberty yet, and that must be factored in. When you go through puberty, that all may change. If you notice any changes in your nipples, please bring that to my attention, because that may indicate that the imbalance is increasing.”

Am I growing tits, I wondered?

At the end of that session, Dr. Goodman said, “I’d like to have Gene come to the next session fully dressed as a girl. Mr. Torne,” she said to my Father, “you do not have to attend if seeing your son in a skirt or dress would bother you.”

“I have seen him in a skirt or dress many times, and it does bother me, but what we are doing is important, so I’ll be here,” my Father answered. Dr. Goodman liked his answer and smiled with approval.

I dressed very carefully for my next counseling session. I decided to wear a dark blue knee length skirt, which meant dark pantyhose, black panties and a black half slip. Naturally, I had to wear the corset. Because the corset was black, I decided on a dark brown sweater on top. I wore a pair of black heels. I had Nancy help me with my hair. She pulled it back and used a red hair band. My makeup was daytime, and the colors subdued.

While my parents and I were walking to the car, my Father said, “Despite not liking you wearing girls’ clothes, I must honestly say you look very pretty, pretty enough for a father to be proud of the way his daughter looks. So, rather than being unhappy, I’m trying to be proud of my cute daughter.”

“Dad, that’s the sweetest thing you could say,” I replied, “Thank you,”

Dr. Goodman checked me out when I arrived with my Parents. ‘Stand up tall,” she commanded. “Now turn around.” I slowly turned completely around, and then did a fast twirl, which lifted my skirt. Dr. Goodman smiled.

“Now let me see you walk.” I walked a few steps in her office. “Let’s try this in the hall,” she said, and we all went out into the hall where I walked the length of it several times. When we returned to her office she carefully watched as I sat down. “You present yourself well as a girl,” she said, “how much of that is from practice and how much is natural?”

“My sisters were more than happy to spend countless hours coaching me,” I answered, “so I have no idea how much is natural.”

“But you look all girl,” Dr. Goodman commented. “So there must be something in your appearance that is natural.” She made some notes on a pad.

“You have a feminine figure,” she said, “how do you do that?”

“A corset,” I responded, “a painfully tight corset.”

“Other than the corset, what else are you wearing under your skirt and sweater?” she asked.

“Pantyhose, panties, bra with breast forms, a half slip and a camisole.”

“Am I correct in assuming that you have a complete feminine wardrobe with multiple skirts and dresses, along with underwear?”

“Yes,” I answered. “I needed a lot of clothes for my trip to Montreal,” I explained.

“Are you ever afraid that you will be ‘read’ when out in public?” she asked.

“I’m not aware that it ever happened, so my answer would be no. Of course, a lot of people know that I’m a boy in a dress, by reason of my performances,” I answered.

“You said that you sometimes go out of the house dressed as a girl, for no particular reason, other than to just do it?”

“Yes,”

“Why?”

“I like dressing as a girl. I like the way the clothes feel. I like the way boys check me out, and I just like being a girl,”

“Would you like it if you could dress as a girl all the time?” she asked.

“I haven’t thought about it, because there are so many times, like when I’m in school, when I have to be a boy.” I answered, “and I don’t think that Dad or Sandy would like it.”

“Do you ever imagine yourself getting married, and if so, as a groom or a bride?”

“Both,” I answered, “you see, I am close to Sandy, and if we married, I would have to be a groom. I cannot picture myself as a bride to any of the boys I know, so the boy in my imagination is rather vague.”

“Would you like to have children?”

“I think so,” I admitted, “but I haven’t looked that far ahead.”

“Have you ever dated a boy?”

“No.”

“Do you want to?” she asked.

“I don’t think so,” I replied.

Dr. Goodman then changed the direction of our conversation. “Your Father has said he does not like you presenting yourself as a female. Does how he feel impact into what you have told me?” she asked.

“I know how Dad feels. I love him, and I respect his opinions, so I would have to say that how he feels impacts my answers,” I responded. I turned to look at my Father and he looked happy when I said this

“There seems to be uncertainty as to whether you want to be a girl,” Dr. Goodman observed, “we’ll have to explore that in further sessions.”

No conclusions yet.

Chapter 16 - The Dating Game.

Shortly thereafter, I mulled over the question that Dr. Goodman had asked me; if I ever dated a boy. I wasn’t sure that I had even formally went on a date with Sandy. We were close, but had we gone out on a date? I decided to change that.

Sandy and I were studying together one afternoon. “Would you like going out with me to a movie or something like that?” I asked Sandy.

“You mean like on a date?” she responded.

“Yeah, I guess so,” I responded.

“Sure,” she said, “when?” She paused, and then continued, “with the boy Gene or the girl Jean?”

“The boy,” I answered.

“Good!” she said.

I had my drivers’ license by then, so I suggested a movie and pizza. Hardly original. We arrived at the mall with some time before the movie was to start, and Sandy suggested we browse the music collection at one of the stores. While most CD sales were on-line, the store had a reasonable number of CD’s for sale. Tucked away in a corner was a display of foreign language CD’s.

“Let’s look if there are any CD’s which would help us in French class,” she suggested. I noted that there was a terminal to look up CD’s which could be ordered and picked up at the store.

There was a clerk at the terminal. He asked us what interested us.

“French language.” Sandy responded.

“You know, there is a CD in French by a local singer, Jean or something like that. We have it in stock in the foreign language section. One of my friends bought one, and I listened to it. Nice looking chick on the cover, and what a sexy voice. I’d like to meet her.”

I started to blush, but he didn’t see that. “I think I know the CD, and I already have a copy,” Sandy said, “and you are right, she is good looking and her voice is really sexy.” I, the owner of the ‘sexy’ voice continued to blush, but said nothing.

“Are you selling a lot of them?” Sandy asked.

“More than I would have otherwise expected. Maybe because she is from around her, or maybe because she has such a sexy voice. I just don’t know,” he said.

We left the store without buying anything. As we were walking to the movie theater, Sandy could not resist teasing me. “I see that you with the sexy voice said nothing.” she said, “afraid of giving yourself away?”

I just grunted in response.

The movie was nothing special, no Oscars for it in the future. What was special was that when I put my arm on Sandy’s shoulder, she laid her head on mine.

We continued to date. After one of these dates, Sandy said, “We’ve been dating for a while, and you seem to enjoy it. I know that I do.” She then let the other shoe drop. “You’ve never gone on a date with a boy, have you?” I admitted that I hadn’t. “Most girls like going on dates with boys,” she posited. “If you think you are a girl, shouldn’t you at least go on one date with a boy?”

“Wouldn’t that be like cheating on you?” I said.

“Not if you had my approval,” she answered. “I think that you need the experience.”

“No boy has ever asked me out for a date,” I said.

“That’s because all the guys know you’re a boy and going out with me,” she responded.

“If a boy asks me out for a date, I’ll think about it,” I said, “but no promises. What happens if he’s a total jerk? I don’t want to go out with a jerk.”

“Okay, no jerks,” she said.

“I don’t know,” I said, “I’d be scared to go out with a boy,”

“Maybe I can arrange for a double date, if you don’t mind me going out with another guy,” she suggested.

“I don’t like you going out with another guy,” I complained.

“You’re jealous,” she responded, “how sweet.”

Despite my reservations and concerns, Sandy arranged a double date. We would meet the guys at the movie so neither would know my address. Sandy’s date, Bill, was a friend of her cousin. My date, Bob, was a cousin of Bill’s.

Some way my sisters found out about my date. I think that Sandy leaked it to them. In any event, they went into high gear getting me ready. “A little black dress!” exclaimed Emma.

I did not have a little black dress of my own, but Nancy had one that fit me. With my corset, it gave me a nice looking figure. “Pantyhose, or stockings?” was Emma’s suggestion.

“We can put straps on the corset, so stockings are possible,” Nancy said.

I had very little input into the whole process. I wanted to complain that the dress was too short, but to no avail. When they were finished, I looked in the mirror and saw a cute, sexy, teenage girl.

I had told my Parents that I was going on a date. I just didn’t say with whom. My Parents naturally assumed that I was going out with Sandy. In a sense, this was partially true.

I drove to Sandy’s house. Driving in heels was, well, ‘different.’ We did, however, make it safely to the movie theater. Sandy had arranged to meet Bill and Bob at a kiosk in the mall. After introductions and some small talk we went to the theater. We sat together in the theater, Bob to my left and Sandy to my right, and Bill to Sandy’s right.

While in the theater I let the hem of my dress ride up, exposing a hint of my stocking tops. Bob noticed, but then he leaned over to me and whispered, “I appreciate the show, but you should know that I’m into boys, not girls.”

“You mean you’re gay?” I whispered back, “as opposed to being transgendered.”

“Gay, not transgendered,” he whispered in response.

“Then why are we on a date?” I asked.

“My Parents,” he answered, “When I told them I was going on a date with a girl, they were overjoyed. They don’t approve of my orientation. I hope that Bill can take a photo on his phone to show them. It’ll take some of the heat off of me.”

I had to smile at this. If only they knew the truth, they’d probably blow a gasket, I thought.

Halfway through the movie, I decided to try something. I took his hand in mine and held it. He made no attempt to stop me and take his hand back. After the movie, Bill suggested that rather than a pizza we got some takeout and ate it at his house. On the way to his house, Bill and Sandy rode together, That left Bob and me in my car.

On our ride to Bill’s house, Bob said to me, “If I wasn’t gay, I’d really go after you.”

“No, you wouldn’t,” I answered.

“Why,” he asked.

“I’ve got a secret, and if I tell you it’s got to remain a secret. Okay?” I said.

“Okay,” he replied, “so what’s the secret?”

“I’m a boy.” There, it was out.

“You mean that you have a p. . .” he started to say.

I interrupted him in mid sentence, “Yes.”

“Wow,” he said with astonishment, “I’d never have guessed. You look so feminine.”

“That’s the goal of every cross-dresser,” I said, “to look so much like a girl so that no one would guess.”

When we parked in front of Bill’s house, he touched my face with his hand, and turned it toward his. He then leaned over the front seat console and kissed me. I felt his tongue on my lips and opened them up.

When we broke off the kiss, I though, ‘Wow, I’ve just kissed a boy.’

“That was for being so nice,” Bob said, “this evening has to have been weird for you, but it means a lot to me. As you saw, Bill took some photos, which I’m going to show my Parents. My Parents strongly disapprove of my homosexuality. They think it’s a phase which will pass once I met a ‘nice girl. I’m sure that you understand that’s not how it works. Anyway, they demanded that I go on a date with a nice girl. What is really funny is that you are supposed to be the ‘nice girl.’ They are happy that we are going on this date. If they knew all of the facts, they would go ballistic.”

“I think that I understand,” I said, “My Dad really hates my cross-dressing, but he tolerates it because of the money.”

“What money?”

“I recorded a CD of French cabaret songs as a girl, and I’ve been receiving royalties from the sales. Not a lot of money, but Dad can’t ignore it. Anyway, I am glad if I can help you with your parents.”

With that, we went into Bills house to eat the take-out food.

While driving home with Sandy, she asked, “Now that wasn’t too bad, was it?”

“No, I actually had a good time,” I answered.

“Did Bob tell you about his parents?”

“Yeah,” I answered, “and Bob and I think that it’s really funny that I’m the girl.”

“So you told him?” Sandy asked.

“Yeah, it seemed to be the right thing to do.”

“Did you kiss him?”

“We kissed,” I replied.

“Did you like it?” she asked.

“It was nowhere as good as kissing you,” I answered.

“Good answer,” she said with a smile.

Chapter 17 - Meeting Bob’s Parents.

I was surprised when Bob called me a week later. “You’ve been super, and I had a good time on our date. Something has come up, and I’d like to ask you for a favor.”

“Ask away,” I responded, “the worst thing that can happen is that I refuse.”

“You may want to, after you hear what I’m asking,” he continued. “You see, my parents saw the photos of our date, and now they want to meet you, and want me to invite you to a barbeque this Sunday afternoon at my house.”

“I’m going to assume that you want me to look like a girl. So what’s so bad about that?” I asked, “aside from the possibility that I’ll drip barbeque sauce on my rack.”

“Well, my parents are a little intense,” he answered. “You see, they invited some friends and relatives, and they want to show you off as my girlfriend. They are a bit embarrassed that I’m gay. They hope that you being there will show that I’m not gay. I don’t like it, but you can understand that I want them off my case for a while, and you being there could do it. It might not be a lot of fun for you, but you seem to be the kind of person who can handle it.”

“I’ll take that as a compliment,” I said. “I understand your situation, and I’ll do what I can to make your life easier.”

“Thanks a whole bunch,” he said, “I owe you. There’s one other thing. My parents are both professors. My Dad teaches French.”

“Well, then I’ll wow them with my language skills,” I said.

* * *

That Sunday, I took great care in what I wore and my appearance. I had told my Mother and Sisters what was happening, and my Sisters went into high gear.

“What kind of look do you want?” asked Nancy.

“I want to look like an innocent, demure young lady,” I answered.

“Look here, sister,” Emma declared, “we’re good, but we can’t do magic. Demure we can do, but you innocent? No way.” After going through my wardrobe and my Sisters’ wardrobes, we finally decided on a plain white A-line skirt that was about four inches above my knees, a pink frilly blouse with chiffon sleeves and a pair of white tennis shoes.

My Mother observed all of this. “I don’t think it’s nice to deceive Bob’s Parents,” she declared.

“You mean, like you never deceived Dad?” Emma stated.

“That’s different,” Mom said.

“Is that because you’re married to him?” Emma questioned. My Mother gave us a dirty look in response, and then decided to change the topic of discussion.

“You need a white purse,” she said, “I think I have just the purse,” she said, and she went to get the purse.

* * *

When I arrived at Bob’s house, he met me at the door. “You look wonderful,” he said, “all girl. Let me introduce you to my Parents and some of the guests.” There were a lot of guests. “My folks want to show you off to everyone,” he said, “Their idea, not mine.”

Bob’s parents appeared to be glad to meet me. “Enchantee,” Bob’s Father said.

“Merci,” I replied.

“Do you speak French?” he asked, with a hopeful tone in his voice. Speaking in French, I replied that I was taking French in school. He immediately responded with a torrent of French, probably to test my fluency. I understood most of what he said, and I was able to make suitable responses, also in French.

“You seem to be quite fluent,” he said. “I’m impressed.”

Bob’s Mother interrupted, “He’s always happy to meet someone who speaks French. He thinks that it should be a mandatory rule that everyone learn French. He’s disappointed that Bob isn’t that fluent” Bob’s Dad gave her a dirty look, but otherwise ignored the dig.

“Have you ever heard any French songs?” he asked. I admitted that I had. “I recently bought a CD of French cabaret songs. You want to hear it?”

Bob’s Mother interrupted again, “She didn’t come here to listen to that frog music,” she said. Bob’s Dad didn’t like the use of the word ‘frog’ for ‘French.’

I began to get a funny feeling about this CD. Could it be the one I recorded, I wondered?

Bob’s Mother introduced me to all of the relatives and guests as ‘Bob’s girlfriend,’ which I found interesting. While circulating I noticed that they had a Bosendorfer piano.

“That’s a beautiful piano,” I said.

“Do you play?”

“Some,” I answered.

Despite the disparaging remark about ‘frog’ music, Bob’s Dad found the CD and carried it over to me. It indeed was the one I had recently recorded. He looked at the cover picture and at me, and then repeated the same. I could see him making the connection. “Mildred,” he announced, “Bob’s girlfriend is the singer on this CD!”

“How nice,”she absently responded. Then what he had said hit her. “What?” she exclaimed as she snatched the CD from her husband’s hands. Like her husband she repeatedly looked at me and the CD cover. “Well, I must say, you’ve made his day.”

She turned to her husband. “She doesn’t have to hear any of the songs on this CD, she’s heard them millions of times.”

“Would you sing one for us?” Bob’s Dad asked.

“My pleasure,” I responded.

“Hey, everyone,” Bob’s Dad announced as he waved the CD in the air, “Bob’s girlfriend is the singer on this CD, and she’s willing to sing one of the songs for us.”

“How about Parlez-moi D’Amour?” I asked.

“Great choice,” he responded, and I sat down at the piano, smoothing my skirt under me as I did. I played a brief introduction, and then launched into the song. When I finished I stood up and curtseyed to the applause.

A few minutes later Bob came up to me. “I’m really sorry, I didn’t mean for this to happen,” he said.

“That’s alright, no problem,” I responded with a smile.

“You’ve really made Dad’s day,” he commented. “I don’t know what he’ll do when we break up.” We had planned to tell everyone that I had made up with my boyfriend and that Bob and I would not be dating anymore.

Later on, Bob’s Dad took me aside. “How many years of French have you taken?” he asked.

“This is my third year,” I answered.

“Any plans to major in French in college?” he asked.

“Maybe.”

“As you know, I teach French, and your grasp of the language and pronunciation are very good. I would be happy to have you consider going to my school and taking French. You probably would not have to take the introductory courses, but go directly into the advanced courses.”

One song was followed by another, and the barbeque evolved into a musical soiree. As a parting gesture I autographed the CD cover, which greatly pleased Bob’s Dad.

Bob and I were able to find a few minuted to be with each other. “I really want to thank you for all you’ve done. You made a real hit with my Parents, and taken some heat off of me. If you and Sandy weren’t an item, I’d like to date you, since you are a boy.”

“I’m not into that scene, but I’ll take what you said as a compliment,” I responded, “Thank you.”

When I arrived back home, my Mother wanted to know how it went. I related that Bob’s Dad was a professor of French, and that he had my CD, and connected me with the CD. “So, I did a lot of singing,” I said. I met up with Sandy the next day and she wanted to know the same. I gave her the same answer which I gave my Mother.

Later on, I related the events to Mlle. Vert. It turned out that she knew Bob’s Dad. “He thinks that I’m a girl, so please don’t tell him that I’m not,” I asked her.

Chapter 18 - Dad comes around.

It was after a counseling session that my Father and I had a frank talk. “I’m well aware of the fact that you have been sneaking out while dressed as a girl.”

“I wouldn’t say ‘sneaking,’ it’s more like I don’t flaunt my dressing in front of you because I know you don’t like it,” I said.

“I appreciate that you don’t want to cause me discomfort,” he said, “but I feel like you are dressing behind my back.”

“So, what do you want me to do, other than stopping dressing entirely?” I asked.

“Well, I know that there are times when you have to dress as a girl, like when it deals with your CD, but I also know that you also dress as a girl just for the fun of it.” He paused for a few seconds. “I can deal with you dressing as a girl. I don’t like it, but I don’t want to be cut out of parts of your life. What I propose is that you not conceal your dressing from me, with the understanding that I don’t approve, but with the further understanding that I will not forbid you from dressing whenever you wish.”

“I hope what you mean is that I can wear a dress or skirt anytime I’m going out or even when I’m at home in the same room as you,” I said.

“That’s pretty much it,” he responded, “but in doing so, I would like you to refrain from looking like a hooker.”

“I can live with that,” I responded.

“And no prancing around half dressed,” he said.

“Okay, no prancing,” I agreed, with a smile at my own cleverness.

“Wait,” he said, “the important part is not ‘prancing’ but in being half dressed.”

“Okay, nothing that my sisters wouldn’t do,” I assured him.

“Wait a minute,” he said, “you know I don’t have any control over them. Don’t use them as a role model. I’m hoping that you will be more modest.” I had to smile at this comment.

With that we called Mother in and told her what Dad and I had decided. One positive result was that Dad would tell me how nice I looked when dressed even if he didn’t like it. “I love you, and I don’t stop loving you when you wear a dress,” he said.

Chapter 19 - Confusion at Counseling.

I had a private session with Dr. Goodman where I had an opportunity to tell my counselor about my date with Bob, and the reasons. “Did you kiss him?”she asked.

“Yes.”

“Anything more?” she then asked.

“No.”

“Did you enjoy kissing him?” she asked.

“It was okay, but I like kissing Sandy more,” I answered.

“You knew that Bob was gay when you kissed. Do you think that this affected how you felt about kissing him?”

“I’m not sure,” I replied, “it did seem a little gay, and I don’t think that I’m gay.”

“Have you ever thought about dating a straight boy?” she asked

“Not really,” I responded, “I don’t think that Sandy would approve.”

My counselor made some notes. “You don’t have a lot of experience in sexual relationships, which makes it difficult to determine your preferences,” she said. “Have you noticed any physical changes?”

“Not really,” I said.

“Why don’t you and Sandy discuss you going on dates with boys.” she suggested.

Sandy and I discussed my dating boys. She didn’t like the idea at all, even thought my counselor had suggested it. I, of course, didn’t know any boys who would want to date me.

Except for Bill. I ran across him at the mall, when I was dressed. “You look pretty good,” he said, “You want to catch a movie this weekend?”

‘Wow,’ I thought, ‘I’ve just been asked for a date by a boy.’

“Sure,” I answered.

I dressed very carefully for my date. I wanted to favorably impress him. I wore an A-line skirt and blouse. Underneath it, I decided to wear nylons and my corset. While at the movie, I felt him put his arm around me, and I put my head on his shoulder. Then he kissed me. It was wonderful, as good as kissing Sandy. Bill and I continued to date, and I let his hands have a freer range. While I told Sandy about the dates, I didn’t go into great detail, but rather I made it seem like I was only doing it because of what my counselor had suggested. I knew that sooner or later, we would have to go beyond kissing and hugging. That opportunity arose one Sunday afternoon when I was at his house. His parents were not home. He made a suggestion of what we could do. I didn’t want to. I was a boy, not a girl, and that left me with a negative feeling. Because of that and because Sandy did not like my dating Bill, I stopped going out with him.

I related my experiences to my counselor. Rather than reaching any conclusions, it just created more questions. “I don’t think you know what you want to do at this time. I suggest we hold off making any decisions until we get a better idea of what you really want to do,” she said.

Chapter 20 - Another CD.

It was at the end of my junior year at highschool that I received a call from Mr. Phillips, my record producer. “Nicholas and I were discussing you the other day. Your CD went over better than we expected, and we were trying to figure out whether it makes sense to produce another. We may want to change the format somewhat, since I think that the market has enough French cabaret songs.”

“What kind of format are you looking for?” I asked.

“You’ve got a sexy voice, so something that would capitalize on that point. If you’re interested in that, Nicholas and I will scout around for likely music.”

“How about I write my own songs?” I ventured.

“You can do that?” he said, with a strain of disbelief in his voice.

“I’ve done a few, and I think that I can.”

“Then why don’t you see if you can do some more and make a rough tape for us to hear.”

“Okay,” I said.

I spent my free time over the next month working on composing some songs. The music was difficult enough but the lyrics were harder. During this process, I discovered that it made sense to have the lyrics down first, rather than trying to get the lyrics to fit a melody which I had written.

At last I had about 20 songs, some better than others. If I wrote additional verses for some of them I felt that I could fill a CD. Of course, the producers may not like any or all of them. Using a digitizer and some microphones I made up a CD and sent it to them.

As expected, some of the songs were rejected, but Mr. Phillips and Mr. Nicholas liked the others. “We’ll get the rights to some other songs, and we’ll have enough for a CD. The ones you wrote we’ll release as singles. As to the ones we rejected, we’ll put the scores up for sale. Maybe some other singer will want to record them. Naturally, we will copyright all of the songs as well as your singing. We want to hold the copyright, and we will pay you for assigning the rights, independent of how well the songs do on the market.” Mr. Phillips handed me a contract. “Take this to your lawyer and let us know as soon as possible, since we want to start recording in the near future.”

They had suggested that some strings would work well with the songs, and I went back home to write string parts. “If you have problems with the string parts, I know an arranger who can take care of it. In fact, we might want the arranger to work on all of the songs.”

When all of this was done, we started recording. The arrangements were well done, and I had practiced all of the songs at home, so we ended up doing more songs in each session than they had planned. Naturally, both Mr. Phillips and Mr. Nicholas were pleased with this because it reduced the production costs.

When the music was released, Mr. Phillips called Ms. Stone, the critic for the local paper and she interviewed me again. It was later that I found out that our local paper was syndicated, and the interview was published in quite a few papers. This really helped sales. For the second time, I traveled around promoting the CD and giving concerts, not as the headliner, but as a warm up for the main act. This time I took Nancy with me as my manager.

Chapter 21 - Music Video.

My senior year in high school was not particularly notable. Sandy and I continued to date. I took a fourth year of French. I received royalties for my second CD. But there were a few notable exceptions. I was driving in my car and I heard one of my rejected songs being performed. At first I didn’t recognize it, because the singer’s style was so different from mine, however, her style suited what I had written.

One day Mr. Phillips called. “I’ve had some inquiries about you writing additional songs. I think you need an agent to handle this.” Our family lawyer knew some agents, and soon I was connected with one. One of the first things my agent did was to suggest making a music video.

Mr. Nicholas agreed to front the cost of producing the video, provided that he and Mr. Phillips could tell me what to wear. “We want something sexy. This is the entertainment business, so we don’t want to hear anything about only being a sex object. Just face the fact that if you look sexy, the more both of us make on the video.”

“How about the dress I wore before?”

“You looked good, but we are thinking about something slinky with a slit that will allow you to show some leg.”

“Who pays for it?” I wanted to know.

“We’ll rent it, so we’ll pay,” Mr. Nicholas answered, “I want you to go to this shop, and ask for Margie. She knows what we want,” and with that he handed me a card from the shop.

My sisters were really interested in this. “If you’re going to show some leg, you might want to consider stockings and garters, rather than pantyhose,” Nancy advised.

I called the shop and made an appointment to meet with Margie and gave her my sizes and measurements. The day before going to the shop, I visited the beauty salon. “It has to look sexy,” I told Sally, and sexy was what I got. I spent a lot of time getting dressed and applying my makeup.

When I went to the shop Margie had selected some dresses for me to try on. “All you have to do is put them on. Mr. Nicholas said that I was to chose which one you will wear.” All of the dresses were revealing and all had a slit to show off a leg. When she made her decision, she said, “You know the color, so select your hose to go with it.”

Mr. Nicholas and I arranged the date for the shooting of the video. When this was done he said, “Don’t worry about your makeup and hair. I’ll hire a makeup girl and a hairdresser for the session, in addition to Margie. I’ll also hire some studio musicians to accompany you, since you’ll be busy strutting your stuff and singing.”

On the day for the video, Nancy went with me, even though my other sisters wanted to go. I wore stockings, not pantyhose, and everything that would go with the dress which Margie had selected.

We arrived before everyone else. Someone had set up the area for the video, with a backdrop. The studio provided a director, who went over what I should do and where. We then practiced the songs and the director made some changes in what I was to do. By the time we were finished Margie, the makeup artist, and the hairdresser had arrived. “The rest of the people will be here in forty-five minutes. See if you can have her ready by then.” When I had my costume and makeup on and my hair fixed, the musicians and the video crew were there. I ran through everything, and some changes were made in the lighting. Then the actual shooting began. While the director was pleased with the first take, we did some additional ones, just to be sure. After that I took off the dress and gave it back to Margie.

I was pleased when the video was released and I saw some of my classmates watching it on their tablets and cell phones. No one connected me, as Eugene, with the girl in the music video.

No answers yet.

Gene or Jean? - Part 5 - The Halloqueen

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Contests, Deals, Bets or Dares
  • Voluntary

TG Elements: 

  • Corsets
  • Halloween

Other Keywords: 

  • Sorority

Permission: 

  • Posted by author(s)

Gene or Jean? - Part V - The Halloqueen.
By Pentatonic

Chapter 22 - Sylvia.

At last I graduated, and was heading off to college, to major in French Literature with a minor in Business. I figured that I would not be cross-dressing while in college, so I left all of my feminine attire at home. I figured wrong.

Sandy also graduated. However, she was enrolled at a different college. This put a strain on our relationship which shortly resulted in her connecting with a boy at her college. When she broke the news to me, she pointed out that her new boyfriend did not like to wear women’s clothes. I was hurt, but because she broke up with me, I hoped that she wasn’t also hurt. Oh, well. As a result I was in the market for a new girlfriend. I was still considered to be a slightly nerdly boy who was slightly feminine. Not good for finding a girl friend.

I was now only occasionally seeing my counselor. What was new were the dynamics of my relationships. She asked me if I wanted to be a girl, full time. While the thought had some good points to it, I just wasn’t sure.

After breaking up with Sandy and a while at college, I met Sylvia. I was at the student union, and went into the cafeteria for lunch. As expected, the place was crowded, and I wandered around looking for an empty seat. There was an empty seat at a table across from this girl. She looked up from her tablet and, taking off her ear buds, invited me to sit down. She then returned to looking at her tablet. I asked her what she was watching. “It’s a new music video of this fantastic girl singer,” she replied. “Oh?” I said, and she showed me what was on her laptop. It was me. Of course, I was wearing my boy clothes, and she didn’t make the connection. When the music video was over she put down her tablet. “Did you ever watch this video?” she asked.

“Yeah,” I replied, “a few times.”

“Isn’t it fantastic?” she said, “I’d love to attend one of her concerts. How about you?”

I admitted that it would be nice, omitting that if there was such a concert, I would have to be on stage, wearing a dress.

We seemed to get along with each other and chatted for about a half an hour, until we both had classes.

I had her name and her telephone number, so I called her and asked if she wanted to meet at the cafeteria again. She did.

“So, what is your major?” she asked.

“French Literature with a Business minor,” I replied. “How about you?”

“Sociology,” she said, “so you must have studied French in high school,” she added.

“All four years,” I replied.

“I took two years of French in high school, and I’m taking French here to satisfy my foreign language requirement,” she volunteered. “Maybe you could help me with my French?”

“I’d be happy to,” I responded.

“You know, when we first met, I was watching this music video.” she said. “The girl in that video also did a whole CD of French cabaret songs. Did you know that?”

“Yeah,” I responded.

“Did you like it?” she then asked.

“As a matter of fact, I did,” I said, breaking away from one word answers.

“My French prof played two of the songs in class,” she said. “My prof said that the pronunciation was good, but with a slight French-Canadian accent. He said that as second year students we probably wouldn’t be able to recognize it. Did you?”

“I heard that. Since I have an Aunt who grew up outside of Montreal, and who now lives in the same town where I live, I practiced French with her. She has a slight Canadian accent, or so I’m told, so I also have that accent,” I said.

“I live in an apartment with three other students,” she said, “how about you?”

“I live in a dorm room with a jock on an athletic scholarship,” I answered. “He considers French to be a sissy language. Naturally, we don’t get along.”

“I’ve got an idea,” she said, “Why don’t you come over to my place and translate the lyrics of the songs for me?” It appeared that the translation was part of her homework.

“I can do that,” I replied, “when and where?” She told me her address and suggested Sunday, about two. She gave me her last name, so I could locate the correct apartment.

“All of my roomies are from my town, which is how I found the place,” she told me. “One is a sophomore psychology student. Another is a junior and is studying to become a teacher. The other, a senior, seems to be majoring in boys. She goes out a lot and I never see her study,” she said with a smile at her own humor. I smiled back.

On Sunday I eschewed student grunge and wore slacks and a shirt with a collar. When I knocked on the door to Sylvia’s apartment, a good looking redhead answered the door. “Hey Sylvia,” she announced, “Frenchy is here!” and she asked me in.

Sylvia came into the front room. She was wearing a cute pair of tan shorts and a pink T-shirt top. She had sandals on her feet. She looked wonderful. “You have to excuse Ann,”she said, “she probably forgot your name. Have a seat.” She then went into another room and returned with the CD of cabaret songs.

It appeared that Ann was the senior who, as Sylvia said, was majoring in boys. Sylvia put the CD in a player, and Ann grabbed the jewel box. I could see her scrutinizing my photo on the cover. I was getting nervous, but before anything could happen the first song started. I translated as the music played.

“You did that pretty quickly,” Ann observed, “Either you’re faking it, or you’ve done this before.”

“I translated all of the songs into English for an assignment in high school, so I know it,” I responded.

“The translation is for a class assignment due tomorrow,” Sylvia confessed.

“Then you should do your own translation,” I warned her, “As I told you, I’ve had four years of French in high school, so some of my translation might have a nuance which you are not expected to know as a second year. Which two songs have you chosen?”

“Plaisir D’Amour and Parlez-Moi D’Amour,”she said.

“Good choices,” I said, “I like both of those songs.”

We went into the kitchen and sat at the table, and Sylvia began to translate. I only corrected obvious mistakes. Sylvia called me a few days later and gleefully reported that she received one of only two ‘A’s’ on the translation. “You’re my good luck charm,” she said, “Will you help me out in the future?”

“With pleasure,” I responded. So we established a routine where I would tutor her on Sunday afternoons. Occasionally I would bring some of the materials which I was studying to see if she could follow along. Sometimes she could and sometimes she couldn’t. Our study sessions expanded into occasional dates.

Thus the tutoring sessions blossomed into a relationship, and I spent more and more time with her.

Chapter 23 - Halloween and becoming the ‘Halloqueen.’

It was in mid-October that Ann announced that her sorority, Sigma Rho Sigma or SRS, was sponsoring a Halloween party. All students were invited to attend because it was a fund-raiser. Sylvia made it plain that she wanted to go with me.

“But I don’t have a costume, and I’m a little short on funds right now, so I can’t buy or rent one,” I explained. “I only have enough to pay the admission price.”

“You have to be in costume to get in,” Ann explained, “Maybe we can come up with something.”

“Sue,” Ann announced, “can you come in here for a minute. Gene needs a costume for the SRS Halloween party. Do you still have that floor length formal gown you wore to the dance last spring?”

Ann then turned to me. “Think that you’re man enough to wear a dress in public?” she asked. Now that was unique, I thought. I had always associated wearing a dress to be feminine.

I knew that I would go for it. I hadn’t worn female clothes since summer. In fact, I didn’t bring any with me to college. I was sure that my roommate would not approve. I wanted to wear the dress, but I had to make it look like I was somewhat reluctant. I had no problems with dressing.

“I don’t know,” I began, “but I suppose I’m enough of a man to do so.”

“Good,” Ann said. “Sue, bring the dress in here, please.”

Sue returned with a long garment bag. “I don’t know if it will fit. I had to wear a waist nipper with it.” She held up a dark green floor length gown.

“Do you have the waist nipper?” Ann asked.

“Yeah,” Sue responded, “It’s in the garment bag.”

Ann turned to me. “I don’t suppose you know what dress size you would wear?” she said. “No, of course you wouldn’t,” she said, answering her own question. I certainly knew my dress size, but I had no desire to question what she said and let on that I cross-dressed. However, I really wanted to wear that dress.

Sue was a bit on the chunky side. Ann looked at the size on the label and looked at me. “I think this will work,” she said. She held the dress up to me. It was then that I noticed that it had a slit up the left side of the skirt, well above mid-thigh.

“Okay, let’s see if he can get into it.” Ann announced. She then turned to me and said, “strip down to your underwear.”

The waist nipper was pinned to the hanger. “Sue, give me that waist nipper,” Ann said. She handed it to me. “Here, put this on,” she commanded. I knew how to put it on, but pretended confusion. Finally, Ann helped me put it on. It did it’s job and my waist shrank, pushing my flesh upward. “Looking good,” Ann commented.

Ann turned to Sylvia. “You’ve been awfully quiet. Here, help me put this dress on him.” Sylvia and Ann put the dress over my head, and let it slip over my body. After doing this, Sylvia zipped it up. Both Ann and Sylvia stepped back to view their handiwork.

“It fits perfectly,” Sylvia commented.

I just fidgeted a bit, and examined the slit. “Is this necessary?” I questioned.

“It makes you look sexy,” Ann responded, “All girls want to look sexy.”

“But I’m not a girl,” I complained, insincerely. Ann and Sylvia ignored what I had said.

“Now let’s see about shoes,” Ann commented. “Let’s see what we have. Here, sit down,” she commanded.

Force of habit caused me to smooth the back of the dress as I sat down on the front of a chair, my knees together and my back straight. I noticed that Ann was studying this but she said nothing. I knew my shoe size, but didn’t volunteer that information. After trying on several pairs, one pair was found that wasn’t too tight.

“Stand up, and let me see you walk in heels,” Ann commanded. I certainly knew how to walk in heels, but I did my best to totter a bit as I walked. “They’ll do,” Ann declared.

“Okay, girls,” Ann added, “let’s make a list of what else we need. Panty hose or stockings and garter belt?”

“I wore panty hose,” Sue said, “If he wears stockings, some bare thigh will be visible.”

“Even the better,” Ann said with an evil grin. “What do you think, Sylvia?”

“Stockings and garter belt,” Sylvia replied with a grin, “ I kind of like a sexy, slightly naughty look.”

“Okay, black garter belt and stockings,” Ann continued, as she made notes on a piece of paper. “Panties,” she said, “we can’t forget panties. Black and brief.” She looked at Sylvia and Sue for confirmation. “Maybe a short black half slip with a matching slit. Do you have one, Sue?” Sue acknowledged that she had just the right slip.

“Okay, now for the top, she said, “He’ll need a black bra, and maybe a black camisole. We’ll see what we have in the apartment, and see what fits.”

She made a few further notes. “Okay, Frenchy, you can take the dress off,” she said. They unzipped the dress and helped me take it off.

“What are we going to do about his hair,” Sue asked.

“Pulled back with some pulled behind his ears, a head band, and the rest with a curl at the end,” Sue suggested.

“Or maybe a french twist,” suggested Sylvia, “something sophisticated.”

By now I had all of my clothes back on. Ann was studying my face. “Did anyone ever tell you that you have a cute face, almost too cute for a boy?”

“No,” I lied.

“Well you do,” commented Ann. “With a little makeup and doing something about his hair, we could walk him all around campus, and everyone would think he was a girl. You want to try?” she asked me.

“Definitely not!” I asserted, knowing full well that she was correct.

The next few days consisted of a crash course in acting and moving like a girl, which I really didn’t need. It also consisted of learning how to dance as a girl, which I did need.

One might ask why I let a bunch of girls get me to dress up as a girl. First, I really liked Sylvia, and she seemed to favor the idea; second, it was Halloween, the cross-dressers’ holiday and; third, I wanted to dress up, I liked doing it.

I was blissfully unaware of the possible consequences.

* * *

On the day of the Halloween party, Sylvia and her roommates all joined in for my transformation. Sylvia did my hair and Sue my makeup, all under Ann’s supervision. With my hair and makeup done, Sylvia, Sue and Rachael, the other roommate, went to collect the other clothes, leaving me alone with Ann. “You’ve done this before, haven’t you?” she asked. I noticed that she was holding my CD of cabaret songs, with my picture on it. I knew that I looked a lot like the picture.

“Yes.” I admitted, “but please don’t tell anyone.”

“This is you on the cover,” she said.

“Yes,” I further admitted.

“And you sang the songs on the CD, didn’t you?” Again I had to admit it was true.

“Why don’t you want Sylvia to know?” she asked.

“Because I like her, and want to continue our relationship,” I responded, “if she knew that I cross-dressed, she might drop me like a hot potato.”

“But then again, she might not.”

At this time, Sylvia, Sue and Rachael returned with the clothes I was to wear to the party. I started to undress, assuming that the girls would leave the room, giving me some privacy. I assumed wrong. No one moved.

“How about some privacy,” I requested, which the girls intentionally misunderstood.

“Ann, Sue, do you need privacy?”Sylvia asked.

“Not us,” Ann replied for herself and Sue, intentionally misunderstanding my request.

“Rachael, Sylvia, do you need privacy?” Ann asked in turn.

“No, we’re fine,” Rachael answered for herself and Sylvia.

“None of us need privacy,” Sylvia said to me.

“Not for you, for me,” I said with frustration edging into my voice. All four of the girls started laughing at their own joke, but none of them made any indication of leaving the room.

“Okay, so be it!” I declared, took the panties, faced the wall, took off my pants and underpants, and slid on the panties. It was some time since I had last worn panties, and I savored the feeling they gave me. I then took off my shirt and undershirt, and turned around to face the girls. I had used a hair remover the night before and my skin was smooth and hairless. I put on the waist nipper and Sylvia helped me with the bra, not that I really needed any help. I put on the garter belt, and fished the suspender straps under the panties. Ann gave me a knowing smile when she saw me do this.

I sat down and started to put on the stockings when Sylvia said, “Let me help you with that.” Her help included rubbing her hands up and down my legs. She then fastened the straps of the garter belt to the stockings.

Sue handed me the half slip, and said, “The slit goes on your left side,” as if I didn’t know. Rachael slid the camisole over my head, while Ann balled up some pantyhose to stuff into the bra.

At last it was time for the gown. All of the girls assisted putting it on me, and pulling it so it hung correctly. Rachael then knelt on the floor and put on my shoes.

“Nail polish,” Ann announced, an produced a bottle of red polish. “It matches your lipstick,” she said. All the while I could feel Sylvia rubbing my butt. The last step was packing a purse.

Sylvia and Ann then completed getting ready, and Sue handed me a coat. Ann, Sylvia and I then stepped outside. A breeze lifted up the skirt of the gown, opening the slit. I could feel the cold air on my left leg.

I sat down on the rear seat and turned as a lady would do when getting in a car wearing a dress. This was not lost on either Ann or Sylvia. Sylvia then got into the back seat with me, to my left. Ann was sitting alone in the front seat. Once we were all seated, we fastened our seat belts. Sylvia took the middle of the back seat, and with an innocent look on her face, found the slit in my dress and ran her hand up and down my left leg.

* * *

The sorority had rented a hall off campus, and it was appropriately decorated for Halloween. I paid for Sylvia’s and my admission and hung up our coats. The main room was fairly large, with tables and chairs around the outer edge. There was a small stage at the far end, with only a piano on it. Because this was off-campus, there were two bars, one for over 21 and one for under 21. Two of the sorority members were checking ID’s. Those over 21 were given orange and black wrist bands. which allowed them to buy alcoholic drinks. Both bars were busy when we walked in. Ann introduced us to some of the sorority members and then left us on our own.

All of the sorority members wore name tags. The Halloween party was part of the rush to get new members. Ann had hoped that Sylvia would join her sorority and Sylvia and I were seated at a table with some sorority members.

I sat to Sylvia’s right, probably to give her access to the slit in my dress. To my right was a sorority member named Tiffany. Tiffany obviously though that I was a girl, and began talking about the advantages of joining the sorority.

“That sounds great,” I told Tiffany, “but I can’t join.”

“Why not?” she asked.

“Because I’m not a girl,” I replied. When I said that, she looked at me in total astonishment.

“But you look like a girl.”

“It’s my Halloween costume,” I said.

While we talked I could feel that Sylvia’s right hand had found the slit in my dress, and was rubbing my stockinged leg. While that was pleasant, I was afraid I’d get aroused.

I noticed that there were a lot of boys milling around, checking out the girls. Two of them came up to Sylvia and me and asked us if we wanted to dance. “Sure,” Sylvia answered for both of us. “Come on Jean, let’s dance.” I had no choice but to comply. Tiffany heard this exchange and gave me a strange look as I stood up and the boy took my hand.

“I’m Fred,” he said, “and from what your friend said, you must be Jean.” The music was loud enough to make conversation difficult until the DJ put on a slow dance song. Then Fred said, “You’re a good dancer. What is it about you girls, most of you are good dancers.”

“I have three sisters, and we all taught each other how to dance,” I responded.

When Sylvia and I returned to the table, Ann was sitting where Tiffany had sat. “It looks like you scared poor Tiff away. What did you do?”

“She was trying to get me to join Sigma Rho Sigma until I told her that I wasn’t a girl. I probably should have just gone along with her.”

“She probably has it in for you,” Ann said. “We have a little contest that we do every year, where we pick a Halloqueen. She’ll probably make sure that you’re one of the contestants.”

“But I’m a boy, I can’t be Halloween queen, or Halloqueen as you put it.”

“That never stopped anyone in prior years,” Ann commented, “I actually think that you have a good chance of winning. By the way, part of the contest is a talent contest. You shouldn’t have a problem with that,” she added with a chuckle.

As the evening progresses, I found that Sylvia couldn’t keep her hands off of me when we were not dancing.

About ten, the DJ announced, “After I take a break, we’ll start the Halloqueen contests. The ladies of the sorority have picked the contestants, and will now escort them to the stage.” With that the sorority sisters fanned out to bring the contestants to the stage. You didn’t know you were a contestant until one of the sorority sisters brought you to the stage. I remembered what Ann had said, as I noted that Tiffany made a bee line toward me. With a wicked smile on her face, she pulled me toward the stage. She had to let me go when we got to the steps leading up to the stage, but she and some other sorority sisters blocked any avenue of escape except up the steps. I lifted my skirt and climbed up the stairs, followed by Tiffany.

Once on the stage she said, “You have a handy slit in your skirt. Show them some leg.” I moved my left leg out of the slit. I noted that everyone could see my stocking tops. This was greeted with wolf whistles. I blushed.

There were twelve contestants on the stage, both boys and girls, with a variety of costumes. One girl, who was the President of Sigma Rho Sigma had a microphone. She introduced herself and gave out the rules of the contest. “There are twelve of us, each with a poster board with the number one through twelve. One of these girls will stand behind each contestant in random order. No contestant will know their number. One by one on my command, a sister will turn her poster board so the number is visible. You are to clap or otherwise make noise when a contestant’s number is shown. The four contestants with the loudest response will move into the final phase, and yes, you may vote as many times as you wish.”

And so the selection began. The numbers were called in random order. Some contestants received only a little applause, but for others the response was deafening.

“That was for a warmup,” she said, “We will do it several times more to be sure that we have the correct finalists.” She turned to the contestants, and said, “This is supposed to be fun. Let’s see some big smiles.” I complied and flashed a big smile with my red lipsticked lips. With that, the contest commenced.

“Now for the elimination. I will call out the numbers of the contestants who have been eliminated. One of our sorority sisters will guide that contestant center stage, and he or she will give us his or her name and tell us where he or she is from. After that, he or she may leave the stage.”

Eight of the contestants were eliminated. I was not one of them. “Let’s hear it for our contestants who were eliminated. You were all good sports.”

After the last eliminated contestant had left the stage, she said, “Okay, these are our four finalists. I want each of you to walk back and forth on the stage and strut your stuff.”

“You in the audience are encouraged to yell, cheer, whistle or clap,” she told the audience. The noise was deafening as each of us strutted across the stage. It appeared it was louder as I did it.

The President of SRS then pointed at me. “Let’s see some leg, honey,” she commanded.

What the heck, I thought, and I lifted the hem of my skirt, and stuck my left leg out to a tumultuous response. My stocking top and garter straps were clearly visible, along with some thigh. I looked at the other finalists. Three of us were boys in drag. The fourth was a foxy looking girl in a brief and sexy witch costume.

“For obvious reasons, we can’t have a swimsuit competition, but we can have a talent competition.” She turned to the audience, and said, “None of our finalists have had a chance to prepare for this portion of the contest, so the results may be interesting.” She smirked as she said this.

The first finalist was the girl in the witch costume. “And what are you going to do?” the President asked.

“I could dance, but I need music.”

“What song?”

“Theme from New York, New York.”

“We may have to wait until the DJ comes back, unless we have a volunteer to play the piano,” the President said.

I raised my hand. “I’ll do it,” I said, and walked to the piano. I smoothed my skirt under me and sat down. “When ever you’re ready,” I said. The girl nodded and I started to play. She was really good. I hoped she’d win.

When the girl was finished, there was thunderous applause. The President turned to me and said, “Thank you for playing the piano, but don’t think that it satisfied your part of the talent contest,”

The other two finalists each elected to sing a song, and again I volunteered to accompany them on the piano. One was okay, but the other one couldn’t keep in tune and went flat.

Finally, the President turned to me. “Introduce yourself and tell us what you are going to do.”

“My name is Gene, and I’m going to sing a French cabaret song called ‘Parlez-moi D’Amour,’ which means ‘speak to me of love.’ Because it is a French song, I will sing in it French. I will also accompany myself on the piano.”

So I gracefully sat at the piano and turned my face to the audience, and began. When I finished, there was dead silence at first, then some clapping, and then a thunderous response. I stood up and curtsied. This brought an even greater response.

By this time the DJ had returned, and he played the same song from my CD. When that was finished, the President held up her hand for silence and said, “You did a great job of imitating what the DJ played. Have you heard the recording before?”

“Yes, many times,” I answered.

With that I was allowed to leave the stage and return to the table. Sylvia gave me a big hug with one hand on my butt. “You really knocked them out.”

The sorority President then announced that the panel of judges would meet and pick the new Halloqueen for the year.

“I’m sure that you will win,” Sylvia said.

I did, and was called back to the stage receive an orange sash with ‘SRS Halloqueen’ on it and to have a tiara placed on my head, supposedly by last year’s Halloqueen, who was a boy wearing a long dress.

As I was walking back to the table, Tiffany intercepted me. “Being Halloqueen is a year-long event,” she said with a wicked grin. “It looks like you’ll have to buy some skirts and dresses, that is, unless you already have a stash of them.”

Back at the table I asked Ann what this year long event as SRS Halloqueen was all about. “Let’s see, you crown next year’s Halloqueen, but you figured that out already. If the Halloqueen is a girl she is asked to join our sorority and we waive the first year’s dues. Since you are a boy, you are made an honorary member of our sorority.”

“Is that it?” I asked with a feeling of relief.

“Not quite,” Ann continued. “Our sorority participates in all of the school events, and you will be with the girls as our honored Halloqueen, This includes riding on our float in the homecoming parade, leading the first dance at dances, attending the winter carnival, valentine’s day, spring fling, and stuff like that. We’ll tell you when and what, as needed. Oh, you will be our queen at any sorority events for our members, except for chapter meetings.”

I didn’t like the way this sounded. “What’s this about skirts and dresses? Tiffany told me I would have to buy some skirts and dresses.”

“Oh, when you attend these events, you will wear a skirt or dress as the occasion warrants.”

“What if I just refuse?”

“Aside from proving that you have no school spirit, you go on all of the sororitys’ black list, which means that none of the sisters will go out with you. Come on, it’s a lot of fun, so don’t be a spoil sport.”

She then moved closer to me and whispered, “After watching you get dressed today, and how you walked and acted this evening, I’d be willing to bet that you like to wear girls’ clothes, not to mention that you are wearing hose and a garter belt. Most guys wouldn’t stand for that. I’m also willing to bet that you already have a wardrobe.”

I didn’t respond.

“Since you don’t deny it, I’ll take that as a yes.” she said with a grin.

As we were leaving, Sue asked me if I wanted them to drop me off at my dorm.

“Heavens no!” I emphatically responded, “my roommate is a jock and I can’t let him see me like this.” Accordingly we all went back to the girls’ apartment.

Sylvia offered to help me change back into my boy clothes. While she was doing that, I felt her hands roaming over my body. Every few moments she kissed me. “Seeing you in a dress really turns me on. Just you, not anyone else.”

When I returned to my dorm room, my roommate wasn’t there, and I quickly undressed and climbed into bed.

Chapter - A Visit Home.

The next morning I decided to drive back home and pick up some of my female wardrobe, and I asked Sylvia if she wanted to go with me for company. “Sure,” she replied, “When do you want to head out?”

On the ride, I mentioned that the dorm rooms were kind of crowded, without a lot of room to put things. “So tell me,” she asked, “what are you picking up?”

“Stuff,” I replied.

“What kind of stuff?”

“Just stuff.”

This didn’t satisfy her, so she said, “Ann mentioned that she thinks that you like to dress as a girl and that you have some female clothes. Is that it?”

“Sorta,” I vaguely answered.

I introduced Sylvia to my parents, and went into the basement to get some boxes. When I came back up I asked my mother if she had an extra garment bag.

“Let me get it,” she said, and when she handed it to me she whispered, “for some of your girl stuff?”

“Yeah,” I replied and then told her about being crowned ‘Halloqueen,’ and why I needed the clothes. “Maybe it’s best if we didn’t tell Dad.” I added in a whisper.

Sylvia went to my room with me. She was delightfully amazed at the number of skirts, dresses, blouses and the lingerie I had, not to mention shoes. With her help I packed up a reasonable wardrobe, including the corset. When we were done, we sat on the bed and I related what happened in French class and everything thereafter, including the recordings I made. I also mentioned that I wrote songs, and since there was no piano available, I was taking a keyboard and headphones back with me. After an early supper, Sylvia asked me to bring my CD’s with me and we left.

I knew that I could not keep my girl clothes in my dorm room. My roommate would not understand. Therefore, I squeezed my clothes into Sylvia’s closet and dresser. “We’re about the same size, so I’m going to love borrowing some of your clothes.” I did leave the keyboard in my dorm room.

When Ann, Sue and Rachael were back, Sylvia made me tell them about the CD’s which I had made, and I explained how it contributed to my cross-dressing.

Chapter 34 - Homecoming.

A week later, Ann mentioned that I, as Halloqueen, was riding on the Sigma Rho Sigma float at the homecoming parade. “We have to find something appropriate for you to wear. It’s my guess that the thrift store has a collection of prom dresses, and maybe we can find one there.”

If I was looking for a dress, I decided that I should look like a girl, and with Sylvia’s help I picked a plaid kilt and cream colored blouse. I decided that a corset was necessary, and after I put on my panties and pantyhose, I put on the corset. There was no lack of volunteers to help tighten the laces. I put on the skirt and blouse, and started on my makeup. That I was able to do it so quickly and well amazed the girls. I then fixed my hair with a headband. I grabbed a coat and I was ready to go. Sylvia insisted that she and Ann go with me, Ann being a representative of the sorority upon whose float I would be riding, wearing the dress we hoped to find.

When at the thrift store, I noticed that most of the prom dresses were either worse for wear or an inappropriate style. Sylvia then spotted a floor length white gown, which was my size. It almost looked like a bride’s dress. I noted, thankfully, that it did not have any slits. While I had it on, we looked for a white or cream coat, since it was likely to be cold on the day of the homecoming game and parade. After buying the dress and coat, we went to a shoe outlet and found a pair of white shoes with two inch heels.

After this, Ann said, “Gloves, she needs some white gloves, maybe with white lace trim.”

“How about a full slip, or something to make the skirt of her gown puff out a bit?” suggested Sylvia. “It would help her hips look bigger.” It should be noted that I didn’t object to their use of the feminine pronoun; in fact I kind of liked it.

When we arrived back at the apartment, the first thing I did was to order a pizza to be delivered, after which Sylvia and I put away my purchase. We returned to the living room and chatted with Ann for a while. “I’m so glad that you’re getting into the spirit of things,” Ann commented.

Sylvia sat close to me on the couch, and alternatively rubbed my knee and fiddled with the hem of my kilt. Ann noticed this and announced that she was going to her room to rest and said, “Call me when the pizza is here, and you two, try to behave.”

Sylvia tried to behave but failed miserably. As soon as Ann left the room, Sylvia said. “Seeing you dressed like this turns me on,” and with this she grabbed hold of me and put her lips on mine. I could feel her tongue on my lips and I opened them up to her tongue. From then on, our hugging and touching just got more bold. Finally the pizza arrived and we called this fact out to Ann.

When Ann returned to the living room she had to notice that both Sylvia and I were both a little flushed in the face, our lipsticks were smeared beyond all recognition, and our clothes were disheveled. “I thought I told you two to behave,” she said with a huge grin, “but it’s obvious you ignored me.”

“You told us to behave. You didn’t say whether we should behave well or badly, so we didn’t ignore you,” Sylvia retorted with a smile.

“You two are impossible.”

On Homecoming day we were told to assemble at the stadium parking lot at ten. I knew it would take me some time to get ready, so I slept on the couch at the girls’ apartment. As I was ready to enter the bathroom to change into my pajamas, Sylvia stopped me. “No, that won’t do,” she said, and then added, “wait here for a minute.”

When she came back, she took my pajamas from my hand and handed me a long white nightgown and matching peignoir. “This’ll get you in the proper frame of mind for tomorrow.” She then moved closer to me and whispered, “I wish I had a double bed,” with the innuendo unsaid.

There was nothing to do but to go into the bathroom and put on the nightgown and peignoir, and go to the couch.

I awoke early, before the girls were out of bed, and went into the bathroom to use a hair remover on my body. When this was done I gave myself a close shave, and put on my panties and bra, covered by a robe. By this time the girls were finally up. I went into the living room to allow them to use the bathroom. I then put on the corset and slipped the breast forms into the cups. I tightened the laces as well as I could, and put on my pantyhose. Rachael walked into the living room with her morning coffee. “Would you like some coffee?” she asked. I nodded my head, and she went back into the kitchen. When she returned, I asked her to tighten the laces of my corset, which she gladly did.

After this I put on my full slip and my shoes. I waited until all of the girls were in the living room, because I wanted some help with the dress. Ann and Sylvia helped me with the dress. At this point the girls left the room to get themselves ready. I returned to the now vacant bathroom and applied my makeup, a little heavier than usual. I called to Sylvia and she helped me with a sophisticated up style for my hair. This I followed with some jewelry, the tiara and the sash.

It wasn’t much later that the girls themselves were ready, and at a quarter of ten we put on our coats and left the apartment. My gown was long enough that I had to pick up the hem when I negotiated stairs.

The stadium was not far away, and we arrived about a minute before ten. One of the sorority girls had a big urn of coffee and some doughnuts. The sorority President came up to me. “You look outstanding,” she said, “Much better than I expected.”

“As Halloqueen, I wanted to do it right, and not give the sorority a bad name,” I replied.

“We all appreciate it. By the way, have you met your court who will be riding with you on the float?” and with that she introduced them. They were all wearing formal dresses, and looked really nice.

Tiffany then came up to me. “Nice gown,” she said, “did you have it already or did you have to buy it?” she said making reference with a catty remark she had made to me at the Halloween party.

“I bought it at the thrift store, just for this occasion,” I said,

The President heard this, and said, “Lay off of her. We are overjoyed that she is in the spirit of things, and took the time to look really pretty.”

When the time came, my court and I climbed onto the float. I would have liked to say ‘gracefully climbed’ but it was impossible to be graceful. My ‘throne’ was a white plastic lawn chair perched on the highest part of the float. There were other chairs, a little lower, for the court.

The parade path wound around the campus and part of the town. We were scheduled to arrive back at the stadium shortly before game time, and would make one circuit on the track inside of the stadium for the crowd. I felt like a queen, waving my gloved hand at the people along the parade route and in the stadium. Once outside the stadium we climbed down from the float, exposing a lot of lingerie in the process. There was a portion of the stands reserved for us, near the end zone, and thankfully near some restrooms.

I like football, even if I am way too small to play it. I enjoyed the game, even if our team lost. The sorority had planned a reception in the chapter rooms for parents and alumnae. During the reception a girl who had graduated two years ago came up to me. “I see that you were chosen to be the Halloqueen this year. I can see why you were chosen, you’re a really pretty girl.” Tiffany, who was close by overheard our conversation and just had to interject, “He’s not a girl.” The sorority President overheard this and glared at Tiffany, and moved her away.

“Not one of your fans, is she?” the girl asked.

“Hardly,” I responded.

“But tell me, are you really a boy? I know that boys have been crowned Halloqueen in the past.”

“Tiffany is right,” I responded, “I’m really a boy.”

“But you look so feminine,” she said, “I was going to ask if you were going to pledge this sorority, but I guess the answer is that you can’t. Too bad.”

“My girlfriend is going to pledge, and for this year I’m an honorary member, I said.”

“I’m Diane,” she said as an introduction, “and you are?”

“Gene, short for Eugene, but on days like this I spell it ‘Jean’,”

“You’ve got me interested, can we sit down and talk for a few minutes?”

“Sure,” I answered and we moved to some vacant chairs.

I had mastered sitting gracefully in this dress, and when Diane saw this she said, “You really know how to sit in that dress.”

A moment later she said, “Do you feel humiliated having to wear a dress?”

“Hardly, first of all, a lot of people have seen me in a dress and know that I’m really a boy. I have not received a great deal of grief about it. Second, I like wearing a dress and my girlfriend likes it when I’m dressed.”

I then related my cross-dressing starting with my project in French class, and going through making the CD’s, after which I circulated around the room.

When we were back at the apartment, I asked Ann, “What’s with Tiffany? every chance she get, she gives me a hard time?”

“Don’t tell anyone, but she’s on academic probation, and if she doesn’t pull up her grade point she’ll be out of here,” Ann said, “and from what I’ve heard it doesn’t look like she’ll make it.”

At this point I wanted to change clothes and get out of that blasted corset.

Chapter 35 - The Holidays.

Silvia’s parents, for some reason, couldn’t pick her up for Thanksgiving, and I volunteered to give her a ride back and forth. Fortunately, this detour only added an hour to my drive home. Classes for Wednesday afternoon were cancelled, and Sylvia and I were able to get underway before noon.

When we arrived at Sylvia’s house, her Mother fixed us a late lunch, and we chatted for a while with her parents, all the time with her Mother ‘checking me out.’ I guess I passed the test, because her Mother gave me a hug when I left.

When I arrived at my house, the first thing I noticed was a huge banner which said, “Welcome Home, Halloqueen.” After supper, my sisters cornered me and demanded details of my reign so far as Halloqueen, especially my experiences of being hit upon by boys.

“It’s too bad that you’ll have to stop being Halloqueen next Halloween,” Gloria said, “and no more dresses.”

“Don’t be too sure of that,” rejoined Nancy, “I bet that this is just the beginning.”

They were able to extract some information about Sylvia. “Does she object to you wearing a dress?” Emma asked.

I should have only said that she didn’t mind, but to my regret I admitted that she was turned on when I wore a dress or a skirt. As could be expected, they cross-examined me about this interesting fact. Each question was more risque that the prior one.

“So,” stated Emma, “whenever you want some, all you have to do is put on a skirt. How convenient.”

“That’s not how it is,” I rejoined, “you make it sound so dirty.”

“Well,” she responded, “if you’re wearing a skirt, it gives her easier access. I’m well aware of how this happens, based upon personal experience.”

“Enough!” I stated, “you’re telling me more that I want to know.”

When it was time for bed, Emma handed me a nightgown. “I’m sure that you will want to wear this to bed,” she said, with a smirk. I did, but I got up first thing in the morning so Dad wouldn’t have to see it. Thanksgiving dinner was pretty much as usual, except that my cousin Jane was there and had to hear everything about me being Halloqueen. She already knew about my CD’s so it wasn’t a total surprise.

On the Friday after Thanksgiving, I called Sandy, just to see how things were going. Despite our breakup, we were cordial with each other. She pointedly wanted to know if I was still cross-dressing.

I had a lot of homework and a paper to write, so I spent most of my remaining time reading Proust and Balzac.

Chapter 36 - Dancing Queen.

Several sororities jointly hosted a Christmas Dance to be held at the same place as the Halloween party. Naturally, as Halloqueen my attendance was requested. “Do I have to have a date?” I asked Ann, “after all Sylvia will be there.”

“You may bring a boy as a date if you want, but it is not required,” she answered. “However,” she added, “you will be rather busy the whole evening.”

“Doing what?”

“Well, all the officers of the sororities met and decided that you should be the honorary hostess for the dance. You will welcome everyone to the dance, and will lead off dancing with the head of the fraternity council.”

“Does he know about me?”

“I don’t know, but that shouldn’t be a problem, After that you will dance with all of the officers of the fraternities who are there. I’d suggest you find a pair of comfortable heels,” she added with a laugh.

“What should I wear?”

“Either the dress you wore when you won the contest or the dress you wore on the float.”

“I like the white one,” I said.

“I think everyone else likes the green one,” she said, “We can get you some red accents to make it look festive.”

By now Sue had joined the conversation. “You know, red stockings and red garter straps would look great, give it a Christmas look.”

“You know, you’re right,” Ann agreed. “Bright red, not dark red or burgundy.”

“And we all expect to see a red leg come out of the slit, a lot.” Sue suggested.

“That means red shoes,” Ann added.

Sue obviously didn’t trust me, so she and Sylvia hauled me to the mall and corset shop for my purchases. Of course, I wore a skirt and blouse for the occasion. They insisted that the garter straps matched the hose.

On the day before the dance, the President of the sorority sought me out, and handed me a box. “It’s a corsage. The fraternity council bought it for you.”

I opened it up. It was red, like my hosiery.

The next day I used a hair remover. The girls handed me a bag. “New Lingerie,” Sue said, “Red.”

About three-thirty in the afternoon the girls started working on me, starting with my red lingerie and stockings. This time Rachael worked on my hair. She had decided that a high pony tail was a good choice, since it could be tied with a bright red ribbon.

The girls had a discussion about my makeup. As usual, I was not consulted. They finally agreed on heavy eye makeup, with a lot of red in it. They even treated me to a set of false eyelashes. Shortly thereafter Ann came out of her room with bright red nail polish. I had let my nails grow, so I didn’t need false nails, although this was discussed.

At my trip to the mall, the girls had insisted on red shoes. The ones they chose had open toes, so the same red nail polish was put on my toe nails. The only thing I liked about these shoes was that they were more comfortable than any of the others I had tried on.

They were done sometime before five, when they went to their rooms to get dressed. While they were getting ready I snuck a look in the mirror. I really looked all tarted up, especially when my left leg was outside of the slit.

I was supposed to be at the dance at about six. The dance was to start at seven. Rachael had a red purse which she loaned to me for the occasion. Sylvia, Rachael and I rode together, and arrived at the dance a minute before six. The presidents of the sororities were already there. When I walked in, they all looked at me with astonishing approval. “Wow, you really outdid yourself, you look absolutely delicious and beautiful,” one said.

“Let’s see some leg,” another added.

“Ooh, hosiery and garters,” a third said, “very sexy,” she added.

“You’re going to drive those frat boys crazy,” another said, “expect some dirty looks from their dates.” Then all of them individually told me to behave myself with their dates.

One of them whispered to me, “Are you sure you’re really a boy? You look all girl tonight.”

Their dates had been standing around the bar when I came in, but like moths and flames, the came over. “Hey, sexy,” one said, “I can’t wait to dance with. . .Oof!” He didn’t finish his statement because his date jabbed him in his stomach with her elbow.

“Watch it, buster,” she said, hinting that otherwise it would be a chaste night for him.

It was then that one of the girls handed me a red sash with ‘Halloqueen’ in silver letters on it. Then the girls gave me the schedule of what I was to do and when to do it.

The doors opened at six-thirty, and by seven the place was crowded. As expected, most of the boys gave me admiring looks and their dates scowled at them and gave me dirty looks. However, there were some girls who gave me admiring and inviting looks. Sylvia, who stood beside me was the one who scowled at them and gave them dirty looks. “Just remember, you’re mine,” she whispered and patted my butt.

At seven-thirty the DJ handed me a microphone, and I made my welcoming remarks. Then the dancing started. As scheduled, my first dance was with the head of the fraternity council. After that, I must have danced with all of the officers of the fraternities. Although it was fairly well known that, as the Halloqueen, I was a boy, none of them invited me to consider joining their frat.

All evening I showed a lot of leg, and there was no doubt as to what I was wearing underneath my gown. I was in cross-dresser heaven.

All of Sylvia’s roommates had dates, and when the dance broke up they and their dates went out for something to eat, or maybe something else. I didn’t ask. That meant that when Sylvia and I went back to her apartment, we were the only ones there. Decency dictates that I not mention what then happened.

When I woke the next morning, I discovered that I was wearing a sheer nightgown, and curled up with Sylvia in her bed. It was a little cramped, but I remembered that neither of us had complained about it the night before. We both got up and went into the kitchen and made coffee. It was then we noticed that not all of Sylvia’s roommates were present in the apartment.

Chapter 37 - Rush.

Fraternity and sorority rush started right after the prior term’s grade were released. Sylvia was invited to join several sororities, and chose Ann’s. I, on the other hand, was only invited to join one fraternity. I suspect that Ann and other members of her sorority had a hand in pressuring the frat to make that invitation, since the sorority which Sylvia joined wanted their members to only date fraternity guys.

Another factor may have been that the college kept track of all of the fraternity members’ grade point averages, and the fraternity which invited me to join, Rho Lambda Epsilon or RLE, was dead last in grade point averages. My first term grades were very good; one B and the rest A’s, a fact which would benefit the fraternity.

There were some casualties in the grade point battle. Tiffany did not return for the next semester. My dorm roommate was placed on academic probation. If he didn’t improve his grades dramatically, he wouldn’t be allowed to play in any sports, and would loose his athletic scholarship.

Shortly after the semester began, I went to my dorm room to study and tickle the ivories on my keyboard. My roommate was there, with a book open on his desk and a desperate look on his face. Knowing that he was on probation, I only said hello.

He then turned to me. “Hey, egghead,” he started, “my grades stank, and the dean suggested that I find a tutor or my days here are numbered. How are you at math?”

“Pretty good,” I said, “Why?”

“Can you tutor me in math?” he said with a look of desperation, “I can pay you for your time.”

“Ok,” I said. “What other courses do you need help in?” I asked.

“All of them, but math is the worst.”

“Aren’t we in the same music history course?” I asked.

“Yeah,” he answered.

“I can help you there, too.”

So I agreed to tutor him. He had to repeat last semester’s math course. I looked at his textbook. It appeared that it had barely been used. I had taken the same materials in an advanced placement course in my junior year in high school. So the two of us set up a tutoring schedule.

It turned out that he wasn’t stupid; he just didn’t seem to grasp the idea that he was supposed to learn something at college. I also found out that none of the fraternities would touch him with a ten foot pole because he had such a lousy grade point average. It appeared that the frat which he wanted to join was the same frat that I was joining. It was referred to as the dumb jock fraternity, not that I minded.

As a result of the tutoring, we opened up to each other. “So, you’re pledging RLE,” he said, “that’s the one I wanted to join, but I can’t with my lousy grades.”

“Well, let’s get your grades up, and maybe you can join next year.”

“Will you put in a good word for me?” he asked.

“Sure,” I answered. I liked the thought that he was indebted to me.

Gene or Jean? - Part 6 - How I got a job wearing a dress

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • School or College Life
  • Voluntary

TG Elements: 

  • Fancy Dress / Prom / Evening Gown
  • Performer/Entertainer
  • Valentine's Day

Other Keywords: 

  • Cocktail piano Fraternity Sorority

Permission: 

  • Posted by author(s)

Gene or Jean? - Part VI - How I got a job wearing a dress.
By Pentatonic

Chapter 38 - The Winter Carnival.

The college sponsored a Winter Carnival every year near the end of January to give everyone a chance to blow off a little steam. There were all sorts of activities such as figure skating contests, snow man building, and even sleigh rides. Some of the frats and sororities had booths with food, hot cider and cocoa. Others set up carnival type of games. The college even cancelled classes for Friday. Naturally, my presence, as the SRS Halloqueen, was requested, and because of my position, RLE didn’t object.

“I don’t have anything to wear,” I lamented to Sylvia.

“Said just like a woman,” she responded. But in my case, I didn’t. My feminine wardrobe was limited by where I could keep it. So the girls and I went shopping. I was able to borrow a white fake fur trimmed parka, but I had to buy ski pants and snow boots.

Suitable attired, and wearing my Halloqueen sash, I was assigned to SRS’s booth, selling cider and cocoa. I was in the booth, with only two other girls, when I spotted Frank, my roommate, heading over. Panic. “I have to get out of here,” I said. I didn’t want Framk to see me.

“You can’t leave now,” one of the girls said, “we’re too busy.” So I ended up serving Frank a cup of hot chocolate. He was too busy ogling the other girls to make the connection between me as Halloqueen and his roommate, but that was about to change.

Two additional girls arrived to man the booth, and one of the girls said, “We’re okay now, why don’t you take a break.” It was then that Frank came up to the booth again.

“Hey, Halloqueen,” he said, “why don’t you and I walk around together.”

I hesitated. “Go ahead,” one of the girls said, and I took off my apron and stepped out of the booth.

As Frank and I walked we made the usual small talk. When I mentioned where I was from, he said, “My roommate’s from there. Do you know him?”

“Yes,” I answered.

We talked about the courses we were taking. While I well knew what he was taking, I feigned interest in his courses. When he asked me about my courses, I didn’t think about it, so I answered him.

“My roommate’s taking the same courses,” he commented.

‘Oops,’ I though, maybe I’m giving him too much information.

We talked about me being the Halloqueen and what I did as Halloqueen. “I go to all of the school functions and sorority functions,” I answered him.

“Yeah, I saw you at the Christmas Dance.” he commented, “you really looked foxy in red and green. That slit up your skirt was really sexy.”

“That was the whole idea,, or at least the sorority’s idea.” I responded, “It wasn’t mine.”

“Hey,” he said, “don’t they say, ‘ if you’ve got it, flaunt it,’ and you’ve got it.”

“I’ll take that as a compliment,” I said, smiling at Frank.

“You ever talk to my roommate about why he doesn’t go to dances and suff like that?” Frank asked.

“We may be from the same hometown,” I answered, “but that doesn’t mean I’d ask about stuff like that.”

During our conversation, I let slip some more facts which connected me, the boy, with the Halloqueen. Frank’s grades may leave something to be desired, but, as I said, he wasn’t stupid. Then, it came to him. He stopped walking and turned to look at my face.

“Ahh, eer,” he mumbled. He then found his voice. “You’re my roommate!” he declared. I had to admit that he was correct.

“How come you never told me?” he said.

“I knew that you didn’t like cross-dressers,” I said in the nature of an explanation.

“Yeah, maybe, but right now I like a certain cross-dresser,” he said as he took my hand in his. We continued to walk. Frank seemed very happy to show me off to his friends, like I was some trophy.

That week, I was tutoring Frank, and he said, “How come you never wear a skirt here?”

“I don’t think it would be a good idea,” I said, “anyway, it takes me a lot of time to look like a girl.”

“Maybe so, but you’re really good at it,” he said, “all of my friends were impressed that I was walking around with the one and only Halloqueen.”

I did, however, dress up for him, to satisfy his curiosity. “You really look good,” he said, “If I didn’t know better, I’d want to kiss you.” He paused, still looking into my eyes, and then said, “What the heck?” and he kissed me.

“You kiss like a girl,” he said.

“I didn’t think you’d like it if I kissed like a boy,” I responded.

“Well . . .,” he said.

“No matter how I kiss, just remember that I have a very jealous girlfriend.” I said, “and I don’t think that I’m gay.” However, after swearing me to secrecy, Frank admitted that he was.

Chapter 39 - Valentine’s day.

Like the prior dances, the sororities and frats were hosting a Valentine’s day dance, and as Halloqueen I had a role in it. The first problem: What to wear.

“Something red and slinky,” suggested Rachael.

“With a slit up the side,” added Sue.

“Great,” I said, “but I don’t have anything like that. You know, I could wear the white dress I wore on the float.” The girls didn’t like that idea.

“Shopping time,” Ann declared. “Get dressed, and wear your corset.” When I was suitably attired, we headed to a discount dress outlet. Once there, the girls went directly to the cocktail dress section. Rachael was the first to strike pay dirt. She came up with a red cocktail dress that was a little shorter than knee length. The main asset, however, was a slit up the left side. She handed it to me and directed me to try it on.

It fit.

Rachael’s discovery only encouraged the others. As always. my opinions were not solicited, and I was told to just stand there, try on dresses, and be quiet.

Sue found a pink dress with a full skirt. “This would be darling with her red hose,” she suggested.

A slinky pink dress, with a slit was then found. The hem of this was just below mid-thigh. Way too short, I opined. I was ignored.

After a lot of conversation, the pink one with the slit was chosen, probably because I already had red lingerie.

The procedure for the Valentine’s dance was much like the Christmas dance. While sitting in the kitchen, I noticed that Sue was using a lot of makeup on my face. “Go easy on the makeup,” I said, “I don’t want to look like a cheap hooker.”

“Oh, I won’t do that,” Sue said, “I’ll make you look like an expensive hooker,”

The dance was much like the Christmas dance. I started with some words of welcome. When I stepped up on the stage, I was greeted with the usual whistles. I decided a little tease was in order, so I smiled broadly, hiked up the hem of my skirt an inch or so, and gave everyone a good look at my leg which included the top of my stocking and a garter strap. This drove the boys wild, and I noticed more than one girl elbow her date in the ribs.

As before, I started the dancing with the President of the fraternity council, and then what I called the ‘mandatory’ dances with officers of the fraternities.

Then I noticed Frank, my roommate. He came up to me and asked me for a dance. “As long as you behave yourself,” I said.

“You’re so beautiful, that may be difficult,” he said, “I keep on thinking what’s underneath that dress.”

“Try not to,” I said.

“You know, you can come directly back to our room, you don’t have to change first.”

“Sylvia might not like that,” I responded, “and there is chance that I might stay overnight at her apartment.” It was a lot easier before Frank knew that I was the Halloqueen and I knew that he was gay.

“Anyway, don’t you have a boyfriend?” I asked.

“I do. You.” he answered.

Not what I wanted to hear.

Like Christmas, I spent the night at Sylvia’s apartment.

Later that week, Sylvia, along with the other girls and I were sharing some takeout food at the apartment. “Who was that big hunk I saw you dancing with,” Sue asked.

“That might have been Frank, my roommate.” I answered.

“Does he know?” she asked.

“He figured that out at the Winter Carnival.” I answered.

“And he still wanted to dance with you?”

“Well, yes,” I said, “and I discovered something about him. He’s gay. So now I have a boyfriend in addition to a girlfriend.”

“You only need a girlfriend, me,” Sylvia said, “has he tried anything funny with you?” she asked.

“No.”

“Keep it that way.” she said.

“He likes it when I dress,” I added.

“So do I,” Sylvia said. “Just don’t let him see you.”

Chapter 40 - Spring Break.

With spring break around the corner, a lot of my fellow students were planning to go to Florida. I was not one of them.

Mr. Phillips had called my agent and asked if I would ‘cut’ another record. Since making my last CD I had been composing and writing some new songs, and I readily agreed. He scheduled a session in the middle of the week. When I told this to Sylvia, she had some reservations. “I had hoped that you could spend some time with me at my house,” she said.

“I can,” I replied, “either at the start of the week or the end of the week. The start might be better, because I don’t know how many recording sessions there will have to be.” So, after my last class, Sylvia and I packed my car and headed off to her house. At Sylvia’s insistence I had packed a suitcase of girl clothes. I wasn’t sure why, because I had enough girl clothes at my house to cover the recording sessions. It was when we were at her house, I found out that Sylvia had planned a weekend of me being a girl, starting with going out to dinner with her parents.

“What about your parents?” I asked, “Won’t my dressing come as a surprise to them?”

“No,” she said, “I told them about you being the Halloqueen and sent them some pictures, so they’re expecting it. In fact, they may be looking forward to it.” I couldn’t imagine why.

After coming back from shopping on Saturday afternoon, Sylvia said it was time to start getting ready to go out to dinner with her parents. When we were ready, we met her Mother in the living room, “Your Dad will be with us shortly. He had some wardrobe issues.”

A few minutes we were joined by a nicely dressed middle aged woman. Sylvia jabbed her elbow in my side and chuckled.

Surprise, surprise, the woman was her Dad - her dad was a cross-dresser! He, or rather she, was wearig a maroon dress with a full skirt. The top part had a square neckline, and she wore a delicate gold necklace. Her makeup was subdued, and she was wearing a wig. “Sorry for the delay,” she said, “I couldn’t get my breast forms to look right until I realized that I had mixed two different sets. You girls might not understand, but maybe Jean would.”

“I do.”

“Mom says that she likes it when Dad dresses,” Sylvia said.

“It turns me on,” Sylvia’s Mom added.

“It must be genetic,” I muttered to myself.

“I heard that!” Sylvia said, “and maybe it’s true.”

“You have such a nice figure, how do you do it?” her Dad asked.

“An uncomfortable corset,” I replied.

“See,” her Mother said to her Dad, “how many times have I told you to get a corset?”

“Okay, maybe I will,” he replied.

So it was four ladies who went out to dinner that evening. Sylvia’s Dad was very interested in me being the Halloqueen and I had to relate all of the details.

Sylvia wanted to go with me to the recording studio, so at nine on Wednesday morning we met Mr. Phillips and Mr. Nicholas at the studio to go over the music. I was wearing a skirt and sweater. The first thing we did was for me to play and sing what I had written, as Mr. Nicholas timed each piece. After I had sung a song, they placed the score in one of two piles, ones we would include in the CD and ones we would not. “These we will put on the market to sell. As you will recall, we did that for your last CD, and we have actually sold about half of them,” Mr Phillips said, more for the benefit of Sylvia than for me.

Mr. Nicholas then pulled a pile of scores from his briefcase. “Why don’t you read through these?” he suggested. “We’ll record the ones you wrote today, and you can practice these others this evening and we will record them tomorrow.” He and Mr. Phillips had timed it perfectly. The recording crew began filtering in just as we finished going through the music. This time a drummer and string bass player arrived with the crew.

I laid down the piano track, first with the drums and bass, and then without. After this I laid down my vocal track and my vocal harmony track.

It was mid-afternoon when we finished. “Good session,” Mr. Phillips said. “Now go home and practice these others and we’ll meet at ten to record them.”

When the session ended, neither of us had eaten lunch, and Sylvia asserted that we were famished. We stopped at a fast food joint to satisfy our hunger pains.

No one was at my home when we arrived. There was a note on the table directing me to take a casserole out of the refrigerator at a certain time, and put it in the oven. The note continued to say that my parents would be home about six.

“I’ll have some time to go over these pieces,” I declared. Sylvia, who got turned on when I wore a dress or skirt had other ideas and led me to my bedroom. I had no idea when any of my sisters would arrive home, but neither of us really cared. Afterwards, I started rehearsing the music supplied by Mr. Nicholas, and finished about midnight, with a break for dinner.

The second recording session then went much as the first had done, except that Mr. Nicholas had me speed up or slow down some of the songs. As before, we completed the session by mid-afternoon.

After stopping for some fast food, we went back to my house. My parents were not due home from work until at least five-thirty, and as before, Sylvia had an idea as to how we should use the time before they came home.

The rest of the week Sylvia and I went shopping and otherwise amused ourselves.

Chapter 41 - Girlfriend.

At Sylvia’s insistence I remained dressed on our trip back to the campus, and after I dropped her off at her apartment, I went to my dorm room. Frank was there.

He looked me up and down, and then said, “Welcome back, girlfriend.”

“You’re very nice,” I responded, “but I’m not your girlfriend. As you well know, I’m not even a girl.”

“But you look like one,” he rejoinded, “and a very pretty one at that.” He moved over to me and surprised me with a kiss. I did not kiss him back. “Aw, sweety, you can do better than that,” he complained, and kissed me again. This time I responded. Still holding me he slid his hand down to my butt, and began rubbing.

“Enough!” I declared, “Please stop that at once.” He reluctantly released me and moved away a bit.

“I bought you a present as thanks for your help,” he said, and he pointed to a parcel on my bed.

“You pay me for my time as a tutor,” I said, “and that’s enough. You don’t have to give me presents.”

“Well, aren’t you even going to open it?” he asked.

“Well, okay,” I answered. Inside the parcel was an ivory colored nightgown.

“I got one just like it for me,” he said, with a smile.

“Thank you,” I said, “but I don’t know how I can wear it here.”

“That’s simple,” he said, “we lock the door, take off our clothes, and put the nightgowns on.”

“In your dreams,” I said, and folded the nightgown and put it back on my bed.

“Aren’t you even going to try it on?” he asked as he locked the door, “I will if you will.”

I just sighed, and started to undress. Frank did the same.

The nightgown was very pretty, at least on me. Frank’s was a plus size, and not as attractive on him. I started to take the nightgown off. “No, leave it on for at least a few minutes,” he said and he moved toward me and gave me a hug. He followed this with a kiss, and I could feel him fondling me.

While it felt good, I insisted he stop. We took off the nightgowns. I still had my panties on, and there was a involuntary bulge as a result of his fondling me. He saw it, and said, “So, you have to admit that I turn you on. That’s good, since you turn me on.”

I turned to him and said, “We’ve got to talk.”

“About what?” he responded.

“You hitting on me,” I said. “You’ve got to find a boyfriend or girlfriend of your own.”

“It’s not that easy,” he said. “It’s not like I can put up a sign or ad in the paper saying ‘Gay football player seeks lover. Cross-dressers welcome.’ I can’t let the guys know that I’m gay. You’re the only one on campus that knows.”

I thought for a moment and said, “Have you contacted any LGBT groups?”

“No,” he responded, “if I walked into a meeting, my secret would be out, so I can’t.”

“I’ve never looked for a gay lover,” I said, “so I can’t be of much help to you.”

Frank thought for a minute, and then said, “I’d go to a LGBT meeting if you’d go with me. They’d think that I was your protection, and not suspect that I’m gay.”

“But everyone would think that I was, so your answer is no.” I responded. “I guess that you’ll have to go trolling near gay bars,” I said.

“Which ones are those?” he asked.

“Go looking. I certainly don’t know.” I concluded, “In the mean time, no touching or kissing.”

I finally gave in and went with Frank to a LGBT meeting. A lot of those present cast hungry looks at me, which I ignored. Frank was successful and it was not too long thereafter that he found a lover. I accommodated them by leaving them alone in the dorm room for their trysts. I even gave Frank’s lover the nightgown which Frank had bought for me.

Chapter 42 - Spring Fling.

The final event which the sororities and frats hosted was the ‘Spring Fling’ which followed the frat and sororities’ initiations. I was in a quandry. They wanted me to be there as Halloqueen and to dance with all of the new members of the frats, but my fraternity wanted me present as a new member. I hoped that I could attend as a new frat member, and not as Halloqueen, but that was not what the powers that be decided. I suspected that Ann had a part in this.

They decided that I would be the Halloqueen, and as such be introduced as a new member of my frat, fully dressed, as they directed, in the same clothes as I wore at the Valentine day dance. I was directed to show a lot of leg. I finally went along with what they had planned. However, someone was needed to dance with all of the new members of the sororities, and a likely suspect was convinced to do the same. Of course, I was to dance the first dance with him. He didn’t like the idea, and neither did I, but we were pressured into doing it.

There was one surprise. During the time the DJ was on break, Jill, the President of SRS, presented me with a photo album of all of my appearances as Halloqueen. When she presented it, she made a little speech, acknowledging how I was one of the best Halloqueens for many years, and how I really showed school spirit, and a lot of leg. She even plugged my new CD.

After Spring Fling, the student body worked on final projects and papers, and prepared for the final exams. Frank was pleased with his performance that semester to date. Going into finals he had a good average in his courses, and he felt confident that he would do well on the final exams.

I also felt confident that I would get A’s in most of my courses, which I did.

Summer was approaching and I hadn’t lined up a summer job. Being a self-employed songwriter just didn’t cut it. The earnings from my recordings were modest. I needed a real job.

Sylvia and I were sitting at the kitchen table in her apartment. At her insistence I was wearing a blue pleated skirt, pantyhose, heels and a black chiffon blouse. When I related my problem to Sylvia, she suggested that I list my assets and see if they suggested a job. Sylvia picked up a pencil. “Give me an asset,” she said.

“Fluent in French,” I responded.

Sylvia chuckled and said, “Great looking legs.” She twirled the pencil around, “good in bed,” she added.

I looked at her list. “These sound like the qualifications for a high priced courtesan,” I said.

“There’s a thought,” she said.

“Not a very good one,” I muttered.

“How about sings and plays piano?” Sylvia said as she wrote them down.

“Not much use for flipping burgers in a fast food joint,” I responded.

“Don’t be so negative,” she said.

“I’m not negative,” I rebutted, “I’m a realist.”

“And a cute realist,” she said, as she slid her hand up my skirt.

“Oh, we can’t forget ‘likes dresses with slits up the side’,” she added.

“I don’t,” I countered.

“But I do, when you wear them,” she said, with a wicked smile on her face.

“Hummpf,” was my response.

“Let me improve your mood,” she said as she took hold of both of my hands and lifted me up off of my chair, and led me to the bedroom.

About an hour later we were again sitting at the kitchen table. My mood indeed was better. “Hey,” I said, “I just got a check from the record company. Let’s go somewhere fancy tonight for dinner.”

“That works for me,” she responded. “Now, what to wear?” she posited.

“Coat and tie,” I answered.

“Spoil sport,” she said, “I was thinking a nice dress,”

“For you? That would look nice,” I responded.

“No, for you, silly,” she rejoined.

“If you insist,” I said.

“I do.”

So I changed into a deep violet dress with an A-line skirt and fitted bodice. Sylvia was likewise attired, and we headed downtown to the Carleton House, the most fancy restaurant in town. We hadn’t made reservations, so we had to wait in the lounge area, which was okay, because a woman was playing cocktail piano. “You could do that and sing,” Sylvia speculated.

Chapter 43 - A Job Offer.

It was a half hour later that our table was ready. We could hear the piano in the dining area. As we were being escorted to our table, I mentioned to the maitre d’ that I really enjoyed the piano.

“Enjoy it while you can,” he said, “because she and her husband are going away for the whole summer.”

“But you have a replacement?” I asked.

“Not yet,” he said, as he looked me up and down, “You play?”

“Yes,” I answered.

“She’s a recorded professional,” Sylvia interjected.

“You union?” he asked.

“No,” I responded, “Is that important?”

“Gotta be union to work here,” he said.

“How hard is it to join?” I asked.

“If you’ve got a gig lined up and pay your dues, you’re in.” he said, “If you’re interested, come by on Monday afternoon and talk to the manager,” he added.

So that Monday I wore a cocktail dress which I borrowed from Ann, and Sylvia and I went to the restaurant. The manager checked out my appearance. “You look okay, now let’s see if you can play as well as you look,” and with that he led me to the piano. I sat down and began to play. “Okay, you can play,” he said. “I’ll give you the names of some songs, and let me hear you play them.”

Two of the songs he named were on my CD’s, and I had those down cold. I noticed that there was a microphone near the piano. The manager saw me looking, and asked, “You sing?”

“Yes,” I answered. “Two of those songs are on a CD I released a while ago.”

“You’ve got music on the market?” he asked with a little incredulity. I nodded my head.

“Could you loan me a copy?” he asked.

“No problem,” I responded.

“Okay,” he continued, “we have music three hours Wednesday through Sunday evenings. We pay union scale. Tell the union that I hired you. Can you start three weeks from Wednesday? That’s when our current pianist is leaving for vacation. The gig runs through Labor Day when our regular pianist returns.”

“So I’m hired?”

“You bet,” he responded. “If you’d like, I’ll buy you and your boyfriend dinner on Wednesday and you can talk to Adele about what you can expect.” Adele was the regular pianist.

Sylvia was not happy that she was not included in the free dinner, but she assured me that it was okay provided that I took her shopping with me. “All of the girls agree that you need some more cocktail dresses for your job. So, who’s going to be your boyfriend on Wednesday?”

“I think I’ll ask Frank,” I responded.

That evening I mentioned my new job to Frank. “I’ll be playing cocktail piano five evenings a week at the Carleton House restaurant. They want me to come over on Wednesday with my boyfriend to give me a chance to talk with the regular pianist before she leaves for the summer.”

“So?”

“I want you to pretend to be my boyfriend. You’re big enough to be my protection. You get a free steak dinner out of it,” I said, “That is, if your boyfriend doesn’t pitch a hissy.”

“Just a meal?” he asked, with a gleam in his eye.

“Just a meal,” I responded , forcefully.

The next day the girls and I went shopping for cocktail dresses for me. It became readily apparent that my only purposes of being there was to make sure the dresses fit and to pay for them. The girls were having a great time, the more risque the dress, the better they liked it. Naturally, all of the dresses had revealing slits.

I objected. “You realize that I’ll be sitting at a piano, so the dress will fall open, revealing a lot of leg.”

“And that is a problem?” Ann said, “I don’t think so.”

I ended up with two new cocktail dresses, one in royal blue and another in a deep maroon, The hems of both came to a few inches above my knees, and the bodices were fitted. Naturally, buying a dress wasn’t all. We looked at shoes. I reminded them that I had to use the pedals on the piano, but I still ended up with four inch heels. Then came stockings. The girls insisted that I have stockings, not pantyhose. Since the dresses would be revealing, they insisted that I purchase new lingerie, in black.

So, suitably attired, I picked Frank up at the dorm. He was dutifully impressed. “I wish that you were my boyfriend,” he said, “You look so beautiful and sexy.” When I drove to the restaurant, the skirt of my dress fell open at the slit, exposing my stocking tops. Poor Frank couldn’t keep his eyes from my legs.

Adele, the regular pianist was maybe fifty-five and a plus size. “You’re going to drive them wild,” she said when she first saw me. Frank and I had our dinner in the lounge, next to the piano. Adele and I traded off sets. “You’ll do just fine, Honey,” she said. I asked about boys hitting on me. “I never had the problem. At my age, I consider being hit upon to be a compliment. Some men will want to buy you drinks. The bartenders will give you a soft drink when this happens. Just tell them what you like.” She paused. “Of course the guys buying you drinks will get charged as if it were a mixed drink. Keep a tip glass on the piano. You should collect a few bucks extra every night. If anyone gives you a problem, give a signal to the bartender and someone will be sent to rescue you.”

Frank and I left when Adele was finished for the evening, and I drove Frank back to the dorm. His boyfriend was waiting for us. I leanded over and whispered, “You want me to spend the night at the apartment?”

“That would be a nice idea,” he said. When I got to the apartment. Sylvia also thought it was a nice idea.

So I had a summer job lined up. It was only 15 hours a week, but at union scale, which would earn me more over the summer than if I was flipping burgers. However, I couldn’t help wondering why I seemed to need to wear a dress more and more.

Gene or Jean? - Part 7 - Conclusions

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Final Chapter

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Voluntary

TG Elements: 

  • Corsets
  • Fancy Dress / Prom / Evening Gown

Other Keywords: 

  • Bisexual
  • Singing
  • Piano playing

Permission: 

  • Posted by author(s)

Gene or Jean? - Part VII - Conclusions.
By Pentatonic

Chapter 44 - On the Job.

Classes were over, and I maintained a respectable grade point. The girls had gone their separate ways and I had moved into their apartment for the summer. I found out that Frank had pulled himself out of academic probation and was eligible to play football. Sylvia had a summer job at her Dad’s company, which meant that she had to work on Monday and Tuesday, the only days I had off. I would really miss her.

Before we all went our ways for the summer, Sylvia had an astute observation, “You’re going to be dressed for five of the seven evenings of the week, so why not make if full time until college starts in the fall?”

“That’s a good idea,” I responded, “that way I can have my hair done in a really feminine style, and maybe have some highlights. That way I won’t have to change the style all summer.”

“So you’ll be Jean the whole summer?” Sylvia wanted to know.

“Yeah, that’s about it,” I responded, “You know where I can get my hair done?”

“I know a good salon, and you could make an appointment for the day that classes end.”

“Okay,” I said, “but there is a problem. All of my casual clothes are my male clothes, so I’ll need to get some feminine casual clothes if I’m going to be Jean all summer.”

“I can help you there,” she responded. That was obvious. Sylvia loved clothes shopping with me. I had plenty of skirts, blouses and dresses. What I needed were the kind of clothes that girls wore to class and around town. “Let’s walk around and observe what girls wear when dressed casually.” So we began a reconnaissance by walking around town and campus, and then went shopping. Sylvia insisted that I wear my kilt and a blouse.

I saw and rejected any distressed jeans. Shorts were good, Capri and cropped pants worked, as well as some leggings and exercise pants. “You’ll need quite a few,” Sylvia observed, “because you will need something to wear during the day on the days you work.”

Naturally, a collection of tops were also required. “There are so many cute tops, it’s hard to decide,” Sylvia observed.

We also hit the shoe stores for some casual shoes and sandals.

My appointment at the salon was for later that week. Sylvia delayed her return home so she could accompany me for my ‘new look.’ While I had visited salons before, this was my first time at this one. We went in, and met Gail, who would do my hair. “And what do you want?” Gail asked. “The works,” Sylvia announced.

“I’m perfectly able to figure out what I want,” I said reprovingly.

“No, you can’t,” Sylvia answered. “Have I ever given you bad advice?”

She turned to Gail. “Jean’s got a gig at the Carleton House restaurant playing cocktail piano five evenings a week. She needs to look glamorous.”

“I want something that is easy to take care of, since I have to look good five days in a row. I wonder if I could have a standing appointment for Wednesday afternoons. I play Wednesday through Sunday.”

Gail lifted up some of my hair. “When was the last time you had a trim? You have some split ends. You ever try highlights?”

“It’s been a while,” I responded, “and no, I’ve never tried highlights.”

Sylvia felt compelled to explain why. “You see, Jean is a boy, so she cannot have highlights when she is in boy mode. She’ll be dressed as a female all summer, so she can have highlights.”

Gail gave me a questioning look. “Sylvia’s right. I can have highlights and a very feminine style until Labor Day, at which time the highlights have to go and I need a style which is less feminine.”

“Why do you need to wear skirts or dresses this summer, just to play cocktail piano?” Gail asked.

“I got the job when Sylvia and I went to the restaurant, at which time I was wearing a dress. They hired me as a woman.”

“You’re not, umm., err?” Gail asked.

“No, I’m not gay or transgendered,” I answered. Sylvia just rolled her eyes when I said this.

“Then why did you wear a dress?”

“It’s a long story. If you want, I can explain it to you while you do my hair.”

“This has got to be good,” Gail said, with a smile. “Do you want a make over?” she added.

“Of course she does,” chimed in Sylvia.

“Okay, Honey,” Gail said, “when we’re done with you, you’ll look good enough to win a beauty pageant.”

Sylvia couldn’t let that pass. “She already has.”

“What?” Gail asked.

“It’s all part of the story,” I responded,

Gail examined my face. “I can see why that could have happened. Your face is too pretty for a boy.”

Gail then led me to a chair. “I’m going to wash and trim out the split ends. Then we’ll decide what to do with this beauty. What kind of styles have you tried before?”

“A french twist, a pony tail, brushed back with a headband,” I answered.

“Which one did you like best?” she asked.

“All of them,” I replied.

“Can I change the color?”

“As long as it’s not too much. After all, I’ll have to dye it back to it’s normal color at the end of the summer and I return to college as a boy.”

Gail then began to work on my hair, during which time I told her about my times in skirts and dresses, with a lot of volunteered commentary coming from Sylvia.

“So, Sylvia is your only girlfriend,” Gail observed, “and no boyfriend?”

“You’ve got that right!” exclaimed Sylvia.

“And you don’t mind it when he wears women’s clothes?” she asked Sylvia.

“I don’t mind, in fact I like it. It turns me on,” Sylvia answered.

We, and that included Sylvia and Gail, then selected a style. I suggested an up do, and Sylvia provided the details.

When my hair was done, I was moved to a makeup station. When finished, I loved the look. I had also asked for a manicure. “Do you want artificial nails” the manicurist asked.

“I have a job as a pianist, so the answer is no. Just trim them and shape them.”

* * *

The day arrived when I was to start my job. I used a hair remover and took a long bubble bath, which left me with a feminine aroma. I took my time to get ready. Sylvia had insisted on stockings and garters, and I did have to use the corset to fit into my cocktail dresses. Because of the dark color of my dresses, I had to wear black stockings and black lingerie. I had an appointment at the salon that afternoon for my hair and makeup, and for this I wore a skirt and blouse.

After my visit to the salon, I trimmed my nails and used a dark maroon polish to go with my make up. At five I put on my dress and added some costume jewelry. When done, I looked in the mirror. ‘Pretty darn good,’ I said to myself.

Driving to the restaurant in heels meant that I had to drive very carefully. I also reminded myself that my license identified me as a male, so I didn’t want to get pulled over by the police. I parked in back and let myself in using the employee entrance. The manager greeted me as I entered. “Ready for the big day?” he asked.

“I think so,” I answered, How do I look?” I turned around so he could see. Naturally, when I did that the slit in my skirt opened, showing a lot of leg. He smiled when he saw that.

“Very good,” he commented, “I want you to come with me up front for a minute.” When we got there, I saw a big poster, professionally done, that said, ‘For a limited time only, international recording star Jean Torne.’ Below this was my picture and below that it said, ‘Every Wednesday through Sunday, 6 to 9 through Labor Day.’ I was impressed, and I thanked the manager. Near the bottom, the poster said that my CD’s were available for purchase.

There were quite a few patrons in the lounge, and I could feel their eyes following me as I walked to the piano. I sat down, gave the patrons a big smile, and started playing. After playing for a while, I noticed that there was some applause after each number. I bowed my head in acknowledgment. There were a group of businessmen sitting near the piano. Then one of the men came up to the piano, and put some money in my tip jar. “I heard that you can sing. Are you going to?”

In response, I said, “let me see if this microphone is on.” It was. I decided that Parlez-moi D’Amour would be a good number. I took the microphone and said, “I’m going to sing a song in French, roughly translated as ‘Speak to me of Love,’ I want you to imagine you are in a cellar night club in Paris in the 1930s, when Lucienne Boyer sang this song.” While I sang, I noticed that conversations between the patrons had stopped. When I finished, I received a pleasant round of applause, so I stood up and curtsied, naturally showing a lot of leg coming out of the slit in my skirt. The men seemed to like this, as did the manager who told me so when I took my first break.

My first week was very successful. The manager told me that a lot of people were coming in just to hear me play and sing. “Liquor sales are up,” he told me, “That makes us very happy.”

I had some business cards printed up which said, ‘Cocktail Piano With Jean,’ which had my cell phone number on it.

* * *

A few weekends later Sylvia and her parents came up to hear me perform. Sylvia and her parents were all wearing summer dresses. I sat with them during a break. “You all look so pretty,” I said.

Sylvia’s Dad smiled. “I just wanted to join in with the fun,” he said, “or at least as much fun as I can have when wearing this blasted corset.”

“Don’t complain to me. You Daughter made me buy dresses which make it necessary for me to wear a ‘blasted corset,’ so if you want to blame anyone, blame Sylvia,” I said.

“But you both look so good,” Sylvia said defensively.

“Sylvia told us that you are dressing as a female all the time during this summer,” Sylvia’s Mon said.

“I had my hair styled with highlights added for the my job this summer, so I couldn’t very well walk around wearing boy’s clothes,” I commented.

“I don’t know about that,” Sylvia retorted, “most of the college girls walk around wearing unisex clothes, but I have to admit that you look better dressed as a girl.”

“So, what do you do with your time off?” Sylvia’s Mom asked.

“I work on music, read, shop, and even go swimming,” I answered, “I found this delightful one-piece suit with a little skirt on the bottom to cover up a certain area.”

“You’re going to have some interesting tan lines by the end of the summer,” Sylvia chuckled.

“I’ll deal with that when school starts,” I responded.

“Like how?”

“Maybe a tanning booth, topless, I guess.”

Sylvia’s Dad was looking at me. “Do guys ever hit on you? The reason I ask is that when my wife and I go out with me wearing a dress, I get hit on. How do you deal with that?”

“I tell them that I have a very jealous lover,” I answered with a smile.

“Darn tooting,” Sylvia interjected.

“What do you do?” I asked Sylvia’s Dad.

“I tell them that I’m married,” he answered.

* * *

It was later that week that I got a call from Mr. Nicholas. “I hear you’re doing well at the restaurant. Any thoughts about another CD?”

“I can come to see you on any Monday or Tuesday,” I said. “I also have written some new songs, and I can bring the scores with me.” We arranged that I would come over a week from Monday.

* * *

One evening while I was performing, I threw in ‘Parlez-moi D’Amour.’ This caught the attention of a group who turned out to be a committee of professors. They were at the college to plan a symposium on French nineteenth century literature. As I was ready to take my break, two of them came up to me. “Great song,” one of them said. The other asked, in French, how I came to know the song. Of course I responded in French. I added that I was a French literature major. They all liked this and a discussion of French literature ensued.

One of them picked up one of my business cards and said, “We’re planning a symposium here over the Christmas holidays, and we wonder if you would be available to play for the reception,”

“We had planned to play a CD during the reception, but live music would be better,” another one said. He turned to the rest of the committee and asked, “Do you have that CD?”

Just then a man got up from the table with a CD in his hand. Surprise, it was Bob’s Father. He looked at me and began to laugh. “If you want to know if she knows these songs,” he started, holding up the CD, “look closely at the CD and her. This is her CD.”

After the break, I played and sang each song from the CD and added a few extras. I was hired for the symposium gig. They all stayed to listen until I was finished at nine. After that, Bob’s Father came up to me to chat. He volunteered that he, his wife and maybe even Bob would be at the symposium. It would be nice to connect with Bob, since I had previously pretended to be Bob’s girlfriend to deflect some grief Bob was receiving because he was gay, and I wanted to know if his parents were still giving him grief.

Chapter 45 - Some Changes.

It was in July that Sylvia visited me for a weekend. After some passionate lovemaking, Sylvia and I were lying in bed, naked. She was looking at my chest. “Your nipples and areolae look bigger than I remember,” she said.

“Yeah,” I replied, “and they are more sensitive.”

“Have you seen a doctor?”

“I called my Mom. She called her Doctor, and the Doctor ordered some blood and other tests. I can have the tests done here and the results sent to my Doctor. I have an appointment to see the Doctor a week from Monday. I’m seeing if I can make an appointment with my counselor the same day.”

“Have you thought any more about whether you want to transition?”

“I’ve thought about it a lot, it’s just that I haven’t come to any conclusions.”

“How come?”

“I like our lovemaking too much.”

* * *

I saw the Doctor. “Well, your hormone imbalance has shifted a bit. Nothing to be alarmed about, but your estrogen level is higher that when we had our last test. Have you noticed any other changes?”

“It takes me longer to get aroused, and when I am, it doesn’t seem quite as hard.”

“Are you getting attracted to boys?”

“No, not really,” I answered, “Sylvia and I have remained very close.”

“Have you kissed any boys, or had any sex with them?”

“Except for a casual kiss or so, the answer is no,” I replied, “are you suggesting that I do?”

“No, I just wondered, but if you do, I’d like to know about it, next time you come in.”

She had me put on a disposable examination gown and get up on the examination table. She pulled out the stirrups and I put my feet in them, She then began an examination of my penis and testicles. All of her touching caused an understandable reaction, which did not escape her notice. She smiled, and said, “Well, it seems that everything is working down there. You say your reaction time is slower, and you don’t get as hard. Could you manipulate yourself, so I can see?”

Now I was really embarrassed, but I began stroking my penis. The Doctor stopped me and grabbed my penis to see just how hard it had become. “Maybe this is not the right environment to get you hard.”

She then had me sit up and removed the gown to allow her to look at my chest.

She looked at, prodded and poked at my nipples, which caused them to get bigger and harder. “There’s something there,” she said.

“What?” I demanded to know.

“You’ve got the beginnings of breasts,” she said. “It might be a reaction to the higher estrogen level.”

She then looked at the test results for a few second, and said, “I want you to have the same blood tests toward the end of the year, and see me when you are home from school for the holidays.”

* * *

My playing and singing gathered some interest and I picked up some other gigs. The additional money was welcome.

I kept myself busy over the summer, and at last I noticed that Labor Day was quickly approaching. I saw that the words ‘Final Week’ were added to my poster. I had dressed as a girl all summer. It was just easier for me, and frankly, I liked it. I had been hit on more times than I could remember, but because of the watchful eyes of the bartenders, nothing bad happened.

It was with some sadness and regret that I visited the salon after my gig at the Carleton House was over. I had my hair dyed to get rid of the highlights, and to get a style which could be a male style. Gail showed me how to switch my hair from a girl style to a boy style and back again. “I’m going to miss our Wednesday afternoon sessions,” she said. I told her that I also would miss them, but I would be back from time to time for a trim and maybe something more dramatic.

Chapter 46 - The Apartment.

All of the apartments in town were on a one year lease, tied to the school year. This meant that the girls would have to pay the rent for their apartment over the summer even though they were not at school. One Sunday afternoon, the girls and I discussed the apartment. “None of us will be here over the summer,” Sue said to me, “but you will. If you could pay half of the rent, the rest of us will kick in the other half, even though none of us will be here.”

“Ann’s graduating, but the other three of us would like to keep the apartment, so we plan on signing a new lease for next year,” Sylvia said, “We’ll be looking for a fourth girl to live here and share the rent. We’d like you to show the apartment to any new students while you’re here.”

“What about Frank?” Ann asked, “he’s not expecting you to room with him next fall, is he?”

“No, I think that he and his boyfriend will be sharing a room.” The girls all nodded their heads, knowingly.

Since I couldn’t very well stay at the girls’ apartment during the school year, I contacted the building manager for the building which housed the girls’ apartment. There was a studio apartment available. Not only available, but the current tenant wanted to live there until the fall term started, and she would sublease the apartment from me until then.

The apartment consisted of a main room, a small kitchen, and a large open closet which served as a dressing room. The bathroom was connected to the open closet. There was a built in bed which was behind some doors in the main room and which folded down at night.

I met with my sub-tenant at the apartment. All of the furniture was used, and somewhat worse for wear. There were some things that she wanted to either sell or, if she couldn’t, she would take with her. She told me that she definitely was taking her sound system and computer, which did not bother me since I already had my own. We worked out a deal where I bought some of the things and she just threw in the rest.

Setting up housekeeping from scratch meant that I made a lot of shopping trips when I realized that I needed more stuff.

When Sylvia arrived for the start of the term, I naturally had to show off my new digs. She had to see the bed, and commented that it was a double. She also noted that most of the clothes in the closet were my Jean clothes. That evening, she had to try out the bed, and declared it acceptable.

“You really could use a vanity,” she said, after examining the bathroom sink and mirror. “Get dressed, and we’ll go looking for one.” When she said that I was wearing my boy clothes.

“I am dressed,” I declared.

“Not when you are looking to get a vanity,” she countered. She went into my closet and picked out what she thought was appropriate. It consisted of a bra, white capris, a pink top and wedge sandals, all of which she handed to me.

“Take off those clothes and put these on,” she said, and when I did she saw that I was wearing panties under my boy clothes. “Good start,” she said.

It turned out that I convinced Sylvia that I could use my desk as a vanity, and I only had to buy a big mirror with lights around it.

The next day Sylvia returned with garment bags and suitcases, which she unpacked and preempted some of my closet space and dresser drawers. “So I don’t have to go back to my apartment to change,” she explained, “You’re free to borrow any of them, as long as I can borrow some of yours.” This arrangement required that I buy an additional clothes hamper.

Chapter 47 - The Halloqueen Returns.

About a week before the semester was to start, some of the officers of the sororities came to the campus to plan activities for the year. They had heard that I was playing and singing at the restaurant, and on Wednesday they visited the lounge at the restaurant to listen to me. During my break they invited me to sit with them for a few minutes. “Great performance,” one said, “but of course we expected no less from our Halloqueen. We have some things planned for you if you have time. How about a meeting some afternoon?”

I agreed to this and a time and place was set.

It appeared that they wanted me to participate in the new student welcome which would happen the weekend before classes started. “Of course, we have big plans for the Halloween dance,” I was told. “We’re going to miss our darling Halloqueen after that.” They told me that my reign was as good as anyone could remember.

Naturally, my fraternity wanted to get some mileage from me as Halloqueen, so I had activities planned for that, some of which involved me showing some leg. I had no problem with that.

When Halloween rolled around, I did the usual welcome and first dances.

Frank was there, without his lover, and he came up to me. “You’ve remembered to put in a good word for me about joining RLE, didn’t you?” I told him that I did, and I congratulated him on getting off probation. “I couldn’t have done it without you,” he said, and he gave me a brief kiss. I savored that kiss, and stood there to see if he would kiss me again. He didn’t.

Watching the Halloqueen contest was a lot of fun for me, especially since my reign would soon be over. The winner of this year’s contest was actually a girl, and I took great pleasure in putting her sash over her head and crowning her with the tiara.

Chapter 48 - Strange stuff.

I wore boy clothes almost all of the time after classes started, with the exception of my Halloqueen duties, some gigs, and occasional dressing at the request of Sylvia. One weekend her parents visited her. Both her Mom and Dad wore skirts. Her Dad confided that he was wearing a corset I could see that it greatly improved his figure.

They invited Sylvia and me out to dinner, and insisted that I wear a dress. Naturally, that meant that I had to wear a corset. “If I have to wear a corset, you also should have to,” her Dad said. They wanted to go to a nice restaurant, and Sylvia suggested we go to the Carleton House where I had played the past summer. Adele, the usual pianist was there, so we sat in the lounge. When she saw me, she invited me to trade sets with her.

The evening was very enjoyable. I really liked her Parents, and I think that her Dad liked it that I was a cross-dresser.

Chapter 49 - Thanksgiving at Sylvia’s house

I split the Thanksgiving holiday between my family on Thanksgiving day, and Sylvia’s house on Friday and Saturday. After a delightful Thanksgiving meal, my Dad asked me, “Still wearing dresses?”

“Every once and a while,” I replied.

Mother wouldn’t let me say more. “She has to when she performs,” she interjected, “and from the photos I’ve seen, she looks gorgeous.”

“I didn’t say she wasn’t,” my father rejoined. I noted the use of the female pronoun. “I just wanted to know,” he added.

“By the way, tell your Father what the Doctor said,” she said, and I did.

I got up early on Friday morning to get ready for the trip to Sylvia’s house. I took a delightful bubble bath, fixed my hair and put on some makeup. I put on a pleated skirt and a long sleeved blouse with ruffles. Because there was a nip in the air, I wore stockings, along with a corset. While I hauled my suitcase downstairs, I saw my Father in the living room. “You look delightful,” he said with a smile.

I thanked him, and gave him a big hug.

I put on a frocked coat, and took my suitcase to my car, gave my parents hugs and headed off to Sylvia’s house. When I arrived, I noticed that Sylvia’s Dad was wearing a suit. “Mom an I are going to my Aunt’s house today,” he said as an explanation.

“So, no dress?” I asked.

“No dress,” he confirmed.

“We’ll spend the night,” Sylvia’s Mom said, and with a wicked smile she added, “I’m making him wear panties under that suit, and I’ve packed a sexy nightie for him for tonight.”

Sylvia’s Mom had fixed a light lunch, and we ate it at the kitchen table. After clearing it away, we lingered over tea and coffee. Somehow, my appointment with my Doctor came up. The recent developments concerning my nipples was discussed, and I had to strip to the waist so they all could see. I inadvertently let slip that my Doctor had asked if I had kissed any boys. “And you said?” Sylvia asked. I affirmed what I had told my Doctor.

After her parents had left, Sylvia asked, “You must be tired from the drive. I think you could use a nap.” She took my hand and led me to her room. I didn’t get a lot of sleep. That evening we dressed up and went out to dinner, and spent the night together.

I was filling in for Adele at the Carleton House on Sunday so she could spend some time with her family. Halfway in my second hour, I saw Frank, my former roommate sitting in the lounge, alone. I sat with him during my break. “Where’s your main squeeze?” I asked.

“Some of the guys at the frat fixed me up with a date with a girl. It was nothing, just to round out the numbers. However, he didn’t see it that way and pitched a hissy, accused me of cheating, and said he’ll never talk to me again.”

“I’m sorry,” I said.

“It’s not your fault. He’ll miss me, so I expect that things will be alright in a few days.” He paused for a moment, and continued, “You look really foxy tonight. If I wasn’t, you know what, I’d want to kiss you.”

“Is that all that’s stopping you?” I blurted out, instantly regretting what I had said. He leaned over and put his lips on mine. I could feel his kiss all the way to my feet.

* * *

My Doctor’s lab orders arrived in the mail that week. In addition to the usual hormone balance test, there was a test for a sperm count. That confused me a bit, so I called her on the phone about the sperm count. “I wanted to see if there were any other effects from your hormone imbalance,” she said.

“How am I supposed to do this?” I asked.

She chuckled. “Go to the lab, and they’ll give you a container, and you put your ejaculate in it the morning before you to the lab, or you can do it at the sperm bank attached to the lab. I heard they have private rooms with dirty magazines and a comfortable chair,” she added with more chuckling.

When I told Sylvia about this, with a wicked grin she offered to help. I declined her offer.

* * *

I had appointments with Mom’s Doctor and my Counselor for the next Monday, so I drove home for a long weekend. Mother was concerned about my nipples and nothing would do unless she could see them herself. Then she began to touch them. “Mom,” I complained.

“What is it Honey?” she asked, without removing her hand.

”They’re sensitive,” I responded. Her touching had made my nipples enlarged and hard.

“Oh,” she said, finally understanding, and she took her hands away. “Make sure you mention this to the Doctor.”

With a wicked grin, I said, “That they’re sensitive, or that you like playing with them?”

“Hummph!” she grunted.

On Monday morning I decided to wear a skirt and blouse for my visits to the Doctor and the Counselor, but waited until Dad had left for work before getting dressed. Given the situation, I wore a silky camisole under my blouse.

Once in the Doctor’s office, she got right to the point. “Your hormone imbalance is just about the same as last time, even if the physical manifestations are slightly increased.” She had me put on a disposable examination gowns and get on the examination table. She then physically examined my chest. Her touching made my nipples larger and hard. I blushed. “Does the camisole help?” she asked.

“Yes,” I replied, “I like to wear it if I’m not wearing a bra.”

“So you’re still dressing?”

“Yeah,” I responded, “I’ve been doing piano gigs, and for that I only wear women’s clothes.”

She then lifted the bottom of the examination gown, and pushed, pulled and prodded. I began to react to the examination. “Well, things still seem to be working down there,” she said, “The fact that you could get a sample for a sperm count also proves that.”

She then sat down on a stool. “Well, your sperm count is in an acceptable range, if a bit on the low side.”

“Does that mean that I could get a girl pregnant?”

“I think so. Why?”

“I’d like to have children.”

Shortly after the Doctor’s examination, I had a session with my Counselor. We discussed what I had been doing since our last session, and my piano playing came up. “So, you dressed as a woman the whole summer. How did that make you feel?”

“Great,” I said, “since I was playing the piano at the restaurant five nights a week, I had my hair styled and highlights added. I also plucked my eyebrows a bit. I didn’t think that wearing boy’s clothes fit in, so it was just as easy to be a girl for the whole summer.”

“What did your girlfriend think about that?”

“She seemed to like it a lot,” I answered, “it might just be genetic.”

“Why do you say that?” she asked.

“It turns out that her Dad is a crossdresser. Sylvia, her parents, and I went out several times as four females. He Dad and I shared being uncomfortable having to wear corsets under our dresses. My dresses wouldn’t fit without a corset, and Sylvia’s Mom made her Dad wear one when he wore a dress.”

“Very, very interesting,” my Counselor said as she frantically scribbled note on her pad. She then looked at me, and said, “I see you’re wearing a skirt and blouse today. Do you continue to wear skirts and dresses all the time?”

“Hardly, I’m registered as a male at school, so I can’t,” I answered. “But a lot of times I wear panties under my boy clothes,” I added.

“Why?” she asked.

“I like the way they feel, and Sylvia likes it when I do,” I answered.

“She checks it out?”

“Yeah,” I said, omitting to mention how Sylvia checked it out.

She changed the topic, and said, “How do you see yourself after you graduate?”

“I’d like to get married, have children and get a job. To do these things I’ll have to be Eugene, not Jean. After all my diploma will have my male name on it.”

“Are you telling me that you will stop cross-dressing?”

“Heavens no!” I responded, “I’ll continue to dress when I can.”

She consulted her notes and said, “You previously told me that you weren’t dating boys. Has that changed?”

“No,” I responded, “I only date Sylvia.”

“Then do you feel that you might be a lesbian?”

“Not really.”

“Have you kissed any boys?”

“Yeah, a few times.”

“Anything further than that?”

“No.”

“I only ask that to see if you have any homosexual tendencies, but with your limited experience, we can’t come to any conclusions.

* * *

I related my counselor’s statements to Sylvia. She surprised me when she said, “Maybe you should go on a date with a boy.”

“Wouldn’t that bother you?”

“Of course it would,” she said, “but I think we should know your reaction. It might be possible that you are bisexual.”

“But I don’t know any boys, at least not well enough to do that.”

“How about Frank?”

“I don’t think his boyfriend would stand for that,” I said. I paused in thought for a minute. “Maybe Bob?” I said.

“Who is Bob,” she challenged.

“Back in high school, Sandy, my then girlfriend, had some friends who knew this guy, Bob. Bob’s gay, and was getting a lot of grief from his parents. It was set up that I would dress and go on a pretend date with him, so his parents would see him going out with what they though was a girl.”

“And. . . ?” Sylvia said, looking for more details.

“It worked, and after our pretend date, Bob’ Parents invited me to a family gathering to show me off. Bob’s Dad is a professor and teaches French. I ended up playing the piano and singing in French. Well, it turns out that Bob’s Parents are attending a symposium on French literature over the holidays, and heard me sing at the Carlton House. So I am hired to play and sing at a reception for the symposium attendees, and it turns out that his Parents are dragging Bob along to the symposium.”

“So you could spend some time with him. I suppose?”

“Yeah.”

“And maybe some kissing? Maybe something more?” Sylvia asked.

“I don’t know,” I said, “it might be a total disaster.”

“But it might not,” Sylvia said. “He does know that you’re a boy, doesn’t he?”

“Yeah.” I answered.

“But that probably wouldn’t bother him since he’s gay,” she said.

“But what about me?” I asked, “what if I like it?”

“It doesn’t necessarily mean that you’re gay, you might just be bisexual, after all, you seem to like our time together.”

“I do,” I affirmed.

“Then go ahead, and give him a good kiss, with a lot of tongue,” she said, “and by the way, put some condoms is your purse, just in case,” she added with a leer.

I gave her a dirty look.

* * *

Chapter 50 - Christmas break

I had some gigs playing for Christmas parties. It turned out that I couldn’t head for home until Christmas Eve, and could only stay for Christmas Day, since I was heading off to Sylvia’s house the next day. Even that time was cut short since I was preforming at the symposium.

Christmas at my home was nothing out of the ordinary. My sisters seemed to treat me like a girl. I woke up early in the morning and headed off to Sylvia’s house.

Since I had to head back to campus the next day, I spent the night at Sylvia’s house. I had expected to sleep on the couch, but Sylvia’s Parents surprised me with their Christmas gifts. They gave me and Sylvia matching night gowns. When bedtime rolled around, no one made any move to fix the couch for the night. Both of Sylvia’s Parents smiled when Sylvia led me to her room, and as we climbed the stairs, Sylvia’s Mom said, “Before you hop in bed, we would like to see how the nightgowns look on both of you,” It appeared that her Parents had no problem with Sylvia and I sleeping together.

* * *

I had scheduled a visit to the salon for the early afternoon, so I had to leave Sylvia’s house shortly after breakfast. I wore hose and a corset under a skirt and blouse. Gail met me at the door of the salon. “Another gig?” she asked/

“Yeah, I’m playing for a reception for a symposium of college profs,” I answered, “The topic is French literature from the nineteenth century, so I think a french twist would be an appropriate hair style.” I also had the salon do my makeup.

Suitably glamorous, I then went to my apartment to get dressed for my gig. I chose a deep red dress with a hem that was well above my knees and with a slit on the left side. I also wore a black corset, black stockings and a pair of black control panties, along with black court shoes with a two inch heel. For jewelry I wore only two rings, but no bracelets, because they interfered with my playing. I did, however put on a necklace and earings which sparkled.

The symposium was being held at a local hotel, and I arrived about an hour before my gig started, because I wanted to check out the piano and where it was located in the room. I also wanted to see if there was a microphone, because I suspected that the committee might want me to sing. After I finished this, I went in search of a place to relax until my gig started. However, I wasn’t able to do much relaxing because shortly after I sat down, Bob and his Parents came into the hotel lobby, and headed straight to me. After the usual greetings, Bob said that I looked particularly gorgeous, and I smiled in return. Bob noted my coat on the chair next to me. “I’ve got a room,” he said, “maybe you’d like to put your coat in it to keep it safe?”

“As long as I know where to find you when I’m ready to leave,” I answered.

“Don’t worry, I’ll be near you all evening,” he responded. So we went up to his room to deposit my coat. When we were in his room, I asked where his parents were staying. “On another floor in a different wing,” he said with a leer. With that he put his hands on my shoulders and drew me closer to him. I appeared that he was getting ready to kiss me.

“Hold on,” I said, pushing him away. “I don’t want to mess up my makeup.”

“Then maybe later?” he said with an inviting smile.

“Maybe, and then again, maybe not,” I said coyly.

There were quite a few people in the reception room when Bob and I entered. I quickly went to the piano, or at least as quickly as my dress would permit. While doing so, the slit in the skirt opened up a bit, drawing some appreciative looks from some of the men present. I smoothed out my skirt under me and sat on the piano bench, and immediately began playing.

Bob’s Dad came up to the piano. “Are you going to sing, too?” he asked in French.

“If that’s what you and the committee want me to do,” I replied in French. “Any requests?”

“Anything from your CD,” he answered, also in French.

“Okay,” I replied, naturally in French, “I have also practiced some french music from the nineteenth century.”

“How appropriate,” he said.

So I played and softly sang, since I was only providing background music. Whatever my intention was, I noted that I had attracted a group of admirers, mainly men. The didn’t talk, they just listened.

I was surprised when I saw my high school French teacher, Mlle. Vert was present. She came over to the piano and smiled at me. “It looks like your class project may have started something,” she said, with a chuckle.

“I guess so,” I replied, “I’ll explain it when I have a break.”

Bob, true to his word, stayed close. He stood to my left, which gave him a good view of the slit in my dress and what it revealed.

I was really enjoying myself, and the time seemed to fly. Finally, a member of the committee came up and took the microphone and announced that dinner was ready to be served. He then announced, “The committee and I want to thank Mlle. Jean for her music. I hope you note that she specially gave us quite a bit of French music from the nineteenth century.”

As the crowd was filing out for dinner, Bob’s Mother came up to Bob and me. “I don’t know what your plans are, but if you’d like, you and Bob can be our guests at the dinner.”

“That is very kind of you, but I was thinking of taking Bob to the Carleton House for dinner. I played cocktail piano there most of the summer, and I was thinking that Adele, the regular pianist and I would trade off sets.” With this, Bob had a big smile on his face.

“Well, I can understand,” Bob’s Mother said, “That sounds a lot more interesting than the dinner and speeches.” Her smile at us spoke volumes. She wanted to encourage a romance between Bob and me.

We then went up to Bob’s room to retrieve our coats, but once inside with the door closed, Bob again put his hands on my shoulders, and drew me close to him. “If only she knew . . .” he said with a smirk. He lowered his head and pressed his lips to mine. I returned his kiss, and we played tongue tag with each other. When he held me close to him, I could feel that he was getting aroused. Luckily, I had tucked and was wearing control panties, so he couldn’t feel me getting aroused.

We broke the kiss for a few moments, and I said, “I thought you only went for boys.”

“That may be true, but I have on good authority that underneath your feminine beauty lurks a boy,” he said softly. We kissed again.

“You kiss like you are turned on, but the rest of you says otherwise,” he whispered.

“Tucking and control panties,” I laughed in his ear.

He reached behind me, and began to unzip my dress, slowly, as if waiting to see if I objected. I didn’t.

We separated and he helped me pull my dress over my head, and followed it with my slip. He looked at my crotch, but there was no sign of male organs aroused or otherwise.

“Control panties?” he questioned.

“If you spent more time with girls, you would know,” I said. With that, he hooked his thumbs into the waistband of my control panties and began to slowly slide them down, again waiting to see if I objected. There was no objection, and when my panties were partway down, a part of my anatomy revealed itself. He pushed me down on the bed and kneeled down between my legs. I grabbed my purse, opened it, and handed him a condom.

When he and I were finished, he stood up and began to remove his pants. “No,” I said, “I don’t know if I’m ready for that. Anyway, I want to take you to dinner.”

I got dressed, and went into the bathroom to repair my makeup. “You need to clean the lipstick from your face,” I suggested to him.

When we were again respectable looking, we took our coats and headed out to the Carleton House.

* * *

The lounge at the Carleton House had a good crowd, but I was able to arrange to eat in the lounge, near the piano. Adele saw me and invited me to trade sets with her. I introduced Bob. During a break, Adele and I went to the washroom together. “He’s a nice looking boy,” Adele commented.

“I met him when we were in high school. He’s here with his Parents; They are attending a symposium. I played at the reception, and I’m rescuing him from some after dinner speakers.” Adele then looked at the slit in my dress.

“It looks like he might need someone to rescue him from you,” she said with a smile.

“I don’t think he wants to be rescued,” I replied.

Bob and I sat next to each other on a banquette at our table. When I returned from the restroom, I sat to his right. Shortly after sitting, I felt his hand move up the slit in my dress and rub my thigh. I left it there for a while, enjoying the experience. I then dropped my left hand under the table to move his hand away. However, when I grabbed his hand he moved both of our hands to his lap. “You turn me on,” he whispered.

“Obviously,” I whispered, confirming what I had felt. “Behave yourself,” I added, and we both moved our hands to the table top.

We stayed until Adele was finished with her gig. “Want me to drop you off at the hotel?” I suggested.

“Only if you go in with me,” he responded.

“No,” I said, “I don’t want to be seen leaving your room by myself.”

“Okay, then where?”

I didn’t want the evening to end. I really wanted another kiss. “How about my place?” I suggested, immediately realizing what I had said.

“Sounds good to me,” he said with a leering smile.

* * *

When we arrived at my apartment, Bob looked around. “Cozy,” he commented.

“I don’t need a lot of room, just for myself,” I said.

“No roommate, then?”

“No,” I answered.

“I need to use the washroom,” he said, “where is it?”

“This apartment isn’t very large,” I replied snidely, “it shouldn’t be that hard to find. Go through the dressing area,” and I pointed the way.

He couldn’t help but notice all the skirts and dresses in the dressing area. “You’re really into this girl thing,” he commented.

“They’re not all mine,” I said, “some belong to my girlfriend Sylvia.”

“Interesting,” he said, leaving volumes unsaid.

“I have some soft drinks, or maybe you’d like tea or coffee?”

“Coffee sounds great,” he responded, and with that I went into the kitchen area and started some water for the french press. When I came back, he was sitting on the couch.

“Sit down next to me,” he said patting the cushion to his right. When I sat down, he put his hand on my leg and began to rub, moving his hand up the slit in my dress. He took his other hand, put it on my shoulder and pulled me to him. Our lips met.

We then embraced each other, our tongues dancing in each other’s mouths. It was wonderful. The thought crossed my mind that I’m a boy and I’m kissing another boy, and I really like it. What does that mean? What am I?

Bob’s hands move to his belt, and he unfastened it and then opened the zipper in his pants. I just watched. He lifted himself up a bit, and pulled his pants and underpants down. He was totally aroused. He took my hand in his and put it on his manhood. This was a new experience for me.

“I know that you want to kiss it and lick it,” he said softly, and I did. I liked it.

When that was over, we kissed again and again. “I never did that before,” I confessed.

“It wasn’t so bad, was it?” he said, and without waiting for an answer, he continued, “and I bet you enjoyed it.”

“Yes,” I said softly.

“Then let me reciprocate,” he said, and unzipped my dress.

We did it again, and after cuddling for some time, we both got dressed and I drove him back to the hotel. As I was letting him out of the car, he said, “I’d love it if you became my boyfriend. There are other things we can do to each other, which are a lot of fun.”

“I don’t think I can,” I replied, “I have a girlfriend, and I’m in love with her,” I added.

Chapter 51 - Revelations.

I really didn’t know what I would tell Sylvia about what happened. I felt that I had cheated on her, and to make matters worse, it was with a boy.

I didn’t have anything planned for the time until classes resumed after the Christmas break, so I drove to Sylvia’s house to spend a few days with her and her parents.

The KGB had nothing on Sylvia when it came to interrogation. After dinner one evening we were sitting on the couch. “You didn’t tell me about your playing the piano for the reception for the symposium,” she started out.

“I was okay,” I answered, “they all seemed to like it, and best of all not only did I get paid, but I got a very generous tip.”

“You mentioned that Bob might be there,” she continued, “so was he?”

“Yes.”

“And how did that go?”

“I took him to the Carleton House, and I traded sets with Adele. He seemed to enjoy it.”

“Did you kiss him?” I started to blush with embarrassment.

“Well, kind of,” I answered.

“There in no ‘kind of’ when it comes to kissing,” she asserted, “either you did or you didn’t. So which was it?”

“I kissed him,” I confessed. “After what my Doctor said, I wanted to see what it was like.”

“Okay, what was it like?”

“It was okay,” I muttered.

“You’re holding out on me,” she said, “either you tell all, or it’s going to be a frigid night tonight, and for the foreseeable future,” she threatened.

“Okay, okay,” I responded, “it was nice; I actually enjoyed it. It was better than I thought it would be.”

“Better than kissing me?” she asked menacingly.

I could see that there could be only one answer. “No, it’s a lot better kissing you.”

“I don’t know if I believe you, but we’ll let it slide,” she said, “anything more than kissing?”

I was on dangerous ground here, and didn’t make an immediate answer. Sylvia took my delay as an admission that there was more.

“Oral sex?”

“Yeah,” I finally admitted.

“By you or by him?”

“Both, it kind of just happened.”

“And did you enjoy both?”

“Yes,” I admitted.

“Would you do it again?”

“I don’t know,” I said, “after all, I’ll probably never see him again.”

“It doesn’t have to be with Bob,” she said, “after all, you could connect up with Frank.”

“I don’t think so. When Bob and I did it, I felt like I was cheating on you, and I didn’t like that feeling.”

Sylvia smiled. “That answers some questions. I think that you are a crossdressing bisexual,” she concluded.

“How do you come to that conclusion. After all you don’t know any crossdressing bisexuals to compare me with.”

“On the contrary,” she asserted, “I do. My Dad is one.”

“Okay, so he crossdresses,” I commented, “but bisexual? How do you know?”

“My parents told me,” she answered.

“Is your Mom okay with that?”

“She is, as long as she knows with whom he has sex. She doesn’t want him trolling around gay bars and having one night stands.”

“I’m still astonished,” I remarked, “But I think I can see her point.”

“Do you want to know who she thinks is a suitable partner for him?”

“Who?”

“You.”

“That’s just too weird,” I said.

“But you would?” she asked.

“You can’t be okay with it, can you?” I asked, avoiding answering her question.

“As strange as it seems, I am,” she said, “so, answer my question, would you?”

“I guess so,” I reluctantly admitted.

“Great,” she exclaimed. She stood up and pulled me up with her. We went upstairs to her room. “Put on that nightgown you got for Christmas,” she said. “I’ll be right back.”

When she came back I was wearing the nightgown. She didn’t come back alone; her parents were with her. Her Dad was wearing a nightgown and had a big smile on his face.

Sylvia and her Mom were also smiling. They turned around and headed for the door, leaving me alone with her Dad. “Have a good time, you two,” her Mother said as she closed the door.

Chapter 52 - Marriage

Later that week, I proposed to Sylvia, and she accepted. I knew that she, like I, wanted children, which ruled out any thought of me transitioning. As she said, I was getting into a weird family, but it was one which accepted my crossdressing and bisexuality. When I told my family I conveniently left out the part about Sylvia’s Dad and me.

Sylvia, her parents, and I celebrated the engagement as four ladies going out to dinner. During dinner, I saw Sylvia and her Mom playing scissors, rock and paper. Naturally, I was curious. It turned out it was to determine with whom I would be spending the night.

Calling Sylvia’s family ‘weird’ would be an understatement, but I fit right in, a crossdressing bisexual.

The end.

How Romeo and Juliet Changed My Life

Author: 

  • Pentatonic

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

How Romeo and Juliet Changed My Life


By Pentatonic

TG Themes: 

  • Voluntary

TG Elements: 

  • Estrogen / Hormones

How Romeo and Juliet Changed My Life - Part I

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Estrogen / Hormones

Other Keywords: 

  • Hormone imbalance
  • Family Problems
  • boy kissing boy

Permission: 

  • Posted by author(s)

How Romeo and Juliet Changed My Life
By Pentatonic

Part I.

Chapter 1 - Up in Smoke.

I’m Stephen Spicer, ‘Steve’ to my friends. I was born on April 15, 1998. My best friend, David Hurst, was born seven days thereafter. We lived a couple of blocks apart and we had been friends ever since we started school together. I’m rather small for my age. Puberty and my growth spurt still hadn’t shown up by my 16th birthday. Dave, on the other hand was average height and weight, handsome with black hair and a winning smile. Aside from getting along, there was another solid reason for our friendship, Dave was only a ‘C’ student, and I had tutored him all the way through school. As a result of this I really knew the course materials of our classes, and I was nearly a straight ‘A’ student. I guess that I was considered to be somewhat of a nerd. Neither Dave nor I went out for any sports

Dave was very popular with the girls. Not the same for me. While I had a lot of female acquaintances, there was no spark of romance involved. I hung around with the girls; Dave dated them.

It was the summer before our junior year. Dave and I considered ourselves lucky. We had lined up summer jobs at “Barrels of Fun” amusement park. Both of us had recently turned 16 and this would be our first real jobs. I had to thank Dave for that, he was the motivated one and had convinced me to go to the park and apply on the day that they started accepting applications back in March.

The park was scheduled to open on Memorial Day and stay open until Labor Day. Like us, most of the employees were high school kids, as were most of the patrons. Neither Dave nor I knew exactly what we would be doing, not that it mattered. The main thing that mattered was that we had jobs, even if they were minimum wage jobs. Dave’s and my goals were alike; to each earn enough to buy a used car and pay the insurance. The fact that we had jobs lined up kept our parents off our backs.

Then disaster struck. The first indication was the sound of sirens. The second was a red glow in the sky in the direction of the park. I called Dave. “There must be a big fire, do you know what it is?”

“Yeah, Steve, I just heard. It’s at Barrels.”

“I hope it’s not bad,” I replied, thinking of my summer job.

It was. The roller coaster was all wood. It had caught fire and collapsed, causing the fire to spread to the carousel, some other rides and the midway.

On Saturday, Dave and I rode our bikes out to the park. All that was left were piles of charred wood and debris.

Bummer, I thought. Mid May and my summer job had gone up in smoke, literally. “Now what do we do?” I asked Dave.

“I donno,” he replied, “maybe look around for another job?”

“Fat chance,” I said. “We were darn lucky to get the jobs we did. By now, I’m sure all the summer jobs are gone.”

“Yeah,” he muttered. “Looks like we’ll be riding the ‘green limousine’ all year.” The municipal buses were painted a sickly green color. “We’ll probably have trouble getting a date if it means the bus, bicycles or walking.”

I expected some degree of sympathy from my folks. No such luck. “Well, you better get your butt in gear and find another job.” Yikes, it wasn’t like I had set the fire.

There was another alternative to a summer job. Laughton Academic Achievement Camp. It sort of sounded like year round school. My parents had heard about this place and had received a brochure. Five hours of classroom work each day, and three hours on Saturday. It was run by a religious college that wanted more revenue and utilization of its campus, a campus which was located in the middle of corn fields. It did have an indoor swimming pool, tennis courts, an auditorium which served as a chapel, and a gymnasium, but that was about it. They even scheduled things for our “off” hours. ISports all Saturday afternoon, chorus on Sunday afternoon, and, you guessed it, religious services all Sunday morning.

“Well, if you don’t find a job in the next week, we’re sending you to the camp,” my mother declared, waving the brochure in my face threateningly. “If you can’t earn money, you might as well improve your mind,” she said.

The job search began immediately, but in vain. No burger flipping jobs, No grounds work available at the cemetery, no pizza delivery jobs without a car and insurance. Nothing. Nada. The deadline for camp applications loomed closer and closer, until it arrived. The application went in, sealing my fate for the summer. Since I was an A student in school, there was no chance of rejection based on grades.

In due time, the acceptance package arrived from the camp. My parents poured over it, gleefully pointing out things that they knew I wouldn’t like. No personal vehicles. No girls. No place to go, no inappropriate music, good grooming, mandatory church services, mandatory chorus, and a host of other rules.

“Maybe you want to get a haircut before you go,” suggested my father. I was allowed to have shoulder length hair as long as I kept my grades up.

“You mean like a tonsure?” I responded sarcastically.

“Don’t be flippant,” my mother said. “We’re only trying to help.”

I kept my mouth shut.

One positive thing was that Dave’s parents enrolled him in the same camp, and we could be roommates.

* * *

The day of doom arrived and Dave and I were loaded into Dave’s parent’s car for the hour trip. Upon arrival, I was given my class and activity schedule. I noted a slot for “PE or Drama Class.” Since I am slightly built, PE in high school had been less than pleasant. I asked, and was told, that I could enroll in drama class as an alternative to PE. I had no idea what was involved, but I knew no matter what it was better than PE.

It also appeared that because of my academic record I was placed in advanced classes, some of which supposedly earned college credits. That was the good news. The bad news was that I didn’t share a lot of classes with Dave.

“Hey Steve,” Dave said, “too bad we don’t have a lot of the same classes, since I was hoping that you could tutor me.”

“Let me see your schedule,” I said. From what I saw, it appeared that I was at least familiar with the subject matter in those classes. “I should still be able to help you,” I added.

After looking at his schedule, I noted that Dave opted for drama rather than PE. “Well, at least we both have drama. It says that we will put on a production. That ought to be neat.”

“Do you think we’ll get any roles?” Dave asked.

“I donno,” I replied. “We don’t even know the name of the play. Probably we’ll only get minor walk-on ones, at best.”

“That’s okay,” he said. “I’m only taking drama to get out of PE and away from some of the neanderthals I’ve seen here.”

We arrived at the drama class a little early and were met by at the door by Mrs. Benson, the drama teacher. We gave her our names and she checked us in. A second later she looked at us if she was examining livestock at an exhibition. “Very good,” she said. “Have either of you acted in any plays before?”

“Yeah, both of us,” Dave answered.

“Even better,” she said. “I think I’ve got one of my problems already solved,” she said to herself. She didn’t elaborate, and we had no idea what she meant. That came later.

When all of the drama students had finally walked into the room, Mrs. Benson welcomed everyone and said, “In addition to the general study of drama, we’re going to produce a staging of Romeo and Juliet. Now I know that this is an all boy’s school, but before you start moaning about it, you should know that in Shakespeare’s day no women were allowed on the stage. All female parts were played by boys.” Dave and I had studied this play in English class, so I had a general idea what was going to happen. I began to get a funny feeling about this.

“I want to run through some dialog to see what talent we have here. We’ll start out with part of Act 1, Scene 5, where Romeo talks with Juliet. I need a Romeo and a Juliet. Any volunteers?”

Dave raised his hand. “I’ll do Romeo,” he volunteered.

“Any Juliets?” Mrs. Benson asked, all the time staring at me. “No volunteers?” She said. “Well, I’ll just have to pick someone.” The funny feeling I had just got worse.

“Steve, will you read Juliet’s part?” she asked, more as a command than as a question.

To be truthful, I was glad to play Juliet. It’s just that I didn’t want to seem eager to do it. Since I was little, I always wanted to dress as a girl, to behave as a girl, to be a girl. Now I would have my chance. I didn’t say anything. I just picked up the script and walked to the front of the room where Dave was already standing.

“We’ll start with where Romeo approaches Juliet and says: ‘If I profane with my unworthiest hand this holy shrine, the gentle sin is this: My lips, two blushing pilgrims, ready stand to smooth that rough touch with a tender kiss.’ Now, isn’t that a cool pickup line?” Everyone chuckled

“Start whenever you’re ready,” she said, when the class quieted down. “Read up to the part where the nurse appears.

Dave and I read. We got to the following part:

“ROMEO: Then move not, while my prayer's effect I take. [Kisses her.] Thus from my lips, by yours, my sin is purged.

“JULIET: Then have my lips the sin that they have took.

“ROMEO; Sin from thy lips? O trespass sweetly urged! Give me my sin again. [Kisses her.]

“JULIET: You kiss by th' book.

I certainly didn’t expect Dave to actually kiss me, but he did. The first kiss shocked me. By the second kiss, I was ready, and kissed Dave back. I smiled. I discovered that I liked kissing Dave.

Mrs. Benson and the rest of the class were surprised. “Well, that was something. It was nice but you didn’t need to be so dramatic. Okay Dave, you can sit down.”

She called for another volunteer to read Romeo’s lines. When she did, I moved to sit down. Before I could, she said, “No, No Steve. You stay here and read Juliet’s lines again. You can forego the kisses, however.”

After the class Dave and I were walking back to our room. “It appears that Mrs. Benson has cast the part of Juliet,” he said with a smirk. We said nothing until we were back to our room.

I closed the door behind me. “What was the idea behind the kisses?” I demanded to know.

“I donno,” he said, “I was just following the script.”

“You didn’t have to grab me into your arms and kiss me,” I said. “You could have done something else.”

Dave made a funny face at me, pouted his lips and asked, “Like say, ‘kiss, kiss’ and stood where we were? But that wouldn’t have been any fun,” he replied.

He just stood there looking at me for what had to be several minutes. Neither he nor I said anything.

Finally he spoke. “You may not know it, but you do look like a cute girl.” I gave him a dirty look, but I knew he was right.

“Don’t get mad or anything, but do you remember when we were five and you liked to play ‘house’ where you were the mommy I was the daddy and Tiffany was our daughter?”

I nodded my head, and remembered.

“Do you remember that you insisted that we kiss whenever we played that I came home from work?”

“Okay, so what?”

“Do you remember when you said you wanted a doll for Christmas, but got a baseball glove instead?

I remembered. Heck, I still wanted that doll.

Do you remember when we ‘graduated’ from pre-school and you couldn’t understand why you couldn’t wear a frilly dress like the girls did?

I remembered that it seemed so unfair at the time. Heck, it still was unfair. I nodded.

“Do you remember when we, or at least I, discovered girls, and would talk about them?”

I nodded again.

“Do you remember looking at the girls in their frilly party dresses, and you said you wished you could wear one?”

I nodded again. I still wished that I could wear a frilly dress, but when I mentioned it to my parents they got angry and told me to never mention it again.

“Do you remember that you said that you thought you should be a girl?”

“Yes.” That was the heart of it

“We’re friends, and if you want to be a girl, then as far as I was concerned you are a girl. Heck, you’re pretty, like a girl. When we kissed at play practice, it brought to mind that I’ve wanted to kiss you for several years,” he confessed. “I really liked kissing you today.” Maybe I should have been bothered by this, but I wasn’t, so I didn’t respond. I admitted only to myself that I really enjoyed Dave’s kiss.

Finally, I said, “If you wanted to kiss a boy, then you must be gay! I never even suspected it!”

“No, I don’t think I am. I like girls. It’s just that you look and act a lot like a girl. Remember, you kissed me back, so you shouldn’t be saying who is or who is not gay.

I waited a moment. “Does that mean you want to kiss me again?

“Yes.”

“Then go ahead,” I said, and I put my arms around his neck and pulled him close to me. He responded by putting his arms around me and held me tight. I felt his lips against mine. I could feel his tongue touching my lips. I parted my lips slightly and his tongue moved past my lips. His kiss was wonderful.

We finally released each other. “I hope you enjoyed that because there will be no more kissing, or anything else in this room.”

“Never?” he asked.

“Never,” I said emphatically, even thought I wasn’t quite sure about that.

* * *

It turned out that Mrs. Benson cast Dave as Romeo, so there had to be stage kissing. I hope no one noticed that our kisses were more than stage kisses.

It came time for costume fitting. Mrs. Benson had measured us and ordered costumes for everyone. Naturally, mine was a dress. While everyone else was disrobing to try on their costumes, Mrs. Benson called to me, “Maybe you’d like to use my office to try it on. I did.

When in her office she said, “I ordered some of the underwear that goes with the costume, if you’d like to wear it. Seeing the way you perform the part makes me believe that you would. Although not part of the costume, I bought you some panties and a bra to help you get into the part. Would you like to try them?”

I did. The costume came with a long chemise, which I put over my panties and bra. Next came socks and shoes, followed by a hoop cage and the corset, A corset cover went over this. Even though 16th century women didn’t wear underware, there was a pair of drawers included with the costume for modesty. The bodice of the costume had a square cut neckline, with long sleeves puffed at the shoulders. For the ease of changing costumes, this one had a zipper in the back. Then I put on the skirt, which was made to look like it had an under skirt and an over skirt. The bodice covered the waist of the skirt. I swirled and watched the skirt move. Since my hair was only shoulder length, a wig came with the costume. I loved it. I felt like a woman.

Mrs. Benson looked at me with admiration. “If I didn’t know it, I would never guess that you are male. You have a girl’s face and you make a very pretty girl. We’ll leave the makeup for the dress rehearsal. Now lets get the beautiful you to the rehearsal.

The entire cast was amazed when I entered the room. I knew that I looked better than all of the other guys playing girl parts. Most amazed was Dave.

“Holy Cow, Steve, You look fabulous.” We ran through the play, and when it came time for Dave and me to kiss, we didn’t fake it; we did it with ardor.

On the night of the performance, Mrs. Benson gathered us in a room off of the stage. “I want you to know that I am both pleased and impressed with your efforts in this production. For those of you who don’t already know, we invited all of your parents to the performance. Now go out there and break a leg.”

Maybe because Dave and I had known each other so long, or because we natural actors, we put on a great performance, especially the kisses. It actually stopped the action while the audience ‘oohed’ and applauded after each kiss.

I couldn’t see out into the audience so I didn’t know if my parents were there. I didn’t know how they would take it with me being a girl. I decided that immediately after the last curtain call I would hurry backstage and change into my “regular” clothes.

No such luck. First were the curtain calls. When I stepped out on stage, I was greeted by applause and whistles. I curtsyed like any refined 16th century woman. Dave and I, individually and as the leads had multiple curtain calls. When I left the stage most of the faculty were there to compliment us. Most of the cast went into the auditorium to mingle with the audience while still in costume. I didn’t think that this was the right thing to do and finally I was able to make my way to the dressing room. . . . .

. . . where my parents were, smiling broadly.

“Great performance, Steve,” Dad said. “You’re a good actor, and we loved the performance. We’re so proud of you. I don’t like the girl part and the dress, however.”

“Ohh, let me look at you,” Mom said, “Give it a swirl.” After swirling, Mom added, “You are so beautiful, I can hardly believe that you are our son, you look like you should be a daughter, and a beautiful daughter at that.” Dad frowned.

“Playing Juliet wasn’t my idea,” I said. “Mrs. Benson did the casting and this is what I ended up with. Probably chance had a lot to do with it.”

Just then Mrs. Benson came up behind me. She said, “It wasn’t chance, it was pure talent and a lot of energy which I spotted from the start. You son is just too modest. And you are right, he, or should I say ‘she’ is one of the best looking Juliets I have ever seen. She is more than beautiful, she is gorgeous.”

My father didn’t look pleased with Mrs. Benson’s use of pronouns, but he said nothing. My mother was not bothered in the least. She turned to my father and said, “She reminds me of myself when I was a teen, don’t you agree?”

“Yes dear.” It was the only safe answer to that question.

I decided to chance it. I turned to my mother. “Don’t you think I make a pretty girl?” I asked.

“Of course dear,” she replied.

“Would you mind if I dressed as a girl from time to time at home?”

“Well, maybe, if you really want to do it. I’m not sure that your father would agree,” she said.

“I don’t agree!” He said, emphatically.

“Then maybe I could do it when he’s not at home,” I suggested confidentially to my Mother.

“Let me think about that,” she said. That usually meant ‘No’ when my mother said it.

There was one final drama class before the end of camp. Mrs. Benson was giving us her critique of the performance and the class in general. At the end of the session, she came up to me. “If you have a few minutes, I’d like to talk with you, in private.” I followed her to her office.

“First I want to say that you’ve been one of my best students for many years. You really got into being Juliet. You and Dave had a lot of energy between you, and you transmitted it to the audience. Furthermore, when you and Dave kissed, you could almost see the sparks, there was so much electricity there.”

Mrs. Behson then asked, “Do you think Dave is gay?”

“I don’t think so,” I replied, “he’s dated a lot of girls, and he seems to like girls. I’ve never seen him try to get close with any of the openly gay guys we know.”

“Then how about you?” she asked.

I waited a moment before I spoke. “I’m not sure. Yes, there is something between us, but I don’t know if I am attracted to him as a gay boy, or rather as a girl in a boy’s body.”

“That’s pretty heavy stuff for you to carry around. You might want to get counseling. I am not qualified to advise you,” she said. But I do have something for you. Do you still have the panties and bra that I got for you?” I nodded my head.

“I’ve collected some of the makeup we used, along with some other stuff you might find useful and I put it in a bag.” She handed me the bag. “Just in case you want to be a girl again. I also put in a list of clothing you may want to get along with the sizes that should fit you. However, remember that women’s and girl’s clothing sizes are not exact. You may find a dress which fits you, but another dress, the same size, even from the same manufacturer, may not.”

“Now about your hair. You need to brush it, a lot, and often. The old saying is ‘a hundred strokes every day.’ Now you need to find a feminine style you can use. I think that your hair is just the right size for a french twist. If you’d like, I can show you how to do it.”

“That would be great,” I said.

“Okay,” she said, and picked up a hair brush. “We’ll start by brushing it.” She kept up a running commentary describing what she was doing it. “Then gather it into a pony tail, higher up than you usually do. First hold the pony tail straight back and twist it one or two times. Keep the twist in and lift the end of your pony tail above you head and keep twisting it until is is all twisted. Open the parts of the twist that are on the back of your head and insert the end. You then use something to keep it in place. I have some hair pins here, but a french twist fork does it even better.".

With that she was done. “Looks pretty good, doesn’t it?” I had to agree that it did. “You may want to practice before going out with it.”

* * *

At last, it was the final night, and Dave and I returned to our dorm. Dave and a few of our classmates went down to the common room to talk. I did not join them. Rather I stood in front of the mirror on the closet door and put my hair up in a french twist. I then applied a bit of mascara and coated my lips with red lipstick. I went to my dresser and took out my bra and panties, which I put on. I then covered it up with my robe and waited for Dave to return. He opened the door 15 minutes later. When he closed the door, I stood up and walked over to him, opening my robe as I did.

“Oh boy!” he exclaimed, when he saw what I was wearing and the makeup. I didn’t wait. I put my arms around his neck and pulled his face to mine, and I kissed him, with a deep, penetrating kiss that I wanted to last forever. He returned the kiss.

“Wow!” he said as we separated a few inches. “I thought that you made a rule that said no more kissing.”

“I did,” I said, ‘but you broke it.

“Huh?”

“When you kissed me at practice and performance of the play.”

“But that doesn’t count,” he said.

“So those kisses meant nothing to you?” I said trying, unsuccessfully, to look hurt,

He evaded the question. “Yeah, well if I broke the rule, so did you. You seemed to like our kisses,” he said.

“I admit I did,” I said.

“So what are we going to do?” he asked.

“Kiss me again,” I said as I pulled his face to mine. One kiss turned to many, and I was thrilled by each one.

When we came up for air, I said, “We need to talk while we can still think sensibly.”

“About what?” he asked.

“About us,” I said.

We sat down next to each other on my bed.

“You told me that you’re not gay, but you are kissing someone that you know is a boy. Moreover . . .” I pointed to his crotch. It was obvious that he had an erection.

“Yes, but you don’t look much like a boy right now, except for that.” and he pointed to the bulge in my panties.

“Okay, we can admit that we turn each other on. You say you’re straight, but what am I? Am I gay, or am I a girl inside a boy’s body?

“We know how we feel about each other, so why does it matter if you’re gay or a girl in a boy’s body?”

“Because I really like you.”

“And I you,” he said.

I pushed him back onto the bed and began to kiss him furiously, all over. He was enjoying it immensely. I then did the obvious and earned my sissy badge.

Chapter 2 - Consequences.

One Saturday after school started, I put my hair in a french twist and came down to breakfast. “We need to talk,” I announced.

“About what?” demanded my father. He provided an unfeeling answer to his own question. “About the silly thing you’ve done to your hair?” He snorted and returned to reading the paper.

“What is it dear?” my mother said more sympathetically. “Remember, you can always talk to us.”

Except for issues you don’t want to address, I thought.

“I might be gay, or I might be a girl in a boy’s body,” I said.

“Rubbish!” exclaimed my father with a total lack of understanding. “Is that what the silly business with your hair is about? I can resolve all of your questions by taking you to the barber shop and getting you a buzz cut.”

“I’ve researched it on the internet, and I think that I should see a psychologist,” I stated.

“Oh, the internet, source for all truth,” my father said sarcastically.

“I can see we’re going nowhere with this,” I finally said.

“Give it time,” my mother said soothingly. “It will all pass.”

It was obvious that my parents were not going to want me talk to a psychologist, let alone pay for one. I certainly didn’t have the cash to do it myself.

I went upstairs and took my hair out of the french twist, and put it in a regular pony tail. It seemed that my hair wasn’t happy with this because it retained some wave and curl from the french twist. I then hopped on my bike and rode over to Dave’s house.

Dave’s mother answered the door. “It’s Julie . . ., I mean Steve,” she said with a snicker.

Dave was sprawled on the couch staring at some stupid program on the television. I sat down next to him. “I need to talk with you,” I said in a quiet voice.

“Go ahead,” he said, his eyes still on the television.

“In private,” I said.

“Okay, if you must,” he said, standing up. “Steve and I are going out for a ride.”

“Be home for lunch,” his mother said.

Dave and I rode to the local park, and sat down next to each other on a picnic table. “Okay, what’s the big deal?” he asked.

I related what had happened that morning at my house. I also told him what Mrs. Benson had said about a psychologist. “Yeah, you should see a shrink,” he said. “However, you might be stuck with seeing the school psychologist.”

“I’m not wild about that,” I said.

“Yeah, but it may be the only game in town,” he replied, “So are you a girl or a boy?” he added.

I didn’t answer him.

We sat in solitude until Sue and Cindy, two girls from our class, came over.

“Whatcha guys doing?” Sue said as she sat down at the picnic table.

“Enjoying the clear, crisp fall weather,” Dave said. It was overcast and humid.

“Weird,” said Cindy.

“Hey Steve, is it true what we heard about you playing a girl in a play?” asked Sue.

“It was Juliet, as in Romeo and Juliet. Shakespeare,” I said.

“Did you wear a dress, and all that stuff like a bra and panties?”

“I wore a costume that was ordered by the producer,” I responded.

“Do you still have it?” asked Cindy.

“Why would I want to do that?” I said. “It was rented and really expensive and if it wasn’t returned, somebody, like me, would have to pay for it.

“‘Cause I’d like to see you in a dress. You’ve got a cute face and might make a cute girl,” she commented.

“But I’m not a girl, I’m a boy,” I said in frustration.

“Question answered,” Dave said.

“What,” said Cindy, not understanding that.

“It was about something we were talking about before you showed up,” I said, “and it doesn’t answer the question.”

“You guys want to go with us to a movie and pizza tonight?” asked Sue. It appears that Dave and I had just been asked out on a date by two girls.

“Maybe, if you don’t mind riding the green limousine,” said Dave.

“Yuck,” said Sue.

“No car?” asked Cindy.

“No car,” answered Dave.

“Well, see you around.” said Sue, and they left.

“Would you like to get into Cindy’s panties?” Dave asked, with a lecherous smile.

“Not really, I’d rather wear them.”

“You’re hopeless,” Dave commented.

“Remember the summer? I really could use a kiss right now,” I said.

“No way, too open, too many people, Dave said.

* * *

That Monday I went to the school office. “I’d like to see the psychologist,” I said to the secretary.

“About what?” she asked. So much for patient confidentiality.

“Personal problems.”

“Like what?” This woman just won’t give up.

“I’d rather tell that to the psychologist.”

“Okay, be that way,” she said. “How about Thursday, third period?”

“I have a class at that time.”

“It’s Thursday, third period, or three weeks from now.”

“I’ll take it. Do I need a pass or something?

“Not if you clear it with your teacher first. What’s your name, so I can pencil it in.”

I studied gender dysphoria and homosexuality on the internet the next few evenings. On Thursday, third period, I presented myself at the school psychologist’s office, after having cleared my absence with my teacher. The psychologist introduced herself as Dr. Brown, and asked me to sit. “What is the nature of your problem, Steve? I can call you Steve, can’t I?

“Sure. I’m worried that I may be a homosexual or a girl in a boy’s body.” I said.

“And why does that bother you? There’s nothing wrong with being homosexual or transgendered; we even have a student LGBT support group here at school.”

“I’d like to know, so I can figure out what to do.”

“What makes you think that you might be either?” she asked.

I related the events in my life, including the affair at the camp with Dave.

“And is Dave still your friend?”

“Yeah, at least I think so,” I replied.

“Did you talk to him about this?

“Yeah.”

“And what did he say?”

“He told me to talk with you,” I answered.

“Have you talked about this with your parents?” I told her that I had.

“And what did they say?”

“They said I was being silly and it all would pass in a few years. They are unwilling to pay for a psychologist.”

“There is a group know as the Easton Clinic here in town that specializes in your situation. I’d like you to take a test first. Do you have an open study hall period today?”

I told her that I did, and she gave me a large envelope. “This is the test. I want you to be as truthful as you can be. Accuracy, and not speed, counts. If you finish it during your study hall, bring it back to the school secretary, who’ll get it to me and I’ll use it to make a preliminary evaluation. If you can’t finish it during study hall, take it home tonight and drop it off in the morning. I can fit you in next Tuesday, third period, and we can discuss the results. After we talk next Tuesday, I can write a note to your parents recommending that you be allowed to visit the Easton Clinic”

“Yeah, maybe they’d pay attention to you,” I said.

* * *

I kept my appointment the next Tuesday. “You appear to have a lot of signs indicating gender dysphoria, but you appear to have some homosexual tendencies, so I’m not going to say its one or the other. I’ll leave that up to the Easton Clinic.”

She handed me an envelope. “Give this note to your parents. Hopefully they will relent and allow you to see someone. Get a hold of me if there are any problems.” I thanked her and headed to my next class.

* * *

On Monday, Dave and I rode our bicycles to his house from school. We went up to his room. Neither of his parents were home. Only his sister was.

“I want to thank you for your advice,” I said, “ I saw Dr. Brown at school, and she gave me a test. She also wrote a note to my parents advising that I go to the Easton Clinic. I couldn’t have done it without you.”

Dave was sitting on his bed. “Come here,” he said. I sat next to him on the bed. He put his arm around my shoulders, and pulled me toward him. Our lips touched and I put my arms around his neck and returned the kiss, again and again. His hands roamed my body. I could see that he was getting aroused.

“Remember what happened that last night at camp?” he asked. I nodded my head. “Could you do it again?” he asked. “With pleasure,” I answered.

I wondered if he wanted to reciprocate, but he hadn’t even hinted that he wanted to or was even willing to do it. Later, I thought.

Afterwards Dave and I started playing a game on his computer. It was lucky we did, because a few minutes later his sister knocked on the door and came in. “Whatcha guys doing?” she asked.

“It should be obvious to anyone, even an idiot like you, that we are playing a computer game,” Dave said.

His sister ignored the insult and turned to me. “I hear that you were a girl up at camp. Is that true?”

Dave snorted.

“I played the part of Juliet in a play, if that’s what you mean,” I answered.

“Do you like wearing dresses?” she asked with a smirk. Dave laughed.

“It was only one dress and only during the play,” I explained. I didn’t think that she needed to know that I would love to wear dresses all the time.

“I only wondered because I remember that you liked to be the mommy when you, Dave and I played house as little kids.” I made no response.

* * *

That evening I gave Dr. Brown’s note to my parents. “Who is this Dr. Brown?” my mother asked.

“The school psychologist,” I answered.

“You didn’t talk to us about this first,” my mother said accusingly.

“I did, when I came to breakfast with my hair in a french twist. You made it pretty clear that I would have to take the initiative,” I responded.

“So you want us to go with you to this Easton Clinic?”

“Yeah, I do,” I said. “I called them and they can see us for an introductory appointment on Saturday.”

“Okay, we’ll go, if for no other reason to get those silly ideas out of your head,” My father said.

The session on Saturday was all about filling out forms and meeting some of the staff. The first real appointment would be the next Saturday morning.

* * *

It was during my second session at the clinic the counselor asked my how often I cross dressed. “My parents won’t allow me to,” I answered. My parents were with me. My father smiled and my mother looked uncomfortable.

“Is that true?” the counselor asked my parents.

“You betcha,” my father said proudly. “No perverts in my house. It was bad enough that he traipsed around the stage in a dress for that play.” And I thought that he was proud of my performance. Well, that was then, an this is now. My mother said nothing.

“What play was that?” the counselor asked.

“Romeo and Juliet.” I said. “I played Juliet. It was at the Laughton Academic Achievement Camp, which is all boys.

“She did a marvelous job,” my mother said softly, “I was so proud.

“It’s ‘he’, not ‘she’ Katherine,” my father loudly interjected, “don’t encourage him.”

I frowned. The counselor had a tired look on her face.

The counselor then turned to me. “Do you have a girl’s name,? She asked.

“He’s a boy. Why would he have a girl’s name?” my father interrupted.

The counselor bristled, as if she had enough of my father. “I asked Steve, not you,” she said, with ice in her voice, and she turned her head to look at me for my answer.

“Not really.” I answered. “There just doesn’t seem to be any opportunity to use one. However, I have thought about it, and if I use a girl’s name, I’d like to use ‘Stephanie’ or ‘Steph’ for short.”

The counselor wrote the names on her notes. I saw that she drew a little heart for the dot above the I. She caught me looking as we smiled at each other. For the first time, I felt connected with the counselor.

The counselor straightened up the papers on her desk. “I think that we did all we could this time,” she announced. I’ll see you next Saturday, same time. Oh, by the way, I’d like you to let Stephanie to come dressed as a girl.”

We rode home in silence. I could see that my father was fuming. My mother just had a concerned look on her face.

The next day was Sunday. My father was out at a golf game. My mother came into my room, and woke me up. “I think we need to go shopping,” she said.

I knew exactly what she meant. “I have a list. Let me get it,” I said. “It’s not going to freak you out if I wear a bra and panties, will it? I asked.

“We’ll let your father do that for both of us. By the way, how did you get a bra and some panties?” she asked.

“Mrs. Benson gave them to me, along with the list. I want to fix my hair and put on some makeup.”

“Makeup?” she asked.

“Again, from Mrs. Benson.”

“What are you going to do about your hair?” she asked.

“A french twist,” I replied.

“Like you did before? I’ve got to see you do it,” she said.

“May I use your vanity?” I asked.

“Of course,” she said and we walked into my parent’s bedroom. I put my hair up in the french twist and applied some subtle makeup. Mother was pleased with both. “That french twist is so simple, but it looks so feminine,” she said.

I walked back to my room to put on my bra and panties, and to try to find some clothes which didn’t shout “Boy.” Not a lot of luck here. However, my mother solved the problem for me, when she came into my room with an armful of clothes. We settled on a maxi skirt and peasant blouse. I chose the maxi for two reasons: first, I hadn’t shaved my legs and second, I could wear my own shoes without calling attention to them.

She handed me a purse, and instructed me to put my cell phone, driver’s license, some mascara, a lipstick, a comb and my list in it. While on the road, I read the list to my mother. We then hit the mall.

The feminine pleasure of shopping for clothes was tempered with the solemn realization that I might not be able to ever wear them, given my father’s attitude. We pared down the list until I had enough for two complete outfits, a skirt and blouse set and a pretty print dress, along with the necessary underthings. Five pairs of inexpensive pantyhose and a pair of simple black shoes with a one inch heel completed the purchases.

We decided to forgo dressing that evening. I would wear my new clothes for the next session with Ms. Branch on Saturday.

* * *

I woke early on Saturday morning and grabbed a razor and retired to the shower to get rid of some hair. My mother had obviously anticipated this, because there was a container of hair remover on the sink. I followed the instructions on the label and used it all over my body below my head. When all of my body hair, not that there was much of it, went down the drain, I ran my hands over my smooth skin. I then took the razor and gave myself a very close shave on my face.

I wrapped the towel around me and headed back to my bedroom, where I put on panties and a padded A cup bra. It wasn’t much, but it did give the hint of breasts. I sat down and rolled the panty hose into a rose, like I had seen my mother do, and pulled them as high as I could. I then dried my hair and put it up in the now familiar french twist. I looked at the skirt and the dress. Both had a gathered waist, which allowed them to flare out somewhat, which was a good idea since I had no hips. I chose the dress, and put it on and slipped on my shoes.

I couldn’t very well go into my parents’ room to use my mother’s vanity, so I returned to the bathroom to apply my makeup. Day time makeup, I thought. Less is more. For this it meant some mascara, a hint of eye shadow, a little blush, and a subdued pink lipstick.

I looked at my hands. They needed help. I had been letting my nails grow, and they were about a 16th of an inch longer than my finger tips. I took a nail file and gave them somewhat of a shape. I used a clear polish. Less to have to remove after the counseling session. I went back into my bedroom and looked at myself in the full length mirror on the closet door. “Not bad,” I said to myself, “Not bad at all.”

Just then there was a knock at the door. “May I come in?” my mother said. “Do you need any help?”

“Come in,” I replied.

She came into the room and stood still and silent for a moment. “Obviously not,” she said in answer to her last question. “Come over by the window so I can get a good look at you.” As I walked to the window I gave her a twirl. “You really look good,” she said softly. “I can barely see the boy under all of this.” I smiled.

Why don’t you come downstairs for some breakfast,” she said. “Your father is there, and I think we should get it over sooner rather than later,” she added.

We entered the kitchen, expecting an explosion which did not occur. “Absolutely disgusting,” he muttered. “I never thought I’d see the day,” he added, and he returned to reading the paper.

Other than a few outbursts from my father, nothing was said until we arrived at the Easton Clinic. Once there, my mother went to the receptionist and told her that the Spicer family was there for their appointment with Ms. Branch. Smoothing my skirt under me, I sat primly on the edge of my chair, knees together, and my back straight. My father took a chair across the room, and pretended great interest in a magazine. I guess he doesn’t want to be associated with me. My mother sat next to me and squeezed my hand in support.

I stood up when Ms. Branch entered the room. She stood still; just looking at me. I smiled at her. “I can hardly believe it’s you,” she said. “Come on in, and let’s get started. My mother, and I followed her to her office with my father trailing behind. When we sat down, she said, “You really look pretty. I see a lot of Stephanie and not a lot of Steve here.”

My father just grunted.

“She did it all herself,” my mother said proudly. My father grunted again.

Ms. Branch addressed my father. “You have a beautiful daughter here. Even you have to see it. The sooner you accept that fact, the better things will be.”

“I don’t know why I have to accept it,” he said. “What will our relatives, friends and neighbors say when they see him prancing around in a dress?”

“What they say is their business, not yours,” Ms. Branch said. “I think that you are less concerned about your daughter than what anyone else thinks,” she continued, “she deserves her family’s support.”

“He’s a he, not a she, and he’s not my daughter,” my father said. “Can’t we at least get that straight?”

“Look at her,” Ms. Branch said to my father. “Don’t you see a pretty girl, a daughter and not a son?”

“What I see is a pervert prancing around in a dress,” he said with obvious disgust.

My mother saw that I was on the edge of tears. “Don’t cry, Honey, you’ll run your mascara.” Leave it to my mother to shift the tone of the conversation. Ms. Branch smiled at the comment.

“I consulted with a doctor here, and he thinks that you should have some blood tests before we go much farther.” she said as she handed me the order. “Try to have it done before our next appointment.”

“Now I want to talk to you about school.” she said. “Any problems there?” I shook my head. You’re now a junior, right?” I nodded my head. “It may be wise to not institute any changes until you graduate, no hormones, no dressing as a girl at school.”

“Thank God for little things,” my father spouted out. Ms Branch gave him a dirty look.

“You told me that you have a close friend. Dave, is it?” she said.

“Yeah,” I answered, “he and I have been friends since preschool. He went to Laughton Academic Achievement Camp with me this past summer. We were roommates. He was Romeo in the play where I was Juliet. It’s an all boys camp, which is why I was Juliet.”

“How do you feel about him?”

“He’s my closest friend.”

“From what I recall of the play, Romeo and Juliet kiss. Did you and Dave kiss in the play?”

“You should have seen them,” my mother interjected, “it was no little peck.”

“Oh?” Ms. Branch said, raising her eyebrows. “And how did that make you feel?”

“It was okay.” I responded.

“Just okay, nothing more?” Ms. Branch asked.

I was reluctant to admit to more, but I finally said, “It was more.”

“Are you romantically involved with him?” she asked.

It took me a moment to decide if I should answer this question truthfully. Truth won out in the end.

“Yes,” I said softly.

“As Steve or as Stephanie” she then asked.

My mother was paying rapt attention to the questions and answers. I was feeling very uncomfortable at this time. “I’m not sure, but I think as Stephanie.” I finally said.

“I can see that you are uncomfortable. Would you like to defer this discussion to a later session?

“Yes,” I said, with a great feeling of relief.

“A while ago you said that you had not worn girls clothes outside of the house. Is that correct?”

“Today is the first time. In fact, I don’t even wear them at home.”

“Darn tooting.” my father interjected.

“I see,” Ms. Branch said. “Would you like to wear girl’s clothes at home and occasionally outside your house?”

“Yes, I would.”

“Not while I’m in charge!” my father exclaimed.

Ms. Branch addressed my father. “Mr. Spicer, I wish you would keep your comments to yourself.”

Ms. Branch again turned to me. “Would you like to wear girls’ clothes when you are with Dave?

“Yes,” I replied, but I’m not sure whether his family would approve.”

“Why don’t you talk with him about it and we can discuss it at a later session?”

With that Ms. Branch closed her folder and stood up. “That’s about it for today. We’ll see each other next week.

When we got in the car, my father said, “I never thought that I’d have a damn fairy living under my roof.’

“Joe, knock it off,” my mother commanded.

How Romeo and Juliet Changed My Life - Part II (Conclusion)

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Final Chapter

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Estrogen / Hormones

Other Keywords: 

  • Hormone imbalance
  • Butterfly effect

Permission: 

  • Posted by author(s)

How Romeo and Juliet Changed My Life
By Pentatonic

Part II - Conclusion

Author’s Note: This is a continuation of How Romeo and Juliet Changed My life, Part I, where Steve and Dave attend an all boy’s summer camp and Steve ends up playing the part of Juliet in Romeo and Juliet. Maybe Steve would rather be Stephanie, and starts counseling. All is not happy at home, however.

Chapter 3 - Deeper and Deeper.

When we were home after the third session with Ms. Branch, I undid my French twist, removed my makeup and changed back into my boy clothes. I then rode my bicycle over to Dave’s house. As usual, he was sprawled in front of the television. “Want to go for a ride?” I asked.

“Yeah, okay,” he said and he stood up. “Ma, Steve and I are going out for a bike ride,” he announced.

“Okay,” his mother replied. “Have a good time.”

“Where do you want to go?” he asked once we were outside.

“Somewhere private where we can talk,” I responded. We ended up at the same park and same picnic bench as before.

“Okay, what’s up?” he said.

“You know that I’ve been going to counseling. Well, something came up today.”

“What?”

“Us.”

“What about us?” he said warily.

“The counselor brought up me dressing as a girl, and asked me if that would bother you. So I’m asking if it would.”

“Heck, I’ve seen you dressed as a girl in the play. I even kissed you when you were dressed as a girl.”

“And other times,” I reminded him with a smile

“Okay, I wouldn’t mind, but it becomes a question of when and where. Like, for example, school’s not a good idea.”

“I agree. I just want to know if the concept is okay.”

“It is. Do you want to do it at your house?”

“Unfortunately, that may not be an option.” I explained my father’s attitude.

“I don’t know about my house, either,” he said. “My parents probably wouldn’t like it, even if my sister thought it was a cool idea.”

“Your sister?” I asked. “Does she know about us?”

“No, but she thinks that you are awfully girly.”

“There is another problem,” I said, “it takes a while for me to get into girl mode, and it is best done when I’m at home.”

“How does your mom feel about you dressing up?” he asked.

“I think that she’s cool about it,” I said, “after all, she took me shopping to get some girl clothes.”

“Okay, then, how about at your house when your dad isn’t home?”

“That may be it,” I replied.

“Anything else?” he asked.

“Yeah. We were pretty heavily into it at camp. Do you still feel the same way?”

He didn’t respond immediately. “Yeah, I think I do,” he finally said.

“Prove it,” I challenged him. “Give me a kiss.”

“Right here, out in the open? Someone is likely to see us, and since you don’t look like a girl right now, they may get the wrong impression.”

I stood up. “Okay, then behind the field house. No one will see us there.” I grabbed his hand and pulled him to his feet.

We walked behind the field house, checking right and left to see if anyone could see us. No one could.

I moved close to him and put my arms around his neck and he put his arms around my back. We pulled each other closer, and our lip met. Our tongues explored each other’s mouth. It made me feel wonderful. We broke off for a moment to see if the coast was still clear, and went back to our kiss. He seemed to enjoy it as much as I did, because I could feel his erection pressing against my belly.

We finally came up for air. “That was wonderful,” I exclaimed. “I’ve missed our kisses.”

“So have I,” he admitted.

We spent the rest of the afternoon just goofing off, and I returned home feeling better than I had for quite a while.

On Monday morning before breakfast my mother told me that the blood tests were fasting tests, and that we were going to the lab before school. At the lab I was led into a small room to wait for the vampire; oops, I mean the phlebotomist. She walked in the room and looked at the blood test orders, and I could see that she was counting the number of gallons, oops, I mean vials, she would need. I wondered if she drew any conclusions from the nature of the tests which were ordered.

After the blood draws, my mother mentioned that the Easton Clinic had called her and said that they wanted me to have a complete physical, and that she had called Doctor McNally and she could do it this morning. “I called the school and told them that you had a doctor’s appointment and would not be at school until after lunch,” she said.

“Dr. McNally isn’t our usual Doctor,” I commented.

“No, she’s my gynecologist,” my mother said.

“But gynecologists women’s doctors,” I said in the way of objection.

“And you are . . .” she said, leaving the sentence incomplete.

When we got to the Doctor’s office, the receptionist handed me a clipboard with a medical history questionnaire. “Have a seat, miss, and fill it out, and then give it back to me.” I let the word “miss” slide.

The questionnaire had the usual questions, birth date, height, weight, allergies and previous medical history, but, interestingly, no question of whether I was male or female. Maybe they thought that they didn’t need to.

I chuckled at the questions that asked whether I was pregnant, the date of the onset of my last menstrual period, and whether I had any vaginal discharges.

A time after I gave the receptionist the completed questionnaire, she said that the Doctor could see me now, and my mother and I went to Dr. McNally’s examination room. “Hello, Mrs. Spicer,” she said, “and this is your daught . . .” She stopped mid-sentence. When she recovered her composure she said, “We don’t usually treat boys.”

“He’s a patient at the Easton Clinic,” my mother said, “so I thought it would be okay.”

“Oh, the Easton Clinic,” Dr. McNally said, with a look of understanding on her face. She weighed me, measured my height, took my blood pressure and listened to my heart. In a few minutes I was on the examination table wearing nothing except one of those silly disposable patient gowns. There were two arms coming from the bottom of the table with places for my feet.

Then the “fun” began. It was embarrassing, especially with my mother present. “Have you been intimate with anyone?” the Doctor asked.

“I’ve kissed a boy,” I responded.

“How about anal intercourse?”

“No way!” I stated with vehemence.

“How many different boys have you kissed?”

“Only one.”

“Who?”

“My friend, Dave.”

“Anything more than kissing?” I must have turned redder than a stop sign, and I just nodded. By this time my mother was looking shocked.

The Doctor then lifted up the paper gown, exposing my genitals. While looking at them, she asked, “Do you get erections?” I said that I did, but I didn’t get that big.

“When you kissed Dave, did you get aroused?” Again I said that I did.

She then took out a ruler and measured my penis! Talk about embarrassment. If that wasn’t bad enough, she started squeezing my ball sac. “Well, the good news is that your testes have descended.” I had no idea why this was good news.

The Doctor then lifted the paper gown almost all the way up, and looked at my chest. “Any pain or soreness?” she asked.

“No.”

“Your nipples are larger than normal,” she observed, and began prodding and poking around my nipples. “There appears to be more tissue here than I would expect. Have you been taking hormones?”

“No,” I replied.

“I think that we need some blood tests,” the Doctor said.

“We just had some done that the Easton Clinic wanted,” my mother said, “I have the receipt and it lists the tests.” My mother handed it to Dr. McNally.

“These ought to do for a start,” Dr. McNally said after she reviewed the list, “would you ask the Easton Clinic to send the results to me?” My mother said she would.

“Do you ever dress up like a girl?” Dr. McNally asked.

“I have, but my dad doesn’t want me to, so only rarely” I answered.

“How do you feel about his dressing up?” the Doctor asked my mother.

“I don’t mind. Sometimes it’s nice to have a daughter,” my Mother answered.

The Doctor turned to me, and said, “I don’t imagine you want to be called Steve when you’re dressed?”

“Stephanie,” I answered, “or Steph for short.”

“Okay,” the Doctor said, “that does it for today. “I’ll write up my notes and send them to the Easton Clinic. I want you to make an appointment for a followup visit in two weeks. If your nipples get sore, give me a call.”

“Am I growing tits?” I asked.

“Here we refer to them as breasts, not tits,” she said reprovingly. “But to answer your question, it is possible. I won’t know for sure until all the results are in and we see what develops.”

Once back in the car on the way to school, my mother turned to me and said, “you never told me about you and Dave.”

“I didn’t think it was important,” I responded.

“You’re my child. Everything you do is important to me.”

“Maybe, but Dad would blow a gasket if he knew.”

“That may be so, but I have one question for you, and I want a truthful answer. Did you ever have Dave’s penis in your mouth?”

After a pause, I said, “Yes.”

“How about the other way around?” she asked. I didn’t think that it was a good time to remind her that she said that she had only one question and that this was question number two.

“No,” I replied.

* * *

My mother and I arrived at the Easton Clinic on Saturday to hear about the results of the blood test and Dr. McNally’s findings. My father elected to not attend, but rather to play golf with his friends. It was just as well with me. I dressed en femme. When we went into Ms. Branch’s office there was a man already sitting there wearing a white lab coat. “I’ve asked Dr. Liss to sit in on this meeting, if you don’t mind. I have consulted with him all along, and I think that he is more qualified to answer your questions than I am,” Ms. Branch explained.

“You must be Stephanie,” Dr. Liss said, “I imagine you are anxious to hear the results of the tests. It appears that even though you are 16, the onset of puberty has been delayed. While your testicles have descended, your penis is small. Your hormone levels show that your testosterone levels are low but your estrogen level is high. We could wait and see if you experience a growth spurt, which most likely means that you will develop like any man. If you don’t experience a growth spurt, we could look for something else, and maybe try some hormones which will speed things along.”

“However, that might not compatible with one of your stated options when you first came to us, that is to recognize that you are a girl in a boy’s body. It would be compatible if you decide that you are a homosexual man. Ms. Branch and I have discussed hormone therapy, and don’t think it is recommended in your case, at least not at this time. Let me explain. If you are a girl in a boy’s body, and you want to be a transsexual, we could give you hormone replacement therapy. That would decide the issue against remaining a male. However, hormone therapy would cause you to develop female traits, such as breast development. Since you want to go on to college, hormone therapy would make your high school career more difficult, because you would look more and more like a girl as time went on. This itself could cause you problems.”

“Therefore, I would recommend that no medical action be taken at this time, and wait until you are ready to graduate from high school, at which time you would have to decide if you are a homosexual or want to be a transsexual. You should keep coming in, but less often, and we would closely monitor you. I note that you have seen Dr. McNally, and she reports that it is possible that you are developing breasts. Continue to see Dr. McNally and have her report any significant developments.” With that, he thanked us for coming in and left.

“Okay, Ms. Branch, what does this all mean?” I asked.

“Simply put, no hormones, and we wait and see what happens over the next year or so,” she said.

“I’m not sure I like that,” I said.

“There’s not much I can do about that,” she said.

On the way home, my mother turned to me and said, “you might not like what they said, but I think that they may be right. Waiting to see what happens may be the safest thing to do.”

I said nothing.

* * *
Chapter 4 - The Halloween Dance.

After my fourth appointment at the Easton Clinic, Dave stopped by. My mother gave him a “what are you doing to my poor daughter?” look, which Dave and I thankfully ignored.

“I got a new game for the computer. Want to try it?” I asked.

“Sure,” he answered, and we headed up to my room.

“We have to be careful, my Mom thinks we are up to something,” I said.

“We are, so what?” he answered.

“I have to live here, so we’ve got to be cool,” I said.

“Okay, where’s this game?”

“There isn’t, it was just an excuse to get you up here so we could talk,” I said.

I explained what happened at the Easton session and poured out my frustrations. I was ready to cry.

Dave sensed this and said, “That’s heavy stuff. Let’s talk about fun stuff, instead.”

“Like kissing?” I said in a seductive tone.

“No, about Halloween, and then maybe kissing,” he replied.

“Let’s start with kissing,” I said and I put my arms around him, and we kissed. Suddenly I heard footsteps on the stairs. “Mother’s coming up here,” I said with alarm. We quickly disengaged and stared at the computer screen.

There was a knock at the door, and without an invitation to enter, my mother opened the door.

“Do you kids want anything to eat?” she said with feigned inocense,

“No, Mother, we’re all right,” I responded.

After she left the room, I asked, “Okay, what about Halloween?”

“It’s less than two weeks away, on a Friday. The school is having a dance. You want to go?” he asked.

“Is that a date?” I laughed.

“We could go stag,” he said, but we should think about costumes.

“Why? If we’re going stag, you pick out your own costume, and I pick out mine, that is, if I decide to go.”

“You have to go. I was hoping to coordinate our costumes,” he said.

An evil thought ran through my mind. “How about Disney costumes. I could be Peter Pan, and you could be Tinker Bell.”

“Very funny,” he said sarcastically. “I was thinking more or less like Romeo and Juliet.”

“People would assume that we are a couple,” I said. “That wouldn’t do anything good to our reputations. One or both of us would be labeled as gay.”

“Okay, I only suggested that since it would be an opportunity for you to dress as a girl. You seem to want to do that,” he said.

“I do, but we need to keep it so we aren’t connected with each other as a couple.” I suggested that I would wear an evening gown and Dave would go as a pirate.

I told my mother what Dave and I had come up with, and she agreed to help. She picked Dave and me up from school and went to my house where I started my transformation. I borrowed Mom’s maxi and peasant blouse again, put on my own panties, bra, panty hose and shoes. I put my hair in a French twist and added a touch of makeup. My mother handed me a purse and I filled it with my necessaries, after which my mom, Dave and I headed to the thrift store.

I found a long evening dress which fit, more or less, but which my mother assured me she could alter. We found a wig for me, just in case. Dave found some pants and a shirt that he could make into a pirate costume. The crowning part of his search was a wide black belt.

We got home well before my father got home, so I was able to take my hair down, clean off the makeup and get back into my regular school clothes.

* * *

On Thursday, I was uncomfortable all day at school. My chest, and more particularly my nipples hurt. When I got home from school, I mentioned this to my mother.

“Come into the bathroom, where there is good light, and take off your shirt and undershirt,” she instructed.

She looked closely at each nipple, and then touched one of them, They were sensitive, and I told her so. She said, “I think that your undershirt was rubbing against them. Were you wearing one of your usual T-shirts? It’s not a new one, is it?”

“Usual and not new,” I said.

“I have a suggestion,” she said, “put on your bra, and see I that helps. You might want to cover it up with a loose flannel shirt, so your father doesn’t notice that you’re wearing a bra.” I did as she suggested, and found immediate relief. “We’ll have to mention this to Dr. McNally next Monday.”

On Monday, we checked in with Mr. McNally’s receptionist and she handed me one of those paper examining gowns, and told me to go to the examination room, take off all of my clothes and get on the examination table, as had been done before. A short time thereafter Dr. McNally walked in

“Well, how are we?” the Doctor said routinely.

“Okay, I guess,” I replied, “but my nipples have been bothering me.”

“Oh,” she said with more than casual interest, and she lifted the paper gown up to my shoulders. She poked, prodded and rubbed my nipples and my chest near them. “What did you do about it?”

“Mom suggested that I wear a bra,” I answered.

“Did that help?”

“Oh yeah,” I replied.

She looked at her file, and pulled out a photograph of my chest taken the last time I was there. “Only two weeks, and I can see a slight change.”

“Sit up, and let me measure you,” which she did. “No significant difference, but I can feel more breast tissue. We’re going to have to keep an eye on them.”

She told me to lie down and she put my feet in those things which I later found out were called stirrups, leaving my crotch exposed to the breeze. She pulled on my penis and poked and prodded my balls. “Nothing new there,” she said.

“Have you taken any pills that you haven’t already told me about?” she asked.

“No, nothing.”

“I got the results of your blood tests from Easton. Did they explain them to you?” she asked.

“Yeah, they said that puberty was delayed at that my hormones were all messed up,” I replied.

She laughed. “Well, that’s one way of putting it. What did they recommend you do?”

“Essentially nothing until I graduate from high school, and they cut back my counseling sessions.”

“Oh? Did they mention hormone replacement therapy?”

“Yeah, they did, but said they wanted to wait and see what happened all by itself until I graduate.”

She looked through her file. “Ah, we do have the signed releases of information,” she said to no one in particular. “I think that I would like to discuss your case with them. Unless I’m wrong, something has just started to happen, as you say, ‘all by itself’.”

“Does that mean I’m getting tits?” I said brightly.

“I told you we don’t like that word around here, but, as you so crudely put it, it is possible that you are growing tits.”

“Cool,” I said, “Just wait until dad finds out. He’ll flip.”

“What do you mean?” Dr. McNally said.

“He goes nuts every time anyone brings up my wearing of any female clothes,” I responded.

“I see,” she said. “Wait a moment and I’ll give you a ‘to whom it may concern’ letter, saying that it is medically advised that you wear a bra or nylon camisole to protect your nipples. It’ll also request that you be excused from PE or any sports. You can show it to your father and give it to the school.”

I smiled. A minor victory won.

“Does this mean that I’m turning into a girl?”

“As opposed to anything else?”

“Yeah.”

“No, it’s too soon to make that kind of evaluation.”

“Okay, you can go now,” she added. “Wait for the letter, and make an appointment to see me in two weeks.”

After dinner that evening my mother showed my father the letter. “What’s this all about?” he demanded.

“She may be growing breasts,” my mother said, intentionally using the pronoun ‘she’.

My father’s face was turning red with anger. He threw the letter down, jumped up from the table and stalked into the living room. “Quacks!” he shouted.

* * *

On Tuesday afternoon, my mother began the alterations on my evening gown in earnest. The first thing she did was to modify the top part so it hung correctly given my small breasts. She then had me put on my one inch heels, and stand on a stool so she could adjust the hem. She marked up various seams to get the fit just right. We were done and everything was put away by the time Dad got home

On Wednesday my mother gave me a bag. “A present for you,” she said.

I opened it anxiously, and pulled out a full length slip. “Thank you, Mom,” I gushed.

“I thought the evening gown needed a slip to hang correctly,” she said. “But there’s more in the bag.”

Indeed there was: a pair of long gloves and some costume jewelry. I went over and gave her a big hug. “Put on your bra, slip and dress and stand on the stool. I want to make sure of the alterations,” she said. I did, and the alterations turned out to be perfect.

My mother and I came up with a plan for Friday. We would have an early supper, right after dad came home. Immediately thereafter I would go upstairs, do my hair, nails and makeup, and mom would come up and help me with the rest. We figured out that we could finish getting me ready by 7:15, after which my mother would distract my dad and I would slip out the back door. Mom would have one of her coats ready for me by the back door, along with my purse. After I was out of the house, hopefully undetected, I would get in the car and we would run over to pick up Dave. The goal was to get to the dance at 7:30.

On Friday, it worked like clockwork to a point. At 7:20 we were at Dave’s house. I went to the door and rang the doorbell. Dave’s mom answered the door. “Trick or treat,” I said.

For a moment his mother stood there slack jawed. When she recovered she opened the door all the way and said, “Oh my God! Bob, come here. You’ve got to see this and I need pictures.”

Dave’s dad appeared in the room. “Juliet revisited,” he said with a smile.

Tiffany heard the commotion and came to see what was going on. “I knew it! I knew it!” she crowed. “He does like to wear dresses!”

Dave came into the living room as a reasonable imitation of a pirate, his pants and shirt torn, a big black belt, a black eye patch, a bandanna on his head and a pair of black boots. “Arrrg,” he said in his best imitation of a pirate. “Shiver me timbers, it’s a fair maiden.” The schools zero tolerance meant no toy sword or pistols. Pictures were taken, and Dave and I went out to the car.

“I thought you’d never come out,” my mother said.

“Pictures.” I said. She nodded her head in understanding.

“Dave, ask your mother for copies of the pictures.”

“No problem,” he replied.

We were fashionably late, by ten minutes, and we each made our own grand entrance.

I saw that I made an impression. Girls stared at me in wonderment. Boys stared in lust. I thought that I would be immediately recognized, but such was not the case. Maybe it was because I was considered to be a nerd, and therefore invisible and people didn’t remember what I looked like. Maybe it was the hair. Maybe it was the makeup. Finally, maybe it was the dress.

As planned, Dave would seek out his friends, to keep our distance from each other. Neither of us wanted to be part of a ‘couple’ since it may cause problems later. This didn’t bother me.

Cindy and Sue were the first to come up to me. “Steve?” Sue said uncertainly.

“'Tis I,” I said, “but for tonight it’s Stephanie.”

“How did you do it?” Cindy asked.

“Talent, pure talent,” I responded, “and a drama class at the summer camp. I got most of this stuff at the thrift store,” I lied. “My mom helped me a whole lot. She’s good at sewing and stuff.”

“Are you wearing, you know, ah?” Cindy said and paused.

“Underclothes?” I added for clarification.

“Yeah, like a bra and panties?”

I stuck my nose in the air, and sniffed in imitation disgust. “One never asks a lady what she’s wearing, or not wearing, under her dress!”

“No, come on. What are you wearing?”

“It’s a secret,” I said. “Have I asked you what you’re wearing under that skimpy outfit?” Cindy was wearing a brief and revealing witch’s costume. “Not that it isn’t obvious in your case.”

Sue heard this exchange and laughed. This caught Dave’s attention. “Hi guys, what’s going on?”

“Just girl talk,” I replied, “you wouldn’t be interested.”

Cindy, Sue, their dates and I found a table. Cindy and Sue wanted to dance, so I ended up watching their purses. After a while a guy I knew came up and asked me if I wanted to dance. I motioned him to come closer, and I said quietly, “I’m really a boy, and enough people know that, so if we danced it might ruin your reputation.”

“Thanks,” he said, “I couldn’t tell. You do make a beautiful girl, however,”

“I’ll take that as a compliment,” I replied. “It took a lot of work to get this effect.”

After quite a few similar encounters, the guys left me alone for the most part. However, one guy, dressed as a drag queen was much bolder. “Hey, sweety, want to dance?” he asked.

“I’m really a guy.” I told him.

“I know that. So am I. I’m gay,” he said, “but I do want to dance with you.”

“Why don’t you go ahead?” Sue urged. “Try a walk on the wild side.”

“Okay,” I said, and he took my hand and we went to the dance floor. It was a slow dance.

“My name is Al,” he said, “but tonight I’m Alice. How about you?”

“Steve, and tonight Stephanie,” I replied.

As we danced, he held me tighter and tighter until I could feel his erection pushing against my belly. I tried to move away, but he was holding me too tightly. “You’re turning me on,” he said.

“That’s obvious,” I replied.

“You dress as a girl a lot?” he asked.

“No,” I answered truthfully.

“Your hair and makeup is just too perfect for a guy who doesn’t dress a lot.” he said.

“My mother did my hair and makeup.” I lied.

The song was drawing to a close, and Al lowered his face to mine and kissed me. I did not respond. He broke off the embrace, and started to walk me back to the table. Halfway there I said, “I really need to take a leak. Any idea where there’s a washroom I can use, dressed like this.”

“As it is, you’ve asked the right girl for that information,” he said. “Come with me,”

After visiting the restroom he said, “I haven’t seen you at any LGBT meetings. How come?”

“I’m not,” I lied, not willing to admit that I was frightened to do so even if I might be a “G” or a “T.”

When I got back to the table, Sue said, “Did you know that Al is gay?”

“Yes, he told me.”

“You didn’t mind?” she asked.

“No, because he told me which washroom was safe to use,” I responded.

“I didn’t think about that,” she mused.

“You wouldn’t need to. Tonight I do,” I responded.

I didn’t get a chance to dance with Dave, although I wanted to. After the evening wore on, I called my mom and asked her to pick me up. I asked Dave if he wanted to go, but he said he wanted to stay and one of the guys would give him a ride home.

Once in the car my mother told me that Dad was in bed, so when we got home, I undressed, removed my makeup, let down my hair, took care of my clothes and got in bed without any problems. Before I fell asleep I thought about what I had done. I enjoyed being a girl.

Chapter 5 - The Painful Truth.

On the Wednesday after Halloween, my mother got a call from the Easton Clinic. Apparently Dr. McNally had reported the pain in my breasts, and they wanted to see me on Friday afternoon. My mother told me that she would pick me up from school.

“I didn’t tell your father about the recent developments. I didn’t think he needed to know, so it may be best that you don’t say anything about it either,” she said.

She asked me about my breasts, and I told her that the camisole helped.

When we arrived at the Easton Clinic, the receptionist said that both Ms. Branch and Dr. Liss wanted to see me, so it may take a few minutes to get them in the same room. A while later she told us to go to Ms. Branch’s office.

Ms. Branch was sitting at her desk, and Dr. Liss was perched on top of one end of the desk. Mom and I sat down.

Dr. Liss started the conversation. “We heard from Dr. McNally, and we would like to discuss her findings with you. She said that there are signs that your breasts may be growing. If that is so, we may need to change our game plan.”

“First of all, how are you feeling?” Ms. Branch asked.

“Okay, except for the pain in my nipples,” I replied.

“What are you doing about that?” she asked.

“I’m wearing a smooth nylon camisole as she suggested,” I said. “It helps a lot.”

“Would you mind if I looked at them?” Dr. Liss asked.

“Okay,” I said, and I took off my shirt and the camisole. Dr. Liss poked around and felt my nipples.

“I see,” he said, “Dr. McNally may be correct. I can’t tell for sure, since I didn’t previously examine you. You can put your clothes back on.”

After I was dressed, he handed my mother a piece of paper. “This is for additional blood tests. We would like to compare them with the prior tests. We’ll send a copy to Dr. McNally.”

“When is your next appointment with Dr. McNally?” Ms. Branch asked. We told her it was on Monday. “Probably too soon for her to have the lab results,” she added. Dr. Liss nodded his agreement.

“We’d like to put this on a two-week cycle of blood tests and appointments,” Dr. Liss said. “The blood test order is a standing order, so you just have to show up and have the test taken. We’d like to see you in a week, so we have the results of the last blood tests, and then every two weeks thereafter. Have the blood tests done three or four days before your appointments here. I’ll now leave you in the capable hands of Ms. Branch,” he added, and left the room.

We spent the rest of the appointment discussing things in general, and the Halloween dance in particular. “How did you feel getting all dressed up?” she asked.

“I loved it. I only wish I could do it more often,” I answered.

“Any negatives from any of your classmates?” she asked.

“Naw, they mostly though it was really cool. By the way, do you want me to dress for the next appointment?”

“However you wish. If your father comes along it may be best if you dressed in your male clothes.”

* * *

So, I started the every two-week cycle lasting through Christmas, during which time my breasts grew slightly, because, as Dr. McNally said, of the hormone imbalance. Not much growth otherwise, except for my hips and butt, and that only slightly. It seemed to me that I was slowly turning into a girl.

Christmas was mostly like it had been in the past, with one exception. After Christmas dinner, my mother pulled me aside.

“I have another present for you, but you should hide it from your father,” she said and handed me a box. I anxiously opened it. It was the doll that I had always wanted.

By the start of the new year I had pretty much decided that I wanted to become a girl. Dave understood, even though it would change how we acted with each other. I told Ms. Branch at the Easton Clinic, and we reset our aims. When I told Dr. McNally, she smiled and said, “Your body has already made that decision.”

* * *

My breasts continued to grow, but my areolas were growing at a faster rate. I looked at myself in the mirror and liked what I saw. My mother, however, was concerned, and again brought the matter up with Dr. McNally.

“You have told us that Steve’s testosterone level is low, but why?” she asked.

“Did Steve ever have mumps?” Dr. McNally asked in return.

“Yes, when he was six,” my mother answered.

“A mumps orchitis infection can damage the testes. It is called primary hypogonadism or testicular failure. This type of hypogonadism is usually caused by a disease, illness, or external factor that directly affects the testicles’ ability to produce testosterone normally.”

“Another cause of low testosterone is called secondary hypogonadism and usually involves a failure in the communication loop between the hypothalamus and the pituitary gland for one reason or another. To understand this, you have to realize that males do produce estrogen. However, once a man has too much estrogen in his system, a vicious cycle can ensue in which the high estrogen levels leads to a faulty feedback system, tricking the brain and testes into producing even less testosterone. This can lead to even higher levels of estrogen and more severe estrogen dominance, magnifying the high estrogen symptoms.”

“In your case, there are signs that it could be either,” she said to me. “What is clear is that your body is not producing much testosterone but is producing a lot of estrogen.”

So I’m turning into a girl, all by myself, I said to myself.

“What can we do about it?” my mother asked.

“That depends on Steve’s goals. If she wants to transition to being a female, we don’t have to do a lot at this time. On the other hand, if he wants to remain male, we could start Testosterone Replacement Therapy. You don’t have to decide today. Talk it over with your counselor at the Clinic.”

Chapter 6 - The Butterfly Effect.

I remember discussing the “Butterfly Effect” in science class. It posits that small causes can have large effects, like when the flap of a butterfly’s wings in the amazon can affect a tornado in Texas, or something like that. I’m not too sure about it but sometimes it seems to work,

To keep peace in the family, I bound down my breasts except when I slept. One Saturday I had been working it the attic and I was covered with dust, so I decided to take a shower. I left all of my clothes in my room, wrapped a towel around me, and went to the bathroom to shower. When I was finished, I again wrapped the towel around my waist. Wrapping it like a girl would cause too much crud if my father saw me that way. I hadn’t considered what would happen if I wrapped the towel around my waist and my father saw my chest. I soon found out.

I was in the hall going to my bedroom to get dressed when my father unexpectedly came up the stairs. He saw me, his jaw dropped, and he didn’t move a muscle. However, after a moment he seemed to recover. The butterfly had flapped its wings.

“Katherine!” he yelled. “Come here, right now!”

My mother hurried up the stairs. “What is it Joe?”

“Look,” he said, “he has tits! How did that happen? Have you been giving him pills without telling me? Is this something those quacks at the Easton Clinic have done?” he asked, the words tumbling out in rapid succession, not waiting for an answer.

“Joe,” my mother said, “this is something her body is doing all by itself.” My father let the female pronoun go by without an objection. I guess he was too shocked.

“Why don’t the two of you come down to the kitchen and we can talk about it?” she said.

“Can I get dressed first?” I asked, which were the first words out of my mouth since running into my father.

“Yes, dear,” my mother said, and she winked at me. I took that as saying that I should come down en femme.

I went into my room and put on a pair of pink nylon panties, a pink bra and my camisole. “Pantyhose,” I told myself, and put them on. Next, I picked a short skirt and a blouse with ruffles down the front. I put my hair in the now familiar French twist, and fastened it with a new French twist fork which was decorated with sparkly things. As for makeup, I went the whole nine yards. So what if I looked a little tarty, I was going to get yelled at no matter what I wore, so I might as well get yelled at for wearing something I liked. I put on my pumps, and went downstairs.

When I entered the kitchen, my mother smiled and nodded her head, confirming that I had received her silent message. My father, on the other hand, frowned.

“Would someone tell me why my son is growing tits?”

“Breasts, dear. I don’t like the word ‘tits’ used in my house,” my mother said reprovingly.

“Okay, ‘breasts’ then. You still haven’t answered my question.”

“If you had paid attention during the sessions at Easton, and not missed any, you might have an idea. Since you didn’t, let me explain it to you,” she said.

“It better be damn good,” my father grumbled.

My mother ignored my father’s last comment. “Something has happened in her body, and she is not producing enough testosterone to counter the estrogen her body normally makes. This is a hormone imbalance. Something may have happened to her testicles when she had the mumps, or it may have been caused by something else, but the inescapable truth is that she is not producing a lot of testosterone but is producing a lot of estrogen. Dr. McNally can confirm that this has caused her breasts to grow.”

“Can’t they do something, like give him some medicine to turn him into a man?” my father asked.

“Maybe they could,” I finally spoke, “assuming that I wanted to take the medicine. I’m old enough to refuse medications.”

“So, you want to be a girl, and you have the . . .” he paused, “. . . breasts to prove it? How come I never noticed that before?” he asked.

“Because I use an elastic bandage to squeeze them flat,” I responded.

“Oh,” he said.

“I do it to keep you from being upset.” I said to him, “Because I love you.”

“And to answer your next question, yes, it is uncomfortable all the time and painful every once and a while.”

He had seen my breasts. The butterfly had flapped its wings in the amazon. Now I waited for the Texas tornado.

Dad looked pained. It was almost like he had a little storm cloud over his head, shooting bolts of lightning at him.

“Even you have to admit that she’s beautiful, even better looking as a girl than she does as a boy,” my mother said.

My father looked at me. “Yeah, I guess you’re right,” he finally admitted.

“Look,” my mother said, “you’ve had a son for sixteen years. Now I want a daughter for just as long, if not longer.”

Dad just grunted. You could see that he knew that he was losing this battle.

“So you’ll allow me to dress like a girl at home?” I asked. He nodded.

“And even outside of the house when I want to?” I asked. Again, he nodded.

He must have been thinking about how he acted for the last year. He looked like he was ready to cry. I stood up, went over to him and hugged him. It was then that he started to cry,

Okay, it wasn’t a tornado in Texas; it was rain on his cheeks right here.

I kept hugging him. “Dad, I love you,” I said, “I don’t want to lose having a father.”

“And I don’t want to lose you,” he said between sobs.

It was too much for my mother and me. We both started to cry. My mother stood up and came over to us and we had a long family hug until we regained out composure.

Dad hung his head. “I’m sorry for all the mean things I said. Can you forgive me?”

“Forgiving is part of loving,” my mother said, “and we both love you.”

“And I love you.”

A major barrier had been cracked if not broken. Full acceptance would come but it would take time. I knew we were progressing when Dad took us to a fancy restaurant with me fully dressed, en femme.

It’s surprising what the sight of a naked nipple can do, I reflected.

* * *

I invited Dave to come over the next day, which was a Sunday. When he rang the doorbell, my father answered it.

“Hi, Dave, come on in. She’s upstairs in her room.” Dad said.

Dave noted the use of the female pronouns but said nothing until he entered my room and saw me sitting at the computer wearing a skirt and blouse.

“What the heck happened?” he said.

“Dad saw the light. He had a change of heart.”

“How did you do that?”

“I flashed my tits at him.”

“Ooh, I can’t wait to hear about this,” he said, and I told him the whole story.

“So you can be Stephanie whenever you want?” Dave said. I nodded and smiled.

“And you have tits?” Again, I nodded.

“Can I see them?” I nodded my consent, and took off my blouse and bra.

“Can I touch them?” In response I took his hand and placed it on my breast.

It was more stimulating than his kisses. I felt a tingle down to my feet. He fondled my breasts and nipples. I didn’t want it to end, but it did.

“So, do I look kissable?” I coyly asked, or at least as coyly as a girl could right after having a boy fondle her tits.

“Yeah, you do,” he responded.

“So prove it,” I said.

He did.

* * *

Final notes: on the day after graduation from high school, I started on Hormone Replacement Therapy, even though my body had started it on its own. I also became Stephanie all the time, which was great. I have alway loved swimming, but I hadn’t been in the pool since my breasts started growing. Now I had a modest one piece suit, and I could go swimming.

Dave and I are going to go to different colleges, but we promise to remain friends.

It Started On A Rainy Afternoon

Author: 

  • Pentatonic

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

It started on a rainy summer afternoon when I was seven. My sister Emma is two years older than I am and she and I get along. After lunch we had started playing board games, as we often did when we could not play outside. It was about two in the afternoon when my sister stood up and declared, “I’ve had enough of these board games. Let’s do something fun and different.”

It Started On
A Rainy Afternoon


By Pentatonic

It Started On A Rainy Afternoon - Part 1

Author: 

  • Pentatonic

Caution: 

  • CAUTION

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Corsets

Permission: 

  • Posted by author(s)

It Started On A Rainy Afternoon - Part 1
By Pentatonic

It started on a rainy summer afternoon when I was seven. My sister Emma is two years older than I am and she and I get along. After lunch we had started playing board games, as we often did when we could not play outside. It was about two in the afternoon when my sister stood up and declared, “I’ve had enough of these board games. Let’s do something fun and different.”

“Like what?” I asked.

“You know, people say we look alike. Let’s see if that is true. Come on up to my room. I’ve got an idea.” I knew that I had a ‘pretty’ face, and had been mistaken for a girl on numerous occasions.

Mother had left to run some errands shortly after lunch. “Can I trust you two to stay out of trouble? I’ll be back in a few hours,” she declared. We assured her that we would be ‘model’ children, but, as it turned out one of us would be a ‘model’ in a different way.

Even though I am younger than my sister, we are close in size. I wear my hair a bit on the long side, mainly as an expression of independence, or so I thought.

When we were in Emma’s room, she went to her closet and took out a dress. “I’ve grown since this was bought, but it might fit you.” The dress was a maroon taffeta party dress with a full skirt which was gathered at the waist. It had a big bow in the back, a fitted bodice and puffed short sleeves. It positively shimmered.

I was surprised. Not that I would be wearing a dress, because I had snuck into her room in the past and had tried on that very same dress, but because she had suggested it. I gave her a funny expression, indicating that I did not like the idea. In truth I did like the idea, but I just didn’t want her to know it.

“Oh, come on,” she said, “I know that you have tried on this dress before. I just want to see how you look.”

I just made a few incomprehensible noises and wondered how she knew.

“Come on, it won’t hurt you. It’s only a dress,” she said as she held it out in front of me. “Take off your clothes,” she commanded. I shook my head in disapproval.

“It’s not like I haven’t seen you naked before. It was only a few years ago that we stopped taking baths together.” She had me there, and I took off my shirt and shorts. “Take off your underpants,”she added, “I have a pair of panties for you to wear.” With that she opened a drawer in her dresser and handed me a pair of pink panties. Reluctantly I took off my underpants, sat on the bed and pulled on the panties, during which time she appeared to focus on my private parts.

“Can you do something about that bulge?” she asked, pointing to my crotch. I reached into the front of the panties and pushed everything back. “Better,” she said.

She appeared to study me for a minute. “I think that you’ll need to wear a slip,” she commented, and retrieved a slip from her dresser. “I’ll bet you’ll like it,” she said. “Hold up your arms,” she added and she let the slip slide down my body. She was right, I did like the way it felt.

She then picked up the dress and slid it over my head. I loved the feeling. “Turn around and I’ll zip you up.”

“You ready for some shoes?” she suggested. I nodded my head. She handed me some short white socks, with flowers embroidered on them, which I put on. She then handed me a pair of black Mary Janes, which I also put on. She helped me with the strap.

“Walk around, and let me see how it looks,” she said. After I walked around a bit, she said, “give it a twirl.” When I did, the skirt of the dress flared out. The feeling when it came back down was very pleasant.

“Very good,” she said, “now let me do something with your hair.” I sat on a chair, and she brushed and gathered my hair into a feminine style. When she was finished, she suggested, “Stand next to me in front of the mirror, and admire yourself,”

When I did, I was astounded. I actually thought that I looked very pretty; a lot like Emma had looked a few years before. “From the smile on your face, I can see that you like the way you look,” she said.

“Do you like being a girl?” she then asked. I paused before answering.

“Yes,” I said softly.

“In that case, you need some girl lessons, like how to walk, how to stand, how to sit, hand gestures, and very importantly, to remember to sit when you pee,” she said. The last part brought smiles to our faces.

After a few lessons, Emma said, “Mom should be home soon. Let’s show her how you look.”

“I don’t think so; she might not like it and get mad at us,” I responded.

“But she might like it,” replied Emma. “We won’t know if we don’t try it,” she replied. The question became moot, because at that instant we heard Mom open the front door.

“Emma, Jason, I’m home,” Mom announced. “Come down and help me get the car unloaded.”

There was nothing to do but for me to go downstairs as I was. I went first.

“Emma, why are you wearing a dress?” Mother asked. Then she paused when she saw Emma follow me down the stairs. She had a confused expression on her face, and paused for a few moments while she took in what she saw. “I imagine that you have a reasonable explanation for all of this?” she questioned.

“We wanted to see what Jason would look like as a girl,” Emma answered.

“Emma, what’s this ‘we’ business? This has all the earmarks of something you would come up with,” Mom said. “Jason, was any of this your idea?” I could have said ‘No’ and got Emma in trouble, but I didn’t want to do that.

“Emma may have suggested it, but I went along with it,” I confessed.

“I see,” Mom continued, “I leave you two alone for a brief time, and come home to find my son in a dress.” She paused as she looked at me. “However, I must say, you look very pretty,” she added with a smile.

After a minute of silence, Mom asked me, “Do you like wearing a dress?”

“Yes,” I said softly.

“I see,” Mom added, not convincingly. “Do you like being a girl?”

“Yes.”

At that point, Emma suggested that I give Mom a twirl, which I did. Mom had to smile at this. “I see you decided to put on a slip and panties. Very nice.”

“You’re not mad at us, are you?” Emma ventured.

“Not mad,” Mom answered. “Surprised? Yes; mad? No.” Both Emma and I smiled in relief.

* * *

A few weeks later, Mom surprised Emma and me when she came home with a dress, two skirts, two tops, shorts, capri pants, a full slip, a half slip, tights, socks and panties, all for me. “We need to buy you shoes, but you have to be there to make sure they fit,” she explained.

I now had my own wardrobe, which I hid in the back of my closet, in case a friend came over to the house.

A week later, Mom took us shopping. I wore shorts and a top and Emma’s Mary Janes. Of course I wore one of my new panties. In fact, ever since Mom had bought them for me I wore panties pretty much all the time, no matter how I was outwardly dressed. I acquired three pairs of shoes that day, trainers, mocs, and a pair of dressy patent leather pumps. As we were ready to head back home, we passed an earring kiosk. “Would you like to get your ears pierced?” Mom asked. I did.

Because I was dressed as a girl when shopping, Mom noted that she could not call me ‘Jason.’ “Have you picked out a girl’s name?” she asked.

“What would you have named me if I was born a girl?” I asked in return.

“Margaret,” she answered.

“I like Margaret,” I said. That’ll be my girl name. Maybe Peggy, for short.” So thereafter, when dressed, I used Margaret or Peggy, but only when dressed. Sometimes I was called Peggy when dressed in my boy mode, but nothing came of it.

Over the next months, I dressed whenever I could, sometimes with Emma, and sometimes by myself. This did not go unnoticed by Mom. “Jason,” she asked, “I need an answer. Do you think of yourself as a girl in a boy’s body?”

“Sometimes I do, and sometimes I don’t,” I answered.

Mom, Emma and I knew that sooner or later we had to let Dad in on my dressing. While Mom was okay about it, and appeared to approve, the same was not true with Dad. He made it very clear that he didn’t like it at all. After that, I didn’t dress when Dad was around, except that I wore panties nearly all the time except when I was at school.

* * *

When Emma was twelve, her body began to change. One Saturday, when Dad was off playing golf, Mom called to both Emma and me. “Girls,” she said, “I think that it’s time for Emma to get a bra. Peggy, you might as well come along, because buying a first bra is an important time in a mother’s and girl’s life, and unfortunately it is an experience you will never have, so the best you can do is experience it second hand.” Mom did not realize that I had been researching bras and breast forms on the internet, and I expected that I would be buying my own bra in the near future.

As it turned out, I got a training bra the same day as Emma got her first bra. We were in the lingerie store with Emma being fitted for her bra. The sales clerk looked at me, and said to Mom, “How old is your other daughter?”

“Eleven,” mom replied.

“You know, you might as well buy her a training bra now, even if she doesn’t need it at this time. That way she will be used to wearing a bra when the time comes when she will need it.” Emma chuckled at this comment.

Both Emma and I went home from the store wearing bras. When we were home, we compared them. “I’m sorry for horning in on your experience of buying your first bra,” I told Emma.

“That’s all right,” she said, “It was a neat ‘sister’ event. At least now that you have your own bra, you won’t think of snapping my bra straps” She paused and a wicked smile appeared on her face. “You going to wear it to school?” she asked.

“Hardly,” I said.

Over the next few years, Emma and I became more and more like sisters. We were able to share the development of her breasts and her first period. “You should be happy that you’ll never have to experience this,” she commented. However, I learned a lot, and knew how to act when I had a ‘pretend’ period.

* * *

Because of my close relationship with my sister, I did not have a lot of male friends. One of my few friends was Steve, who I had known since grade school. While some of my male acquaintances commented that I was acting ‘girly’ at times, Steve and I had a close friendship and when I slowly became more ‘girly’ he didn’t notice because the change was gradual.

While I didn’t have a lot of male friends, I did have a number of female friends. None of these acquaintances were of a romantic nature, but because I was in touch with my feminine side, I was almost treated as one of the girls.

Steve and I entered the same high school at the same time, and shared many of the same courses. I had always been a good student and Steve and I would study together. As a result of helping Steve, I gained a greater understanding of the course material, which did good things to my grade point average.

Our high school hosted several dances over the year: Homecoming, Halloween, Winter, and Valentine’s day. All students were encouraged to attend, but since freshmen were at the bottom of the ‘pecking order’ most were unable to find a date. Because I was friends with a lot of girls, I was able to arrange dates for quite a few of my male acquaintances, but, unfortunately, not for myself. “You’re a great guy,” one said, “but not macho enough.”

While Steve may have been macho enough, it became readily apparent that he was deathly afraid of girls. Even with my intervention, he was unable to get a date for the Homecoming dance. Both Steve and I attended, since it was permitted to go ‘stag.’ I enjoyed myself. Over the years my sister had taught me to dance. When this was discovered, I had no shortage of dancing partners. Steve, on the other hand, was not a good dancer and was too afraid to ask a girl to dance.

On the Monday afternoon after the Halloween dance, Steve and I were studying together. “You seem to have had more than your fair share of dancing,” he commented with a trace of bitterness.

“You’ve got to get over your fear of girls,” I suggested.

“How am I going to do that?” he asked.

“Let’s pretend that I’m a girl. Now try out a pickup line,” I suggested.

“Okay, he said. “Here it goes.”

“I don’t suppose that you’d want to dance with me?” he tried as a pickup line.

“Way too negative. It sounds like you want the girl to refuse and you’re leaving them an out. A girl might say that she’s guarding the purses for the other girls who are dancing. She might say that her boyfriend is in the washroom. She might say that she doesn’t like the song the DJ is playing. That won’t work.”

“Then what could I say?”

“How about: ‘I could see your aura from across the room, and I just have to dance with you’.”

“I could never say that,” he responded.

“Okay, then pick out a girl who is less attractive. Approach her and say: ‘I’d like to dance with you.’ and hold out your hand to her. Don’t look for the prettiest girl, look for a girl who hasn’t been asked a lot. Of course, she might be as afraid of boys as you are afraid of girls and shoot you down.” I explained.

“Well, anyway, I’m a lousy dancer,” he said.

“Then you need to practice,” I responded.

“Who will I get to practice with?” he asked.

I didn’t answer him. I would love to dance with him as a girl, but I wasn’t ready to reveal that secret to him. We spent the rest of the afternoon grinding through algebra.

Later that week I asked Emma if she would teach Steve to dance. “Why don’t you do it?” she asked, “you’re a better dancer that I am, and you know the girl steps.”

“You know why I can’t do that,” I answered, “my secret might come out.”

“How?” she said, “Does your feminine side have a crush on Steve?”

“Not just my feminine side,” I admitted.

“Your crush is going to go nowhere until you tell him.”

“Maybe, but not just right now,” I said as an excuse.

* * *

That week I suggested to Steve that I teach him how to dance. “But you’re not a girl,” he complained.

“I don’t see how that makes a difference. It’s not like we’re going to kiss or have sex with each other,” I responded icily. The idea of kissing Steve pleased me, but I couldn’t let him know that.

We cleared an area in the rec room, and I plugged in a boom box. From dancing with my sister, I had a fair collection of CDs appropriate for teaching dancing. Steve and I started with fast dances, everything from classic swing to acid rock.

After quite a few dance lessons, I decided that Steve needed to learn how to dance slow dances. “Slow dances are more than hugging on to each other and aimlessly shuffling around the floor. There is a proper way to hold on to each other, and there are definite steps you have to learn,” I explained as I put a CD of waltzes in the boom box. “Now here’s how we do this. Come over and face me. I’ll put my left hand on top of your right shoulder, and you put your right hand around me on my back. Now you put your left arm out to the side, and I’ll do the same with my right, and we clasp our hands. Got it?”

“You’re supposed to lead, which means that when you want to go forward, I can feel it with my left hand. When you want to go backwards you pull me with your right hand on my back. You indicate turns with your other arm,” I added.

“This is too complex,” he complained.

“No, it’s not. Think of all the people you’ve seen dancing slow dances. They learned,” I responded.

“Now for the footwork for a waltz. It is in 3/4 time, and you count one, two and three, with emphasis on ‘one’ when you step forward with your left foot, and I step back with my right. On ‘two’ you move your right foot forward and to the right. On ‘three’ you bring your left foot next to your right. You then reverse the process. This is a box step, and you pretty much stay in the same place when dancing. I think that we’ll save the more complex stuff for later, after you’ve mastered the box step,” I explained. “Before we try it to music, I’ll count it out slowly until you get the hang of it.” Steve took me in his arms and we went through the drill. Being held by Steve was one of my long standing fantasies, and I enjoyed every second of it.

I then put on some music, and we danced. “You smell kind of nice; a little girly, but nice,” he commented as we were close to each other.

“Yeah, I grabbed my sister’s body wash by mistake this morning,” I said. It wasn’t by mistake. I wanted to smell girly for Steve.

As we continued to waltz the box step, Steve and I moved closer to each other. Whether by mistake or intent was not clear, but I liked it. After a while our bodies were touching, and at that point I could feel Steve getting an erection. A few minutes later, Steve suggested we take a break, and he sat down on the sofa. I joined him there, sitting as close as I could to him. I could see his trousers ‘tenting’ over his erection. He noticed my interest.

“I don’t know why that happened,” he said as an explanation, “it just did.” I was glad that I had ‘tucked’ and my penis was held firmly by my panties, so I didn’t have a visible tent. That didn’t mean that I didn’t have an erection. I did, but it was concealed and a little painful.

“Did I turn you on?” I asked coyly, knowing full well that was exactly what happened. “Do other boys make you hard?”

“No, it’s never happened before,” he said, “it’s just that sometimes you seem to be a lot like a girl.”

“But I’m not. We can sit here until it goes down, or you can go into the bathroom and deal with it,” I suggested.

“Or you could do it for me,” he said with a foolish smile on his face.

“Not a chance,” I responded, even though I really wanted to do so.

Over the next weeks, every time we danced a waltz, Steve got an erection. I finally decided to do something about it. Before Steve came over I did my hair up in an androgynous style, put on my sexiest panties, which were brief and made of nylon. I borrowed some of Emma’s perfume and put on a tight pair of girls’ jeans. This time I didn’t tuck.

True to form, when we danced the waltz, Steve got hard. We sat down on the couch, next to each other.

I turned to face Steve and said, “Steve, I need a truthful answer from you. Remember that you said that I turn you on? Do you think you’re gay?”

Steve paused to contemplate an answer. “I’m not sure. I’m not attracted to any other boys, and sometimes you seem to be more a girl than a boy. You look like you’re wearing girls’ clothes and you sure smell like a girl, not that I’m complaining.” With this last part he smiled. “If you put on a dress and some makeup, you’d be a pretty girl.”

Steve looked at the bulge in the crotch of my jeans. “Looks like I’m not the only one who’s turned on.” With that I blushed. “You even blush like a girl,” he added.

“If I was a girl, would you try to kiss me right now?” I asked him. He didn’t verbally reply, but rather put his hand behind my head, pulled me toward him, and kissed me.

“Does that answer your question?” he said.

“It certainly does!” I said, and with that I kissed him back. “Steve, I have to confess that I wish that I had been born a girl, and one of these days I just may do something about it. By the way, I think what we said and did today should remain a secret from everyone else.”

“Does that include me?” came a voice from the doorway. It was Emma. “Am I interrupting anything, I hope?” she said, “because it certainly looks that way. Not that I’m sorry, of course,” she added with a snicker. “Margaret, we need to talk, and soon,” she added.

“Who’s Margaret?” Steve asked.

“I am. That’s my girl name when I’m dressed as a girl,” I answered.

“Does Mom know that you and Steve have been kissing?” interjected Emma.

“It’s our first kiss!” I said as an answer to her question.

“Awwww,” responded Emma, her voice dripping with insincerity, “I interrupted a first kiss. Isn’t that so sad?” and with that she chuckled. “Mom should be home soon, so you two lovebirds better clean up your act,” she added as she left the room.

“I think that you’d better go,” I told Steve.

“Before I go, answer me one question, are you wearing any girl’s clothes now?” asked Steve.

“Yes,” I responded, “These jeans, for a start, and the panties under them,” I answered.

“Could I see them?”

“My panties?” I replied.

“Yes.”

“I guess so,” and with that I unzipped my jeans and slid them down my legs, exposing my panties.

“Wow!” Steve said, “you did this just for me?”

“Yes, but I didn’t expect for you to see them. I just feel sexier when I wear panties, and these are my sexiest.”

“I’m impressed,” he said as he picked up his jacket. “Why are you doing this for me?”

“Because I think I might be falling in love with you.”

He blushed. “Maybe I’d better go,” he stammered. He gave me a gentle smile and left.

* * *

Emma was waiting for me after Steve left. “In my room,” she commanded. “You want to tell me what’s going on?”

“Well, I was teaching Steve how to dance. . .” I started to say.

“I know that!” Emma interrupted, “cut to the chase.”

“I was teaching Steve the waltz, and when we were dancing he got an erection.”

“Just once, or every time?” Emma asked.

“Just about every time,” I answered.

“And what did you do about it?”

“We sat down on the couch until his erection went away.” I said.

“Nothing more? You didn’t jerk him off or give him a blow job?”

“Of course not!” I responded indignantly.

“That’s too bad,” commented Emma.

“You mean that I should have?”

“I bet that Steve would have liked that,” answered Emma, “but of course it probably would have been better if you were wearing a skirt at the time.”

Between Emma and me, we decided that I would dress completely for the next dance lesson. I wore a royal blue dress with a mid-thigh hem. It had a full skirt which was gathered at the waist, and a loose bodice with shoulder straps. At Emma’s insistence, I wore nylons and a garter belt, a bra stuffed with socks, a slip with a lace hem, and my black patent leather pumps.

When Steve arrived, he was astounded. “Wow, you look great. Even prettier than I imagined.”

We started dancing, and almost immediately he began to get aroused. I was almost certain that his reaction was partly due to the way I was dressed. “You got dressed up, just for me?” he asked.

“A girl wants to look good for her special guy,” I responded. We sat next to each other on the couch, our bodies touching. I intentionally let the skirt of my dress ride up, exposing the top of my nylons and the tips of the suspenders from my garter belt. This really caught his attention.

“Remember the first time it happened, and you asked me if I wanted to do something about your arousal?” I asked.

“Yes,” he replied.

“Is that offer still open?” It was, and this time I did something about it.

* * *

With Halloween just around the corner, Steve’s dancing lessons were over, and the topic of discussion became the Halloween dance. “You wanna go to the dance?” Steve asked.

“I might,” I answered, “but the big question is what to do for a costume.”

“How about Snow White or something like that?” he asked.

“No dress,” I exclaimed, “Remember I have to show up at school on the Monday after the dance, and I don’t want anyone having seen me in a dress.”

“But if you don’t look like a girl, I can’t take you as my date,” he complained.

“Then we’ll have to go stag,” I concluded, which is what we did. There were a fair number of girls there without dates, so neither Steve nor I were wanting for dance partners.

That pretty much set the tone for the remainder of my freshman year and all of my sophomore year. What changed at the beginning of my junior year was that I had a driver’s license. Not only a license, but also my own car. It came from my Mom’s Aunt Beth. Aunt Beth failed her renewal driver’s license test, but she had a car, which she gave to me under the proviso that I would chauffeur her around on Saturdays and two evenings a week. This was a small price to pay for having a car. What was even better was that Aunt Beth kept title to the car, which meant that she paid for the insurance and repairs, and she gave me money for gas. My Aunt had first made the offer to Emma, but Emma turned it down.

Aunt Beth liked to go to ladies events, such as bridge parties, all of which were all female. On one of the Saturdays I drove Aunt Beth to my house to visit with Mom. During the visit she mentioned these all female events.

“It’s a shame that Jason isn’t a girl. If he were, he could participate with all of the ladies,” Aunt Beth commented.

“That shouldn’t be a problem,” my Mother said, and she explained my cross dressing in detail. “Not only that, but Jason sometimes wishes he was born a girl,” my Mother added. With that, my Mother asked me to join her and Aunt Beth in the living room.

“As you know, your Aunt goes to a lot of affairs which are for ladies. It might make sense if you dressed as a girl when you took your Aunt to them. Why don’t you go upstairs and come back down as a refined young lady?” Mom asked. I couldn’t very well refuse, given that the car was in the balance. Actually, I didn’t want to refuse, because it would give me more opportunities to dress. Therefore, I did as I was asked.

One can imagine the surprise on Aunt Beth’s face when I came back down. I was wearing a knee length pleated dark blue skirt, a white blouse with a ruffled front, pantyhose, and black pumps. Naturally, I was also wearing panties, a half slip and a bra. I had brushed my hair in a girl’s style, put on some mascara and lipstick, and wore some simple jewelry.

“Oh dear,” my Aunt exclaimed, “you look absolutely darling, much better than I imagined.”

“Give your Aunt Beth a twirl,” suggested my mother. Since I liked the feeling when I twirled, I immediately complied. Mom explained that I used the name Margaret or Peggy when dressed as a girl, much to Aunt Beth’s approval.

Aunt Beth suggested that I spend weekends at her house, as Margaret, and only arrive and leave as Jason. This was not a problem, because I liked being Margaret as much as possible. Then there was an additional benefit. I could go out on dates with Steve while dressed as Margaret. Some Fridays, when Dad wasn’t around, I would dress at home for a date, and arrive at Aunt Beth’s house already dressed. I could also go out on Saturday evenings when Aunt Beth did not have plans for the evening.

Living at Aunt Beth’s house improved my femininity. Aunt Beth would gently correct any of my mistakes in poise and deportment.

I only had a few chores, because Aunt Betty had a housekeeper who came over on the week days. Usually the housekeeper had left by the time I arrived on Friday evening. Not only did the housekeeper take care of the cleaning, but she also did the laundry, including my laundry.

Because I changed back to Jason before I left on Sunday, I had some of my boys’ clothes in my room. On one Friday afternoon I arrived earlier than usual, and the housekeeper, Mrs. Benson, was still there. Since I was dressed as Jason, she wanted to know who I was.

“Your Aunt didn’t say anything about a Jason, so who are you?” she demanded.

“When I’m here, I’m Margaret,” I replied. “Now I have to change into Margaret,” I added and went up the stairs.

Mrs. Benson followed me upstairs and into my room. “This I’ve got to see,” she said. I couldn’t see any harm in it so I took off the clothes I had worn to school. As was usual, I wore panties under my school clothes, so these stayed on. I put on a bra, pantyhose and a half slip. This I followed with a cream colored blouse and a tan skirt. For footwear, I selected a pair of loafers. I then applied makeup and did my hair up in a feminine style. All the time, Mrs. Benson studied my progress from a teenage boy to a girl.

I must note that Mrs. Benson was in her forties, and rather nice looking.

When I was finished dressing, Mrs. Benson came over and rearranged a stray hair. “Better,” she said, “so tell me, do you like dressing as a girl, or is all of this your Aunt’s idea/”

“I like being a girl. It just so happens that living here allows me to satisfy that desire,” I said.

After Mrs. Benson had left, I asked my Aunt about her. “It seems that she was married some time ago,” my Aunt said, “I’m not sure what happened to Mr. Benson, but he appears to be totally out of the picture at this time. She had great references, and she has made my life a lot better and easier. I really don’t know much about her personal life or what she does on weekends, and I really don’t care. By the way, if she causes you any problems, just tell me and I will take care of them.” I accepted her story at face value at the time, only to find out otherwise a short time later.

One Friday afternoon, I again arrived at the house before Mrs. Benson had left. As before, she followed me to my room to supposedly ‘help me dress.’ While I was standing there wearing only my panties and bra, Mrs. Benson went to the closet and picked out a dark blue dress. “Why don’t you wear this?” she suggested. Since I liked that dress, I had no objection to her suggestion. She stared at my light pink panties and white bra. “You can’t wear those panties and bra with this dress, you need a darker color. I noticed that you have some nice black panties and a black bra. Let me get them for you,” and with that she went over to the dresser.

She handed me the panties and bra ans said, “Here, put these on.” Having lost most of my modesty around other women, I complied with what she said. I sat on the bed to remove my pink panties, and while doing so, I noticed Mrs. Benson staring at my private parts. Although she said nothing, I did hear her making a humming sound, as if a sound of approval.

Before she left, Mrs. Benson told my Aunt that there were some things she hadn’t finished doing, and said that she wanted to come over on Saturday to take care of these loose ends. My Aunt would be at a church function all day on Saturday. “Maybe Margaret could drop you off at the church and then come back to give me a hand,” Mrs. Benson suggested, “there are some things I want to do that are a lot easier if two people do them.”

My Aunt had no objection as long as I was at the church by three o’clock to pick her up. Mrs. Benson assured her that we would be done long before three.

That Saturday I put on a plaid miniskirt, with a pink cashmere sweater over a camisole, and thus clad, took my Aunt to the church. When I returned to the house, Mrs. Benson was already there, wearing a pair of black slacks and a white blouse. I silently wondered if she was wearing black panties and a white bra, given how she had told me to wear dark panties under dark clothes, and a white bra under a white blouse.

We immediately got to work, and by eleven we were finished. “Let me fix us some lunch,” Mrs. Benson suggested. Naturally, this was fine with me. I sat at the kitchen table while Mrs. Benson made a casserole for lunch. “I’ll just pop this in the oven and we can relax until it’s ready,” she said. After the casserole was in the oven she walked behind me and began to massage my shoulders. “We did some heavy lifting today, and this will prevent any cramps in your shoulders,” she said. I just sat back there and enjoyed the massage.

“You’re sixteen, aren’t you?” she asked.

“I turn seventeen on April 20th,” I responded.

“I have seen with my own eyes that you are a boy, yet you like dressing as a girl. In fact, if I didn’t know I would swear that you are a girl. Do you want to become a girl?, she asked.

“I’m not sure,” I answered. “I’ve dressed as a girl since I was seven, but only occasionally. You see, while my Mother doesn’t mind it, my Dad is strongly against it, so I’ve had to hide it from him. If I decided to become a girl, I know that I would disappoint him. I love my Dad, and I’m not sure that I want to do that to him.”

“One thing I’ve learned is to consider my feelings first, and not let another person control my life.” Mrs. Benson said, “Maybe as a teenager, you need parental control, but when you are older and on your own you have to consider your feelings.”

“I really don’t want to make up my mind right now,” I responded.

“I can see that, and I understand. Just remember what I said when you are older,” she said.

“Well, what would you do?” I wanted to know.

“I know what I would do, because I did it,” she replied. You see, I was born a boy. I’m really George Benson. I got married, but my wife hated my cross dressing and she left me. Not long thereafter she was killed in a car crash, and I just sort of adopted her identity. You have to promise that you will keep my secret. I really like this job.” So much for the story that my Aunt had fed me about Mrs. Benson. There just had to be more to this.

“Okay,” I responded. “But how did you get references as a housekeeper?”

“By the old fashioned way, I earned them. You see, I was in my mid twenties when my wife left, and shortly thereafter I had my first job as a housekeeper. Those people didn’t need references, but at each job thereafter I accumulated quite a few references.”

“Did you take hormones or have a sex change?” I asked.

“Hormones, yes, sex change, no.”

“So, if I might ask, you still have a dick?”

“Yes, and it’s functional.”

“That must get in the way of relationships,” I mused.

“Yes and no,” she replied, “there are a fair number of people who like a woman like myself. One final thing before we drop this topic; I’m a member of the Dalton Gender Society, a transgender group, where there are people who are going through or have gone through what you are going through now. If you’d like, I can take you to a meeting sometime.”

“I just might want to do that,” I said.

* * *

My arrangement with Aunt Beth worked out well with me. She had re-taken the driving test and passed, but she still let me have exclusive use of the car, I was able to dress, and life went on. It was mid December when my Aunt talked to me about Christmas. “You Mother has invited me to spend Christmas at your house, which should work out well for both you and me. I’d like to go to the midnight service at my church, and, if you don’t mind, I’d like you there with me as my niece Margaret. All of the ladies at All Saints seem to like you and have asked if you would go with me. Please think about it.”

“Then there is the matter of Christmas presents,” she added. “I’ve enjoyed your time with me, and I’d like to give you some money in appreciation. However, there is more. Mrs. Benson and I agree that you need some new clothes and maybe a new coat. We know that your Dad doesn’t approve, so we were thinking about taking you on a shopping trip before Christmas, and leaving all of the new clothes here. Naturally, there will be other presents for you to open up on Christmas morning, but nothing too girly.”

I was overwhelmed, and gave my Aunt and Mrs. Benson big hugs.

* * *

I didn’t know that shopping for clothes could be so much fun, except for a visit to the corset shop. Frankly, I didn’t know that there were any left in business.

“My I help you ladies?” the clerk asked.

“Yes, my niece has a delayed development, so she needs some help,” my Aunt said.

Mrs. Benson jumped right in. “She needs some padded panty girdles and a corset to bring down her waist. Maybe with bra cups on top for some breast forms.”

What followed was a procession of foundation garments, with my Aunt and Mrs. Benson commenting on each. I did have a little surprise when the clerk and I were in the fitting room. “You’re really a boy, aren’t you?” she asked.

When I blushed she had her answer. “Don’t be offended. A lot of my customers are like you, and I value their business, so I want to do a great job on you, not that you need that much help. By the way, when you walked into my shop I commented to myself that you are a very pretty girl. I was sure that the stop was for one or both of the other ladies. I see now that I was wrong. Those two ladies obviously approve of what you are doing, and I assume that they know that you are a boy.”

“They do, and I am thankful of their approval,” I said.

“By the way, no one mentioned a gaff. Do you know what that is?”

“I’ve heard about them, but I don’t have one,” I responded.

“You should have at least two. I’ll see that you get them.”

When we were finished with the purchases, my Aunt said, “keep that corset on, because we are going to buy you clothes to fit your new shape.” And buy we did. I never had so many clothes.

It Started On A Rainy Afternoon - Part 2

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • She-Males

Permission: 

  • Posted by author(s)

It Started On A Rainy Afternoon - Part 2
By Pentatonic

I was enjoying my new situation. The food at my Aunt’s house was a lot better than at home, and under my Aunt’s supervision I was becoming a quite good cook. The parties my Aunt threw, about one every two months, were spectacular. Aunt Beth hired kitchen staff and maids for the occasion, but still there was a lot for me to do, not that I minded it, since a side benefit was that Aunt Beth wanted me to have a new party dresses or cocktail dresses for each occasion.

My Aunt was a supporter of the arts, and there were concerts and plays to attend, along with art gallery showings. Some times I was even able to get an invitation to bring Steve along. While invitations were extended to Emma she mostly declined, because she had no interest in serious drama or classical music. Even with the social events, my Aunt made sure that I had time to study, so I kept up my grade point average. This meant that there was talk of academic scholarships, which would be necessary if I even hoped to go to college.

Finally my seventeenth birthday was just around the corner. Unfortunately for me, I share a birthday with Adolf Hitler. This caused great merriment among my classmates, who began calling me ‘Adolf’ and ‘der Fuhrer’ much to my chagrin.

On the weekend after my seventeenth birthday, Mrs. Benson was coming in on Saturday to ‘clean up some loose ends.’ Since this didn’t concern me, I was luxuriating in a huge bathtub which was part of my en suite bathroom. My reverie was interrupted when I heard the bathroom door open, and Mrs. Benson walked in. “Happy belated birthday,” she said. Thankfully I had put lots of great smelling bubble bath in the tub so I was mostly covered with bubbles. “Let me wash your back,” she offered. “Move forward a bit and sit up straight,” she commanded.

“Thanks for the offer, but I don’t think I need my back scrubbed,” I responded.

“Nonsense,” she countered, “everyone needs their back washed.”

There was no real option except to comply since it was not really possible to just get out of the tub. So she started on my back. That was okay, but then she began to wash my chest, paying special attention to my nipples, which, even though small, began to react to her ministrations.

“I really would like to kiss and lick your nipples,” she said. I began to get embarrassed.

“No, you may not,” I said. Her rubbing was also affecting a different part of my body, which, thankfully was covered by bubbles. Unfortunately as my member grew, it became clear that there were not enough bubbles. She reached into the tub and put her hand around my penis. “Congratulations, birthday boy, you’re now over the age of consent,” she said.

So that was it, I thought, She’s obviously had designs on my body, but was only restrained by the law. Finally, and in no uncertain way, I commanded that she leave the bathroom, or I would tell my Aunt. That did it, and she left. For the next several weeks she was decidedly cold toward me.

* * *

Then, out of the blue, she renewed her offer to take me to a Dalton Gender Society meeting. The meeting was on a Wednesday evening and we agreed to meet at her apartment. Since my Dad went bowling every Wednesday, I was able to get dressed at home. I packed a bag with my boy clothes with the hope of changing into them before I arrived back home. I decided to wear a matching dark blue skirt and jacket, over a cream colored sleeveless top. This meant dark panties, but a white bra. I also put on dark blue pantyhose, and wore my pair of black pumps. I fussed with my hair, and put on some mascara and lipstick.

When she met me at the door, she had a huge smile on her face. “My, don’t you look sweet,” she said as she gave me a perfunctory hug, but no kiss. However, as she broke off the hug, I could feel her hand rub my backside. On the way to the meeting, Mrs. Benson told me that she went by the name of Gloria, and asked that I used that name when talking to or about her at the meeting.

“You may call me Gloria any time you wish, except those times when your Aunt would prefer that you call me Mrs. Benson,” she instructed.

The meeting was both instructive and enjoyable. We arrived when most of the other attendees were present. I must have made an impression, because when we walked into the room, all conversation ceased as everyone looked at me. Angela, the leader of the society came up to welcome me. She looked me up and down, checking me out and turned to address Gloria. “You have a very pretty girlfriend,” she commented, “are you now interested in girls?”

“Margaret is a lot like me,” Gloria said, “she was born a boy.”

“I would never have guessed it,” Angela replied, “when the rest of the girls find out they’ll all be envious.” She then turned to me. “I bet that all of the girls will want you to tell them how you manage to look so pretty and so feminine.”

I just smiled in return.

A few minutes later, Angela called the meeting to order. “I would like all of us to welcome Gloria’s friend Margaret, who, I understand, was born Jason.” This revelation caused mummers of conversation among all present. “Maybe we can encourage Margaret to tell us something about herself, such as how she makes herself looks so gorgeous,” Angela added. Gloria gave me a push to go up front, at which time Angela handed me the microphone.

“I am seventeen and a junior in high school,” I began. “As you can guess I go by the name of Jason in school, and only one classmate knows that I am also Margaret. Going to school dressed like this may cause too many problems and may also be dangerous, since my school has its fair share of neanderthals. I have a sister Emma, and I almost look like her twin, which is a good start for my appearance. Emma has been my prime support and has helped me in all aspects of appearing to be a girl.” I then described the history of my cross dressing.

“That was very interesting,” commented Angela, “maybe you could tell us about your plans for the future, and how we can help you.”

“I don’t have any definite plans, other than keeping the status quo until I graduate/ After that, I just don’t know. I know very little about being transgendered, and I am hoping that all of you can share your experiences with me and give me your opinions of what I could do.”

“Do you have a boyfriend?” one of the girls asked.

“Sort of,” I answered. “I hope to develop the relationship, but I’m not sure how to do it.”

“How do you know Gloria?” another asked.

“I spend weekends at my Mother’s Aunt Beth’s house and help my Aunt. Gloria is my Aunt’s housekeeper, and that is how we became friends. Gloria suggested that I attend this meeting to help further my plans for the future.”

Finally I was allowed to relinquish the microphone and sit back down next to Gloria, who put her hand on my knee and whispered, “You did so well up there, All of the girls loved you. I’m so proud of you.” With her last words to me, Gloria rubbed her hand up and down the inside of my thigh.

“I’m getting aroused,” I whispered, “maybe you had better stop that.”

“Spoil sport,” commented Gloria with a smile, indicating that she was not offended with what I said.

After the meeting broke up at about nine, Angela mentioned that some of the girls would be going to a TG friendly bar for a few drinks, and that maybe Gloria and I would like to join them.

“I appreciate the invitation,” I answered, “But I have to be in school tomorrow, and I am too young to have a drink, but thank you anyway.”

A few minutes later, Gloria indicated it was time to go. When we were in the car, she turned to me. “You had them eating out of your hand. You were great.” With that she leaned over and gave me a kiss on the mouth. Perhaps due to the excitement of the evening, I kissed her back. “That was great,” she said, in reference to the kisses. “It looks like you enjoyed it too.” With that I could feel her hand move up my thigh and under my skirt where it remained all the way back to Gloria’s apartment.

“Would you like to come in for a few minutes?” Gloria asked.

“It’s getting rather late. Maybe I’ll come in to change back to Jason, in case my Father is still up, so after I change I better go home so I don’t fall asleep in class,” I answered.

* * *

The next day Mrs. Benson was at my Aunt’s house when I arrived. “I enjoyed your company at the meeting last night,” she said, “did you get any useful information from any of the girls?”

“A few of them suggested that I look into hormone therapy, since I am as flat as a board. Some even suggested breast implants,” I answered.

“In my opinion, if you are seriously thinking of transitioning into a girl, you should consider either or both,” she responded. “Of course you will need to see a doctor and a counselor before you start. Do you have a doctor?”

“My family has a doctor,” I said, “but he’s a bit old fashioned, and probably wouldn’t be of much help.”

“Why don’t you ask your Aunt if she has any ideas?”

I did, and before long I had a doctor and counselor, both of whom were familiar with gender matters.

The doctor was very helpful. “It may be a good idea for you to start some hormone therapy at this time. Because you have another year in high school, we have to proceed carefully. I don’t imagine that growing large breasts before you graduate would be a good idea. I would recommend a testosterone blocker to more or less keep the status quo. After you try this for a while, we might add some estrogen.” I then had my prescriptions.

My new counselor and I discussed my transition. “You should be sure that you want to go through with it,” she said. “If you want to undergo sexual reassignment surgery, you have to undergo a year of real life experience, where you dress and act as a female, all day and every day for a year. I think that we can agree that you want to graduate from high school before you start that.”

“I agree, since my Dad is dead set against me wearing any feminine clothes at home,” I volunteered.

“I see,” she said, “You will have to resolve your issues with your Father sooner or later. I would like to explore your options with you, and maybe we can come up with a plan.”

My hormone therapy did gradually result in some physical changes. I was delighted to discover that my nipples and areolae grew larger and darker. I even noticed that I was developing breasts. Unfortunately they sometimes itched. One such time was when Steve and I were riding home from school. I couldn’t help but rub my budding breasts.

“What are you doing?” he asked.

“My breasts itch,” I replied.

“Why?”

“Because I’m taking medicine that makes them grow.” I replied.

“Can I see when we get to your house?” he asked.

“No,” I answered.

When we arrived at my house he renewed his request. “There isn’t much to see,” I said.

“Then can I touch them?”

“Definitely not!” I asserted, even though I wondered how it would feel if he fondled them.

* * *

Steve’s seventeenth birthday was coming up shortly, and after I confirmed that my Aunt had no plans for Saturday evening, I invited him to a dinner to celebrate. “As Margaret or as Jason?” he asked.

“As Margaret,” I answered.

On the Monday following my dinner with Steve, I went right from school to my Aunt’s house. Mrs. Benson was still there when I arrived. “Your Aunt told me that you had a date with Steve this last weekend,” she commented. “How did that go?”

“Great,” I replied.

“Did you seduce him?” she asked with a leering smile.

“Hardly,” I said, a little miffed.

“Too bad,” she responded.

My conversation with Emma a few days later was a repeat of my conversation with Gloria.

“You know, I think that you are teasing poor Steve. Remember, as a boy he has certain needs.”

“I know,” I answered, “because I have the same needs.”

“Then you should do something about it,” she said.

“Maybe he would like it if I did something for him, but I’m not sure that he would want to reciprocate,” I added.

“You’ll never know if you don’t try,” Emma said, “unless there is some romance, he may lose interest in you and find a new girl friend.” I didn’t like this alternative.

“What do you suggest that I do?” I asked.

“He probably would love it if you gave him a blow job,” she answered, “after all, both of you are above the age of consent.”

“But I don’t know how,” I complained.

Emma made a sound of disgust. “It isn’t rocket science,” she said, and gave me a graphic description of how to do it.

“Then what do I do?” I asked.

“Swallow it, of course, and lick every drop from him. That should be obvious,” she replied.

“What does it taste like? Is it disgusting?”

“There are two ways to find out,” she said, with a bit of disgust in her voice, “you can either jag yourself off and taste your own cum or you can give him a blow job and find out how his tastes.”

“Do you think he’ll then give me a blow job in return?”

“Probably not, unless he is gay. Is he?”

“I don’t think so.” I said.

“Have you ever touched him?” Emma asked.

“Once, when I jerked him off after a dance lesson.” I answered.

“Did he return the favor?”

“No,” I answered.

“Then it’s quite clear that he won’t blow you,” she said, “it’s one of those girl things, The guys want relief, but won’t return the favor”.

* * *

That Thursday I had a short day at school, so I arrived at my Aunt’s about one o’clock. I went to my room and put on a skirt and top. When I came back downstairs, Mrs. Benson was still there.

“Margaret,” my Aunt asked, “could you drive me to All Saints? There is a meeting which I want to attend, and I would rather you take me than to ask one of the other ladies or Mrs. Benson to do so.”

“Sure,” I answered, “it would be my pleasure.”

When I returned to the house, Gloria came up to me. “How are things with you and Steve?” she asked, and then added, “did you think about what we discussed?”

“All right,” I said in answer to her first question. “And yes, I did think about it. I even discussed it with my sister.”

“And?” she asked.

“Emma thinks that I should give him a blow job,” I said.

“So will you?”

“I’m not sure I know how or even if I could do it,” I said.

“The only way to answer your questions is to try it,” she said.

“But what if I start the process, and I can’t follow through, or if I botch it completely?”

“From my experience that is only a slight possibility,” she said.

“I’m concerned,” I said, “I want to do it right. If only I was sure that I could do it.”

“If that is your problem, I have a solution,” she said, as she took me by the hand and guided me upstairs.

* * *

My next date with Steve was memorable because I was able to do what I had learned, and yes, he did reciprocate.

* * *

During my summer vacation I spent more and more time at my Aunt’s house. While Aunt Beth was out playing bridge one afternoon, Mrs. Benson and I were sitting at the kitchen table drinking lemonade.

“Gloria,” I said, “I have a question for you, but you don’t have to answer it if you don’t want to.”

“Oh boy,” she responded, “That sounds ominous, but ask away.”

“How do you keep your secret from my Aunt?”

“You mean that I’m transgendered?”

“Yes.”

“I don’t,” she replied.

“You mean she knows?” I asked with some surprise.

“Let me put it this way,” she started, “Your Aunt isn’t THAT old. She’s only in her fifties, and she has her needs, which were unsatisfied for several years after she was widowed. She mentioned her dilemma to a cousin of hers, no direct relation to you, who is gay, and who has friends in the transgender community. One thing lead to another, and I was introduced to your Aunt. Because I present as a woman, but can function as a man, she hired me as her part time housekeeper. Since everyone she knew believed that I was a woman, this raised no suspicions. Since I was hired, I can discretely service her needs. To keep up appearances, I call her Madam, Mrs. Yardley or Miss Beth and she calls me Mrs. Benson or Gloria, as would be proper for the occasion when other people are present. We have other names when we are intimate.”

“Will the fact that you took me to the transgender society meeting cause any trouble, if she knows that I know you are transgendered?”

“Hardly,” she responded, “it was your Aunt who suggested that I tell you and take you to the meeting. Her only regret was that she could not be at the meeting, after I told her how well you handled yourself.”

“Obviously all of this must be kept a secret,” I commented.

“In that you are correct. It would be a bad idea if your family found out about any of this, especially considering your Father’s prejudices,” she said. “If you decide to become a woman, hormones and surgery et al, your Aunt told me that she would welcome you to stay with her full time, especially during your one year real life experience,” Mrs. Benson said.

“That’s really kind of her, and you,” I said.

* * *

During the fall of my senior year I began to think about college. While my grades and test scores were good enough to get me admitted to many colleges, I couldn’t make a go of it financially, even with the scholarship I won. There was another consideration. My Aunt invited me to live with her full time, and if I went away to college, I wouldn’t be able to spend much time with her. Perhaps that was the reason she didn’t offer to help me financially.

I applied for admission at Dalton Community College and was accepted. The college has a liberal policy regarding transgendered students, and I was able to enrol as Margaret, even though my high school record identified me as Jason.

I anticipated that I would be looking for a job, and a lot of the courses offered at Dalton Community centered around business and careers. Many of the courses had prerequisites so I signed up for the ones in business and accounting. Dalton also offered courses in gender and women’s studies which seemed interesting, so I signed up for Sociology of Sex and Gender.

* * *

Right after graduation I moved into my Aunt’s house, and became Margaret full time except when I visited my parents and sister. My Aunt and Mrs. Benson seemed to approve of Steve, and he became a frequent guest at my Aunt’s house.

It was at this time that Mrs. Benson often stayed overnight, sleeping with my Aunt in her bed. Given this situation, neither of them seemed to object to Steve spending a lot of time with me in my room.

* * *

Gloria and I had attended quite a few of the gender society meetings, because I found them informative. “You really don’t need me there,” Gloria said as we were in the car going to a meeting. “The reason I go with you is to keep the other girls from propositioning you. When I’m along they consider that you are my date. Before I would turn them loose on you, I’ll have to teach you how to gracefully refuse any propositions, that is, if you don’t want any,” she added with a smile.

It was at this meeting that Angela announced that the society was planning a picnic at a local forest preserve. I was interested, and signed up to bring a German potato salad. After I had done so, Gloria told me that she couldn’t be there and I was on my own. “Be careful,” she said, “I’ve noticed more than one of the girls casting hungry looks at you.”

On the morning of the picnic I arose early and made the potato salad. My Aunt produced a picnic basket with plates, cups and utensils. It had enough room for the potato salad, a soft drink, insect repellant and sun screen. I had purchased a skort just for the event. It was a pair of shorts with a piece in front that made it look like a skirt from the front, and shorts from the rear. I put on a nice pair of panties, and a push up bra which, with my beginning breasts, gave me a hint of cleavage. I also wore a v-neck top to display the little cleavage which did I had. I also wore a pair of tennis shoes. Just a little jewelry and some mascara and lip gloss completed the look.

When I was finished, Gloria and my aunt looked me up and down. “Delicious,” said Gloria, “That’s going to attract a lot of attention. Are you ready for that?”

It was then that I notice Gloria slip something in the picnic basket. When I arrived at the picnic, I discovered that it was a package of prophylactics. As I was walking out the door, my Aunt handed me a plaid blanket. “In case you have to sit on the ground,” she said.

When I arrived at the picnic grove, I saw that quite a few of the members were there, and yes, some were casting hungry looks at me. More than one of them asked if Gloria would be here. When I told them that she would not, a few made a humming noise of approval. After a period of socializing, we got down to eating. I filled my plate, put the blanket on the bench, and sat down. Almost immediately I was joined by two of the girls who had been casting hungry looks at me, one to my right and one to the left. I noted that while there was plenty of room on the benches, my lunch companions were squeezed close to me, with our bodies touching each other. I also noted that while my lunch companions gave me broad smiles, they were casting dirty looks at each other. While eating we introduced ourselves to each other. For some reason, they already knew my name. The girl to my left was Adele and to the right was Teresa, also known as Teri. During the lunch I felt either Adele’s or Teri’s hand rubbing my leg, slowly moving up toward the hem of my skort.

After lunch I decided to explore some of the forest preserve. Once I was out of sight of the grove, Teri joined me. “That’s a really cute outfit you have on,” she said, “and it really looks good on you.”

I returned the compliment, and as we walked on she took my hand in hers. “It’s a shame that Gloria couldn’t make it,” she said, “have you known her long?”

“A few years,” I answered. “I live with my Aunt, and she’s my Aunt’s housekeeper” I volunteered.

“Does Gloria also live there?” Teri asked.

“Off and on,” I answered.

“So she spends the nights there?”

“Some of them,” I answered.

“Gloria is a good-looking woman,” Term observed, “don’t you agree?”

Things appeared to be getting rather personal, so I decided to keep my answers brief. “Yes,” I answered.

“And rather sexy, wouldn’t you say?” Teri asked. I made no answer. “But not as sexy as you,” she continued with a salacious smile.

“Oh, I don’t know about that,” I answered, and with that she took my other hand in hers, so we were facing each other.

She pulled me closer to her and smiled. “I have to confess that I could go for you,” she said with a lowered voice. She let go of my hands, but before I could move away she had her hands on my shoulders. She pulled me even closer and kissed me.

“I’ve been wanting to do that since the first time I met you,” she said. I didn’t reply. She then kissed me again and again. When we separated a bit I looked down and noticed a bulge in her jeans. She saw this, and said, “Yes, you turn me on. Do I turn you on?”

“Not really,” I responded. This produced a crestfallen look on Teri’s face. I decided to soften my answer. “It’s not you,” I continued, “It’s me. You certainly are sexy, but I have a boyfriend.”

“Oh,” she said. “But does he take care of you?”

“Yes,” I responded. With that we walked back to the picnic grove, where I saw Adele giving both of us dirty looks.

I was hit on quite a few more times, which kept me busy until it was time to wrap things up and go home. I then saw Teri approaching me with a concerned frown on her face. “Adele’s really pissed off and jealous. I don’t know if she’ll give me a ride home. If she won’t, will you?”

“Sure,” I answered, and we left. Nothing further happened, except for a brief ‘thank you’ kiss from Teri in front of her house.

* * *

When I arrived at my Aunt’s house, she and Gloria were waiting for me at the kitchen table, both wearing nightgowns and peignoirs. “Well, it looks like you survived,” Gloria said.

“How was it?” My Aunt asked.

“I was hit on more times than a softball at a picnic,” I responded with a big grin.

“But is your virtue intact?” Gloria asked.

“As intact as it was when I left this morning,” I answered.

My Aunt saw that I was staring at their nightgowns and peignoirs. “We didn’t have time to get dressed,” my Aunt said lamely. I gave them a knowing smile.

* * *

As the summer was drawing to a close, one of my Aunt’s friends was throwing a pool party, to which my Aunt, Gloria, and I were invited. My Aunt’s friend had a big house with a good sized in-ground pool. I wished that Steve could be there, but he was already on his way to college. When the invitation was made, I panicked. “I don’t have a swim suit!” While Jason had a swim suit, Margaret did not. I couldn’t attend as Jason, because by now my breasts had begun to be noticeable. I also realized that most stores would not have a good selection of swim wear this late in the season.

“Well,” my Aunt said, “We’ll have to go shopping and see what’s left.”

“Wear your gaff,” Mrs. Benson whispered to me. Even though the selection was poor, I was able to find a one piece that had a short skirt built in. There was also a matching cover up.

Most of the people at the pool party were older, around Mrs. Benson’s age, however there were a few who were around my age. One boy looked familiar to me. When he saw me, he smiled and walked over to me. “Hi, my name is Terrence, Terry for short,” he said.

“I’m Margaret, Peggy for short,” I answered.

“I know that,” he said, and at that point I recognized him. He was Teri from the gender society picnic.

“Is Adele here?” I asked.

“No,” he responded. “How about your boyfriend?”

“He’s away at college,” I answered.

“Are you college bound?” he asked.

“I’m going to Dalton Community.”

“How come?”

“Money, the usual problem,” I said, “My Dad doesn’t approve of me as Margaret, and he wouldn’t cosign any student loans for me. How about you, are you going away to college?”

“I’m going to college, but not away. I start at Salem Tech next week. Hey, maybe we could hang around together if you’re not mad at me for hitting on you at the picnic.”

I laughed. “If I was mad at everyone who hit on me at the picnic, I’d need a data base to keep their names straight. Actually, I’m flattered with the attention you showed to me.”

“I’d ask you for your phone number if I could find a piece of paper and a pencil,” he said.

“Are you still going to the society meetings?” I asked.

“I haven’t for a while, but if you’ll be there, I’ll be sure to show up,” he said.

“Okay, I’ll be there, but I caution you, so will Gloria, and she keeps a close eye on me,” I said.

“What’s it with Gloria, anyway?” He asked. “She’s old enough to be your mother.”

“It’s a very long story. Maybe I’ll tell you someday, and then again, maybe not.”

I rejoined my Aunt and Mrs. Benson. “Who’s your friend?” my Aunt asked.

“Someone I met at the gender society picnic,” I answered. “I don’t know his, or her, last name.”

* * *

A few days before my college career was to commence, Aunt Beth, Gloria and I were having coffee at the kitchen table. “What do you plan to wear?” asked Aunt Beth.

“I didn’t see any dress code in the catalog,” I commented.

“Maybe not,” continued Aunt Beth, “but if you are studying business, you should look like you mean business.”

“You mean no student grunge?” I responded with a grin.

“Precisely,” Aunt Beth answered. “Dress as if you were working in an office. For the first day you might want to over dress: Pantyhose, dress flats, a nice skirt and a conservative top.”

“No flashing cleavage?” I rejoined, but not seriously.

“Well, maybe a little,” my Aunt conceded.

For my first day at Dalton, Aunt Beth and Gloria decided to help me get dressed. When I came out of the shower, they had laid out their selection of clothes on my bed. There was a pair of nude pantyhose, nice panties, a white half slip, a pink plaid pleated skirt, a push up bra and a pink silky nylon long sleeved blouse. After I was dressed, Gloria picked out a pair of hoop earrings, a necklace with a heart pendant, two simple bracelets and a nice watch.

“Let me fix your hair,” Gloria offered, which she then did. A little mascara and lip gloss completed the look. I went to the mirror to admire the finished product.

“Leave enough buttons open so people can see your necklace,” suggested Aunt Beth. They could also see some cleavage.

My first class was Introduction to Business. When I walked into the classroom, I could feel a lot of eyes checking me out. The boys seemed to approve, but the girls just gave me dirty looks. All of my classmates were in various degrees of student grunge,

The instructor was a youngish man wearing a mismatched plaid shirt and tie. I noticed with some satisfaction that he could hardly keep his eyes off of me. The tease in me was having a field day, and I let my skirt ride up a bit, exposing a lot of leg.

My course in accounting was met with similar results. After each class, the girls mainly avoided me, but a few boys made a point of introducing themselves to me.

Most of the students in the gender and women’s studies class were, as expected, female. The instructor was a middle aged woman, overweight with a short haircut and no makeup. She wore tan slacks and a plain yellow cotton blouse. No teasing here, I thought.

She introduced herself as Ms. Birch, with emphasis on the ‘Ms.’ She went over the syllabus and an introduction of what we would be studying. “We will examine how the male culture has degraded women, and made them second class citizens. Women are almost forced to dress as men would have them dress,” which statement was directed at me.

After another twenty minutes of lecture, she changed the topic of discussion. “We will also be examining gender. Do any of you know what ‘transgender’ means?”

On of the boys, with a silly grin, answered her, “That’s when boys turn into sissies.”

His answer was met with disapproval by Ms. Birch, and she launched into a diatribe on gender discrimination. While I full well knew the ins and outs of being transgendered, I kept my peace. I figured out that she disapproved of me and the way I was dressed, and I didn’t want her to start on me. But she did.

“Ms., ah,” she paused as she looked at the attendance list, “ah, Cleary, you’re all dressed up. Are you trying to fit into the stereotype that men have set for women?”

I just had to answer this challenge. “No,” I said, “I’m dressed this way as a sign of respect for the faculty of this college. I took the time to look this way because I respect the faculty’s position.”

Ms. Birch didn’t respond to what I said, but returned to her question of the meaning of transgendered. “I don’t suppose that you have any idea of what ‘transgendered’ means, do you?” she challenged.

I was beginning to get offended with Ms. Birch, but rather than telling the truth, I came up with a snotty response. “I hope to learn that by taking this class,” I said. Ms. Birch did not respond.

I considered dropping this class, but decided that I would ‘gut’ it out. I also decided that I would dress down for subsequent classes, not that it would do any good, because I felt that her opinion of me would not change. I wondered what she would think if she knew the truth about me.

At dinner that evening, my Aunt and Gloria were interested in how my first day of classes had been. “I don’t see any problems with the business and accounting classes,” I said, “but I am a little concerned about the gender studies class.”

“Why is that?” my Aunt asked/

“The instructor, a Ms. Birch, seems to have taken an instant dislike of me, just because of the way I was dressed,” and I recounted what had occurred in the class.

“You know, I think that Angela from the society knows Ms. Birch,” Gloria observed, “From what I heard, Ms. Birch likes to champion the rights of gay, lesbian, and transgendered people.”

* * *

The next meeting of the society was interesting. First, Teri was there, and renewed her interest in me, much to the disapproval of Gloria. Second, Angela had asked me to do a short presentation on how to change names and gender identity or markers on drivers’ licenses, birth certificates and the like. My Aunt’s attorney had graciously helped me in this endeavor, and told me how to do a name change. Angela asked me if I was ready for my presentation that evening. I assured her that I was. “Keep it short,” Angela requested, “because we have a guest speaker this evening. Her topic is discrimination against trans people.” Angela paused and looked around the room. “I don’t see her,” she said, “I hope that she will make it. ”

She did.

It was Ms. Birch.

Oh shit!

Because I was making a presentation, I wore a blue dress with a full skirt, gathered at the waist, along with nylons, garter belt and heels. After Angela opened the meeting she asked me to come up and give my presentation and said, “Peggy is one of our newer members and has some information which all of us will find useful.” What happened then was priceless, When Ms. Birch saw me, her mouth dropped open in surprise, accompanied with a look of astonishment on her face. It caused me to smile.

I gave my presentation, and then Angela introduced Ms. Birch as a faculty member at Dalton Community and an activist for transgendered rights. When Ms. Birch stood up and began to speak she fumbled her words at first, all the time staring at me. To her credit, she quickly recovered and delivered what I thought was a well presented and though out presentation.

After the formal part of the meeting, most of the members stayed to talk with each other. Many of the members complimented me on my presentation. I could see Ms. Birch talking with another group, all the time casting glances at me. When she was free, she came over to me. “Seeing you here was a surprise. Seeing you in class, I would never have guessed. You are, aren’t you?” she asked.

“I am,” I said, “that is why I am interested in amending my birth certificate and drivers’ license. Right now they identify me as ‘Jason,’ a male. I’m always concerned that the cops will pull me over, and when they see my drivers’ license I will be subject to some unpleasant discrimination by the police because I am transgendered.”

“I hadn’t thought about that,” Ms. Birch replied, “but it is a good point. I’d like to incorporate that in my course materials.” She paused. “You seem to be well informed. What to you hope to get out of my class?”

“There’s a lot of misinformation out there. I’m sure that you have researched what you say, and what you say will be the truth. For obvious reasons, I am interested in what I will get out of the course,” I responded.

“I can’t get over how feminine you look,” she said.

“Well, isn’t that one of the goals? To look as feminine as possible?” I responded.

“Maybe, but you take it to a new level,” she said with a smile.

“Do boys hit on you?” she asked.

“They do. Actually, it’s kind of flattering,” I said.

“Did you ever hit on girls as Jason?” she asked.

“Sure, and now I know how obnoxious I was at times. You know, I should write a book called ‘How to, and how not to, pick up girls: a primer on what works,’ except the boys who need it the most probably wouldn’t, or couldn’t, read it,” I said with a smile.

“How about girls?” she responded, “do they ever hit on you as Peggy?”

“On occasion,” I answered.

“How do you deal with that?” she asked.

“I tell them that I have a large and jealous boy friend.”

* * *

Gloria was busy with Angela when Teri walked over. “Hi, I hoped to see you here. By the way, a great presentation. Still have the same boyfriend, and is he still away at college?”

“Same boyfriend and still away at college,” I answered.

“Want to go out sometime?” Teri asked.

“As Teri or as Terrence?” I asked for clarification.

“Either way that turns your crank,” Teri responded with the hint of a leer.

“I’ll think about it,” I said.

It Started On A Rainy Afternoon - Part 3

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Transgender

Character Age: 

  • College / Twenties

TG Themes: 

  • Voluntary

Other Keywords: 

  • Fashion Model

Permission: 

  • Posted by author(s)

It Started On A Rainy Afternoon - Part 3
By Pentatonic

About three weeks after I started at Dalton Community Aunt Beth, Gloria and I were sitting down for dinner when I mentioned that I might like to look for a part time job. “Why?” Aunt Beth asked.

“I want to feel productive, and I would like to earn my own money rather than sponging off of you,” I replied, “My class work doesn’t take all that much of my time. I know that it would cut into the time when I drive you around, but if I earn money, and I can pay you something for room and board to make up for it.”

“Let me think about it,” my Aunt said, “What kind of job are you thinking about?”

“Some low level office job,” I replied.

It was several days later that my Aunt was at one of her bridge gatherings, and at dinner that evening she turned to me and asked, “Are you still interested in getting a job?”

“Yes,” I answered.

“The reason I ask is that Dorothy Eames said that she is having problems with getting competent office staff. She has her own business, the Eames Agency, which is a modeling agency here in Dalton. She was complaining that she only wants part time, and the quality of applicants leaves something to be desired. I mentioned to her that my niece is looking for an office job, and she suggested that you call Virginia, her office manager, and make an appointment for a job interview. You will need to make up a resume before you go.”

So the next day I looked up the agency on the internet and decided to call for an appointment. I spoke with Virginia, the agency’s office manager. “Do you have any experience working in an office?” She asked.

“No,” I replied, “I just graduated from high school last spring.”

“Can you use a computer?” she wanted to know.

“Yes “ I said. It seemed silly to ask if a teenager could use a computer, but then there must be some who can’t.

“When can you come in?” she asked.

“I’m pretty much free all Tuesday,” I replied.

“Good,” she responded, “how about ten on Tuesday morning. Bring your resume.”

That evening I reported to my Aunt and Gloria that I had a job interview lined up at the Eames Agency. “Great,” Gloria said, “your Aunt and I will help you get ready. I might suggest that you make an appointment at the salon before your interview. You want to look as great as possible. First impressions count.”

I really didn’t think that I needed supervision when visiting a beauty salon, but my Aunt and Gloria insisted that they go with me, to ‘help make the correct decisions.’ The beautician and the three of us poured over hairstyle books, until the correct ‘do’ was found. I loved the final result. While at the salon, the beautician suggested a make over and my Aunt not only agreed, but offered to pay for it and the cosmetics used. On my way home, I felt really glamorous.

Bright and early on Tuesday morning, while I was in the shower, my Aunt and Gloria were busy selecting the exactly ‘correct’ clothes for me to wear for the interview. When I came back into my bedroom, they had laid out three outfits which they deemed ‘appropriate.’ The one I chose consisted of a cream colored A line dress, with a princess neckline and cap sleeves. Underneath this I wore a white full slip with lace at the top and around the hem line. Gloria suggested that I wear hose and a garter belt, because it would make me feel more glamorous. To go with the dress, I put on some off white hose and a pair of cream-colored shoes. My Aunt and Gloria selected the jewelry which they deemed appropriate, while I started on my makeup. Neither Gloria nor my Aunt could leave well enough alone, and fussed with my hair and makeup. I ended up with tan eyeshadow, pink lipstick and, of course, mascara. Gloria insisted on trimming my eyebrows, to make me more alluring. While I believed that I could have done an adequate job dressing myself, I couldn’t deny them the pleasure of being involved.

On my way downtown a car full of boys pulled up next to me at a light, and the catcalls and whistles ensued. It made me feel beautiful to attract attention, and rather than ignore them, I turned to face them and smiled. Before anything else could happen I made a right turn and they were gone.

When I entered the Eames Agency there was no one at the front desk, but shortly thereafter a nice looking woman appeared, who I assumed was Virginia. “I’m Margaret, and I’m here for a job,” I said. Virginia looked me up and down and smiled with approval.

“Wait here, and I’ll tell Ms. Eames,” she said, obviously not connecting me with her ten o’clock appointment. It was only a minute later when she escorted me into Mrs. Eames’ office. Mrs. Eames did not ask me to sit, but rather came around to the front of her desk.

“Turn around slowly,” she commanded, which I did.

“Very nice,” she commented, and then invited me to sit. “Can I see your portfolio?” she asked. I didn’t know exactly what she was asking, but I did have my resume in a leather holder, and I offered my resume to her. “Where are your photographs?” she asked with a hint of exasperation in her voice.

“I don’t have any,” I responded

“How do you expect me to sign you on as a model if you don’t bring your photographs?” she asked rhetorically and with some impatience. Her question explained the confusion.

“I’m not here for a modeling job, I’m here for an interview for the office job,” I volunteered.

Ms. Eames looked at me for a moment. “Virginia,” she called out, “come here, you’ve sent me one of your flock. She’s not here for a modeling job. She’s here for the office assistant job. Didn’t you make that clear before you sent her in here?”

“She just looked so good, I just assumed that she was here for a modeling position,” Virginia said, “As you know, the office assistant candidates mostly show up dressed like they had just come from cleaning their garage.”

Ms. Eames chuckled now that the confusion was resolved. “No harm,” she said, “you know, you are gorgeous enough to be a model. By the way, do you always dress like this?”

I decided to chance some humor. “Not when I’m cleaning the garage,” I replied.

Both Ms. Eames and Virginia laughed.

“Virginia, have her fill out an information sheet and take her to Joe to get some photos,” Ms. Eames said.

The information sheet which Ms. Eames referenced wanted all of my measurements, along with dress size and shoe size. There was a space for ‘previous modeling’ into which I wrote ‘none.’

I had assumed that the photos would be the standard ID photos, but I was wrong. Joe had a studio with all sorts of lights and backgrounds, and was a professional photographer. He spent a little time looking me up and down, sideways and backward. “Very nice,” he said to himself, “but now let’s see if the camera loves her.” What followed was a series of photographs of me from various angles and in various positions. He even had me take off my dress, lowered the shoulder straps of my slip and bra, and wrapped a black stole like thing around me, leaving my shoulders bare for more photos against a dark background. ‘Head shots’ he called them.

“Let me go through the digital photos and print up a few for Dorothy, he said when he was finished with taking pictures. Just before we left, he motioned Virginia to look at some of the photos on the computer screen. “Dorothy ought to like this. The camera loves her.”

When we were done, Virginia and I went back to Ms. Eames’ office where she was looking at some of the photographs which Joe had shot of me. She was smiling. She put the photos down, and turned to me. “We have an unwritten dress code in this office. You don’t have to get as dressed up as you are, but I do not allow blue jeans and T-shirts. You may wear a dress, skirt, or slacks, and an appropriate top. I do expect you to wear a little makeup, since we have an image to maintain here. If possible, I would like you to wear a skirt or dress every day you are here. I’m looking for you to work about twenty hours a week, and I will pay minimum wage to start, with reviews every three months thereafter. Because you are part time, there are no benefits, although you can sign up for health insurance at your own expense. Now, why don’t you go with Virginia and set up a work schedule.”

When Virginia and I walked to her office, I said, “I assume that since we are setting up a work schedule, that I have been hired.”

“Look here, honey, you were hired the minute Ms. Eames saw you,” she said.

“Why all the photographs?” I asked.

“You mean you don’t know?” Virginia responded, “Ms. Eames is setting up a model portfolio for you. She may send you out on modeling jobs.”

“Oh,” was all I could say.

It was no more that a week later that Ms. Eames came storming out of her office. “I can’t believe it!” she shouted.

“Can’t believe what?” Virginia asked.

“Cindy,” Ms. Eames spat out the name, “we had her set up for a photo shoot today, and she just called to cancel. Virginia, see whom we have available.”

Fifteen minutes later, Virginia reported the bad news. “No luck,” she said, “no one at her rate or below is available. We could send someone who has a higher hourly rate, but it’ll cost us dearly.” While all this occurred, I was sitting at the front desk, entering billing information, so I understood some parts of the crisis.

Ms. Eames came out of her office. “What are we going to do? We can’t afford to lose the client,” she asked to no one in particular. She started to spin around to go back into her office when she stopped halfway through her spin and looked at me. “Stand up honey,” she said to me. I stood up. “I think this will work,” she said to herself. “What do you have planned for the rest of the day?” she asked me/.

“Nothing but some shopping and doing homework. Why?” I said.

“How’d you like to go on a photo shoot?” she asked.

“I guess that it would be okay,” I answered.

Ms. Eames went to a phone. “Jake,” she said, “Cindy cancelled, but I have someone whom you are sure to like. What you’ll really like is that she had just started as a model, and her rate is a lot lower than Cindy’s, so you’ll save a lot of money.” She paused for a minute when Jake talked. “The camera loves her. I have some photos I can send you.” Another pause. “They’ll be on the way in a minute.”

After she completed the call, she turned to me. “Is there anyone at your house who can pack up your makeup and some spare clothes for you? I’m thinking of different colored panties and bras, slips, pantyhose, stockings, garter belts and the like.”

“I think so,” I answered. With that she called my house.

“Beth, this is Dorothy, and I need a favor. I’m sending your niece on a photo shoot, and I need someone to pack up her makeup and some spare clothes, and we’ll pick them up on our way.”

A minute later Virginia held a telephone to Ms. Eames. “It’s Mr. Jacobs. He loves the photos, but wants to know why you didn’t let him use Peggy from the start.”

“I’ll take the call in my office,” she said, “Virginia, give Peggy the address, and have her stop at her house to pick up her makeup and spare clothes.”

“When you get to your house grab your stuff and immediately head off to the photo shoot,” she commanded. “No time to visit with your Aunt.”

Everything was a rush, but I arrived ten minutes before the photographer, so everything worked out.

That evening I was able to recount my adventure to Aunt Beth and Gloria. It appears that everyone was pleased with me, as Ms. Eames recounted to my Aunt. I was pleased with the money.

Fame can be fleeting, and when I was back at the office the next day, it was back to entering billing records into the computer, but Ms. Eames assured me that there would be more modeling work.

* * *

A few days after my first modeling job, Ms. Eames called me into her office. “I just heard from Jake. He is exceedingly pleased with you as a model. He said that you are not only gorgeous, but you were very cooperative and the photo shoot went smoothly. He also said that the camera loves you, but we already knew that. He is sending over some glossies from the shoot for our records and for your portfolio. When the ads appear, he said he will send copies to me.”

In addition to my work in the office, I was sent out on some modeling jobs. One day, Ms. Eames invited me to attend a fashion show with her. “I have several models here. I want you to see them walk up and down the runway, and to see if you could do the same.” I paid close attention to how they walked and turned and later I practiced in front of my Aunt and Gloria.

When I thought I had it right, I mentioned it to Ms. Eames. I was wearing a nice dress and heels, and Ms. Eames suggested that I show her. There was no runway available, but we used the hall in the office as a substitute. Once or twice I gave a twirl as I turned, lifting my skirt. Ms. Eames liked it and declared that I was ready for fashion shows.

Over the next weeks I did several photo shoots and some runway work, both locally and out of town. I was beginning to get over my nervousness and start to enjoy this work.

However, I was concerned that no one at the Eames Agency knew that I was a transwoman, and if it came out it could cause problems. I had no idea how to tell them, and still keep my office job. I mentioned my concerns to my Aunt and Gloria. They had no unique ideas, and said just tell the truth, and, when you decided to break the news, really glam up.

I finally decided to tell Ms. Eames on the next Friday, and made a special effort with my appearance. I asked her if she had a few minutes, because there was something I wanted to talk with her about.

“I’ve got a problem I’d like to tell you about,” I told her.

“You’re not pregnant, are you?” she asked. I could see that big problems in her opinion were things that would change my appearance and end my modeling career.

“No, nothing like that,” I said. I thought it was humorous that pregnancy was one thing that was impossible for me.

“If you have a problem, let’s find a solution. I’ve got you scheduled for some holiday shows and this is an important time for the agency.” She waited for me to express my problem.

“Ms. Eames. I haven’t been quite as candid with you as I should have been. You see, my name was Jason when I was born. I’m a transwoman, if you know what that is,” I blurted out.

“And you think that is a problem?” she said. “Have you ever heard of Andreja Pejic, Kelly Star or Carmen Carrera to name a few? All of them are top models, and all of them are like you. Being transgendered is not a problem at all, in fact it may be an asset. I may have to increase your hourly rate now that I know. Think about whether you would be comfortable with us making it public, because I think there is a market for it.” She had a huge smile on her face.

“Virginia,” she called out, “Please come in here for a moment. Our little Peggy has just revealed another surprise. She’s a transwoman.”

“Oh, that’s so neat. She looks so beautiful that no one will believe it. We’ve had requests in the past for Transgendered models, and now we can satisfy the demand.”

I went home that afternoon, a very happy girl. A huge weight had been lifted from my shoulders.

Now if I could only resolve the problem with my Dad.

* * *

Since I started living at Aunt Beth’s house, I had tried to visit my parents and sister at least once a week. Because my Dad was uncomfortable at my Aunt’s house, I usually went back to my parents’ place, as Jason. However, over the summer and into the fall my hormone therapy had caused my breasts to grow and my hips and butt to become larger. It was no longer a matter of putting on Jason’s clothes, I now had to bind down my breasts, and I had to get different jeans. Needless to say, I was uncomfortable during my visits.

Emma was disappointed that I couldn’t wear a dress or skirt when I visited, since my cross dressing had begun with her, so she would occasionally visit me at our Aunt’s house. My Aunt would occasionally go with me when I visited my parents, but my Dad made it plain that Gloria was not welcome, and Aunt Beth limited her visits.

On one of my visits, Emma asked me to come up to her room. Once inside, she asked me if I was wearing panties, which, of course, I was. “Let me see,” she said, so I unzipped my jeans and pulled them down. It was then that she noticed that my jeans appeared to be girls’ jeans.

“They just fit better, since I have more fat on my hips and butt,” I explained.

“How about your tits,” she asked.

“Growing,” I replied.

“Can I see?” she asked.

“I have them bound down, so there isn’t much to see,” I replied.

“Then take off the bandage,” she suggested, which I did.

“Oh my,” she said when my tits were free, “they’re getting bigger. Can I touch them?”

“Sure, why not,” I answered. But she did more than just touch, she fondled them. I began to squirm with pleasure, and made soft moans. This just encouraged Emma, and she leaned over and began to suck on my nipple. I could hardly stand it.

“You better stop,” I gasped. When I recovered a bit, I said, “I didn’t know that you went for girls.”

“I usually don’t but I’ve had a few lesbian affairs. Remember Sandra?” I did, especially her large breasts.

“Help me get the girls bound up,” I requested, and handed her the elastic bandage. With her help I got dressed.

A minute later she picked up the style section of the local paper and turned to a page which she had marked. “Anything look familiar?” she asked.

“That’s a picture taken in Forbes Park, here in town,” I said, ignoring the obvious.

“Not the park, silly, the model,” she exclaimed. I did recognize the model, because I was she.

“When did you start modeling?” she asked, and I recounted the story of me and the Eames Agency.

“Does Mom know?” I asked.

“She’s the one who pointed out the ad to me,” Emma replied.

“I’d be willing to bet that she didn’t show it to Dad.” I commented.

“That’s a sure bet,” she commented.

After looking at fashion magazines and making idle conversation, she turned serious.

“I’ve missed your company. When are you and Dad going to come to terms?” she asked.

“They’re his objections, not mine,” I answered. “He has to come to accept me as I am.”

“And how do you propose to get him to do that?” she asked.

“I just don’t know,” I said with a dejected tone in my voice. “Maybe Mom has an idea,” I suggested.

“I’ve asked her, and she doesn’t,” Emma responded.

Aside from Mom asking how I liked my new job, nothing more was said about what I did, or where I did it during the whole dinner. One safe topic was college, and I described my accounting and business courses in detail, which pleased my father, I decided to not mention the gender studies course. Emma had recently landed a job at an auto parts store, which I found hilarious because she hated anything mechanical.

When back at my Aunt’s house, I told her and Gloria that I would like to resolve the issues with my Dad. “Have you suggested counseling?” Gloria asked,

“Mom and I did, but he said counseling was an unnecessary expense. He said that everything could be resolved if I stopped prancing around in a dress like a pansy,” I related.

“What is being done has resulted in no progress,” Aunt Beth observed. “Perhaps we could bring things to a head if I invited everyone to Thanksgiving dinner here. You could wear that nice dark-green cocktail dress you bought.”

“If Dad knew what was up, he would refuse to come, and Mom wouldn’t either, since she wouldn’t want him to be alone on Thanksgiving,” I observed.

“The key here seems to be your Mother,” observed Gloria, “Maybe we could get her to make him to come.”

“Let me talk to her about that,” Aunt Beth said, and things were left at that.

* * *

I had hoped to see Steve over Thanksgiving, but he and his family were visiting some relatives in the next state, and would not be in Dalton at all for the entire weekend. I was visibly unhappy. That night, I saw Gloria open my bedroom door, and felt her slide into bed with me. “Your Aunt asked me to come here to comfort you,” she said.

The next evening Teri or Terrence, I couldn’t tell which, called, and during the course of out conversation I let on how disappointed I was that I could not see Steve during the Thanksgiving weekend. “Hey, I’ve got an idea,” she or he said, “let’s catch a movie this weekend.” Having no better plans, and needing company, I agreed. Only after I hung up the phone did, I realize that I still didn’t know if I was going to be with Teri or Terrence, but in my state of mind, I really didn’t care. It would become obvious when I arrived at his or her house.

On Saturday my mood had only slightly improved, and I thought that if I wore something sexy that I would feel better. I decided to wear nylons and a garter belt, along with a skirt, slip, bra, camisole and blouse. When I arrived at his or her house, I saw the door open and out stepped Teri. She also was wearing a skirt and blouse under her jacket. She slid into the car, leaned over and gave me a kiss. She then put her hand on my thigh, and as we drove I felt it inch up my leg until it was at the top of my stocking. I then felt her finger the garter strap. “Ooh,” she said, “nylons and garters. I’m excited.” When I parked the car at the theater, she took my right hand and put it on her crotch, just to prove that she, in fact, was excited.

The ride home after the movie was a repeat of what had happened before. I was missing Steve, and a little erotic touching was not totally unwelcome. When we arrived at her house, she invited me in. I knew that I should refuse, but I was feeling lonesome, so I went into her house. Once inside, she said that no one else was home, and with that she embraced me and began kissing me. During our kissing, I could feel her hand rubbing my body, and my breasts touching her breast forms. I became excited, and a certain part of my body made that obvious. We took off our jackets and she guided me to the couch, where she sat with her body touching mine. She moved her hand up my skirt. I was so excited I couldn’t get her to stop. What ensued was obvious.

I was too embarrassed to want to discuss the evening with my Aunt or Gloria, so I complained of a headache and went directly to bed.

* * *

During the week before Thanksgiving, my Aunt, Gloria and I spent most of our available time preparing for the dinner. My Aunt had decided on a classic Thanksgiving meal of turkey and the usual. Aside from my Aunt, Gloria and me, and my family, Aunt Beth had invited her brother and his wife, their two children and their spouses, a distant cousin and, surprise of surprises, Ms. Birch.

I wore a dark-green cocktail dress which emphasized the feminine curves which I was developing. My father wore an angry expression; angry that my Mother and Emma had practically forced him to be there, angry at me for the way I looked and acted, angry at Gloria, who he didn’t like, and otherwise just plain angry. Everyone else wore what would be expected, skirts or dresses for the women and coats and ties for the men, all except for Ms. Birch. She couldn’t have looked more ‘butch’ if she tried. The conversation at the table was fairly innocent and everyone was too busy eating and recounting stories of years gone bye. It was after the dinner and when everyone retired to the living room that things heated up. The big argument had my father on one side and Gloria and Ms. Birch on the other. Unfortunately for my father, he was not only double-teamed, but outclassed in the fact department. My Mother, Emma, and I just sat there and watched. The rest of the guests kind of drifted off, the women to the kitchen and the men to the football game on the television. The argument appeared to have two issues. The first, promoted by Gloria and Ms Birch, was ‘are you going to allow your stupid prejudices to cause you to lose a child who loves you deeply.’ The second, promoted by my Dad, was ‘what he’s doing is unnatural, prohibited in the bible, and is really a passing fancy that he could stop any time he wanted to.’

Ms. Birch had the facts to establish that what I was doing was not a passing fancy but was a recognized medical condition, and my Dad lost that point.

Dad pointed out that calling how he felt was ‘stupid’ was uncalled for, and he won this point.

Everyone agreed that I loved my father deeply, and he admitted that he loved me, at which time I jumped out of my chair and went over to give my Dad a big hug. This pleased everyone present.

Gloria backed my father into a corner where he had to admit that his position would eventually mean that he would lose a child who loved him and whom he loved. He said that was not what he meant, but couldn’t get around it. He lost this point.

Ms. Birch challenged my father’s position that being transgendered was ‘unnatural’ and had the historical facts to back up her position that it had been going on since the dawn of humanity. She also brought up that there were people who were intersexed. My father had no facts to counter this point.

The final point was the bible. My Aunt was able to get my father to concede that there were inconsistencies in the bible, and he was so flustered that he couldn’t say where in the bible it said that what I was doing was condemned.

Regardless of what had been argued, the issues all came down to love. Unconditional love between a parent and a child. This was the most important thing. If I loved my Dad, and he loved me, that should be enough to overcome the rest. My father had to concede this, which he did with tears in his eyes. When he started to cry, my whole family gathered around him.

Finally, we all agreed that my father didn’t have to like what I was doing, but that he wouldn’t prevent it or kick me out of the family. This appeared to be a compromise we could all live with.

I wondered how it came that Ms. Birch was included in the Thanksgiving dinner party. I never knew, but I think that Gloria had something to do with it. My Father told me he wanted to change the ‘r’ in her name with a ‘t.’ I had to agree with him on that point. I decided that it would be best, given that a compromise had been reached, to not tell my Dad that Ms. Bitch, I mean Birch, was the instructor for one of my classes.

Finally, we all agreed that I would continue to live at my Aunt’s house, that my Father was always welcome there and that I could dress as I pleased when I visited my parents and sister.

After the argument was over, I was asked about my job. Everyone, including my Father, was impressed that I had the start of a modeling career.

* * *

It was not surprising that Ms. Birch used the substance of the Thanksgiving day battle as a classroom example of how family disputes over a transgendered child might be resolved. What was surprising was that Ms. Birch actually wore a skirt to class one day. Unfortunately, she had ugly legs, and I thought that slacks were a better option for her.

Then came the class projects. As threatened, she said all of the boys had to dress as girls for at least one day, and that they were not allowed to hide in their houses for that day, but had to do what they usually would do but wearing a skirt or dress. This caused great mirth among the girls, and where was no shortage of girls who would help the boys. There was an unsubstantiated rumor that some other boys were to hit on the cross-dressed boys, so they would know what it was like to be hit upon.

My project was a natural. I wrote a paper on sexual stereotypes in the modeling business.

I am pleased to report that I earned an ‘A’ in all of my classes.

Because the issues with my Father had been resolved, I could now dress as a female all day, every day, and start on my Real Life Experience.

* * *

I eagerly awaited Steve’s return home for his Christmas break. One evening I was sharing my excitement with Emma. “So, do you have anything exciting planned for him?” she asked.

“In what way” I responded.

“What way do you think?” she replied, “it should be obvious to you.”

“Oh, that,” I said, “the usual.”

“You know, there are plenty of girls at Steve’s college who are more than willing to go all the way, and he may have found one or more of them. Your ‘usual’ may not be exciting enough.”

“So, what do you suggest?” I asked.

“Talk with Gloria. I bet she has experience with a solution,” Emma answered.

Later that evening, Aunt Beth, Gloria and I were sitting around the kitchen table sipping camomile tea, when I recounted the substance of my conversation with Emma.

“I assume that you want to keep Steve interested in you, with something new and different,” my Aunt said.

“There is something you can do, but it might gross you out and you might not like the idea,” Gloria observed.

“Why?” I asked.

“Because it involves your butt,” she answered.

“Oh,” I said, getting the general drift.

“Have you . . .” I started to say.

“Yes,” Gloria replied, knowing what my question was.

“And so have I,” my Aunt interrupted.

“If you’re interested in taking this further, just let me know,” Gloria said.

When I was in bed, I saw my bedroom door open. It was Gloria, and she climbed into bed with me. “Your Aunt suggested I come here,” Gloria said, “she thinks you should try it.”

She produced a jar of lubricant and a small device, which she proceeded to use on my behind. At first it hurt, but later on it was pleasurable. I had learned something new.

When Steve and I went out on a date, I afterwards brought him to my Aunt’s house, and used my new found knowledge. Steve loved it.

* * *

Right after the first of the year, Steve returned to college and things got really busy at the Eames Agency. I did a lot of photo shoots for local businesses, and even a few out of town fashion shows. It wasn’t easy to balance school and work, but I did the best I could.

One of my New Year resolutions was to get a name change and change my name and gender marker on my driver’s license, after which I could work on getting an amended birth certificate. The first step was to legally change my name to Margaret Cleary. To do this, I obtained and filled out the necessary forms, and filed them with the court, after which I arranged for publication of my intent to change my name. I also obtained a court date for the hearing on my name change.

On the day of the hearing I wore a charcoal suit with a pencil skirt, which came down to just above my knees. I also wore an ivory long sleeved blouse with, charcoal pantyhose and heels.

There was a list by the courtroom door of the cases being heard that day, and I located my case. At last, my matter was called. The judge studied the papers which the clerk handed him, after which he asked about my financial status and if there were any criminal charges pending.

“Mr. Cleary, you want to change your name to Margaret Cleary from Jason Cleary? Tell me why,” the judge then asked.

“I’m a professional model, and the name Jason doesn’t quite match what I’m doing,” I answered.

“Okay, name change granted,” he ordered, “Have your order stamped by the clerk.” After having multiple copies of the order stamped, I left the courtroom. That was it.

Now that my name was legally changed, I could amend my drivers’ license. The name change order was necessary to change the name on my license, but to change the gender marker required a letter or affidavit from someone in the medical or mental health field, including my physician, LCSW, MSW, RN, or PA, certifying that I was taking appropriate clinical steps to change my gender. Having these, I went to appropriate office and had my drivers’ license amended.

I was now in my sixth month of Real Life Experience, and my counselor was pleased with my progress. “You are halfway there, Margaret,” she said, “have you figured out how you will finance your surgery?”

“I have health insurance, but I’m not sure how much of the procedure is covered. Luckily I am well compensated for my modeling, and I have a tidy sum put away. When I have enough between insurance and available funds, I can go forward.”

While I was waiting for the time to pass before I could have my reassignment surgery, I decided to have breast enhancement surgery, which meant, after it was done, that a lot of my clothes no longer fit me, but on the other hand, I now had really nice cleavage. I went shopping to replace the part of my wardrobe which no longer fit with clothes that emphasized my new shape and cleavage. All in all, I was very pleased.

When I went to the next gender society meeting, Teri was more than casually interested in my new figure, and made it plain that she would like to spend more time with me, an invitation which I gently declined.

With the approval of my counselors and medical people, I scheduled my surgery for the next spring. Ms. Eames understood why I was doing this, but moaned that she would lose the services of one of her models during my recovery. “There is a compensating factor,” I told her, “I can then model string bikinis.” This brought a smile to her face.

Gloria graciously volunteered to accompany me to my surgery. I would have liked to have Steve there, but that just wouldn’t work. As a compensation, I decided that he would be the first to try out the new me. I loved Steve and wanted to marry him, but his parented were dead set against me and what I was doing. The even threatened to cut off his college funding if he thought of marrying me. One of the reasons they expressed was that I could not have children. I pointed out that in any marriage there was no guaranty of children, but they were not dissuaded. The idea of adopting children was, in their opinion, not an acceptable alternative. What Steve wanted was only a very minor consideration.

Steve and I discussed eloping after he finished his education, but that was years away. If I could be sure of a career in modeling, I might be able to pay for Steve’s education, but no conclusion was reached. In any event, Steve did not have the fortitude to try anything that would challenge his parents. While we continued to date, I was not welcome in Steve’s house, and treated very coldly when in his parents’ presence. Gloria’s prior advice to me rang in my mind: ‘One thing I’ve learned is to consider my feelings first, and not let another person control my life.’ Steve obviously didn’t agree with this. In any event, the whole point became moot when Steve became engaged to some air head bimbo he met in college. The irony of it all was that she proved that she could bear children, because she did just that without the benefit of being married. As a result, Steve had to drop out of college and get a job to support his family.

Oh well, you can’t win them all.

It Started On A Rainy Afternoon - Part 4 - Conclusion

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Final Chapter

Genre: 

  • Transgender

Character Age: 

  • College / Twenties

TG Themes: 

  • Voluntary

Other Keywords: 

  • Modeling

Permission: 

  • Posted by author(s)

It Started On A Rainy Afternoon - Part 4 - Conclusion
By Pentatonic

Steve’s breaking up with me was an emotional disaster. Luckily I had my family. My Dad even let me cry on his shoulder while I was wearing this smashing looking dress. “My dear,” he said, “you have us, and believe me, this is not the end of the world, even if it seems that way to you. While I now know how wrong Steve’s parents are, it appears that he will not stand up to them like you did to me. Most important, we all love you.”

He handed me a tissue to wipe away my tears. “By the way, that’s a very pretty dress, and you don’t want to get tear stains on it,” he said with a smile.

I was fortunate that he, unlike many of my acquaintances, didn’t point out that there were lots of available guys out there. Both he and I knew it, but at that time all I needed to hear about was love.

Mom was Mom. I knew that I had her love. Likewise, Aunt Beth’s love was supporting. Emma had a more practical approach. She was trying to figure out who might be a good boyfriend for me. “Look,” she said, “you’ve got it all. You’re smart and very good looking. The only problem is that you’re a model and have money. Some guys can’t deal with that; it intimidates them,”

I poured myself in my school work and modeling to distract me from my grief. My career as a model had taken off, and I rarely had time to engage in self pity.

Then I met Charlie. It is true that the best way to meet a new boyfriend is at school. I met Charlie in the accounting class. Like me, he was a part time student and could not afford to go away to college. He had a part time job as a book keeper and lived at home with his parents.

One day, right after accounting class, he caught up with me. “Hi,” he said, “my name is Charlie. I don’t mean to be forward, but you seem to know your stuff, and I thought we could study together for next week’s test.” He smiled, and when did he had the cutest dimples in his cheeks. Unlike most of the other students, he was nicely dressed, he wore a sport coat, a white shirt with a matching tie, tan slacks and brown loafers. I was impressed.

“You always dress so nicely, I figured that you have a part time job like me,” he volunteered.

“True,” I responded.

“So, where to you work?” he wanted to know.

“I work at the Eames Agency. It’s a modeling agency.”

“Wow,” he exclaimed, “do you do book keeping?”

“Part of the time,” I answered. I was beginning to like him, so I didn’t want to tell him that I was also a model and scare him away. However, I thought, if we get together he would find out anyway, so I told him. “The rest of my time I’m a model for women’s fashions.” There, it was out.

“You mean, like walking down a runway?” he asked.

“Some of that, the rest are photo shoots,” I answered, “now for your original question, when and where do you want to study?”

“How about my house, on Thursday afternoon, about 3:00?” he said, and he wrote down his address.

“I have a photo shoot that day, but I should be finished in time. Let me have your number if the photo shoot runs late. Let me give you my card,” It was my Eames Agency card, with “Margaret” in bold letters on it. I added my cell phone number to it.

“I’m impressed,” he said when he looked at the card. “Well, I’d like to talk more, but I’ve got to get to my job,” he said.

“See you on Thursday,” I responded, as we went our separate ways.

The photo shoot ran a little late so I left for Charlie’s house without changing my makeup. When I arrived at Charlie’s house, a middle-aged woman answered the door, who I assumed was Charlie’s Mother. I could see that she was taken aback because I looked like a fashion plate. “Hi, I’m Margaret and I’m here to study with Charlie,” I said as a greeting.

For a few seconds she just looked at me. She then found her voice, “Charlie said that a fashion model was coming to study with him. I thought he was exaggerating, but it seems to be true. Please come in. Charlie’s in the den. Let me show you the way. Would you like something? I was about to start a pot of tea.”

“Tea would be most welcome,” I said, flashing her my best camera smile.

When she came in with the tea, she was carrying a part of a newspaper. “I don’t want to interrupt, but I have a quick question,” she said as she opened the Style section of the paper. I knew what was coming. She pointed out an ad for a local dress shop. “That’s you, isn’t it?” she asked.

“Yes,” I answered.

“Will you autograph it for me?” she asked, which I did. She was thrilled.

About 5:30 Charlie’s Dad came home. Charlie’s mother spoke to him in hushed tones, but I could make out the words ‘fashion model’ and ‘in one of Charlie’s classes.’ Charlie and I had just finished a problem involving accelerated depreciation, and when he heard his father’s voice, he called out, “Come into the den, Dad, there’s someone I want you to meet.”

Charlie’s Dad was a good-looking man, and when he smiled I could see from where Charlie got his dimples. “Dad, this is Margaret. She in my class, and we were studying for an exam.”

“I’m not interrupting your studying, am I?” he asked.

“No, we’re finished,” Charlie responded. The four of us sat down and chatted until it was time for me to leave.

Both Charlie and I got an ‘A’ on the exam, and flushed with success we continued to study together, sometimes at his house, and sometimes at my Aunt’s. Gloria was really positively impressed with Charlie. “If he doesn’t ask you out for a date, you’ve got to,” was her sage advice. “If you want to,” Gloria suggested, “you could bring him here, and your Aunt and I could make ourselves scarce while you worked your feminine wiles on him.” I detected a salacious grin on her face.

Charlie did ask me out for a date, and thereafter we sat next to each other in class, two well dressed and employed students among the unemployed slobs.

Even though I had a new boyfriend, I still missed Steve.

* * *

A major advantage of having a boyfriend was that it deterred some unwanted advances. However, this did not deter Teri. “You haven’t told him, have you?” she accused. I admitted that I hadn’t.

“Well, if you have unfulfilled sexual urges, just call me,” she said. I didn’t think that was a good idea, and I just mumbled a vague reply.

Teri was really all tarted up at the next gender society meeting. She wore a short tight skirt that emphasized her lack of hips, way too much makeup and a tight top. One could see that she was wearing a garter belt and hose, not pantyhose. On her feet were skyscraper heels. One member sarcastically asked her if she was going into a new line of business, and if so, at what street corner was she plying her trade. Teri just glared in response. It turns out that her display was aimed at only one person, me. Since Gloria was not there, Teri hovered close to me the entire evening, touching me a lot, especially on my butt. She rubbed her shoulder against my breasts, attempting to excite me. She ignored any hints to leave me alone. To crown everything off, she asked me for a ride home.

On the way to get to my car, she put her arm around my waist and pulled me tight to her, When I glanced down I could see a bulge in her tight skirt. She was aroused. I was nonplused and didn’t even open her door for her, When we were both in, she leaned over the console and took my head in both hands and kissed me. I could feel her tongue pushing against my lips but I did not open them. She then put one hand behind my head and began rubbing my breast with the other. All the way to her house, she kept a hand up my dress, rubbing and moving closer to my groin. Since I was driving, I couldn’t fend her off that well. When we arrived at her house, I insisted that she get out and I quickly drove away.

When I arrived at my Aunt’s I complained about the evening, and how frustrated I was. Gloria suggested that I take this problem to my new boyfriend, which, at that moment, did not take care of my frustration.

* * *

Charlie was very interested in my modeling, and how the business worked. I wanted to take him with me on a shoot, for Coulters, a local department store, and I asked Ms. Eames if that was okay. “It’s fine with me, but you have to ask the photographer who is directing this shoot,” she said. “Hey, I have an idea. Have him sign our standard contract, and then you can truthfully say he is a model in training,” she continued. She called out to Virginia, “Can you print out a sheet of business cards with the name ‘Charlie’?”

Armed with his business cards, Charlie and I went to the photo shoot. I introduced Charlie as a model in training, and Charlie gave the photographer a business card. The photographer had no problem with Charlie being along. “Just stay out of the way,” he said.

Shortly after the shoot started, the photographer and the male model got into a terrible fight, and the model left in a snit. The photographer was really angry because the shoot could not proceed without a male model. Then he looked at Charlie. “Hey, you, model in training,” he said, “What agency?”

“Eames,” I quickly answered for him, “Same as I.”

“What rate?”

“Lowest,” I said, and quoted the amount.

“Give him a big smile,” I whispered to Charlie, which he did, exposing those cute dimples of his.

The photographer saw them. “Hey, you, errr . . . dimples, I didn’t get your name,” he said. He then said, ‘but that doesn’t matter. I have your card here, somewhere. What are your sizes?

Charlie rattled off his height, weight, shirt size, coat size, and inseam.

The photographer turned to the store representative. “Do you have any clothes his size?” he asked.

“Close enough to make it work,” the representative answered.

“Then let’s get to work, people,” the photographer announced.

“One thing,” the store representative said to the photographer, “I’ll let you deal with that other idiot model that you hired. We aren’t going to pay a cent for him, even if we pay a lot less for Dimples.”

The shoot proceeded as planned. Charlie did a wonderful job, paying close attention to what the photographer told him to do. The photographer printed out some digital copies, and shared them with the store representative. “The camera loves him, just like it loves Margaret. See what great talent I can supply on a moment’s notice,” the photographer bragged.

“You didn’t find him, Margaret did,” the representative said. “I’ll bet that Eames is going to love this. You might want to put Eames on your speed dial.”

“Does he get one set of clothes that he modeled?” I asked.

“Sure,” said the representative. “Have him pick out what he likes, and Dimples, when someone compliments you on your clothes, make sure you tell him or her that they came from Coulters.”

When we returned to the agency, I related what had happened, including Charlie’s nickname of Dimples. “Thank God that we didn’t supply the idiot who walked out, and having Charlie was a stroke of good luck,” Ms. Eames said. “We should have some digital copies from the shoot in a few minutes. In the meantime, take Charlie to Joe for some head shots. I want to start making up a portfolio for him.”

When we returned to Charlie’s house, his Mother was overjoyed with the news and hugged both of us.

* * *

Charlie mentioned to me that a friend of his was throwing a Halloween party. “It’s costume,” he said. There was a temporary costume store at a local mall, and we decided to see if we could find costumes before accepting the invitation. I immediately found a witch’s costume. Then Charlie noticed a sign that said, ‘Plus sizes.’ Displayed was a plus sized snow white costume. I found one that might fit Charlie. “Take off your shirt, and slip it over your head, and we’ll see if it fits,” I said. He did, and it fit. We also bought a cheap bra.

We then found a cheap wig and a few accessories, and purchased them. On the way to his house, I asked him, “It doesn’t bother you wearing a dress, does it?”

“It’s only Halloween, so no,” he replied.

We showed his Mother the costumes, and I noticed a concerned look on his Mother’s face when she saw the Snow White costume. However, she soon got into the spirit of things, as we tried on our costumes. “What do I wear under this?” Charlie asked.

“I think that your usual underwear, and a pair of shorts,” I volunteered, “and a pair of loafers. The dress is long enough so no one will notice, and if they do, that’s just the way it is.”

Suitably costumed, we arrived at the party. Fred, the host, let out a hoot when he saw Charlie. “Do you like wearing dresses?” he asked with an evil smile on his face.

I answered for Charlie, “If he does, it would be humiliating for him to admit it, otherwise he would just be insulted.”

Fred looked a little crestfallen with my statement, “Sorry, it was just a joke,” he said, “but you have to say he looks good, but not as good as you. This was said as he was staring at my breasts,

We had a good time at the party, and I liked dancing with Charlie. On the way home, he said, “You really put Fred in his place, do you know what my answer would have been?”

“Only if you are comfortable telling me,” I answered.

“I do like wearing dresses,” he admitted, “I hope you don’t hate me for saying this.”

“I don’t hate you, and I like you even the more for being able to admit it.” With that, I pulled the car over to the curb leaned over the console and kissed him. Now I understood why his mother had looked concerned.

* * *

One day after class, I mentioned that I wanted to go to the mall to pick up a few things, and asked Charlie if he wanted to go along. “I don’t have to work today,” he replied, “so why not? I could use a new pair of slacks, so why don’t we go to Coulters and use some of the money from the photo shoot.”

When we arrived in the mens’ wear department, there were large posters in stands with Charlie. We stood close to one and admired it. This caught the attention of one of the clerks. “Can I help you?” she said.

“Do you have those slacks in slate?” Charlie asked.

The clerk did a double take. She looked at the poster and at Charlie. “Give her a smile,” I whispered, which he did, exposing those dimples.

The clerk made the connection. “That’s you, isn’t it?” she asked.

“Yes,” Charlie replied.

“Could you wait here for a minute?” she asked, and she went over to the cash register area and picked up a telephone. When she came back to us she said, “You know, I thought that you models only bought clothes at high end stores, but here you are buying clothes at Coulters. Let me show you some other clothes you might like.” While she was doing this, a well dressed man came over to us.

“I’m Mr. Sloan, the store manager,” he said, “and that’s you in the poster.”

“It is,” Charlie affirmed.

“Could you autograph the poster, and would you let us take pictures in front of the poster and buying clothes? The photos would be used for our store newsletter,” he said. “I’ll call your agency, and take care of any financial arrangements.”

A few minutes later a photographer arrived and started taking pictures. Mr. Sloan then turned to Charlie and asked, “Can I ask you why you decided to shop here?”

“I buy most of my clothes here,” Charlie responded, “and I thought it only fair to spend the money I earned at the photo shoot here.” Mr. Sloan beamed.

Mr. Sloan then turned to me. “You’re a model also, aren’t you? I thought I saw your posters in the womens’ department.”

“Yes,” I replied, “and like Charlie, I buy a lot of my clothes here.”

One last photo showed Charlie paying for his purchases. “I want everyone to know that you actually bought clothes here,” Mr. Sloan explained.

“Could you sent copies of the photos to my agency, Eames, along with a copy of the store newsletter?”

“It would be my pleasure,” he responded. The photo taking had drawn the attention of other shoppers, and we soon had a crowd. Mr. Sloan announced that the models for the store shopped at Coulters. Charlie and I flashed smiles.

When I returned to work, I explained to Ms. Eames what had happened at the store. “I told Mr. Sloan that we would give him a special rate, provided that he told all photographers that did the store’s work that the store wanted Eames to be the sole agency for their work.”

* * *

It was a rainy afternoon in November when Charlie and I were studying at his house. His Mother was away for the whole afternoon, and we had the house to ourselves. “I thought about what you said, and I wonder if you want to show me what you look like in a dress,” I said.

“Are you sure?” he said.

“Yes,” I answered, and then I asked, “provided you have any dresses or skirts here.” With that he led me to his closet, where he had a feminine wardrobe in the back. After seeing this, I added, “I therefore assume that you have the necessary underclothes.”

“Bottom drawer of my dresser,” he replied. With that he started to undress. When he was down to his undershorts, he stopped. “Hand me a pair of panties, and I’ll go into the bathroom to change.”

He made a nice looking college aged girl, with cute dimples. I just had to kiss him, and then one thing led to another. However, I had to hide my ‘secret’ from him,

* * *

One evening I casually mentioned to Gloria and my Aunt that Charlie was a cross dresser, and related how I had found out and what I had done. “And, let me guess,” Gloria said, “you just forgot to tell him about you.”

“Well . . . yes,” I admitted.

“If you want the relationship to continue, you have to tell him,” my Aunt declared. “Why don’t you invite him over here for Sunday Dinner?”

After dinner that Sunday, I said, “Charlie, you have been forthright with me, and I appreciate it. I really want our relationship to continue, but there is something about me that you need to know.”

He waited for me to continue. Well, here it goes, I thought. “You know what transgendered means, don’t you?” He nodded his head. “Well, I’m a transwoman. I was born male. I am in transition and will have my surgery this spring.”

He looked surprised, but not shocked. “Does that mean that you have a . . . er . . .”

“Yes,” I answered.

His next statement surprised me. “Could I see? After all you made me show you mine,” he said.

“Not at the dinner table,” interjected my Aunt. “Let’s go upstairs,” she then added as if it were agreed that I would strip. Well, I guess it was agreed, because I had no problem with it. The only problem was that my Aunt and Gloria wanted to watch. “Let’s use my bedroom,” my Aunt suggested.

When we were all in the bedroom, I began to disrobe. Actually it was more or less a striptease. It caused an obvious reaction with Charlie, “Why don’t you also undress, Charlie?” my Aunt suggested, and he began to disrobe. Finally, both Charlie and I were naked, and fully aroused. “You take care of him,” Gloria said to me, “and I’ll take care of you.”

“Let me,” Charlie said, “I’ve always wanted to know what it is like.” And so that was what happened.

* * *

After that, Charlie became my best female friend as well as my boy friend, and with Charlie as Charlene we went shopping and doing other kinds of girl friend things. One very interesting thing was that Charlene and I were hit on by boys at the mall. It was a new thing for Charlene, but she handled it well.

Charlie told his parents that he had told me that he cross dressed, and his parents were happy that I did not object. Thereafter, there were many occasions where Charlene dressed when I visited her home.

I realized that I was falling in love with Charlie, and he with me.

* * *

Coulters was putting on a show of new bridal gowns in the store, and they specifically requested that Charlie and I be models. Charlie wore a tux, and I modeled bridal gowns. If only this was for real, I thought.

* * *
Over the holidays, I had a brief but intimate talk with Charlie. “You like to cross dress,” I started out to say, “and that is perfectly okay with me. What I want to know is whether you want to transition and become a transwoman.”

“I don’t,” he replied, “but why do you ask?”

“Because I love you and want to marry you after my surgery,” I blurted out.

“Aren’t I the one who is supposed to propose?” he asked with a grin.

“Okay,” I answered, “so what are you waiting for?”

He then got down on his knees. “Will you marry me?” he proposed.

“Yes, on one condition, I’m the only one wearing a wedding dress at our wedding,”

* * *

Epilog.

I had my surgery and Charlie and I were married. This brings me to today’s date. It is a rainy afternoon, and my husband and I are entwined together on our bed.

The End

Plus Sizes

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Sweet / Sentimental

TG Elements: 

  • Slice of Life

Other Keywords: 

  • Hairy Back Large Person

Permission: 

  • Posted by author(s)

PLUS SIZES
By Pentatonic

Inspired by a comment submitted by TMI Fairy on Wed, 2017/06/28 - 11:57pm:
“Are there fics where the T-girl starts out at 6'3 and 250 lbs? With big feet and a hairy back?”

Hugh stared out the kitchen window. It was raining. “No field work today,” he said to himself, and he poured himself another cup of coffee. He farmed a piece of land, about 320 acres. Corn and beans. Crops he could sell. He also had a good sized vegetable garden, and raised a good variety of produce which he could sell at the local farmer’s market. Rain meant inside work. He had completed repairs and maintenance of his agricultural machines, so no work in the barn.

Hugh was a big man. He stood 6' 3" and weighed 230 pounds. He wasn’t particularly fat, just big, especially his behind.. He lived by himself in a small farm house, well off the section line road. No spouse, no children. He turned from the window and carried his coffee into the bedroom, and looked at his fingernails. His hands were well cared for, unlike many farmers. His fingernails were well manicured and trimmed. But there was a further difference; they were painted a subdued coral color.

He sat down and removed his work boots and woolen socks. He then stood and took off his flannel work shirt and t-shirt. He loosened his belt and his jeans dropped to the floor, revealing a pair of sky blue panties. He picked up his jeans and put them on the bed, along with his other clothes. He reached into his panties and pushed his privates between his legs to rid himself of the bulge in front. He then went to his dresser and picked out a large bra, also sky blue. From another drawer he took out a pair of breast forms, With practiced ease he fastened the bra behind his back and slipped the brest forms into the cups. He was glad that he had used the hair remover creme the day before, so there was no hair on his back.

Hugh had to admit to himself that he wished that he had been born a girl. That was probably the primary reason he had never married, even though he had a lot of opportunities.

He turned around and looked at himself in the mirror, frowning slightly. “Why couldn’t I be petite, like a hundred pounds lighter and seven inches shorter,” he said to himself. With a sigh, he turned to the closet, and took out a chemise marked 24W, which he slid over his head and let it drape down to his legs. No need for hose today, he thought, and removed a similarly sized housedress from its hanger. He slid it over his head and bent over to pick up a pair of rather large sandals with one inch heels, all he thought he could get away with, being so tall.

He sat down at a low table with a mirror behind it, his version of a vanity. He picked up a hair brush and brushed it until it resembled a pixie cut. Maybe not the best for a large person, but it had to do. Lastly, he put on some red lipstick. Full makeup can wait for another day, he thought.

He stood up and walked to the full length mirror mounted on the back of the bedroom door. He gave himself a critical look. Not really good enough to go outside but not terrible. A pretty good job, considering what he had to work with, he thought.

Just then, the door bell rang. Hugh looked out and saw Ralph’s pickup in the driveway. Ralph farmed the other 320 acres of the section, and had been his closest friend for many years, Thankfully, Ralph knew about Hugh’s “hobby.” Hugh pranced to the front door on his heels, and opened it with a flourish.

“Oh, I see it’s Natalie today,” Ralph said as he walked in. “All dressed up, and nowhere to go,” he added.

“Hardly,” Natalie replied. “Don’t you know that this is a house dress,” she said, holding out the hem. “House dress, as in wear in the house. Not for going out.”

“Whatever,” Ralph replied. “Hey, I’ve got a favor to ask of you.”

“Well?” she said, waiting to hear what the favor was.

“My sister is coming in for a few days, with her kids. While she’s here, she wants me to go with her to visit her aunt for a day. Could you watch her kids and Amy?” Amy was Ralph’s 7 year old daughter.

“As Hugh or as Natalie,” she asked.

“I’m okay with Natalie, and I think that sis is too, so it’s your call.”

“Oh, I don’t think I have anything to wear,” exclaimed Natalie.

“Sheeesh,” Ralph responded. “Put a dress on him and he starts acting like a dizzy blond broad,” he added, with a smile.

Natalie gave him a dirty look. “When is this happening?” she added.

“Next Monday,” was his reply.

“Okay. I think that I’ll wear a full length skirt with a peasant blouse.” she said.

“Whatever,” Ralph replied. He wasn’t that interested in what women wore.

Natalie really liked Ralph’s daughter Amy. Ralph’s wife had passed away a few years ago, and Natalie was able to practice mothering skills on her. The only thing that Ralph noticed was that Amy really liked to be with Natalie. “Make sure that Amy doesn’t tell her cousins that my real name is Hugh.”

Natalie asked Ralph if he wanted a cup of coffee, and he accepted the offer. “I’ve got a beef stew on the stove, and a fresh apple pie for dessert. Why don’t you get Amy and join me for dinner. There’s plenty of food.”

After dinner, they walked into the living room. Natalie’s sewing machine was open and there were patterns and fabric on a table. “What are you making, Aunt Natalie?” Amy asked. Amy had been calling Natalie ‘Aunt Natalie’ for a year or so.

“A nylon blouse with big sleeves,” responded Natalie. “Do you want to see the picture on the pattern envelope?”

“Please,” Amy responded, and Natalie showed her the picture. “Some of my friends’ mommies make clothes for them,” Amy continued. “Would you make some clothes or me?”

“I’d love to. What do you want?” Natalie said as she pulled out a pattern catalog. Does this mean whe wants me for a mommy? Natalie wondered and she smiled at Amy

Ralph just stood there, watching Amy and Natalie. “I really miss my wife,” he said softly, but just loud enough for Amy and Natalie to hear. Natalie could see tears starting in his eyes. She moved closer to Ralph and gave him a hug. He didn’t turn away, but rather he hugged Natalie back.

Suddenly she felt a desire to kiss Ralph, a man. This had never happened before; not as Natalie, and certainly not as Hugh. As she continued to hug Ralph, the feeling didn’t go away; it seemed to grow. Maybe a little peck would be okay, she reasoned, and she kissed Ralph on the cheek.

When he released her from the hug she noticed a smear of her lipstick on his cheek. Something else new for her. “You’d better wipe your cheek, before someone notices,” she said. He just smiled at her.

It was a few weeks later that Ralph again dropped by. It was Natalie who answered the door, wearing a maxi skirt and a cream colored blouse with big sleeves. In fact, it was the blouse which Natalie had been making when Amy asked her about it. “Good, I’m glad that you’re Natalie today,” Ralph said.

“Any reason why?” she asked.

“Well, when Amy and I were here a few weeks ago, you gave me a kiss on my cheek,” he started.

“I hope that you’re not mad about that,” she interrupted.

“No, it’s just when Amy and I got home, Amy asked me why I didn’t kiss you back.” he continued. “I’d like to change that,” and he pulled Natalie into his arms and gave her a solid kiss on the lips. This made Natalie all tingly inside, a new sensation, and she kissed him back.

“I know it isn’t right, but somehow I feel that I’m falling in love with you,” Natalie said softly.

“I know that I’m falling in love with you,” Ralph replied, “so it’s got to be right. Anyway, Amy approves, because she asked me why didn’t I ask Natalie to marry me, and be her new mommy.”

“Would you marry me?” he finally said. “You will have to be Natalie all the time if you do.”

“Yes,” she said, “I’d love that,” and they kissed again.

The next day Natalie ordered a pattern for a bridal gown, size 24W. It required a LOT of fabric.

Roy And The Road To Renee

Author: 

  • Pentatonic

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

Roy And The Road To Renee


By Pentatonic

Roy And The Road To Renee - Chapter 1

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 1.
By Pentatonic

Tuesday, September 2, 2014:

The day after Labor Day; the end of summer and the beginning of another school year,.

When I turned 16 the prior spring I was only 5' 9" tall and weighed about 135 pounds, with way too much of me in my behind, so much that I had grown weary of my friends commenting that my butt would look good on a girl. Although my behind was large, my waist was small compared with it. Otherwise I was just a normal teenager.

I’m not “cool,” to put it bluntly. Although far from the top of the social strata in school, I do have friends. Friends who are nerdy. Some are overweight, and some with complection problems. None of us are athletes. We are just invisible to the cool kids. We are never invited to any of their parties, and we only heard, third hand, of what goes on at such doings.

But even being a nerd, I had a respectable grade point average. I am interested in cars, and have become a relatively competent mechanic. My group of friends and I share an interest in computer games. All in all, we have become used to our social status, and it is not an unhappy situation. Was it the same for girls, I had wondered from time to time.

Over the years I had developed an acquaintance with Becky Jones, who is about 5' 7" and like me could to stand to lose a few pounds. She would make a great valkyrie in a Wagnerian opera. We share many of the same classes in school and sometimes we study together.

Saturday, September 13, 2014:

My story starts on a Saturday afternoon in the middle of September of my junior year in high school. My friends, Joe, Harry, Bob and I were sprawled on the furniture in Bob’s den, half watching something idiotic on the television.

“Hey guys,” announced Joe, “the Homecoming Dance is four weeks away. Are any of you guys going?”

“If it means getting a date, the answer is ‘no.’ It seems like every time I ask a girl out, I get shot down,” answered Harry.

Bob just belched in response and shook his head.

“How about you, Roy?” asked Joe. “You seem to get along with Becky, and she might go with you if you ask her.”

“I donno,” I replied.

At that point Bob’s mother came into the room. “Why don’t you guys see if you can get dates. It may do you good,” she said. “I’ll bet that there are a lot of girls in your school would love to be asked out to the dance.”

“Yeah, but they aren’t the popular girls,”complained Bob.

“Like you four are the most popular guys,” she replied sarcastically.

Monday, September 15, 2014:

What had been said stuck in my mind for the rest of the weekend, and I practiced all sorts of suave ways to ask Becky for a date. At lunch on Monday I came over to the table where Becky was sitting with some of her friends. I approached he table.

“Uh, Becky, do you have a minute? There’s something I want to ask you.” So much for being suave.

“Ask away,” she responded.

“In private.” I said.

“These are my friends,” she said, “I don’t have any secrets from them.” All of her friends were staring at me like a bunch of lionesses looking at a fresh kill.

“Uh,” I continued, “there’s this homecoming dance coming up. I wonder if you’d like to go with me?”

“Like on a date?” she said. The other girls just snickered. I was about ready to run away as fast as I could.

“Uh,” I stammered, “yeah, I guess so. Let me know.” With that I made my exit as quickly as possible. I could hear Becky and the other girls giggling. I could feel my face burning.

The guys had heard the exchange and clustered around me. “So you asked her,” said Joe, “What’d she say?”

“I donno, I didn’t wait for an answer.”

I didn’t have to. After my last class, I was getting ready to go home when one of the guys on the football team came up to me. I don’t think that I ever exchanged more that five words with him in my whole time at school. “I heard that you have a date for the homecoming dance,” he said, “it’s about time that you nerds participated in some school activities and supported the football team. I look forward to seeing you there.” It almost sounded like a threat.

As I was heading to my car in the parking lot, I saw Becky standing next to it. She looked concerned. My first thought was that she was going to reject my invitation to the dance.

“Were you serious about asking me to the dance?” she asked.

“Uh, yeah,” I replied.

“Good, because you didn’t wait for my answer at lunch. You took off like a scared rabbit. I was afraid that your friends had put you up to it for a dare.”

“So what is your answer?”

“Yes, I’d love to,” she said with a huge smile.

“You want a ride home?” I asked, gesturing at the junkyard reject which doubled as my car.

“Ok,” she said. At that time I remembered that gentlemen open car doors for ladies, and I opened the door with a flourish.

I have a sister, Amy, who is a year older than I am and is a senior. Once everyone was seated at the supper table she announced, “Guess who has a date for the homecoming dance.”

“That’s wonderful, honey, who is he?” asked my mother.

“Not me,” she said, “him,” and she pointed her thumb at me.

“Roy, you have a date?” my father asked. “Who?”

“Becky.”

“That’s great.” my mother said. My sister just snickered.

Tuesday, September 16, 2014:

The next day I sat down for lunch with my friends. “So, you really asked Becky out?” Bob asked, “You going to go through with it?”

“Yeah,” I replied, “it ought to be fun. You guys should ask some girl out.”

“Maybe Becky has some friends who would go out with me?” Harry asked. “Could you find out?”

Wednesday, September 17, 2014:

Becky and I are in the same advanced trig course, and there was a test coming up on Friday. “You want to study together?” I asked her.

“Sure,” she said, “I’ll ask my mom, and maybe you can come over after school and stay for supper.” That was the first time a study session had included supper. Something had changed between Becky and me.

At supper that night I told my parents that I would be studying for the test with Becky, and I had been invited to stay for dinner. “Ohh! A study date,” my sister chimed in. I just frowned back at her.

Thursday, September 18, 2014:

On Thursday, Becky and I studied all afternoon. Around six, Becky’s mother announced that dinner was ready.

It seemed as if something had changed. I couldn’t put my finger on it, but Becky’s parents treated me differently, almost as if they were eying me up as possible son-in-law material.

After dinner, Becky walked me to the door. Before I walked out, I asked her if she wanted to go out for a movie and pizza on Friday night.

Becky turned slightly and called out to her parents, “Is it okay if Roy and I go out for a movie and pizza tomorrow night?” Becky’s parents apparently thought it was a great idea.

Friday, September 19, 2014:

At lunch on Friday, Harry asked me if I wanted to go to the game arcade that evening. “No, I have other plans,” I said.

“Like what?” Joe asked.

“Becky and I are going to a movie and pizza,” I admitted. This caused some mirth among my friends and Harry began to hum a few bars of the Wedding March from Lohengrin. I just scowled at them.

Most of the times when I leave the house, my parents are indifferent as to what I look like, as long as it does not violate any decency laws. This time it was different; my mother had me stand inspection. “You can’t go out on a date looking like a bum,” she said, “it’s disrespectful to the girl.”

“You have enough money?” asked my father, “Remember, on a date the guy pays for everything.” I held out my hand and my father put some bills into it. A teenager learns that you never refuse an offer of money from a parent.

I arrived at Becky’s house and her mother answered the door. “Come in,” she said, smiling broadly, “Becky will be ready in a minute.”

True to her mother’s word, Becky came down the stairs a minute later. I had never seen her look so nice. She was wearing a maroon full skirt with a white blouse which was not tucked into her waistband. She wore sandals with a low heel. The most striking part was her face; she just glowed. Her makeup was subdued and her hair framed her face.

“Try to be home at a reasonable time,” her father said with a smile.

Becky and I were about ready to turn to the door when her mother said, “Wait, before you go, I want a picture,” and she began snapping away with the camera on her cell phone.

As we walked to my car, Becky took my hand in hers. It was like electricity. Once we were in the car, she repeated the gesture.

I shouldn’t have told my pals which movie we were going to see, because there they were, with big foolish grins on their faces. I tried to take my hand from Becky’s but she just held on tighter and smiled at them.

Once in the theater, Becky steered me up to the last row, so there was no one behind us, all the time holding my hand in hers.

I could feel Becky leaning against me, and I put my arm around her shoulders. In response, she snuggled closer to me and leaned her head on my shoulder. I could smell her perfume.

Later, at the pizza parlor, we found that we had an audience. Not only my friends, but also Becky’s friends. “Maybe we should introduce them to each other, and they might leave us alone,” I commented.

“They all know each other already,” Becky replied.

When we arrived at Becky’s house after leaving the pizza place, I walked her to her door and we stood there, face to face. I knew that you weren’t supposed to kiss on a first date, but we already had a study date, so I brushed my lips against hers. “You can do better than that,” she whispered, and pulled my head to hers and placed her lips firmly on mine. It was my first kiss. It was wonderful. We kissed again, and Becky said, “I had a wonderful time. Thank you for the movie and pizza.” She kissed me again and then opened her door. I went back to my car like I was walking on air. This dating stuff is great, I thought.

The feeling of euphoria lasted until I got back home. My sister and parents were waiting up for me. My sister examined my face. “Well, we don’t have to ask you how your date was, it’s evident from the traces of lipstick on your face,” she said with a wicked smile.

“Did you have a good time?” my mother asked.

Without waiting for my answer, my sister piped out, “Just look at him, that’s your answer.”

Saturday, September 20, 2014:

The next day I was working in the yard when my three pals ‘just happened’ to come by. Obviously they were looking for an ‘after action report.’

“Well, how was it?” Joe asked.

“It was okay,” I responded, “you ought to try it yourself.”

“Yeah, but . . .” Harry stammered.

“I know, you have to ask a girl to go out with you. They aren’t going to ask you,” I said. “You could have asked Cathy, Sue or Judy last night at the pizza place.”

“I probably would have been shot down,” Joe said dejectedly.

“I don’t think so,” I responded. “Becky told me that Sue thinks you’re kinda cute, in a nerdly way.” I added with a snicker. “Look, I have an idea. At lunch on Monday, all four of us can ask Becky, Cathy, Sue and Judy if they want to play miniature golf on Saturday evening. It’s like a group date,” I said.

“Hey, that might work,” said Harry, “I’m up for it.” Joe and Bob nodded their heads in agreement.

“Just keep your cotton picking hands off of Becky,” I added menacingly.

“Ooh, so that’s the way the wind is blowing,” Joe exclaimed, with a big grin.

Monday, September 22, 2014:

At lunch on Monday, the guys and I approached the table where Becky, Cathy, Sue and Judy were sitting. “The guys and I would like to challenge you girls to a game of miniature golf on Saturday,” I announced. All of the girls smiled.

The girls cut right to the chase. “What time?” Cathy asked, as if the invitation had been accepted, which, as it turned out, it was. The other girls nodded in agreement.

So the eight of us showed up at the miniature golf place at 7:30 that Saturday evening. Was it officially a date? I can’t say one way or the other, but all of us guys were wearing slacks, not jeans, shirts with collars and leather shoes. The girls, not to be outdone, were wearing skirts or shorts with cute tops. All of the girls were wearing subdued make up. I, for one, was impressed.

I had clued the guys that the girls probably expected us to pay, which was true. We then split into two groups, Joe, Sue, Bob and Cathy in one group, and the rest of us in the other. All the time Becky kept a tight grip on my hand, as if to say that I belonged to her. The other girls seemed to accept this. While we kept score, it soon became apparent that social interaction was much more important, because at the end of the game everyone had a date to the Homecoming dance.

Cathy and Becky then suggested that we play another round and even offered to pay. The catch was that the girls had made plans for a Halloween party, and the winners could chose the Halloween costumes for the losers. I figured that guys are just naturally better at this than girls, so I started with a confident attitude, which soon turned to worry. It appears that Becky had an eye that a professional golfer would envy. I lost by one stroke, but that was enough.

“Oh, I’m going to have so much fun with this,” crowed Becky, “be at my house on Sunday afternoon, for our study session and we can think about your costume.”

My parents were still up when I got home. “So, how was it?” my mother asked. I told her how as a result of the evening all of us had dates to the Homecoming Dance. “Well, it’s about time that you guys got off of your rears and did something mature,” she added.

I then let the other shoe drop, and told my parents about the bet we had for the second game. “So, how much did you beat Becky by?” my father asked.

“I lost,” I admitted.

“Oh, this should turn out to be interesting,” my mother said with a wicked smile, “I want pictures.”

My sister just giggled.

Sunday, September 28, 2014:

On Sunday afternoon, I showed up at Becky’s house to study for a test on Monday. The subject of the Homecoming Dance and the Halloween party were discussed. Becky must have told her parents about the wager, to judge from the gleeful smiles on their faces. “I guess that Becky forgot to tell you that she took third place at the girls under 16 golf tournament a year ago,” her father said with a chuckle.

“Yeah, it must have slipped her mind,” I said ruefully. Becky was just gave me a sly smile.

We studied hard for several hours, and when we felt that we had a good grasp of the materials we relaxed. “What do you think about the essay that was assigned in the sociology class?” Becky asked.

“It’s going to be difficult,” I responded and fished the assignment from my backpack. It was due in two weeks. “Sexual stereotypes; what it would be like to be the other sex,” I read off the sheet of paper. “I have to write what it would be like to be a girl, and you have to write what it would be like to be a boy,” I read on, “We have to incorporate some of the sexual stereotypes which we discussed in class. One good thing is that we can discuss this with each other,” I concluded.

“It’ll be a lot of fun working on our papers with each other,” Becky added. “I feel sorry for the kids who don’t have a boy or girl friend.”

“They’ll have to find one soon, or have a fertile imagination,” I added. I didn’t have a clue what it was like to be a girl. Becky, on the other hand, had formed a plan to educate me on that point, and it had to do with a skirt. Naturally, she kept this to herself.

Roy And The Road To Renee - Chapter 2

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Voluntary

Other Keywords: 

  • Shopping trip

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 2.
By Pentatonic

Friday, October 3, 2014:

Becky and I had decided to invite our friends for a joint session to work on the essay on Friday after school. Before our meeting, Becky and I discussed the essay, especially the stereotypes which had been brought up in class. Thank goodness both Becky and I had good notes. My friends and Becky’s friends were not so fortunate so the joint study session benefitted them. By now Joe and Sue seemed to have paired up, like Harry with Cathy and Bob and Judy working with each other.

While we all together, I asked the guys if they had looked at the information for the dance. I told them that the boys should wear a suit, or at least a coat and tie. “I looked at my clothes, and came up with nothing. My Mom is taking me shopping tomorrow.”

“Ooh, can I come along?” Becky asked.

“I plan on getting in and out of the store in less than thirty minutes. From what I’ve seen and what we’ve discussed, taking you might turn it into a two hour session.” I immediately regretted my comments when I saw the hurt expression on Becky’s face. In the next second I withdrew what I had said, and told her that I would be delighted to have her along.

Saturday, October 4, 2014:

On the way to the mall, Becky and I explained our essay requirements to my Mom. “Maybe I can help you with it.” she said.

My mother and Becky dropped me off at the men's wear department, and took off on an adventure of their own. As mom explained it, “I’m going to borrow Becky as my daughter for the day to shop with.” For some reason both Mom and Becky began giggling madly.

Shopping for men’s clothes is easy. First you find a clerk, or more likely the clerk finds you, especially if he is a commission salesman. “And what can I help you with, young man?” he asked. I explained that I needed a suit or a coat and slacks, a white shirt and a tie to wear to the Homecoming dance. “Excellent,” he said, “By the way, do you know what size you are?”

“Not exactly,” I answered, and he whipped off a tape measure which he had around his neck. He measured my neck and sleeves, “for the shirt,” he commented. He then measured my chest, waist and inseam. “Hmm,” was his initial comment, followed by, “Why don’t you come over here, I think that the clothes in this rack are your size.”

“You might want to consider buying separates, that is a coat and slacks. We can find slacks that match the coat, for a suit, and you can buy another pair of slacks which contrast with the coat, for a different look. Essentially two outfits with the same coat. We should look at a tie that goes well with the contrasting slacks. Another point is that you would be buying slacks off the rack, and they will not need the cuffs sewn.”

At my mother’s suggestion I had worn a cotton button down shirt, since I was going to buy a coat. The salesman noticed this and said, “Good choice of shirt, since you will be buying a coat.” I secretly thanked Mom.

“I would suggest a black coat, or maybe a dark charcoal or maybe a dark navy blue. We have slacks made by the same manufacturer, and the color and material are practically identical. I would suggest a gray pair of slacks for the second pants, since they will go well with any of the coats.” With that, he pulled three coats off the separates rack, and I tried each one on. He buttoned up each coat and pulled on it to make sure there was enough room. He then adjusted the rest of the coat, and each time I walked to the mirror to see how it looked. All three worked.

“You could get the coat in a size larger, which would give you some room to grow into,” he suggested. “The sleeves will be a bit longer, but not so much that anyone will really notice. You’ll just have to make sure that you don’t drip them into the soup,” he added with a chuckle. “Now lets find some slacks.” He went through the rack looking for the correct waist and inseam. “We can go up a size on the waist, because they are a bit tight in the rear and maybe also on the inseam. Here, try these on.” He handed me four pairs of slacks and directed me to the fitting room. “While you’re doing that, I’ll look for some ties that I think will go with the gray slacks.”

“I have my Mother with me, at least somewhere in the store, and I’m sure that she will have final say, since this is all going on her credit card,” I added.

With a conspiratorial wink, he said, “As long as you have a woman in your life, she will have the final say. Just look around you. almost all of the men are accompanied by a woman who is making all the final choices. Now if you don’t mind, I’ll take care of some other customer while you’re waiting for your mother. Just wave to me when she comes in.” I knew that it would be inconsiderate making him wait with me for who knows how long, when he could be earning another commission.

At long last, Mother and Becky came back into the men’s wear department, laden with bags and carrying on non-stop conversations, except for when they broke into laughter. What was most disturbing was that most of the laughter came when they were looking at me.

“Now let’s see what you picked out,” she said. I waved to the salesman, and he nodded his head and made his way over to me.

He explained the concept of separates, and I modeled each of the slacks with each of the coats. “They’re all rather somber,” my mother commented.

“That’s true, but they are suitable for all occasions,” the sales clerk commented.

“Just like the LBD,” Becky chirped in.

“You’re quite right,” my Mother said.

The coat and slacks matter having been resolved with the second slacks being a gray one, we all turned to the buying of a tie. Needless to say, the clerk’s choices and my choices were disregarded the moment when Mom and Becky pawed through the tie collection. Finally, I had enough and said, “Look, I’m the one who has to wear it, so I should make the choice.” Mom and Becky relented, and the sales clerk looked at me with more respect.

We made our way out of the mall laden with clothes. When we were home, I went to my room to remove the tags from the coat, slacks, shirt and tie, and hung them up in the closet. Shoes were not an issue, since I still fit, rather tightly, in a pair of black oxfords from a year ago.

When I came into the kitchen, Mom and Becky were waiting for me. “We thought we would have a light lunch,” Mom said.

“Sounds good to me,” I answered, thinking of a bacon sandwich.

“You know, to write a good essay, you’re going to have to get in touch with your feminine side,” my mother said, as she handed me a frilly apron. “One part of that is you will set the table and fix lunch. I set out the ingredients for a nice salad, so get to it.”

“A salad?” I questioned. “I was thinking more of a bacon sandwich.”

“Hardly,” my mother answered. “You have to think of your figure!” This last comment brought out gales of laughter from the two females. I couldn’t figure out what was so funny at that time. So I followed directions while Mom and Becky engaged in a non-stop conversation which included not only giggling, but even some outright laugher.

When the salads were on the table, we all sat down, or rather they sat and I slouched. “Sit up straight, knees together,” Mom commanded. “In fact, sit on the front of the chair with your back straight,” she added. To reinforce the point, both Mom and Becky demonstrated how it was to be done. “This will help you get in touch with your feminine side,” she explained, “It will help you with your essay.”

An evil thought ran through my mind. “If I have to do this to get in touch with my feminine side, shouldn’t Becky slouch and occasionally give out a loud belch to get in touch with her masculine side?” I expounded.

My mother gave me a disgusted look, and said, “She doesn’t need to practice being a slob, after all she’s observed you and your friends for many years. You might not realize it, but girls do pay attention to that.”

When lunch was finished I got to clean up the table and wash the dishes, while Mom and Becky relaxed in the living room. Finally, I was able to hang up that dang apron and join them. I plopped into an easy chair and sprawled with one of my legs over the arm of the chair. This was met with immediate and stern disapproval. “That won’t do at all!” exclaimed my Mother. “Stand up and sit correctly in that chair.” She pointed out to a straight backed chair with no arms. I sat in that chair, remembering my instructions from lunch. “Much better,” she said, “but don’t get too comfortable, because you need to take a shower.”

“Why?” I questioned, “I took one this morning.”

“Because you need to use a hair remover. I left it on the sink. Just follow the directions on the label.” I didn’t like the way things had been progressing ever since we returned from shopping. Maybe I’m being paranoid, but I felt that Mom and Becky have been plotting against me all morning, and the laughter was at my expense, Naw, I answered my own question, but in this case I was wrong, they had been plotting.

“While you are in the shower, Becky and I will put some clothes on your bed for you, and you WILL wear them,” Mom said with emphasis on the word ‘will.’

“If you need any help, just call,” Becky said with a helpful tone in her voice.

When I walked into my room I saw a pair of pink panties, a pink bra, a white garment which I found out later was a camisole, a half slip, a pleated plaid skirt, a white blouse with short sleeves, a pair of panty hose and a pair of sandals with one inch heels. “Put on all the clothes except the pantyhose,” my Mother directed. “I’ll help you with that. I don’t want any runs. I’ll do your hair when you’re dressed.” My hair is just above my shoulders, and I wore it in a low ponytail. With that she and Becky left my room and closed the door, all the time giggling to each other.

“Why?” I shouted through the closed door.

“To help you with your essay,” Mom answered. “You should be thankful, I’ll bet that none of the other moms are doing this for their sons.”

While standing there wearing only the panties and the half slip, I requested help with the bra. Both came into the room, and Becky showed me how to put on the bra. “It’s only a padded training bra,” she said, “It’ll give you a little shape. I picked this one out all by myself, just for you,” she added with an innocent looking smile.

“While you’re doing that, I might as well do the pantyhose. Sit on the bed and lift up your slip” When I did as I was told, she noted the bulge in my panties. “That won’t do,” she said. “Go back in the bathroom and tuck yourself back. If you can’t figure out how, I’ll come in and do it for you.”

“I’ll figure it out,” I said, and I did.

She then showed me how to put on the pantyhose. As the smooth nylon slid up my smooth and hairless legs, I could feel a tingle through my whole body. Finally I put on the camisole, blouse and skirt. I put the sandals. My mother fussed with my hair, giving it a somewhat feminine look. We then went downstairs where I was given lessons in feminine deportment and how to walk in heels.

After two grueling hours, Mom said, “You kids need a break. Why don’t you go for a nice walk around the block?”

“Like this?” I exclaimed.

My question was answered with a withering look. “Exactly like you are!”

Hoping against hope that no one would see me, I stepped out on the porch. I immediately felt the breeze under my skirt. Not a bad feeling. My hopes of being unobserved were dashed when I saw Joe riding up the street on his bicycle. He called out to Becky, “Have you seen Roy around? I need help getting my car started.”

“Roy’s around, and even closer than you think,” she responded and pointed her thumb at me. With that he came closer.

“Holy shit!” he exclaimed as he took a good look at me, “is that really you, Roy?”

“Of course it is,” Becky answered, “Who else do you think I’d be hanging out with?”

“What’s the deal, Roy?” Joe asked.

“My mom, Becky, and who else I don’t know, thought it would help me get in touch with my feminine side and help me with my essay,” I responded.

“When you can, I’d like you to help me with my car,” Joe said.

“Did you replace the battery cables, as I told you to do a week ago?” I enquired.

“Uh, I kinda forgot,” he said sheepishly.

“Then take your bicycle to the parts store, get the cables and put them on,” I commanded.

“I don’t know about getting auto repair instructions from a guy wearing a skirt,” he said, insultingly. He then smiled and said, “When Mrs. Benson picks an essay to read to the whole class, I hope it’s yours. It’d be a real hoot,” he added with a smirk. “Say, did you go whole hog, like panties? If so, can I see?”

“No, you pervert,” Becky answered for me.

“I’m a pervert?” he said, “I’m not the boy wearing a skirt and who knows what else. Call me when you can.” He then added, “By the way, Becky, when are you going to get in touch with your masculine side?”

“I already know how to be an inconsiderate slob from watching you guys, and I know how to scratch my crotch and belch loudly. What else is there to learn,” she said. With that, Joe rode off on his bicycle, laughing.

I thought that I now had one example of a stereotype. We circumnavigated the rest of the block without incident, but on entering the house I complained loudly to my Mother, relating the gist of the incident with Joe. “That was a valuable lesson for your essay, you should be happy that it occurred.”

I wasn’t. At least Dad hadn’t seen any of this, since he was golfing all afternoon with his pals.

I was reminded that the next session would be on Sunday, starting at Becky’s house and then the mall, all the time with me dressed as a girl. It appears that Becky’s mom was in on the plot.

“Wear your panties and pantyhose under your jeans when you come over,” said Becky as she left.

That night, as I was getting ready for bed, my Mom came into my room and handed me a long nylon nightgown with spaghetti straps. “It’ll remind you of your time as a girl today,” she said.

I didn’t see any sense in complaining, so I put it on. It gave me a wonderful feeling. As I contemplated my day, I thought how it wasn’t so bad wearing girl’s clothes, in fact, I rather enjoyed it, and part of me was looking forward to tomorrow, dressed as a girl and being a girl.

Sunday, October 5, 2014:

On Sunday afternoon I drove over to Becky’s house. Her mother greeted me at the door. “Hi, Roy,” she said, and then stopped, “what with all that is going on, we can’t very well call you Roy, can we?”

“I guess not,” I responded.

“Then what?” she asked.

“I thought about it last night. How about Renee?”

“Then Renee it is. Becky, did you hear that?”

“I did,” Becky responded, “I think it’s a wonderful name.”

Becky’s Dad was sitting in the living room and heard the exchange. It was obvious that he knew what was going on, since he said, “I really applaud the depth of your research for the essay.” Becky’s Dad was a researcher for a firm known for the extent they involved themselves in experimentation.

“Thanks,” I replied, “It has been a really different experiment, and I think I’ve already learned a lot.”

This seemed to satisfy him, because he came up to me and shook my hand. “Keep up the good work. I might say that you might want to keep a journal of these events. It might be useful if you ever go into the social sciences.”

Wow, I thought to myself. He actually approves.

As Becky and I went up to her room, she called over her shoulder, “Mom, can we borrow your wig?”

“Certainly, Honey, let me get if for you.”

I quickly got dressed in the clothes Becky had laid out for me. “You know, Renee, it might get colder this afternoon. Why don’t you let me find a sweater that goes with that skirt?”

“Okay, sure, thanks,” I responded.

Becky’s Mom arrived with the wig which she fitted on my head, first putting on a wig cap. During this, she kept up a running explanation of what she was doing, “for future reference,” she said, “While I am working on Renee’s hair, you might want to work on her makeup. Did you buy any for her yesterday?” I guess the use of feminine pronouns was acceptable given how I was dressed.

“Yeah, Mom, I got the basics.” responded Becky, “I got some lipstick, mascara and a little blush. I had to guess at her colors, since Renee was not present at the makeup counters.”

“I have colors?”

“Of course, all girls pick makeup to complement their natural colors.” I didn’t know that and quickly admitted it. “Just another step in getting in touch with your feminine side,” she added.

When everything was done, I studied my reflection in the mirror. I did not recognize myself. I saw a girl with a nice looking behind, nice legs, but not much on top. All in all not bad looking. I decided to give a swirl, much to the delight of all present.

“Ready for the mall?” Becky’s Mom asked.

“Uh, yes, but could you give us a ride. If anyone saw me get out of my car, they’d know it was my car and that I was getting out of it. It would be better if you drove.”

“Okay, I understand. Becky, do you have a purse for Renee to use?

“I do,” Becky said, and produced a purse with a shoulder strap. “Put your stuff in it, and put it over your shoulder. By the way, I put a pad in it first, in case some other girl is not prepared for her period. Most girls carry one just in case, or to give to an unfortunate.”

“Oh, by the way, you’ll have to use the women’s washroom. It’s an experience you can’t afford to miss for your essay. Just remember to sit when you pee.”

What followed was a novel experience for me. First thing I noticed was the boys. Neither Becky nor I were drop dead gorgeous, but that didn’t stop the boys. The leered, they stared, they mentally undressed us. In general, they were boors. It hurt to remember that I had acted exactly like that on many occasions. I vowed to clean up my act in the future. Becky confirmed that the boys’ behavior was how they usually conducted themselves.

The next part was shopping for clothes for hours, but not buying anything. After a while I began enjoying shopping. It was so unlike my shopping experience when I bought my clothes for the Homecoming Dance.

Then came a visit to the food court. Here the boys circled around like vultures over a fresh kill. I recognized it for what it was, since I had done the same on numerous occasions. They were attracted to the girls but it was obvious that they were really scared of them. Then Becky taught me long distance flirting, “Catch a boy’s eyes and smile at him, until he finally comes over and asks if he could join us. Then the short range flirting begins. Batting eyelashes, smiles, and making a boy feel if not comfortable, at least less uncomfortable.” Becky then taught me another two lessons. First, do not make eye contact with the most brazen of the alpha males, you don’t want to have anything to do with them. The second lesson was just as important; never do this alone. Always have at least one other girl with you, for your own protection.

The last experience was the women’s washroom. I went into a stall, which could have been cleaner, and remembered to sit. Then came the conversations at the wash basins with fresh lipstick appearing to be the first priority. What was most strange to me was how the girls described the boys they had seen in the food court. I could hardly keep from blushing, the girls’ comments were so frank. I hated the thought that on some occasions my friends and I might have been so discussed. There were comments about what some of the girls wanted to do with some of the boys. Not being that good looking I hoped that I had never been the topic of these washroom discussions.

When Becky and I left the washroom I commented on what had been said. I said to her that I imagined that I had never been the subject of those kinds of discussions. She quickly disabused me of my misconceptions, and she related what had been said about me, and the questions of what she was going to do with me. I was embarrassed. Then she said, “Some of the girls commented that you have a cute butt, and it really fills out your skirt.” I had never thought that my butt was cute; I only knew that it was larger than average.

Finally, we called Becky’s Mom and she picked us up. Once at Becky’s house, her Dad wanted to know the results of the experiment, and encouraged me to write them down as soon as possible. He told me to be sure that I noted what happened when Joe showed up the previous day, “Don’t only state the facts, write down how you felt, and what was happening around you at the time,” he said. “However, at the same time, don’t omit any of the facts. They are the basis of your experiment. How you felt are also facts, but they also are part of your conclusions.”

His comments were really helpful. I had never approached a topic using this method. “What I just told you was what you would put in a scientific monograph. An essay can consist of feelings and conclusions without as much reference to the facts. When you write up your essay, I’d like to see it.”

When I arrived back home, my Mother wanted to hear all about it, but I told her I wanted to put what happened in writing before I forgot any of it. Just then my Dad came into the room. I hadn’t changed out of my girl clothes. “I’m Roy’s Dad,” he said, “and who are you?”

“I’m Renee,” I answered

“Is Becky around,” he asked, clearly confused with the situation. I gained some satisfaction that he did not recognize me.

“No, she’s at her own house,” I answered.

“Okay, then where’s Roy?” he asked.

“Right here,” my Mother answered, and immediately dissolved into gales of laughter.

“I don’t see what’s so funny,” he said. Then remembering the answer to his question, he stared at me.

“You,” I answered. “You don’t even recognize your own son.”

“Roy, is that really you?” he asked, “What’s going on?”

I explained the essay and Mom and Becky’s plan. When I got to the part of Becky’s Dad’s comments, he softened his face. “He’s a good man, and if he thought it was an experiment of merit, I have to agree with him.”

After supper, I reminded my parents that I had to write up my journal while what happened was fresh in my mind, and I went to my room and turned on my computer. It was well past my usual bedtime before I finished. My Mother came into my room to wish me good night. “Don’t forget the nightgown, it will help you with your thoughts.”

I didn’t forget the nightgown. I realized that I loved wearing it, as well as my girl clothes.

Roy And The Road To Renee - Chapter 3

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Costumes and Masks
  • Shopping

Other Keywords: 

  • Queen of the Night

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 3.
By Pentatonic

Monday, October 6, 2014:

Immediately after I came home from school on Monday afternoon I changed into my girl clothes, to connect with my experiences. That had been Becky’s suggestion. I then re-read my journal and started on the essay. I noted the stereotypes which were relevant to my experience, and decided to limit my essay to just those points. According to the instructions, Mrs. Benson wanted the essay to be at least one thousand words. My first draft was twice that. I set it aside to polish it over the next few days. I changed out of my girl clothes for supper, to avoid any snide comments from my sister although something in me was saddened when I did.

At that point I realized that having let my feminine side out, she wasn’t going to go away without a struggle. I decided to keep the name Renee for my feminine side.

Friday, October 10, 2014:

Friday was the due date for turning in the essays. As suggested, I included my journal with the essay, since I made a lot of references to it. It made a thicker than usual essay, and Mrs. Benson smiled with approval.

Friday was also the day before the Homecoming dance, but the buzz of excitement at my lunch table covered the fact that my essay was a whole lot longer than everyone else’s.

Saturday, October 11, 2014:

The Homecoming dance was held in the school cafeteria, rather than in the gym. I thought that the gym would have been more appropriate, given the sporting event theme, but the basketball coach had refused to let the school use the gym, because, as he said, “I don’t want a bunch of stupid girls ruining the floor with their idiotic high heels.” I, for one, couldn’t care, but I wished that I could have included his comments in my journal and essay.

The lunch tables had paper table cloths in the school colors, and streamers had been hung from the ceiling. Some of the tables and chairs had been moved out to make room for a dance floor. It actually looked pretty nice.

Becky and her friends had really dressed to look very pretty, and us guys were all decked out in coats and ties or suits. We moved two tables together so all of us could be together. Our presence was noted. The captain of the football team came up to our table. “I didn’t expect all of you to come. I guess that you aren’t as nerdly as I thought,” he commented. From him that had to be high praise. We traded dances with each other, and genuinely had a good time.

When I took Becky home, she said that my getting all of us together for the dance had been a great idea, for which she rewarded me with long and lingering kisses before she went inside. I didn’t go in with her, since I knew from experience that I had traces of her lipstick on my face, and didn’t want her parents to see it.

I was not so fortunate at my house. My sister had been at the dance and she and my parents were in the living room, waiting up for me. The comments about the traces of lipstick were accompanied with giggles and outright laughter from my sister. “It looks like you had a better time than I did,” she commented.

Tuesday, October 14, 2014:

On the next Tuesday, Mrs. Benson commented that she had read the essays over the weekend, and while she usually picked three essays to be read in class on Friday, there was one essay which really stood out, so she was going to dedicate a whole class session to reading and discussing it on Thursday, and have three other essays read on Friday. Her comments caused Becky to look at me and smile. She was sure that my essay was the ‘special’ one.

Thursday, October 16, 2014:

She was right. On Thursday, Mrs. Benson announced. “Roy’s essay is based on his personal experiences, his ‘research,’ as it well may be described, he recorded in a journal. He refers to his journal in his essay, to support his conclusions, so I am asking him to read the journal first, so you can see what he did. As you will hear, he cross-dressed as a girl, to experience what a girl would be expected to do and feel in certain situations. I know that you all want to snicker about Roy wearing a skirt, but let me tell you that some serious research has been carried out in like circumstances, so you have to understand that Roy’s motives were purely scientific. Remember that Becky was an integral part of the research and nothing more should be inferred as to his cross-dressing.”

Boy, I thought, if only she knew how much I liked dressing as a girl.

After class, Mrs. Benson called me aside. “Your essay was way beyond what I expected, and I am dutifully impressed. I have a friend who is a university professor, and I’d like to share your journal and essay with him. Your observations and conclusions come from a 16 year old boy and not an adult. For that reason, it has great value, since very little has been written from your viewpoint. May I send him a copy?”

“Sure, I guess so,” I responded. I then told her about the basketball coach’s comments, and how I wish I could have included that in my journal and essay.

“Write them us as appendices to your journal and essay, and I will include them with what I send to the Professor,” she said.

My method of research caused some commentary among some of the students, but Becky helped explain why it was done. The fact that she participated in the research helped quell any adverse reaction.

That evening, I related the events of the day to my parents and sister. My sister couldn’t help not making some snide comments, for which she earned a rebuke from Dad, “You should respect what Roy did. I’m willing to bet that you wouldn’t even think of putting so much effort in class work, and I have your grade reports to prove it.” This silenced my sister.

Friday, October 17, 2014:

The next day Becky read her essay in class. Her essay was connected with mine, although a lot shorter. She wrote about her feelings and conclusions from the events in my journal, some which differed from mine. Mrs. Benson was actually excited about our joint effort and said “You heard Roy’s essay yesterday. Becky’s essay relates to the same events, but with a different viewpoint and some different conclusions.”

Becky was excited about our essays. On our way home from school she said, “Mrs. Benson told me that they are almost one work with two authors. She said that my participation has earned both of us an ‘A.’ Now that all of your friends know that you have cross-dressed makes selecting your costume for the Halloween party a lot easier.”

“Let me guess,” I responded, “it has to me dressing in a skirt or dress, doesn’t it?”

“Now that you mention it, it does,” she responded with a big grin. “I was thinking of an opera theme for us. I could go as Brunnhilda from ‘Die Walkyrie’ and you could be the Queen of the Night from ‘Die Zauberflote,’ How does that sound?”

“Okay, I guess,” I said, “but putting together the costumes may be difficult and expensive. Don’t expect me to sing any of her arias,” I added.

“You don’t mind wearing a dress, do you?” she asked.

“Naw, it’s okay,” I told her. I didn’t say that I would really love to wear a dress. My feminine side was reasserting herself.

“Let’s see what we can find at the thrift store, for starters. Since we will be in the women’s section and you will be trying on dresses, you might want to wear a skirt and top. Maybe you can bring your clothes from your house, get dressed at my house and then we can hit the thrift store tomorrow.”

Saturday, October 18, 2014:

On Saturday morning I used the hair remover again, since I was going to be changing into a skirt at Becky’s house. For the drive over I decided to wear panties and pantyhose under my jeans for two reasons. First, I would be wearing a skirt when shopping, and Second, just because I wanted to. My feminine side was active. I wore regular socks over my pantyhose, packed up my girl clothes along with what makeup I had and drove over to Becky’s house.

Becky’s Mom answered the door when I rang, and when inside I could hear strains of Wagner coming from the CD player.`”I’m excited about your Halloween costumes. I love the opera, especially Wagner. Becky told me to send you upstairs to get ready for some shopping.” She paused for a second, and then asked, “You don’t mind it that my daughter has you wearing skirts and dresses on occasion, do you?” Without waiting for an answer, she added, “It’s almost like you are her full sized Barbie Doll.”

“It’s okay,” I responded. Then my feminine side asserted herself and I added, “I wish I had Barbie’s figure.” Becky’s Mom had a peculiar smile on her face when I said that, and she pointed to the stairs.

Becky was laying clothes out on her bed when I entered her room. “I think that this plaid skirt and a button up sweater are appropriate for today.” Rather than going into the bathroom to change, I took off my jeans in front of her. What started as a concerned look on her face dissolved into a broad smile when she saw that I was wearing panties and pantyhose under my jeans.

“You told me that girls don’t mind getting undressed in front of each other,” I said, to justify what I had just done.

“Do you consider yourself to be a girl?” she asked with a surprised look on her face.

“When I’m wearing panties and a skirt, the answer is yes.”

“Oh,” was her only response.

“Let me explain,” I said, “when I had to get in touch with my feminine side, it wasn’t a mere touch. My feminine side grabbed on tight and won’t totally let go any more. I call her Renee and she is always in the background.”

“Well, then, let’s get Renee ready,” she said with a bright smile.

When fully dressed we went out to my car. “Aren’t you afraid of someone recognizing your car and seeing you get out in a skirt?” she asked, referencing my prior concern.

“Not anymore,” I said, “Renee won’t let me be concerned,” referring to my feminine side.

“Will Renee allow you to kiss me?” she asked with some concern in her voice.

“Renee has nothing to do with kissing you,” I said, “that’s exclusively Roy’s province.”

“Good!” she said, “now prove it!” I did, and it seemed to please Becky. But, I wondered, does my Renee side want me kissing boys? That was more than I wanted to think about at that time, so I pushed that thought into the back of my brain.

We were lucky at the thrift store. After a lot of searching, we found a long black formal dress which actually fit me. The skirt part was slightly gathered at the waist, and the whole skirt would spread out if I twirled. It also had a slit up he left side of the skirt which came up to mid thigh. The bodice was not tight, and the neck line was square cut. It was sleeveless but had wide shoulder straps. A further search produced a long sleeved, high neck chiffon blouse with a small ruff around the neck. “You can wear this under the dress,” she told me, “maybe we can make a high collar in back and attach it to the blouse.” The dress and blouse were purchased. “I hope you know that everything you wear underneath will also have to be black, so we’ll get it at the mall. I think that you will also need ample breasts, so you want to think about breast forms.”

For Becky, we found a long formal gold skirt and a silver sleeveless top. The housewear section of the thrift store had some metal bowls which we could make into an armored chest-piece. We also found a blond wig which would be long enough to make into braids. The helmet with horns was a problem, however.

We found a solution in a man’s hat with a rounded top. We could cut off the brim, and spray paint it silver. We did some research on the internet, and found that some Brunnhilda costumes had wings, and not horns, on the helmet. We decided to use wings, which we could cut out of cardboard and painted.

After our thrift store adventure, Becky and I returned to her house to drop off our purchases and have a bite to eat. We then left for the mall, and more shopping.

On the way to the mall, Becky went over what we needed to buy. “We need black panties, black bra, black slip, black pantyhose, unless you want to wear a garter belt and stockings.” The last comment brought a wicked smile to her face. “We need some costume jewelry, and I think that we need some sequins to decorate you costume, since you are the Queen of the Night. So where do we start? The department store or Victoria’s Secret? Oh, you need some black shoes with heels. We’ll play the rest by ear when we get to the mall.”

Upon entering the mall, the first place we saw was an earring kiosk. Becky immediately saw a set of crescent moon earrings. “Ohhh!” she exclaimed, “You definitely need those.”

“But they’re for pierced ears,” I complained.

“That’s an easy problem to solve,” Becky said in rejoinder. “Piercing is free if you buy earrings.”

“We’ll buy the crescent moon earrings and a set of small gold studs for her to wear until the holes heal,” Becky told the sales clerk. The clerk called over an older woman, who brought over what had to be a medieval torture device, used to pierce ears and who knows what else.

After some pain to my ear lobes, and some minor pain to my cash supply, Becky and I proceeded down the main aisle.

As we approached a ‘fashion jewelry’ store, Renee said, “The Queen of the Night needs jewelry!” and we went into the store. In keeping with the Queen of the Night motif, Becky found a pewter necklace with a man in the moon face. “You absolutely need this,” she said. She saw a plastic tiara and some cheap, but gaudy, rings, all of which were purchased.

“You need some makeup. What you have just won’t do it,” Becky said. “Black nail polish, blood red lipstick, heavy eye shadow, false lashes, and some dark blush, definitely. We can get this at a cosmetic counter in the department store.”

As luck would have it, Victoria’s Secret was on the way to the department store at the far end of the mall. “Let’s see what they have,” Becky said as she pulled me in the store. She then reached into her purse and pulled out a list of measurements which she had previously made.

“What size panties are you wearing?” she asked. “Panties are always a good place to start.”

I didn’t understand the logic of her last statement but let it pass. It wasn’t hard to find the right sized panties; it was the style which concerned me.

“I think that Renee will want the sexiest pair possible,” Becky said.

“Remember, I have to tuck something back, so we have to consider that.” I said.

“Well, okay,” she responded, and found an appropriate pair.

“We can buy cheap pantyhose at the local drug store, so we don’t have to get them here,” she said, “of course, unless you want to wear a garter belt and stockings. Then this is the place for them.” Becky picked up several black garter belts in different styles and sizes, and we went to the changing rooms. She entered the changing booth with me. Facing me, she reached around and unfastened my skirt which fell to the floor. She then fastened a garter belt on me. After trying several, she made my choice for me. “Ohh, that is so sexy,” she said. “It makes me want to kiss you,” which she did. She then looked at my face. “You need to fix your lipstick,” she said.

“And so do you,” I responded, and we did. Becky then selected a pair of black nylons for me.

After the garter belt and stockings, Becky said, “Now you need a slip, because your gown is not lined. I think a full slip would be best, but we only want a peek of lace to show in the slit in your gown. Maybe a slip with a lace edged slit on the left side, same as the dress. That way when you twirl, you might give a glimpse of garter and hose.”

After buying the slip, Becky and I went to the bra counter. “How can I help you ladies?” the clerk asked.

“A black bra with lace. C cup,” Becky said, and she gave the clerk the appropriate measurement.

“For you?” the clerk asked Becky while looking at her chest.

“No,” Becky replied, “for her.”

The clerk shifted her attention to my chest. I had the start of ‘man boobs’ but nowhere in the C cup range.

Seeing the clerk’s expression, Becky added, “She’ll need some inserts too.” In response, the clerk gave me an odd look and shrugged her shoulders, which I ignored. After looking for a bra, sexy and lacy enough to satisfy Becky, and full enough for the breast forms, the clerk, Becky and I repaired to a cubicle for me to be fitted. At last, we had what was needed. I was slightly embarrassed with my encounter with the clerk and I was relieved when we left the store.

At last we made it to the department store, for cosmetics. Becky steered me to one of the counters. “This is my favorite brand,” she explained. The clerk smiled when she saw us, and I remember hearing that the cosmetics clerks were on commission. Since we needed to buy a lot of cosmetics, she had reason to smile.

“Renee here is going to a Halloween party as the Queen of the Night, from the Magic Flute.” The clerk looked puzzled. “From the opera,” Becky added, but it still didn’t seem to register with the clerk. A catty remark from my Renee side came to my mind. She probably only likes acid rock, I thought.

Becky came to the rescue. “Think evil witch. Black nails, blood red lipstick, dark eye shadow, false lashes, and anything else you can think of.” This brought a smile of recognition to the clerk’s face.

“How are you set for your regular cosmetics?” the clerk asked me. “We have a special on complete kits in different colors, and I know we have what is exactly right for you/ Do you want to see it?”

Becky pulled me aside and whispered, “It may be a good idea if Renee plans on hanging around, otherwise not.”

“Yes, I’d like to see it,” I said.

“Very interesting,” Becky commented, as if I had answered a question, which, in fact, I had. This pleased my Renee side.

After trying some of the cosmetics, I said that I would buy the set. We then concentrated on the Queen of the Night makeup. When done, I looked in the mirror and saw what looked like an evil prostitute. “Excellent,” Becky announced. “We’ll buy them.”

We left the Queen of the Night makeup on as we went in search of shoes. When I saw people staring at me I wondered if they thought the makeup too dramatic or that I really was a prostitute. The Renee inside of me didn’t care, but she did like the makeup.

The clerk at the shoe store tried to steer me into buying strappy shoes with dangerously high heels, I was finally able to prevail on the heel height,

When we got to the car, Becky suggested that I put on my heels, to practice driving in them.

At Becky’s house, her Mother loved the Queen of the Night makeup. “Can I see what else you bought?” she asked. She liked what we had bought, and had a lot of suggestions for my costume. She even approved of the garter belt and stockings. “They’ll really get you into the part,” she said.

We started work on the costumes immediately. Sequins were found and attached to the chiffon blouse. The helmet was started, and cardboard wings were made. Of course both Becky and I had to model what we had bought. When I stripped down to put on the dress, Becky’s Mom noticed that I was wearing panties and pantyhose. “Good idea, it puts you in the right spirit,” she said.

When I sat down to put on my heels, Becky’s mom noticed the slit in the skirt. “You’ll have to be careful with that, or you’re going to give everyone a peep show,” she said with a chuckle. “If you want, I can sew that closed.”

“No,” I said, “I like it the way it is.” That was Renee talking.

“I figured that you would,” she responded. I wondered if Renee was sending out signals.

Becky’s Dad liked both operas, and as his contribution had made a spear for Brunnhilda and a magic wand for the Queen of the Night, “I thought that I should contribute something,” he said.

Sunday, October 19, 2014:

Becky’s mom had suggested some alterations to make the dress fit better, and had suggested that I come by on Sunday afternoon to try the dress on to make sure that everything was right. That morning I had run out to buy some extra black hose to wear to the fitting. I decided to wear the black panties, slip and bra along with the breast forms under a skirt and sweater which I borrowed from my mother. “Just remember, this does not mean that you can raid my closet whenever you want,” she warned.

“But mom, this is only for the halloween party,” I responded.

“Yeah, right,” she replied sarcastically.

Becky and her mother had laid the entire costume on Becky’s bed. Neither made any signs of leaving the room while I changed. When I took off the skirt and sweater, both commented on the black undergarments. “I’m glad to see that you made the effort to make sure everything is correct,” Becky’s mother said. She checked the slit in the slip. “Good, you can see the top of her stocking and the garter strap.” Renee liked this, even if Roy was a little embarrassed.

I put on the chiffon blouse to which the sequins had been added and Becky and her mom helped slip the gown over my head, and zip it up. When I sat down to put on my shoes I found out that no matter how I sat, the slit in the skirt fell open, displaying the top of my hose. This caused Becky’s mom to laugh. “You’re going to have to work on that, unless you like giving everyone a bit of a show. “Of course, I could sew it closed if you wish.”

“No, don’t,” Becky said, “I think that she likes giving a glimpse of stocking.” Renee agreed with her.

“Why don’t you keep it on for the rest of the afternoon, and practice sitting and walking in the heels,” Becky’s mom suggested. “While you’re doing that, Becky and I can work on her costume.”

It was then that Becky’s dad came up from the basement with the metal bowls, having fastened them together with leather lacing, which was Brunnhilda’s armored chestpiece. Becky and her mother made adjustments with the various parts of the costume, while her dad and I just watched and admired. When they were done, a very credible Brunnhilda emerged. Becky’s dad had worked on the helmet, and it was fitted to Becky’s blond wig.

Becky’s mom then said, “Let me get the black wig for the Queen, and let’s have pictures.” There were a lot of pictures, which Becky’s mom emailed to my mother. Due to the wonders of the internet, they arrived at my house before I did, much to the delight of my sister.

“Oooh” she commented, “are you really sure you’re a boy? You look so adorable,” she said, and dissolved into gales of laughter.

Monday, October 20, 2014:

While I no longer tottered when wearing three inch heels, I decided I needed more practice, so when I came home after school I asked my sister if I could borrow a pair of knee high stockingsfrom her. “Okay, if you promise to wash them when you’re done, and don’t run them,” she said.

So I spent the afternoon in heels, while wearing my jeans and a sweatshirt. I caught my sister looking at me. “That just doesn’t look right. Those shoes don’t go witht the baggy jeans and sweatshirt,” she said.

“It doesn’t have to look right,” I retorted, “I’m just practicing walking in these shoes.”

“How about dancing?” she asked.

“I donno,”

“Maybe you better practice dancing. I’ll help you but not if you look like that. Come up to my room, and let’s see what can be done to make you look better.”

Once in her room she commanded me to strip, which I did, down to my underpants. “Get rid of those too,” she ordered, and handed me a pair of her panties. “These should work,” she said, “If you’re embarrassed, change in the bathroom and come back in here.”

I changed into the panties, and when I went back into her room, she handed me a bra. “Do you have your breastforms or are they at Becky’s?” she asked.

“At Becky’s,” I replied.

“No problem, we’ll find something to stuff them with,” she said. “Put on the bra.”

After I had put on the bra, hooking it behind, she commented, “you’re getting pretty good at that.” She handed me what I recognized as her skating skirt, maroon with contrasting panels, and very short. “It’s not going to bite you, put it on,” she commanded.

This was followed by a top with a very low scoop neckline and adorned with spangles, which I dutifully put on. “Come here, and let me do something with your hair,” she added.

After she had put my hair in a french twist, she grabbed a lipstick, and applied a coating to my lips. I turned around and looked in the mirror, Renee liked it.

“Okay, let’s go into the basement and dance,” she finally said. She grabbed her CD player and some CDs and headed to the basement.

For about an hour we practiced various dances, after which she said, “You’ve got those pretty well down, but now you have to learn some slow dances.”

We had only started on the slow dances when my mother called down the stairs, “Are you down there, Roy? Joe’s here. I’ll send him down,” after which I heard him coming down the stairs. When he saw my sister and me, one could see the surprise on his face.

“Whatcha guys doing?” he asked.

“I’m learning how to dance,” I said.

“As a girl?”

“Yeah, for the halloween party.”

“Why?”

“Because I need to learn,” ignoring part of the question.

“Nice outfit,” Joe said.

“Give Joe a twirl,” my sister commanded with a wicked smile.

I did as I was told, which caused the short skirt to flare out, exposing my panties. Joe gave a whistle.

“As long as you are here, you can help by dancing the boy part,” my sister commented. Joe did not need any further encouragement, and took me into his arms.

“Just remember, I’m a boy,” I warned him.

“Doesn’t look that way right now,” he responded.

The more we danced, the closer he held me. I could feel that he was getting aroused. “Back off, buster,” I whispered, “I don’t go for boys.”

“You could fool me,” he whispered back.

After about a half hour, I asked Joe, “So what brought you over in the first place?”

“I need you to look at something about my car,” he answered.

“Let me change, and I’ll be with you,” I said.

“Naw, it won’t take long, and I like the way you look.”

I put on a short jacket and we went outside. “What seems to be the problem that can’t wait until tomorrow?” I asked.

I suddenly felt Joe’s hand under my skirt and rubbing my behind. “Stop that immediately!” I commanded.

“Why? Don’t you like that?”

“No, not at all.” Well, maybe Roy didn’t like it, but Renee did. “I’m getting cold, let’s go back inside,” I said.

Friday, October 31, 2014:

On the night of the party, Becky and I got dressed at her house. Becky’s Mom had taken pictures of my Queen of the night makeup which the cosmetics clerk had done, and did a credible job of reproducing it.

The party was held in the rec room of Cathy’s house. There were black and orange streamers everywhere, and black chiffon covered the few lights which were left on.

We were nearly the last to arrive, which was good, since we could make a grand entrance. Most of the people in our crowd were not opera lovers, so we had to explain our costumes. I think that nearly all were impressed with the effort we had put into them.

A little later Joe sidled up to my left side. “A dress,” he said. “You must like wearing dresses and skirts. What gives?”

“Remember the game of miniature golf?” I said. “Remember the wager, remember that I lost to Becky?”

“Oh, yeah, That.”

“Yes, that,” I responded, and moved a step away, revealing the mid thigh slit.

“Oh, wow!” Joe exclaimed when he saw a glimpse of the lace at the bottom of my slip and my black nylons. “What else do you have under there?” he asked with a crooked smile on his lips.

“You asked the same question the first time you saw me in a skirt. The answer is the same. I’m not telling or showing,” I said.

“Be that way,” he said, but I could feel his hand on my behind before he went to graze at the buffet table.

I really had to be careful how I moved, and especially how I sat and how I crossed my legs. It was difficult not to show a lot of leg and a lot of the lace on my slip. Later on, Becky and I sat down on a love seat, with Becky to my left. I could feel her hand move into the slit of my dress and rub my nylon covered leg. “Feels good?” she whispered. I nodded my head.

The girls had picked out some party games, most of which caused me to reveal more that I wanted, including the fact that I was wearing nylons and a garter belt. Some commentary and whistles followed. Joe, on the other hand, just announced, “I knew it!” I gave him a dirty look.

A while later, I pulled Becky aside. “Did you have any part in choosing the games?” I accused her.

“Of course I did. You should feel honored, since a lot of the games were picked just for you and your nice under things,” she answered. “I thought that your Renee side would like them.”

I had to admit to myself that my Renee side was a bit of a tart, and to further admit to myself that I enjoyed it.

On the way back to Becky’s house, she suggested that we stop for a few minutes where the trees shaded the streetlights. She leaned toward me and gave me a lingering kiss. “I really had a great time, and thank you for being such a good sport. I’ll bet that none of your pals would have shown up in a dress.”

She paused for a moment, and then said, “Answer me truthfully, you don’t mind wearing girls’ clothes, do you?”

“I don’t mind,” I answered.

“In fact, you like the way they feel on your body, don’t you?”

“My Renee side does,” I answered evasively.

“But both your Renee side and your Roy side actually like to cross-dress don’t they?” she demanded to know.

“Yes,” I said softly.

“And sometimes you wish you were a girl, don’t you?” she asked.

I nodded my head and asked. “Why do you suspect that I do?”

“Your essay,” she responded. “Some parts of it were not a boy imagining being a girl, they were all girl. I don’t think that anyone else noticed, but I did because we shared the same experiences.”

With that we exchanged another long and lingering kiss. She looked into my eyes and commented, “I think you were right when you said that Renee wasn’t going to go away without a fight.”

In the end it was a moot point, since Renee never went away.

Roy And The Road To Renee - Chapter 4

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Shopping

Other Keywords: 

  • Getting a Job
  • dating

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 4.
By Pentatonic

Saturday, November 1, 2014:

The Queen of the Night was a mess. The sun was shining brightly when I awoke the morning after the Halloween party. I squinted at the clock; it was nearly 10:00 a.m. I looked about. My dress from last night was loosely draped over a chair, not hung up as it should have been. I came to realize that I still had my bra on but minus one insert, along with panties, garter belt and nylons. I had no idea where my slip was. My shoes had been abandoned in the middle of the room. Thankfully, I had put on a nightgown, or at least I was wearing one.

I got out of bed, somehow found a robe and made my way to the bathroom. My face was a mess; I hadn’t removed my makeup, but I, or someone, had removed my wig. I absently wondered where it could be.

Surveying the wreck in the mirror, I decided to remove the makeup as a first step to normalcy. Normalcy? How could I consider myself as anywhere near normal. After I cleaned off my makeup I stripped off the remainder of my clothes and stepped into the shower. First thing to do was to clear the cobwebs from my brain. A good shower was just the thing to do that.

After my shower, I put my robe on and picked up my discarded clothing from the floor of the bathroom. I stepped into the hall, and surprize of surprizes, came face to face with my mother. “Well, it looks like someone had a good time last night,” she said as a greeting. I just grunted as a reply.

“What time did I get home?” I wanted to know.

“Late,” she answered, “but you then flopped onto the couch and feel fast asleep. Your sister and I finally got you to your room and into a nightgown. I hope that you appreciate that we didn’t undress you any further than we did, although your sister wanted to, but I talked her out of it.”

“Thanks.” I mumbled.

“Get dressed and come down for some breakfast. It’ll make you feel better.”

It appeared that my Renee side didn’t object, so I had no problem getting dressed as Roy, with the exception of a pair of lace trimmed panties to please my Renee side. Although there may have been something incongruous about being dressed as I was I went down to the kitchen and started removing my black nail polish. My mother told me that Becky had called while I was still asleep, and that I should return the call.

“Guten Morgen, Konigin, wie gehst,” Becky said. Both Becky and I had studied german, and she liked calling me “Königin der Nacht,” which is german for Queen of the Night. My response was a brief grunt. “That good?” she replied. I told her that I had promised to help Joe with some repairs to his car, and she was welcome to come over to keep Joe and me company. Otherwise we could meet later.

After completing the call, I noticed a bowl of Halloween candy left over from last night. As I reached over for some, my Mother announced, “No you don’t! You’ve got to watch your figure.”

“Why?” I said.

“You may think that you are finished with your Renee side, but my female intuition tells me otherwise,” she said. With that I went back to my room to hand wash that which had to be so washed, hang up other clothes and put the balance in the laundry hamper. I finally located the wig, put it on its form and brushed it out some. Satisfied, I went back downstairs to be greeted by Joe who was polishing off some bacon. Bacon, that my Mother had prohibited me from eating, because of ‘my figure.’ Between my mother’s dietary restrictions and some hard exercise on my part, I was able to lose some weight, mainly around my waist, but none on my butt. I hungrily watched the last piece of bacon disappear into Joe’s mouth.

“Ready to start?” Joe said, with his mouth full of bacon. Last summer the heater core in his car had sprung a leak. Rather than replacing the core in 95 degree heat, I had bypassed it between the thermostat and water pump so cooland could still circulate in the engine. With November weather in the air, it was high time to get the heater working.

“Did you get the parts?” I asked.

“Naw,” he said, “I was waiting for you. When I buy the parts by myself, you always complain that I got the wrong ones, so if wrong parts are bought, it’ll be your fault.”

“Okay,” I said, “pull your car over to the side of the driveway, and open the hood. We’ll let it cool off while we take my car to the parts store.” I looked over Joe’s car, and made a shopping list and we headed off to get the parts.

When we were in the car, Joe turned to me and said, “That was some party last night, wasn’t it?” I just grunted. “You were the foxiest girl there. If I didn’t know, I would have hit on you,” he added. “Of course, Becky was keeping an eye on you.”

Not enough, I thought. I remembered his patting and squeezing my behind, along with his hand reaching in the slit of my skirt and pulling on my garter straps. He had hit on me, but now was not the time to mention it.

By the time we returned from the parts store, the weather had warmed up, so I took off my sweat shirt so I wouldn’t get any grease on it. Because working on a car can be dirty work, I had put on an old and rather tight t-shirt which had already had grease and grime stains on it from previous forays into auto repair. Likewise for my jeans.

I started by draining the antifreeze into a clean drain pan. To do this I had to get on the ground and open the drain cock on the radiator, after which I started removing the old heater core and hoses. Some of this involves climbing under the dash board. Thankfully Joe’s car did not have air conditioning. All this activity caused my jeans to slide down a bit, but I ignored it and didn’t pull them back up, reluctant to add more grease to my jeans or dirt on the panties I was wearing, because by this time my hands were grimy.

I then turned to removing the by-pass I had put on last summer. This involved bending over the fender and stretching my arms out. It isn’t hard to figure out what happened next. The waistband of my panties were very visible. I felt Joe pull on the waistband and let it snap back. “Nice panties,” he said with a chuckle.

“If you don’t like the way I’m dressed, you can fix your own car,” I said in a huff.

“No, No, I do like the way you’re dressed,” he said. Just then Becky walked up the drive and heard Joe’s last comment.

“You like what?” she said, joining in the exchange.

“How Roy’s, or maybe I should say Renee’s, panties look,” he said to Becky.

“Let me see!” she said with a gleeful smile, and she walked up to me and pulled up my t-shirt. “Very nice,” she said. “So a little bit of your Renee side decided to get up on a Saturday morning.”

Renee never slept, I thought to myself.

It took the best part of an hour to do the whole job and at last I was squatting down to close the drain on the radiator before replacing the antifreeze. Squatting down is a sure way to display underwear, and this was no exception.

“Hey Joe, I talked to Sue, and she should be here any minute,” Becky said, “Maybe we can do something today.” As she said this Sue walked up the drive. My back was to her and I didn’t notice her arrival until I heard her say, “Nice panties.” Oh great, I thought sarcastically, why don’t we invite the whole block to come over and see my panties?

“He, or maybe I should say ‘she’ likes to wear panties,” Joe said with a laugh.

“No, I wear them because Joe likes cheap thrills,” I said.

“How come Joe’s all clean and you’re all dirty?” Sue asked.

“Because I’m doing all the work. Joe’s only here to pay for the parts and to admire my panties. I think he’d like to wear a pair,” I said. “How about it Joe? I can find a nice pair for you, and you can pick the color.” Joe began to blush. Maybe there’s something there, I thought.

“Joe, start your car and let it get hot so we can check for leaks,” I told him. Like I said, I’m a fairly good mechanic and there were no leaks. When the engine was hot enough to open the thermostat, the welcome flow of hot air came out of the vents on the dashboard. Another good job, I thought.

Just about this time my mother stepped out of the kitchen. “Hey, it’s way past lunch time,” she announced, “If you want, I can fix you lunch, at least for three of you. The grimy one will have to wait until he’s cleaned up.” Becky, Sue and Joe went into the kitchen, while I went to the wash tubs in the basement, where I had a goodly supply of industrial strength hand cleaner. The best way for me to do this is to first strip down to my underwear, or in this case, my panties, otherwise you can clean you hands, only to get them dirty again when you remove grimy and greasy clothes. I threw my jeans and t-shirt in the washer, poured in a good quantity of soap, and started it. I finally got all of the grime and grease off of my body, and was ready to go up stairs for a well needed shower, to get the rid of the hand cleaner residue. Oops, I thought, I have to go through the kitchen to go upstairs, and all I have on are my pink lace trimmed panties. I looked for anything to use to cover up, but finding nothing I decided to brave it. There were a lot of giggles and laughter when I stepped into the kitchen.

“You smell like industrial cleaner,” my mother said, “and your face, hands and arms are all red with that cleaner. After you take your shower, use some of my skin lotion.”

“Okay,” I said. When I passed Joe, I wiggled my panty clad behind at Joe. I don’t know why I did, it must have come from my Renee side. After a good hot shower, I dried myself by patting, not rubbing, and used the lotion. It’s awfully girly smelling, I thought, but I used it anyway. I wrapped my damp hair in a towel, turban style and got dressed.

When I got back to the kitchen, my mother handed me a salad. I needed something more than a salad, and I frowned at her. “Your figure, dear,” she said. Everyone, except for me, giggled and laughed at my discomfort.

Becky moved closer and sniffed. “Wow,” she commented, “You smell great, all flowery.”

What could I do? I just smiled and said, “Thanks.”

Becky, Sue, Joe and I spent the rest of the afternoon riding around in Joe’s car, giving it a long test drive, with stops here and there. We hit some fast food joints and I was finally able to get some substantial food. We started the test drive with Joe driving and my riding in the front passenger seat. We ended up with Joe and Sue in front, with Becky and me cuddling in the back.

About 5:30 Becky reminded us that she had a babysitting job that evening, and we all went to our respective homes.

Sunday, November 2, 2014:

Becky called and annouced that some of the stores in the mall were taking applications for extra holiday help. “I’m going over there,” she said, “We’re both 16 so we are legal for a job. Want to come along with?”

“I heard that it’s a bad idea for two teenagers to be with each other on a job search. Maybe you should go alone,” I suggested.

“But I want Renee with me,” she said, “that way you can browse the merchandise without calling attention to you while I talk with the hiring people.”

“Okay,” I said, “give me 45 minutes to an hour, and I’ll come over and pick you up,” I said.

“Great,” she said, “and dress nicely. Pantyhose, bra, nice blouse, and maybe the plaid skirt. Bring your makeup, and maybe I can do something with your hair.”

About an hour and a half, two well dressed young ladies headed off to the mall, one seeking a holiday job, the other just along for support.

It seemed that a lot of other people had the same idea, and about two hours and two stops at the washrooms, we found ourselves at a quieter part of the mall, but with no job. We noticed two unique stores. One was a corset shop and the other a women’s store for tall women.

“I didn’t know that anyone still wore corsets,” commented Becky. The other store actually had a ‘holiday help wanted’ sign in the window. We went in the store for tall women.

A tall woman approached us. “May I help you, girls?” she asked.

“I want to apply for the job,” Becky said, pointing to the sign in the window.

“We only stock clothes for women over five-eight. How tall are you?”

“Five-seven,” Becky replied, “but I can wear heels.”

“That may be true, but the clothes are cut for taller women, and you’d be on your feet all day. Not a good idea.”

The woman then looked long and hard at me. “How tall are you, Honey?”

“Going on five-nine,” I answered.

She took my hand and studied my nails. The repairs on Joe’s car had talken their toll.

“What in heavens happened to your hands?” she exclaimed.

“I was repairing a friend’s car yesterday,” I replied. “I just didn’t want to put on a set of acrylics, since I’m not the one looking for a job.”

“But if I hire you, your auto repair days are over,” the tall woman said. “Are you interested in a job? It seems that the current crop of females are all short.”

During this exchange Becky was smiling excitedly.

“Come into my office,” the tall woman said. Once in the office she introduced herself as Marge Shay, the owner of the store. Becky and I introduced ourselves. She invited us to sit.

“Before we go any further, I have to tell you that in addition to our women customers, we have our ‘special’ customers.”

I got the drift of what she said. “You mean cross-dressers?” I said.

“Yes, and if that bothers you in the least, I’m sorry, I can’t use you.” Both Becky and I laughed at this statement.

“What’s so funny about that?” she demanded.

“Well, I have a secret, and once you know it you might not want to hire me,” I said.

“Show her your IDs,” Becky suggested, and I did.

Ms. Shay took them and when she had noticed that my name was Roy, and that I was genetically a male, a broad smile crossed her face. “Excellent! All the more reason to hire you she declared, When can you start?”

“You mean I have the job?” I asked, not quite believing what I had heard, “But I was not looking for a job.”

“Maybe not, but a job just found you. You are exactly what I am looking for. When the men hear about you, and how good you look, they’ll be crowding through the doors. How do you manage to look so feminine?”

Becky and I explained the research and essays we had written. “Once I started getting in touch with my feminine side, that side no longer just touched; it grabbed on wholeheartedly.”

“I can’t pay a lot hourly, but I can give you a 60% discount on anything in the store, and you get commissions on your sales. Still interested?”

“Yes,” I answered, “but I am concerned about Becky getting a job.”

“Becky helped you in your transformation, right?”

“Yes, I couldn’t have done it without her.”

“I’ll tell you what,” Ms. Shay said, “let’s all three of us walk over to the corset shop.
A lot of my customers also shop there, if you get my meaning.” We did.

Ms. Shay introduced us to Mrs. Sands, who owned the corset shop, and explained our situation. Mrs. Sands smiled approvingly. “What do you know about foundation garments?” she asked Becky.

“Unfortunately, very little,” Becky admitted.

“Then lets corset up your friend, and you’ll learn a lot. How does that sound? What I like is that you’ve already dressed a boy, so our male customers won’t offend you.”

“Okay, I guess,” Becky said uncertainly.

“Go into the fitting room, and strip down to your panties.” Mrs. Sands commanded me to do, “You are wearing panties, I presume?”

“Of course, pink with lace trim,” Becky answered for me.

“Very fetching, I’m sure,” Mrs. Sands said.

For the next hour, I was fitted into a series of foundation garments, each one more painful than the previous one.

“Pick out one that you like,” Ms. Shay said. “I’d like you to wear it when you are at work. I’ll advance the cost and put it on your clothing account at my store.”

“60% off, Mrs. Sands, as usual” Ms. Shay asked.

“Naturally,” Mrs. Sands replied with a smile.

“Both stores get busy at Thanksgiving, and stay busy through the new year. Can you work evenings and weekends through the first of the year?” We both assured that we could, as long as it didn’t interfere with our school work.

I was still wearing my foundation garment when Becky and I rode home. “It really makes you look good,” Becky said.

After dropping Becky off I drove home. The first person I saw was my mother, who stared at me with surprise. “You look different,” she commented, “what’s going on?”

“Becky and I have jobs for the holiday season,” I answered, and explained out jobs.

After I finished, with a lot of questions from my mother, she finally said, “What will your father think?”

Thursday, November 6, 2014:

After Mrs. Benson said that she was sending Becky’s and my essays to a college professor, I more or less put the matter out of my mind. Imagine my surprise when she called Becky and Me into her office. With her was a distinguished man who was the professor to whom the essays had been sent. He started out praising our work, calling it original. Then he got to the point.

“I don’t know about your college plans, but I want you to at least consider choosing a college or university that has either a women’s studies major or a gender studies major. You both seem to have an aptitude for this area.”

When we talked some more, I disclosed that I was dressing as a female and working at a store that specialized in catering to the transgender community.

“Excellent!” he said, “might I suggest that you maintain your journal and note your observations. It may become a valuable tool for you and others to use. Naturally you won’t use names and you’ll keep it anonymous. When you are looking at colleges, could you have Mrs. Benson apprized of your progress? I’d really like to keep in contact with both of you.”

Saturday, November 8, 2014:

It was a gloomy and rainy Saturday afternoon, and I was in my room practicing different makeup looks. I heard a knock on the door and my mother ask to come in. There I was, fully dressed. She looked at me with a critical eye. “Too much dark eyeshadow,” she observed. We looked at each other for a few moments. “Time to talk with your Father,” she added, “less makeup is better in this case.”

“Okay,” I said, and removed my eye makeup and reapplied it under my Mother’s gaze.

“Better,” she commented. “Let me look at you first.” I stood up and turned aroung for her. “Okay,” she said, “Let’s go downstairs,” and with that she gave my hand a squeeze.

Dad was sitting on the couch, reading a magazine. When he heard us, he looked up. “Why are you dressed like that?” he asked, “I thought you were done with it.”

I paused a moment, and ignored his question. “Remember that I told you last Sunday that I had a seasonal job at the mall?”

“Yeah, I’m really happy for you getting a job.” he responded, “So?”

“I didn’t tell you where I’ll be working or what I’ll be doing.”

“Yeah, you kind of omitted any details.”

“Well when Becky and I went to the mall, only Becky was looking for a job. I was just there for support. Well, there’s this store that specializes in clothes for tall women; taller than 5' 8. Well, Becky is too short, but when the lady who owns the store saw me, she said I was tall enough.”

“So, what does this mean? When you were there, you weren’t, uh, dressed up like a girl, were you?” Dad said.

“Well, to be blunt, I was,” I said. “You see, it just worked out better, Becky wanted me to, so when she was talking to the employment people I could pretend to browse, and not call attention to myself,” I added.

“I’ll bet that’s not how things worked out,” he said with a slight smile.

“There’s something else,” I said, “the store has what the owner calls ‘special customers.”

“Special customers?” he asked.

There was no way to hint around until he knew what I was trying to say, so I went directly to the point. “Men who dress in women’s clothes. As you can suspect a lot of them are taller than most women, so, since the store caters to people who are taller, they like to shop there. As you can see, I’m a prime example.”

“Does the store owner know that your birth name is Roy?”

“That came out, and once she knew it, she told me that I was hired. I’m a sales clerk.”

“So, you’ll help other men look like women?”

“I’ll wait on anyone who comes into the store, but the owner thinks that because I am male, it will help sales.”

“I can see that,” Dad said, “if you wait on the men, they’ll be less embarassed.”

“Precisely,” I rejoined.

“Then what you wear will be more or less like a work uniform,” he observed.

“I’m glad you see it that way,” I said.

He frowned. “I may see it, but I don’t like my son prancing around in women’s clothes.”

“Is it okay if I promise not to prance?”

Dad laughed at this. I was making progress. “I have always encouraged you to make your own decisions, and I’ve always told you that your mother and I will support you. If this is what you’ve decided to do, I don’t have to like it, but I won’t prevent it. Remember, I’ll always love you, no matter what.”

“Thank you,” I said, “that means a lot to me.”

Nothing was said for a few moments. Then my father asked, “What about Becky? Does she know? How does she feel about this?”

I decided to answer all three question at once. “Becky was with me when I got the job. She seems very happy about it. By the way there’s a corset shop nearby and she got a job there.”

“A corset shop?” my dad questioned, “I didn’t think there were any of those left.”

“Just remember ‘special customers’ and you’ll understand.”

“I do,” he said and smiled.

A concerned look then crossed his face. “What you’re doing may be dangerous. A lot of people might want to physically harm you. Have you figured out how to protect yourself?”

“Becky and I are aware of the problems and are working on them. If it gets too difficult, I can quit,” I explained. Dad, Mother and I then spent the next hour discussing potential problems and how to avoid them. I felt that I was ready. My Renee side was very happy.

Finally, my father asked me, “Do you feel that you are really a girl? You don’t have to answer that right away, but think about, and we’ll talk about it later.”

Monday, November 10, 2014:

I had Monday off, and Joe came over to study for a test we both had on Tuesday. “I heard about your and Becky’s jobs. Weird!”

“Maybe, but I’m earning money, that’s more than you can say.” I replied.

“You know, you look different. Becky says that’s because you’re always wearing a corset,” he said.

“Yeah, all the time, except when I’m in school. If I don’t it’s uncomfortable when I have to put one on again,” I responded.

Joe was staring at me. “Are you wearing one now?”

“Yes.”

“Can I see?”

“Why do you always ask that? What is your fascination with women’s underwear? Sometimes I think that you want to wear some. Do you?”

“Well, umm,” Joe answered.

“Okay, just this once I’ll show you, but if I do, you have to wear panties, not just now, but all day tomorrow.” I figured this would be a deal breaker.

Imagine my surprize when Joe said, “Okay.”

“Go into the bathroom and put these on,” I commanded, and I handed him a frilly sky blue panty. When you come back, suitably attired, I’ll play show and tell.”

I had felt a bit tarty that morning and under my skirt and blouse I was wearing a full length corset with a built in bra, and I had nylons attached to the suspender straps of the corset. Naturally, I was wearing lace trimmed panties. Since my skirt was not lined, I was wearing a half slip. I had taken off my skirt and blouse when Joe walked back in. I couldn’t know if he was wearing the panties because he had put his jeans and shirt back on.

“Okay,” He said, “let me see.”

“Not until I see the panties,” I answered. “Strip!”

He took off his jeans and shirt, and there he was, wearing the panties. Well, I had made a deal, so I took off my slip.

“Wow,” he said. “I want to touch.”

I could see that he was getting excited. “Okay,” my Renee side answered.

When Joe touched me it was a feeling I had never experienced before. My Renee side was loving it.

And then he kissed me.

That surprised me and I quickly stepped back. “Why did you do that?” I demanded to know.

“I’ve wanted to kiss you for a long time. Now just seemed like a good time for it,” he said.

We just stared at each other for a few moments, my body tense with surprise. “I didn’t mean to shock you,” he said as he gently touched my cheek with his fingers. I visibly relaxed.

My thoughts were running wild. My Renee side was doing cartwheels.

“You liked it, didn’t you?” he said.

I didn’t want to admit it, but I did, or at least my Renee side did. “My mother’s home,” I said, “maybe we better stop this.”

“Okay, maybe later.”

I changed the subject and said, “You like wearing panties, don’t you?”

“I do,” he answered.

“Would you like to go with the whole look? Completely dressed as a girl?”

“I think so.”

“Okay, we’ll look for a time when no one will disturb us,” I said.

It was just about the time when Joe was getting ready to leave for home. “You know, I really appreciate all the help you’ve given me with school work and my car. I’d like to make it up to you by paying for a movie and pizza on Saturday night,” he said.

“Does that include Becky?” I asked.

“I heard that Becky has a babysitting job on Saturday,” he answered.

“If not Becky, then who else?” I asked.

“No one.”

“You mean just you and me?”

“Yeah.”

“You know, two guys going to a movie with each other, and pizza afterwards might give the wrong impression to some people,” I said.

“It wouldn’t if you went as Renee,” he said.

“Now let me get this straight,” I said, “You want to go out on a date with me, as Renee? Is that about it? I’ll be your girlfriend?”

“Yeah, that’s about it,” he answered.

“Why?” I asked.

“I’ve been attracted to you, at least your Renee side, Remember, we already have kissed each other.” he said.

“That was a mistake,” I said.

“I don’t think so,” he replied.

“Well, no matter what, the answer is ‘No’,” I said.

“Don’t be so quick to say No. Think about it.” he replied.

“Okay, I’ll think about it, but don’t get your hopes up,” I said. With that he picked up his backpack with one hand and gently brushed my cheek with the other. Renee desperately wanted to kiss him, but resisted the temptation.

“Enough,” I said, “now go!”

Tuesday, November 11, 2014:

After a restless night, thinking of what had happened between Joe and me, I caught up with Becky at lunch. First order of business was to confirm what Joe had said. “Are you busy on Saturday night?” I asked her.

“Yeah, I agreed to babysit. Why do you ask?” she said.

“Something came up, is all, but since you are busy, it doesn’t matter,” I said. “However, I do need to talk with you about something else. Could I give you a ride home and talk in the car?”

“Sure,” she answered, “It’s not something terrible, is it?”

“Naw, it’s something that’s bothering me, and I need to talk with you,” I answered.

“Okay, I’ll meet you at your car at the end of classes,” she said.

She was waiting at my car when I walked out of school. I opened her door and she got in.

Once I was in the car, she said, “Okay, what is it?”

“Joe,” I answered.

“He’s not in trouble, is he?”

“No, nothing like that,” I answered.

“Okay, then what?”

“I think that he’s attracted to me, as in boy to girl,” I responded.

“Is that all?” she laughed. “For those who know you and Joe, that is no secret. What, did he kiss you?”

“Well, yes,” I said, “but that’s not it. He asked me for a date on Saturday. Me, in this case, meaning Renee.”

Becky began to softly laugh. “It’s not funny,” I said.

“Yes, as a matter of fact it is,” she said. “All of the girls noticed that he couldn’t keep his hands off of you at the Halloween party. They wanted to know if it was also true when you aren’t wearing a skirt. So, has he?”

“Yes, but only when he sees that I’m wearing panties under my clothes,” I confessed, “He also told me that he now wears panties every day, except for days when he has PE.”

Becky snickered and said, “It sounds like he has gender issues, as Mrs. Benson would say.”

“But if I go out with him, people could say the same thing about me,” I complained.

“If that’s all there is to it, just tell him no,” She paused. “But that’s not all there is to it, isn’t it. You’d like to know what it’s like for a girl to go on a date, isn’t it?”

“Well, maybe, I’m just not sure. You’re my best friend, and I like to think of you as my girlfriend,” I said.

“And you think that our friendship would end if you went on a date as a girl? Is that it?” she said.

“Well, that certainly is an important part of it,” I said. Becky paused to collect her thoughts.

“Well, first of all, I am pleased and flattered that you consider our relationship to be so important to you,” she said, and with that she gave me a long kiss, which I returned with delight. “However, we need to remember that you getting in touch with your feminine side started with that essay, and I have to remember that I encouraged you to do so and actually did a lot to help it along. You can’t stop examining that side. I’m sure that you have wondered what it would be like if you were a girl on a date with a guy. So there is only one way to satisfy your curiosity, and that is to go on a date with Joe.”

“So, it’s okay?” I said.

“Yes, as long as you and Joe keep your hands, and other body parts, where they belong.” she said. “By the way, after the date I want details,” she added with a smile. “The date is on Saturday night, right?” she asked. “Come by my house on Saturday afternoon and I’ll help you get ready.”

Wednesday, November 12, 2014

The next day Joe caught up with me as we walked to our cars after school. “Well, what’s your answer, sweetheart?” he asked.

I quickly looked around to see if anyone could have heard what Joe said. “Don’t call me that,” I said.

“Okay, I won’t. But what is your answer?” Joe said.

“Okay, I’ll go on a date with you,” I said, “but only this once, and you have to behave yourself as a gentleman. No untoward touching, and no kissing.”

“The same goes for you. But remember, if you start anything, beware of the consequences,” he said. “I’m so happy, I want to kiss you,” he added.

“Not the best of ideas in the school parking lot,” I said, and with that we both got into our cars.

Saturday, November 15, 2014:

When I awoke on Saturday morning, I began to plan my day. The big problems were what I would tell my parents, and how I could avoid my parents when I got home, since I would most likely be wearing a skirt. My first step towards a solution would be to buy a little suitcase for all of my girl clothes and makeup. This was easily accomplished. While I was out shopping I also bought some makeup cleaning wipes, a hairbrush, some cold cream, and a roll of paper towels. While at the checkout line I noticed that there was a display of condoms nearby, and I impulsively bought some. I had no reason to do so, since I had no plan where they would be used.

A further stop yielded some feminine pads and a nice purse with a shoulder strap. I did indulge myself and bought a scarf.

Back at my house, I set aside some panties, stockings and my garter belt, which I could wear under my boy’s clothes. I carefully packed what other feminine clothes I had in the suitcase, along with my other purchases. My plan was to drive to Becky’s, get dressed with Becky’s help, put all of the clothes which I was not wearing in the suitcase and leave it in my car. Joe would pick me up at Becky’s house. I planned to have Joe drop me off at my car, and I would change into my boy clothes in the car, and remove all of my makeup before I drove home.

That afternoon I drove to Becky’s house to start my date. I had prepared a cover story for her parents which turned out to be totally unnecessary, since Becky had told her parents the complete story of what was going to happen.

“So, another walk on the wild side,” Becky’s father said to me. “I guess that your initial research didn’t include being a girl on a date with a boy. I can see why that would be important. By the way, are you still keeping a journal?” I confirmed that I was doing so.

“You may not know it, but most fathers give their daughters sound advice before her first date. You wouldn’t know it because you are a boy. But in this case, you are a girl, so I’m going to assume the role of a father. First, if there are any problems, you call for help. Second, don’t let things get out of hand. Boys will lie like a rug to get what the want from you. You just have to be firm and make sure they behave themselves. Now, go get ready, have a good time, and I expect a report from you.”

Becky’s mom asked me about how I was going to change out of my girl clothes and into my boy clothes, and I explained my plan.

“Since there is no secret here, bring your clothes in here and change back to Roy here,” she said, “now let’s get you ready for your date.”

I didn’t have that much to bring in, but I laid it out on the bed. “I’m wearing my corset, panties, garter belt and hose that I wore as Queen of the Night,” I said, as I removed my jeans and sweatshirt.

“Then you’ll need a dark skirt and top to cover the black underthings,” Becky said. “I have a dark green box pleated skirt and green blouse which you may borrow.”

“Thanks,” I said. “Oh,” I added, “I have your wig, and would like to wear that.”

“Sure,” Becky’s mom said.

We must have done a good job, because Joe was dutifully impressed. “You look wonderful,” he said when he first saw me. As he came closer to me he could smell my perfume. “You even smell wonderful,” he added.

Joe took my hand as we walked to his car. I could feel the breeze under my skirt. It was such a girly feeling, and Renee approved of it.

When we entered the theater, Joe kept my hand in his and steered us to the back of the theater. Joe sat in an aisle seat with me to his right. He kept my hand in his for a while. He then put his right arm around my shoulder and gently pulled me closer to him. I was enjoying this and rested my head on his shoulder.

Then I felt his left hand on my knee. “Stop that,” I hissed. He moved his hand away, but only for a while. His hand returned to my knee and began to slide up under the hem of my skirt. I had to admit to myself that it felt good, and after a few moments I took my left had and moved his had to the armrest of his seat. “Enough,” I whispered. He, however, kept hold of my hand, and shortly thereafter he had put my hand in his lap.

I jerked my hand away, and in a reproving voice whispered, “Any more of your antics, and I’m marching out of the theater and taking a taxi home.”

Joe was dutifully chastised and refrained from any more untoward touching, but only if I kissed him. I admitted to myself that I actually liked it when he touched me, but I realized that if I hadn’t stopped him things could very quickly get out of control.

As Joe drove to Becky’s house after first stopping off for pizza, he said to me, “I liked our date. How about you?” I just mumbled a response.

Joe pulled the car to the side of the street about a block from Becky’s house. “How about a kiss? Otherwise I’ll plant a big one on your luscious lips when I walk you to Becky’s door.” His threat worked, and we kissed. Frankly, I loved it.

Becky was home from her babysitting job when I walked through the door. We went to her room so I could change back to being Roy, during which time I gave Becky a full report.

Roy And The Road To Renee - Chapter 5

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

Other Keywords: 

  • Beautiful dresses

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 5.
By Pentatonic

Saturday, November 22, 2014:

I woke up at 7:00. Today was my first day at the store. I had used hair remover and taken a shower the night before. I could smell the lotion I had used. It was flowery, and I liked it. A few minutes later my Mother knocked on my door. “Are you up?” she asked. “If you need any help, just call.”

“Okay, Mom,” I replied.

I took off my nightgown and put on my favorite bra with inserts and panties. While the corset was uncomfortable, it was a necessity, and I pulled the straps under my panties. Since I was wearing the corset, I could use nylon stockings, as opposed to pantyhose. I put on a full slip, and started with my makeup. I had found a nice sleeveless blue dress with a flared skirt, which I thought was just right for my first day of work. It was then that I asked my mother for help with my hair.

My Mother looked me over. “It might get cold, so you might want a sweater,” she suggested. She then handed me a brand new purse. “A new job deserves a new purse.” she said.

Today was also Becky’s first day, so we arranged that I would drive.

Although the store didn’t open until 10:00, I arrived at 8:45. Ms. Shay greeted me at the door, and she showed me around the store and the merchandise. “I’ll have you follow me around today, and you can see how things are done.” Some of the other clerks started later and worked until closing.

It was about 5:30 when Ms. Shay said to me, “That’s one of my sepcial customers.”

The special customer related that she was going clubbing that night and needed to wear something to “Knock them dead,” as she put it. Mrs. Shay introduced me as a new seasonal employee.

The customer began to browse the racks and I carried clothes back and forth to the changing room. It was about 6:15 when Mrs. Shay turned to me and said, “It’s after your quitting time, so if you want to leave, you may.”

“No, I’d rather stay for this sale,” I said.

“Good girl, that’s the spirit I want.”

At last the customer picked out an outfirt with a very tight short skirt. Personally, I thought it looked awful, because it emphasized her narrow hips and lack of behind. I must have frowned, because the customer looked at me and asked, “You don’t like it, do you honey?”

I looked over to Ms. Shay who smiled and nodded at me. She must have had the same idea.

“It looks okay, but I think that we could find something that would go better with your figure,” I said cautiously.

“Okay, honey, find something for me that works with my figure,”

“The top is great,” I said as I pulled out a differents skirt. “Why don’t you try this on. This skirt is fuller, and with it you can swirl and the skirt will flare out a bit. It’ll drive them wild.”

She changed into the skirt I had selected and did a swirl in front of the mirror. “You’re right,” she said, “I’ll take it,” Ms. Shay looked happy.

As her parcels were being wrapped, the customer turned to me and said, “Any other ideas?”

“No, not right now.” I answered.

The customer was now examining me very closely. “Are you . . .” she started, and then said, “No,” to herself.

“Am I what?” I asked.

“I don’t want to embarrass you, but I thought that you might be transgendered or a transvestite, but I see that I was wrong. Please let me apologize.”

“No need to apologize,” I said, “I am.”

Ms. Shay, the customer and I were very happy. It appeared that on my first day I had my own client customer.

Thursday, November 27, 2014:

While the Christmas season officially started on Thanksgiving Day, I had spent several days and evenings before then working at the store with Mrs.Shaw, so I would be prepared for the Thanksgiving weekend. Mrs. Shaw scheduled me for 5:00 to closing, but said that if I could get there earlier it would be great.

My family was having Thanksgiving dinner at my Aunt Brenda and Uncle Lou’s house, and to accommodate my job, dinner would be at 1:00. I figured that I could drive back home after dinner and change into my ‘work clothes,’ meaning a pretty dark green dress. I had purchased the dress at the store and couldn’t wait to wear it. It was a classic A-line design, sleeveless and with a scoop neck. The hem was about two inches above my knees. I also bought a cheap imitation pearl necklace which went with the scoop neck,

I decided to wear my panties, corset and hose under my Roy clothes, supposedly to save time, but in truth because I liked wearing them. While so attired, my mother knocked at my door, and came in. “I know that you plan on coming back here to get dressed for work, but maybe you should bring your clothes with you in the event that you can get dressed at your aunt’s house.” she said.

I was putting my work clothes out on the bed, with my mother providing commentary on what would go with what. I then packed all of my clothes in my Renee suitcase, with the exception of my new dress, which I left on a hanger. “Get finished dressing, and we’ll put your clothes in your car, and we can head off,” she said.

We arrived at my Aunt’s house at about ten, and my mother joined the ladies in the kitchen, while my uncles and male cousins were sprawled in front of the television, watching football. I am not a big fan of football, so I followed my mother and sister into the kitchen. “Why don’t you kids go down to the rec room, and leave us some space in the kitchen,” suggested Aunt Brenda. So all of my female cousins, my sister and I went downstairs.

When we had all sat down, my sister said, “Roy, here has a job for the Christmas season. Why don’t you tell all your cousins about it?”

“Well, I’m a sales clerk at a clothing store in the mall,” I said.

“Oh, come on, they want details,” my sister said.

“I don’t think they do; it’s all rather boring,” I responded.

“Okay, then, tell them what clothes you have to wear to work. Girls always find that interesting,” my sister said.

I made some vague noises.

“Do you have trouble remembering? Can I help you? Does the word ‘A-line’ help you?’ my sister said.

The word ‘A-line’ caught everyones’ attention. “You mean A-line as is a dress or skirt?” a cousin asked.

“Precisely!” exclaimed my sister, as I began to turn shades of red from embarrassment. After that nothing would do but to relate the whole story from the time the essay was assigned. “So, after dinner, I’m going back home to put on my dress and go to work,” I concluded.

“Too bad you couldn’t dress here. We’d love to see how you do it.” another cousin said.

“But we can,” my sister said, “she brought all of her clothes with her in case she could do her transformation here. Renee, get your things out of your car.”

When I came back in I hung my dress and slip on a hook on the closet door, and put my suitcase on the bed. My cousins all felt the fabric of the dress and admired its style. I opened the suitcase and removed my battery operated makeup mirror, my makeup kit, my wig, my bra, breast forms, and shoes.

I decided that my parents aunts and uncles might not want to see me dressed, so I kept on my Roy clothes over my corset, panties and hose for dinner.

The food was delicious, and I was looking forward to overeating. As I was about to take an additional piece of turkey, I caught my mother’s eye. She was frowning and shook her head. I withdrew my hand and my mother smiled. My cousin Judy caught this exchange and looked questioningly at my mother.

“He’s got to watch his figure,” my mother volunteered.

Judy, knowing what was going on, just snickered.

Under my mother’s watchful eye I did get a piece of pumpkin pie, but it was tiny. No whipped cream.

After dinner the men retired to the television and their wives repaired to the kitchen. As my mother went with them, she said, “You better get ready for work.” Naturally, my cousins made it plain that they wanted to help me.

Not withstanding my cousins’ ‘help’ I managed to get dressed and put on my wig and makeup. Sneaking out of the house without my aunts and uncles seeing me was a bit of a task but with my cousins’ help, I was successful.

Thursday, December 4, 2014:

When I arrived at the store on Thursday evening, Mrs. Shay was pushing a wheeled rack around the store and filling it with dresses.

“I’m putting these on sale. Forty percent off,” she said, “they’re last year’s stock or older, and I need to make room for new clothes.”

I noticed that one of the dresses was a sleeveless sweet fit-and-flare dress which had illusion mesh detailing at the hem of the skirt with a jewel neckline and an A-line silhouette. It appeared to hit at knee. Most interesting was that it was my size.

Ms. Shay noted my interest. “That’s a good dress for dancing,” she said, “do you want to try it on?”

I nodded my head. “Go ahead.” she said.

I took it back to the changing rooms, and found it fit me perfectly. I came out of the changing room and gave it a twirl.

“It looks darling on you,” exclaimed Ms. Shay. I smiled in return.

“If you wear it to work a few times over the next weeks, you can have it free.”

“Thank you,” I responded, “I will.”

“Keep it on today,” she suggested.

It caught the attention of quite a few customers which resulted in the sale of more dance dresses.

“Now all you have to do is get invited to a fancy dance, to wear it to,” Mrs. Shay commented.

Not likely, I thought.

Sunday, December 7, 2014:

The next Sunday afternoon Becky, Joe and Sue were meeting at my house for a study session. Becky mentioned that the youth group at her church was having a Christmas party on Saturday, and we were all invited.

“What time” I asked.

“7:00," she said.

“I scheduled to work until 7:00, so I don’t think I can make it. By the time I close out my shift, go home and change, I’ll be late.”

“Why don’t you just come directly from work?” Sue asked.

I gave Sue a funny look, and said, “You know where I work and the clothes I wear to work, that’s why.”

“It’s not like we haven’t seen you in a dress before,” Sue rejoined, “Remember Halloween?”

“That’s different. It was a costume, and I wore a wig for disguise,” I answered.

“But you have to admit it was a dress,” Joe blurted out. I gave him a dirty look in return.

“Are you going to give us that old excuse that you have nothing to wear?” asked Becky.

“No,” I answered, “Ms. Shay gave me this darling dance dress.” I instantly regretted what I had said.

“Can we see it?” Sue asked.

“Put it on,” added Becky.

“Yeah,” added Joe, “we all want to see it.”

I should have just refused, but my Renee side wouldn’t let me. I really liked wearing that dress.

“Okay, you win,” I said and went upstairs to put on the dress. It wasn’t all that difficult. I was already wearing nylons, panties and my corset under my boy clothes, so I just had to put on a bra and breast forms, a slip and the dress. I also put on some low heels.

My Renee side then took over. I looked in the mirror and gave my hair a brush. At the last moment I applied some likstick and a little mascara and headed back downstairs.

“Gorgeous!” exclaimed Sue.

“Sue’s right,” added Becky, “Give us a twirl,” Which I did.

“Definitely kissable,” was Joe’s comment. I just gave him a dirty look.

“You have to wear it to the party,” said Becky.

“I agree,” said Sue.

“Me too,” Joe added. “I can’t wait to dance with you.”

“I’m not sure,” I said, “Maybe I just won’t go to the party. Some of the kids there may not be as enthusiastic as you all are about me wearing a dress.”

“Come over to my house before work on Saturday, and I’ll get you all dolled up, and maybe add the wig,” Becky said.

Saturday, December 13, 2014:

After Becky’s careful ministrations, I arrived at work.

“Wow,” said Mrs. Shay, “You look great. What’s the occasion?”

“I’m going to a Christmas party at Becky’s Church, and I won’t have time to go home and change after I’m finished with my shift here.”

“Now there’s dedication to the job, if I ever saw it,” she said with a big smile.

The party was going at full swing when I arrived. “I was afraid you’d chicken out,” Becky said.

“I feel badly that I can’t dance with you,” I said to Becky, “you know, they might frown on two girls dancing,”

“Hardly,” Becky said. “Most boys are too shy to ask a girl to dance, so a lot of the time girls have to dance with other girls. Just look around.” I did and there were a lot of girls dancing with other girls.

“But you won’t have that problem,” Joe said, “because I’m going to dance with you.”

Joe then took my hand and we started dancing. The first dance was a fast one, and Joe took the opprtunity to twirl me so fast that my skirt flared out giving everyone a good view of my hose tops and garter straps. This caught a lot of peoples’ attention.

Most of the boys were congregated around the refreshments. Finally one separated from the pack, walked over to me and asked me to dance. I hesitated.

“Go on,” urged Becky, and he and I went to dance.

“I don’t want to seem forward,” he said to me while we were dancing, “but you are the prettiest girl here, and the best dressed. Howcome the other girls aren’t dressed as well?”

“Well, I have a part time job at a women’s dress store, so I have to dress like this for work, and I came here directly from work. Oh, and I get a discount for all the clothes I buy there.”

The next song the DJ played was a slow dance. Joe grabbed my hand and pulled me to the dance floor. It was a waltz, but it was clear that Joe was not experienced with waltzes, and his lead was non-existent. Finally, in frustration, I said, “Let me lead.”

“Okay,” he challenged, “but what makes you the super dancer?”

“When I was younger, my sister wanted to take dance classes. Most of the students were girls, so they were strongly encouraged to bring a boy,” I said, “and therefore, I learned to dance. However, I only learned to boy steps.”

By the end of the evening I was tired and my feet hurt. Therefore I took the girls home and headed home myself.

Thursday, December 25, 2014:

After opening gifts at home in the morning, the whole family headed over to one of my cousin’s house for Christmas dinner. After a month of wearing the blasted corset, I was dressed all male. Not one stitch of female attire anywhere.

“You still working at that women’s clothes store?” one of my cousins asked.

“Yeah, until the first of the year,” I answered.

“Then how come you’re not wearing a skirt or dress?”

“I’m taking a break from it. Anyway, I don’t think my aunts or uncles would approve.”

“Well, maybe,” another cousin added, “but they all know.”

“Knowing is one thing,” I answered, “having it displayed is another.”

“We were hoping to play dress up” a third one said.

“Go ahead, don’t let stop you, just count me out.”

“But dressing you up is most of the fun.”

“Sorry to spoil your day,” I said.

“But are you wearing panties?”

“No,” I repoled with emphasis. My cousins and even my sister looked crestfallen.

“Look, its bad enough that I have to dress up for work,” I said in explaination,

“But you let us dress you up on Thanksgiving,” Cousin Natalie said.

“That was different,” I said, “Remember, I went directly to work after the dinner and I really didn’t need your help getting dressed.”

“But you wore dresses and skirts other than for work,” my Sister chimed in, “remember Halloween?”

“But that was a costume,” I rejoined.

“Some costume,” she said, “Wait, I have pictures on my phone,” and with that she pulled them up for all of my cousins to see.

“Nice dress.” my Cousin Sandy commented, “you’re showing a lot of leg.” She looked more. “You’re wearing stockings and garters. In my opinion that’s more than a mere costume.”

“That was Becky’s idea,” I said.

“So you let your girlfrient dress you up, but not us?” Cousin Rachael added.

“It was all part of a bet,” I said, and with that I went downstairs to be with my Uncles and male cousins.

Tuesday, December 30, 2014:

Joe stopped by the house to tell me that the park district was holding ballroom dancing classes on Mondays, starting on January 5th. “I thought about what you said about learning how to dance. I’d like to sign up for the classes, and maybe you would like to also?”

“Sounds like fun,” I replied, “Why not?”

“Well, they only want couples. The slots for singles have already been filled.”

“We can ask Becky and Sue, they might be interested.”

“That’s not what I had in mind,” he responded, “I was thinking about just you and me.”

“I don’t think that the park district wants two boys dancing with each other,” I replied.

“I think that you’re right,” he answered, “I was thinking of Renee.”

“No way!” I asserted, “when my job at the store is over, it’s back to good old Roy, 24/7.”

“What about all the clothes you have for Renee?”

“I haven’t thought about that,” I said, “maybe I’ll give them to you and you can be Josephine.”

“Look,” Joe said, “at the Christmas Party you said that you didn’t know the girl’s steps. This is a chance for you to learn.”

“It’s a skill that I’ll never need,” I responded, “so the answer is no.”

Wednesday, December 31, 2014:

I was working in the back room of the store helping a ‘special customer’ find an evening gown when I heard Ms. Shay call me. “There are some girls to see you.”

I walked out of the back room to see my cousins standing there with foolish looking grins on their faces. It being New Year’s Eve, the store had a special on evening clothes and Ms. Shay had asked me to model an evening gown. I had put my hair up in a french twist, and was wearing nighttime makeup. The gown itself had a scoop neck, three-quarter flutter sleeves, high/low scalloped cuffs, Sheer yokes and sleeves, straight illusion neckline, darted bust, a left side slit, column silhouette, and allover floral guipure lace. It also had a concealed back zip with hook-and-eye closure, and was partially lined. The night before, Ms. Shay had asked me to wear white or ivory underclothes and shoes or sandals. Ms. Shay also provided me with a half slip. I knew that I looked good.

I knew why they were there, to see me wearing a dress.

“Aren’t you a little short for what we sell in the store?” I asked them, a little unkindly.

“We’re here to see you and maybe share a snack during your break,” Rachael said.

“We’re really busy today, and I’m hardly dressed for a visit to the food court. I look like I never made it home last night, dressed as I am,” I retorted

“But you do look gorgeous,” Cousin Natalie said.

Ms. Shay was watching this exchange with a bemused expression on her face. “She’s right, you do look gorgeous, and you’ve been working hard. Why don’t you go with your cousins. Oh, by the way, I have some signs advertising our evening gown sale, so you could sit by one of the signs and attract business?”

“I’m helping a customer find a gown, so you girls will have to wait until I’m done.”

“That’s okay,” Natalie said.

My customer bought two gowns, and Ms. Shay smiled broadly when I rang up the sale. “I only wish there were more clerks like you,” the customer said with a smile, “I wish I could look as good as you.”

I smiled back.

After the customer left, my Cousins and I headed for the food court. Quite a few shoppers stared at me.

“Was that customer really a man wearing women’s clothes?” Sandy asked.

“A ‘special customer’ is what we call them,” I said.

“Do they know about you?” Natalie enquired,

“Yes, we don’t deny it. That’s one of the reasons they like the store.”

“Do they ever hit on you?”

“Yeah, but I tell them that I’m only sixteen and that puts an end to it.”

We found a table next to one of the signs advertising the evening gown sale. Quite a few women noticed and asked me to stand and turn around to get a better look. It obviously impressed them, because when we returned to the store it was crowded with a lot of those same women looking at the gowns.

“You caused a sensation,” Ms. Shay said, “Maybe I should send you back to the food court to drum up some more business.” which she did. She even gave me money for food for my cousins and me.

It was a very busy day, and Ms. Shay was obviously delighted with the money taken in. After we closed the doors, I headed to the back room to change out of the gown. Ms. Shay came in the back room and said, “I want you to keep the gown and slip. You earned them.”

“But it’s an expensive gown,” I said.

“Well, maybe, but a customer ripped open a seam while trying it on. I had it repaired, but I didn’t put it back on the racks. I thought of you and decided to ask you to wear it today. The interest and sales you brought in by wearing it paid for the gown many times over.”

I decided to not change out of the gown for the drive home, but before I left the store I called Becky to wish her a happy new year.

“Why don’t you stop over on your way home. My folks are hosting a New Year Eve party, and I’d like to have you with me.”

“Well, I’m still Renee, if that’s okay with you.”

“It’s okay with me.”

“And I’m wearing an evening gown.”

“Even the better. You’ll fit right in. The party is supposed to be formal.”

“Let me call my Parents and tell them where I will be and not to expect me home until after midnight.”

Shortly thereafter I arrived at Becky’s house. Mr. Jones answered the door when I rang. The look on his face was priceless. “Renee?” he stammered. “Come on in.”

“Good evening, Mr. Jones,” I said with a smile.

He helped me with my coat, and then called out, “Betty, you’ve got to come downstairs and see this.”

When Becky’s Mother saw me, she said, “You are absolutely stunning. How did you do it? You only called a short time ago.”

“Mrs. Shay had me model this gown today at the store, and when we closed, she gave me this as a present. I decided to wear it home, and then Becky invited me over.”

“Well, you’ll fit right in, and you are a very welcome addition to the party. Now, if you’ll excuse me, I have to finish getting beautiful. I don’t want my daughter’s boyfriend outdoing me,” she said with a smile.

I turned to Becky. She was wearing a lime green party dress, with chiffon over the top and skirt. Her hair and makeup were beautiful, and she seemed to glow, “Becky,” I said, “you are gorgeous.”

She smiled and said, “Thank you, and so are you.”

Mr. Jones turned to me, and said, “I hope you’re still keeping up your journal.”

“I am.”

“Good”

Mr. Jones looked at his watch. “The other guests should be arriving in about fourty-five minutes. Maybe you two can help with getting the food ready.”

Becky and I went into the kitchen. No one else was there. Becky turned to me and put her arms around my neck and kissed me. I responded by putting my arms around her and kissed here. We stood there a few moments looking into each other’s eyes, and kissed again. I could feel her breast against my arm, and moved my hand to cup it. She didn’t move away or move my hand, but rather made a soft moaning sound as I gently massaged her breast.

We reluctantly broke off the embrace and looked at each other with fondness. She smiled and said, “You need to fix your lipstick.”

“Look who’s talking,” I responded, “so do you.” We both began to giggle and she took my hand and led me to the powder room. She closed and locked the door, and we kissed again. Finally we repaired our lipsticks, and proceeded to the front door where our assignment was to greet the guests and take their coats.

Most of the men were wearing tuxedos and the women were wearing party dresses or formal gowns.

I opened the door when the bell rang. Outside were two men, both wearing tuxedos. To my surprise, they were holding hands as they walked in. To my further surprise, I recognized one of them as a ‘special customer’ from the store.

One of the men, a Mr. Thompson, was a co-worker of Mr. Jones, and he introduced his friend, a Mr. Stevens. Becky’s Father introduced us as “My Daughter Becky and her friend Renee.”

It was then that I noted a flicker of recognition in Mr. Stevens’ eyes, which went as quickly as it had came.

It was later that Mr. Stevens came over to me. “When I first saw you, you looked familar, but I couldn’t place you. Just now it came to me. By any chance do you work in a tall girls shop in the mall?”

“Yes,” I answered, “I am a seasonal employee, until this Friday.”

“Ms. Shay told me that she had a cross-dressing employee for the holidays. Might that be you?”

“Yes,” I softly confessed.

“And Becky’s Parents know?”

“Yes, they do,” I answered,

“And are you Becky’s boyfriend?”

“Yes.”

“And they don’t mind?”

“No.”

He smiled and said, “If I knew there would be another cross dresser here, I might have been tempted to wear a gown like yours, except that I could never look anywhere as good as you do,”

“Thank you,” I responded.

“If you don’t mind, I’d love to hear your story how you came to be here tonight.”

“It’s a long story, and it all started with Becky and I working together on an essay on gender issues.”

“Before we go further, I think that both of us should agree to keep our conversation confidential, for both of our sakes,” he said.

“I wholeheartedly agree,” I said, and I related the story, after which he rejoined Mr. Thompson.

Shortly after midnight, I excused myself and headed home. My parents were waiting up for me, and as can be exptected, they wanted all of the details of why I was wearing an evening gown. After relating tbe events of the day and evening, my sister arrived home. She was dumbstruck when she saw me. I realized that I should have changed into my pajamas when I first arrived home, but I hadn’t.

My sister finally regained her compouser and voice. “My brother in an evening gown! I’ve got to hear all about this. Were you at a formal New Years Eve party, or is this how you like to lounge around the house?”

“How about tomorrow? I’m tired and want to go to bed.”

“On one condition,” she said, “If you let me borrow that gown. It had to cost at least $250.”

“Okay,” I answered, “but it didn’t cost me anything.” With that I went upstairs to bed.

Roy And The Road To Renee - Chapter 6

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Sweet / Sentimental

Other Keywords: 

  • Dancing Sisterhood

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 6.
By Pentatonic

Thursday, January 1, 2015:

A weak January sun was shining through my bedroom window when I awoke at about 9:00. From my position in my bed I could see that I had hung up the evening gown, but the rest of my clothes from yesterday were just dumped on a chair. I patted my hair. It was still in what remained of the french twist from yesterday. I got out of bed and put a robe on over my pajamas and headed to the bathroom. A quick glimpse into the mirror revealed that I had done a poor job removing my makeup when I went to bed. I took down what was left of the french twist and with some cold cream and tissues I attacked my face, only to find that yesterday’s makeup was resisting removal. During this procedure my stomach began growling.

Ignoring my stomach I got in the shower and let the hot water play over my hair, face and body. I stepped out of the shower, dried myself and put my robe back on. I replayed the events of yesterday in my mind and it was then that I realized that I needed to put on something under my robe.

I went back into my bedroom and realized that all of my boy underwear was ready to be washed. I scolded myself for ignoring my laundry. In desperation I grabbed a pair of sky blue panties from the drawer. So clad, I went to the kitchen to get some food.

Shortly after I started eating, my sister Amy entered the kitchen. She examined my face. “Still some traces of makeup, I see,” she said. She then noticed my hands. I had totally forgotten to remove my nail polish. She pointed at my hands and began to snicker. I got up and retrieved some nail polish remover. When I stood up, my robe opened enough to reveal my sky blue panties. “Nice panties,” she said with a snicker.

I ignored her and began removing the nail polish, after which I started a load of laundry so I wouldn’t have to wear the panties all day.

I returned to the kitchen and my sister was still there, nursing a cup of tea. She turned to me and said, “I’m still waiting,”

“For what?”

“You telling me what happened yesterday. You promised to tell me today.”

“It was nothing,” I started to say.

“That eveining gown could hardly be considered ‘nothing.’”

“Well, you see, Ms. Shay was having a special on evening wear, and she asked me to wear the gown while at the store.” I omitted mentioning anything about the forays to the food court. “It had to be repaired after a customer blew out a seam trying to get into it. At the end of the day, Ms. Shay gave it to me. Then I called Becky, and she invited me to her house. Her parents were having a New Year Eve party, and it was formal, so I didn’t change out of it.”

“Your story is lacking details, but don’t worry, I’ll get them out of you sooner or later.”

At this point our mother entered the kitchen. “I hope you two remembered that we’re hosting the New Year dinner for my family, so I need you to help get ready for the dinner.” With that she handed each of us a list of things to be done. “Remember, our guests will be arriving at about 4:00,” she added, and with that she breezed out of the kitchen.

I went back upstairs and diligently removed all of the remaining traces of makeup and put the contents of my chair in a laundry bag and tossed it into the back of my closet, to be dealt with later.

I then attacked my list and also completed my laundry, I carefully put my clean clothes in the drawers, covering my Renee clothes as well as I could. I had worked up a bit of a sweat while doing all of this, so I decided another shower was in order.

I put the blue panties in the bag with all of my clothes from yesterday, and got dressed, completely in Roy clothes. It was shortly thereafter that my aunts, uncles and cousins arrived.

My female cousins and my sister repaired to her room, supposedly to watch a ‘chic flic,’ but it was only a few minutes later that my sister asked me to join them “just for a few minutes.”

I had a bad feeling about this, but I complied with her request. When I arrived in her room, there was no chic flic on the screen.

It was a picture of me, in my evening gown in the food court. All of the girls were giggling with abandon.

“You didn’t tell me about this part,” my sister said accusingly.

“I didn’t think it was important,” I mumbled.

“Important? It’s vitally important,” my sister exclaimed, “sit yourpretty little butt down and give us all of the details.”

I felt like I was a defendant on trial, with my sister as prosecutor and my cousins as the jury, and not an unbiased jury.

“Before we start, are you still wearing those darling blue panties you had on at breakfast?”

“No,” I answered. I decided monosyllable answers would be best.

“Why not?”

“I donno.”

“Wrong answer, and as a penalty we should make you put them back on.”

I decided to change the topic. “Where did that picture come from?”

“I took it,” cousin Sandy said, and she held up her cell phone, “You were just too gorgeous not to.”

“Show the one with the slit,” Natalie requested, and immediately a picture appeared with my left leg coming out of the slit. My stocking top was visible.

“Stockings and garters,” Cousin Rachael interjected, “very sexy.”

I was totally humiliated. I stood up and said, “I’ve had enough, I’m leaving,” and I started toward the door.

“Stop,” my sister commanded, “we’re not finished until we see the actual dress. Where have you secreted it?”

I remained silent.

“Probably in her closet,” Natalie suggested, and they all headed for my room. Once there, my sister opened my closet door, and there, in full display, was the gown. They all examined it, until their attention was drawn to my other girl clothes. Before anything more could happen, my mother announced that dinner was being served.

While we were eating my Uncle Ralph pointed his fork at me, while chewing a piece of ham with his mouth open. “You still sashaying around in a dress like some fairy?” I never liked my Uncle Ralph. I didn’t answer his question.

“Ralph, leave it alone,” my mother, who is his sister, commanded.

“Pervert.” he said as a closing comment.

“Excuse me,” I said as I left the table and went to my room, crying all the way.

In a while my sister quietly entered my room, sat next to me on the bed and gave me a hug. “I’m sorry for what happened,” she said.

“It’s not your fault,” I said between sobs.

“Maybe not, but I am sorry if we humiliated you about your cross dressing.”

“Okay,” I said, but it was not okay.

“Oh, your cousins and I are very proud that you can show your feminine side, We all love you dearly, and hate to see you hurt.”

“Thank you,” I sobbed, “and I love all of you.”

“There is something else you should know,” she said.

“What?” I said cautiously.

“You are absolutely one hot babe in that gown.”

This brought a smile to my face between tears, “Thank you,” I managed to say. My sister having come to comfort me awakened a feeling of sisterhood with Amy.

It was one of the least successful holiday dinners for my family. My Mother was angry with her brother. My dad supported my Mother . My Uncle’s wife was embarrassed by her husband’s inconsiderate outburst, and my other aunts and uncles were uncomfortable with what had happened.

Friday, January 2, 2015:

The next day was my last day at the store. I wore a high waisted box pleated skirt made from printed fabric and a beige long sleeved nylon blouse with ruffles down the front. Ms. Shay smiled when she first saw me. “What a great outfit,” she said, “of course it has to be because it came from this store.”

Ms. Shay then took me aside. “Your holiday employment ends today. I want you to know I am really impressed how well you did. I think that you’ll be really pleased with your commission check,” which she then handed to me. I was very, very pleased.

“If you can, I’d like you to work just before Valentine’s day. I’ll give you a call in a month.”

When I came home that evening, my parents were waiting for me. We talked about my employment, and they were quite impressed with the amount of money I had earned. Then they got down to what they really wanted to talk about my Uncle Ralph and my crossdressing.

“I’m really sorry that my brother acted like he did,” my Mother said.

“It’s not your fault,” I replied.

“I know, but It still bothers me.”

“It’s uncle Ralph who should be sorry, but I bet he’s not,” I said, “but there is one positive note from the unpleasant scene.”

“What’s that?” my dad asked.

“When Amy came upstairs to comfot me. I felt closer to her than I ever did before. Like two sisters.”

The conversation then turned to my cross dressing. “Now that your job is over, are we going to get Roy back full time?” my Dad asked.

“Well. . .” I said, “there’s the dance lessons that Joe signed up for at the park district. They start on Monday evening. Sue can’t make the first lesson, so I’m kind of filling in as his dance partner for that lesson. After that, Sue will do the rest. And then Ms. Shay might want me to work a few evenings before Vaentine’s day.”

“Oh.” he said.

“And then there’s Amy. She kind of hinted that she might want me to go with her to the mall, because I’m prettier than her, to attract boys.”

“According to . . ?”

“Amy,” I interjected, “You can just ask her. It was her idea.”

“You like dressing up as a girl, don’t you?” my father asked.

“Sort of.”

“Your mother and I would like you to see a counselor about any possible gender issues you might have. Is that okay with you?”

“I guess,” I responded. Refusing to do so would cause family problems which I did not want to address.

“I’ll see about making an appointment for us,” my mother said. “Any questions?”

“Yeah, find out how the counselor wants me to dress for this session.”

Saturday, January 3. 2015:

It was snowing hard when I woke up on Saturday morning, and one glance out of the window revealed that it had been snowing hard most of the previous night. I put on my robe over my pajamas and headed for the kitchen for some breakfast. It wasn’t too much later that Amy joined me at the table, after first giving me a hug.

She sat down and said, “Mom told me what you said,”

“And what was that?”

“How when I was comforting you that you felt closer to me than any time before.”

“Oh, that,” I responded, “it’s true.”

“And it’s so sweet.” and with that she took hold of my hand. “It’s almost like I gained a sister,” she added.

“You have, and her name is Renee,” I confessed. “Renee is now part of me all the time, and comes out from time to time, especially when I’m wearing a skirt or dress.”

“So it was Renee who was working at the store?”

“Yes,” I answered, “but on New Years Day, Renee was in control when you came to my room, even if I wasn’t dressed.”

I decided to change the topic. “Did Mom tell you that she and Dad want me to go to counseling?”

“No, why?”

“Something about me liking to wear dresses and skirts, I suppose.”

“What’s wrong with that? You look really cute when you wear them.”

“I don’t really know, but it seems to be bothering them.”

At that point, our mother entered the kitchen. “Are you going to lounge around like that all day?”

“What’s wrong with that?” Amy said.

“Well, your Father and I are going to visit his Mother today, and one or both of you should clear the snow off the walks and driveway.”

“Are you sure it’s safe to drive?” I asked.

“If we didn’t go, Grandma would be so disappointed, and your dad said it should be okay. The plows are out.”

“Okay, let me get dressed and I’ll shovel the drive before you go,” and with that I headed upstairs to ge dressed.

Right after my parents left, Joe pulled into the now clear driveway. “I thought that we could go around and clear driveways and sidewalks in the neighborhood for some cash,” he said, “What were you two thinking about doing?”

“Maybe practicing some dancing,” Amy said.

“Maybe so, but those aren’t exactly dancing shoes,” I said, pointing to Joe’s feet.

“Neither are what you have on your feet,” he observed.

“But I have proper footwear here, and you don’t,” I answered.

“We might be able to find a pair of shoes for Joe,” Amy said.

“But he’d have to wear pantyhose or nylons for them to fit,” I said to Amy.

We actually got some dancing, after which Joe and I went around the neighborhood and shoveled. When we were done I realized that it was a lot harder than working at the store.

We were all in the kitchen when my parents called and said that it was too dangerous to drive home until the roads were cleared, and that they would stay at Grandma’s and would see us on Sunday.

We decided that Joe should spend the night at our house and we spent the evening playing dress up, which included getting Joe entirely en femme and wearing the Queen of the Night dress.

Finally it was time to go to bed. “I don’t have a spare set of clean pajamas for you,” I told Joe, “but I have a clean nightgown if you don’t mind it.”

“I’ll wear a nightgown if you will,” he said.

It ended up with all of us wearing nightgowns. My Renee side liked it, a lot.

Sunday, January 4, 2015:

We could hear snowplows working all night, and in the morning the snow had stopped and Joe and I cleared the drive and walks. After that we went to Joe’s house and did the same.

With Joe safely at home, Amy asked, “Did you and Joe do you-know-what?”

I could only guess at what ‘you-know-what’ was, but since neither Joe nor I had done anything except give each other a good night kiss and sleep, I could truthfully say we hadn’t.

It was now safe to drive and Amy’s boyfriend came over to the house. After a few hints from Amy, I decided to go to Becky’s house so I put on my corset, bra, panties, and stockings, over which I put on a pair of jeans. I also put on a uni-sex bulky sweater, my own snow boots and took a long skirt, a feminine parka and my cosmetics and went to visit Becky.

“I need a pair of feminine boots for snow,” I told Becky when I arrived. “Maybe we could run over to the mall and I could buy a pair.”

“Won’t it look odd for a boy buying girl’s boots?” she asked.

“It won’t take but a minute for me to do my hair and makeup and change into this skirt. Underneath, I’m all girl.” While we hugged and kissed I felt her hand slide under the rear of my jeans to make sure I was wearing panties. “I approve,” she said.

It took longer than a minute, but about a half an hour later two girls headed or the mall, My Renee side was very happy.

In the privacy of the car I related my experiences starting with the disastrous New Year’s dinner, and told her that my parents wanted me to go to counseling.

“What kind of counseling?” she asked.

“I really don’t know, maybe gender counseling,” I answered.

“Or, heaven forbid, counseling to ‘make my son stop wearing girl’s clothes’,” she said.

“There is one other new thing that happened as a result of the dinner,” I said, “my relationship with my sister has changed.”

“In what way?” Becky asked.

“We are more like sisters now. Even my mother noticed this,” I said.

“Then maybe you really are a girl underneath it all.”

“Does that bother you?”

“I have to think that out,” she said, “if you are really a girl, then we would be lesbians.”

“But we haven’t done anything, lesbian or heterosexual. We’re both too young.”

“Until this spring,” she said. I could only wonder what she meant by that.

Monday, January 5, 2015:

As befitting the first day back at school after the Christmas break, the weather was gloomy. There was a lot of snow on the ground, so I called Becky and offered her a ride to school, which she gladly accepted. On the ride to school, I asked her what she meant about spring.

“We both turn seventeen,” she answered.

“So? What’s the big deal about that?”

“Age of consent,” she replied.

Now I knew about the age of consent from sex education classes. Was this an invitation?

Most of the classes were tedious. Some of the teachers had assigned reading to be done during the Christmas break. It was obvious that most of the students hadn’t even started the required reading. A collective sigh of relief could be heard when the final bell rang.

Becky, Joe and I walked out of school together. “You haven’t forgotten about tonight, have you?” he asked me.

“No, I remembered.”

“Remembered what?” Becky asked.

“Joe signed up for dance lessons and I’m going with him,” I answered.

“Aren’t dance lessons usually boy girl kind of things?” she asked.

“Well, Yeah....” Joe started to say.

“And let me guess, you’re going as Renee,” Becky said to me.

No answer was needed

“Isn’t that going to cause some problems at your house,?” she continued.

“Yeah, but I’ll figure something out.”

“Why don’t you bring your stuff to my house, get dressed there and then pick up Joe? You could do the reverse after the class,” Becky suggested.

“That’s a great idea,” I said, “Thanks,”

I put on my underthings at home and took the sleeveless sweet fit-and-flare dress which I had bought at the store last December. Becky liked the dress.

I put my hair in a french twist, and applied some makeup. I had my heels in a bag and wore my snow boots. I then went to pick up Joe.

The instructors had a dance studio downtown and were husband and wife by the names of George and Phyllis. Aside from Phyllis, I was the only one wearing a dress. Most of the other students were wearing jeans. A lot of them were wearing rubber soled shoes, which I knew were not good for ballroom dancing. I caught George looking at my snow boots with a frown. I held up the bag which contained my heels and his frown turned into a smile of approval.

The class started with a waltz, and George and Phyllis demonstrated the box step. I had my left hand on Joe’s shoulder with his right hand on my back. Our other hands were clasped together and out to the side. The box step was no problem, since we had practised it before.

“I’m going to d a twirl, so be ready for it,” I said to Joe. A few measures later I raised my right arm and Joe’s left arm. I pushed away and sideways with my left hand and Joe pushed me to my right, all on the first beat of the measure, I went under our raised arms and twirled on the second beat, and returned to our previous position of the third beat. Naturally, when I twirled my skirt flared out. I imagined that those who were looking could see my garter straps. We twirled a few more times, and George and Phyllis indeed did notice. At the end of the song, George said, “It seems that you two have done some waltzing before tonight.” George then paired me up with one of the boys and paired Joe up with one of the girls. George and Phyllis did the same.

During a break, the instructors came over to talk to us. George was holding the class roster in his hand. “Are you Sue?” he asked after consulting the roster.

“No, I’m Renee,” I answered, “Sue is Joe’s girlfriend, but she couldn’t make it tonight, so I’m filling in for this session. You’ll see her next week.”

“We’ll miss you,” George said, “you’re the only one who is properly dressed for dancing. Of course, theses classes are way below your level.”

I thanked him with a smile.

On the way home, I suddenly felt Joe’s left hand under my skirt and on my right thigh. “I’m driving and I don’t want to get in an accident, so stop that,” I commanded. “Anyway, what would Sue think about you doing that?” I added.

“She likes it,” Joe replied a little sheepishly.

“You know darn well that is not what I meant,” I exclaimed,” how would she feel if she knew you were two timing her, and with a boy, to boot?”

“I guess she wouldn’t like it,” he replied.

Wben I dropped Joe off at his house, I called Becky on my cell phone to tell her that I was on the way to her house and keep an eye out for me. I didn’t have to ring the bell before she opened the door and we went up toher room for me to change back.

Becky and I sat next to each other on the edge of her bed, and I related the events of the class. Becky then asked, “Did Joe try anything?”

“Yeah, he put his hand under my skirt and began rubbing my thigh.”

“Like this?” she asked and immediately put her hand under my skirt and rubbed my thigh. We pulled each other closer and started kissing in earnest, with her hand slowly moving up my thigh to my stocking tops.

Finally I said, “We better stop this before it goes too far.”

“Don’t you like it?” she said with a little hurt in her voice.

“I do like it, but one of your parents may come barging into the room.” With that her hurt turned to a smile.

She looked at my face. “Your lipstick is a mess,” she said.

“And so is yours. I’m taking off my makeup, but you better fix yours,” I said.

I made it home without event, took off and put away my feminine attire, and put on my pajamas. I climbed into bed and wondered what would have happened if I hadn’t stopped Joe or Becky, or both.

Roy And The Road To Renee - Chapter 7

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

Other Keywords: 

  • Counseling

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 7
By Pentatonic

Friday, January 9, 2015:

The prior Wednesday my mother told me that she had made an appointment with a counselor for Friday afternoon, and she handed me a note to give the school excusing me from my afternoon classes.

As I left for school on Friday morning, she said, “The appointment is for 1:30, so try to be home by 1:00.”

My friends were interested in what this was all about, but I had absolutely no clue. “My mother made the appointment but didn’t tell me anything,” I explained.

“Look, if when you get wherever you’re going, and you see men in white coats with a straight jacket, run like hell,” Joe suggested.

“Yeah, if they asked us, we’d have told them that you’re nuts, and save all the time and expense,” added Harry. They all got a good laugh out of this.

Joe pulled me aside, and quietly asked, “You don’t think that they’ll try to make you stop wearing skirts and dresses?”

“My dad might like that, but I just don’t know.”

At 1:00 sharp, my dad, my mother and I piled into my dad’s car. But not before my mother asked, “You’re not wearing panties under your clothes, are you?”

I hadn’t thought about doing that, so I assured her that I was not wearing panties. However, upon reflection, that didn’t seem to be such a bad idea. Too bad I hadn’t thought about doing that.

The counselor appeared to share the office space with other counselors or the like. There was a waiting room with cheap looking uncomfortable chairs. A receptionist or secretary sat behind a sliding glass window which looked over the waiting room. My mother announced that we were the Evans’ and had a 1:30 appointment with Dr. Devlin. The secretary, or what ever she was shoved a clipboard with a form thought the open side of the sliding glass window. “Fill this out and return it to me when you’re done.”

My parents and I sat down and my mother started attacking the form. When I suggested that since I was the subject of the counseling that I should fill it out, my mother scowled at me and kept filling in the form.

When she was finished, she returned it without me seeing what it said. About ten minutes later we were escorted to what I presumed was Dr. Devlin’s office/ There was a desk and executive looking chair on one wall, four other chairs, a coffee table and some end tables with lamps. The lighting was rather subdued. Dr. Devlin stood up as we entered and introduced herself. My mother handled the introductions for my family. Dr. Devlin was a rather tall and middle aged woman, not bad looking. She was wearing black court shoes, dark blue hose, and a dark blue dress with a white lab coat over it.

Her white lab coat made me think of Joe’s comments about the men in the white coats and straight jackets. I smiled at the thought. Dr. Devlin saw my smile and returned it. At her invitation we all sat down, with Mom on one side and Dad on the other.

Dr. Devlin turned to me and asked, “Why don’t we start by you telling us why you are here?”

“I have absolutely no idea,” I responded, “my parents made all of the arrangements and told me to come.” The Doctor look surprised with my response, and referred to the form on the clipboard.

“But it says right here . .”

“I never saw what was written on the clipboard,” I quickly interjected.

“Is that true?” Dr. Devlin asked my parents.

“Sort of,” my mother admitted, “we thought that Roy would know.”

“But he says he doesn’t.”

The Doctor turned to me, and referring to the form on the clipboard, she said, “It says that you like to wear female clothes and pretend to be a girl. Is that so?”

“I have dressed like a girl from time to time, but I don’t pretend to be anything other than what I am,” I asserted.

“When did this all start?”

“Last fall. I can give you an exact date if you wish. I, and all of the class, had to write an essay on sexual stereotypes and to imagine what it would be like if we were the opposite sex. My mother and Becky, my girlfriend, decided that I should have the experience first hand, and bought me some girl’s clothes to take a trip to the mall as a girl.”

“And how did that work out?”

“It was a real eye-opener. I learned a lot, and at Becky’s father’s suggestion I started keeping a journal. Becky and I then wrote our essays. We both got A’s.”

“I’d really like to see your journal and essay, if that’s alright with you.” the Doctor requested.

“Okay, sure,”I responded.

“So after your experiment, did you ever wear female clothes?”

“Yeah.”

“When was the last time you did?”

“Monday.”

“Like four days ago?” With this revelation my parents had strange looks on their faces. “What was the occasion?”

“Well, my friend Joe had signed up for ballroom dancing classes and his girlfriend couldn’t make the first session, so I went as her substitute. I went to my girlfriend’s house and got dressed there.”

“That may explain the surprised looks on you parents’ faces.,” the Doctor said.

“Yeah, I didn’t want them to know. I know that my dad doesn’t like me to dress as a girl.”

“Okay, the dance class. How did that go?”

“It was alright. I’m a pretty good dancer, and my sister helped me learn the girl’s steps.”

“So Becky and your sister know. How about Joe and your other friends?”

“They all know. I had to read my essay in class.” I volunteered.

“And they don’t have a problem with your cross dressing?”

“Since all of them are still my friends, I would say that it’s okay with them,” I said.

“Any times between last fall and this last Monday?”

“Yes,” I answered, and I related the stories of Halloween and my seasonal job as a girl. I had noted that the Doctor was frantically scribbling notes as I talked. “Everything I told you, and more, are in my journal, which I have kept up to date. I can let you see it, so you don’t have to write so much.”

“Thanks, that’s a great idea,” the Doctor said with a smile.

“Do you like wearing girl’s clothes?” the Doctor asked, changing the topic of our discussion.

“I do. It can be fun.” I answered, “at least most of the time.”

“Any problems?”

“One comes to mind,” and I related the events that happened at the New Year’s Day dinner, “The interesting part was that when this happened, I was wearing a coat and a tie. I was all ‘Roy’ at that time.”

“Did what happened bother you?”

“A lot.”

“Do you ever think that you really are a girl?”

“I don’t know. I like to be Roy, but I also like to be a girl some times. Most of the time I feel like a girl when I’m dressed as a girl, but otherwise, not. I feel like I have a Roy side and a Renee side. My Renee side is getting stronger.”

After some more discussions, the Doctor looked at her watch. “Well, our time is about up. How do you feel about coming back a week from today? You can bring your journal.”

She then turned to my parents. “I’d like Roy to have a complete physical and some blood tests. Let me write out what I want, and you can take it to Roy’s physician.”

After a quiet ride home, I went up to my room to be alone. However, I was home for about a half hour when my sister knocked on my door, and I let her in.

“So, sis, how did it go?” she asked.

“I’m not sure, but the Doctor seemed to be interested in my story. I’m going to give her a copy of my journal at the next session.”

“How did Mom and Dad take it?” she asked

“I don’t think they got what they wanted,” I answered.

“And that was what?”

“I think they wanted the counselor to make me stop dressing.”

“So, you’re not going to get rid of all of your skirts, tops and dresses?”

“At least for now,” I answered.

“So you’re not going to give them all to me?”

“We can share.” I said, and we gave each other hugs.

Friday, January 16, 2015:

I brought a copy of my journal to the next counseling session. Dr. Devlin was impressed. “Not only do you say what happened, but you also record your feelings. I’m looking forward to reading it.”

The discussions were a lot like the previous session and I brought up Renee. When the Doctor got into questions about sexual activities, she noted that both my parents and I were uncomfortable.

She then surprised me. “I’d like to have Renee at the next session, and just Renee.” She turned to my parents and addressed them. “Mr. and Mrs. Evans, I think it would be better if you did not attend the next session because otherwise it might make Roy uncomfortable.”

It was obvious that my parents were not happy with this, but at last they agreed.

When I got home, my sister was overjoyed with this news. “You have to pick out an outfit that is just right for the occasion. Are you going to let me help you?”

“Of course,” I said, “isn’t that what sisters are for?”

Friday, January 23, 2015:

I arose earlier than usual, and took a shower after first applying hair remover. I heard the bathroom door open and peeked around the shower curtain. It was Amy. “Isn’t this a little early for you?” I asked.

“Yeah, but I have to help my sister get dressed for the big day,” she answered. “I’ll see you in your room,” she added and left the bathroom.

When I walked into my room she was laying out lingerie and stockings for me. “You won’t have a lot of time to get dressed before the counseling session, so it may be a good idea to wear your Renee underclothes now, and cover them with some jeans and a baggy sweatshirt for school.”

I nodded my approval, and started with my nylons. While doing this the towel fell off. I caught my sister staring at my crotch, and I frowned at her. “Girls don’t mind seeing each other naked or partially dressed,” she said as if this explained everything. “Hasn’t Becky seen you naked?”

“No.”

“Too bad,” she replied.

Since I would need more time today, I decided to cut my last class. I could tell the teacher that my doctor’s appointment had been moved up, which I did.

Before school, Amy and I had decided that I should wear a gray A-line skirt. Because it was unlined, I would need a slip. We had chosen a long sleeved ivory blouse and a gray sweater. I knew that I was cutting it close, because of my hair, which I would put in a french twist and my makeup. I made it to my counselor’s office with a few minutes to spare.

I walked up to the sliding glass window, and told the secretary or receptionist, or whatever she was, that I had a 1:30 appointment with Dr. Devlin. She just looked at me with a vacant stare and consulted her appointment list. “You’re not on the list,” she said.

“Name’s Evans,” I said.

“There’s no girl named Evans on the list,” she challenged.

“I’m Roy Evans,” I explained. “Tell Dr. Devlin that I’m here.”

Still staring, she reluctantly got off of her chair, presumable to report that a girl named Roy was out front. It apparently worked because a minute later she opened the door and escorted me to Dr. Devlin’s office.

“Wow,” Dr. Devlin exclaimed when I entered her office. “You are beautiful. Have a seat.”

I smoothed my skirt under me and gracefully lowered myself to a chair and demurely crossed my ankles, keeping my knees together.

Dr. Devlin silently looked at me, and then asked, “Roy, if that really you?” I smiled. “I don’t see much of Roy here,” she added.

“I’ll take that as a compliment,” I responded.

“How do you do it?”

“Well, first of all there’s this uncomfortable corset.”

“Do you always wear a corset?”

“Only when I’m Renee.”

“Why do you wear it?”

“For my figure, and if I don’t my clothes won’t fit right. However, I’m also trying to lose some weight.”

“And?” she asked, looking for more.

“A lot of practice and a job at a women’s clothing store with a 60 percent discount. I’ve also had help. At first from my mother and Becky, and later from my sister and Becky.” I commented.

“As I’ve read in your journal. By the way your journal is very detailed and comprehensive, however, there is very little of any sexual activity noted in it. How come?”

“There hasn’t been any,” I said.

“Really?, Many girls your age have already engaged in sexual intercourse,” she commented, “And are you saying you haven’t?”

“I can’t very well have sexual intercourse as a girl, now can I?” I responded.

“Well, now that you mention it, you can’t” she said with a smile, “It’s just seeing you dressed as you are, it’s hard to imagine you as anything other than as an attractive girl.”

“Thank you, I try to look good,” I said.

“And you succeed. But a lot of boys your age have had sexual intercourse.” She noted.

“Or at least they claim to, A lot of them lie.”

“But you haven’t”

“No.”

“Why not?”

“I’m only sixteen. There’s this rumor going around that a sixteen year old guy and his sixteen year old girlfriend were caught doing it in the back seat of his car in a parking lot and that he may end up as a registered sex offender for the rest of his life. Scary, if it’s true, so I am dutifully scared of that and the further problem of the girl getting pregnant.” I explained.

“But how about just ‘fooling around’ a bit?” she suggested.

“It’s hard to stop once you begin to ‘fool around’ as you call it.” I answered.

“Is that from personal knowledge?” she asked.

“Sort of,” I answered, “at least it seems so with Becky. And then there’s Joe.”

“Joe?” she questioned with a bit of astonishment, “tell me about that.”

“Well” I started, “Joe likes it when I’m dressed as Renee. He likes to touch me. He convinced me to go on a date with him, which probably was a mistake, and at the movie he kept putting his hand up my skirt and rubbing my thigh. He even took my hand and put it on his thigh. If I hadn’t stopped him, I don’t know what would have happened if and when he got to my panties.”

“So why did you stop him?”

“Oh, come on!” I blurted out, “both of us are guys.”

“But when this happened, you were Renee, right?”

“Yean, but as I said, it probably was a mistake to do so on my part. He might have wanted me to have oral sex with him, and I wasn’t going to find out.”

“Do you think he’s a homosexual?”

“I don’t know,” I answered, “but I heard that his girl friend, Sue, wasn’t so reluctant.”

“Do you think that you might be homosexual?” she asked.

I thought for a moment, and then said, “I don’t think so, because I am really attracted to girls, especially Becky. However, when on the date with Joe, I wondered what it would be like to give him oral sex. Maybe I’m bi-sexual.”

“Maybe, and maybe you really want to be a girl.” she commented.

“I’m really messed up, aren’t I?” I questioned.

“No more than most teenagers,” she reassured me, “but your lack of sexual experience makes it difficult to come to any conclusions.”

“So you think I should go further in my relationship with Becky, and maybe with Joe?” I asked with some astonishment.

She sat up straighter, and pronounced, “As a mental healthcare professional I can’t recommend it.” She seemed to relax a bit and then said, “But. . .”

I took her meaning. “I understand,” I said.

“Good,” she said.

When the session was over I text massaged Becky and asked if she wanted a ride home from school. I signed it ‘Renee.’ She massaged back and said “Yes ;-)” I timed it so that I pulled into the parking lot just as Becky came out of the door. I wanted as few people to see me dressed as Renee as possible, since a lot of people also knew Roy’s car.

When she entered my car and saw me, she said, “Oh, la, la,” and leaned over the center console and kissed me. I pulled out of the parking lot but stopped a block away, and flipped down the visors to expose the vanity mirrors. “Lipstick,” was all I needed to say.

Naturally, I had to give a full report on the counseling session. “How did she like Renee?” Becky asked.

“She said I wouldn’t make first cut in an amateur drag queen competition,” I said, trying unsuccessfully to keep a straight face.

“She did not!” exclaimed Becky.

“She was really impressed,” I then answered, “she thought I looked good.”

“As you do.”

My mother had a part time job doing the books and payroll for a dental practice. Her hours were flexible, and some of the work she did could be done at home, but on this day she was working on the 2014 profit and loss statement and payroll tax reporting, so she didn’t expect to be done until at least 5:30. Since she wouldn’t have time to prepare supper, she and my dad were going out to dinner directly from her work. “Maybe you and Becky can do some studying and order a pizza for dinner,” she had told me when I dropped her off at the office that morning. She even gave me some money. As a result, Becky and I had the house to ourselves until at least 7:00, with the exception of my sister.

“Maybe Becky and I’ll catch a movie and stop for pizza afterwards,” I told my mother. That was okay with her.

My sister Amy had ridden home from school with her current boyfriend and had arrived at the house shortly after Becky and I did. “Hey, sis,” she said to me. “Got a minute? I need to talk with you,” Amy’s use of the word ‘sis’ caused momentary confusion to Becky until she remembered what had happened on New Year’s day.

Amy’s current Beau was a guy named Andy. “I don’t think that I want Andy to see Renee. Not only because he may not understand, but furthermore he might like you more than me,” she said with a smile.

“Okay, so how do you want to plan this?” I said, “Mom gave me money for a pizza, and Becky and I are going to study together until then. We’ll be in my room.”

“If you don’t mind. I’d like to invite Andy over for pizza, and after that we’re going out to see a movie,” Amy said. “ I’d like to be out of here before the parents come home.”

“And you’d like some private time together with Andy, too,” I commented,

“Yeah, that too,” she said.

“Okay, sounds like a plan. You leave Becky and me alone for our studying, and we’ll give you time with Andy.”

Amy stood for a minute looking at me. Finally she said, “You really look pretty. That’s a nice skirt you have on. If you weren’t wearing it I’d like to borrow it for my date.”

In response, I reached behind me and unzipped my skirt. I picked it up from where it had fallen in the floor and handed it to Amy. “Be my guest,” I said to her. “Remember, it’s unlined, so you’ll need a slip.” I took off my half slip and handed it to her. With that, Becky and I picked up our books and headed to my room.

Friday, January 30, 2015:

After a hurried session of getting ready, I attended this counseling session as Renee, which might have had something to do with what Dr. Devlin suggested. “I think that we should discuss your cross-dressing,” she said.

“Okay,” I said.

“You’ve done a lot of it since the fall. Do you like it?”

“Remember, most of the time I dressed in female clothes I was working in the store and I kind of had to dress as I did,” I observed.

“You make it seem that you found it unpleasant,” she said, “but I get this impression that you actually liked it. So, tell me, do you like wearing female clothes?”

“Yes,” I confessed.

“Do you feel like a girl when you do?”

“Sort of.”

“When you wear female clothes, do you feel an attraction to boys?”

“Well, maybe,” I answered.

“More than when you are dressed as Roy?”

“I guess so,” I said.

“Have you ever felt an attraction to boys when dressed as Roy?”

“Sometimes when I’m feeling girly, otherwise not.”

“If you could, without any adverse consequences, would you wear female clothes all the time?”

“Probably not,” I answered.

“Why not?”

“There are just some times when it’s more fun being a boy.”

The rest of the session followed the same lines. At the end of the session I suggested that I would like to see if my parents would allow me to be Renee whenever I liked. Dr. Devlin suggested that we could do that and that I should invite my parents to the next session.

As I had done the week before, I picked Becky up from school after my counseling session.

My mother would not be home that afternoon for the same reasons as before. It being the end of January, there were a plethora of year end tax returns to be filed, both state and federal, for the dental practice. This in addition to normal payroll, profit and loss statements, partners’ distribution of profits and allocation of operating expenses. This meant that she was working all day and my father was picking her up from work and taking her out to dinner. My parents were not expected to be home until after 7:00. She left some money for Amy and I to order a pizza or other take-out food.

“We both have to pick up our W-2 forms, so why don’t we head off to the mall? We can also look at clothes,” I said to Becky when we were in the car.

“And check out the boys,” Amy replied.

“Maybe for you,” I said, “but remember that you’re my girlfriend, and I’m not in the market for a boyfriend, no matter how I’m dressed.”

“With the way you’re dressed, you’ll have to fight them off,” Becky added, with a chuckle, and she reached over and slid her hand up my skirt. I reminded her that I had to pay attention to my driving, and she reluctantly removed her hand,

When we arrived at the mall, I called Amy and told her that I would not be home until 5:00. “Andy will be with me,” Amy warned, “so make sure that you and Becky don’t arrive any earlier.”

When Becky and I arrived at the tall girls store, Ms. Shay mentioned that she could use my help a few days before Valentine’s Day, and we worked out a schedule.

Becky and I arrived at my house at about 5:30, just in time to see Andy’s car back out of the driveway.

Friday, February 6, 2015:

When my parents and I, dressed as Roy, arrived for the counseling session, Dr. Devlin said, “Roy wants us to explore some issues. Roy, why don’t you start out the discussion.

I took a deep breath. “I know that you don’t like it when I’m dressed as Renee, but I’d like it if I could dress as Renee at home or whenever I want to.” My statement was greeted with silence from my parents.

Dr. Devlin finally broke the silence. “How do you feel about that?” she asked my parents.

“This Renee business has gone on much further than it should have,” my father answered, “I don’t like it and I surely don’t want to condone it.”

“It’s already caused problems with my family,” my mother interjected, and she related the disaster at the New Year’s dinner.

“How does your daughter feel about this?” Dr. Devlin asked my parents.

“You’d have to ask her,” my mother commented.

“I can answer that,” I said, “we’ve become more like sisters. She likes borrowing my clothes.”

“I’ve noticed that Amy has been dressing better,” my mother said, “now I know why.”

There was a pause in the conversation before I said, “I’m going to be working at the tall girl’s store for a few shifts before Valentine’s Day.”

“I guess that’s okay,” my father conceded, “at least he’ll be earning money.”

“Could we set some limits that everyone can agree on?” suggested Dr. Devlin.

I was making progress. I thought, and the rest of the session involved negotiations of when and where I could be Renee.

My father concluded the session by saying, “No dressing like a street walker, His mother or I have to approve of his clothes.”

Roy And The Road To Renee - Chapter 8

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Not Work-Safe
  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Gay Romance

TG Elements: 

  • CAUTION

Other Keywords: 

  • Pregnancy

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 8
By Pentatonic

Caution - this chapter contains explicit sexual material.

Saturday, February 14, 2015:

Sue, Joe, Becky and I attended the Valentine’s day dance. I wore my suit and Joe had on a sport coat. Both of us wore white shirts and dark ties. The girls had really gone all out. Sue had a red dress with the hem a few inches above her knees. Becky had borrowed my dance dress.

“I wish you were wearing that dress, it looked so good on you at the dance class,” Joe commented. I pretended to not hear him. He leaned closer to me and whispered, “Are you wearing panties under your clothes, sweetheart?”

I scowled at him, and said, “ Hardly.”

“Well I am, lover,” he confessed.

“What does Sue think about that?” I asked.

“She doesn’t know,” he answered, and then added, “Yet.”

“What’s it about you and female underwear?”

“I like the way it feels on me, and how it feels when I rub your behind,” he said with a leer. As if to prove his point, I felt his hand on my rear.

“Stop that!” I hissed. He withdrew his hand. Just at that time Sue and Becky rejoined us, after a potty break. I would have loved to hear what they said while they were in the washroom.

Becky and I traded off dances with Sue and Joe. While Joe and Sue were dancing a slow dance, I kept my eyes on Joe’s hands. I noted that he did not rub her behind. Did he reserve that for me? I wondered.

I had driven and Becky and I were in the front, separated by the counsole. Sue and Joe were in the back, enjoying each other’s company. Halfway on the way home, I heard Sue say, “Ooooh, panties.” I didn’t want to know how she made that discovery.

Saturday, March 14, 2015:

It was Joe’s seventeenth birthday. I had turned seventeen nine days before on the fifth. Joe’s parents threw an informal St. Patrick’s Day and birthday party for Joe. When I arrived, Joe said, “I had hoped that Renee would have attended.”

“You just can’t behave when Renee is arround,” I said.

“And what’s wrong with that?” he responded, “we’re both seventeen now.”

The import of what he said escaped me until I remembered ‘age of consent.’ Now I had an idea of the thoughts on his mind. I also recalled Dr. Devlin’s comment on my lack of sexual experience.

It was a nice party. There was pizza and the mandatory birthday cake. Joe had invited the usual crowd. Some of the furniture had been moved to allow dancing.

During the evening, Joe asked me to help him to bring in some more soft drinks. This was hardly a two person job, but Joe had ulterior motives. The soft drinks were outside, since it was cold enough out there to avoid using a refrigerator. Out in the dark, Joe put his hands on my shoulders, pulled me to him and kissed me. He then moved his hand down to my crotch, and with his other hand he grabbed my hand and put it on his crotch. He was aroused.

“Stop that!” I commanded.

“But it feels good, doesn’t it, honey?” It did, but I wasn’t about to admit it. He then moved his hands to my shoulders, again, and kissed me again. We then grabbed some soft drinks and rejoined the party.

I wouldn’t admit it, but Joe’s kisses were as enjoyable as Bercky’s. I wondered about my sexual orientation.

Sunday, March 15, 2015:

This being the Sunday before St. Patrick’s Day, there was a parade in the area, followed by various parties in the neighborhood. My parents had been invited to one such party. They weren’t expected to be home until after 9:00.

Becky and my sister Amy had been hired as babysitters for couples enjoying the festivities. Joe and I were not invited, and with a test scheduled for the next day, we needed to study. My mind wandered back to Joe’s birthday party and Dr. Devlin’s comment about my sexual inexperience.

In addition to the test, we were assigned to read a play for English class. Joe arrived at my house about 1:00. I could see the disappointment on Joe’s face when I met him at the door. “No Renee?” he questioned.

“You have trouble behaving yourself when I’m Renee,” I answered, “Anyway, we’re here to work on homework.” I did have a secret plan, however.

Joe then asked, “Hey, did you read that stupid play?” he said referring to the assignment for English class.

“Yes. Why?”

“I’m having some problems with it,” he answered.

“Let me guess,” I said, “you haven’t started reading it, have you?”

“Well, sort of,” he answered.

One thing I’ve noted is that plays are meant to be heard, not silently read. The play we were working on had a run time of about two and a half hours. When Joe arrived, I suggested that we read the play out loud, each of us taking different parts. I figured that we could be finished by about 4:00 and then start on our other studying.

We worked on the play for the first act when I suggested a break for some pop and snacks. When I returned from the kitchen, I asked, “Are you gay?”

Joe gave me a strange look, and blurted out, “What made you ask that?”

“Well, on more than one occasion, you kissed me, and you’ve tried to feel me up,” I responded.

“That wasn’t with you, that was with Renee,”

“ and with me as Roy,” I interjected. “Remember, I am Roy. No matter what I am wearing.” With that I went to the powder room and gave myself a spritz of my favorite perfume.

“I want you to close your eyes and keep them closed until I say you can open them,” I called out.

His eyes were closed when I walked back into the room. I walked over to him and said, “Stand up.” When he was standing I stood in front of him and put my hands on his shoulders. He sniffed the air and I knew he could smell my perfume. I leaned in to him and pulled him into contact with me and I kissed him. He hesitated for a moment and then kissed me back.

“Okay, you can open your eyes.” I said. He opened his eyes and looked into mine. “Now, kiss me again,” I commanded. He did, and our tongues darted in and out of each other’s mouth.

I was still holding him tightly when I said, “Not bad.”

“No, I guess it wasn’t,” he said, “but you tricked me with your perfume.”

“But I didn’t trick you when we kissed with our eyes open,” I countered. With that I kissed him again, and I felt his hands on my butt, pulling me close to him. I could feel that he was getting aroused. “Part of your body likes it,” I said, as I rubbed myself against him. I began to also get aroused. “You too,” he said, and he kissed me again. By now both of us were aroused.

I moved my hands down to his belt and loosened it. He reached down, unbuttoned his jeans, and unzipped his fly. His pants fell to the floor. He then pulled his underpants down.

Now was the moment of truth. Although I had planned it in advance, I wondered whether I could actually do it. I told myself that there is only one way to find out. I put my hand around his penis and began rubbing. He started to moan with pleasure.

“Sit down,” I commanded.

When he sat, I went down on my knees in front of him. And yes, I swallowed all of it. It was kind of pleasant.

I stood up and took off my jeans, revealing that I was wearing brief, lacy, black panties. “A little bit of Renee,” I commented. Joe smiled.

Joe slid my panties down and I stepped out of my jeans and panties. I took his hand and put it on my hard penis. “Turnabout time,” I announced, and he took me in his mouth. He also swallowed. We fondled and kissed some more and finally put all of our clothes back on. “I really liked that,” I said.

“Me too,” he answered.

“Well,” I said, “it appears that you might be gay.”

“If I am, then you are too,” he countered.

“It’ll be our little secret,” I said, and I kissed him again.

“Yeah, I don’t think Sue or Becky would like to find out about what we just did,” he said.

“Or that we both liked it,” I added.

Saturday, April 4, 2015:

Becky’s 17th birthday was on Thursday, the 2nd, and our friends were meeting at her house to celebrate on the next Saturday. Given my situation at home, where at least one parent had to approve, I went as Roy. Well, in truth, mostly Roy, with the exception of a brief, black, pair of panties. When I passed by Joe, I whispered, “Black panties.” In response he gave me a pat on my behind. Thankfully, no one saw it.

It being Becky’s party, I paid special attention to her, which included a long birthday kiss, much to the amusement to all present.

During the party, Sue pulled me aside. “You’re Joe’s best friend. There’s something I want to ask you,” she said.

“And what might that be?” I asked.

“Does Joe have another girlfriend?”

“Why would you ask that?”

“Well, in the last few weeks, he seems cooler, less amorous,” she answered.

“I don’t know of any girlfriend, new or otherwise,” I responded, full well aware of Joe’s new love interest, me. I certainly didn’t want to disclose this to Sue.

Later on I motioned to Joe to go outside for a minute. “Sue’s worried,” I told him, “She’s afraid that you have a new girlfriend. She said you’re less amorous.”

“And you know why, sweetheart,” he said, “You’re better than she is.”

“Well, pretend that she’s the best. Show her some love. I don’t want anyone to suspect the truth.”

“Okay, lover,” he responded, “but you’ll owe me.”

“Owe you what?” I challenged.

“You know what.” he said.

Wednesday, April 8, 2015:

Becky and I were sitting at her kitchen table when her mother walked in. “I’m going out to check out the post Easter sales, so I’ll see you in about two hours,” and with that she picked up her purse and walked out the door.

A few minutes after her mother had left, she looked at me with a wicked grin and grabbed my hand. “When the cat’s away, the mice will play,” she said and we went up to her bedroom. “We have at least an hour and a half,” she declared.

We kissed. A long passionate kiss. She held her body close to mine and I could feel myself getting aroused. It appeared that she could feel it also. She stepped away, and pulled her top over her head, exposing her bra. She took one of my hands and put it on her bra covered breast. I began to fondle it, and it was not too much longer that her bra was on the floor. I bent over and began to kiss her naked breasts. She responded by loosening my belt and pulling down my zipper. She then removed my jeans and shorts. She pushed me until I was sitting on her bed and then she knelt on the floor in front of me. When she was done, she swallowed.

She then removed her jeans and panties, and we traded places. I had never done this before, but with hints from Becky, I figured out what to do.

We stopped short of intercourse, because I was afraid that Becky might get pregnant. What we did was wonderful. I can’t be gay, I thought, if I enjoyed it so much.

Friday, May 8, 2015:

I went to this counseling session alone, because I didn’t want my parents to hear what I was going to tell Dr. Devlin. I also dressed.

“Well, what do you want to talk about?” Dr. Devlin asked.

“Sex.”

“Sex?” she questioned, “What about sex?”

“Well, some time ago you noted my sexual inexperience,” I said, and Dr. Devlin nodded her head.

“Well, since then I’ve remedied that situation.”

“How?”

“Orally.”

“Oh?” she questioned, “With whom?”

“Becky and Joe.”

“Both?”

“Yes, but not at the same time.”

“Obviously. And which did you like best?” she asked.

“I liked all of it equally,” I answered.

“When you did this with Joe, did you feel that you were a girl?”

“Sort of, but I was dressed like Roy, except for panties.”

“So you took Joe in your mouth? “ she asked.

“Yes, and then he reciprocated.”

“So you might be gay?” she asked.

“Maybe,” I answered, “But I liked doing it with Becky, and when we did it, I felt all boy.”

“Did you go any further?”

“No,” I answered, “I didn’t to get Becky pregnant.”

“How about Joe?”

“I’m not ready for that,” I answered.

The rest of the session followed along those lines. By the end there were no conclusions.

Saturday, June 6, 2015:

Becky’s parents had enrolled her in an advanced placement program at a university about two hours away. The program was open to incoming highschool seniors, and offered a variety of courses. I would have loved to go, but it was rather expensive, and my father had arranged for me to work at a local muffler and brake shop in town. “It might not pay much,” he said, “but at least it’ll keep you out of that darn dress shop.”

I saw Becky off on that Saturday, Becky looking all the part of a college coed and me looking like a mechanic.

Sunday, June 21, 2015:

It was my day off from the muffler and brake shop, and I was lounging around at home. I was really missing Becky. It was hot, and I was wearing a pair of tan shorts which I had purchased at the tall girl’s shop. They looked unisex so I thought I could ge away with it. I wore a t-shirt which came down to mid-butt. That was not all, however. In addition to missing Becky, I was missing Renee, so I wore a pair of lacy black panties.

It was about noon that Joe called. “Hi, Honey Bunch, how’s my lover, Sweetheart?” he said.

“Stop that!” I demanded, “so what’s on your so-called mind?” I added.

“Aside from you-know-what, I have a problem with my car.” he said.

“What kind of problem?’

“I get a funny noise when I step on the brakes.”

“ Is that funny ‘Ha, Ha,’ or funny ‘Ugh?’” I responded.

Joe just gave me a paind look in response to my attepted humor.

“When’s the last time you checked the brake pads?” I asked.

“That’s not my job,” he said, “You’re the expert on brakes, so it’s your job. My job os to fill your sweet mouth with my love juices.”

I chose to ignore his last comment, and said, “It’s your car, so checking the meat left on the brake pads is your job.”

“Speaking of meat, my meat misses your mouth,” he said with a chuckle.

“Knock it off,” I said, “or I’ll make you take your car to the shop where I work and pay their prices to fix the problem. I’ll come over, but in the mean time, jack up the front end of your car and take off the wheels.”

“Okay, love lips,” he said. He must be really horny, I thought. If the truth be told, I was kind of horny too.

“What’s got into you? Sue cut you off?” I asked with a chuckle.

“Kind of,” he said,

When I arrived at his house, I saw that he had jacked up the front end and removed the tires. The problem was obvious, The driver’s side rotor was scored. He needed a brake job and new rotors on the front end.

“I hope you’ve got some money to buy two rotors and and two sets of pads,” I told him.

“Well, there goes taking Sue to a movie and maybe getting lucky,” he complained.

“Not my problem,” I said, smugly. “Maybe you can hit your parents up for some money?”

“They’re gone for the day,” he said.

I went back to my car and retrieved my coveralls and a box of nitrile examination gloves. Joe gave a questioning look at the box of gloves. “What are those for?” asked.

“We’ve got to pack the wheel bearings with grease before we put on the new rotors,” I answered. “Without the gloves my hands will smell like axle grease for a week. Hardly my favorite perfume.”

“I thought it might be for something more personal,” he said with a crooked smile.

His comment brought another thought to my mind, maybe they could be.

Friday, August 14, 2015:

Becky was finally returning home. After Becky left, my summer was pretty miserable. Although we called each other quite often, my work schedule and her class schedule made it impossible for me to actually visit her in person. As it turned out that was a good thing for me.

After she had been gone for a month and a half, and I noticed a change when I called her. She was not the same old Becky. Something was bothering her, but she wouldn’t confide what it was.

I managed to get the day off for her return, and I was at her house when she and her parents arrived. It was obvious that something was wrong. Her parents also appeared to be very unhappy.

It took some time for me to get her to tell me what was wrong.

“I’m pregnant.” she finally admitted, “I met this guy, Chad, at the school and . . .”

“We only did it once, but that seems to have been enough.”

I was crushed. Not only had she gone out with another guy, but she had sex with him.

All the time, Becky’s parents were giving me accusing looks. I mentioned it to Becky, because it appeared that they believed that I was the father. I knew that I wasn’t.

“I told them it wasn’t you, but right now every teenaged boy is to blame,” she said.

“Did you tell this Chad character?” I asked her.

“Yes, but he said that it was my problem, not his, and he refused to talk with me after I told him.”

“So no marriage, I guess,” I observed.

“No marriage,” she confirmed, “but he did suggest that I have an abortion.

“That’s terrible,” I said.

Thursday, August 20, 2015:

Becky and her parents received a letter from Chad’s parents’ attorney, saying that Chad contested paternity, and would not pay any expenses. He also said that Chad would not admit paternity until it was conclusively proven. He suggested that Becky had been promiscuous with other students that summer, Finally, he demanded that neither Becky not her parents contact Chad or his parents.

This letter seemed to convince Becky’s parents that I was not the father. Becky called me and asked that I come over.

Becky’s mother greeted me at the door. “I’m sorry that we suspected that you are the father, although if Becky had to get pregnant, we would have vastly favored you to be the father. We both know that you and Becky love each other, and you will make a wonderful father one day.”

“I’ll be here for Becky and the baby,” I said.

“You know, a lot of people will believe that you are the father,” Becky’s father observed, “if you are in the picture when the baby is born, are you ready for that? Think about it.”

I thought about it. Maybe ‘Aunt Renee’ would come into the picture.

Monday, September 7, 2015:

By Labor day, it seemed that the entire school knew that Becky was pregnant, and it seemed that most of them believed that I was the father, no matter what Becky or I said.

“Couldn’t keep it in your pants, huh?” one girl commented.

“You gonna do the honorable thing and marry her?” another asked.

Tuesday, September 15, 2015:

About a week later, Becky’s mother called me. “I need a favor, but I hate having to ask you,” she started to say, Becky has an appointment with her Gynecologist today after school, and neither her father nor I can take her there. I wouldn’t ask you, but it is an emergency.”

“Mrs. Jones,” I told her, “I’ll do anything for Becky.” After I said this I wondered if that included marrying Becky and being the father to her baby?

So, on the day I met Becky at my car. “I’m really sorry that my mother asked you to do this. You know, this will convince everyone that you are the father.”

“They can believe what they want,” I said, “It’s you, and not my reputation that concerns me.”

The reception at the gynecologist’s office was decidedly cool. The receptionist and even the Doctor were convinced that I was the father. Only after they worked back the chronology of Becky’s pregnancy that they realized that I was miles away when Becky got pregnant.

When Becky was finished with her appointment, I suggested that she make the next appointment an hour later than usual. “That way the baby’s ‘Auntie Renee’ can drive you to the appointment,” I suggested.

This brought a smile to Becky’s face. “Auntie Renee?” she said, “I like the idea.”

Not only did Becky like the idea, but so did her mother.

Roy And The Road To Renee - Chapter 9

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Fancy Dress / Prom / Evening Gown

Other Keywords: 

  • Male modeling as woman

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 9
By Pentatonic

Wednesday, September 30, 2015:

The school had a course in Civics during the first semester of the year with U.S. History during the second semester. For reasons which were rather unclear, all seniors had to take the Civics course and pass periodic exams in Civics to be allowed to graduate. Those unfortunates who failed the course were required to re-take it during the second semester.

None of my crowd wanted to have to repeat the course, so we really applied ourselves to getting a good grade. With the baby due in the spring, Becky really wanted to pass the course the first time.

Becky, Sue, Joe and I were doing a joint study session at Joe’s house that Wednesday. The topic was the functions of the federal, state and local governments, and how they interrelated. Joe, the cynic, expounded, “All these layers of government do is pass silly laws, tax us to death, and then spend the money foolishly.”

“Yeah,” opined Sue, “let’s say that Roy was all dressed up as Renee, which washroom would he or she be allowed to use?” She turned to me and said, “What do you do?”

“Learn to hold your water and not drink too many soft drinks.” I responded, not wanting to go into the issue too deeply.

“Speaking of Renee, I haven’t seen much of her recently,” Joe said, “How come?”

“I’m trying to keep peace at home,” I responded, “I’m selective of the times I dress.”

“Yeah, but I miss Renee.” he said. Sue was now giving Joe and me strange looks.

“Well, I’m going to work the Holiday Season at the tall girls store, so if you want to see Renee, stop on by the store.”

After finishing the study session, the conversation turned to whether we wanted to attend the Homecoming dance again this fall.

Saturday, October 17, 2015:

All of us decided to attend the Homecoming dance. Joe, being silly, asked me if I was going to run for homecoming queen. “Joe,” I responded, “That’s not even funny. The girls who want to be homecoming queen take it very seriously, and they wouldn’t like it at all. You have to consider their feelings.” Shades of the essay a year ago.

The voting took place the week before the dance. If you bought a ticket to the dance, your ballot counted twice, to favor attendance at the dance. Girls who were running for the position had their names printed on the ballot. Naturally there was a space for a write-in candidate. “Don’t even think about it, Joe,” I warned him.

Despite the warning, I actually received some write-in votes, along with some other boys. I suspected that Joe had a hand in this. Thankfully, only the winner was announced, along with her court which consisted of the other girls who were on the ballot.

Saturday, October 31, 2015:

As the previous year, the girls threw a Halloween party. Becky, being pregnant, wasn’t as enthused this year, and rented a witch’s costume. I decided to go as a mechanic, and wore my coveralls. Although hardly original Becky and I had a good time.

Thursday, November 26, 2015:

Ms. Shay seemed very pleased when I signed up for seasonal work at the tall girls shop. “Do you think that you can work at all on Thanksgiving Day?” she asked.

“All day,” I answered.

“But you’ll miss Thanksgiving dinner with your family,” she said.

“After what happened with my family on New Year’s Day, that will hardly be a loss. In fact, I plan on using work as an excuse. There are some of my relatives who are real asses,” I answered, and I told her what had happened at that family dinner.

“I’m sad that you had such a horrible experience, but I’m glad, actually overjoyed, that you can be at the shop.” she said.

My mother was not happy to hear that I ‘had’ to work that day. “You’ll miss the dinner,” she said.

“But I won’t miss the money I’ll make,” I replied.

I arrived at the store a little after 8:00 on Thanksgiving Day. Ms. Shay had wheeled a rack of dresses outside the front door. There was a big sign on top of the rack which said: “70% DISCOUNT - ALL DRESSES ON THIS RACK.”

“You’re not going to make much money with such a deep discount,” I commented.

“They’re all old stock, and I just want to get rid of them to make room for new dresses,” she explained. She paused for a moment, and then said, “Why don’t you pick one you like, and wear it today? That way we can honestly say that your dress came from this rack. Look, you can have the dress you model.”

That was just too much for me to pass up. There was a satiny red dress with a peplum at the waist, all the better to make my hips look larger. It was exactly my size and when I tried it on, it fit perfectly.

“You look smashing!” Ms. Shay exclaimed when I walked out of the fitting room.

I looked at myself in the mirror. She was right. What was wrong were the colors of my makeup, lipstick and nails. I had worn black shoes to work, and I thought that red or pink shoes would look better with this dress. Ms. Shay saw my concern, and I explained the problem.

“I have a friend who works at a makeup counter. Let me phone her and see if she can give you a quick make over before we get busy. Then pop on down to a shoe store.” With that she reached into the cash drawer and handed me some money. “My treat,” she said, but be a sweety and remember to return what’s left with the receipts.” Her friend said that she could take care of me immediately.

Ms. Shay’s friend, Adele, was waiting for me. She looked me over from head to toe. “I like the french twist,” she said, “but your makeup and nails. . .”

“Ms. Shay wants me to model this dress today,” I responded. “The clothes I wore to work went with my makeup, but this dress doesn’t.”

Adele immediately went to work and cleaned off the makeup I had put on that morning. Out of the blue, she commented. “Your boss has sent some of her ‘special customers’ from time to time. Did you know that?”

“No,” I replied. I wondered if she suspected that I was a lot like the ‘special customers,’ but nothing was said.

When she was done, the results were spectacular. I paid her and gave her a generous tip. She gave me her business card and said, “Come see me again.” I told her that I would.

When I stood up she looked at my feet. “Those shoes. . .” she commented.

“I know,” I said in response. “ My next stop is a shoe store,” I added.

When I returned to the store, Ms. Shay was pleased with the result. “It’s lots of fun, dressing you up, sort of like having my own doll.”

When it finally came time to close, most of the 70% sale dresses had been sold, due, in part, to it being announced that I was wearing one of the sale dresses. Several times during the day customers asked me to model a dress or two, which I gladly did. Ms. Shay was pleased with the results of the day, and when we were closing up, she said. “I liked the way you were willing to model clothes for the customers. That produced a lot of sales. I’m planning some ads for the season, and I’d like to hire you as one of the models, at the going rate for models. How does that sound to you?”

“I’d love to.”

She told me that the photo shoot was scheduled for the next afternoon, and instructed me on what I should wear for the shoot.

When I arrived at home, my mother had brought home some food from the Thanksgiving dinner, which I hungrily attacked. My mother noticed the dress. “I’ve never seen that dress before.” she said, and I explained the circumstances.

It was then that I mentioned that Ms. Shay had hired me as a model for her ads. My sister must have heard the conversation, since she appeared in the kitchen a short time. She checked me out. “All dressed up, and no place to go?” she said with a smirk.

“I’ve been all dressed up, and earning money,” I responded. “The only place I want to go is to bed,” I added.

“How was the dinner?” I asked.

“Same old, same old,” my sister answered, “except for some nasty comments from your uncle. You didn’t miss much. Now tell me about this modeling?”

“I model a bunch of clothes and a photographer takes pictures.” I said, “not too much about it, except that I get paid.”

Amy was studying my dress. “I’d like to wear that dress for a party on Saturday. Is that okay with you?”

Sure, no problem,” I answered, “isn’t that what sisters do?”

“I like you a lot better as a sister than as a brother,” she said with a smile. “Maybe you should be Renee full time,”

Our mother frowned when she heard what Amy had said, so I didn’t answer her. As we were going upstairs, I said to Amy, “Help me get out of this dress. Oh by the way, it might have to go to the cleaners tomorrow, since I’ve been wearing it all day.”

Amy smiled, “As Roy, you sweat. As Renee, you glow. A little perfume will do the job. Oh, I’ll need to borrow some of the perfume you use. Conflicting aromas, you know.”

Friday, November 27, 2015:

The other models and I arrived at the store at about 10:00. I had brought along several pairs of shoes, some underclothing, slips, a short pink satiny robe for a cover-up between shots and my makeup. Ms. Shay had us try on the dresses and clothes she had selected for the shoot. I was lucky, All the clothes Ms. Shay had selected for me to model fit. By noon, we had loaded the clothes in Ms. Shay’s car, and Ms. Shay brought out some sandwiches for a light lunch.

When we arrived at the photography studio at about 1:00 I was surprised to see quite a few people there. First, there was the photographer Steve and his assistant, Sherry. Additionally there was a makeup lady, Ruth, and Shelly, a wardrobe lady who could make any quick alterations if necessary. Rounding out the crew was Annette, a writer from the newspaper for the ad copy and Sylvia, a representative from the modeling agency. It seemed to me to be a whole lot of people for a dozen or so pictures.

After introduction all around, Sylvia was the first to speak up. “Ms. Shay,” she said with a little menace in her voice, “I’m here because you hired two girls from our agency, but I heard that you have brought a third model. According to our contract with you, all of your models have to come from our agency for a photo shoot.”

“She’s one of my employees at my store,” Ms. Shay responded.

“That doesn’t matter,” Sylvia declared, “if she isn’t one of our models, the other models will refuse to participate in this photo shoot.”

Ms. Shay was getting angry. “Look,” she said, “Why don’t you just take your two models and get out of here. I’ll do the whole shoot with just Renee.”

“If you do that, you still have to pay my agency for my two girls.”

“No way!” expounded Ms. Shay, “You’re the one pulling them out.”

While this was going on, the photographer was getting visibly annoyed. “Look, I want to get on with this shoot. Can’t you seem to work this out?”

I was getting intimidated because of all of the hostility over me being a model. “Ms. Shay, if it’s causing a problem, I don’t have to be a model. It’s okay with me.”

It was then that the newspaper representative spoke. “Sylvia, there seems to be a simple solution,” she said, “why don’t you just sign up Renee as one of your models, and we can all get to work.”

“But...” Sylvia started to say before Ms. Shay cut her off.

“That’s okay with me, under the condition that you don’t use her for any of your other jobs without my permission. After all, she is my employee.” Everyone, except Sylvia, nodded their heads, indicating that this was an acceptable solution.

Sylvia just looked a bit deflated, having lost that argument, but she wasn’t going to give up without a few more comments. “But she hasn’t gone through our screening process and given modeling lessons. Also, the owner of the agency has to approve all new hires. She doesn’t even have a portfolio”

“Give it up, Sylvia,” the Photographer said, “I’ll make up a portfolio from the shots from today.”.

Hearing no further objection from Sylvia, the photographer then said, “Good, now that everything’s settled, let’s get to work.”

With that, the clothes to be modeled were put on a rack with numbered hangers, and Ms. Shay, with a smug smile, gave the details of the clothes to the newspaper representative. Then the actual photos were taken. I never realized how many photos were needed, since only one of each outfit would be in the ad. I also realized why so many people, aside from Sylvia, were necessary to make the photo shoot move smoothly and quickly.

There were digital prints made and the photographer studied them. He then turned to Sylvia and said, “You should be glad that you signed up Renee. The camera loves her. She doesn’t need any of your so called training.”

Saturday, November 28, 2015:

The day after the photo shoot, Ms. Shay had the proof of her ad on her desk. She also had a contract from the modeling agency for me to sign. “And how is the new star of the modeling business today?” she said, as she handed me a copy of the ad. One of my pictures was largest and most prominent.

Ms. Shay then added, “I spoke with Mrs. Bates, the head of the Bates modeling agency. She loves you. She even told me how proud she was of Sylvia ‘discovering’ you and signing you up before any other agency snapped you up. I just let all that slide, even if Sylvia was an ass, and had handed her boss a load of you-know-what. Oh, by the way, the lady from the newspaper was really impressed with you. She writes a column called ‘On The Runway’ which appears in the Sunday style section of the paper, and you and the store will be mentioned. Great advertising.”

Sunday, November 29, 2015:

Amy was sitting at the kitchen table reading the newspaper when I came downstairs for breakfast. When she saw me, she exclaimed, “Oooh, we have a celebrity in our midst!”

“Huh?” I responded.

“Look at the paper,” she said as she handed me the Style section of the paper. “Look at the ad for your store, you’re all over it. Not only that but check out the fashion column. Both you and your store are mentioned,” Amy continued and said, “and look at this photo in the column, you’re called a ‘rising star in modeling.’ I’m so happy that you’re my sister.”

My mother entered the kitchen at that moment. “Who’s you sister?” she asked. “You don’t have a sister.” With that, Amy thrust the paper into my mother’s hands. My mother looked at it. Her only comment was, “Oh my!”

Just then the phone rang and my mother answered it. “It’s Becky, and she wants to speak with the rising star in modeling.” I reluctantly took the phone.

“Did you see it?” she asked. I figured out what ‘it’ was.

“Yeah,” I responded. “So much for keeping my cross dressing low key,” I complained. “Now all the kids at school will know about it.”

I was scheduled to start work that afternoon at 1:00. When I arrived at the store, it seemed more crowded than usual. When Ms. Shay saw me she hurried across the store to greet me. “Isn’t it absolutely wonderful?” she exclaimed. “People have come here to see you, and lot of them have bought dresses.” It was then that I noticed that someone had printed out a photo of me and had written ‘Our own Renee’ on it and had pasted a border of gold stars around it like a frame. It was prominently posted by the cash register.

It was then that a customer recognized me. “After I saw the paper, I just had to come here and meet you,” she told me. Her attention to me caused other customers to notice and I soon had customers all around me. I noticed that Ms. Shay had loaded a rack with the clothes that had appeared in the ad.

“Ladies,” I announced, “the clothes in the ad are on the rack. We have a good collection of different sizes.”

“Not all the sizes, now,” Ms. Shay announced. “Get them while you can.”

Some of the customers had brought the Style section of the paper with them and asked me to autograph my picture which I gladly did.

There was a line at the fitting rooms, and when a customer approached me, I turned her over to one of the other clerks to ring up the sale. Ms. Shay noticed this and whispered to me. “You’re giving all your sales to the other girls.”

“Yeah,” I replied, “they didn’t get a chance to model, so it only seems right.” During the day the other girls came up to me and thanked me for letting them get the commissions.

I was tired and hungry when I arrived at my house. Amy and my parents were waiting for me in the kitchen. My father frowned when he saw how I was dressed, but said nothing.

“Well,” Amy asked, “how did it go today? Did anyone say anything about the stuff in the paper?”

“Oh boy,” I answered, “did they ever. The store was packed when I got there, and we were busy all day. Ms. Shay had copies of the column and pictures all over the store, and lots of people wanted to see me and talk with me. I guess that it was my ‘fifteen minutes of fame,’ except it lasted all day. I glad it’s all over, and things can go back to normal.”

“Don’t bet on it,” my father muttered.

Tuesday, December 1, 2015:

I was working an evening shift. The stuff from Sunday was still prominently displayed, and there were a lot of customers in the store. Ms. Shay came up to me as soon as I entered the store. “Our rising star!” she said as a greeting. I just blushed. “You really made a hit. We had a very profitable weekend, mainly because of you.”

Later on, Ms. Shay pulled me aside. “I’ve had several calls from Ms. Bates from the modeling agency. It appears that you are ‘hot stuff.’ She had calls from her clients who want you as a model, and she wants me to allow that. I want to talk with you and maybe allow a few. Think about it.”

“I don’t know,” I replied, and then continued, “I don’t have a lot of time, with school and all, and I don’t want to leave you short handed at the store while I’m at photo shoots.”

“I appreciate that,” she said, “but this might be your big chance.”

Later on, I recognized one of our ‘special customers.’ It was Mr. Stevens, who had been Mr. Thompson’s ‘date’ at the Jones’ New Year’s Eve party, except that at this time he didn’t look much like a ‘Mister.’ He, or maybe I should say ‘she’ was wearing a conservative dark blue dress with an A-line skirt. Her makeup was also conservatively done and she was wearing a styled wig. Altogether, she looked pretty good. “Hello, Renee,” she said.

“Oh, hi, Mr., er, ah. . .” I said with some hesitation in my voice.

“Stephanie,” he said. “Stephanie Stevens,” she added with a big smile. “I like the alliteration, Stephanie and Stevens.”

“So, how can we help you?” I said.

“Not ‘we’ but ‘you.’ I came to see you,” he said. “It appears that the Mr. and Mrs. Jones are hosting a formal New Year’s Eve party again this year, and Mr. Thompson has invited me as his date.”

“Oh?” I said.

“If you’re going to be there, in a formal gown, I want to wear a formal gown also.”

“I haven’t been invited,” I admitted.

“Oh,” she said. “Look,” she added, “my date, Mr. Thompson works with Mr. Jones, and maybe he can drop some non-subtle hints to see that you’re invited. For the moment, let’s assume that it works, so let’s find a smashing gown for me. I’m wearing padding on my butt and hips, so we can do a tight fitting gown,” she advised, “and with a slit, definitely a slit, so I can show off some leg.”

She tried on quite a few gowns. With pleasure, I noted that price was not a consideration. We finally selected a gown in cream colored satin. The skirt was form fitting and it did have a slit which came up to above mid thigh. It had spaghetti straps with a deep plunging vee neckline. It came with a short sleeve chiffon bolero jacket.

“So, what will you wear?” she asked.

“Probably what I wore last year,” I said. “Assuming, of course, I’m invited,” I added.

“But everyone already saw you wearing it,” she complained.

“And they’ll see it again.”

Roy And The Road To Renee - Chapter 10

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Christmas

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 10
By Pentatonic

Saturday, December 5, 2015:

Becky was going into her third trimester soon, and she was beginning to show. Naturally, most of her clothes no longer fit her, so it was decided that Auntie Renee would go clothes shopping with her. Shopping for maternity clothes was a novel experience for me, but Becky and I soon got into the swing of it. Of prime importance were clothes she could wear to school. We thought that clothes that would fit during her whole term were best.

It wasn’t long before Becky’s budget for maternity clothes was exhausted, so I kicked in some of my earnings to round out her new wardrobe. When we returned to Becky’s house her mom insisted on a fashion show. I didn’t know if her mom would approve of me being present during clothes changes, but she said, “I’m assuming that both of you went into the fitting rooms together, so you should stay.”

After modeling all of her maternity clothes, Becky was standing in the center of her room, wearing only her bra and panties. Her rounded belly was obvious, and for reasons which were not clear to me, I rubbed her belly and said, “Hi baby, I’m your auntie Renee.” Both Becky and her mom chuckled when I said this.

“I’m really glad that we have an auntie Renee. It’s important to me,” Becky’s mom said. With that, she stood up and made to leave the room.

Then she said something which made no sense to me at the time, “I’m going to leave you two to have some time together,” and with a leering smile she left the room, closing the door behind her.

I soon found out what Becky’s mom had meant, when Becky took my hands, pulled me to my feet, gave me a hug, and rubbed her belly against mine. When we broke off the embrace, she reached behind her and took off her bra. She then took my hand and put it on her naked breast. With a wicked smile, she then said, “Mom suggested this.” It wasn’t long thereafter that we both were naked, lying side by side on her bed.

Sunday, December 6, 2015:

It was after I returned from work, still dressed as Renee, that my mother turned to Amy and me and announced, “As you two should have figured out, we are hosting the family Christmas dinner, and your father and I expect both of you to be there and on good behavior.”

“Look,” I responded, “I’ll be on good behavior, but what about uncle Ralph?”

“You just worry about yourselves,” she responded, “your aunt Marie and I will take care of him, even if it involves the use of duct tape.” Her last comment caused Amy and me to smile.

She then added, “I expect the two of you to clean up the house and help with the dinner.”

“If I help with dinner, does that mean that I can stay in the kitchen the whole time?” I responded.

“No!” she announced. She turned to me, and added, “And you will wear a suit.”

“A suit?” I questioned. I knew what she meant, but I decided to be a smart alec. “I have this nice suit with a pencil skirt and matching tailored jacket. Maybe a ruffled blouse?”

Amy thought this was humorous, and began to chuckle. My father didn’t. “You know darn well what your mother meant, so stop being a smarty pants,” he exploded.

“Maybe that should be ‘smarty panties’,” Amy said under her breath.

Unfortunately our father heard this and he said, “You behave yourself, young lady.”

After dinner, Amy and I went to her room. “I liked your idea,” she said. “Maybe if you wore the suit with a pencil skirt, our uncle Ralph would blow a gasket when he saw you.” We both laughed.

Friday, December 18, 2015:

It was the last day of school before the Christmas break. Some of the teachers had a mean streak and loaded us up with homework “to keep us from getting bored over the Holidays,” as one teacher said.

The English teacher assigned us to read Twelfth Night by William Shakespeare and to write an essay about some aspect of the play. Since the play involves cross-dressing, I figured that I would write about that.

I gave Becky a ride home from school, and when we arrived at her house, she invited me in for a snack. We were sitting at the kitchen table when her mother walked in, “I don’t know if we gave you an invitation to our New Year’s Eve party, but we’d love it if Auntie Renee would attend. Since the party will run late, maybe you’d like to spend the night here.”

I left shortly thereafter and went home to change for my job. When I arrived at the store, Ms. Shay said that there was a modeling job which I might like, and the photo shoot would be on Tuesday. It was for a mail ad for a Valentine’s Day party at a local night spot. “What will I wear?” I asked.

“They want you to wear something sexy, and one condition is that they have to buy it here,” she said. “We can pick out three dresses for you, and let the client choose.”

“Do I wear one of them when I go to the shoot?”

“No,” she replied, “we can pick out something here for you to wear. I’ll get the details from Ms. Bates. She even said that she will pick you up from here and bring you back. I think she’s doing that so she can get a good look at you.”

Tuesday, December 22, 2015:

I woke up very early to fix my hair and apply some makeup, since I was told to be ready at the store at 8:30 in the morning. The night before I glued on my breast forms to avoid any accidents like one of them popping out of my cups. I also applied some makeup to cover the join, since the dresses which Ms. Shay had picked were rather revealing. Ms. Shay had picked out a skirt and blouse combination to wear to and from the shoot. The skirt was shorter than I liked, and if I was not careful everyone could see my stocking tops and garter straps.

I had packed a ‘Renee’ suitcase with some shoes, my makeup and some extra underclothing ‘just in case.’ Mrs. Bates arrived at about 8:45. I had never met her before, and my initial impression was that she was attempting to look young, despite the ravages of age. Up close, one could see that she was not completely successful.

Mrs. Bates examined me from head to foot, like she was examining livestock at a state fair. She even lifted the hem of my already short skirt to ensure that I was wearing stockings and garters. “Pick up your skirt,” she then commanded, “and let me see your legs.” After I had done so, she commented, “very nice.” We then loaded the dresses and my ‘Renee’ case into her car and headed off to the shoot.

The photo shoot was at the night club, which didn’t open for business until late in the afternoon. The photographer and the rest of the crew were the same people who had been at my first photo shoot. There were about a half dozen models present. The manager of the night club welcomed all of us, and proceeded to select what clothes all of us were to wear for the shoot. Naturally, he chose the dress with the longest slit for me to wear.

I took off my street clothes and put on a robe for makeup. The makeup was nighttime makeup and heavily applied. I put on some sparkly dangling earrings to go with the nighttime look. I noted that only one other female model was wearing stockings and garters.

My first shot had me sitting sideways at the bar facing a good looking guy. We were holding drinks and smiling at each other; at least I was smiling. He was leering. Of course, the slit in my dress was facing the camera, and after a few shots the photographer arranged my skirt to have my whole leg, stockings and garter straps exposed. He and the manager liked this and a lot more shots were taken like this, including some that involved kissing.

There were a lot of shots taken, some at tables, some at booths and some on the dance floor. As could be expected, the photos of me dancing involved me showing a lot of leg through the slit. It being a Valentine’s Day event, there were poses of couples kissing. Naturally, as before, I was the girl in some couples, with a lot of leg showing through the slit.

The photo shoot was finished by about 1:00 and the club provided sandwiches and non-alcoholic drinks for all present. I got to keep the dress which I wore for the photos. The manager came over to me and said, “I’d like it if you came to the Valentine’s Day party wearing that dress.”

“I’d like to,” I replied, “but I’m not twenty-one.” I could see the disappointment on his face.

I took the time to thank the photographer and his crew, and I asked him if I could have a few copies of my photographs for my portfolio, “Let me look at them and select a half dozen of the best for you, except that might be a hard job, since all of your photos are great.”

On the ride home, Mrs. Bates was all bubbly. “I’m so happy to see you in action, you were wonderful. You really impressed the photographer and the manager. I can see a lot of work for you in the future.”

When we returned to the mall, we brought the dresses and my case back to the store, and Mrs. Bates and Ms. Shay engaged in an animated discussion of how the shoot went. “Renee was the star of the shoot,” Mrs. Bates enthused.

After work I took the dress home to show it to my sister. Naturally, I had to put it on for her. “That is one sexy dress,” she exclaimed, “Where are you going to wear it?”

“I’ll wear it at the store a few times. Otherwise, I don’t know,” I said, with a tinge of sorrow in my voice.

“Then you’ll let me wear it?”

“Sure, isn’t that what sisters do?” I said, with my frown turning to a smile.

“Hey, keep it on,” Amy said, “You’ve got to ask Becky to come over and see you in it.”

“Okay,” I replied.

“How about Dad?” she asked.

“He won’t like it, so why upset him,” I replied.

Becky loved the dress, and had to play with the slit. “You know, I bet Joe would absolutely love to see you in this dress,” she commented.

“He won’t,” I said.

Friday, December 25, 2015:

I had evaded my mother’s family on Thanksgiving by working all day at the store. I had no excuse to do the same on Christmas, since the store was closed on Christmas Day and my family was hosting the dinner. The past few days had seen hectic activity in cleaning the house, buying the food and putting up Christmas decorations.

We opened gifts in the morning and afterwards I took a shower and put on my Roy suit. The relatives were supposed to arrive at about 4:00 so I was able to have a few minutes to visit Becky at her house and exchange gifts. When I arrived at her house, Mrs. Jones answered the door. “No Auntie Renee?” she exclaimed.

“We’re hosting the family dinner, and my relatives don’t want to see Renee. Remember what happened last New Year’s Day.”

“Oh yes,” she said, “Now I understand.”

“But you’ll see Renee on New Year’s Eve,” I added, “If not before.”

I had picked up my photos from the night club photo shoot, and brought them with me. “Do you want to see some photos?”

Of course they did. I had six photos and a proof of the mail ad. The mailing was a post card, and I was prominently shown kissing on half of the side where the mailing label would go. This picture was surrounded by a big heart. There were other pictures in a montage on the other side. In all photos I was showing a lot of leg.

“You look very sexy,” Becky’s mom said.

“That seemed to be the general idea.”

I arrived back home shortly before the guests were to arrive. Amy and I were put in charge of greeting them at the door and taking their coats. Then the moment of truth arrived; I saw my aunt Marie and uncle Ralph approaching the door, and steeled myself for a confrontation which never arrived.

“Merry Christmas, Aunt Marie, Uncle Ralph,” Amy and I said in unison.

“And a Merry Christmas to you, Amy and Roy,” my aunt said. My uncle just grunted. The sour expression on his face was obvious to all but especially to my aunt. “Ralph. . .” she said menacingly. It was at this point he said “Merry Christmas.”

I was attempting to interest my male cousins in a recent movie which I had purchased when my sister called me. “Roy, do you have a minute?”

“Sure, sis, what’s up?”

“Come to my room.”

My sister and female cousins were all in her room, with slightly wicked smiles on their faces. Nothing good could come from this, I thought. On prominent display was the dress which I wore at the photo shoot at the night club. Why did I ever tell her she could borrow it? I thought.

“Roy, what do you think of this dress?” she asked with a look of false innocense on her face.

“Very nice,” I said, feigning disinterest.

“Oh, come now,” Amy said, “take a better look at it,”

I walked over to where the dress was hanging. My cousins were now giggling. I pulled out the skirt, revealing the slit, and frowned. “Hardly suitable for a girl your age. It’s rather tarty,” I said.

“Too tarty to wear to a night club? On Valentine’s Day?” cousin Rachael chirped up.

“Maybe you’d like to see some pictures of this dress?” my sister said, as she picked up my portfolio. Now all of the girls were laughing. I was caught.

“Okay Roy,” cousin Natalie said, “time to spill the beans. We want details.”

“We want all of the details,” cousin Sandy said.

“Well, I’m a model with the Bates agency, and I was hired for a photo shoot.”

“Wearing that dress?” Sandy asked.

Before I could answer, Natalie asked, “At a night club?”

“It was a photo shoot, done before the club opened for the day,” I said, “They wouldn’t have let me in if they were open, because I’m underage.”

“But that is you, wearing that dress?” Rachael asked.

“Yes,” I softly admitted.

“How come Amy has the dress in her closet?”

“Because she asked if she could borrow it, and I said yes,” I said, “It’s a sisterly thing to do,” I added, instantly regretting what I has said.

“So you consider yourself to be Amy’s sister?”

“Sorta, and at some times.” I admitted, “It’s sort of a secret,” I added.

“Look, I’ll keep the secret if you go around with me, dressed like that, to pick up boys. You are a real boy magnet,” Rachael added.

“Wow, my cousin’s a fashion model,” commented Sandy.

I then related how I became a model, and told them how much I earned for a photo shoot. This discussion continued until we were called to dinner. Thankfully, Uncle Ralph and I were seated at opposite ends of the table, and there were no unseemly outbursts from him. For my part, I said as little as absolutely necessary.

After dinner, I mentioned to my sister and cousins that I would be wearing that dress at the store on Wednesday, and they could see me in it if they came to the store.

“We’ll be there,” Rachael said.

“You can bet your panties in it,” Natalie added, and the cousins chuckled loudly.

Wednesday, December 30, 2015:

True to their words, Amy and my cousins showed up at the store, and true to my word I wore the dress. When Ms. Shay saw us, she came over and said, “Here’s some cash, so why don’t you go to the food court and cause some excitement.” We packed some filler in some of the store’s bags and brought them with us to show that we shopped at the store.

We went to the food court and did indeed cause some excitement. Several women asked if my dress came from the store, and I told them that it did.

Thursday, December 31, 2015:

Today I arrived at the store when it opened so I could leave early and get dressed for the New Year’s Eve party. My mother had not wanted me to stay the night at Becky’s house, but Mrs. Jones pointed out that the party would run well past midnight, and that there were a lot of crazy drivers on the road. Finally she talked my mother into letting me stay overnight.

I packed my car with my Renee suitcase and hung my gown in the back of the car. It was the same gown that I had worn the year before. Ms. Shay wanted me to get a new gown. “You’re a model,” Ms. Shay said, “You can’t wear the same gown two years in a row.” I pointed out that I wouldn’t have a lot of places to wear a gown, new or old. I also pointed out that I was running out of closet space, because I also had all of my Roy clothes in my closet.

“You are a representative of the store,” Ms. Shay responded, “Wearing the same gown would be a negative reflection of the store.” Ms. Shay and I went over to where the evening gowns were. After she looked at what was there, she pulled a satiny royal blue gown from the rack and handed it to me. “Here,” she said, “try it on and let’s see how it looks.”

When I put it on, I noticed that it had a long slit. I pointed it out to Ms. Shay. “Most of the gowns which you have worn have a slit. Your public likes it.” I liked the gown, regardless of what ‘my public’ liked, so I bought it, using some of my money from the night club shoot and my 60% discount.

I let Amy wear the dress which I modeled at the night club shoot. When my mother saw the extent of the slit, she offered to sew it shut. “It’s shameless,” she declared.

“If it’s good enough for my sister, it’s good enough for me.” Amy replied. My mother frowned when Amy said ‘sister’ but didn’t say anything. My mother did insist, however, that Amy wear pantyhose and not stockings and garters. “Showing off the tops of stockings and garters is just too immodest,” she declared.

I, however, was not prohibited from wearing stockings and garters. Maybe my mother believed that I was beyond hope of reforming. If so, she was right.

The first thing I did when I arrived home from work was to use hair remover and take a shower. I used a very floral smelling lotion afterwards. I then glued on my breast forms and used concealer to hide the join. This was followed with my hose and corset. I also put on the sexiest panties and topped it off with a skirt and blouse, which I would also wear coming home the next day. Finally, I packed a very sexy nightgown. Suitably equipped, I went to Becky’s house.

Becky wanted to help me get dressed, which wasn’t totally necessary. I guess that she wanted me to help her get dressed, which also wasn’t totally necessary. However it would be fun, so that was what we did. Once in her bedroom, she unzipped my skirt and let it fall to the floor. The skirt was lined, so I was not wearing a slip. She then unbuttoned my blouse and I shrugged it off. I then undressed Becky and kissed her pregnant belly. Soon our panties joined our other clothes on the floor.

As we did the year before, Becky and I greeted the guests at the door and took their coats. I was particularly interested to see what Mr. Thompson’s companion, Stephanie, would be wearing. I was not disappointed. She was wearing the gown she and I had picked out at the store.

“You look stunning,” I said.

“Thank you.” she said, “and so do you. Isn’t that a new gown?”

“It is,” I answered. “I took your suggestion. It isn’t as glamorous as your gown, because I don’t want to compete with you.”

“You are such a dear,” she said, and we gave each other air kisses, the better to not smudge our lipsticks.

A while later she pulled me aside and said, “I received a mailer about a Valentine’s Day party at a certain night club. Do you know anything about it?”

I blushed. “Ahah,” she exclaimed, “It appears you do. Now tell me all about it.”

I explained that I was doing some modeling and was assigned to that photo shoot. “I’ll bet that you were first choice for the photo shoot,” she said.

“I wouldn’t know about that. What I do know is that it pleased Ms. Shay, because the night club had to pay for the dress, and after the shoot it was given to me.”

“I’d like to see you in that dress. How come you’re not wearing it tonight?”

“I didn’t think it was formal enough and I loaned it to my sister to wear it tonight,” I answered.

“But it is sexy enough,” Stephanie commented. “By the way,” she added, “I liked the photo of you kissing that man. It looked like you enjoyed it. Did you?”

“I did, he was a good kisser.”

“So you don’t mind kissing men?”

“No, but I also like kissing girls.”

“I have to visit the washroom,” she then said. “Why don’t you come with me?”

I had a good idea what Stephanie wanted, but I wanted the same thing. When we were in the washroom and the door was closed, she said, “Would you let me kiss you right now, given that we both know the other is male?”

I answered her by embracing her and giving her a deep, passionate kiss.

“Wow.” she said, “Let’s do that again.”

We did. “Looks like both of us have to repair our lipsticks,” she said.

After fixing out lipsticks, she said, “It probably would be better if neither Robert nor Becky, or anyone else, knows about this.”

I agreed with her, and we rejoined the party.

The party wound down at about 2:00, and another half hour passed before the last guest left. Becky’s mom and I were picking up glasses in the front room when she said to me, “I really appreciate the support you’ve given Becky. Being pregnant, she feels that she is not attractive or sexy. Therefore, I’d like you to share her bed with her tonight. I found some pretty, matching, nighties for the two of you to wear.”

What could I say? Becky’s mother really wanted me to have sex with Becky. How could I resist? The plain truth was that I couldn’t resist the invitation.

Friday, January 1, 2016:

Becky and I woke up about 10:00. There were clothes scattered all over the room. I found my nightie crumpled in the bed clothes. At least I thought it was mine. A further search turned up the other nightie. Clad only in the nightie, I went to take a shower. While in the hall, I met Becky’s Mom. She smiled at me, and said, “That nightie looks good on you.” I thanked her and went into the bathroom.

After my shower, I realized that the only thing I had brought with me to the bathroom was the nightie, so I put it on. Becky did the same. We heard Becky’s mom call out that breakfast was ready. Since Becky’s mom had already seen me clad only in a nightie, I figured that it was okay for me to wear it downstairs. Becky and I, so clad, walked into the kitchen hand in hand.

Becky’s mom smiled when she saw us. “Those nighties look darling on you, but I don’t want you to catch a cold, so why don’t you get dressed and come back down in a few minutes.” I dressed in the same skirt and blouse that I had on when I arrived at Becky’s house the previous day.

When Becky passed by her mom, I heard Becky say. “Thanks Mom, for everything.” Becky’s mom had a knowing look on her face when Becky said this.

It was about noon when I arrived home. I had hoped to make it to my room without seeing anyone. No such luck. My parents and Amy were all sitting in the kitchen when I went through the back door.

“Did you have a good time?” my mother asked, which produced a giggle from my sister. My mother then realized what she had asked and rephrased her question, “How was the party?”

“Okay,” I said, “it was lots of fun.”

“I’ll bet it was,” my sister remarked with a wicked smile. I just gave her a dirty look in response.

My father, who had remained silent during this exchange, finally spoke up, “I have a New Year’s resolution for you. No more dresses or skirts.”

This was too much for Amy. “Does that include skorts or culottes?” she piped up with a snicker.

“Amy, you keep out of this,” Dad said, “This is between your brother and me.” He looked at me and asked, “So?”

“No,” was my brief answer. “I will work at the store from time to time and there are the modeling jobs,” I added.

“Well.” he said, “anything else?”

“Yeah, when Becky and I go shopping for the baby. If I dress as Roy, everyone will think that I’m the father.”

“They already do,” he responded. You wearing a skirt won’t change that. By the way, I’m not so happy with the fact that my son is a fashion model for women’s clothes. That night club ad is shameless.”

“But it means money,” I said, “good money that I can use towards my college education.” He couldn’t argue with that, I thought.

“Look, Dad,” Amy said, “I don’t want to give up my sister,”

My dad just snorted and said no more.

The New Year’s Day dinner was held at my aunt Marie’s and uncle Ralph’s. I was viewing it with some foreboding, given my uncle’s behavior a year before. As every year before the men went to the rec room to watch bowl games, which meant a lot of people in the room. My dad, uncles and male cousins plopped and sprawled in most of the seats in the room. I spied a straight back chair at a desk in the corner of the room, away from everyone else.. Force of recent habit took over and I sat on the front of the chair, my back straight, shoulders back, knees together, legs crossed at the ankles and my hands in my lap, just as I would if I were wearing a skirt. I didn’t realize that this was the wrong thing to do until uncle Frank gave me a strange look during a commercial, and asked, “Hey Roy, something wrong with you?”

I suddenly realized what happened, and I had to think fast. “Got a crick in my back,” and wriggled as if trying to work it out. I then slumped down in the chair and threw one arm over the back of the chair.

Uncle Ralph had to try to be mean and funny at the same time. ‘Probably comes from wearing a bra all the time,” Thankfully everyone ignored him. It was at this time it was announced that dinner was ready.

On the way up to the dining room my cousin Phil whispered, “You still doing. . .ah. . .you know what?”

I knew exactly what he meant. “Yeah,” I whispered back.

“Why?”

“Money. I still work at the store, and in addition I’m doing modeling.”

“Like girl’s clothes?”

“Exactly,” I responded.

“Cool,” he said. “I’d like to see you sometime, dolled up like a chick.”

“I’ll be at the store tomorrow. Swing by, and see for yourself.”

The rest of the day passed without incident. As I was taking stuff out of my purse, I noted a card that I had not seen before. It said ‘Call me, Stephanie’ and it had her cell phone number. I put it in a book, like a book mark. I wondered why she had given it to me.

A new year. I hoped it would be a good one.

Roy And The Road To Renee - Chapter 11

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

Other Keywords: 

  • Dress Modeling fashion show

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 11
By Pentatonic

Monday, January 4, 2016:

The first day back at school after the break was cold and overcast, the weather mirroring the moods of the student body. Mr. Burns, the English teacher, on the other hand, walked into class with a smile on his face. “Hope you all enjoyed Twelfth Night. Does anyone know what twelfth Night is?” I knew, but I didn’t want to call attention tp myself. “Anyone?” he repeated. Reluctantly, I raised my hand.

“Mr. Evans?” he said.

“It’s the end of the Christmas Season, and involves a lot of drinking and eating.”

“Very good,” Mr. Burns responded, “which is tomorrow for those who care. Please remember that your papers are due on Wednesday, which is Epiphany. From your papers I should be able to discover who actually read the play and who only surfed the internet for easy answers.”

I felt smug. Not only had my friends and I read it together and discussed it among ourselves, but I had actually written my paper, It was entitled: ‘Twelfth Night - Successful Cross-Dressing.’ In my paper I also made references to Cheribino’s cross-dressing in Der Rosenkavalier. I had my completed paper in my backpack, but was reluctant to turn it in early and incite the ire of my classmates.

Monday, January 11, 2016:

Mr. Burns brought our papers into class. “Well, it seems that some of you tried to fake it, and it was obvious, an ephiphany of sorts. However, there was a group of you whose papers were very good. I don’t want to embarrass anyone, but perhaps Miss Jones could explain what she did.”

“A group of us met and we assigned roles and we read the play aloud and together, since the play was intended to be heard. After each act we shared our thoughts,” Becky explained, “It took more time than the run time, but we had a lot of fun. The biggest problem was finding a time when everyone was available. We also discovered that we had some unrepentant hams in our group. I would tell you who they were, but some of their egos are already at the bursting point.” This produced a chuckle from the members of the class.

“You have discovered the best way to understand a play. I commend you and your fellow students,” Mr. Burns said.

All eight of us received ‘A’s on our papers.

That afternoon Ms. Shay telephoned me. “I received a call from Mrs. Bates. It seems that Coffrey’s Department Stores at the mall wants to do a four page full color ad for spring fashions which will be inserted in the paper to appear on a Sunday. She wants you as one of the models and she wanted to know if that was okay with me before she called you. Naturally, I don’t like a competitor using my employee, but it is too good of an opportunity for you to pass up. The store wants to have a fashion show, complete with a runway, in the food court on the Saturday before the ad appears.”

“Sounds cool,” I said.

“Okay, I’ll have Mrs. Bates call you with the details.”

Thursday, January 14, 2016:

On Wednesday I had spoken with Mrs. Bates and confirmed that I would be delighted to model. “There is a photo shoot at Coffrey’s Department Store a week from today in the afternoon. They’re doing a spring clothes ad and they are using the bridal salon since it has the most room and a pretty background. There will also be a fashion show in the food court of the mall on the Saturday afternoon before the ad is put in the paper. They’re going to set up a runway, and you’ll model various outfits and walk up and down the runway.”

This runway business didn’t seem quite as simple as Mrs. Bates would have one believe. I had seen some views of fashion runway work, and I thought that I better look into it before the actual day.

I then thought about Stephanie’s card.

During lunch hour, I called Stephanie, and expressed my concerns and asked her if she knew anything about working on a runway. “As a matter of fact, I do,” she said. “Why don’t you stop over at my place this afternoon after school?”

It was a school day, and I was all Roy. I didn’t want to stop off at home and have to answer a bunch of question, so I’d have to go as I was. I did call home and lied to my mother and said that I was going to hang around with some of the guys but would be home before supper. Maybe not too big a lie, because Stephanie was, in truth, a ‘guy.’

When I arrived at her place, Stephanie seemed to be surprised to see Roy at her door. “What? No Renee?” she commented.

“No time to change,” I answered, “remember, I was at school all day?”

Stephanie obviously had time to change. She was wearing a negligee with only a bra and panties underneath and a pair of furry slippers on her feet. She was also wearing expertly applied makeup.

“On the phone you mentioned being in a fashion show and need to learn how to walk down a runway.” she said.

“Yes.”

“As a female?”

“Yes.”

“Okay, now let’s talk about runways,” Stephanie said. “I would expect that there will be a little stage with the runway extending in front of it. I also expect that there will be curtains at the back of the stage. You might come from behind the curtain either in a group or singly. If in a group, you will, one by one, go down the runway, turn, go back and stand on the other side of the stage until everyone has done the runway. If singly, you will come from behind the curtain, alone, and do the runway. They’ll tell you how they want to do it. Now, the important part is how you walk the runway. Let me show you what I mean. Pretend that this hallway is the runway.”

She moved to one end of the hall and walked down it, turned around, and walked back. “The important part is to put one foot directly in front of the other, like this,” and she demonstrated what she meant. “Lead with your toe, not your heel, and put a sway in your behind. It makes your skirt move nicely.” She then demonstrated this. “Your turn is important. If you have a full skirt, you want it to flare up when you turn. Watch me.”

She then had me walk up and down the hall, watching and commenting on how I was walking and turning. Finally she declared that I was ready

Wednesday, January 20, 2016:

The actual photo shoot was not unlike the others in which I had participated except there were a lot more people involved and it was being done ‘green screen.’ With green screen, the only background is a green screen. The background can then be added. There were models present, along with makeup artists. The store provided people to handle wardrobe. The photographer had two assistants. There even was a director.

My first photo had me wearing a yellow print halter sundress. I had one arm extended and someone put a fake bird on my extended index finger, and I looked at the bird and smiled. A lot of shots were taken with me and the bird, with the photographer and director reviewing the shots before taking more. I then modeled a lot of different outfits, and I noticed that some of my fellow models wore the same outfits that I wore. However, no one else did the bird thing.

In general, I followed directions, and at one point the photographer came up to me and said, “Honey, I wish all of my models were like you. You’re good looking, you’re easy to work with, you follow directions and most importantly, the camera loves you. What agency are you with/”

“Bates,” I replied with a smile.

“And your name?”

“Renee Evans.”

“I’ll be sure to ask for you for future shoots,” he concluded. This made me feel good. Another thing that made me feel good was that the director, who was in charge of advertising at Coffrey’s, offered me a job.

Saturday, January 23, 2016:

I awoke early on the day of the fashion show to use a hair remover and to reattach my breast forms. I had used some of the money I earned modeling to buy top of the line breast forms and makeup to conceal the join. I also used some makeup to give a hint of greater cleavage. Naturally, Amy was an enthusiastic helper, even offering to help me with my gaff, which help I declined.

I had a 9:30 appointment at the salon for hair, makeup and nails. I was assured that everything would be completed a little after eleven, which it was.

I very carefully dressed, choosing clothes which would make changing clothes easy, but which also looked good on me.

Amy drove me to the mall to save me from having to spend time looking for a parking space. I arrived with plenty of time to spare and checked in with security. The store had planned to run the show multiple times that day. The first show would be at 1:00, with four other shows starting on the hour thereafter.

My first stop was makeup, and when the makeup artist saw me she said, “Oh Honey, your makeup is wonderful. I don’t have to change a thing. Who did it?”

“I had it done this morning at my salon,” I responded.

“Well, stop by each time before you go on, in case we have to repair anything,” she said.

I then located where I would be changing into the different outfits which I would model. There were clerks from the store assigned to help the models change outfits. The models were put in groups of four, and each model in a group was assigned a number. I was number one in the first group. I would model the same yellow sun dress which I wore in the photo shoot, minus the bird.

All of the outfits to be shown were given a number, and the store had printed a sheet identifying, the outfit by number, a description, where in the store it could be bought and the price. These were freely given to all of the members of the audience. There was a numeric display above the stage which showed the number of the outfit while the model walked down the runway along with an announcer who provided commentary.

The store manager made welcoming remarks and music was started. I listened to the beat, and planned to walk in time to the music. I was the first model in my group of four, and the first model to walk on the stage, accompanied by applause and wolf whistles. As Stephanie had taught me, I pranced down the runway, did my turn which flared out the skirt, and pranced back., wiggling my behind. The audience loved it.

I looked at the audience and recognized Annette from the newspaper, who wrote a weekly column for the style section called ‘On the Runway.’ I had appeared in that column once before where Annette called me a ‘rising star in modeling.’ After the first show, I was sitting and waiting for the makeup lady when Annette came over to me. “Oh, Renee,” she said, “You were absolutely wonderful. Where did you learn that walk?”

“A friend taught me.”

“Well, she did a great job. It was wonderful to see you strut your stuff. By the way, the store’s ad campaign is called ‘Fly Into Spring,’ and you are the centerpiece. Your picture with the bird is front and center in the newspaper insert and is posted all over the mall to draw attention to the fashion show here.”

I was a little surprised with what Annette had said.

Just before Annette excused herself to talk with some of the other models, she said, “Make sure you read my column tomorrow.”

Sunday, January 24, 2016:

I was woken up when I heard my sister yell, “Hey, sis, get your pretty butt down here. Now!”

I was tired when I went to bed the night before, and I had not removed my Breast forms. Given the immediacy of Amy’s request, I put on a bra and some panties and covered it with a terrycloth robe. The first order of business was getting some coffee.

The Sunday paper was spread out on the kitchen table, with the Style section and store ad on top. Amy had an enormous smile on her face, which contrasted with my mother’s frown. My mother was the first to speak. “Shameless,” was all she said.

I had no idea what was going on, so all I could say was “Huh?”

“You!”

“Me?”

“Yes, prancing and strutting around like some loose woman,” she said. She then turned to Amy and said, “I don’t like it when you refer to Roy as your sister. He’s your brother, and don’t forget it.”

“Would someone please tell me what’s going on while I get a cup of coffee. I’m still half asleep?”

“No, you stay where you are until I’m finished with you!” my mother commanded.

“Okay,” I replied, “I’m listening.”

My mother picked up the ad insert and pointed at my picture, the one with the bird. “Look at you, standing under a rose trellis, looking all sweetness and innocence. Then look at you on that runway, looking like sin incarnate.”

“That’s what a model is supposed to do on the runway,” I said in defense. “I get paid money to do that.”

That was the wrong thing to say, because my mother countered, “Like a prostitute gets paid!”

I looked at Amy, and mimed drinking coffee. She got the message and brought me a cup. My mother then picked up the Style section of the paper and shook it at me. “Did you see what that Annette said about you in her column. You shouldn’t be looking to her for proper moral guidance.”

An evil thought came to my mind: better her than Stephanie. My mother was staring at my chest. “I see that you’re still wearing those falsies!” she declared. “Are you also wearing a bra and panties?”

I decided not to answer that question, but that did not stop my mother’s diatribe. “I don’t know whatever came over you to dress like a woman.”

I had too much of her railing at me. “You remember when my class had to write about how it would be to be the opposite sex, and you and Becky went out and bought me a bunch of girl clothes? It was you who started it.”

“But how about the Halloween party and you as the Queen of the Night?” she countered. “Maybe it should have been ‘QUEER of the night.’ Did you see what that Annette said about you in her column?” I obviously had not had a chance to read the column, so my mother supplied some juicy tidbits from it, like “She really knows how to strut her stuff” and “delightfully sexy moves.”

“I saw it and It was just plainly disgusting.” she concluded, but then added, “Go upstairs and get dressed before your father sees you like this.”

Amy grabbed the Style section of the paper and the store ad, and said, “I’ll take these with me so Dad doesn’t see them.” With that she followed me upstairs. Once in my room I took off my robe. “You are wearing a bra and panties!” she exclaimed.

After I took a shower and after I changed into my Roy clothes, I was able to look at Coffrey’s ad and the column written by Annette. She was lavish in her praise of me, even referring to her previous column. When I had finished, Amy said, “You really were the star of the show. Everyone loved you. Look at the ad, there are lots of pictures of you in it. The reaction you got when you were on the runway was fabulous. I am so proud of you and that you are my sister.”

Amy then thought about what she had just said. “You still are my sister, aren’t you?” she asked.

I smiled at her and said, “Absolutely!”

Wednesday, January 27, 2016:

I received a call from the Coffrey’s Manager. “The reaction to you at the fashion show was fabulous,” he said. “There is a lot of interest in you, and a lot of people want to meet you. What we would like to do is have you at the entrance on Saturday and greet customers coming into the store. You would be wearing the yellow sun dress. It would be for about five hours, from 10:00 until 3:00. Are you interested?”

I told him I was, and started planning how to pull this off without my parents knowing about it. I called Becky and told her about it, and we decided that, if necessary, I could get dressed at her house.

I also called Ms. Shay and she said it was okay. I also called Mrs. Bates, and she said she would work out the financial details with the store. She then added, “By the way, after the positive reaction to the show, we’re upping your modeling rates. I think that you’ll be very pleased.”

Saturday, January 30, 2016:

I woke up very early that morning, and put extra care in my makeup and hair, trying to duplicate my look from the fashion show. I even glued on my breast forms and used makeup to hide the join. Amy joined me when I was just finished getting dressed. “How’s it going?” she asked.

“How do I look?” I said in the way of an answer.

“Gorgeous!”

“Now, how do I get out of the house without the parents seeing me?”

“I’ve scouted the situation. Both parents are in the kitchen eating, so I think we can sneak out of the front door.”

I successfully escaped from the house and arrived at the employee’s entrance at the store at about 9:45, where I was met by the store manager. “Your admiring audience is already collecting at the main entrance. Now, let me see how you look,”

I took off my coat and he looked me up and down. When he was finished, he declared, “Fabulous!”

The manager and I made our way to the front entrance where I was greeted with applause and whistles. I noted that there were a lot of pictures of me posted all over. All of this gave me a warm glow and I smiled. I then addressed the crowd, and said, “I’m looking forward to chatting with each of you, but first you should notice that there is a list of outfits from a week ago, and there is a video monitor replaying the fashion show. The reason I mention this is that if you buy one of the outfits and show the sales clerk the list, you get an automatic fifteen percent discount.”

The store manager then took over. “One other thing is that there are pictures of Renee on this table, and if you have a sales receipt from the store for any day in the past two weeks, you get a picture and Renee will personally autograph it if you want.” This did not seem to be a big deal to me, but it did cause a buzz of excitement and a flurry of searching through purses and pockets. “This offer is good for the next five hours, so if you can’t find a receipt, we have plenty of merchandise on hand, so if you buy anything, and I mean anything, that will work.”

I began to mingle with the people and made it a point to talk with each and everyone present. To my delightful surprise, they acted like I was a real celebrity, and not just some kid from the local high school. While this was going on, the manager was handing out photographs. I did notice receipts being handed from one person to another, and I was sure that the manager noticed the same. However, that didn’t phase him and he kept on handing out photographs, which was the main idea. The photos were of me under the trellis with the fake bird on my finger and were printed on glossy paper. I guess that if people thought they were of some value, it would be great advertising for Coffrey’s.

I then sat down at a small table and began autographing each photo as it was handed to me. I even personalized them if requested. Naturally I had to be pleasant and charming as I could be with a big smile on my face. The manager noticed this and smiled back at me.

After the initial crowd had their autographed photos, things quieted a bit. It was then that I noticed a trio of girls who were in my class at school. One of them kept staring at me. “Excuse me for staring, but you remind me of someone I know, but I just can’t place her,” she said.

Good pronoun, I thought. “I hope she’s not prettier than I am,” I said.

“No, no, nobody could be prettier than you.” she replied. Talk about an ego boost. The fact that she couldn’t place me was a plus. Maybe it’s the fake boobs, I thought. If so, they were worth every penny I paid for them, and that was a lot of pennies.

During my greeting session, a lot of the customers took my photo on their cell phones, some of me alone but most of them with me posing with their friends. There was, however, a man who hung around most of the time snapping photos. He had the look of a professional photographer. When I asked the manager, I was told that the store had hired a photographer for the event. “We plan on doing a piece on our spring ad campaign, and today’s event will be part of it,” he said, “I’ll get you some nice prints for your portfolio,” he added.

Naturally, Amy, Becky and my friends had to show up and get autographed photos. Later on, Amy came up to me. “My, my,” she said, “Aren’t we the celebrity.”

“Yeah,” I replied, “fifteen minutes of fame, and my feet feel like I’ve used fourteen minutes of them already.”

“No,” she answered, “you’ve got a lot more minutes coming. By the way, when you are ready to come home, give me a call and we can figure out how we can get you into your room and back to being Roy without the parents any wiser.”

“Thanks sis,” I said, “I couldn’t do it without you,”

“That’s what sisters do for each other,” she said.

Roy And The Road To Renee - Chapter 12 - Conclusion

Author: 

  • Pentatonic

Audience Rating: 

  • Younger Audience (g/y)

Publication: 

  • Final Chapter

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • School or College Life
  • Voluntary

TG Elements: 

  • Pregnant / Having a Baby

Other Keywords: 

  • Boy modeling dresses

Permission: 

  • Posted by author(s)

Roy And The Road To Renee - Chapter 12 - Conclusion
By Pentatonic

[Author’s note: I’m sorry for the long delay in posting this chapter. Some things came up and turned my life around, and now things are settling down.]

Friday, February 5, 2016

I had another counseling session, this time with my parents. I wanted to resolve the growing hostility they had to my dressing as a female. Naturally, my modeling was a big part of it.

After the usual bringing Dr. Devlin up to date, I said, “I get the feeling that my parents want me to totally stop dressing as a girl.”

“Is that true?” she asked my parents.

“Absolutely!” my father asserted and then added, “We think that this has gone on way too far.”

“In what way,” Dr. Devlin asked.

“He’s our son, not our daughter,” my mother answered.

“But I thought you three had worked out a deal?” Dr. Devlin asked.

“We had, but it didn’t work,” my mother said.

“What changed?”

“He’s a female model,” my father said.

“For which I am well paid,” I interjected.

“What happened is he was hired for a department store spring fashion ad campaign,” my mother said.

“What’s wrong with that? He said he was well paid.”

My mother retrieved the store ad and the Style section of the paper from her purse. “Just look at that,” she said.

“It’s a pretty picture of him in a sun dress. That can’t be all there is too it.”

“Look at what that Annette wrote about him on the runway in the fashion show. I was there, and I saw it all. I was never so embarrassed in my whole life,” my mother said.

“Why were you embarrassed? Did they announce that he was a boy and your son. Did anyone connect that he was your son?”

“No, that wasn’t it,” my mother said, “It was the way he carried on while on the runway. It was shameless, it was almost immoral. Look at the way this Annette person described it.” She handed Dr. Devlin a copy of the column.

Dr. Devlin read it and looked at me. “Did you really ‘strut your stuff’ and have sexy moves”?

“Maybe a little, but the audience loved it as well as the manager of the store.”

“How about you?” Dr. Devlin asked me, “did you like doing it?”

“I did,” I answered, “I felt so connected with the audience. I want to keep doing modeling, not only for the money, but for the pleasure it gives me.”

“Do you feel that you really are a girl inside?” Dr. Devlin asked me.

“Sometimes, maybe most of the time.”

“Well, I don’t want him to feel that he is a girl,” my father said, “inside or out. I want him to stop wearing female clothes as long as he’s living under my roof.”

“You mean you’d kick him out on the street?” Dr. Devlin asked with astonishment.

I was frightened and began to cry before my father could answer Dr. Devlin’s question. I wondered where I’d go if I was out on the street. My mother moved over to me and tried to comfort me with a hug. I pushed her away. “You don’t love me. You don’t want me to be your child.” I said between sobs. Now my mother started crying uncontrollably.

Now it was plain that everyone was upset. My father must have realized the consequences of what he had said. After a few minutes of crying filling the room, my father said, “I didn’t mean I’d kick him out in the street. I withdraw what I said.”

It is very difficult, if not impossible, to retract what has been said, and I continued to cry. My mother seemed to have recovered somewhat, and said, “Maybe we ought to go home.”

‘Home,’ I thought, where was my home? Did I still have one? Where would I go? Should I just marry Becky and the two of us find a place to live? I had some money saved for college, and we could survive if I dropped out of school and got a job. Could I continue working as a model? Alternatively, would Stephanie take me in?

By now I was curled up in a fetal position and hugging my legs. I was still crying. My mother stood up and put her hand on my shoulder. “Come on, Honey, let’s go home,” she said.

“Home?” I sobbed, “do I have a home?” I didn’t move. “Why don’t you and Dad go and leave me alone?”

Dr. Devlin was visibly upset at possibly having witnessed the breakdown of a family. “Roy, you shouldn’t be left alone. Go with your parents. I’m sure you will feel better in a while.”

“Okay,” I said, and stood up. My parents and I then left for home.

Amy was sitting at the kitchen table when we arrived. She took one look at me and asked, “What’s wrong?” I didn’t answer her, instead I went upstairs to my room. Amy followed close behind me.

Once in my room, I curled up on my bed and started to really cry. “What happened?” Amy asked. I was crying too hard to answer her. She sat on my bed and hugged me. We stayed that way for some time. Finally, I put on my pajamas and climbed into bed.

Saturday, February 6, 2016

I hadn’t eaten anything the night before, and after a restless night I was hungry. It was very early when I made my way to the kitchen to fix myself some breakfast. Amy must have heard me, and came into the kitchen and sat next to me. She put her arm around me, and asked, “What happened? I asked Mom and Dad, but they wouldn’t tell me. Whatever it was, it had to be bad, because both of them were really upset.”

“It looked like Dad wanted to kick me out of the house.” I said.

“Why?”

“Because I cross dress.”

“I thought that issue was resolved,” she said.

“So did I, but Mom was really ticked off about the fashion show, and Dad wanted me to stop dressing. He said he didn’t want me dressing under his roof. Dr. Devlin asked him if he’d kick me out, but before he could answer, everything went bad.”

“Are you going to stop dressing?” she asked.

“I guess I’ll have to, or face the consequences.”

“What consequences?”

“Find a place to live or someone who would take me in until I graduate.”

“If you stopped dressing you couldn’t do any modeling, could you?”

“That’s about it. I really need the money if I hope to go to college.”

I had finished my breakfast, so I stood up and said. “I’m going upstairs and get dressed, as Roy. Then I’m going out all day. I really don’t want to see Mom and Dad right now.”

“You’re not going to do something stupid are you?” Amy asked with a bit of fear in her voice. “You’re my only sister, or brother as the case may be, and I can’t imagine life without you.”

“Nothing stupid.” I reassured her. I just need time to sort out my thoughts.”

After kicking around all Saturday, I went home and immediately went to bed. When I was in bed, my mother knocked on my bedroom door. “May I come in, Honey?”

“I’d rather that you and Dad just leave me alone,” I answered.

“But your father and I am worried about you,” she said.

“I’ll be okay. Just leave me alone.”

“But you didn’t have anything to eat,” she added.

“I’m not hungry. I just want to be alone.”

“Amy’s worried about you. Will you talk with her?”

“Okay,” I answered.

It was not long before Amy came to my room. She sat on the bed and rubbed her hand on my shoulder. “Mom and Dad are really worried about you, and Mom is upset with Dad. Dad appears to be very sorry about what happened at counseling. By the way, Dr. Devlin called. She seems to be worried about you, Mom and Dad. Won’t you come downstairs and least talk with the folks a bit?”

“Not today, maybe tommorow.” I said.

“You know, feeling sorry about yourself doesn’t do anyone any good. Promise me you’ll talk to them first thing tomorrow morning?”

“Okay, I promise.”

Sunday, February 7, 2016

So on Sunday morning the whole family sat down around the kitchen table. My dad spoke first. “Roy, I’m really sorry what I said on Friday. It just came out, I wasn’t thinking. I want you to know that your mother and I love you deeply, and we would never kick you out of the house, no matter what you decide to wear.” He decided to lighten things up a bit, and said, “I looked at those pictures, and you looked really pretty, stunning in fact.”

This caused me to smile, and I said, “Thanks Dad.”

Then it was my mother’s turn. “I’m sorry I was upset with you. I now realize you were doing what you were hired to do. You were acting a part, and I might add doing it well. Your dad and I love you deeply, and regret upsetting you.”

“I’m sorry for upsetting you and Dad,” I responded.

We all stood up and had a group hug. My mother must have believed that the issue was resolved, because she decided to change the subject. “Have you talked with Becky recently?” Valentine’s Day is only a week away. Are the two of you going anywhere for it?”

“I asked her, but she doesn’t feel up to it, so I’ll probably just spend time with her. She wants to work ahead on her school work, so she won’t fall too far behind when the baby comes.”

“The baby is due in about a month, right?” my dad asked.

“Yeah, the due date is March 18th.”

“Has Becky or her family heard anything from the father?” Dad asked.

“Not a word.”

“Is she taking Lamaze classes? Amy asked.

“She couldn’t get into a class until one that starts this week, so there is a good chance that she’ll have the baby before the classes are completed, but something is better than nothing,” I answered.

“Does she have a partner for the class, since the father is not in the picture?” Amy asked.

“Yeah, and guess who,” I answered.

“They’ll think you’re the father,” my mother commented.

“Let them,” I said, “It doesn’t bother me.” I thought that it wouldn’t happen if I showed up as Renee for the classes. However, this was the wrong time to bring that up.

“How about her school work after she has baby?” my father asked.

“It’s already arranged. I’ll pick up the assignments from the school and bring them back when she does them,” I answered.

“How about tests?” Amy asked.

“I’m not sure, but I imagine they have figured it out. After all, Becky’s not the first girl to get pregnant while in high school.”

We discussed babies for a while. Then my mother suggested that I bring Becky over to visit, which I did. Becky’s mother came along with Becky and the three of them talked ‘baby’ for the rest of the morning.

During lunch I said that Becky and I were going shopping for baby things. That was not exactly how it worked. Both Becky’s mother and my mother invited themselves to be part of the excursion.

My dad found this humorous. “You’re on your own. You’ve got three females to deal with. I expect that your job will be to carry the purchases.

When we got to the mall, there was one fly in the ointment. At the department store, my picture as Renee the model was plastered all over the place. Thankfully, no one mentioned it.

Thursday, February 11, 2016

At the first Lamaze class, everyone assumed that I was the father. I could live with that, since I never expected to see any of our classmates after the baby was born. Mrs. Maynard, the Lamaze instructor, made a point of getting acquainted with all of the participants. “You’re Becky Jones,” right?” she asked. Without waiting for a reply, she consulted her class list, and continued, “and you’re Roy Evans?”

“And you’re the father?”

“No,” I answered. “I’m just a friend.”

“Then where is the father, and why isn’t he here?”

“We’re not married, and he denies paternity,” Becky said.

“Oh.” was all Mrs. Maynard said.

There was a lot of information provided at the class, including what Becky could expect in the near future, all the way through the actual childbirth.

During the class, Becky squeezed my hand and said, “I wish Renee was here.”

“Yeah, but too many people recognize Renee,” I replied, “You’re supposed to be the center of attention, not me.”

“You’re so sweet,” Becky said with a smile.

Saturday, February 13, 2016

It was about 4:00 when Joe called. “I’ve got a problem.” he stated.

“And what might that be?”

“Sue.” He said, and then added,” She’s ticked off at me, and wants to break our date.”

“Why?”

“She claims that I’m seeing someone else.”

“Are you?” I asked.

“No, except for you.”

“Oh great,” I said sarcastically, “so now I get to be ‘the other woman’ when I’m not even a woman.”

“If she won’t go out with me, maybe you would, as Renee?”

“What, did you take extra ‘stupid pills’ this morning? If Renee went out with you, it surely will get back to Sue, in which case she will dump you.”

“So what can I do?”

“Act contrite and swear that there is no other woman. A dozen roses wouldn’t hurt.”

“Okay, I’ll try that. Thanks,” he said and ended the call.

With one problem solved, another one manifested itself. Amy came barging into my room wearing only a bra and panties. “I need your help!” she declared, and then explained, “I’ve got a hot date tonight, and I’ve got nothing to wear!”

“Let me guess,” I said, “the fashion police pulled a raid and confiscated all of you clothes?”

“Very funny,” she said sarcastically, and then walked over to my closet. “Where is that dress you wore for the nightclub photo shoot?”

“I think that Mom thinks that it is too immodest,” I suggested.

She ignored what I said, and started pawing through my closet until she found what she was looking for, and took it out of the closet. “Thanks,” she said as she breezed out of my room.

A half hour later the door to my room was still wide open and I heard my mother’s voice loudly saying, “Amy, that dress is too revealing. I don’t want my daughter to look like a street walker.”

“But it’s okay if your son does?” Amy loudly declared. I shut the door to my room so I didn’t have to hear the rest of their conversation, but what I had heard made me smile.

I didn’t have any wardrobe issues that evening. I was dressed as Roy, and I was going over to visit Becky at her home. Being close to eight months pregnant, Becky didn’t want to go out.

Sunday, February 14, 2016

I had signed up for a full day working at the shop, and after a shower I put in my corset and red hose. I followed that with a red skirt and blouse combination and went downstairs to have some breakfast before I left for work.

Both of my parents were sitting at the kitchen table reading the paper. After a few minutes, my father said, “Disgusting!”

I had an idea what had caused his statement, and decided to say nothing. My mother was not so restrained. “What is it dear?” she asked.

“Look at these ads.” he said as he handed my mother a section of the paper. While he did this I caught a glance of two ads; one for the nightclub and the other for the department store. Both contained my picture.

“Oh my,” she said as she handed the paper back to my father. She then turned to look at me with a very displeased expression on her face.

“I thought we were done with this nonsense,” my father said.

I felt that I had to say something. “My modeling contract allows them to use my image for print ads for a year, provided they pay the agency and me for each use. Think money.”

“Even if they pay you, I still don’t like it,” he responded.

I finished my breakfast in silence and went back to my room to put on my makeup and do my hair.

When I arrived at the store, the first thing I noticed was that someone had cut the nightclub ad out of the paper and stuck it on a piece of cardboard which said, ‘The dress in this ad was purchased here,’ and also said, ‘The model is our own Renee.’

Ms. Shay came over to me before I even had a chance to hang up my coat. “Mrs. Bates wants you to call her,” she said, “She has some modeling jobs for you. I told her that they were okay with me.” When I took off my coat, Ms. Shay looked at me with a smile. “I like your outfit; very appropriate for Valentine’s Day.”

I called Mrs. Bates. “Coffrey’s department is putting together its on line catalog and wants you to be one of their models. How does that sound?”

“I’ll have to check it out with Ms. Shay,” I answered.

“I already did, and she said it’s okay with her.”

The store was not busy, so in mid-afternoon I left to spend the rest of the day with Becky.

Monday, March 21, 2016

Nothing happened on Becky’s due date, or the next two days. Becky and I were sitting next to each other in history class when I heard her gasp. “Are you Okay?” I asked her.

“It’s starting,” she said.

“What?” I asked.

“What do you think it is?” she said retorically. “I just had a contraction.”

A few minutes later, she grabbed her purse and ran from the classroom. All of this did not escape the notice of Mr. Bryce, the teacher. “Would someone tell me what’s going on? If it’s more important than the history lesson, maybe you’d like to share it with the whole class,” he said with a sneer. He didn’t have a clue.

“She just had a contraction,” I said. I knew all about this from what I had learned in Lamaze class.

“A contract what?”

“A contraction,” I said.

“So?” With this most of the girls started to snicker at Mr. Bryce’s ignorance.

“She’s having a baby!” I announced.

“What? Having a Baby? Here? Now?” he stammered, with fear written all over his face.

“I hope not here,” I reassured him, and added. “And from what I learned in Lamaze class, not right now, but soon.

“Why did she run out of class?”

“I don’t know,” I answered. “Maybe her water broke. I’m only guessing.”

“What are we supposed to do?” he asked.

“Get her to her doctor or maybe the hospital,” I suggested, “or failing those, at least have the school nurse see her.”

A few minutes Becky came back into the classroom, and sat next to me. “My water broke,” she whispered to me.

“Yeah, I figured it might be that.” I said, “What do you want to do? Go home? See your Doctor? Go to the hospital? See the school nurse?”

She glanced around the room and noticed the curiousity and concern on everyone’s faces. She smiled, with a wicked smile, and said, with all of the fake innocence she could muster, “I’ll stay here for a bit. I just can’t stand the suspense. I just have to know if the Missouri Compromise was successful,” referring to the history class topic of the day. Everyone, except Mr. Bryce, laughed loudly.

When Mr. Bryce regained some control over the class and his own composure, he said, “Miss Jones, maybe you should see the school nurse. She can sign you out from school and you can go wherever you need to go. Is there anyone who can pick you up?”

“Roy gave me a ride to school and he is my Lamaze coach, so maybe he could take me to the nurse and then home or whatever,” she said.

Mr/ Bryce was visibly relieved that the problem was in someone else’s hands, and wrote notes to see the school nurse. As we were getting ready to go to the nurse, I picked up my backpack and Becky’s books. When she saw me doing this, she declared, “I’m not an invalid, I can darn well carry my own books. After all I’ve been carrying this for quite a while,” and she patted her belly.

As Mr. Bryce handed us our notes, he said, “You’d better get along,” like he thought the baby would pop out in the next thirty seconds and start asking searching question about the Missouri Compromise and other events leading to the American Civil War.

As we passed a girl’s washroom on the way to the nurse’s office, Becky stopped me, and said, I’m glad I’ve got some pads with me. I’ve been carrying them with me for the last few weeks. I’m beginning to squish and I want to change my pad.”

She handed me her books, and said, “Here, make yourself useful while I visit the restroom.”

She paused for a moment, and then said with a smile, “Too bad you’re not Renee today. If you were, you could go in and help me.”

When we arrived at the school nurse’s office there were a number of students in the room, no doubt trying to convince the nurse that they really were sick in order to avoid taking a test scheduled for the next period.

The school nurse was an older woman with a stern visage, having dealt with malingerers for many years. She looked at Becky and me with a frown. “And what’s your flimsy excuse for being here?”

I handed her the notes from Mr. Bryce and said, “She’s started contractions and her water broke.”

“And what makes you an obstetrician?” she said scathingly, “Can’t she talk for herself?”

“I can,” Becky said, “and Roy is correct. We’ve been going to Lamaze classes together.”

The stern look on the nurse’s face diappeared. ‘How often are your contractions, Honey?”

“I just had one and . . . .” Becky said and gave a sound of pain.

“Another one?” said the nurse. Becky could only nod her head.

“I gave Becky a ride to school,” I said, and then added, “Becky’s mom’s car blew a brake line, and she can’t pick her up, so I’ll be the one to take her home and wherever the Doctor directs us to go.”

“I’m not supposed to release a student to another student, but this is kind of an emergency,” the nurse said, and added, “I presume that you’re the father?”

“No,” I answered.

“They all say that,” she commented. “Well a DNA test will resolve that issue,” she concluded, and signed us out of school.

While in my car on the way to her house. Becky called her mother and explained what was going on.

Becky’s contractions were coming more often and were more severe. The Doctor said that we should go to the hospital directly after picking up Becky’s mom. Upon arrival, Becky was examined, and it was determined that while she wouldn’t give birth right away, it was best to keep her until she was ready to deliver.

A nurse entered the room. “Will you have anyone with you in the delivery room?” she asked.

“I have a list,” Becky answered, and handed it to the nurse.

Becky turned to me and said, “I put you name on the list as ‘a friend.’ along with Renee’s name. Too bad Renee can’t make it.”

The nurse turned to me and asked, “And you’re the father?”

“No, but I am her Lamaze coach and partner,’ I said, “the father won’t be here at all.”

The delivery was, well, a delivery, with lots of blood and stuff. At one point, during a painful push, Becky yelled, “I hate you Chad!”

“Who’s Chad?” the nurse asked.

“The father,” I answered.

The nurse nodded her head knowingly and smiled.

In the end, Becky delivered a beautiful and healthy baby boy. I even got a chance to hold him and coo baby sounds to him.

“Too bad he’s not the father,” the nurse commented, “He looks like he’ll make a wonderful daddy one day.”

Becky’s mother responded. “He will. I only wish that he was the father.”

Tuesday, March 22, 2016

At school the next morning, everyone had heard about the events of the past day, and crowded around me for ‘details.’

“What did you name the baby?” was the main question. I had an answer prepared.

“Since Becky’s first contraction began in history class when we discussing the Missouri Compromise, I suggested that Becky name him ‘Missouri Compromise Jones.’ However, she said that people would shorten his first name to ‘Miss’ as a nickname, and people would call him ‘Miss Jones.’ Becky rejected my suggestion as causing too much gender confusion, so in the end Becky reversed the father’s first and middle names, so his name is Robert Chadworth Bereston.

“Were you in the delivery room?” was a common question.

“Yes, after all I was her Lamaze coach.”

“Was it gross?” a girl wanted to know.

“Not really.” I answered,” the miracle of birth can’t be considered to be gross.”

After school I went to the hospital to visit Becky and admire the baby. During my visit, Becky said, “I was hoping that Renee would visit me and the baby. You know that both you and Renee are on the approved visitor list.”

Becky’s mom heard this. She knew of the problems my parents had with Renee. “Becky would really like to see Renee,” she said to me, and she laid out a plan that I would go to the Jones’ house, change into Renee, visit Becky and little Robert, and return to the Jones’ house to change back to Roy.

Wednesday, March 23, 2016

I instituted the plan laid out by Becky’s mother, and Renee went to visit Becky and the baby. It should have been simple, but that is not what happened. Although my name was on the approved list, one of the girls at the nurse’s station recognized me as the model. “Oh my,” she delcared, aren’t you that famous model for Coffrey’s Department Store?” I had to admit that I was, but added. “I don’t consider myself to be famous.” This drew a crowd of hospital staff. One of them referred to the list and noted that there was a Roy Evens and a Renee Evans on the list.

“A boy named Roy Evans visited yesterday,” an aide said. “Are you related to him?” she asked.

“Distantly,” I answered. Well, ‘distantly’ is hardly a precise word, and I didn’t consider it too be too much of a lie, since there was a distance; the distance between a training bra and a ‘C’ cup. I felt that being sociable was proper and they peppered me with questions and comments until a supervisor saved me when she ordered my adoring group to get back to work.

Becky was very happy to see me as Renee, and, frankly, I was happy to be Renee, even for a short time.

Wednesday, June 1, 2016

Graduation. At last. It turned out that Becky returned to classes by mid-April. I had brought her class assignments to her each day and returned the completed class work the next day. She hadn’t missed anything and her grades were excellent. Becky’s parents and the baby attended the graduation, and the baby was the center of a lot of attention.

Naturally my parents and Amy were there. I was dressed in a suit, as Roy.

Shortly before graduation DNA tests were performed which proved that Chad was indeed the father of little Robert.

There was talk about a wedding. It appeared that Chad’s mother wasn’t going to be denied her grandson.

Sunday, July 3, 2016

Becky and Chad were married on the Sunday of the July 4th weekend. It was a small wedding, and took place in the town where Chad lived. Only the parents of the bride and groom were there, along with close relatives and friends, about thirty people in all. Sue was the maid of honor, and nothing would do but to have Renee as the only bride’s maid. Since I was standing up for the wedding, my parents were invited. Joe was there as Sue’s boyfriend.

Me being Renee the whole weekend caused a lot of problems with my parents. It was only by the intervention of Becky and her mother, that they grudgingly agreed to attend with me as Renee. Becky’s clinching argument was that once she was married, she and I would be separated by distance.

I was fortunate in that I had done modeling of bridal fashions and I had a lovely pink dress with a chiffon overlay over the skirt and lace on the top. It was strapless but came with a short jacket to cover the top. Becky and her mother thought it looked ‘devine.’ My parents grudgingly said it was ‘okay.’

And then there was Joe. Even though he was with Sue, he made it plain that he would like to do things to me. While Sue and I shared a hotel room, Joe had a single room. Sue unwittingly came to my ‘rescue’ when she whispered to me that she would not use our hotel room both nights. My problem was that I didn’t want to be ‘rescued.’

The wedding reception was held in the church recreation hall, and a DJ provided the music. Since I was dressed as Renee, Joe insisted that I dance with him. I enjoyed dancing with him, even if he whispered lewd suggestions to me and had his hand on my behind some of the time. In fact I really enjoyed my weekend as Renee, and was able to dance with the best man and the groom’s man.

Perhaps it was all of the fun I had that on that weekend that I decided that I really wanted to be a girl. After all, I had, in the past, contemplated marrying Becky, but now that she was married, that was no longer possible.

Friday, September 2, 2016

I had previously told my parents of my decision to become a girl. I had enrolled in college as Renee. While my parents were very unhappy with my decision, they didn’t try to stop me.

I had a session with my counselor, where I confirmed my decision. I had started hormone replacement therapy and my counselor told me that I would have to live as a female before anything permanent could be done. I accepted that and announced that my year real life experience would start on the day after Labor day. Only time would tell how that would work out.

I decided to update the essay which had started me on the road to womanhood, with today being the final entry into Roy’s journal.

SARAH Part 1 of 5

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression
  • Sweet / Sentimental
  • Voluntary

TG Elements: 

  • High heels / Shoes / Boots / Feet
  • Performer/Entertainer
  • Shopping

Permission: 

  • Posted by author(s)

SARAH Part I of V

By Pentatonic
Edited by Commentator

Chapter 1 - The Substitute

My name is George and I'm a quite good musician having studied piano for ten years, and sung in the church youth choir for the last five years. In addition to my music, I like to run. I run cross country and the mile and was good enough to make the teams and earn a letter. This labeled me as a “Jock,” as funny as that might seem. A great thing is that being on school teams meant that I avoided regular PE classes and the school bullies. I had made music and cross country my whole life.

At the start of my sophomore year in high school I was only 5' 8" and weighed 125 pounds dripping wet. I had yet to develop and I didn't really need to shave. I had a runner's body with the exception of my butt. It is a family trait that the males have bigger than usual butts. I had shoulder length hair that I would put in a ponytail at my neck.

My voice had not yet cracked and I sang soprano. With all of my practice I had a very good vocal range; about three octaves.

I didn't have any close male friends, my closest friends being Ashley and Kimberly who, like me, were sophomores. We attended the same school and all sang in the youth choir at church. Ashley, Kimberly and another girl named Sarah had signed up for our school's Talent Show which was held every spring to sing three part harmonies like the Andrews Sisters or the McGuire Sisters. Yes, the music was really dated, but they sounded really good. I was their piano accompanist and did the musical arrangements.

A problem evolved as Sarah had to drop out of the trio when her father was transferred to a different city. After Sarah's departure, Ashley, Kimberly and I were practicing our music and trying to figure out a replacement for Sarah.

“You know, George could take Sarah's place. He would make a very good looking girl,” Ashley posited. “ He knows Sarah's parts and does a great job singing them in practice.”

“No way! I'm not doing it,” I shouted. “People would point their fingers at me and laugh.”

“No, they wouldn't,” rejoined Ashley. Kimberly just looked at me with a funny smile.

“But I'm the accompanist,” I argued.

“That's not a problem. It's easier to get someone to play the piano than it is to find a replacement singer. I'll speak with Mrs. Benson, I'm sure she would be happy to accompany us,” Ashley countered. Mrs. Benson was the youth choir leader at our church. Oh great, I thought, if I sing as a girl I'll never be able to show my face in church again.

“That's a great idea,” Kimberly added.

“Well I don't think so,” I replied.

We were in Ashley's living room when this happened. My strong objections had drawn Ashley's mother into the room. “What's the problem?” she asked. The girls explained the situation and Ashley's mother stared at me, as if sizing me up. She called her Aunt Jane into the room and told her of the problem.

“How tall are you and how much do you weigh?” Aunt Jane asked, looking me up and down.

“About 5' 8" and 125 pounds," I replied, "Why do you ask?” I didn't get an answer, instead Aunt Jane asked me to take my hair out of the ponytail, to stand up and to turn around. I did as asked, perhaps a bit too quickly, because turning caused my shoulder length hair to swirl around my head.

“Nice hair,” Aunt Jane said, “now turn around a little slower.” After I did a slow spin nothing was said for a brief time.

“I remember seeing George singing with the church choir,” Aunt Jane said. “With his choir robes, the collar, the bow and his long hair, I thought he was too cute to be a boy. I think that the same holds true now. He could take Sarah's place.”

I didn't like this at all. It was bad enough that a lot of boys in my school thought that I was rather effeminate. Going on stage and performing as a girl would really seal my fate. I wouldn't dare show my face in school after that.

“I'll be laughed out of school, or worse, if I did this,” I complained.

“We'll call you Sarah, since that is the name on our application. We won't use your name. You can get a wig. No one will recognize you,” Kimberly said.

“I'm not sure about that. Furthermore, I don't think my parents, especially my dad, would want me to do this,” I added in objection to their proposal

“How do you know? You haven't even asked them.”

“I know my dad. He wouldn't like it if I dressed and sang as a girl.”

“It's not like this will make you gay or something,” Ashley said.

“Anyway, I'd just look stupid, like a boy in a dress,” I argued.

Ashley just looked at me, sizing me up. “No, I don't think so, I think that we can make you look like a real girl,” she said. “Anyway, it's not like we are likely to win anything since our songs are real oldies and none of the kids are likely to have heard or like any of them. Once we are finished, everyone will forget about us.”

“George, I think the girls are right. You could do it,” Ashley's mother finally said.

The problem was that she was probably correct. My hair was on the long side. Despite all of my running, my butt was larger than average. I had been mistaken for a girl more times than I wanted to remember.

“George, why don't we have your parents and Kimberly's parents over on Friday evening and all of us will discuss it,” Ashley's mother suggested.

Oh great. I had hoped to ask Ashley for a date on Friday evening. Having a parental discussion about me wearing a dress was an extremely poor substitute. The girls, on the other hand, were ecstatic. However, I felt confident that my dad would not permit me to do this, so a meeting was in my best interest.

I put some thought into what I would wear on Friday. I decided that a button-down oxford shirt, pressed slacks, and penny loafers would be a good idea. I tied my hair in a low ponytail at my neck. I tried to look as male as possible and the opposite of “cute.” I looked in the mirror before I left home and liked what I saw, even though it might still have been a bit “cute.”

That evening Kimberly and her parents, Ashley and her parents, along with her great-aunt Jane, and my parents and I were all at Ashley's house. Ashley explained the problem.

“We want George to sing as Sarah in our trio. We can't have George sing as George, since most of our songs are ‘girl’ type songs and it wouldn't be right to have a boy singing them.” Ashley explained.

It was time for me to make a rebuttal. “Rather than me singing, I think that the best idea is for me to rearrange the music for a duet,” I said, happy with my idea. “After all, I did all of the arrangements for the three parts and the accompaniment.”

“Wouldn't that be a lot of work?” Kimberly's father wanted to know.

“It would be a bit of work, but I can do it,” I said with certainty.

“But wouldn't that change the voice parts? It would be hard for Ashley and me to learn new parts,” Kimberly said. Unfortunately, she was right.

“I d rather not do it at all than to do it as a duet,” Ashley pouted. With that statement, I could see the possibility of future dates with Ashley going down the drain if I didn't agree with her.

“That would be a shame,” said Ashley's aunt. “I've heard you practice, and I was really looking forward to hearing you sing the songs at the show.”

“Why don't you do one of the songs?” Kimberly's mother suggested.

We retreated to the kitchen to prepare.

Ashley's mom did the introductions as we walked into the living room. I went to the piano and I played and sang the verse of “Someone to Watch Over Me” which is an exclusively girlish song. Ashley and Kimberly came in on the chorus. I had previously suggested that Ashley or Kimberly sing the verse, and that I only accompany on the piano, but my suggestion was rejected, so there I was singing my heart out for some man to watch over me.

We finished the song. Not a sound was heard for a few seconds, but then everyone began to applaud. Kimberly, Ashley and I curtsied; why I curtsied I have no idea, but when I saw Kimberly and Ashley do it I just joined in. That probably was a mistake on my part because it made me look really girlish.

We sang two other songs to greater applause. When we finished, we sat down and Ashley's mom stood up. “I invited all of you so you could hear our children sing.” Thankfully she used the word “children “ and not “girls” as she might have done.

“We had Sarah as a member of the trio,” she continued, “and George would play the accompaniment. Sarah had to drop out suddenly, and we’re one girl short. After hearing George pour out his heart for a man to ‘watch over me’ you can see why we suggested that George become Sarah for the Talent Show.”

I looked over at my dad to gauge his reaction. He was smiling and nodding his head in approval. Not a good sign for me. My mom was just beaming. No help there.

Ashley's mom looked around the room. “To make this work, George has to become a girl for the performance. I realize that some of you might object to this, but I wanted you to hear the singing before making any decision. I would like to turn this over to George's dad, for his opinion.”

My dad just sat there for a moment, until my mother leaned over toward him and said the word “Follies,” followed by the name of my father's college fraternity. She obviously knew something about this since she and my dad were in college together, and got engaged while in college. My father gave a weird look at my mother and began to speak.

“This is a bit unusual and I haven't discussed it with my son, but I have no objection. He actually may enjoy it.” My mother just beamed. “George,” my father continued, “you realize that you and the girls have put a lot of work into this, and if you don't go through with it all that work would be wasted and two wonderful girls would be disappointed.” Talk about guilt trips.

Neither Kimberly's parents nor Ashley's parents had any problem with me being Sarah for the performance. Ashley's great-Aunt Jane enthusiastically supported the proposal.

I played my last card in my attempt to get out of this. “But if I sing, we will be short an accompanist.”

Like all of my other objections, this didn't work. “I spoke with Mrs. Benson about this today, and she is willing to accompany us,” Ashley interjected. "The Talent Show rules would permit this."

“I realize that going through with this will involve some expense,” Aunt Jane said. “I am willing to fund this project; a beauty salon, make over, hair, clothes, etc. and pay Mrs. Benson. Kimberly, Ashley, I leave it up to you to instruct George, now Sarah, how to present himself as a girl, the walk, expressions, body movements and the like, between now and the show. I am really looking forward to the Talent Show.”

“Don't get too excited, Aunt Jane, it is not likely that we will win or even come in second or third,” Ashley cautioned.

My father looked directly at me. “It's all up to you, George. Will you do it?”

My last hope for an easy escape was gone, once my father had raised no objection. I looked around the room, especially at Ashley and Kimberly, and then lowered my head in thought. After a long pause I raised my head. "I'll do it," I finally said.

Ashley and Kimberly jumped up, hugged each other, and began to squeal with delight. They reached over to me, pulled me to my feet and the three of us hugged each other.

After a few other details were worked out we all headed for home. How am I going to pull this off, I wondered?

When we were back home, my mother came to me and said that I was very brave agreeing to perform as a girl and that she was very proud of me. “There is something that I want to show you,” she said, and pulled out an old photo album. She turned to some photographs of a really pretty girl. “When your father was in college, his frat had a show called the Follies. There were girl parts but no girls in the show. All of the girl parts were played by the boys in the frat.” She pointed to the photo. “Look familiar to you?” she asked. I studied the photograph.

The pretty girl had the same kind of smile that my father had. “Dad?” I asked.

“Your father as a girl,” my mother confirmed. “I reminded him of this before he said something stupid tonight,” she added.

I continued to look at the picture. I hoped that I could look as good.

When I went upstairs to bed, my mother met me, and handed me one of her nightgowns. “Might as well get started right now, Sarah,” she said with a grin.

That night I slept as Sarah, in a nightgown.

Chapter 2 - At The Mall.

The next day was Saturday, and at an ungodly hour of the morning, my mother pulled me out of bed. “Get up, Sarah, we have a lot to do and not much time to do it in.”

“Sarah? Who's Sarah?” I mumbled, wondering why I was wearing a nightgown instead of my usual pajamas.

“You are, dear.”

“Oh,” and it all came back to me. I stood up, and the hem of the nightgown slid down. I ran my hands down the smooth softness of the nightgown.

She pulled out a measuring tape and began to measure me all over my body, including some places where I wished she wouldn't. Oh well, that's the way mothers are, I thought.

“Quit fidgeting,” she commanded. “Remember I've seen you naked more times than you can recall,” and she kept measuring.

After she put down the measuring tape, she said, “I have to run some quick errands. In the meantime, go take a shower, but before you do, you will find some hair remover on the sink. Read the instructions, and put it everywhere except on your head. When I come back from my errands, I expect you to be out of the shower and in this robe.” She handed me one of her robes. It was pink. I just grunted a reply and she left my room. A few minutes later I heard the car starting.

After the hair removal and the shower, I was sitting at the kitchen table in a pink robe, contemplating the mess I was in. My father strolled into the kitchen and poured himself a cup of coffee.

“Follies?” I asked.

“Yep,” he replied.

“Why?”

“Because the frat had done it for years, and everyone expected us to do it. I got chosen to be a girl because of my size, and like you I have a good voice. I could sound something like a girl.”

“Did you like it?”

“Yeah, I met your mother because of the show. She liked my dressing up, and that led to our marriage. So, in a way, you are a product of my dressing like a girl.”

“Mom said she was running some errands. You know anything about that?”

“Not really, but I can guess, and it’s my guess that it has to do with Sarah.”
I only grunted a reply and stared at the walls until my mother returned.

Mom strode into the kitchen, carrying some bags. “I'm glad you followed my instructions. Time for us to go up to your room, Sarah.”

That name again. Yuck!

When we got to my room, my mom reached into one of the bags and pulled out a package with three panties. She opened it and pulled out a peach colored pair. “Here, put these on and tuck your . . . you know what, back between your legs. When you're done, take off the robe.”

I did as I was told, and she handed me a peach colored bra. “Here, put this on. It matches your panties. A girl feels better when her bra matches her panties.”

“I'm not a girl, remember, so I don't feel better when my bra and panties match. In fact I don't feel better wearing a bra and panties. And why are they now ‘my’ bra and panties?”

“Oh just get on with it,” she retorted. “I got you a padded bra, to give you a little shape.”

My mother began to look wishful. “Oh gee! I just remembered that buying a daughter her first bra is an important mother/daughter moment. Sorry I cheated you out of that, but I didn't think that you would want to go into a store looking like a boy to buy a bra.”

“Gee, thanks,” I said sarcastically.

“Once we get you into girl mode, I can take you with me when we shop for more clothes.”

“I can hardly wait,” I said, my voice dripping with sarcasm.

“I'm only trying to help,” she said. “I don't want someone to look at you and say ‘A boy in a skirt’.”

“Okay mom, I'm sorry.”

“It's okay.”

“Let me see how that bra fits,” she said, coming over to me and pulling and pushing on the bra. “Looks pretty good, I measured you correctly.”

“Put on this top and skirt,” she said, handing the items to me.

I put on the top. It was just like a T-shirt, but it was, as I later found, to be lilac. I then stepped into the denim skirt, and pulled up the zipper.

“The zipper goes in the back,” she said in a helpful tone.

I twisted the skirt around. “Take a look in the mirror to make sure the zipper is in the center of your back.” I did as she said.

“It's a good thing that your butt is on the large size. It fills out the skirt,” she added. I, for one, did not think that the size of my butt was a good thing.

“Why do I have to wear a skirt? Most of the girls I know wear jeans.”

“Girls’ jeans are cut differently from boys. The waist is smaller and the hips larger. We have to go to the store and try them on to make sure they fit. I got you a skirt since the fit is not as critical.”

“Why couldn't I just wear my own jeans?”

“Because they're boys’ jeans, and girls don't look good in boys’ jeans. Too tight in hips and too loose in the waist. If you wear jeans, you've got to wear girls’ jeans.”

I just grunted in response, not quite following her logic, or lack thereof.

“I got you some girl's athletic shoes. I hope they fit. You don't need any socks, unless they are too loose on you.” I put them on and they fit.

“It's 11:30 already. I called Kimberly and Ashley and told them to come over for lunch at noon to see Sarah.”

I just grunted a reply.

“By the way, you've got to stop grunting. Boys grunt, Girls don't.”

“But I'm a boy.”

“Not the way you're dressed.”

There appeared to be another logic error there, but I decided to let it slide.

Mom then said, “Since you're a girl, you have to help prepare lunch for the girls, and serve it.”

Oh great, I thought, I put on a skirt and I become an indentured servant.

At twelve sharp, the doorbell rang. “Get the door, Sarah,” my mother called from the kitchen.

I trudged to the door, wishing I was somewhere else. As I opened the door, I saw Ashley and Kimberly standing there with big grins on their faces.

“You look great,” Kimberly announced. “Lilac is definitely your color.”

The only color I wanted would be called “invisible.”

“Come into the kitchen girls,” mom called out. “Sarah prepared our lunch. I hope you enjoy it.”

“Sarah, please set the table.”

For some reason this caused a fit of giggles from the girls. I just frowned.

“Ooh! I can't wait to do something with your hair, Sarah.” Kimberly cooed.

“I get to do her makeup,” Ashley claimed, lifting a bag which, as it turned out, had a great quantity of makeup.

I put lunch on the table and flopped down in a chair. Mom and the girls immediately stopped talking and just looked at me, disapprovingly.

“That's not how a young lady sits down,” mom said in a chiding voice. “Smooth out the back of your skirt so it doesn't get wrinkled or ride up. Sit down slowly and sit on the front of the chair. Keep your legs together, don't give the whole world a look at your panties. Now stand up again, keep your knees together and try to gracefully sit down.”

“You've got a lot to learn by the night of the talent show,” mom added. “I hope we have enough time.”

I ate in silence, since Ashley, Kimberly and mom filled every second with talking about clothes, makeup, hair and me as Sarah. The word “cute “ was used more times than I thought possible.

“What's the program for today?” Ashley asked.

“You girls do something with her hair and makeup, and then we're going shopping,” mom interjected among squeals from the girls. I wasn't at all pleased with mom's choice of pronouns. “Let's get started. Sarah, just put the dishes in the sink for now; you can wash them later.”

After I cleared off the table and put everything away, mom and the girls led me upstairs to my parents' bedroom, and sat me down at mom's vanity. This time I tried to sit in a more ladylike manner.

Kimberly pulled the elastic from my ponytail and began attacking my hair with a comb and brush, painfully pulling out the snarls. “Ooh, you've got such nice hair. Too nice for a boy.” It was then that I discovered the joy of having someone brush your hair.

Ashley, meanwhile studied my face, like an artist looking at a fresh canvas. “It's a good thing that I brought some lilac eye shadow,” she said.

My hair is a little long for a boy, but perhaps not to long for a classical musician. Kimberly kept brushing it. She then stood back, and surveyed her work.
“Do you have a scissors?” Kimberly asked.

“Whoa!” I almost shouted. “No one said anything about cutting hair.” I could just envision the creation of a really feminine hair style that wouldn't be able to be disguised when I went to school.

“Oh stop being a baby,” said Kimberly. “I'm just going to get rid of split ends. No girl wants hair with split ends.”

But I'm not a girl, I thought, I can live with split ends.

My mother weighed in with her opinion, and I lost. The split ends, and more, were gone.

“But no bangs!” I stated with as much emphasis as I could muster, while wearing a skirt.

“Okay, no bangs,” they conceded.

“Maybe later,” Ashley whispered to Kimberly.

“I heard that,” I shouted.

“Okay,” Ashley conceded.

“You know a few highlights would look really cute,” Kimberly ventured.

“They would,” agreed Ashley.

I shouted, “I don't want to look cute. Everybody seems to like to apply that word to me. I've had enough of it.”

“But you are cute,” Kimberly said. I frowned. “Even when you frown,” she added.

I decided I needed an ally in what was becoming them versus me. “Where's dad?” I demanded.

Dad heard me, and he entered the room. “What's the problem?”

“They're trying to make me look cute,” I complained.

“Oh,” dad said, and then added, “That actually won't be too hard to do.”

I recalled the photos that my mother had shown me last night. With all the disgust I could muster, I spat out the words, “Blasted Follies.”

My dad just smiled. “You're on your own now. Maybe you'll learn that trying to argue with three women at one time is a lose-lose situation.” He turned around and walked out of the room. I was truly alone.

My mother looked at me in a way I didn't like. “You know, highlights would really look cute.”

“Mom, please!” I shouted. That word again.

“Okay,” she said.

Kimberly drew my hair into a ponytail. Not low on my neck, but high on the back of my head. Girl style. “Does anyone have a blue scrunchie? I think it would go well with her lilac top.”

“Her? Hey I'm a boy, remember that.”

“Yeah, Yeah, whatever,” was the reply.

While all the arguing about hair was going on, Ashley was smearing some stuff on my face. “What's that?” I challenged.

“Concealer and foundation,” was the response.

“Why?”

“Every girl applies concealer and foundation under her makeup. It covers imperfections and is the base for the other makeup.”

“But I'm not a girl. I don't have any imperfections,” I rejoined.

“How about that zit on your forehead?” said Ashley.

“Oh that.”

“Yeah, that,” said Ashley. “Anyway, I'm finished with the concealer and foundation,” she added, brushing some feminine smelling powder over the foundation.

“Do you think some blush is needed?” Ashley asked.

“Maybe a little,” was the response.

I got blush.

I felt a sharp pain at my eyebrows. "Ouch! What are you doing?”

“Just cleaning up your eyebrows a bit. Stop being a baby,” was Ashley's answer.

“Close your eyes,” Ashley commanded, as she applied some eye shadow. Lilac, naturally.

Next came eye liner and mascara.

Ashley produced a lipstick and began to apply it to my lips. By then, I realized that further resistance was futile, and just glumly sat there.

Finally, they were finished, and stood back to admire their handiwork, “You really look hot, girlfriend,” Ashley exclaimed. I looked in the mirror. I did look like a “cute” teen-aged girl.

Mom put on a coat and grabbed her purse and keys. She then handed me another coat, and said, “We’ll get you a coat at the mall that is more appropriate for a girl your age.” She then picked up and handed me a purse and said, “I already packed your purse.” It had my school ID, a hair brush, some tissue, and the tube of that lipstick. “Put the strap over your shoulder.”

“Let's shop, girls!” my mother announced. I was less than happy being referred to as one of the girls, but I said nothing. Kimberly and Ashley each grabbed one of my hands and began pulling me toward the open door. I think that they held my hands to keep me from escaping.

Once on the front porch, I became terrified. “What if someone sees me?”

“They'd only think that they saw a pretty girl,” mom said, trying to quiet my fears. It didn't.

My attempt to get into the car resulted in another “girl” lesson. “When you get into a car while wearing a skirt, turn sideways, keep your legs together, and when you are sitting swivel your legs in the car,” my mother instructed. “Ashley, would you show Sarah how to do this properly?”

Ashley just giggled, and, even though she was wearing jeans, demonstrated the proper way to get into a car. That caused me to note that I was the only one wearing a skirt. Three females wearing jeans, and the only male wearing a skirt. There seemed to be some kind of injustice here.

While mom was driving to the mall, I asked her, “Why are we going shopping?”

“Because you need some more girls’ clothes,” she responded.

“But I already have a skirt and top.”

“You are going to need to practice being a girl when not in school or church from now until the talent show,” mom explained.

“Bummer,” I muttered under my breath.

Mom pulled the car into the mall parking lot. I looked around. There were a whole lot of people around. “Mom, I don't know if I can do this,” I complained, being sure that everyone in sight would know that I was a boy in a skirt.

“Quit complaining, and let's go,” mom said.

While walking to the entrance of the mall, I could feel the cool breeze under my skirt and on my hairless legs. The hem rubbed my legs as the skirt swayed with each step. It wasn't totally unpleasant. The first store we entered was a big discount store. We headed directly to the woman's wear area. It was filled with all kinds of female attire. Mom strode directly to the lingerie department, followed by the girls and the pretend girl. Mom and the girls immediately began going through the piles of lacy and delicate undergarments.

“Do you see anything you like?” she asked me.

“No,” I replied, truthfully.

Mom looked at a lot of lingerie, checking them for size, “Here,” she said as she pushed a pile of ladies’ underwear into my arms. “Let's go to the changing rooms to see if they fit.” With that, she took my hand and began pulling me to the back of the store. Ashley and Kimberly just giggled.

After what seemed to be an embarrassingly long time, mom found three bras she liked, along with what I found out was a camisole, two half slips and one full slip. We walked out of the changing room, with me carrying my new clothes.

The next stop was the hosiery department, where I acquired three sets of pantyhose.

After paying for the purchases, we left the store, and mom led us to a store that seemed to specialize in what I soon found out were “foundation garments.”

A sales clerk approached us, and asked if she could help us.

“We need a waist nipper and maybe a padded panty girdle for my son,” mom flatly stated. This time I was not referred to as a girl, but for me this was the wrong time.

"MOM!" I barely kept from shouting.

“I see,” the clerk said. “We do get a number of gentlemen customers here, so I think I know what you need.” With this she gave me a broad smile, and winked at me. I was then fitted for a padded girdle and waist nipper. Before paying for them, mom told me to keep them on. She explained that they were necessary so the dresses would properly fit.

“Dresses?” I questioned. “The talent show is only for one night.”

“Yes, but you have to do a lot of practicing being a girl,” she retorted.

However, before heading off to buy dresses, mom steered us into a shoe store. “We need to get shoes before you try on dresses,” she explained, not that it made a lot of sense to me. I wondered if shopping for girl clothes somehow made your mind slip out of gear. As we sat down, a young male clerk approached us.

“You're getting better at sitting,” mom whispered to me, “just remember to keep your knees and legs together.” She handed me a pair of short nylon socks. “You need to wear these when you try on shoes.”

“What can I get for you, ladies?” the clerk asked.

“You probably should measure her feet,” mom explained, “and we are going to need a pair of pumps with a two inch heel, some sandals, and maybe a pair of flats.”

The clerk sat down in front of me and pulled out a device to measure my feet. I could feel him holding my foot and leg, and it seemed that he was trying to get a peek under my skirt. I was glad that mom had told me to keep my knees and legs together.

After measuring my feet, the clerk disappeared in the back of the store, only to return a minute later with multiple boxes of shoes.

Mom made me try on all of the shoes, and to walk around to try them out. I had a problem with the heels; I teetered around, nearly falling, until I figured out to step on the ball of my feet before putting the heel down.

“First pair of heels,” mom confided to the clerk, who nodded understandingly.

We finally ended up with a pair of heels in black, a pair of sandals, and a pair of flats in dark blue. With the athletic shoes my mother had bought earlier, I now had four pairs of girls’ footwear.

“Do I need all of these shoes?” I asked.

“A girl never has too many shoes,” mom explained.

Mom handed me all of the parcels, and announced, “now for dresses and skirts.”

Dresses and skirts, as in plural? I wondered.

After finding the section with my size, mom, Ashley and Kimberly went into high gear, pulling dresses and skirts off the rack and holding them up to me to see how they looked. They seemed to be having a great time doing this.

It turned out to be dresses and skirts, in plural, as in two dresses and three skirts, along with three more tops, all in various colors, which mom and the girls claimed to be “my” colors.

I had to admit, only to myself, that I rather liked trying on the dresses and skirts. They looked good on me and I looked very pretty with them on. I rather liked the feel of the hems rubbing against my hairless legs.

At long last, we all stopped at some Jean’s store. I was able to get a pair of jeans, girls’ jeans to be sure, but at least they were jeans. With my padded panty briefs and the waist nipper, I filled them out nicely. They were so obviously girls’ jeans that I knew that I could never wear while I was George, aside from the fact that they wouldn't fit without my foundation garments. I asked if I could wear them home, but my mother said no, and added that I needed all of the skirt time I could get.

Mom finally announced that we were finished shopping, much to my delight. However, we weren't going home right away. She suggested, or maybe commanded, that we were going to stop at the food court for some refreshments before heading home.

As we entered the food court, I recognized some boys from school. I really, really, didn't want them to see me and whispered this to my mom.

“Don't be foolish,” she whispered back to me, “they're likely to see you sooner or later, and by the way, you need to learn how a girl acts around boys.”

After we got our food and drinks and sat down, three boys who were in my classes headed over toward us. “Hi, Ashley,” one said, “who are your friends?”

“These are Kimberly, Sarah and Sarah's mom,” Ashley said and introduced the boys to us. I was petrified. However, having a mom with us seemed to keep things on an even keel. After a few minutes of chatting, during which I said nothing, mom announced, “It's nice to meet you, but we have to be heading home.”

On the way to the car, Ashley turned to me. “See, all your worries were for naught. The boys really thought that you were a girl.”

That was all I needed. “I don't want to be seen as a girl.”

“Well, you certainly don't want to be seen as a boy dressed like that, she snickered.

The ride home was uneventful. Ashley, Kimberly went into non-stop talking, and I, feeling girlish in my clothes, actually joined in, discussing clothes, school and boys. Mom just smiled.

Ashley and Kimberly told me how much fun it had been, and headed to their homes. When I said that I was going upstairs to change, mom told me to keep my skirt and top on. Mom, dad and I then sat down for dinner. After dinner I put on a fashion show for dad, and then I headed upstairs for bed. When I got to my room, I discovered the nightgown from the last night in the place where my pajamas would usually be. With a sigh I slipped the nightgown over my head and rubbed my hands over my body, enjoying the feel of the fabric. When I got in bed, I realized that I was really tired, and fell asleep immediately.

As Sarah.

Side Saddle

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Stuck

TG Elements: 

  • Corsets

Other Keywords: 

  • horses

Permission: 

  • Posted by author(s)

SIDE SADDLE
By Pentatonic

It was a perfect late spring day. The temperature was not too hot and not too cold. The sun was shining brightly. My uncle and I were in his pick-up, towing a horse trailer, on out way to his sister and brother-in-law’s farm. Uncle Bob didn’t like the interstates when pulling a trailer with a horse in it, so we were meandering our way on “blue highways” from Uncle Bob’s farm in south Will County, Illinois to Uncle Bill and Aunt Jane’s farm in east central Indiana.

My name is Brian, and I’m 17, about to enter my senior year in high school. I’m only 5' 8" and 130 pounds. As I had in the past, I spent my summers as a farm hand for one or both of my uncles. I wasn’t large, but working on a farm all summer meant that I was deceptively strong, as some of the school bullies found out to their dismay.

Each of my uncles and aunts farmed about a section of land, and grew corn and beans for cash crops, along with hay for the horses. Yep, horses. Depending on what month it was, Uncles Bob and Bill each had three or four horses. I would say that the steady horse population of the two combined was maybe seven and one-half horses. From time to time, one or the other would “horse-trade” one or more horses with each other. My Aunt Jane confided that shifting of horses was really an excuse for the two of them to get together. I wondered why they just didn’t live closer, but Aunt Jane had inherited her farm and was a died in the wool Hoosier. She just couldn’t abide with living in Illinois. On the other hand the soil on Uncle Bob’s farm was some of the most productive in the nation. Neither wanted to move/

I live with my parents in Joliet, but I liked being an volunteer farm hand. Both uncles and aunts have teenage daughters, and I enjoyed hanging around with them and their friends. Uncle Bob and Aunt Mary have two daughters: Alice who is a year older than I am, and would head off to college at the end of the summer. Her sister, Judy, was a year younger. Their friends were in the same age span.

The best part of the summer was the horses. I love horses.

So, after school let out for the summer, I loaded up my car and headed down to Uncle Bob and Aunt Mary’s place. After getting settled in, my cousins and I grabbed a pocketful of carrots and headed off to he horse barn, just to say hello.

Goldie, my favorite horse remembered me, or maybe just the carrots, and gave me the horse version of a greeting. My cousins and I then went into the tack room and got saddle blankets, saddles and all of the other stuff, saddled up three horses, and went for a ride.

“Dad has a long list of things he wants you to do this summer,” Alice announced with a gleeful smile, “a lot of which includes shoveling horse manure.”

I smiled in return. One part of horse riding includes taking care of the horses, and taking care of the horses includes mucking out the stable. To me, it was just part of having horses, and I really didn’t mind it. “Are you sure?” I replied, “I wouldn’t want you deny you the pleasure.”

“I get enough of it during the rest of the year. It’s your turn now.”

“I saw that you guys have some new horses. They’re pretty big. What’s the deal?” I asked.

“Some guy had them for hayrides and other stuff. They really are draft horses. Dad has them here to help the guy out. Seems he hurt himself and can’t take care of them himself.”

“Does that mean that you harness them up every once and a while?” I asked.

“Yeah. Dad got an old farm wagon, you know, all wood, with wooden wheel spokes. It’s behind the barn, Dad wants us to fix it up and paint it. We can use those horses to pull it. They came with their own harnesses and tack.”

“Yeah, and we want to see if you can get the horses to back up to let you harness them up,” Judy said with a smile.

Uncle Bob and Aunt Mary’s farm is a whole section of land, a square mile, or 640 acres. That means there are plenty of places to go with the horses. After a circumnavigation of the farm, we went behind the barn to look at the wagon. It looked like something the pioneers would have had. The iron tires were rusty. The paint had long ago flaked off, and some of the wood needed replacement.

“Let’s see if we can get an area to work in, some place near an electrical outlet for saws and drills. I’ll ask your dad if I can use the tractor to move it.,” I said.

“Why don’t you use the draft horses?” Judy asked, “after all, that’s what they’re there for. Or maybe you can’t handle it. Just admit it and Alice and I will do it for you.”

With that type of challenge, there was nothing to be done but to do it myself, After moving it to a clear area near the garage, I started by removing the wheels and greasing the axles. It was obvious that it would be a real job getting the wagon back into shape.

Over dinner, uncle Bob announced that he and I were going over to Uncle Bill and Aunt Jane’s for a few days and asked if anyone wanted to come along for the ride. I really like my Aunt Jane and uncle Bill, so I had previously volunteered. I was a little surprised that neither of my cousins wanted to go, but it appears that they had made other plans.

Uncle Bob explained that he was going to take a horse over to Uncle Bill’s place, and would bring back one of Bill’s horses. “Are you sure neither of you girls want to go?” uncle Bob said. “Your uncle Bill has picked up a side saddle and a 10 year old mare, and I though that you girls might want to learn how to ride side saddle.” This was met by a look of disgust from my cousins

So, the next morning found Uncle Bob and me in his pick-up with a horse in the trailer. It wasn’t all that far to Uncle Bill and Aunt Jane’s place, and we were there well before noon. “Tell me about this side saddle,” Uncle Bob asked Uncle Bill, “When I mentioned it to my girls they said it was degrading to women or something like that.” He turned to me and asked, “Do you think it’s degrading to women?”

“How would I know, I’m not a girl. What I do know is that arguing with my cousins on things like that is a “lose-lose” situation. My uncles nodded their heads knowingly and chuckled softly to themselves.

We walked into the tack room in the barn, and there it was, all by itself on a frame. It had no fork, horn or raised cantle like a western saddle. It was more like a half of an English saddle with a couple of things poking up on the left side which I later found out to be the top pommel, also known as a fixed head, and a lower pommel also known as a leaping head. There was only one stirrup, and it was on the left side. “I bought this horse, and the saddle came with the horse,” uncle Bill said. “It also came with some Victorian riding habits, you know, tight jacket, corset, enormous skirts, the whole nine yards. I’ve convinced Jenny to try it out, and there will be an instructor coming out tomorrow. It should be fun to watch, so why don’t you plan to stay a couple of days?”

I knew from past experience that Uncles Bill and Bob liked to have some beers when they didn’t have to drive, so staying a couple of days was common.

The next morning, a glum looking Jenny was slouched against the wall of one of the horse stalls. She was eyeing the saddle with suspicion. An hour later an older woman named Mrs. Benson arrived to begin the lessons. Jenny wasn’t into it, and neither Mrs. Benson nor Jenny seemed to be getting anywhere.

After about a half hour later, the instructor looked at me, eyeing me up like some livestock. “How tall are you?” she asked. “What’s your weight?” I answered that I was 5' 8" and 130 pounds, not that I was proud of the fact that I was one of the smallest boys in my class at school.

“Look,” she said, “I planned on being here for about an hour and to teach someone to ride side saddle. How about you?” she said, pointing a riding crop at me.

“But I’m not a girl,” I protested.

“No one said you are,” she responded. “Learning to ride side saddle won’t change that. The horse certainly doesn’t care.”

“If I do, I’m not wearing any dress,” I complained.

“You’d look darling in one,” she said under her breath. “You only wear a skirt after you learn to ride,” she added.

“I’ll learn as long as no dress is involved,” I asserted.

“But how about the corset?” snorted Judy. I just glowered at her.

“The only thing you have to wear a riding helmet,” the instructor commanded. “You can leave your pony tail out or tuck it in under the helmet,” she added. I didn’t know at the time that she was contemplating how my hair would look in a french roll.

“Come here,” she commanded. “Stand on this stool, and put your left foot into the stirrup, she said. “You can lift yourself up and sit astride, and then lift your right leg up and over the horse.” I did as she instructed.

It became obvious how the pommes are used. My left leg went under the lower one. My right leg went over the upper one, and my right calf and foot laid against the left side of the saddle in front of my left leg.

“Now rock backward and forward,” the instructor commanded. “You always need to face forward, and balance your weight. Moving backward and forward makes sure that you are sitting facing forward and not sideways. Bad posture can cause all sorts of problems.”

The instructor then handed me a light cane. “You use this as a substitute for not having a leg on the right side of the horse. She then led me around the corral. “You’ve ridden before?” she asked.

“Yeah,” I responded, “but never on a side saddle.”

The lesson ended with me practicing getting on and off the horse. “Look on the internet for instructions on riding side saddle,” the instructor said, “and I’ll see you the day after tomorrow.”

“Uhhh,” I responded and looked at my uncles. “I may have to go back with my uncle Bob before then.”

“You can stay here for some time,” Uncle Bill said, “I don’t think your aunt or cousins will mind.

“Yeah, but I only brought one change of clothes,” I said.

“We’ll figure something out,” uncle Bill said.

The rest of the day involved some fairly hard and grimy work. By supper time, I was covered with dirt and smelled just as bad. When Aunt Jane saw us approaching the house, she stopped us short of the door. “You need to go into the mud room and clean up before you come into the house,” she commanded. The mud room had a concrete floor with a big floor drain. There was a hand held shower attachment on one of the walls. Thankfully it had hot water.

The activities planned for the next day involved the pond. Years before, a small stream which ran through the property had been dammed, creating a pond. The top of the dam had an overflow which had deteriorated and eroded and needed replacement. Working with an earthen dam and water always results in mud. A lot of mud. A lot of slippery mud.

Yes, I slipped on the mud and ended up in the pond, providing mirth for all present.

I squished and dripped my way back to the house. Aunt Jane met me at the mud room door with a big towel. “Get out of those wet things, and have a warm shower.”

“How about my clothes?” I asked her.

“Oh my,” she replied. “I didn’t wash them yet.”

“You don’t have to wash them, I can do it,” I stated.

“Yes, but what do you wear in the mean time?” she asked. Both of my uncles are large men, and none of their clothes would fit me.

Our conversation caught the attention of Jenny.

“Brian and I are about the same size. He could borrow one of my jeans and a t-shirt.”

“What about underwear?” my aunt asked.

“He could borrow a pair of my panties. No one will know.” she suggested with a huge grin on her face. “I bet we could even find a pair of shoes.”

I didn’t like the way this was going. “I can just wear a towel or blanket until my clothes are done,” I suggested.

“No,” my aunt said. “Go with Jenny and find something to wear.”

With a wicked grin on her face, Jenny took my hand and pulled me upstairs to her room. The commotion had caught Anna’s attention, and she invited herself into the process of finding something for me to wear. They seemed to be enjoying it way too much. I was presented with a pair of panties. Pink. “Don’t you have anything in white?” I asked.

“Just put them on and stop whining,” Anna said. “You’re whining like a girl, so it’s appropriate that you wear pink panties.” I just grunted, and put the panties on under the towel. I was surprised how comfortable they were.

Next came a pair of jeans, and I put them on. They obviously were girl’s jeans, and the fit was a little off. Then came a top. Not a flannel work shirt, not a plain t-shirt, but a girl’s top. This was followed by a pair of white tennis shoes. Jenny and Anna stood back to admire their handiwork. “Not bad,” Anna commented. “Come over to the mirror and see for yourself.” I declined the invitation.

Jenny was studying my head, with obvious disapproval. “Your hair is a mess. Let me get my blow dryer and do something about it.”

“Thanks, but no thanks,” I responded, but to no avail. I was pushed down into a chair in front of Jenny’s vanity, facing away from the mirror, and the two of them attacked my hair with blow dryer and brushes.

They finally finished and told me to turn around. I was aghast. The image in the mirror looked like a flat chested teenage girl without makeup. “Let me get Mom,” Anna suggested.

I let it be known that I thought that was a terrible idea, but just at that moment my aunt was passing the door, and heard what was said and came in. “You look very pretty, a lot like your mother when she was a girl,” was her comment.

“But I don’t want to look pretty or like my mother, at any stage of her life,” I complained.

“I’m sorry,” she said, “but you are pretty.”

Suddenly there was a flash of light, and I saw Anna with her cell phone, taking my picture. “We ought to send this to your high school for inclusion in your yearbook.

“NO! Stop this,” I yelled.

“Quiet,” my aunt said, “or your uncle will want to know what’s going on.”

“Anyway, it’s just about time for dinner, and your clothes won’t be ready in time,” my aunt explained.

So, I hung my head and shuffled down to the dining room. My uncles found it hilarious. “If you hadn’t decided to take a swim in the pond, this wouldn’t be happening,” uncle Bill said. Anyway, you look kind of pretty.” The last thing I wanted to do was to look pretty.

It was my habit to sleep in my underwear, but Anna thought that a nightgown was a better option. Thankfully I won that argument.

A side saddle lesson was scheduled for the next morning, and Mrs. Benson arrived exactly when the appointed time came. Jenny was not slumped over like the previous lesson; no, she and Anna were both alert and smiling.

“Ok, who’s riding?” Mrs. Benson asked.

Both Jenny and Anna pointed at me. I shook my head to register my disagreement.

“We can deal with that later. What you three need to do is to learn how to saddle the horse.” she said.

“All of us know how to saddle a horse,” Jenny suggested.

“But not side saddle,” Mrs Benson said firmly. “If it’s not done properly it can harm the horse, and be dangerous to the rider.” So we all gathered around and put the saddle on and tool it off until we could do it to Mrs. Benson’s standards.

“Okay, now is the time to ride.” Mrs. Benson grabbed my by the hand and led me to the stool. It was then that she saw my tennis shoes. “Those won’t do,” she said, “don’t you have some boots.”

“I took an involuntary swim in the pond yesterday, and they’re still wet.” I explained, seeing an out.

“Let me look at what we have,” suggested Anna. “I’m sure I can find a pair that will fit.”

“There’s always the boots which came with the riding habit,” Jenny commented. “They might fit.”

“Just find a suitable pair of boots,” commanded Mrs. Benson.

Unfortunately the girls decided that the boots which came with the riding habit were the best fit.

For the rest of the lesson, I learned how to trot side saddle, and by the end of the lesson I had some new aches and pains.

It was disclosed that uncle Bill had promised the Mayor of the county seat that he would provide a girl riding side saddle for the Founder’s Day parade at the end of July. It was decided that I would stay through the next week and then maybe I could teach Jenny or Anna enough for them to sit on the horse for the parade while I led it.

There was the problem of clothes. If I were to be there for the next week and a half, I needed more clothes. Aunt Jane called aunt Mary, and she agreed to come over for the weekend, and as it turned out with her daughters. Now I had to deal with four teenage girls.

When I practiced side saddle riding, I had my own fan club of my four cousins along with various friends, male and female, who found the idea of a boy riding side saddle to be great entertainment.

As time progressed, it became clear that Jenny wasn’t going to ride side saddle. After she fell off of the horse, it was decided to abandon the attempt to get Jenny to ride. It came down that either I would ride or there would be no side saddle riding since Alice was too big to fit into the riding habit. This made uncle Bill rather unhappy, since he had promised to provide a side saddle rider for the Founder’s Day parade and didn’t want to go back on his word.

I would have liked to say “it was a dark and stormy night,” but it wasn’t. It was a gray and drizzling morning, a few days later and both of my aunts and my four cousins were sitting in the living room. In the center of the room was a dress dummy with the riding habit on it. There was a long skirt; an “apron” it was called, because it wrapped around to the right and the wrapped part was fastened with a button in the back. It was unbuttoned when the rider was on the horse to cover the rider’s legs. It was accompanied by a short fitted jacket over a self tie white blouse with a big bow in the front. There was a vest under the jacket. On a table was a little top hat with a veil, a corset, a corset cover, a chemise, a pair of white drawers, like bloomers, with ribbons and lace at the bottom and some stockings. The boots were under the table.

I was sitting in the kitchen drinking coffee with my uncles. I really think that Uncle Bill was feeling badly, having put me in this situation.

Aunt Jane came into the kitchen. “It’s time to start,” she said. Come with me upstairs.” Thankfully my cousins were not invited to this part of the proceedings. She had drawn a bath and put bath salts and other concoction in the water which bubbled and smelled awfully girly.

“You need to use this hair remover. While nobody should see, you do need to remove the hair from your body, so you can feel the part. I just stood there mutely, while she handed me a container of hair remover. “Go into the other bathroom, spread this everywhere below you head, wait fifteen minutes, and wash it off in the shower. Then come back into this bathroom and soak in the bath. I did as I was told, and when the bath water started to cool off, I got out and wrapped a towel around my waist. Aunt Jane saw this and said, “Put the towel below your arm pits and just above where your boobs would be, if you had any, and put on these panties.” She called the panties ‘control panties’ and they were a bit tight, but allowed me to conceal my private parts between my legs. She then gave me a white garment, like a slip, which she called a chemise. Next, she handed me the drawers, which I put on. This was followed by the corset. “This will feel tight, but you will get used to it after a while.” It was tight, but it drew my waist down to a more or less hourglass figure. The top of the corset pushed the skin of my chest together giving me a slight cleavage. Aunt Jane enhanced this with a bunched up stocking in each cup of the corset. She then put on the corset cover, to hide the corset. She then told me to sit, and she put on a pair of stockings, and then helped my with the boots.

She helped me down the stairs, and into the living room. I felt very self conscious in front of my aunts and cousins just wearing women’s underwear which was fashionable more than a century ago. I heard some snickering, followed by my aunt Mary telling my cousins to stop, which put an end to the mirth.

Then came the moment of truth. The skirt was removed from the dress form and put around my waist. Surprisingly, with the aid of the corset, it was able to be fastened. Then I was helped into the blouse, and a big bow tied at my neck. Then followed the vest and the jacket. My aunts fussed with each article of clothing, using tailor’s chalk to mark alterations. The hat and veil were put on my head, and aunt Mary told me to walk around the room, and into the kitchen. When my uncles saw me their mouths dropped open is surprise. “Well boys, how does she look?” aunt Mary asked. I wasn’t wild about her use of pronouns, but let it pass. “Give it a twirl,” she requested, and I did.

“Ok Brian. . .” She faltered. “We can’t call you Brian, dressed like that. How about Brianna?”

“Okay.” I squeaked.

Once in the living room, Aunt Mary told me to take off the jacket, vest, and skirt, which I did. My aunts converged around the sewing machine and began to make alterations. My cousins stood there, touching the fabric, and making little noises of wonder and appreciation. “How does it feel?” cousin Anna asked.

“Different, not good, not bad, but different.” I admitted. I did not tell them that I enjoyed it; I didn’t think they would understand. “With this corset on, I get a better understanding of Womens’ Lib.

This brought a chuckle from them. “Way to go, sister,” cousin Jenny said.

“You know, you should be wearing this and riding the horse,” I commented.

“Yeah, but you do it so much better than I could,” she replied.

When the alterations were complete, I put the skirt, vest and jacket back on to check the fit. My aunts declared that it was just about perfect.

I turned to go back upstairs and to change. “Wait,” cousin Alice said. “You need to practice feminine deportment and wearing heels. I have some things that you should wear to help that.”

Alice produced a garter belt, panties, a bra, stockings along with a skirt, blouse and shoes. “Here, put these on. It’ll make you feel more feminine.”

“But I don’t want to feel feminine,” I complained.

“Oh yeah?” she questioned. “Looking at you all dressed up, you really looked happy. I think you like it, don’t you?”

I didn’t want to admit it, but I did like it.

“Get dressed, and we’ll do something about your hair and makeup. I think you’ll like that too.

“How about a french roll?” suggested another cousin.

“She’s got the hair for it,” commented Alice. I didn’t say anything about her use of a feminine pronoun. If the truth be told, I kind of liked it.

The cousins attached my hair and makeup with a vengeance. I put on the clothes they had selected, and stood up to look into the mirror.

“Oh-oh,” said Judy. “She should have kept the control panties on.” There was a noticeable bulge in front where there should be no bulge.

“Come here,” commanded Alice as she led me to the bathroom. “Do what you boys do to get that down, put it between you legs and then put on these control panties.” I didn’t like my cousins knowing what I was doing, but I followed instructions. After I put on the control panties, there was no bulge. With that smoothed out my skirt. “In the future don’t forget the control panties,” she warned.

The next day it was decided that I should wear the riding habit to practice getting on and off the horse, and actually riding the horse wearing the habit.

When Mrs. Benson arrived for the lesson, I was fully dressed in the riding habit, except for the helmet. My hair was in a french roll. I liked the way I looked, and I wanted to impress Mrs. Benson.

She was impressed, and examined me up and down. “I was right, a french roll really looks great on her,” she said to herself.

It turned out that getting on and off the horse wasn’t a problem, with the exception a show of my knickers from time to time. “A little flash of linens really interests the boys.” added Mrs. Benson. “I bet you’ll have a lot of offers for dates after the parade. By the way, you seem more feminine and refined than you did before. How did you do that?” she asked.

“I dress as a girl every chance I get, and my cousins find great joy in my ‘girl’ lessons,” I said. I didn’t add that I actually liked it.

“Well, it seems to have worked,” responded Mrs. Benson.

Founders Day finally arrived. The parade would start at the parking lot of the community church and proceed down Main Street to the courthouse square. There was a color guard from the VFW, the high school band, some convertibles filled with local dignitaries, followed by a collection of local organizations, antique cars and tractors, a float or two, two carriages, and lonely me sitting side saddle on a horse.

We were able to get the now freshly painted old wagon and the team to the parade. Anna was going to drive the team, and she was wearing a long skirt and a blouse with big sleeves. Her hair was in a braid. My other cousins rode in the wagon along with a few teenage boys.

I wore my habit, with the top hat and veil. The Mayor was so impressed that he moved me up to the front of the parade, behind the color guard, band, and local dignitaries.

The parade moved slowly, so I was able to show off doing some fancy riding and getting the horse to go backwards from time to time. The whole parade circled the court house square, where a dias had been set up like a reviewing stand.

When the parade ended, I found myself directly in front of the courthouse and the dias. My stool, which I needed to get off the horse, was in the wagon, a way back. So I sat on my horse and smiled.

I have found that most girls love horses, and at the end of the parade, I had a crowd of them around me. It took a lot of effort to keep them from getting hurt until some of my cousins came to rescue me. Rescue me from the little girls, that is, but not from the teenage boys. It was as if my habit and the horse, along with my cousins were a boy magnet. Mrs. Benson was right, I had my choice of boys. When this all started, I said I didn’t want any attention from the boys. Well, that changed.

I scanned the crowd for my aunts and uncles, and found them right across the street from the courthouse door. But the were not alone. Right next to them were my parents. OMG! It seems that one of my aunts had invited them.

I was finally able to alight from my horse, with only the minimum flash of my kickers and I buttoned the apron of my skirt behind me. The mayor came up to me and invited me to stand on the dias. Like a refined lady, I took the mayor’s hand as he helped me up the stairs. The dias was a bit crowded, with the local dignitaries and the Founder’s Day Queen and her court dressed in formals. I wanted to stand in the back, out of sight, but the mayor had a tight grip on my hand and I ended standing right next to him.

The Mayor had a few remarks and welcomed everyone to the Founder’s Day celebration. He introduced all of the dignitaries, and finally turned to me. “I want to express my thanks to the beautiful Brianna and for her display of horsemanship, or maybe I should say ‘horsewomanship’.” This was followed by some applause and more than a few whistles. Thank goodness I had my veil on, so no one could see me blush.

The mayor then announced that there were several tents set up selling food, and a collection of booths and invited everyone to partake. At last I was able to get off the blasted dias, again with the help of the Mayor. I walked over to my horse and held her reins. All around me were people with cameras. I hadn’t thought about that. The Mayor came back to me and said that some people wanted pictures of me on the courthouse steps, and with as much grace as I could muster, I let the Mayor help me up the stairs.

There was a reporter from the local paper with a photographer. “Can you take off your veil, Honey, so we can get a picture of your pretty face?” I complied. This was followed with more pictures.

At the end of this, my parents came up to me. My mother had an enormous smile on her face. “I always knew that you are beautiful, but now I have proof. Let me get a good look at my ‘daughter’.” My father didn’t look happy.

My period riding habit drew some attention. Quite a few women cam up to me, full of questions. I explained how the riding habit came with the horse and side saddle. I told them that my underwear was period reproduction, and yes, I was wearing a corset. “I couldn’t get the clothes on without it, and it was necessary for the ‘look’. The knickers are needed because otherwise it would be my skin directly on parts of the saddle.”

“Isn’t a bit uncomfortable?” one asked.

“It’s not too bad, once you get used to it,” I responded.

“How do you go to the bathroom?” another asked.

“Just like you do. Pull down what has to be pulled down, and pick up the rest and sit,” I answered smugly.

Some of the men and boys stood off a bit, just observing, or in the case of a few, ogling.

After more questions, my cousins came up to me. “Bri, we’re going to drive the wagon back to the parking lot, and we will come back with the horse trailer.”

“That works for me,” I replied. After they came back, we loaded the horse in the trailer, and my uncles headed off to bring all the horses back to Uncle Bill’s place.

My cousins suggested that we get something to eat, which sounded like a good idea since I hadn’t eaten much for breakfast. We bought some pulled pork sandwiches and soft drinks, and found a picnic table in the shade

“There’s a father-son softball game out at the park, do you want to go?” asked Judy.

“Bri’s dad is here, so maybe she, or he, could sign up,” Alice added with a smirk.

“Running bases would be a bit difficult in that skirt,” added Judy.

I just scowled at them.

I discovered that five teenaged girls, no matter what they were wearing, will attract teenaged boys. This time was no exception. A group of them came up to the table. “Hey, Anna, who are your friends,” one asked.

“They’re not friends, they’re relatives,” she responded with a chuckle.. “These are my cousins. Brianna, Alice and Judy. They’re visiting for Founder’s Day.”

“Where are you guys from?” another asked.

“I’m from Joliet,” I responded. “Alice and Judy live in southern Will County. And who are you?”

“I’m Joe, and this is Pete. We’re the cool ones, so you can just ignore the rest of these clowns. We’re friends of Anna and Jenny, and go to the same school,” he added.

“Do you want to do something?” Pete asked.

“Like what?” Anna responded.

“I donno, just something.”

“There’s a lot of stuff set up for Founder’s Day,” one of the other boys said. “Maybe we could just look around.”

“There’s going to be a dance in the park, do you want to go?” Pete added.

“Like this?” I exclaimed.

“Why not? You look great in your costume.”

I looked at him closely. He was kind of cute, I thought. Immediately thereafter I realized that I am a boy, and shouldn’t consider other boys to be cute. Hmmm, I thought, maybe the clothes are having an effect on me.

We went to the dance. It was then I discovered that I liked dancing with Pete, and enjoyed being in his arms. Just before we were ready to leave, he bent his head down, and I felt his lips against mine. OMG, I thought - I’ve just been kissed by a boy. What should I do? The devil in me said “kiss him back,” so I did.

This was not lost on Anna. “You seemed to be having a good time dancing with Pete. Did you like kissing him?”

I decided to say nothing.

“You’re not denying it, so it must be true,” added Jenny.

I could feel myself blushing. “Look! She’s blushing,” blurted out Judy. “So it has to be true.”

The were correct. Anna said, “Girl, we have to take you shopping for some girl’s clothes. I don’t think that Brianna will be going away any time soon. So my cousins took me shopping and I now have my own feminine wardrobe. Since my aunts and uncles had a lot to do with my transformation, they convinced my parents that they should not resist my dressing and being a girl.

I really enjoy being a girl.

The Babysitter

Author: 

  • Pentatonic

Organizational: 

  • Title Page

Audience Rating: 

  • General Audience (pg)

The Babysitter


By Pentatonic

TG Themes: 

  • Voluntary

TG Elements: 

  • Partial Transformations

The Babysitter - Part 1

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Partial Transformations

Permission: 

  • Posted by author(s)

The Babysitter
By Pentatonic

“Young lady, you aren’t allowed in the pool without something on top,” commanded the life guard at our community pool. I looked around to see to whom he was talking. “You, yes you,” he added, pointing at me.

“But I’m a boy, not a girl, so I don’t have to wear a top,” I complained.

“Are you sure? Isn’t your name Emily?” he asked.

“No, she’s my sister. We sorta look alike,” I answered.

My name is Chris, and the truth of the matter is that Emily and I look a lot alike. Both of us have shoulder length honey blond hair, which our Mother makes us brush every day. She says it makes our hair “glow.” Both of us are petite and about the same size. We both have pretty faces, except I’m prettier and Emily’s breasts have started to grow. This was certainly not the first time I had been mistaken for a girl. Ever since I was little, Mother liked to emphasize that Emily and I looked like twins.

My pals, Tom and Joe, thought the exchange with the lifeguard to be hilarious, and they referred to me as “miss” and “young lady” the rest of the afternoon. When I returned home, my Mother looked at me and said, “Go take a shower and get the chlorine out of your hair. Make sure you use a conditioner and brush it out when it is dry. By the way, did you have a good time at the pool?”

“The stupid lifeguard thought I was a girl, and wanted me to wear something on top. He thought I was Emily,” I answered.

When Emily heard her name, she joined in the conversation. “I have a nice tankini top you could borrow,” she suggested with a snicker, “or maybe you’d like a string bikini?” I just scowled at her in response.

“I only say that because when you were younger, you liked to dress up in my clothes,” she replied.

“Maybe so,” I admitted, “but those days are long gone.” I had to admit, only to myself, that I had enjoyed and missed those times. However, that was then and now is now, and I had grown tired of being mistaken for a girl.

“I’ve wondered what you’d look like with a little makeup and in a dress,” my Mother mused.

“That’s a great idea,” my Emily chimed in.

“I don’t think so,” I rejoined.

“Oh, come on,” Mother asserted, “it’s only once, and only for a little while.”

Emily came over to me, and cupped my chin while she examined my face. “A little mascara, some eyebrow pencil, and lip color would do the trick.”

I myself wondered how I would look. “I guess so, but only once, and no one else can know,” I reluctantly said.

“Stay right here, don’t move a muscle. I’ll be right back with some clothes and makeup,” Emily commanded. She returned a few minutes later with an armful of her clothes and a shoebox full of makeup.

“Strip!” she commanded.

“But,” I asserted.

“No buts,” Emily rejoined with a chuckle, “it’s not like we haven’t see all of you before.”

She was correct, so I took off all of my clothes. Emily handed me a pair of pink panties, which I put on. “Put on this camisole and slip,” she said as she handed them to me. She then slid a dress over my head. Since we were the same size, if fit me perfectly.

Emily then commanded that I sit, and she commenced with the makeup. Mother just sat there, enjoying the proceedings with a smile.

“Consider yourself lucky that I’m not going to trim your eyebrows, although I should. I’m just going to defined them a bit with the eyebrow pencil,” Emily declared. This was followed by an application of mascara and lip color.

“How about some blush on her, I mean his, cheeks? Mother suggested.

“Great idea,” Emily answered, and she immediately added the blush.

“Stand up, and turn around,” Mother commanded, “so I can see it all.”

“Are you two quite finished?” I said, “because I want to get back in my clothes.”

“No, I want to enjoy this for a few minutes more,” Mother answered. “It reminds me of the times years ago, when you and Emily dressed like twins,” she reminisced.

“Can I sit down, now?” and I began to sit.

“NO! Not like that,” Mother injected. “That’s not how a refined young lady sits.” I just looked at her questioningly. “You don’t just plop into a chair, You smooth your skirt under you, and sit on the front of the chair, with your hack straight.”

“But I’m not a young lady.” I asserted.

“Looking like you do now, you are,” Mother said. I just let out a sigh and did as I was told.

“Are you happy now?” I asked. “Can I get rid of this makeup and put my own clothes back on?”

“After we get a few pictures of you with your sister,” Mother added.

“NO WAY!” I shouted. I had no idea where those pictures would end up and I certainly didn’t want to find out. My complaint went unheeded, and I, sometimes by myself and sometimes with Emily, had to pose for pictures. I could see Emily trying to figure out how to get copies of those pictures for her own evil purposes.

At last I was free to change back into myself. Before changing, I paused at a full length mirror in the hallway, and examined my transformation. I did make a good looking girl, even prettier than Emily, I commented to myself.

It was then that I decided that the shoulder length hair had to go, if I were ever to stop being mistaken for a girl.

That evening at dinner, I announced that I needed a haircut.

“Why?” Mother asked, “your hair is great looking just as it is. It’s just like Emily’s,” she added.

“That’s the point,” I responded, “I don’t want to be mistaken for Emily.” I recounted the incident at the pool to my Father. “I don’t want Emily’s admirers hitting on me.”

“Well,” Mother finally relented. “I have an appointment at the beauty shop the day after tomorrow. I’ll call then up and see if they can fit you in.”

“How about a regular men’s barber?” I interjected. I was thinking about a buzz cut.

“If you want me to pay for it, it’ll be at my salon,” Mother said. “If you want to go to a barber shop, you can pay for it yourself, and walk there, because I’m not giving you a ride to a barber shop.” She had me there. She knew that I had no money of my own, since I had asked for some cash earlier that day.

My Dad just observed this exchange with a bemused smile on his face. He well knew that Mother usually got what she wanted.

The problem with Mother’s salon was that she could exercise a lot of control over what was done to my hair. I would end up with what she wanted, not what I wanted.

On the morning of the salon appointment, I sat down for breakfast wearing my usual summer grunge clothes. This was met with stern disapproval by Mother, not only for what I was wearing, but also by the way I just plopped down into my chair. “You’re not going anywhere with me dressed like that,” she said, “and sit down gracefully.”

After breakfast Mother marched me to my room to find “suitable clothes.” Suitable clothes meant a pair of tan shorts and a light blue t-shirt. “You have to brush out your hair before we go,” she said.

“Why?” I asked, “they’re just going to cut it.”

“Just do it,” she responded in a tone of voice which invited no argument. So I sat down and gave my hair a hundred strokes. When done, I studied my reflection in the mirror. My hair looked great, for a girl. Finally I passed inspection and Mother and I got into her car.

When at the salon, Mother continued to control the entire situation. “What can we do for you today, miss?” the beautician asked. I hoped that mistaking me for a girl would end with a haircut. “She’d look great with some highlights.” the beautician suggested to my Mother.

“No,” I answered. “I want a buzz cut.”

“Not with such beautiful hair,” the beautician exclaimed. “Why would you want to do that?”

“Because I’m a boy, and I want people to stop thinking that I’m a girl,” I answered.

“A buzz cut won’t stop that,” the beautician said. “You have such a pretty face,” she added. “If you get a buzz cut you won’t look like a boy, you’ll look like a girl with a buzz cut.”

“There are a lot of girls with buzz cuts,” my Mother injected, “so a buzz cut won’t solve your problem.”

The beautician said that she could give me a “boyish” cut, which turned out to be a lot like a pixie cut. I wasn’t happy with the final result, but there wasn’t much I could do about it.

Emily was at the door when Mother and I returned home. “Let me see,” she said. “Tinkerbell!” she exclaimed with great glee. “You still look like a girl!”

I retreated to the bathroom \to see what I could do with the disaster on my head. After fiddling around I was able to get rid of the Tinkerbell look, but I was only partially successful in getting to look like a boy.

In addition to Emily, I have a three year old sister named Ann. After lunch, Mother suggested that I take Ann in the stroller to the park, “for some fresh air.” Ann loved the park. As usual, after installing Ann in the stroller, I also packed some of her favorite books, and some goodies to eat. The park is only a few blocks from the house, and when we arrived there I found a shady place to spend some time. I let Ann climb up on the park bench next to me, and I pulled out her favorite books. “Which one do you want to start with?” I asked her. After she made her pick, we sat side by side, and I read and showed her the pictures.

After about an hour a woman came down the path with two girls who appeared to be about four or five. When I looked up, she smiled at me and said, “You two make such a pretty picture, Do you mind if we join you?” Her girls climbed up on the park bench, and one of them asked, “Can we listen to you read?”

“Sure,” I said, and I continued to read, but now I had to pass the book around so all of the girls could see the pictures.

After some time amusing all three girls, the woman turned to me and said, “I’m Mrs. Benson and these are my daughters, Amy and Susan.”

“I’m Christopher Parker, and this is my sister Ann,” I said in the way of an introduction.

“Christopher?” she said questioningly, thankfully not saying that she thought that I was a girl. So much for the haircut.

“Yes,” I responded. “Ann loves it when I read to her. My older sister Emily never reads to her.”

“The two of you make such a pretty picture, I just had to stop and say so,” Mrs. Benson added. “Do you babysit for your sister?” she asked.

“Yes, I have since Ann was born. Like I said my older sister always seems to have other things to do. I don’t mind it, and it brings Ann and me closer.”

“Do you babysit for any other children?” she asked.

“Not really, I just turned fourteen,” I explained.

“Are you interested in babysitting?” she asked.

“I never really thought about it, but I guess I could. However there doesn’t seem to be much a market for boy babysitters,” I said.

“Boy?” she questioned. “My girls seem quite taken to you,” she added, “I don’t think that your being a boy would be a problem. Would you mind if I called you?” I gave he my phone number and we parted, and I went back home.

I recounted the events at the park to my Mother. “Is it all right if I took a babysitting job with Mrs. Benson?” I asked her.

“If she doesn’t mind you being a boy, I don’t see any problem,” Mother answered.

So began my career as a babysitter. I really liked the Benson children, and Mrs. Benson told me that the children liked me because I paid attention to them and read and played games with them. A big plus was that I got paid and now had my own money, which frosted my sister.

It was several months later that a problem arose. I was scheduled to babysit for the Bensons. On the Monday before, Mrs. Benson called Mother, and Mother told me about the situation. It appears that the Bensons had a dinner arranged with their friends, the Carlsons. The Carlsons had one child, and their babysitter had cancelled. The Carlsons had suggested that maybe they could bring their six year old daughter to the Benson’s house, and I could sit all three. This was hardly a problem. The problem was that the Carlsons did not like boy babysitters.

“Mrs. Benson wondered if you would mind dressing up as a girl for the babysitting job,” Mother related. “I don’t have a problem with it, but it’s up to you.”

Inwardly I was excited. I hadn’t lost my desire to dress as a girl; I just wanted it to be on my own terms, and not to be mistaken to be a girl unless I intended it to be so.

“I don’t know if I could pull it off.” I said.

“I think you could,” she said. “Why don’t we ask Emily.”

“I’d rather not,” I answered.

“I think you have to, because you will be borrowing her clothes,” she said. So Emily was invited, much to her glee, to join in this endeavor.

“Chris will have to part with some of his, or her, cash and buy her own makeup,” my sister declared, “It isn’t a good idea to share makeup.”

“How about clothes?” Mother asked.

“I don’t want to share underwear,” Emily answered.

“Okay,” Mother said, “we’ll make a trip to the mall tomorrow after supper.”

So the next day, after supper, Mother, Emily and I went to the mall. The first stop was at the lingerie section at the department store, where I purchased two pairs of pink lace trimmed panties and nude pantyhose. The two pairs of panties were to help me “tuck.” I drew the line at buying a training bra, however, much to Emily’s disappointment.

“If she isn’t going to get a bra, she needs a camisole,” Emily insisted, so I bought a camisole.

Next we stopped to buy some cosmetics. “I’d like some starter makeup for my daughter,” Mother told the clerk, “she’s only 14, so it should be minimal. Maybe eyebrows, mascara, blush and lipstick,” Mother added. The clerk applied the suggested makeup. When completed to Mother’s approval, she told the clerk, “We’ll take whatever you used, and maybe some perfume.”

“Maybe a pair of shoes?” Emily then suggested. So we went to the discount shoe store and purchased a pair of flats.

On our way out, we passed an earing kiosk. “Let’s have her ears pierced,” Emily suggested. While I did not like the idea, Mother did, and I ended up with two gold studs in my earlobes. I successfully resisted purchasing more earrings, mainly because I was paying for everything that was purchased.

When we arrived back home, Mother told me to go to my room and put on the panties, pantyhose and camisole, while she and Emily looked for clothes. “Do you want a dress or a skirt?” Emily asked with a chuckle. Emily was enjoying this far too much, I thought. “Neither!” I replied. “How about just a pair of slacks?”

Mother and Emily selected several slacks, and I ended up with a pair of dark brown ones with a zipper up the left side. They selected a tan sleeveless blouse with ruffles up the front, to hide, as Emily put it, “your lack of boobage.”

“You need to practice putting on your makeup,” Mother declared, so I sat at Emily’s vanity, and I learned how to apply makeup. “Remember, you will have to refresh your lipstick during the evening,” Mother advised.

When my makeup met Mother’s approval, I finally got a chance to look at the finished result. I was impressed. I really looked like a teenaged girl. “We’ll do something with your hair on Saturday,” Mother declared.

Mr. Benson picked me up for the babysitting job. “Wow,” he said when he first saw me, all dressed, with makeup and my pixie hairstyle. “When I heard what my wife suggested, I never thought it would be this good.”

When the Benson’s daughters saw me, all they did was to say how beautiful I was. There was nothing about the fact that I had not dressed as a girl before this time. Likewise, when the Carlsons arrived, their daughter just took me at face value, and didn’t question my gender.

Just before they left, Mrs. Benson pulled me aside for some last minute instructions. “You really look fabulous tonight,” she said. “I’m really impressed. Are you sure you’re not really a girl?” she said with a laugh.

The evening went smoothly. We played some simple board games, watched some television, had snacks, and I read to them. It was readily apparent that the Carlsons never read to their daughter. When the Bensons and the Carlsons returned, I was doubly delighted, not only did the Bensons pay me, which was all I expected, but the Carlsons also insisted on paying me. I also got a nice tip from both. The second delight was when the Carlson’s daughter asked if I could be her babysitter in the future. I agreed, even if it would require buying more girl clothes.

Based upon recommendations from the Bensons and the Carlsons, I began sitting every weekend when I was not sitting for my little sister. Of course for my sitting jobs, I dressed as a girl, which I was really beginning to like doing.

Along the way I acquired a lot of girls’ slacks and blouses and yes, I did buy some training bras with Emily’s gleeful help. Then came the time when the Carlsons were going to dinner and a show with their daughter, and they invited me to come along, since their daughter behaved better when I was there. This invitation meant that I would have to wear a dress. Again, Emily offered her help, with glee.

Mother, Emily and I went to the mall to find a dress. I was wearing panties, panty hose, flats, a camisole and a nice blouse and slacks. We found a light blue dress with cap sleeves, a tight bodice and a pleated full skirt, to hid any bulge. We stopped at a store that sold costume jewelry, and I bought a fake pearl necklace and bracelet.

I was pleased that the Carlsons liked the way I was dressed. Their daughter held close to me the entire evening, and I made it a point to talk to her without being condescending which pleased her and her parents. “Our daughter looks to you like an older sister,” Mrs. Carlson said during a washroom break. “You are going to make a really good mother,” she added. I smiled back at her and thanked her.

With my babysitting jobs, I was a girl every weekend night. I really liked this, and later, even though I was not at a babysitting job, I began to dress as a girl after school on week nights.

“Are you sure that you’re not a girl?” my Mother asked me one Wednesday evening when I was fully dressed.

“I’m not sure,” I replied. “I do like being a girl.”

Several months thereafter, Mother asked me the same question. “I’d really like to be a girl,” was my answer this time, and with my parents’ help, I started on the long process to meet that goal.

The Babysitter - Part 2

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 7,500 < Novelette < 17,500 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

Permission: 

  • Posted by author(s)

The Babysitter - Part 2
By Pentatonic

Author’s Note: This is a continuation of The Babysitter. All of the people who commented wanted me to continue the story. This part starts where The Babysitter ended, so you might want to read that first.

During the summer it came to my attention that the shorts being worn by basketball players seemed a lot longer than they had previously been. In fact they came down to just above the knee, sort of the same length as the kind of skirts I liked. Not only that, they were made of a shiny fabric. I just had to have a pair. With my babysitting money in my pocket, I hopped on my bicycle, and headed to the local discount store. To my delight, they weren’t all that expensive and I bought a pair in black polyester. To my further delight, I found that the mens’ version had two pockets.

The weather the next day was one of those delightful mid August days. I put on my new shorts and a light blue t-shirt and rode my bicycle to Tom’s house. Tom’s mother met me at the door. “Come on in, Chris, they’re in the den,” she said, as she followed me into that room. Tom and Joe were sprawled on the furniture, watching something on the television. A grunt from Tom was my sole greeting. I looked for somewhere to sit, and saw a straight backed chair. I walked over to the chair, and instinctively smoothed out the shorts as if they were a skirt before sitting on the front edge of the chair, my back straight, my knees together, and my legs crossed at the ankles, exactly as my Mother had instructed me to do. This was not lost on Tom’s mother, who was closely watching me. I saw her stare, and gave her a small smile. She smiled in return, but it looked like there was a question in the smile, like why did I sit like that?

No one said anything for a minute, then I said, “I was thinking of taking a bike ride to the Purple Horse and getting some ice cream.” Neither Tom nor Joe even looked at me, but this time it was Joe who grunted. The Purple Horse is an ice cream parlor on the other side of town, known for its ice cream.

“I donno,” rejoined Joe. “Whose paying? I can’t, I don’t have any money.”

“I’ll treat,” I answered, “I babysat last night, so I have cash.”

“That sounds like a great idea,” Tom’s mother said, “but you don’t have to treat, I’ll give Tom some money.” She turned to Tom and Joe, and said, “Get off your lazy butts and go out for some fresh air with Chris.” Tom and Joe stood up and slouched to the door. I followed with my back straight up, taking measured steps like I would as if I was wearing a skirt.

Before we got to the front door, Tom’s mother pulled me aside. “You look somehow different,” she said in a low voice. “Not bad, just different.” If she was looking for an explanation from me, she wasn’t getting one. I just smiled at her, and followed Tom and Joe out to our bicycles.

There were some boys at the Purple Horse when we arrived. They gave Tom and Joe cursory glances. However, they obviously were checking me out. Joe came close to me and whispered, “They think you’re a girl and they want to hit on you.” I just frowned at him in return.

This didn’t deter Joe. “Heck, if I didn’t know, I’d want to hit on you. You really look foxy right now.” I just jabbed my elbow into his side to show my displeasure, even thought I was inwardly pleased that the boys thought I was a girl and that Joe thought I was “foxy.” Thankfully the boys got their ice cream and left with no further incidents.

When I got back home, Mother asked me about the ride to the Purple Horse. I related that some boys were checking me out and that Joe thought that I was foxy. At this point Emily joined into the conversation. “Foxy?” she questioned. “Now if you had some mascara and lip gloss on, then you would look foxy.”

“Who asked you?” I rejoined. “This is none of your business.” Emily just laughed. But she is right, I thought to myself.

***

Even though my hair was short, Mother still insisted that I brush it a hundred times each evening. One evening when I was doing this, Mother commented that my pixie cut was getting a bit shaggy. “I’ll make an appointment for you for the next time I go.”

When I got up on the morning of the appointment, Mother said, “Wear some of the clothes you wear when babysitting.” This meant dressing like a girl. “Maybe a little mascara and lip gloss would also be in order.” I smiled at her, inwardly happy to be a girl for the morning.

When we arrived at the salon, the beautician asked me what I wanted. “A trim. It’s getting a little long,” I answered.

“How about some highlights?” she asked.

“Not today,” I answered. I would have loved to have highlights, but I didn’t think it would go over well when school started in the fall.

***

On the afternoon after my salon appointment, I was hanging out with Tom and Joe. Although I had removed all traces of makeup, my hair style seemed to pique their attention, and they were curious. “Isn’t babysitting a chick job?” Tom asked.

“Maybe most babysitters are girls, but there is no rule,” I replied. “The people I sit for don’t seem to mind that I’m a boy,” I added, intentionally failing to mention that the Carlsons thought that I was a girl.

“So what do you do when you babysit?” Joe asked.

“Pretty much what your babysitters did when you had a babysitter,” I said, but then I added, “I also read to the children, play games, and otherwise entertain them.”

“Does that mean you play dolls with them?” Joe said with a smirk.

“On occasion I have to do things that five to seven year old girls like to do,” I answered.

“Sounds kinda girly to me,” Joe rejoined.

“Maybe it is, but at the end of the evening I have cash in my pocket. That’s more than you can say after playing computer games all evening,” I added. Actually, I liked the girly part, because I had recently wondered whether I wanted to be a girl. Doing girly things gave me something that I had missed when I was being brought up as a boy.

***

My babysitting for the Bensons and the Carlsons continued, and from their recommendations, I gained some additional clients, one of whom was Mrs. Sloan. Mrs. Sloan was a single mother with a six year old daughter, Ellen. I had recently discovered that the “Wizard of Oz” was part of a series of Oz books, and I was able to take one of the other books out from the library. Therefore, I took the Oz book with me to read to Ellen.

Because it was the first time I sat for Ellen, I paid special attention to how I was dressed. I had a relatively new pair of black capri pants and a white blouse with cap sleeves. I did not tuck the blouse in the pants, because it helped hide the fact that my hips were somewhat small. I brushed out my hair. My chest was totally flat, which was not a real problem since a lot of girls my age had nothing on top. I did decide to help things along and I wore a training bra. Mother agreed with me that makeup was not necessary.

Mrs. Sloan had, as she described it, a hot date, and needed time to prepare, so my Dad drove me to the Sloan house. As soon as I arrived, it was clear that Ellen didn’t like being left with a babysitter. “She’s always like this when I go out on a date,” Mrs. Sloan said, as if this explained everything, which it didn’t. It wasn’t until I started reading to her that Ellen calmed down.

“No one ever read to me before,” she said as she snuggled up to me.

“Do you like this story?” I asked. She nodded her head in affirmation.

About an hour and a half later the front door flew open with a bang, and there stood Mrs. Sloan with a very angry look on her face. “The bastard!” she exclaimed, “He’s married! No more dates with him,” she fumed. Perhaps because her daughter and I were present, she gave no further details. “Just keep on doing what you’re doing and ignore me,” she said as she plopped down into a chair.

Ellen and I just looked at each other. “I don’t like it when Mommy’s mad,” she said softly.

“Do you want me to keep reading, or should I go home?” I asked Ellen.

“Please keep reading,” she replied, and so I did. All this time Mrs. Sloan looked at the two of us, and slowly her face relaxed as she began to take in the story. I was almost afraid to stop, not knowing what would happen if I did. However, after another hour, my voice was tired and we were at the end of a chapter.

“I think it’s time for bed,” I told Ellen, and she nodded her head. “Do you want me to put her to bed?” I asked Mrs. Sloan.

“If you wouldn’t mind,” Mrs. Sloan answered, “I’m still angry about that bastard.”

“Will you read to me some more?” Ellen asked.

“If your mother wants me to sit for you again,” I said, “sure.”

After getting Ellen in bed, I sang a short lullaby to her. It seemed to please her. When I came back downstairs, Mrs. Sloan was still sitting in the same chair, but now she had a glass with amber liquid in her hand. I assumed, correctly, that it was a stiff drink.

“I’m sorry that I blew up and made a scene,” she said.

“That’s okay, I think I understand,” I replied.

“I’m not sure you do, since you are only fourteen,” she said, “you aren’t dating boys yet, are you?”

“No,” I said.

“I want to say that you handled yourself very well. I can tell that Ellen is quite taken with you. Reading to her was brilliant. No other sitters ever did that.”

“I read to my baby sister, and to all of the kids when I babysit,” I explained. “I, and they, enjoy it. It seems to calm them.”

“You are a very interesting girl,” she said, “sit down next to me and tell me about yourself,”

I sat down as gracefully as I could, and started to talk. “There isn’t much to tell. I’m fourteen, and have a younger sister, Ann, and an older sister, Emily. I’m starting high school shortly, and I enjoy reading. I sit for Ann, and recently I’ve started sitting for other people. That’s about it,” I said.

“Do you like babysitting?” she asked.

“I do. I like children, and I like the money I earn. Emily doesn’t like to sit, and it frosts her that I am earning money and she isn’t.

“Well, you’ve had a full day, and I imagine that you want to return home,” she said, and reached into her purse and handed me some money. A lot of money, more than I expected.

“This is a lot more than I charge,” I said.

“Maybe, but you’re worth every penny.”

I called my Dad to pick me up, and we both stood up. Unexpectedly, she reached over to me and gave me a hug. I hugged her back, and she put a finger to my face, and looked into my eyes. She moved her face close to mine and gave me a kiss on my lips.

“Oh, if only you were older,” she said. I couldn’t quite understand what that meant, but let it go without comment.

***

A week before Labor Day Mrs. Benson called me. That she called was hardly unusual, since this is the first step in a babysitting job. However, what she proposed was different. Her church holds a Labor Day picnic every year, and she had related that when I sit I often read to the children. Some of the Elders thought that having a “Story Lady” at the picnic might be entertaining for some of the children, and Mrs. Benson wanted to know if I was interested in volunteering to be the Story Lady. Volunteering, as opposed to being paid.

The Bensons had been very kind to me over the summer, and volunteering would be a way to show how much I appreciated their kindness. Okay, I didn’t mind the no pay part, but there was a much larger problem. I was starting high school, and I was registered as Christopher, a boy. A boy with a pixie haircut. I could deal with that by manipulations to my hair style, as long as there could be no other connection with me as a female. If I showed up at the picnic as the Story Lady, even the most dense of the neanderthals at the school could connect Chris, the boy with the funny haircut with Chris, the girl in a full skirt with a pixie haircut who was the Story Lady at the picnic. Since Mrs. Benson knew that I was a boy who dressed as a girl for my babysitting jobs, I felt that I could tell her that I was concerned that someone might connect Christopher the high school student with Christine the story lady. “I see what the problem is and I understand your concerns. Maybe it is best to drop the whole idea.” I felt badly about this, but neither Mrs. Benson nor I could see a solution.

Then it came to me. “I could be the ‘Story Teller’ and dress androgynously, pretty much as I would when I went to school.” The Elders approved of the change and everything was set.

My exposure came not from any of the students at my highschool, but from an unexpected place, namely Tom’s mother. Tom and his parents attended the same church as the Bensons, and as it turned out, the Carlsons. Tom’s mother was standing next to the Carlsons, watching me read, and Mrs. Carlson turned to Tom’s mother and said, “She’s babysat for us, and she does a wonderful job reading and entertaining the children.” Tom’s mother caught the use of the feminine pronoun. This brought to her mind the time at Tom’s house when she caught me sitting down in a refined feminine manner. Thankfully she said nothing to Mrs. Carlson.

Later that day, after my time as the story teller was finished, she came up to me and asked if I had a few minutes.

“Sure,” I said, “what’s up?”

“Should I call you Christopher, or maybe Christine?”

I was thunderstruck and made no response. “I was talking with Mrs. Carlson, and she thinks you are a girl,” she said, “I’ve known you for years, and I know that you are a boy, so why does Mrs. Carlson think you are a girl?”

I explained as best as I could that the Carlson only wanted a female babysitter, so I pretended to be a girl.

“That’s not all there is to it, is there?” she questioned. Without waiting for an answer, she said, “I’ve noted that you are acting a lot like a girl recently. You move, you sit, you stand and you walk like a girl. Why?”

I didn’t answer her.

***

In September Mother recalled something I had said the past summer. She had asked me, “Are you sure that you’re not a girl?”

At that time I answered, “I’m not sure, I do like being a girl.”

Recently Mother asked me the same question. “I’d really like to be a girl,” was my answer this time. After consulting with our family doctor, we were referred to a specialist child and adolescent Gender Identity Clinic because I was only 14.

Mother made an appointment, and on the day of the appointment we left my little sister in the care of my older sister, who recited a litany of complaints for being forced to babysit.

No healthcare can start without paperwork, and this was no exception. After filling out what seemed to be reams of forms and a written gender identity test, we finally met with a psychologist who told us that I needed to have a full physical exam with complete blood work, and to come back in when this was done.

Our second session was more productive. I was surprised when the psychologist told us that the majority of children with suspected gender dysphoria don't have the condition once they reach puberty. Notwithstanding this, she recommended that treatment should be arranged with a multi-disciplinary team. This is a group of different healthcare professionals working together, which may include specialists such as mental health professionals and pediatric endocrinologists.

“Why do you feel that you are a girl in a boy’s body?” she asked. I told her of my experiences and feelings, after which she asked, “Who have you told this to?”

“Well, Mom, of course, and she told Dad. I’ve been babysitting this past summer, and Mr. and Mrs. Benson know. I babysit for their daughters. I think that a friend’s mother is suspicious.

“Have you told any of the other parents of children for whom you sit? When you sit for these children do you dress in girl’s clothes?”

“I haven’t told anyone else, and yes, I dress like a girl when I babysit,” I answered.

“Have you told any of your friends?”

“No, but my friend Joe thinks that I act awfully girly,” I answered.

“You might want to talk to the families for whom you sit and tell them that you are a boy,” she suggested, “if you think that they can keep it confidential. There is the danger that some of the parents or your friends will react badly, so you have to move with caution. I assume that you don’t want the school to know.”

***

I decided that I would talk with the Carlsons and Mrs. Sloan, and maybe Tom’s Mother.

I called Mrs. Carlson and said that there was a problem which I had to discuss with her, and I arranged to meet her later in the week.

My heart was pounding when I rang the Carlson’s doorbell. Mrs. Carlson answered the door with a smile. “Whatever the problem is, we can solve it,” she said, “come on in and we’ll talk.”

After exchanging pleasantries, I got down to the problem. “Mrs. Carlson, I haven’t been truthful with you,” I started to say.

“In what way, honey?” Mrs. Carlson asked.

“Well, when I first sat for you, the Bensons said you only wanted a girl babysitter, so I pretended to be a girl. I didn’t expect to keep sitting for your daughter, so I didn’t see the harm in it, especially since the Bensons knew,” I explained.

“Oh, is that all it is?” she said with a big smile. “I’ve known that you are a boy for quite a while.”

“You did?”

“Yes, the Bensons told me, and I have no problem with your gender,” she answered. “Remember when I told you that you are going to make a really good mother? Well I still believe that. Even if you can’t have your own children, you can adopt.”

The end result would be that we would not tell her daughter, and that I would continue to sit for her.

***

Next on my list of confessions was Mrs. Sloan. For my meeting with her, I decided to wear a dress and some makeup. When she opened the door, she said, “Well look at you! You look fabulous. Come on in and tell me about this problem. It doesn’t mean that you won’t be able to sit any more? I certainly hope not. Have a seat and make yourself comfortable”

“After I tell you, you may not want me to sit for your daughter.” I said.

“Tell me what?”

“I’m not a girl. I’m really a boy wearing a dress,” I blurted out.

After a pause, she said. “. . . And wearing it well. You look delightful and very feminine,”

“You’re not angry with me?” I questioned.

“Hardly. How could anyone be angry with such a delightful creature as you are. Like I said, I only wish you were older.”

“Why?” I asked.

“In the parlance of the street, you are a ‘chick with a dick,’ and I find that attractive. If you were eighteen, I’d have my way with you right now.”

“Why eighteen?”

“Laws. Sex with a minor is a crime.”

“Oh,” I said.

With that she stood up and then sat next to me. I could feel our bodies touching. She moved her finger to my face and I turned my head toward hers. She moved her face to mine and kissed me on my lips. I could feel her tongue touching my lips and I opened them to admit her tongue into my mouth. It was like nothing I had ever experience before. At last she broke off the kiss, but continued to stare into my eyes. “We better stop this before it goes to far,” she finally said. “I hope you enjoyed it as much as I did,” she added.

“I did,” I said softly.

“Good,” she said, “because I want you to continue to sit for my daughter.”

***

Talking with Tom’s Mother was a bit of a problem. I satisfied her curiosity, but it appeared that Tom’s Dad was a complete homophobe, and hated anything other than ‘straight’ sex. Tom’s Mother told me that my secret was secure with her, but then she said, “I don’t ever want you to be alone with my son.”

***

I related my experiences with my counselor, and she thought that things went better than expected. “What happened with Tom’s mother is not unusual. I think that from now on you should keep your distance from Tom.”

She made some notes and then said, “I’d like to talk with you about school and your other friends. I think that you should suppress any indication of your gender identity at school, because of the potential adverse consequences.” I had to agree with her.

While I saw less of Tom outside of school, the same was not true with Joe. Unlike Tom, Joe and I shared a lot of advanced classes, and I was helping him with his homework and preparing for exams. Since I had to explain the material to Joe, my understanding increased to the point that my grades improved greatly.

***

One dreary September afternoon, Joe asked, “Hey dude, can you help me with the algebra assignment?”

“Sure,” I replied. “Where?”

“How about your house?”

“Is that because you want to ogle at my sister?” I asked.

“Well, maybe a bit. But if I can’t ogle at her, I can always ogle at you,” he said with a smirk.

“Knock it off, or I won’t help you with math,” I responded with a scowl.

When we arrived at my house my sister Emily was lounging in a most unladylike manner in front of the television. She looked up as we came into the room. “Hello Joe,” she said, and then she added, “Hello Tinkerbell.”

“Why did she call you Tinkerbell?” Joe asked as we headed for my room.

“She thinks she’s being clever, when in fact she’s only disgusting,” I responded.

“Does she mean Tinkerbell as in Peter Pan?”

“Yeah, when I got my hair cut, she thinks it looks like a pixie cut, and therefore she calls me Tinkerbell.”

Joe looked at me closely. “You know, she’s right, you do look like Tinkerbell.”

“Thanks for nothing,” I responded sarcastically.

While going through the math exercises, I caught Joe staring at me. “What?” I demanded.

“You would make a really good looking girl if you combed your hair in a real pixie, put on a dress, and wore makeup,” he commented in return.

“Will you stop that?” I demanded. “Stop hitting on me. I’m not a girl, I’m a boy. Boys don’t hit on other boys unless . .” I left the sentence unfinished.

This didn’t phase Joe. “If I hit on you hard enough, would you give me a kiss?” he asked.

This threw me for a loop. “If you don’t stop hitting on me, I’m going to hit you with this math book.” I said and held the book up in a threatening manner.

“Okay, Okay,” he said, “I give up.”

“Good, and keep it that way,” I said. I lowered the book and continued to glare at him. Deep inside of me I wanted to kiss him, but I would never admit it to Joe or anyone.

When we were finished studying, I walked Joe to the door. “See you tomorrow,” I said.

“See you tomorrow, Tinkerbell,” he responded.

My sister heard that and began to giggle. “See what you started,” I complained.

The next day at school I sat next to Joe in English class. “Hi, Tink,” he whispered.

“Will you stop that?” I whispered back.

“Only if you kiss me,” was his whispered reply.

“Disgusting!” I said as the bell rang and the class started.

A day later, Joe and I were walking home after school, and we passed a fast food joint. “You got enough money to buy each of us a shake, Tinkerbell?”

“Not if you don’t stop calling me that,” I responded.

“You know how to make me stop.” he replied with a smirk.

“If I buy you a shake, will you stop it for at least a week?

“Okay, buy me a shake, and no Tinkerbell for a week,” he promised, and we went inside and ordered the shakes.

Exactly a week later, Joe and I again were walking home from school. “The week’s up, Tinkerbell,” he announced.

I stopped, and looked at him. “You really mean that you want to kiss me? That’s so . . .” I said, not completing the sentence.

“Not only do I want to kiss you, but I want you to kiss me back. A long lingering kiss with lots of tongue,” he said.

“That’s disgusting,” I said, even though deep inside of me I wanted to do exactly that.

When we arrived at my house, I asked Joe if he wanted a hot chocolate before we started studying. “That sounds great, Tinkerbell,” he replied. My sister caught his answer and started laughing. “See what you started,” I said to him with clenched teeth.

“I didn’t start it, your sister did,” he responded.

“Well, I want both of you to stop it,” I said.

“You know how to make me stop it,” he said.

“Disgusting,” I said. While we were drinking our hot chocolate, I felt his leg rubbing mine under the table. “Stop that,” I hissed.

“Stop what?” he said with a false look of innocense on his face.

“You know,” I hissed.

“Oh that,” he said and he moved his leg away from mine.

When we had finished our hot chocolate, we repaired up to my room to start studying. I turned to look him in the eyes. “If we kiss, do you promise to never call me Tinkerbell again?”

“Never? That’s a long time. How about a year?”

Wait, I thought, what am I getting into? I didn’t like the way the negotiations were going. It was almost like I was agreeing to a kiss, which in fact I was.

“Two years,” I countered.

“Let’s compromise on a year and a half,” he said.

When I nodded my consent, he put his arms around me and I put mine around his neck. Our faces grew nearer to each other and our lips touched. I opened my lips to let his tongue inside, and later I pushed my tongue into his mouth. I was really enjoying this. When we broke off the kiss, the only thing I could say was, “Wow!”

“You kiss like a girl,” Joe said. “How about another one, just for fun?”

“Okay,” I said, and we kissed again. While kissing Joe, I compared his kiss with the kiss Mrs. Sloan had given me. I couldn’t decide which was better; they both were wonderful.

***

It was a Wednesday evening when Mrs. Sloan called to ask me to babysit on Saturday. What was different was that it would be a late night, and Mrs. Sloan suggested that I spend the night at her house. “I’ll have to ask my Mom,” I said, “hold on.”

I relayed her suggestion to my Mom. “It sounds okay to me,” she said.

I picked the phone back up and said, “Mom says it’s okay.”

On Saturday afternoon, I packed an overnight bag with my pajamas, robe, slippers and a change of clothes, along with my makeup and a hairbrush. I included the Oz book and some homework from school.

I knew that Mrs. Sloan liked it when I wore a skirt or dress, so I decided on a dark blue dress with a flared skirt. I wore a training bra to give me something on top. Naturally, I wore a nice pair of panties and a full slip under the dress. The dress was a good choice, because when she saw me, Mrs. Sloan said, “You look gorgeous, as pretty as a picture, but then, you always look delectable.”

Mrs. Sloan picked me up at my house at 5:30, because, as she said, she needed time to get ready for her night out.. “You don’t have to eat first, I’ll have something for you and Ellen for dinner.” Her idea of something to eat was take out Chinese.

“I’ve set you up in the guest bedroom for tonight,” she said, and then added, “By the way, I left a present for you to wear on the bed. I hope you’ll like it.”

The present she had laid out on the bed consisted of a white satin nightgown that came down to my knees and a negligee that was mainly chiffon. Next to them were a pair of mules with a one inch heel, and marabou on the toes. They were so beautiful, I could hardly wait to wear them.

After Mrs. Sloan left, Ellen turned to me and asked, “Are you going to put on the nighty that Mommy bought for you?”

“Sure,” I replied. “If you want, we can both put on our nighties and I can read to you. Would you like that?”

“Oh yes,” she said, and shortly thereafter I was wearing the nightgown, negligee and mules and sitting on the couch with Ellen who was dressed in a nightgown and robe sitting next to me.

After I put Ellen in bed, I sat at the kitchen table and worked on my homework assignments for the coming week.

When Mrs Sloan came home a little after midnight, I was seated on the couch watching the television amid a sea of satin and chiffon with my feet up on a footstool. “I see you’re wearing your presents. How do you like them?” she asked.

“They’re wonderful. I love them, but you didn’t have to buy them for me,” I answered.

“But you look so delicious in them,” she said, and with that she sat next to me on the couch. “Everything okay this evening?” she asked.

“No problems whatsoever. Ellen wanted to see me wearing these, so we both got dressed for bed, and I read to her,” I answered. “So how was your evening?” I asked, changing the topic.

“It was nice, but no romance. There were some good looking guys there, but we didn’t connect. However, there was a woman there who seemed interested in me.”

She stood up. “Let’s go into my room so I can take off this dress,” she said, and she grabbed my hand and pulled me up from the couch. Once in her room, she turned her back to me and said, “Unzip me, sweetheart,” which I did.

Much to my surprise, she took off all of her clothes in front of me. I couldn’t help not staring at her naked body. “It doesn’t bother you, does it, seeing me naked?”

“Umm,” I answered, not knowing what else to say. She sat next to me on the bed, and cupped one of her magnificent breasts in her left hand.

“You like?” she asked. I nodded my affirmative.

She stood up, and said, “Let me put on a nightgown,” which she did.

She sat back down and turned to me. “Do you have a girlfriend?” she asked. I shook my head. “How about a boyfriend?”

“Not really,” I answered, “but there is this boy, Joe, who I’ve known for years, who seems interested in me.”

“Howso?” she asked.

“Well, my sister started calling me Tinkerbell when I got my pixie haircut. Joe heard this and kept calling me Tinkerbell. The only way he would stop was if I kissed him.”

“And did you?”

“Yes.”

“Did you like it?” she asked.

“I did,”

“Do you want to kiss me?”

“Yes,” I said in a lowered voice. With that she put her arms around me and pulled my face close to her’s, and we kissed. And kissed again.

“Did you like kissing me?” she asked.

“Yes,” I responded.

When re released our mutual embraces, she looked at me and said, “I was going to ask you if you wanted to keep me company in this bed for the night, but on second thought that might not be a good idea. We might start something we can’t stop.” I nodded my agreement, and with that, we each went to our own beds.

***

The next week Joe and I were walking home from school together, and I was thinking about the kisses with Joe and with Mrs. Sloan. “You never told me why you wanted to kiss me, only that you did,” I said. “So, tell me. Why?”

“I donno,” he answered, “I just did. In fact I still want to kiss you, like right now.”

“Don’t be ridiculous,” I responded.

“Okay. How about later?”

“Not until I know why.” I said, not realizing that by that statement I was agreeing to kiss Joe when he told me why.

“So, if I tell you why, you’ll kiss me again,” he said.

“I didn’t mean that,” I said.

“Well, you’re the one who brought it up,” he said defensively

“Okay, maybe I did, but I don’t have your answer,” I said, “but tell me, are you attracted to me, sexually?”

“You mean, do I want to have sex with you?”

“That’s putting it a little bluntly, but that’s exactly what I mean,” I said.

“Then the answer is yes,” he replied.

“You never told me,” I said.

“You never asked,” he responded.

“Why would I?” I said.

We walked in silence for a few minutes, each lost in our own thoughts.

“So tell me,” I asked, “do you want to have sex with any other boys?”

“No.”

“Girls?”

“The only boy or girl I want to have sex with is you,” he finally said.

“But I’m not a girl,” I interjected.

“You probably could fool nine-tenths of the people on the planet. Not only do you look a lot like a girl, but you look like a very sexy girl, even if you don’t have any tits.”

The thought of tits brought the image of Mrs. Sloan’s naked breast to my mind. Joe and I walked in silence for another minute,

“Look,” I said, breaking the silence, “if you want to remain my friend, this talk of sex has to end right now, and never come up again. That includes kissing and touching.”

“But I thought you liked kissing me,” he said defensively. I didn’t respond. “Okay, I’ll agree with you if you let me see you all dressed up as a girl. Panties and makeup included,” he said.

“I’m not negotiating with you. Every time I do, you twist my words around and I’m agreeing to something I don’t want to do. No conditions.”

Did I mention that Joe wants to be a lawyer?

After another minute of silence, Joe said, “No conditions, but will you let me see you dressed up as a girl anyway?”

“I thought I made this clear, the answer is NO!” I stated.

***

Shortly before Halloween Emily and I were sitting at the kitchen table. Mother walked into the room and announced, “We have to find a costume for Ann, and one of you has to take her around for trick or treating. Who will it be?”

“Chris is so good at it, let him do it,” Emily announced.

“Look, I do all the babysitting,” I said, “it’s Emily’s turn.”

“Okay, if you two can’t agree, I’ll have to ask Ann,” she said. I knew full well that Ann would chose me, so I agreed to take Ann out. “But Emily has to be in charge of getting her a costume,” I added.

A few minutes later Mrs. Benson called. It seems that Mr. Benson had to be out of town on Halloween, and Mrs. Benson didn’t want to leave the house that night. She asked me if I would take her girls out trick or treating. I readily agreed, since I was already taking Ann out, and now I would be paid for my time. It wasn’t long before Mrs. Carlson and Mrs. Sloan made the same request of me, and I would be taking Ann, the two Benson girls, the Carlson’s girl and Mrs. Sloan’s daughter out for trick or treating, and getting handsomely paid for my efforts.

“Are you going to wear a costume?” Mrs. Benson asked.

“I don’t have one, so no,” I answered.

“I have a witch’s costume that I put together a few years ago for a party,” she said. “I found a long black dress with a high collar and long sleeves at a thrift store, along with a black cape, and I bought a witch’s hat and a cheap wig. If you want, you can borrow them.”

“Okay, it sounds like a plan,” I said.

My school allows students to wear costumes to school on Halloween. When Joe asked me if I was going to wear a costume to school, I said that I might.

“What is your costume?” he asked.

“Just wait for Halloween and see,” I replied. An evil thought went through my mind. He wanted to see me in a dress, with makeup, and that’s exactly what I would be wearing, just maybe not as he envisioned it.

I thought that the costume needed a heavy application of green eyeshadow and blood red lips, so I made a trip to the drug store to buy the same.

On Halloween morning I got up an hour earlier than usual. I put on a pair of panties and pantyhose, just because I would be wearing a dress. I put on my training bra, and stuffed a little filling in the cups. Over this I put on a knee length black slip which I borrowed from Mother, and then slipped the dress over my head. I borrowed a pair of black boots from Emily.

“Zip me up,” I asked Mom. The dress was a little loose, but that didn’t matter. Once I had the dress on, I found that there was a slit up the left side, which exposed the lace on the hem of my slip. I also found out that the dress had a pocket, into which I could put my student ID, my phone, and the lipstick.

I sat down at Mom’s vanity, and let her put on a heavy layer of the green eyeshadow. “I think that you need some mascara,” Mom declared, as she applied it to my eyelashes. She then let me put on the blood red lipstick. I was ready, and I headed out the door.

I met up with Joe in the hallway at school, and let out a suitable witch’s cackle at him. He just stared at me for a minute.

“Chris, is that you?” he asked.

“It sure is,” I replied. “You said you wanted to see me in a dress with makeup, so here I am. By the way, you promised that if I let you see me like this, that all talk of sex has to end and never come up again, including kissing and touching.”

“Wait a minute,” he said, “part of the deal had to do with you wearing panties.”

This time I had him. By bringing up a detail, panties, he tacitly agreed with my basic premise of no more talk of sex or touching or kissing. Naturally, I could concede the point of panties, since I was wearing them under the dress, and he would have to agree with the rest. “Okay, I’ll concede that I have to wear panties. That’s hardly a problem, because I am wearing panties under this dress.”

There was nothing he could do, but he didn’t immediately concede defeat. “That’s what you say, but I need proof!”

“Right here, right now, in the hall? That might cause a disturbance,” I retorted.

“No, later, in private, but I have to see it with my own two eyes,” he said, and we walked into class.

It was teasing time. For our first class together I moved my seat close to his right, and when I sat down the parts of my skirt below the slit fell to the right and left, exposing my pantyhose and the lacy hem of my slip. I pretended that I was not aware of this. Joe, on the other hand, couldn’t take his eyes from my shameless display.

This did not escape the teacher’s notice. “If Mr. Joseph Glynn can give me his attention, maybe we can get started.” Lucky for me, the teacher could not see my display, and I did not look at my skirt at all during the class. I also fixed an interested look on my face. Joe, on the other hand, was getting more hot and bothered for the duration of the class.

When the class ended I stood up and executed a quick twirl, which caused my skirt to flare out. I then strutted out the classroom door. I did note that Joe stayed seated, as he squirmed to adjust a bulge in his pants which had grown during the class.

Once in the hall, a girl I knew came up to me. She had been able to see all that had happened. “Great costume, you shameless hussy,” she said with a huge smile and chuckle. “You really had Joe going, not that he didn’t deserve it. Way to go, girl.”

“Thanks, he had it coming,” I replied, and for the rest of the school day, I took every opportunity to tease Joe.

One of the activities of the day was a costume contest. When I arrived at school that morning, one of the teachers handed me a card. “If you’re part of the costume contest, write you name and class grade on this card and pin it to your costume. During the day the student council will be grading the costumes and there will be an assembly after the last class, when the scores for the best costumes will be announced.”

At the assembly, all of the students who wanted to be part of the contest were separated by grade, and went up on the stage. We were asked to walk across the stage, turn at the microphone, say our name and grade, turn again and walk to the other wing of the stage. When it was my turn, I fixed a big smile on my face, strutted to the microphone, did a skirt flaring twist, and said, “Christopher Parker, grade 9.” I then did another skirt flaring twist and strutted to the other side of the stage, accompanied by cat-calls and whistles. When the 9th graders were finished, I found an empty seat next to Joe.

“You’re a hopeless flirt and tease,” he said.

“But you liked it,” I replied.

“Well, yes,” he conceded.

I won second place for my grade, and honorable mention for the entire school, and I proudly pinned the ribbons to my dress.

As Joe and I were walking home, he said, “There still is the matter of the panties.”

“When we get to my house,” I said.

When we got to my house. Joe and I went to my room, and there I proved that I was wearing panties.

There was no time for me to rest on my laurels because now I had to take Ann and my babysitting charges out to trick or treat. All of the girls loved my costume.

“Be back before it gets dark,” Mother said, and we headed out to get treats. Trick or treating went without incident, although I did get a lot of compliments on my costume.

The next day at school I also received a lot of compliments on my costume, all of them from girls. I only got strange looks from the boys. I stayed close to Joe during the day for what protection he could offer. I mentioned the strange looks to Joe, and asked him if I had a problem.

“I don’t think so. Before Halloween, most everyone thought you were kind of weird. Now they’re sure that you are,” he replied. Weird I could live with. Be that as it may, I made sure that I dressed as masculine as possible thereafter, not only at school but also after school, except for my babysitting jobs.

The Babysitter - Part 3

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

Permission: 

  • Posted by author(s)

The Babysitter - Part 3
By Petatonic

Thanksgiving can be a hectic time for most families, and mine was no exception. We had Thanksgiving dinner with Mom’s family on the actual day, and celebrated with Dad’s family on the Saturday thereafter.

On Thanksgiving day, we hosted the dinner for Mom’s parents and her brother’s family. I only have one cousin on my Mother’s side, and he is in his twenties. The ‘men’ watched football and the ‘women’ prepared the food. I wore androgynous slacks and a white shirt, and the day was pretty much uneventful. There were some comments about my haircut, but nothing came of it.

Saturday was different. We all met at my grandparents’ house, which was about a two hour drive away. Dad came from a large family, and all of them were there, with spouses and children.

On the way, Emily called me Tinkerbell. Immediately I objected. “Mom, make her stop calling me Tinkerbell,” I complained.

“Emily, don’t call your brother Tinkerbell,” Mother instructed.

“Okay,” Emily answered, “but only for today,”

When we arrived, Dad and my uncles watched some football and drank beer. Mom and my aunts fussed around in the kitchen, getting in each other’s way. I hung around with those of my male cousins who were more or less around my age and watched the games. Emily sat with her female cousins, talking. During a commercial break, I got up from watching football and went to get some snacks and something to drink, and happened to pass my sister and girl cousins.

“While you’re up, Tinkerbell, get me some more popcorn,” Emily said. I shot her a dirty look.

“Tinkerbell?” one of my female cousins asked.

“Oops,” my sister said with a total lack of sincerity, “I’m not supposed to call him that.”

“But why did you?” another cousin asked.

“Look at his hair. He has a pixie cut. Doesn’t he look like Tinkerbell?” Emily said.

While Emily was supposed to not call me Tinkerbell, Mother’s commandment to her had no effect on my cousins. “Now that you mention it, he does,” commented my cousin Ruth.

“With a little makeup, the resemblance would be improved,” another cousin said. I noted that several hands went into purses, and mascara and lipsticks magically appeared. It was clear that a hasty retreat was called for, and I hurried back to the football game.

I tried to remain invisible the rest of the day, but to no avail. After dinner, one of my girl cousins motioned me to come over to her. “Your sister said I should ask you about your Halloween costume. By the way, aren’t you a little old for Halloween costumes and trick and treating?” she said.

“I took my baby sister and some of the kids I babysat for around for trick or treating. I hadn’t planned to wear a costume, but one of the Mothers had a costume and she loaned it to me.” I said.

At this point, Emily piped up, and said, “Tell them about the costume, and don’t forget to mention that you wore it to school on Halloween.”

I decided to refuse to answer that request, and started to walk away. “Not so fast,” one of my cousins said, and grabbed my arm. “We want to know about the costume!”

“If he won’t tell you, I guess I’ll have to,” Emily said. “He dressed as a witch.”

“You mean like a dress and all that stuff?” another cousin asked.

“Naturally,” Emily said. “He sits for the Benson girls, and Mrs. Benson had the long black dress and a witch’s hat. Not only that, but the dress had a big slit up the side. Guess what he wore under the dress.”

“What?”

“Panties, pantyhose and a black slip with lots of lace at the hem,” Emily said with a smug look on her face. “Wait, I might have a photo on my phone.”

Unknown to me she did, and it was passed from cousin to cousin. “You really look like a girl in that dress,” one said, “I like the makeup.”

“Do you like dressing up as a girl, Tinkerbell?” another asked. I walked away before I had to answer that question.

Later on, Emily said to me, “The girls want more pictures of you in a dress, and they asked me to loan one to you. You should be thankful that I didn’t tell them that you have your own dresses.” With that, she started giggling.

That Thanksgiving I only had one thing to be thankful for: none of my cousins went to my school.

***

Joe was over at my house a week later. It was Sunday, and we were in my room preparing for a test on Monday. I had been babysitting the night before, and while I had hung up my blue dress in my closet, I had not closed the door all the way. I guess the color caught Joe’s attention, because he walked over to the closet and opened the door. He pointed at the dress and looked at me. “What’s this?” he asked.

“None of you business,” I replied.

“Is it yours?” he asked.

“Like I said, none of your business,” I answered.

“You don’t deny it, so it must be yours,” he crowed. “You have to let me see you wearing it.”

“I thought we settled all this when I showed you my Halloween costume,” I said.

“But this is different,” he said.

“Look, if you keep this up our study sessions are over. No more help,” I said. Joe knew that this was a real threat, because my help had made a difference in his grades.

“Okay, Okay, I’ll drop it,” he conceded, but I had the feeling it wasn’t quite over.

***

I had made an appointment to sit for Mrs. Sloan’s daughter on Friday night. Since Mrs. Sloan expected it to be a late night, she suggested that I stay the night. She also said that she and Ellen would pick me up at 5:30 and have supper for us.

That Friday, Joe and I walked home from school together, and sat around my house. At 4:45 I realized that I had to get ready, but Joe hadn’t left yet. “Hey, I’ve got to get ready for a sitting job,” I said, hinting that it was time for Joe to go home. He didn’t get the hint.

“I want you to go home, now!” I finally said, forcefully. Well, maybe a little too forcefully, because Emily heard it and stuck her head in the door.

“What’s wrong?” she said.

“I have to get ready for a babysitting job and Joe won’t leave me alone,” I answered.

“I don’t understand,” said Joe. “I’m not bothering him, I’m just keeping him company.”

“He’s not bothering you,” Emily said with a wicked smile on her face, “so what’s the problem?”

“You know what,” I said to Emily.

“Oh, that,” she said.

“Yes, that,” I responded.

“But Joe might like it and find it interesting,” she said, “let me help you to get ready.” With that she went into my closet, pulled out my overnight case, and put it on the bed. It was obvious that we had Joe’s attention. I didn’t think that a four alarm fire would get him to leave.

I had packed the overnight case with my babysitting clothes, including two sets of panties, pantyhose, and training bra. Emily picked out one set and handed it to me. “Go take your shower, Tinkerbell, and I’ll take care of the rest,” she said with a smirk on her face. I grabbed the clothes and headed for the bathroom, but not before I heard her say to Joe, “Tinkerbell likes to dress up as a girl for her babysitting jobs.”

After a quick shower, I came back wearing panties and bra. I sat down and started putting on my pantyhose. I really had Joe’s attention as I ran my hands up my legs to smooth out my pantyhose. “I could help you with that,” he volunteered.

“No thanks, I can do it myself,” I said. It was then that I noticed a bulge in Joe’s pants. “Maybe you should go in the bathroom and take care of that,” I said, pointing at his crotch.

“Maybe you could help me,” he said.

“No way, you pervert.” I replied.

“Look at who’s calling me a pervert. A boy wearing panties,” he said, with a smile on his face.

I tried to ignore him as well as I could, and put on a slip. I then retrieved my blue dress from the closet, the same blue dress that had started everything, put it over my head, and smoothed it over my body.

I turned my back to Joe and said, “You might as well make yourself useful and zip me up,” which he did. I then went to my closet and picked up a pair of one inch heels, which I then put on. I reached into the overnight case and retrieved my makeup bag, fake pearl necklace and bracelet, and began putting on some mascara and lipstick.

“Your lips look so kissable with the lipstick,” Joe said. I scowled at him, “no pajamas?” he said.

“I have some at Mrs. Sloan’s house,” I said, omitting to say that what I had as her house was a satin nightgown and chiffon negligee.

I finished packing by putting some homework and books to read to Ellen in the case. I then started arranging my hair in an unmistakable pixie style.

I turned to Joe. “Okay?”

“More than okay, you’re gorgeous,” he said.

Mother called upstairs to tell me that Mrs. Sloan and her daughter Ellen were out front.

“I guess it’s about time for me to go home,” Joe said.

“About time?” I queried, “It’s more like forty-five minutes late. Not a word to anyone about what just happened,” I added. “If you do, I’ll spread the rumor that you’re hot for me,” I threatened.

“But it wouldn’t be a rumor,” he said, “because it’s true.”

“You’re hopeless,” I said, as I picked up my overnight case, went downstairs, put on a coat and headed to Mrs. Sloan’s car.

When we arrived at her house, Ellen got out of the car and gave me a hug. “There’s Chinese on the table for both of you,” Mrs. Sloan said, “I’m going clubbing, to see who I can pick up, since a certain someone is too young.”

As before, Ellen and I put on our night clothes and I read to her. After that I worked on my homework. About 11:30 Mrs. Sloan opened the door and came in. “Absolutely beautiful,” she said, referring to my satin nightgown and chiffon negligee. “I have a new friend, Sylvia, who should be here any minute. If you don’t want to meet her, you might want to go to your room, but you don’t have to.”

“I have to put my homework away, before I go to bed,” I said. I was half-way through with this when Sylvia arrived.

After Mrs. Sloan introduced us, Sylvia said, “My, oh my, what do we have here? She’s pretty as a picture. I could just eat her up.”

“The paint’s not dry on that picture, she’s only fourteen,” Mrs. Sloan told Sylvia as a warning.

The two women wanted a night-cap and invited me to keep them company. I sat as demurely as I could as they discussed the nightclub and who was there, and very candidly discussed what each of them wanted to do to some of the patrons. It was slightly embarrassing and I began to blush.

“Oh, look,” Sylvia said, “she’s blushing. Isn’t it precious?” I just blushed the more.

While we were sitting, I noticed that Sylvia’s hand was below the table, and Mrs. Sloan was squirming, as if someone was rubbing her leg, which in fact was exactly the case.

“Why don’t we go upstairs,” Mrs. Sloan said.

“Great idea,” Sylvia replied, and she grabbed my hand and all three of us went into Mrs. Sloan’s bedroom. I really wanted to go to my own room and bed, but Sylvia would not let go of my hand.

“Unzip me, please, honey,” Sylvia said as she released my hand.

“Same here, darling,” Mrs. Sloan requested. Both women took off their dresses, and followed it with the rest of their clothes. Mrs. Sloan put on a nightgown, and handed another to Sylvia.

“Now we all match,” declared Sylvia, as she rubbed my behind.

It appeared that things were getting dangerous. “I think that I’ll hit the hay,” I said, and headed for my room and bed.

Sylvia had left by the time Ellen and I rose. I found Mrs. Sloan sitting at the kitchen table, drinking coffee. “I made a pot,” she said, “help yourself.”

When I poured a cup and sat down, Mrs. Sloan said, “Sylvia’s a bit brazen, isn’t she, but that’s exactly what I needed. She’s a really great lover, but you wouldn’t know about that, would you?”

“Hardly,” I replied.

“Well, if you ever wanted to learn, she could give you post-graduate courses,” she said with a snicker.

Before we left for my house, Mrs. Sloan pulled me close to her and gave me a long passionate kiss, which I gladly returned.

***

There was a threat of snow in the air and the Christmas lights were shining through the twilight. Today was the last day of school until the new year. Naturally, on a weekend night in the Christmas season, I had a babysitting job. This time for as family named Werner. I had not sat for them before. They were friends of the Bensons, and the Bensons were hosting a Christmas party and the Werners, along with my parents and the Carlson were invited but the Werners didn’t have a babysitter. The Bensons recommended me to them.

That was great, but the best part of the evening was that Emily had to stay at home and sit for our sister Ann. I was getting paid and she was not. How wonderful.

“I think that Tinkerbell should give me half of what she gets,” she complained.

“I’ll think about it,” I said, “if you stop calling me Tinkerbell. Otherwise all you get is pixie dust.”

The Werners had two sons, Steve, aged 10 and Robert, aged 11. Babysitting for boys was a new experience for me, and I decided that I would I would not dress as a girl. I didn’t think that they wanted me to read to them, so I didn’t bring a book. Almost as an afterthought I grabbed a deck of cards and put it in my pocket.

Robert made it clear that he didn’t think that he needed a babysitter. It didn’t look like it was going to be an easy evening. I then remembered that I had a deck or cards, and I put it on the kitchen table.

“Do you guys know how to play cards?” I asked.

“Yeah,” answered Robert.

“Any particular games?”

“Nah,” responded Steve.

“How about blackjack?”

“No.”

So I taught them how to play blackjack. We used uncooked macaroni as pretend money. After that I taught them some of the various poker games.

It was going to be an early evening, and the Werners returned home before the boys’ bedtime. “Did you boys behave yourselves?” she asked them.

“Yeah, Chris taught us some card games,” said Robert.

“Can Chris sit for us again?” asked Steve.

“Well, that’s something new,” said Mr. Werner, “where did you learn to sit for boys?”

“I just remembered what I liked to do when I was their age, and went from there. I listen to what they say, and don’t talk down to them. When I was their age, I liked to hang around with the older boys,” I explained.

“Well, the Bensons were right when they said you are a good babysitter,” Mrs. Werner said, and she paid me along with a good tip.

“If you’re ready, I’ll give you a lift home,” Mr. Werner said. While in the car, he told me that he was a psychologist, and concentrated in gender issues. “I wouldn’t expect that you have any ideas what that’s about, do you?”

“A little,” I answered.

“Do you know what gender dysphoria is?” he asked.

“Yeah, that’s when a boy thinks he should be a girl, and the opposite for girls,” I said.

“Wow, either you are well read, or I may be touching into a sensitive area,” he commented, almost to himself. Nothing more was said until I arrived home.

I had the opportunity to again sit for the Werners a short time later. Before they left for the evening, Mr. Werner said he wanted to talk to me and we went into his study. “You’ve sat for the Carlsons, haven’t you?”

“Yes,” I replied.

“Now you don’t have to answer the next question, in fact you can tell me to mind my own business,” he said. “Do you remember Mrs. Carlson saying that you will be a good mother?” I thought about what he said, and took a few moments before I answered.

“Yes, I remember, and she did say that,” I answered softly.

“Wow,” he said to himself. He then turned and looked directly at me. “Thank you for being candid with me. As I told you, I’m a psychologist, and everything you told me is confidential. I’m not allowed to tell anyone, not even my wife, and certainly not my children.”

When the evening was over, I told my parents how different it was sitting for boys, as opposed to girls.

“But did you have fun?” Mother asked.

“Yeah, I taught them to play blackjack and poker. They loved it, and the evening seemed to fly by,” I answered.

“What did you think of the Werners?” she asked.

“I like them,” I said, especially Mr. Werner. Did you know he is a psychologist?”

“I think I heard that somewhere.” she said.

***

On the first Monday of the Christmas break, I was contemplating going shopping for Christmas presents. Before I left, Joe called, and I invited him to come along with me. “Maybe we could catch a movie,” he said, and then added, “if you pay for it.”

I had made a list. I would get barrettes or hair bands for the girls for which I sat, and a deck of cards for each of the Werner boys. For Ann, I bought a Barbie Doll, for Mother a CD of oldies, for Dad, a book about golf. That left Emily. I wanted to get something appropriate for her, and that required more thought. That first day, Joe and I just window shopped. I ended up treating Joe to lunch at the food court, and we just wandered aimlessly until it was time for the movie to start. It was an action movie, with lots of car crashes and explosions, but not a lot of plot or quality acting. As usual, I paid for the admission, popcorn and drinks.

Once the movie started, I felt Joe’s hand on my knee. “Stop that,” I whispered, “remember, you promised no touching.”

“But you’re so touchable. When I think about you in a dress I just want to touch you,” he replied in a whisper.

“But you promised,” I responded.

“Sheesh,” he complained. “Okay,” he finally conceded and moved his hand.

But not for long. It might have been fifteen minutes later, and his hand was back, this time rubbing the inside of my thigh. I was tempted to pour what was left of my drink on his head but restrained my impulse. I remembered how Emily used to complain about boys rubbing her leg at the movies.

“Knock it off,” I whispered into his ear.

“But it feels good, doesn’t it?” he said in the nature of a response. I didn’t answer that. Rather, I said, “If you don’t stop now, I’m walking out of the theatre.

“Okay, Okay,” he said.

A half an hour he was at it again. This time he got a physical reaction from me. I couldn’t very well walk out of the theatre with a big bulge in my pants. I was tired of fighting him, so I stood up and moved to a different seat. He did not follow me.

When the movie was over, and we were far enough that no one could hear me, I lit into him. “Joe, you promised. I’m really pissed at you. Come on, both of us are boys. Don’t ever do that again to me.”

“I’m sorry, I thought you’d like it,” he said sheepishly.

“Well I didn’t!” I said emphatically, “I thought I made that perfectly clear the first time you did it.”

Regardless of what I was saying, deep down in me I did like it, not that I’d ever admit it to Joe.

We wandered around the mall, until Joe saw an ice cream store. “Just to show that you’re not mad at me, I’ll let you buy me a shake,” he said.

“What? Where’s the logic in that?” I spouted off.

“I donno,” he said, “I just want a shake.”

“Okay, if you promise to behave yourself,” I said.

“Does ‘behaving’ include behaving badly?” he asked with a silly grin on his face. I didn’t grace that with a comment.

***

By the end of the week I had all of my Christmas shopping done, which was good, because I had no money left. For me, that was not a problem, because I had three babysitting jobs lined up for Friday, Saturday and Sunday, which would put a good amount of money in the coffers. I finally decided to get Joe a gift card for the ice cream shop, good for ten shakes. For Emily, I bought her a nice maroon skirt.

Buying the skirt was an interesting adventure. Joe was with me and I was dressed androgynously in jeans and a sweater. I had seen the maroon skirt on a mannequin in the window and I looked through the racks of skirts until I found it in the proper size, and took it to the register. The clerk looked me up and down, and with a smirk finally said, “Aren’t you going to try it on, Honey?”

“It’s a gift for my sister,” I explained.

“I’m sure it is,” the clerk responded with a voice dripping with disbelief. “But why don’t you try it on, anyway?” she said.

Joe was no help. “Why don’t you try it on. I’d like to see how you look in it.”

“Listen to your boyfriend.” the clerk said.

I finally gave in and went to the changing room with the skirt. “When you have it on, come out and let me see how it fits you,” the clerk said.

“Yeah, I’d like to see it too,” added Joe.

I put the skirt on and stepped out of the changing room. The devil in me decided to give it a twirl, much to the pleasure of Joe and the clerk. “It fits you well,” the clerk said, “but if you are going to twirl like that you should have a matching pair of panties.”

“She’s right,” said Joe. I just gave him a dirty look, but in the end I bought the panties.

***

All of the children for whom I bought the gifts seemed to like them, especially Ellen. When I stopped at the Sloan house, Mrs. Sloan invited me inside to give Ellen her present. While there, I saw Sylvia sitting on the couch. I was wearing girls’ jeans and a frilly top under my coat. “Take off your coat and sit next to me,” she said, as she patted the cushion.

“I’ve got to take Ellen to see her doctor, Mrs. Sloan said, “Why don’t you stay here and keep Sylvia company while we’re gone. It shouldn’t be more that an hour.”

“I’ll take good care of her while you’re gone,” Sylvia said. Yeah, like a shark takes care of a food fish, I thought.

Not twenty seconds after the door closed behind Mrs. Sloan and Ellen, Sylvia had her left arm around my shoulder, and her right hand on my knee. Oh boy, I thought, just like Joe in the theatre. I loved what she was doing, but I knew it could quickly get out of control. I finally steeled myself and said, “Remember, I’m only fourteen.”

“That’s right,” Sylvia said, “I kind of forget that when I see you. You may not know it, but you drive me wild.”

“Would a kiss help?” I asked.

“Definitely,” she answered, and we held each other highly and enjoyed a long lingering kiss.

I realized that Sylvia had only seen me as a girl. “Did Mrs. Sloan tell you that I’m a boy?” I asked.

“No, she must have forgotten that. You don’t look like a boy. Are you really a boy?”

“Yes, last time I checked this morning in the shower I was,” I said.

“But you are so delicious as a girl. Having boy parts just makes it ssoooooo much better,” she said with a big grin on her face.

Sylvia and I petted and kissed until Mrs. Sloan and Ellen returned.

“I can hardly wait until you’re eighteen,” Sylvia said.

“Get in line,” responded Mrs. Sloan, with a smile.

***

After Christmas, Joe and I decided to cruise the mall to see what bargains there were. I was flush with cash from all of my babysitting, and Joe, naturally, had none. I think my purpose of being there was to pay for everything.

“How about a movie?” he suggested.

“Are you paying?” I asked, even though I knew the answer.

“Well, no,” he replied. “I’m kinda broke.”

“I don’t know,” I said. You certainly didn’t behave yourself last time we saw a movie.”

“It’s not my fault,” he said, “when I’m with you I kinda lose control. It’s your fault for being so foxy.”

“Good grief,” I responded.

As we aimlessly walked around the mall, I noticed that Joe was pausing and intently studying some of the dresses in the store windows. “See anything you like?” I asked him.

“I’d like to see you wearing them,” he replied.

“No, not for me, for you. Any you’d like to wear?” As I said it, I noticed that Joe was blushing.

“You’re blushing!” I crowed triumphfully. “You really want to wear a dress!”

“Umm. Err, no,” he stammered.

“Think silky panties caressing your body,” I whispered to him with an evil smile on my face. Joe’s face just got redder. “I could buy you a pair, and you could wear them under your jeans. No one would know except you and I.”

“But you aren’t wearing panties under your jeans,” he protested.

“You never know, and in this case you never will,” I observed saucily.

At this point we were passing a lingerie shop. I grabbed his arm. “Look,” I said with a smirk on my face, “You can go in and buy a pair. I’ll give you the money, and wait out here for you. I’m sure the sales clerks will be MOOOST helpful, but you’ve got to tell them that you’re buying them for yourself.” I had to chuckle at Joe’s obvious discomfort.

“Err, no!” he said.

“Maybe some other time,” I said, continuing to tease him.

“No.”

Despite his protestations, I think I had him. A thought crossed my mind. Valentines day was coming up. Maybe a Valentine’s day present for Joe? Pink, lace trimmed, with little red hearts? I smiled at my own cleverness.

I looked at my watch. I had a babysitting job tonight with the Bensons. They had invited the Carlsons over for dinner, and I was babysitting the Benson’s girls and the Carlson’s daughter. I had bought a delightful pair of burgundy slacks with a side zipper and some burgundy shoes, both of which I wanted to wear tonight. Unfortunately, the slacks had no pockets. I needed a burgundy purse.

“I need to buy a purse,” I told Joe, “and then I have to get home to get ready for a babysitting job.” I looked around, and saw a store that was likely to have what I wanted. I went over to a display of purses while Joe meandered around.

“Can I help you?” a clerk asked.

“Yes, I need a burgundy purse, not too expensive.” I was wearing masculine clothes and the clerk gave me an odd look. “Oh, not for me,” I lied, “for him. He’s too embarrassed to buy it himself.”

I called to Joe. “Come over here. How is this one?” I asked.

“Alright, I guess,” Joe mumbled. The clerk transferred her odd look from me to Joe.

As we were leaving the store, Joe asked, “Why was the clerk giving me funny looks?”

“I told her that the purse was for you, but you were too embarrassed to buy it yourself.”

“Gee, thanks,” he said sarcastically.

“Get used to the looks. You’ll see a lot of them when you buy lingerie for yourself.”

“Fat chance,” he rejoined.

***

New Year’s Eve was only a few days away, and babysitters were in high demand. The Bensons had booked me a month ago, and the plan was that I would sit the Benson girls as well as the Carlson’s daughter at the Benson’s house. Because it would be a late night, It was decided that the girls and I would spend the night at the Bensons. This would mean that I needed some sleep wear. I didn’t think that the nightgown and negligee that Mrs. Sloan gave me would be quite appropriate, and, in any event, I kept them at Mrs. Sloan’s house.

It just so happened that Joe was at my house that day. “Mom,” I called out, “I need to go to the mall. Can you take me there?”

“Sure, honey, what do you need?” she asked.

“Some sleep wear for New Year’s Eve,” I responded.

“Can I go along and help you pick something out?” Joe interjected.

“If I let you pick something out, it would most certainly be a ‘naughty nighty,” I said. “I’ll probably end up with some uninteresting pajamas, a terry cloth robe and some plain slippers.”

“Now, I have to get ready, so scoot,” I said.

“I thought I’m going with you to the mall,” he said, “and I can help you get ready.”

“I don’t need your help,” I said.

“Yeah, but it’s more fun when I help,” he said

“Fun for you, not me,” I asserted.

Since Joe made no sign of leaving, I decided to get ready in front of him. Maybe he’ll get embarrassed, and leave, I thought. Not a chance, was my next thought.

So I undressed, until I was totally naked. I noticed Joe staring at my crotch as I started to put on a pair of panties. “Pervert,” I said.

“Me a pervert?” he replied, “Just like the last time you called me that, I’m not the boy wearing panties.” I just gave him a disgusted look as I put on a bra and nylon knee highs.

“No pantyhose, no dress?” he said as he saw the knee highs.

“What is it about you and dresses?” I said, and then I paused, “Oh yeah, now I remember, you want to wear a dress.”

I put on the burgundy slacks that I recently bought, and an ivory blouse with ruffles, to disguise my lack of boobs. I put on my burgundy shoes, and grabbed my burgundy purse. “A little lipgloss and mascara, and I’m ready,” I told no one in particular.

Mother decided to accompany Joe and me on my shopping expedition. True to form, Joe wanted me to get a baby doll that was more chiffon than substance. I, on the other hand, liked a pajama set in ivory satin.

“Those look like boys’ pajamas,” Joe complained.

“No they don’t, the buttons are on the other side, and there’s no fly,” I explained.

“But they’re not very sexy,” he said.

“If you want sexy, go buy yourself a baby doll and wear it,” was my final comment.

***

New Year’s Eve was hardly exciting for me. Hardly exciting, but profitable. Of course, I enjoyed entertaining the girls as much as they enjoyed me entertaining them. I had brought some sparkling grape juice and some plastic champagne flutes. By 10:45 the girls were drooping, and they would never make it to midnight, so I declared that we were sophisticated New York ladies, and therefore on New York time. That way we could welcome the new year at 11:00 local time, an idea the girls loved.

After the girls were in bed I put on my new pajamas, robe and slippers, put some music on, cleaned up the house and started reading. The Bensons and Carlsons finally rolled in about 1:00 a.m. “You’re still up,” Mrs. Benson said, more of a question that a statement of fact.

“I wanted to make sure that you party animals got home safely,” I responded.

“Yes Mother,” Mrs. Benson said with a laugh. Mrs. Carlson smiled with a knowing look on her face.

I related how the girls and I had spent the evening, and said that they were all safely tucked into bed. “Oh my,” Mrs. Benson said, “you even cleaned up after your little party.”

“Just like a good Mother would,” said Mrs. Carlson, approvingly.

“Those are pretty pajamas and robe,” Mrs. Benson said.

“Thank you,” I said, “I bought them specially for this evening. I wanted to look good for the girls.”

A few minutes later the Carlsons left and everyone retired to bed.

The next morning I was up before anyone else, and started a pot of coffee. Mrs. Benson came into the kitchen a while later and I poured her a cup of coffee. “I could get used to having someone waiting on me like you do,” she commented, with a smile.

“What had you planned for breakfast?” I asked her.

“How about pancakes and bacon?”

I immediately started the breakfast, while Mrs. Benson sat and savored her coffee. “Would you like me to warm that up?” I said, pointing at her coffee cup.

“Yes Mommy, if you please,” she said with a big smile.

I was flipping pancakes when Mr. Benson and the girls showed up in the kitchen. “Something smells awfully great,” said Mr. Benson.

“Chris did everything,” Mrs. Benson said, “all I did was sit here and drink coffee.” She turned to the girls, and asked, “Did you girls have a nice New Years Eve?”

“Oh yes,” responded Susan. “Can we do it again?”

“Maybe,” Mrs. Benson answered, “We’ll have to check it out with Chris.”

On my way back home, I reflected that all in all it had been an enjoyable and profitable evening. I ruminated on how Mrs. Benson and Mrs. Carlson had made reference to me as a Mother, even if it was in fun. Maybe there was a bit of truth in it. I had to admit that I liked being a ‘Mommy.’

***

My first counseling session for the new year was two weeks after New Year. “It’s time to evaluate your progress so far,” my Counselor said, “so I’ve asked Dr. Werner to join our team. I understand that you might already have met him.” Let me call him in.

Dr. Werner was the same Mr. Werner for whose boys I had babysat. What followed was a whole lot of consents from everyone, since I knew Dr. Werner from outside of the counseling center. I liked Dr. Werner and was happy to have him on my ‘team.”

“One of the problems with this is that I may hear things about you outside of these four walls which might influence me. If you don’t like that, I’ll bow out of the case,” Dr. Werner said.

“What have you heard about Chris?” Mother asked.

“That he is the best babysitter one could ask for. Also there is the opinion that he would, or will, make a great mother,” Dr. Werner replied.

My Mother just beamed.

“Now Chris,” he continued, “I understand that when you sit for girls, you dress in feminine clothes, and when you sit for boys you dress as a boy. Is that true?

“Yes,” I replied, “It just happened that way,” and I explained what had occurred.

“Do you like dressing as a girl, wearing dresses or skirts?” he continued.

“I do,” I said, “it kind of feels just right.” I answered.

“I see,” he said. “How about when you dress as a boy?”

“Well, I really have to for school, or when someone might see me and connect the boy Christopher with the girl Christine.” I replied, “It doesn’t bother me to dress like a boy, but if I could I would always dress like a girl. And then there are the occasions when I dress somewhere in between, when I think that it would be a good idea.”

“From what I’ve heard, you make a very convincing girl,” he added.

“Thanks,” I responded.

“Any problems at school?” he asked.

“Not really,” I answered, “most of the kids think I’m a weird boy with a funny haircut, and pretty much ignore me. One thing I have to watch for is acting like a girl when dressed like a boy.

“Oh?”

“Yeah,” I responded, “I have, or maybe had, a friend named Tom. His Mother saw me sitting and walking like a girl, and she found out that I cross dress. She told me to never be alone with Tom. She told me that Tom’s Dad is a homophone.”

“Do you ever see Tom anymore?” he asked.

“Sure, every day at school, and when a group of kids do something, but never alone. I’m kinda scared of his parents.

“Do you ever have sexual urges when you are near Tom?” was the next question.

“No,” I replied.

“Tell me about other friends?”

“I’m sort of friends with some of the girls at school, especially if we went to grade school together, but we’re not close, we don’t share confidences,” I said.

“How about boys?” he asked.

“For the most part, I am friends with some boys from grade school, but not close. I’m pretty much a loner.” I answered. “And then there’s Joe,” I added.

“Joe?” he asked, “tell me about him.”

“He’s probably my closest friend. I’ve known him for ten years. We hang around with each other a lot. He’s the only boy who’s ever seen me in a dress, other than my Halloween costume.”

“Anything sexual there?”

“Yes, I’d guess you’d say so if you’d call a kiss sexual,” I answered. I looked at Mother to see her reaction. She was frowning. I decided to be less than candid about Joe and me.

“So you kissed him?” Dr. Werner asked.

“Or he kissed me,” I said, completing the question.

“How did that make you feel?” he asked.

“As a boy, I was disgusted,” I said, “but the girl deep inside of me kind of liked it.”

At that point the time was up and the session ended. On the way to the car, Mother said, “I didn’t know that about Joe. Maybe you should stop being his friend.”

“Oh Mom,” I complained, “Joe’s the only real friend I have. I can handle him. Don’t worry about him.”

***

The next day Joe stopped at my house to study for a test. Mother gave him a strange look, which was not lost on Joe. “Your Mother looked at me kind of funny,” he said to me, “Do you know what that’s all about?”

“Yeah, she thinks that you’re after my body,” I answered.

“Well, she’s right,” he responded.

The Babysitter - Part 4

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Violence

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

Permission: 

  • Posted by author(s)

The Babysitter - Part 4.
By Pentatonic

It was an ugly late January day. Gray skies, sleet, and dirty snow on the ground. Joe and I were walking to my house to study. “My church is having a Valentine’s Day party for teens,” Joe said, “You interested?”

“Maybe, depends,” I answered.

“Depends on what?” he asked.

“Like is it couples only? Do you have to pay to get in?” I replied. I didn’t want to go as a couple with Joe. I asked about an admission price, since there are not as many babysitting jobs in late January, and my funds were running low. I was sure of one thing, Joe had very little or no available cash.

“I think it’s open to any teen, but there will be couples there,” Joe said, “I think that they charge something to get in, to pay for the refreshments, and stuff like that.”

“Will there be dancing?” I asked.

“Yeah, I think so. They’ll probably have a CD player.”

“Are you going?” I wanted to know.

“If you will,” Joe said.

“You mean, like a date?” I asked.

“Yeah, well sorta,” was his evasive reply.

“Well, either it is a date or it isn’t. Which is it?” I demanded to know.

“It is a date,” he said.

“As in a boy and a girl?” I asked.

“Yeah, I guess so.” Another evasive answer.

“If we’re going as a couple, who’s the girl, or do you plan on two boys as a couple? I don’t think that would be a good idea, Rumors would be sure to follow,” I said.

“I kind of figured that you’d be the girl, since you already have some dresses, and you’re better looking than I am,” Joe posited.

“I’ll agree with you that I’m better looking than you, but why do you always want me in a dress. Isn’t it your turn?” I asked, “or is it that you have some evil intentions to have your way with my tender body?” I had to smile when I said that.

I paused for a moment. “I have to think about it,” I added, “If I get a babysitting job for the same evening, I’m taking the babysitting job over a Valentine’s Day party. Anyway, no matter what, I’m not going as a girl.”

The matter of the Valentine’s Day party was dropped when we arrived at my house and started to study. Ever since Mother had found out that Joe and I had kissed, we did our studying at the kitchen table, in plain view of everyone, as opposed going up to my room. This pleased Mother.

Just before Joe left, I penciled in the date of the Valentine’s Day party on the family calendar. My sister Emily saw me do this, and she came over to see what I had written. “OOH, Tinkerbell is going to a Valentine’s Day party,” she crowed, “are you going with Joe, like on a date?”

I just shot her a dirty look, but Emily wouldn’t let it drop.

“Hey Tink,” she continued, “I have a nice red dress which you can borrow. How does that sound to you Joe? Think that Tinkerbell would look nice in red?” Emily didn’t expect a response, so she left the room laughing.

“Mother!” I complained loudly. “Make her stop.”

“Just ignore her,” was my Mother’s useless advice.

***

I had a babysitting job with the Werners that weekend, so I drew an action movie from the library and looked at the rules for some card games. I wanted enough to keep the boys interested.

I had been unhappy that Mother had heard about Joe and me kissing. I didn’t mind telling the counselors; I just didn’t want Mother to know. So when I arrived at the Werner’s house, Mrs. Werner was still getting ready and I asked Dr. Werner if we could talk for a minute.

“Sure,” he said, “is this part of your counseling?

“Yes,” I answered, “When I admitted that Joe and I had kissed, it upset Mother. There are some things that I’d rather that Mother not know about, but I think that you as a counselor should know. Is there any way I could have a session without Mother in the same room?”

“I see your point,” he answered, “I can arrange that your sessions be one on one with the counselor. Don’t worry about it.”

“Thanks,” I said, “it means a lot to me.”

***

A week before the Valentine Day party, Joe and I were walking to his house from school. “Joe,” I said, “I’ve been thinking about the party next weekend. If I go, I’m not going as part of a couple. You and I can go, but not together. It’s that or nothing.

“I guess that means you won’t be wearing a dress,” he said.

“You’ve got that right,” I responded, “but that doesn’t mean that you can’t wear a dress,” I added with a chuckle.

So it ended up that Joe and I went as singles, not as a couple, and neither of us wearing a dress. There were a lot of kids who were there without dates, so coming as a single was not a problem. There were a fair number of girls, and it was a lot of fun mingling with them. Having an older sister who made me learn how to dance meant that I was a fair dancer, a lot better than most of the boys there, which meant that I did a lot of dancing.

My friend Tom was there, and after a while he and another boy came over to Joe and me.

“Joe, Chris, I’d like you to meet Fred, a friend of mine. He goes to a different school, so I don’t think you’ve ever met him. We shook hands and exchanged greetings. Then something unusual happened; I caught Fred ‘checking me out.’ I knew what this was since I had been checked out by boys who thought I was a girl, but this time I don’t think that I looked like a girl. Then I saw him check out Joe.

I noticed that while Joe and I danced with a lot of girls, neither Tom nor his friend Fred danced with any of the girls. I also noticed that they touched each other more than usual for two boys. I pointed this out to Joe.

“What do you think?” I asked Joe,

“They’re acting a lot like a couple.”

“Are they an item?” I asked.

“Could be,” Joe answered, “but then that’s not our concern.”

“I’m not sure,” I responded. “Did you see Fred checking you out?”

“Yeah, but he also checked you out, and you are much more checkable than I am.”

“Oh well, it’s not my concern,” I concluded, “or yours, unless you want it to be.”

“You’re the only one I’m interested in,” Joe said. “It’s a shame that we can’t dance together.”

“No, it isn’t a shame,” I declared, “if we danced, you’d probably try to have your way over me.”

“And that’s bad?” Joe said with a smile.

“You’re hopeless,” I said, and nothing more was said about Tom and his friend Fred.

Several of the girls made it plain that they would like to date me and we exchanged phone numbers. Over the next week some of them called me, much to the evil delight of Emily, who referred to them as my harem. “Hey Tinkerbell, another one of your harem called. Do you think she wanted to discuss clothes? Did you tell her about the fetching blue dress that you love to wear?” she said.

***

On the day before the actual Valentine’s Day, decided to make good on my intent to give Joe a pair of panties as a Valentine’s Day gift. I first dressed myself in panties, slip, bra and dress and headed off to a nearby lingerie shop. I had been sneaky getting Joe’s measurement. His waist size was easy. It was on the leather label on his jeans. His hip size, which was important, took more effort. I was able to wrap a string around his hips saying I wanted to compare my hips to his because I thought that my hips were getting bigger. I think he went along with it, not because of my weak excuse, but because I let him rub my butt when I measured him In any event, I had the measurements, and I was able to figure out that a size 5 panty should do the trick.

I found a darling pair of pink satin panties with little red hearts and with lace at the waist and leg holes. I’m smaller that Joe, so when I brought them to the register the clerk questioned the size, but I assured her that it was correct. I told her I had a big butt.

I put tissue paper around them and put them in a little box, which I decorated with a big red ribbon and a bow.

When I went to Joe’s house on Valentine’s Day to study, I brought my present with me. We were studying algebra, and during a pause, I said, “Joe, I have a Valentine’s Day present for you, and handed it to him.

“I didn’t know that we were exchanging gifts,” he said.

“We’re not, I don’t expect a gift in return,” I told him.

He carefully opened the gift, and when he saw what it was, he was surprised, and he began to blush. “I want you to wear them under your regular clothes, and feel the silky softness.”

***

Of all the girls which I had met at the Valentine’s Day party, one, Sue Hitchcock, kind of interested me. Not that she was a raving beauty, she was rather plain and a bit overweight, but she had a delightful personality. We talked several times on the phone, and I steeled my courage and asked her out for a date for the next Saturday, to catch a movie and pizza. When Joe found out he accused me to two-timing.

“Why do you want to go out with her?” Joe asked.

“Because I’d like to see a movie without someone pawing all over me,” I replied.

Sue wanted to see a new movie, which was definitely a ‘chick flic.” I certainly had no objection to that. When we sat down in the theatre, she took my hand in hers and smiled at me. After a time, I put my arm around her shoulders and she snuggled up to me. During one particularly romantic part of the movie she put her finger on my cheek and turned my face toward her. She leaned her head toward mine, and I felt her lips on mine. I squeezed her a bit, and kept my lips on hers.

I had no idea what to do next, if anything, since the farthest I’d ever gone was a kiss, except for Joe’s groping, and I didn’t think Sue wanted me to grope her. “You’re awfully shy,” she whispered to me, “I like that about you.”

***

Joe showed up at my house the next day, and boy, was he nosy. “Did you kiss her?” he demanded to know.

“A gentleman never kisses and tells,” I said smugly.

“That means you did, otherwise you would have said that you didn’t kiss her,” Joe posited, “Did she let you touch her tits?” I ignored that question. “You never let me touch your tits,” he said accusingly.

“How could I,” I said, “I don’t have any tits for you to touch.”

“That’s beside the point,” he said.

“No it isn’t,” I said, “I think that you’re more than a little jealous. Why don’t you go on a date with one of the girls you met at the party?”

“No money.”

“Lame excuse,” I said, “If you really wanted to go on a date, you’d find a way to get some cash. I think that the real reason is that girls scare you.”

“You don’t scare me,” Joe replied.

“That’s because I’m not a girl,” I responded.

***

St. Patrick’s Day was just around the corner. While my family didn’t do much about it, Sue’s family did. They were going to have an afternoon feast on corned beef and cabbage, and had invited a lot of their friends. Sue invited me, and I accepted. I told my mother about the invitation and asked her what I should wear.

“Green!” Emily interjected. “You know, maybe like that little green dress that Tinkerbell wears. I’m sure that your new girlfriend would love that,” she added with a laugh.

Mother and I ignored her. “You don’t know if it is casual, so you should overdress a little and wear a coat and tie. If it isn’t casual, you’re okay. If it is casual, you can take off the coat and tie. You might want to consider getting a green tie for the spirit of the occasion.”

That turned out to be good advice. I was able to find a green tie, and wore it with my only sport coat. When I arrived at Sue’s house, most of the men were wearing coats and ties. “I like your tie,” Sue’s Mother said with approval.

Sue took my hand and introduced me to everyone there. After that, I was talking with one of Sue’s cousins, “Sue has a kind of possessive look on her face. She better not catch you chatting up another girl, or there may be a cat fight.”

Sue and I were alone for a few minutes, when she said, “Do you like me?”

“I do, why do you ask?”

“Well, we’ve kissed, but you never tried anything further with me, and I wondered,” she said.

“I didn’t think you wanted me pawing and groping you.” I answered, remembering how I didn’t like Joe’s advances.

“Ever the gentleman,” she said. “I like that about you,” and she kissed me. “By the way, girls don’t send out engraved invitations when they want to go beyond just kissing.”

At that point, Sue’s Mother came into the room, saw Sue and I holding on to each other, and beat a hasty retreat. “Your Mother saw us,” I said.

“She did, but did you see how quickly she left,” Sue observed. “She must like you and want to encourage our romance, which is why she left so quickly.”

“Oh.” I said.

“You haven’t have a lot of experience with girls, have you?” she asked.

“Um, well, no,” I mumbled.

“How sweet,” she said with a big smile.

Sue and I continued to date, much to Joe’s chagrin, and I didn’t need that engraved invitation, but she let me know when I went too far.

I came to really love dating Sue, even if I wanted to be a girl. Boy, was I confused.

***

The weather in March can be just as miserable as it is in January, and on the last Saturday of the month Joe called. I could tell that there was something wrong, by the tone of his voice. “Is your mother home? We need her to drive us.”

“What’s wrong? What happened?” I asked.

“It’s Tom. His Dad caught him in bed with Fred, doing you know what, and he kicked Tom out of the house. Tom’s sitting on the curb with his clothes in garbage bags. We have to pick him up and bring him some place warm and dry.”

I explained to Mother what was going on. She put a complaining Emily in charge of Ann, and we headed off to Joe’s house. Immediately after Joe was in the car we drove to Tom’s house, and found him sitting on the curb, crying. Joe went over to Tom and picked him up and hugged him. Meanwhile I popped the trunk and loaded the garbage bags. We were there only a minute before Tom’s Father came outside, yelling, “I don’t care where you take that queer fagot, just get him out of my sight. I never want to see him again, and tell him to never come back here!” It was actually very frightening, with the yelling and crying.

“Okay, where to now?” my mother asked when we were all back in the car.

“Maybe my house,” Joe said, “we have a spare bedroom for Tom.”

We got Tom and his belongings into the house, and Joe sat with Tom on the couch, cradling Tom in his arms.

“You need to get a hold of your parents, Joe,” Mother said.

“I already did, before I called you. They should be here in about a half an hour.”

Mother sat on the couch with Tom between her and Joe. “Honey, your friends are here for you. Remember we are here to support you. You’re not alone,” she said.

When Joe’s parents arrived, Joe filled them in with what happened. “Should we contact the authorities?” Mother asked to no one in particular.

“Maybe I should call Tom’s mother,” Joe’s mother suggested.

Joe’s dad knelt in front of Tom. “Did anyone hit you?” Tom nodded his head, and between sobs, he said, “Yes, my dad.”

“Where did he hit you, on the face?” Joe’s dad asked.

“That should be obvious,” Joe said, “look at his black eye and swollen nose. The swelling is getting worse by the minute.”

“He needs to see a doctor,” Joe’s dad said, but first we need to call the cops. He then went to the phone, and dialed 911. He related what he knew to the dispatcher.

“The police should be here soon.” he reported.

A half an hour later a police car arrived, and Mr. Glynn, Joe’s dad told the officer what he knew. The officer squatted in front of Tom. “Is that what happened?” he asked Tom. Tom nodded his head. The officer then lifted up Tom’s head and looked at the black eye and swollen nose. The officer then stood up and keyed his radio. “I have a minor who was beaten by his father and thrown out of his house. Black eye and maybe a broken nose. I don’t know if there are any further injuries but he has a bump on his head, so he may have a concussion. He’s at a friend’s house. I think he needs medical attention.”

Two more officers and a child welfare officer arrived, followed by the fire department ambulance. One officer stayed to write up a report and the others left with the ambulance.

“What’s going to happen to the kid’s father,” Mr. Glynn asked the officer.

“Can’t say,” the officer said, “Someone else will make that decision.” When he was finished with his report, he thanked us and left. Shortly thereafter Mother and I returned home.

***

What happened to Tom was very unsettling. While I didn’t mind talking about it with Joe and Mother, I didn’t want to talk about it with anyone else. I felt that it was like betraying a confidence. Keeping quiet about it was a real struggle. On Monday, the whole school was buzzing about it. What I heard from some of the kids was nothing like what really happened, but I took no steps to correct any misconceptions.

On the next Saturday, I was at Sue’s house, just enjoying each other’s company, something I really liked to do. After a while, she said, “Remember the Valentine’s Day party? Do you remember a boy named Fred?”

I could hardly forget, given what happened to Tom.

“He was hanging around with your friend Tom,” she said. “You might remember that Fred goes to my school. Well, somehow word got out that Tom and Fred were fooling around with each other, if you know what I mean, and some homophobic bullies dragged Fred into the locker room and really beat him up. I heard that Fred had to go to the hospital. Fred hasn’t been back to school since, and someone said that his parents pulled him out of school.

“What happened to the bullies?” I asked.

“The haven’t been back to school either, maybe they were suspended or expelled, or maybe, I hope, they’re in jail.”

The thought of what had happened sent chills down my spine. If some one had connected Christine with Christopher, the same could have happened to me. Boy, I thought, have I been naive, and I vowed to be more cautious in the future.

I wondered what had happened to Tom. No one had seen him or heard from him since his Father beat him up and kicked him out of the house. I really began to hate his Father. Two young lives ruined.

It was some time later that I found out that Tom’s Mother had moved away, and took Tom with her. I suspected that it would be a long time, if ever, before I heard from Tom.

***

In mid-April I turned fifteen, although it was no big deal. I was still too young to be able to drive. For dates with Sue I had to get someone to drive me or take the bus, which wasn’t too safe at night.

One time, Mother suggested that Emily drive for my date with Sue. I didn’t like the idea, and told Mother. Emily just sneered. “If you don’t want me to drive, I guess you’ll have to use some pixie dust and fly, Tinkerbell.

To celebrate my birthday, my parents ordered pizza and bought a store made sheet cake. Both were okay, but only okay, not great.

After the traumatic events of the spring, I appeared to be less anxious to transition, a fact which was not lost on my counselor, a result of which was that nothing was done, one way or the other. In fact, I was anxious to transition, but now I was scared.

One day, Sue and I were looking at a book about movies, and she paused at the page describing the movie “Tootsie.” Can you imagine a guy wearing a dress and makeup?” she asked. “I mean, could you?”

I hadn’t planned to tell Sue about my cross dressing quite yet, but here was a question that needed me to answer. “Well, actually, yes.”

“What!” she exclaimed with surprise.

“I wore a witch’s costume for Halloween last year,” I admitted, intentionally omitting any mention of other cross dressing.

“You mean with a dress and makeup, and all that?” she questioned.

“Yes, all that,” I answered. “The Mother of some of the kids for whom I sit had put together a witch’s costume. A long black dress, with long sleeves and high neckline, along with a witch’s hat.” I left off any mention of what I wore under the dress or that it had a long slit up the left side.

This talk of cross dressing piqued Sue’s interest. “I wish I could have seen it,” she said.

Nothing was said as she examined my hair, face, and body structure. At last she said, “Yes, you could pull it off, and wear a dress and makeup.” Another pause followed as she considered what she said next, “Could I see you in a dress and makeup?”

“A bad idea, given what happened to Tom and Fred.”

“Yeah,” she agreed, “but if we could do it somewhere private.”

“Private places are in short supply,” I commented.

“Where did you put on the witch’s costume,” she asked.

“At home. I had to have Mother’s help,” I rejoined.

“Then we could do it there.” she suggested.

“Then there would be a problem, my sister Emily.” I advised her

“Why? She could help,” she said.

“Her kind of help would be more of a hinderance than help,” I responded, “she would probably have a lot of ideas, all of them bad, and some worse than others.”

She didn’t let it drop. “Still, a little mascara and lipstick . . .”

“No,” I said, trying to bring this conversation to an end.

***

A week later, Sue was visiting me at my house. Her visit was Mother’s idea, probably to see if Sue was suitable daughter-in-law material. Of course, Emily inserted herself in the conversation.

“Chris was telling me about his Halloween costume,” Sue mentioned to Mother.

“Oh yes, it was a great costume,” Mother said. I noticed that Emily had started to giggle.

“What’s so funny?” Sue asked, not quite understanding.

“Oh, the dress was great,” answered Emily, “It had a big slit up the left side, coming up to here,” she added, pointing to mid-thigh on her leg.

Before I could object, Emily continued, “But that’s not the best part. Ask him what he had on underneath the dress.”

“No! Enough! I’m sure that Sue doesn’t want to know,” I complained.

“I’m sure she does,” countered Emily. “Well, if he doesn’t want to tell you, I will.”

“Mother!” I complained, “tell Emily to shut up.”

“Given Chris’ objections, I’m sure that you now really want to know,” crowed Emily, “a black slip with four inches of lace at the hem, and long enough to be visible under the slit. Oh, we can’t forget the black pantyhose and high heeled boots,” Emily added with a smirk.

By now I was beet red, half from embarrassment and half from anger at my sister.

Emily was not finished. “Even if we couldn’t get the witch’s costume, Tinkerbell and I are about the same size, and I’m sure that I could find a dress which he could wear.”

“Tinkerbell?” questioned Sue, and the whole ugly story of why Emily called me Tinkerbell had to be brought out, over my strenuous objection.

I was ready to explode by the time the conversation was over.

Later, Sue told me that she would like to see me in a dress, “It would explain some things,” she said.

“Like what?” I challenged.

“My friends have said that you are a little effeminate. I’d like to see how feminine you’d look in a dress, with pantyhose, high heels and makeup.”

After this disaster of an afternoon, I was sure that my romance with Sue was over, but she assured me that it was not. “I kind of like effeminate boys,” she explained, “That was one of the things that initially attracted me to you.”

***

Sue and I continued to date through the end of the school year, after which he parents sent her to an art camp. While there, she fell in love with a “Hunk,” as she said. Our parting was more or less amiable, but she said that she had changed her mind and she wanted a man who was more “Manly.” I was hurt, but not to much, because I could not see where our romance was going.

My Mother wanted to console me. “There are lots of girls out there for you. You’ve just to get over your shyness a bit, and you’ll find another girl. After all, you’re only fifteen, way too young for a serious relationship.” She was right, but I wondered whether I really wanted another girl

Another positive: with the breakup Sue didn’t get to see me wearing a dress.

Joe thought the breakup wasn’t a bad idea. He reminded me of a Samuel Butler quote: “It is better to have loved and lost than never to have lost at all.”

The Babysitter - Part 5 - Conclusion

Author: 

  • Pentatonic

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Estrogen / Hormones

Other Keywords: 

  • Nursing School

Permission: 

  • Posted by author(s)

The Babysitter - Part 5 - Conclusion
By Pentatonic

After the incidents with Tom and his friend Fred, I decided that I had to be careful. I had acquired a girlfriend and, other than babysitting jobs, I did not appear outside in feminine attire. This was protective camouflage; to the outside world I was just a regular teenage boy.

Memorial Day is an exciting time for me. That is the weekend the community pool opens, and there are Memorial Day picnics. I had to decline an invitation to a picnic with the Bensons, because I wanted to be very careful of who saw me wearing a dress or skirt. Because the Benson’s daughters had only seen me as a girl, I couldn’t magically show up as a boy. However, Joe’s church was holding a picnic, and Joe invited me to attend.

“If I go to your picnic, it’ll have to be as a boy,” I told Joe.

“No skirt? Huh?” he answered.

“No. All the people who were at the Valentine Day party saw me as a boy. Heck, I’m even dating a girl I met there. It wouldn’t work. As a matter of fact it might be dangerous,” I explained.

Emily, true to form, was a royal pain. “Ooh, Tinkerbell has a date to a picnic,” she declared when she found out. “I’ve got a pair of hot pink short shorts you could borrow,” she added.

“For your information, it’s not a date,” I responded, “and I’m not going to wear any short shorts, no matter what color.”

“So Joe’s going to wear them,” she teased.

“No one is going to wear them. You’re just jealous because you’ll spend the Holiday sitting around the house all the time I’m at the picnic.” I had her there. She had just broken up with her latest boyfriend, and no one else had stepped up to fill his place.

“I’ll tell you what,” I added, “I’ll let you drive me there.” Emily had her driver’s license.

“I’m not taking you anywhere if you’re not wearing a dress or skirt,” she said.

“Mother!” I complained, “Emily’s being difficult.”

“Emily,” Mother said, “if I tell you to give Chris a ride to somewhere, you’ll do it, or else you’ll lose your driving privileges.” With this, I stuck my tongue out at Emily. I would have asked Mother to tell Emily to stop being difficult, but I knew that the chance of Emily stopping being difficult was like trying to keep the sun from rising in the morning.

***

The picnic, while nice, was nothing special. I had brought a German potato salad, and there was a lot to eat, including a plethora of pies, At least I ate well. The entertainment was home grown; someone had set up an electric keyboard, and members of the choir sang old favorite hymns. Because I can play the piano and like to sing, I found this enjoyable and softly sang along with them. But not too softly, because the Pastor heard me. “Do you need another singer?” he asked the choir in general. They did, because I ended up singing with them. During a break, I sat down at the keyboard and played.

“Not only does he sing, but he also plays the piano,” the Pastor exclaimed, “how about joining our choir?”

“I’ll think about it,” I said.

While at the picnic, a girl came up to me. “You’re Sue’s boyfriend, aren’t you?” she asked.

“Yeah, I guess so.” I replied.

“I don’t see her here,” the girl said, “How come?”

“Her family had somewhere else to go, and I’ve got a babysitting job this evening.” I said.

“Oh,” she said, “If you two break up, give me a call,” and with that she gave me a slip of paper with her name and number on it.

As it turned out, Sue found a new love at art camp, and when she came back home, she dumped me. Hardly a newsworthy item, but this girl, Cathy Samuels, heard about it and didn’t hesitate to call me. Emily likes to be close to the phone and answer it. When Cathy called, Emily announced, “Hey, Tinkerbell, there’s a Cathy on the phone for you.” Thankfully, Cathy didn’t hear what Emily said.

“I hear that Sue dumped you,” Cathy said. That’s quick, I thought, Sue only did it a few days ago.

“Yeah,” I responded.

“How come?” Cathy asked.

“I don’t know what Sue might have told you or your friends, but she seems to have found the new love of her life at art camp. What did she tell you?”

“Pretty much the same, and that you are shy around girls, inexperienced, and a little bit effeminate,” she answered.

“Does that bother you?” I asked.

“Not in the least,” she said. “I’d kind of like to be with a boy who can connect with his feminine side, because I think he can understand me better than some macho hunk.”

“Well, as you know,” I admitted, “I’m a long way from being a hunk.”

“So, when are we going to go out together? How does Saturday sound?” she said. Wow, I thought, I’ve just had a girl ask me out for a date.

“Sounds good to me,” I replied, “how does miniature golf sound to you.” It sounded good to her, and we spent some time just talking, like boyfriend and girlfriend.

All during my conversation with Cathy, Emily hung around like a vulture. “Ooh, sounds like Tinkerbell has a date.”

“Mother,” I called out, “tell Emily to mind her own business and leave me alone.”

“Emily,” Mother said, “leave your brother alone.” As expected, this had no effect on Emily.

“But Mother,” Emily whined, “It’s not fair. Sue dumps him, and a week later some hussy calls and he has a date. When I dump someone, it takes me weeks to get another boy to ask me out.”

“That’s because I’m not only prettier than you, but I’m nicer,” I rejoined, “and Cathy’s a nice girl, not a hussy.”

“Maybe you’re prettier when you wear a dress,” Emily replied. “By the way, does that Cathy know that you like to wear dresses and skirts,” she said with an evil look on her face.

“No, and she’ll never know!” I insisted.

“We’ll see about that,” Emily said to herself.

I had just about my limit of Emily’s teasing, and I complained to Father. This brought some results. “Emily,” he stated, “this teasing has gone too far. There is a line between friendly teasing and plain meanness, and you’ve pole vaulted over that line. Someone might hear your snide comments and put Chris in physical danger. It will stop this instant, or there will be severe consequences to you.” Dad listed some of the consequences he would impose for any breach on the part of Emily.

***

One day after a swim at the pool Joe and I were walking home. “What is it about you and girl friends all of a sudden?” Joe demanded to know.

“You ever heard the expression ‘hide in plain sight’?” I said, “after what happened to Tom and his friend, I’m just trying to fit in with the other guys who have girl friends. No one will know that I’d rather be a girl, not if I’m dating girls.”

“But what about us?” Joe asked.

“You’ll always be my closest friend,” I replied. “I just want to keep things cool.”

After a minute of silence when Joe and I digested what had been said, I said, “Cathy has a friend, maybe you could ask her out and we could double date. Cathy and I are going to play miniature golf on Saturday, and it would be a lot of fun if you and Cathy’s friend could join us.” Joe took my advice and we set up the double date.

***

It was shortly after the double date that I mentioned to Cathy that I was thinking of going to the community pool. “I usually ride my bike to the pool. If you have a bike, maybe we can meet there,” I suggested. When I mentioned this to Mother, Emily had to butt in. “You could borrow my string bikini,” she said, “but you’d have to find something to put in the bra.” I ignored her as well as I could, and reminded her what Dad had said.

When I met Cathy at the pool, she was the one wearing a string bikini that left nothing to the imagination.

When it came time to go home, I decided that, as a gentleman, I would escort her to her house, and go home from there. When we arrived at her house, there was no one home. There was a note on the kitchen table, directing Cathy to take a casserole out of the refrigerator at a particular time and put it in the oven. “They won’t be home for hours” she said, as she led me to the couch. We were sitting close to each other, with her arms around my neck. I could feel her breasts against my arm, and we kissed, long, lingering kisses, but nothing more. About an hour and a half later that she suggested that I go home, so I wouldn’t be there when her parents returned. I rode home, savoring the afternoon.

***

It was later in the summer that my counselor noted that my puberty was starting. “You’ve told me that you’ve been dating girls since the spring. Do you still want to become a girl?” she asked. I assured her that I did, and that my dating was to hide this fact from the world. I’m not sure that she believed me/

“Well, then we should talk about hormone therapy,” she said, “there are several different hormones, and each preforms a different function. For starters, we could try a testosterone blocker and some form of estrogen and progesterone. If you do, you will notice some changes in your body. You probably will like it that your breasts will start to grow. The down side is that you will have mood swings, and it is possible that you will develop a severe case of acne. There will come a time when it will be difficult to hide the changes from your fellow students and the rest of the people you know. As I told you before, gender dysphoria in males may just end all by itself when the individual goes through puberty, and we want to rule that out.” Since I was dating girls, I suspected that she might believe that I didn’t want to transition. She just didn’t seem to understand that I put personal safety way ahead of everything else and my dating was a facade to keep me from getting beaten up.

The end result was that I would have to wait some time before starting hormones, to see what was going on in my body. I wasn’t happy about this, but the simple fact was that they had the power to prescribe the hormones, and could withhold those prescriptions.

***

Ever since the beautician had given me a pixie haircut I had devised ways to make it look more or less like a boy’s haircut. Maybe less rather than more, because one afternoon after swimming, Cathy and I were at her house. “Let me dry your hair,” she said.

“No, that’s all right, it’ll dry all by itself,” I responded, but my protestations had no effect and Cathy went to her room and returned with a blow dryer, comb and hairbrush, with which she attacked my hair. The end result was that she returned my hair to the pixie hair style.

“Wow,” she said when she was finished, “you’ve got a pixie hair style, did you know that?”

“No,” I lied.

With that she turned and stared directly in my face. “Did you know that you have a pretty face?” she asked.

“I’ve heard something like that a couple of times,” I admitted. It was a whole lot more times than a couple, but I didn’t want to disclose that.

“With a little makeup, you could be a pretty girl,” she observed. While I knew that well, this was the last thing I wanted to hear from Cathy. I hoped that she would drop the topic, but to no avail. She called her mother over to look. “Mom, look at Chris,” she said, “don’t you think with a little makeup he would look like a pretty girl?”

“I don’t know,” her Mother replied, “Maybe, but I’m not sure that Chris would like that.”

“Oh, come on,” Cathy continued, “let’s try it.”

“I don’t want to,” I protested.

“Look, no one will know. After you get a look at yourself we can wash it right off,” she said.

“And put my hair back the way it was,” I demanded, not realizing that by what I had said I was admitting to allow Cathy to apply some makeup.

When Cathy’s mother saw some makeup being applied, she said, “I didn’t think that Chris wanted you to do that.”

“He said it was okay, as long and I put his hair back as it was,” Cathy said, taking a very liberal interpretation of what I had said. Cathy left and returned with a mirror. The reflection of my face was nothing new to me; it was what I had seen countless times before when I made myself up.

“Mom, come over here and take a look,” she said.

“Very nice, dear,” her mother said without commitment and with some reserve in her voice, “but Chris can’t ride his bicycle home looking like that.”

“Could you take it off now, and put my hair back like it was?” I asked.

Cathy didn’t answer my question, but rather said, “I bet you’d look great in a dress, with some jewelry.”

I was really nervous by now, and quite unhappy, and again requested she undo what she had done.

“But I like the way you look right now,” she said. She then put her mouth close to my ear and whispered, “I like girls as well as boys. With you I can have both.” Alarm bells went off in my head.

A few days later, Cathy suggested that we go to some kind of meeting on the next Wednesday evening. “I hope not too late, I don’t want to be alone on my bicycle in the dark,” I advised.

“Mom can pick you up and drive you home,” she suggested, “how about it?”

“I guess that it would be okay,” I admitted.

That Wednesday evening Cathy’s Mom drove us to a local church. The first thing I noticed was a rainbow-colored banner above the door. “Is this an LGBT meeting?” I said with some concern, “are you . . .”

Without waiting for me to finish that sentence, she said, “Yes, come on, it won’t hurt you.”

Cathy introduced me around as her new boy/girl friend. I didn’t like that at all, because I was afraid of what could happen if that was known at school, but I don’t think anyone considered me as anything other than Cathy’s straight boyfriend, no matter how she introduced me. I found out how often the meetings are, and stowed that information in my brain for future reference.

I was beginning to understand why she had told me she liked boys who had a feminine side.

***

One day at the pool I saw Cathy holding the hand of an older girl. They came over to me. “Chris, I’d like you to meet Sandy. Sandy and Cathy smiled at each other, and kept holding hands. A short time later, Cathy pulled me aside. “We need to talk,” she said, “Chris, you are very nice, and I like you, but I’ve met Sandy, and I don’t want to continue to date you.”

Wow, I thought, dumped again, but this time for a woman. Oh well, time to find a new girlfriend to keep up the facade of being just a ‘regular guy’ as protective camouflage.

Finding a new girlfriend did not prove difficult. Anita latched on to me when she heard that Cathy and I had broken up. At first she seemed to be sweetness and innocence, but that was her facade. Underneath it she had the morals of a female alley cat. A few weeks later she met a male alley cat, and that was that. Dumped again.

A short time later I had a babysitting job for Ellen, Mrs. Sloan’s daughter. Sylvia was there when I arrived.

“How’s your love life as a teenaged boy?” she asked, knowing of my facade.

“I’ve been dumped three times,” I related, “once for a ‘hunk,’ once for a woman, and a third time for a guy with the morals of an alley cat.”

“So, no lasting romances?” she asked.

“No, I guess not,” I replied.

“You know why?” she asked.

“No, not really,” I answered.

“Did you sleep with any of them?” was her next question.

“No, of course not,” I said, almost indignantly.

“There’s your answer,” Sylvia said, rather smugly.

***

It was August when Virginia entered my life. She and I were in school together and shared some classes. I had the impression that she was shy, because I never saw her hanging out with any boys. I was at the pool with some of the guys, and she had come with a group of girls. Naturally, a group of guys are drawn to a group of girls like flies to honey. I took a chance and asked, “Are you taking the music history course this coming year?”

“Yes,” was her one word reply. It took a lot of talking to get her to respond in complete sentences. Later that afternoon one of the other girls pulled me aside. “Virginia told me that she likes you. She said that you’re not a macho boor like most guys. As you may have noticed, she is rather shy. I’ve heard that she was abused by some weirdo when she was little, and as a result she is afraid of boys.”

Virginia and I found that we had a lot in common and she began to warm up to me. We talked about music and dancing, and we found that we both liked ballroom dancing. I had learned it when Emily took some dancing classes, and I was asked to attend since the classes did not have many boys in them.

“My Dad is a member of the country club, and they are having a ‘Founder’s Day’ dinner dance coming up,” she said one day. “Dad asked me if I wanted to invite someone, and since there will be a lot of ballroom dancing, I thought of you. Would you like to go with me?”

While I was surprised, I readily accepted.

While the dance was not formal, all of the men wore coats and ties and the women wore cocktail dresses. Some of the women even wore formal gowns. I danced with Virginia, and then with her Mother. After her Mother and I returned to the table, her Mother exclaimed to all, “He knows how to fox trot, waltz, and can do the rhumba.” It appeared that a lot of the men did not have these talents, so I ended up dancing will all of the ladies at the table.

I had noticed that when I held Virginia while dancing she seemed to stiffen up. I surmised that this was a reaction to when she had been abused and she was afraid of men. However, the more I danced with her the more relaxed she became. As everyone was leaving, Virginia’s Mom pulled me aside. “Chris, we really enjoyed your company, and Virginia seems a lot more relaxed with you than with any other boy,” she confided. I had found a new girlfriend.

***

When school started, I found out that all of my class would have meetings with the guidance counselors at the school. All of us had to fill out a questionnaire to help determine what careers we might like, and this was used to schedule our classes. In addition to the questionnaire we were scheduled to meet with a guidance counselor.

“I’m impressed with your academic record,” the counselor said, “I hope that you are thinking of going on to college, in which case I think that you should look into available scholarships.” He looked at the questionnaire. “You say you are interested in a career working with children. Why is that?”

“I’ve done a lot of babysitting; I enjoy it, and making it enjoyable for the children,” I responded.

“Hmmm,” he responded, “what do you think about teaching?”

“Or maybe working in the healthcare field,” I added.

He consulted a list on his desk. “I don’t know if you’d be interested in this, but St. Luke’s Hospital here in town offers a scholarship for people in the area who want to get a nursing degree. They’ve paired the scholarship with Morgan University, which is also in this town.”

He paused for a moment, and consulted some information on his desk. “Oh,” he said, “I don’t suppose that you know any doctors. It says that you have to have a doctor sponsor you.”

My mind immediately thought of Virginia’s Dad. He’s an MD, I thought. “I might just know a doctor who might just sponsor me. Of course, the operative word is ‘might’ in this case,” I said.

The counselor handed me a sheet of paper. “Here are some of the details of the program, take a look at it and ask to see me again if you are interested.” With that the session ended.

***

Some time later I was invited to a barbeque at Virginia’s house. I have always been comfortable talking to adults, and Virginia’s Dad asked for a minute of my time. “You’re a bright and personable young man. Have you thought of a career?”

“As a matter of fact, I have,” I started to say.

“How are your grades?” he interjected.

“Pretty good, Not straight A, but a solid B+ average.” I responded.

“How about science?” he asked.

“All A’s,” I said.

“Before I interrupted you, you were going to tell me about your thoughts for a career,” he said, in the nature of a question.

“Funny you should mention it, but I recently had a conference with a guidance counselor, and he told me of a scholarship program at St. Luke’s to get a nursing degree,” I advised him.

“Maybe unusual for a boy, but not impossible,” he commented, “in fact, the scholarship committee was considering ways to attract young men into nursing. I should know, since I am on that committee.”

Bingo! I though. If I play my cards right, this may actually work. I smiled to myself.

Virginia and I continued to date, but the relationship never progressed beyond a few chaste kisses, which was perfectly fine with me and Virginia. One real benefit was that the more time I spent with Virginia, the closer I became to her Father.

After a dinner at Virginia’s house, her Father turned to me and asked, “Does your school have career days, where you follow someone for a day, to see if you’d like to do that as a career?”

“Yes,” I answered.

“Let me talk with the Director of Nursing about this, and I’ll get back to you,” he said.

“Thank you,” I responded.

Virginia’s Dad, as I later found out, was quite an important person at the hospital, because a few days later the Director of Nursing, in person, called me. We set up a day for my visit. “Come by my office some time this week so you can sign the necessary papers and I can get you a set of scrubs to wear.”

I really enjoyed learning what nursing was about. What impressed me was how much hard work it was.

***

Although it was only the start of my sophomore year in high school, I had set my goals. The first was to win the St. Luke’s Hospital scholarship and get admitted to the nursing program at Morgan University. The second was to get some progress on my transition. I had been successful in concealing this second goal from just about everyone, which I believed was necessary for my personal safety.

My first goal required that I keep my grade point average as high as possible. My dating of Virginia was a definite plus in this endeavor. Virginia and I shared a number of classes, and we were able to study together. Joe also shared many of these classes, and on weekends the three of us could be seen doing class work together. Obviously, social activities were not as important.

When mid-term grades were sent out, our diligent work was rewarded. The same cannot be said for Emily’s grades. She had come to realize that her grade point average was below what was needed for admission to a good college, but since she was a senior, now was too late to do anything about it.

As to my second goal, I had convinced my counselor that I was serious, and I started on a testosterone blocker. I told the counselor, again, that my dating was strictly for self preservation.

When Halloween rolled around it was pretty much just another day, except for taking Ann around for trick or treating. This year I did not wear a costume, much to the dismay of Emily and Joe. I told them that they just had to learn to live with it. I did keep babysitting, because I needed the money.

The holidays, and in fact the whole next spring, were unremarkable, except that I now had a driver’s license and could get a job. All of my studying had the desired effect, and at the end of my sophomore year my grade point average had improved, as did Virginia’s and Joe’s. Naturally, the study time cut into my social life, and most of my dates with Virginia were study dates.

***

When summer was nearing, I began to think about getting a summer job. As can be imagined, there are more teenagers looking for jobs than there were jobs. Here my connection with Virginia’s Dad helped me.

Virginia would not be looking for a job, since she had enrolled in a summer program at a college which would earn her college credits. The college was in another state, so Virginia would be away the entire summer. Naturally, neither Joe nor I could afford to do the same.

It was a Sunday afternoon in May, and Joe and I were at Virginia’s house, studying. Virginia’s Dad came into the room when we were taking a break. “Chris, Joe, what are you thinking about doing this summer?” he asked.

“Both of us are hoping to find a summer job,” I answered, “and I will keep babysitting.”

“The reason I asked,” he continued, “is that I’m impressed by the two of you. I talked with the facilities’ manager and he said that he could find summer jobs for both of you. They will be minimum-wage, unskilled jobs, like mopping floors or hauling trash, but they are available if you are interested.”

We were very interested, and interviews with the facilities manager were arranged. Joe and I were hired.

My camouflage remained intact. I was a brainy kid, whose girl friend was away for the summer, and who was lucky and had landed a summer job. The net result was that I was totally ignored by the other kids, which just suited me fine.

Joe’s plan was to earn enough money to buy a car and pay for insurance, and in mid-August he reached that goal. The car looked like a junk yard reject, but it ran, and got us where we wanted to go. Neither Joe nor I had taken any auto repair courses in high school, but some of the men with whom we worked knew about cars, and even took some time out to help us with keeping it running.

It appeared that Joe had an ulterior motive in getting the car. “Hey,” he said, “you could put on a nice skirt and blouse and we could drive to a secluded spot and play kissy face and huggy bear.” I made a face at him when he suggested this, even though I inwardly would enjoy it.

“In your dreams,” was my response.

***

The course work for my junior year was harder than it had previously been. Just to keep up required a lot of work. Since Joe and Virginia shared a lot of classes with me, they had to work just as hard.

My sister Emily was not admitted to any of the colleges to which she had applied. It was suggested that she enrol in the community college where they had what could be best described as remedial courses. My course work was well above what she had to learn and she was forced to come to me, hat in hand, for help. Payback time!

“Hey Chris,” she would say, “can you help me?”

“So now it’s Chris, and not Tinkerbell?” I asked.

“I’m sorry for being mean and teasing you about that,” she was forced to admit. I could see that she was at least a little sorry, so I agreed to help her.

***

Throughout my junior year, I had little opportunity to wear a skirt or dress, other than my babysitting work. Since Joe had a car, there were occasions where I would get dressed and Joe and I would drive to another town where it was not likely that Joe or I would be recognized. Naturally, I had to arrange these trips when they did not conflict with my social life with Virginia and my babysitting jobs. These occasions were few and far between.

***

The next summer, Joe and I were able to get the same jobs we had the prior summer, and we were saving up for college. As soon as I could, I applied for admission into the nursing degree program at Morgan University, and made application for the scholarship offered by St. Luke’s Hospital. My time spent with Virginia’s Dad paid off and he sponsored me.

Right after the first of the year, I began Hormone Replacement Therapy. “You know,” my counselor said, “you will begin to see the effects of the therapy, some sooner and some later. You probably will like it when your breasts enlarge and you will have some fatty deposits compatible with females. However, you will need to be patient.”

When I related this to Joe, he was ecstatic. “You mean that you’ll be getting tits?” he exclaimed, “can I be the first to fondle them?”

“Is that all you think about?” I challenged.

“Well, maybe not the only thing,” he said, “but I do think about it a lot.”

“I had hoped that as you got older you might mature some,” I rejoined.

“Not a chance,” was his response.

***

Shortly thereafter my counselor and I discussed my Real Life Experience, where I would present myself as a female full time for a whole year. I told her that I planned to start my RLE right after I graduated from high school.

“You know, if you plan to have gender reassignment surgery, I will not approve it until some time after you have completed your RLE,” she advised me, “Have you thought about how you will handle things when you are in college?”

Now there was the rub. If I was accepted at Morgan University, it would be as a male. Same for the scholarship, if I got it. If I didn’t get the scholarship it would be moot, since I couldn’t afford the tuition without it, even living at home. In any event, I couldn’t address the problem until I was accepted and had the scholarship.

Fortunately, I had joined a support group for transgendered persons. Other members of the support group had faced the same issues, and some were successful in solving the problem.

***

I knew that I would have to tell Virginia what was happening in my life. Therefore, I made plans to take Virginia out to a fancy restaurant for Valentine’s Day.

“We’ve been dating for a long time, and I am very fond of you and the time we’ve had together,” I said, “There are a lot of people who think that we should get married. However, there is a little matter which might make that impossible.”

“Chris, I am very fond of you, but don’t you think that it is a little premature to talk of marriage? We are both looking at college, and I for one anticipate that I will want to go to grad school,” she responded.

“The matter I’m talking about has nothing to do with college or grad school,” I said, “but before we talk about it, tell me if you love me.”

“As I said, I am very fond of you,” she answered, “but in love with you to the extent that I want to marry you? No.”

“That makes it easier for me to tell you about this matter. Virginia, I’m transgendered.”

For a minute, neither of us said anything.

“You mean that you want to be a girl?” she asked.

“Not quite,” I answered, “for a long time I’ve known that I am a girl, but in a boy’s body. I’ve started on hormone therapy, and right after we graduate I will dress and act as a girl, full time.”

“Oh,” she said, “that kind of rules out marriage, even after grad school.”

“Yeah,” I agreed.

“Who knows about this?” she asked, and I told her.

“You know, I think you need to tell my parents, especially my Father,” she observed.

“Yeah,” I agreed, “I think that I have to.”

She smiled. “I know it’s not funny, but I was just thinking of what my Mother will do. I think that she was sizing you up as a son-in-law. I think that Dad will be more understanding. After all, I have told both of them that while I really like you, I’m not in love with you. I’m not sure that they believed me.”

She paused. Then she said, “You want to know why I’m not in love with you?”

“I guess so,” I answered.

“I’ve always thought that you are a bit too effeminate.” She chuckled. “Now I understand why.”

“By the way, I’m not letting you off the hook,” she added, “as of now you are no longer my boyfriend. You are now officially my best female friend. I want to keep seeing you as before. Is that okay with you?”

“More than okay,” I answered, “it’s more than I could hope for.”

***

I dreaded meeting with her parents, but I knew that I had to. I steeled my courage, and told her Dad first. “Well,” he said, “That is some revelation. I need to digest that. You know, it will affect your application for the scholarship, but we might be able to deal with it. Let me think about it and discuss it with the committee. Why don’t we plan on having dinner next weekend? By the way, what name will you be using?”

“Christine,” I replied, “it keeps things easier.”

***

In due time, Morgan University advised me that I was accepted into the nursing degree program. I scheduled a meeting with the director of admissions, where I told him of my upcoming transition, and asked him if I could still attend the school. He said that I could, and that I was not the first person to do it, and they had a policy established to make it happen.

About a month later, I was advised that St. Luke’s was awarding me the scholarship. Thereafter, Virginia’s Dad arranged a meeting with the scholarship committee, and my award was amended.

***

At long last, graduation. I jumped the gun a little on graduation day and wore panties and pantyhose under my clothes for the commencement.

The next day I went whole hog and wore a dress. By this time, my breasts had began to grow, and the nipples and areola had become larger. I definitely needed a bra by now. Naturally, Joe was very interested.

***

Ever since I knew that I really am a girl, I wanted to marry Joe. Now, how to get him to propose? I decided to discuss it with Mother who couldn’t understand why I always wanted to hang around with Joe. I dressed in a ruffled blouse and skirt and sat at the kitchen table over coffee. I started the conversation.

“I want to marry Joe.” I said.

You could have heard a pin drop. After a moment she made some incoherent mumbles, and then said, more of a question than a statement, “You want to marry Joe?”

“That’s what I said,” I replied, “I want to be his wife.”

“When did you make this decision?” she asked.

“When I first discovered that I’m really a girl,” I answered, “maybe around fifth grade.”

“Fifth grade?” she said, with surprise in her voice. “You never told me,” she added, “why didn’t you ever tell me?”

“I didn’t know if you’d like it then,” I posited.

“I’m not sure I like it now,” she exclaimed. She paused. “Does Joe know?”

“Of course not, the prospective groom is always the last to know,” I said with a snicker.

“How do you plan to get him to propose?” she asked.

“Well, I’m not going to put on a short skirt, sit on his lap, and rub him with my butt,” I said.

“Seriously, how do you really plan to do it?” she wanted to know.

“You know how he always wants to see me in a dress. I’ll ask him if he’d like to see me wearing a bridal gown. He’s sure to say yes,” I explained. “I’ll steer the conversation around to see if he gets the hint.”

“And if that doesn’t work?” she questioned.

“Well, in that case, maybe I’ll put on a short skirt, sit on his lap, and rub him with my butt until he proposes.”

“You’re hopeless,” she commented.

“Really, I think that I’ll have to propose to him,” I said.

“Okay, I’m not wild about this, but tell me, when do you want to get married?” she asked.

“Maybe two years from now, after I’ve had my sexual reassignment surgery.”

At that point, Emily walked into the room, having just returned from a class. “Did you tell her?”

“I just did,” I answered.

“You told Emily before you told me?” she asked.

“Of course, sisters always confide in each other before talking to Mom,” I said.

“I don’t know if I liked it better when she was always teasing you,” Mother said.

“That’s over,” Emily said, “ever since she stopped being a snotty little brother and became my dear sister.”

***

It was time to clue Joe in. I put on a short skirt and revealing blouse, showing off my new breasts, with a little help from some rolled up pantyhose. I went over to his house, and I knew I had his attention the minute he saw me. “You like?” I asked.

“I always like it when you wear a skirt or a dress,” he answered.

“Then how’d you like to see me in a bridal gown?” I asked.

“I’d love it,” he answered, “When you going to show me?”

“Some time after you get on your knees and ask me to marry you,” I answered.

“You want to marry me?” he said.

“Yes,” I answered. “I’ve wanted to marry you since fifth grade.”

“You never told me,” he said.

“I couldn’t very well until now, could I?” I said

“I guess not,” he replied.

With that, he got on his knees and proposed and I accepted. He then sat next to me on the couch and began to rub my knee. He progressed further, and then touched my breasts. For the first time I had known him I did not stop him. After all, he was now my fiancee.

***

We were married six months after my surgery. Emily was my maid of honor and Ann a bride’s maid. He really liked my bridal gown. I gave Joe my virginity that night.

The Chorister

Author: 

  • Pentatonic

Organizational: 

  • Title Page

Audience Rating: 

  • General Audience (pg)

The Chorister

TG Themes: 

  • Sweet / Sentimental

TG Elements: 

  • Performer/Entertainer

The Chorister

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Sweet / Sentimental

TG Elements: 

  • Performer/Entertainer

Other Keywords: 

  • Singing

Permission: 

  • Posted by author(s)

The Chorister
By Pentatonic

My name is Jeff, and making music is what makes my life worthwhile. I have a Bachelor of Music Education degree and a Master’s degree in keyboard. While in college, my faculty advisor suggested the education part, because with it I could teach music in grade and high school. Perhaps my advisor had heard my performances and thought that I couldn’t make it as a concert pianist. I was good, but maybe not THAT good. Perhaps she was right, because I couldn’t find a full time job as a performing musician when I graduated. Well, I did what a lot of other unemployed graduates do in like circumstances; I went to grad school.

Suggesting the education part turned out to be a great idea. Right before I graduated, I started the process of getting a teaching certificate, and found out that I still needed a few education courses. That was another reason I went to grad school. Once I had my masters, I completed getting my certificate. I started looking for a job as a pianist. OOPS! While I had some gigs as a backup musician, I still did not earn enough to move out of my parents’ home. While kicking around the job market, I also looked into a teaching position with my teaching certificate in my hot little hands,

Music education programs at most schools do not need a full time teacher. So I looked over the requirements for an endorsement for my certificate, so I could teach a core course in addition to music. I only needed one additional course in History and two courses in English to get endorsements in both. So, it was back to the local community college, where I picked up the necessary credits to get the endorsements. Then it was back to the job market.

Those endorsements did the trick, and I found a position at the local high school where I taught freshman English, Band, and Chorus. Having a Masters was an additional bonus, because it kicked me up into a higher salary bracket. At last, enough to move out on my own. While I was in the process of packing and moving, my Mom said, “Don’t forget to pack ALL of your clothes.”

The last comment referred to my “hobby” of occasionally cross-dressing. While my parents tolerated this, it appears that they didn’t want to be reminded of it with a closet full of womens’ clothes. Luckily, I had rented a two bedroom apartment, so I had enough room for ALL of my clothes and enough room for the piano which my parents bought for me when I was only six. One of the pleasures in life was to get dressed in a gown, high heels and make-up and pretend that I was this gorgeous concert pianist and play a full program while enfemme. This had been mostly limited to those evenings when my parents were out. While they tolerated it, they just didn’t want to see it. My dressing was curtailed during college because I shared a room and didn’t have much spare money for clothes.

Since I considered myself to be a musician, even in grade school, I decided that I could let my hair grow. My hair grew, but I didn’t. I stopped growing during my sophomore year in high school and only stood 5 feet eight inches. I topped out at 135 pounds. While most of me remained skinny, by behind was not. Perhaps it was all of that sitting while practicing the piano.

I was too small for most sports, but I could run, so during high school I ran on the cross country team. I wasn’t all that good, just good enough to stay on the team. The funny part of all this was that as a team member, I was almost considered to be a “jock,” and I wore my letters proudly.

While in college, I met Amy. She was in the music program and took voice. We dated a bit but didn’t see much or each other after graduation. Imagine my surprise when I ran across her in my hometown. She told me that she had taken a job here, and a second part time job teaching chorus at St. Anne’s, a local girls’ high school. We had the occasional date and spent a lot of our free time together.

That November, she had the biggest smile on her face. “I have a soloist position for a Christmas Program. The Messiah. Maybe you could help me rehearse.”

“Sure,” I said, “I still have my piano at my apartment, and a keyboard. Maybe you could come over to my place on Friday evening. I can order some takeout, and we can rehearse after we eat/”

“That’ll be great,” she replied. “How are you stocked for music?” Well, as you could imagine, as a musician, I have a great quantity of music, most of it in cabinets and shelves in my second bedroom. By the way, the dresser and closet in this room had my “other” clothes. There was no bed in this room, just a couch, but additionally there was a low table with a mirror that I used as my vanity.

That Friday, I came home as quickly as I could and cleaned up the apartment. I made sure that my womens’ clothes, shoes and make-up were safely put away. At least I thought safely. I ordered a pizza, and it arrived about the same time that Amy showed up After we ate, I said, “Let me get my copy of the Messiah,” and I headed for the second bedroom. She followed me closely. My mind raced to try to remember if I had put away all of my girl clothes and make-up. While I really didn’t want her in the room, I could not think of an excuse to keep her out.

She immediately headed for the music collection and pulled out some scores. “Maybe we could do some of these in the future,” she said. I just grunted in reply. After a while, she started looking around the room. Her eyes fell on my sort-of vanity, and she walked over to it and began to study it with interest. Luckily, all of my make-up was in a box under the table. She reached over and turned on the lights beside the mirror and sat down. I could just about see the wheels going round in her head, as she appraised the situation, but she said nothing. A few moments later, she turned around and took in the rest of the room. “You are lucky having this second bedroom. It gives you a lot of closet space.”

I was beginning to get nervous, and I suggested we start rehearsing. She stood up, but rather than walking to the door, she headed toward the closet. I could not think of anything, except to hope that she would head out of the room. No such luck.

She slid open the closet door. I just groaned. I could see our future together disappearing in a flash. There, hanging in the closet, were dresses, skirts, blouses, slacks, tops and coats. The floor of the closet was covered with shoes. Not a single piece of male clothes. She turned to me with a questioning look on her face, which shortly turned to a smile. “Yours?” she asked.

“Mine,” I managed to squeak out, not being able to come up with an explanation that would hold water. .

“I’d like to know about this,” she said sweeping her hand around.

“No, I don’t think you would,” I stammered.

“Yes, I would. We’ve been friends for a long time, but I would never have suspected this. Not that it’s bad. Just unexpected. So, what gives?”

“Well, sit down, and I’ll try to explain it to you.” I really had expected to see her race out of the apartment, but she hadn’t. Instead, she sat down on the couch, waiting.

“I like to cross dress,” I managed to say.

“Obviously,” she said, nodding at the open closet door. “Why?”

“I really don’t know, I just sometimes feel like being a girl. I rather like being a girl.”

“I never believed you were gay, considering all the times we slept with each other,” she said in a quite voice. “Are you bi?”

“I don’t think so.”

“I’d like to see you as a girl,” she said.

“Maybe, some day,” I muttered, thinking that “maybe” might never come. No such luck.

“No, not maybe,” she insisted, “NOW!”

I just sat there, thinking that this was the end of a wonderful friendship.

She grabbed my hand and pulled me up from the couch. “Showtime!” She exclaimed. “I’ve seen your clothes,” she added, “do you have undies and other unmentionables?

I nodded my head slowly.

“In that dresser?” she added. Again, I just nodded my head.

“This I’ve got to see.” she exclaimed triumphantly, and she walked over to the dresser and started opening drawers. “Wow!” was her comment as she picked up some panties and a matching bra. “You’ve just GOT to wear this for me. Start stripping!” she commanded.

I slowly began removing my shirt and pants, and paused before removing my shorts. “Don’t try to be modest,” she observed. “after all, I’ve seen you naked lots of time.”

She stopped for a moment, and observed my hairless body. “I always assumed that you shaved your body because you were a runner. Now I know differently.” she observed.

She handed me the panties. “I need a gaff first,” I explained, and I reached in one of the drawers. I slipped up the gaff and then the panties. She then handed me the matching bra.

“How do you fill it up?” she asked, looking at the empty cups.

“Breast forms,” I replied, “second drawer down. She reach in the drawer and pulled them out.

“Wow, they feel real,” she said.

“They ought to, for what I paid for them,” I quipped. This brought a smile to her face.

“What’s next?” she asked.

“Waist nipper and pantyhose,” I managed to say, “I don’t suppose that you’d be satisfied with a pair of slacks and a blouse?” I hopefully queried.

“You’ve got that right,” she said, with a smirk on her face.

“Then in that case, a slip.”

“Full or half?” was her next question.

“Depends on what I’ll wear. If it’s a half slip, I’ll need a camisole.” She handed me a full slip with lace at the top and the hem.

I put on the pantyhose, waist nipper and the bra. I slipped the breast forms in the cups and jiggled around to get everything in place. I could feel that I was getting aroused, but thankfully the gaff was doing its job, albeit painfully.

She looked at me with a smile on her face. “I’ll pick out the dress,” she asserted, and she pulled out an emerald green dress with a flared skirt. “This ought to do the trick.”

I lifted up my arms and she slid the dress over my head. I pulled it down and wiggled to get it to sit right.

“Looking good,” she said, “now for some shoes. Have any favorites?”

“Black patent leather, with the three inch heels.” She rummage around the shoes on the floor of the closet, pulled out the shoes, and handed them to me. I put them on.

“Make-up! I assume that you know how to do make-up.”

I was tempted to say no, but I didn’t think it would fly, so I sat down in front of my makeshift vanity and pulled out my box of make-up. First, I brushed out my hair and pulled it back in a ponytail. I then began to put on my face, foundation, powder, blusher and the like. I then began work on my eyes. I decided that green eyeshadow would work, and spent a considerable amount of time to get it just right. I finished off my eyes with some mascara. A little work with an eyebrow pencil gave my eyebrows a more feminine look. I then outlined my lips, and filled them out with lipstick.

“Stand up, and let me see.” demanded Amy.

“Turn around,” she next demanded, and I obliged with a swirl.

“Wow.” she exclaimed, and took my hand. “Let’s go in the living room, and start on some music.”

“Wait,” I said, and pulled the rubber band out of my ponytail, and let my hair fall around my face, after which I tucked it behind my ears.

I smoothed the back of my skirt and sat down at the piano. “Wow, you do that like a real girl. Nobody would think that you are a guy in a dress.” I just grunted.

The next few hours were spent with George Friedrich Handel. It was pleasant, with Amy there and me looking like a girl.

At ten o’clock, I turned to her and said, “It’s ten. We have to stop, so the neighbors don’t get mad. I don’t want them coming up to complain and to see me dressed. They don’t know about my hobby.”

I got out some wine, cheese and crackers and we sat down on the living room couch. Amy sat close to me, and I put my arm around her shoulders. Suddenly, I felt her had under my skirt, moving up my thigh. “Hey,” I said.

“I had so many guys put their hand up my skirt, I just wanted to feel what it was like, and for you to feel it,” she said. “How does it feel.?

“Good,” I answered, “but it becomes painful with the gaff.”

“Then take it off,” she responded, “and maybe take off the dress, we don’t want to have to send it to the cleaners.”

I turned and Amy unzipped me. I pulled the dress off, reached under my slip, pulled my pantyhose, panties and the gaff down my legs, and then stepped out of them.

“Come on,” she purred. “Let’s go into the bedroom. I’ve always wanted to make love to a woman.”

“But I’m not,” I responded.

“Close enough. How’s your tongue doing?” she chuckled. “By the way, what is your girl name?”

“I don’t have one.”

“How about Jenny?”

“Okay.”

Hand in hand we went into the bedroom. Sufficient to say, it was different and wonderful.

Thereafter, we practiced several times each week, and I dressed each time. Amy told me she really liked it that way. I was very happy she did, because I liked it as much as she did.

Finally, it was the night of the performance. Amy came over to my apartment at about 3:00. “Why are you here so early?” I asked.

“Well, I thought we could eat together, and then get you ready.”

“Ready?” I asked.

“Yes, I want you to wear that green dress, and I brought a red scarf to go with it. Christmas colors, you know.”

“But I’ve never been outside dressed,” I complained.

“No time like the present,” she said.

“But what if people point at me and announce that there’s a guy in a dress. I might get arrested.”

“That won’t happen. You look too convincing,” she reassured me.

“But what if I have to take a pee? It’s a long performance. Where do I go?” I said frantically.

“Use the lady’s,”

“But if I’m discovered I’ll be arrested.”

“Then don’t get discovered. Just make sure you sit to pee.”

“But my voice.”

“Then don’t talk. Anyway, if you do talk, keep it short. You’re a high tenor. If fact, your voice is a lot like a woman’s. Keep your voice high, use head tones, and speak softly,” she explained.

“Do it for me.” she said, “I’ll make it worth your while later.” I wasn’t sure about the alternative, but I didn’t think it would be good or that I would like it.

So, I wore my green dress, the red scarf from Amy, a black wool coat and a black purse. Both of us had a score, Amy because she was a soloist, and I because I liked to follow the score during the performance. I had my ears pierced a month before, and Amy produced some cute snowman earrings for me.

My first time outside, enfemme. The first thing I noticed was the cold breeze on my legs and up my skirt. I mentioned this to Amy, and she just smiled as we walked to her car.

We arrived quite early, because the conductor wanted to go over some parts and to warm up the voices. I noticed that there were a lot of red and green outfits among the choristers. I was just standing there, score in hand, waiting. A woman with a clipboard in her hand walked up to me. “Soprano or Alto, dear?”

“Oh, I’m not singing. I’m Amy’s friend, and we came together,” I replied.

“Well, I saw that you have a score, so I assumed. . .”

“I haven’t practiced with the chorus, so I don’t think I should sing.” I responded. “I just like to follow along during the performance.”

“We have a few walk-ins, if you’d like to sing. Have you ever sung the Messiah? she asked.

“Yes, quite a few times,” I answered.

“I hate to ask this, but do you read music?”

“Yes, I have a bachelor and a masters in music, and I teach music” I replied.

“Well, then, back to my first question, Soprano or Alto?”

“Alto, but I’ve also sung the tenor part, if that matters.” I volunteered.

“We can always use tenors. Come over to the piano, and let me hear your range.”

“Okay,” I replied. I didn’t see a problem because I have a good range.

She seemed to agree when she checked me out. “You have a good strong voice, and a good range. How about singing tenor? You won’t be alone. We have some other women singing tenor, because we don’t have enough men volunteering to sing.”

Amy thought it was hilarious that I had been “roped into” singing the tenor chorus parts. Amy sang beautifully and, in general, the performance went well, or as well as could be expected from a volunteer chorus. In any event, the audience loved it.

After the performance, the singers and musicians were treated to punch and cookies. The lady with the clip board kept looking at me. I was afraid that she had “read” me, but Amy explained that she was impressed with my voice, and wanted me to sign up for later performances, and maybe try out for a solo.

“If you do, you’ll have to do it as Jenny,” Amy said with a smirk, thinking it would bother me.

It didn’t. In fact, I liked being Jenny, and looked forward to it. As I said, making music makes my life worthwhile. If I do it in a dress, that’s okay, well, maybe more than okay. An added plus is that Amy seems to like it too.

The Chorister Part 2

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Sweet / Sentimental

TG Elements: 

  • Fancy Dress / Prom / Evening Gown

Other Keywords: 

  • Singing

Permission: 

  • Posted by author(s)

The Chorister - Part 2
By Pentatonic

Let me start off by saying that my name is Jeff, but sometimes I go by the name of Jenny. Yes, I’m a transvestite. Last Christmas my girl friend, Amy, had a solo in ‘The Messiah,’ and I was helping her rehearse. I have music degrees and teach music at a local high school. Well, when Amy was at my apartment for rehearsals, she discovered my girl’s clothes and insisted that I wear them, not only for rehearsals, but also when I attended the performance.

On the day of the performance, the chorus call was two hours before the performance, and since I drove to the hall with Amy, I was standing around wearing a rather fetching emerald green dress. Since I knew The Messiah, one of the choral directors roped me into singing, and that evening asked if I would be willing to join the chorus, and maybe do some other singing and perhaps a solo.

A week or so later, Amy and I were at my apartment. At Amy’s insistence, I was wearing a gray woolen skirt that came to about three inches above my knees, along with a gray sweater and gray panty hose. Oh, of course, gray 4 inch heels. Amy turned to me and asked, “Have you thought about joining the chorus?”

“Maybe,” I replied. “I noticed in the program that the chorus has open auditions coming up after the first of the year. Maybe I’ll try out.”

“For what part? Alto or tenor? As Jeff or as Jenny?” she asked.

I have a high tenor voice. “As a tenor, and as Jeff,” was my answer.

Amy frowned at my answer. “I’m not sure I like that answer. You could handle both alto and tenor, and if you auditioned as Jenny, you would be available for both parts. Anyway, I like you as Jenny.”

I just grunted.

“Guys grunt, girls don’t,” she exclaimed.

“But I’m a guy.”

“Said the boy in the skirt and heels,” she rejoined, and laughed at her own cleverness. “You don’t look a lot like boy right now.”

I stood up and smoothed down my skirt. Amy leaned forward and slapped me hard on my behind. “You’ve got a nice big butt, and it really fills out that skirt. It would be a shame to waste it in a pair of men’s slacks.”

I do have a rather large butt. While I stopped growing taller during my sophomore year in high school, my butt didn’t stop its growing. I am 5 feet 8 inches, 135 pounds, with a big butt. “With your long hair and a big ass, you look a lot like a girl from behind,” Amy commented.

“Yeah, I heard that more than once when I was going to school,” I replied.

“Too bad you didn’t grow boobs, too,” she added. I just gave her a dirty look in response. “Look, I’m not complaining,” she explained, “in fact, I rather like you, just the way you are.”

“How much do you like me this way?” I asked. She responded by taking my hand and leading me into the bedroom.

On the day of the audition, Amy came over to help me get ready. I really think that she wanted to make sure that I looked as girly as possible. “So, whatcha going to wear?” she asked.

“Slacks and a sweater,” I replied.

“Which slacks and which sweater?” she asked in a menacing tone. In response I pulled out a pair of black slacks with a side zipper from my girl clothes closet, and a sweater with a scoop neck.

“Okay,” she said. “I just wanted to make sure you didn’t try for a Jeff look.”

“Perish the thought,” I replied sarcastically.

“Then get dressed, girl,” she said.

When we got to the auditions, I noticed that the woman with whom I had talked on the night of the performance was there, with her ever present clip board. There were about a dozen girls there and two boys. “What’s her name?” I whispered to Amy.

“Mrs. Benson.” she whispered back.

Mrs. Benson walked over to us. “What’s your name, honey?” she asked. I gave her my Jenny name, my address and email. “Oh,” she added, “I spoke with you when we did The Messiah, and I heard you sing. Alto or tenor, right?”

“Either,” I replied.

“Well, having heard you sing, I don’t think you really need to audition, but, since you’re here, we may as well. Anyway, I don’t want to give the impression that I’m showing any favoritism.”

Mrs. Benson then turned around and announced, “We’ll take everyone in the order they signed in.” Since I was the last to show up, I would get to hear everyone else sing.

The first girl to audition was pretty bad. The other girls ranged from “fair” to “really good.” The two boys appeared really nervous, and it showed during their auditions. Mrs. Benson grimaced, but I am sure that the boys made the grade, if for no other reason there were not that many boys who would volunteer to sing.

At last it was my turn. “What are you going to sing, honey?” Mrs. Benson asked. I wasn’t so sure about the “honey” part, but let it go.

“‘Plaisir d’amour,’ by Martini,” I responded.

“Nice one,” commented Mrs. Benson. “Did you bring the music?”

“I have it for the accompanist. I don’t need a score.” I had studied french in high school and college, and was very familiar with the song.

“Okay, go ahead.”

Plaisir d’amour is an old french art song from the late 18th century. It is a song about the pleasures of love being fleeting, followed by pain. It is a song where you can really turn on the emotions. I gave it my all, singing it directly to Mrs. Benson. I saw her blush slightly, and I knew that I had her. When I finished, I just stood there. No one made a sound for quite a while.

“Oh my God!” Mrs. Benson finally said in a hushed voice. “That was wonderful,” she said after another pause.

“What other musical tricks do you have up your sleeve?” she added.

“I teach music at a high school.” I added, intentionally omitting the name of the school. I was afraid that she would check up on it, and find that there was no Jenny on the music faculty of the school. “I can accompany on the piano, and conduct a choir or an orchestra.”

“I can certainly use you here. I might want you as a soloist, too,” she said. “I work with other groups, and there might be a place for you in one or more of them. By the way, do you have a demo?”

I did, but it was Jeff’s demo, not Jenny’s.

“I can make up a CD with some songs. Any in particular you want?”

“Definitely what you sang today. I’ll let you pick out what ever you want, but please include some alto and some tenor songs. By the way, do you need an accompanist?

“No, I do my own accompaniment. I record my voice first, and then dub in the accompaniment,” I responded.

“You must be pretty sure that you will stay on pitch, if you do it that way,” she commented with a smile.

On the ride back to my apartment, Amy turned to me and said, “You really flirted with poor Mrs. Benson, you vixen.”

“Who me? Flirting?”

“Shamelessly. If you came as Jeff, she probably would want to seduce you,” Amy added.

“How about me as Jenny? After all, we don’t know what turns her crank,” I added.

“I’ll tell you this. You turn my crank both as Jenny and as Jeff. I don’t want you turning anyone else’s crank.” she warned me.

A few weeks later, I received an email from Mrs. Benson, offering me a part in a concert performance of some arias, duets and trios from various operas. I accepted.

“Too bad I can’t put this on my resume,” I mentioned to Amy.

“You could if you became Jenny full time,” she replied with a smirk. I decided to let that drop.

“Hey, I’m going to need a formal gown for the performances. Will you help me?” I asked.

“I thought you’d never ask,” she said, “how about we go shopping on Saturday. I’ll come by about 10 to help you get dressed.”

“Do I need help?”

“I don’t know, but I really like doing it.”

So, that Saturday Amy came by my apartment, carrying a bag. “Did you shower and shave everything?” she asked. I nodded my head.

“Good,” she said, “we need to pick out some nice looking clothes, including underwear.” With that she grabbed my hand and pulled me into my room where I kept my Jenny clothes. “Strip,” she commanded.

“Oh, I bought you a present in honor of the occasion,” she said and handed me a bag. I looked inside and saw some hosiery, a black garter belt, and some other things, all in black.

“There’s no panty hose in here. What’s wrong with pantyhose?” was my question.

“The garter belt will make you feel more girly and sexy,” was her answer.

“I don’t think I need to feel sexy to just pick out a dress,” I commented.

“Maybe not, but it helps,” she rejoined. “Put the garter belt and hose on first, and then your gaff and panties over the straps. It makes it easier when you have to pee. You don’t have to mess with your garter belt and hose.”

I did as I was told. Amy handed me a pair of brief black panties, with lace on the waist and leg holes, and lace in the front. Just holding them, started getting me aroused.

“Looks like I’ll have to do something about that,” she said pointing at my cock. Sufficient to say, she did.

After I put on the gaff and panties, she handed me a black bra with lace around the cups. “Here, this ought to do the trick,” she said. I put it on and slipped the forms in the cups. “When you perform you might want to use the adhesive, so nothing comes loose when you are singing,” she added. I just nodded in consent.

“We might look for a bra that will lift you up and give you some cleavage,” she said.

I gave her a frown. I didn’t know if I wanted cleavage, or at least visible cleavage. She just shrugged her shoulders and handed me my black waist nipper. “You want to have a good figure when you try on clothes,” she said. I put it on.

“What slip?” I then asked.

“Let’s try a full slip,” she answered, “and see how it looks. She handed me a black full slip with lace on the hem and the top. I pulled the slip over my head, and smoothed it over my body. I looked in the mirror. With the waist nipper and my fat butt, I had a pretty good figure.

“You look great!” Amy said, “if we didn’t have to go shopping, it would give me other ideas.”

I just gave her a disappointed look. “Later,” she said.

“I think that a dress with buttons in front would be a good idea. It’ll be easier to get on and off when you are trying on gowns,” she said. “By the way, what shoes will you be wearing for the performance? You need to be wearing those shoes when you try on long gowns.”

“How about the black patent leather, with the three inch heels?”

“Well, maybe, but you might want to think about getting a new pair. A girl just can’t have too many shoes. I’m thinking about something open toed, strappy and sexy. If you do wear them, we’ll have to polish your toe nails.”

We finally settled on a dark blue shirt dress with buttons on the front. I put in on and started with the buttons. Before I got all the way to the top, Amy said, “Leave the top two unbuttoned. Show off your body.” I gave her a dirty look. I didn’t want to show off my body and have men leering at my chest.

I then looked at her with a question on my face. “But you can see the top of my bra!” I exclaimed.

“Darn right,” she said, “it looks sexy and you need to look sexy.”

I just shrugged. It appeared we were going to do things Amy’s way.

“Okay. Hair and make-up.”

I sat down at my makeshift vanity and started with my make-up while Amy fiddled with my hair. When we were done, I stood up and checked my appearance in the mirror.

“You’re looking hot, girl,” Amy said approvingly, “just don’t try to pick up any men, or for that matter, any women. Especially no women, ‘cause you’ve got me.” I just pouted my lipsticked lips. “Oh, you vixen!” was her reaction, “I’ll have to keep a close eye on you.

At first, I was nervous walking out of my apartment in broad daylight, but no one seemed to notice. I liked the feeling of my nylon clad legs and the hem of the skirt rubbing my legs. The cool breeze on my legs and under my skirt reminded me how I was dressed. I actually liked it; I liked it a lot.

The ride to the mall was filled with girly chatter. “You seem to be picking up the girl part,” Amy commented. I did notice that when we stopped for a light, guys in the cars next to us were checking both of us out. I kind of gave me a thrill.

We parked the car, and I demurely swung my legs out first, with my knees together. Amy smiled approvingly, and we went into the mall.

At our first stop they had THE dress. It was a Halston Heritage Faille structured gown, in black with a fitted bodice, cap sleeves and a full skirt. It was made of silk and cotton, and the lining was polyester There were two problems, however. First, the v-neck showed a lot more cleavage than I had or wanted. Second, it was $725. Oh well.

After many stops, Amy found a dress which we believed might fit the bill. It was a cap-sleeve beaded-waist formal gown with rhinestone details and made of a stretch crepe fabric of polyester and spandex. It had a jewel neckline and was lined. It was $104. There was a small problem, it was 60" long from the shoulder to the hem. Being 68 inches, myself, I would need some really high heels or it would have to be hemmed.

It needed a short jacket with long sleeves, which we found and it was not overly expensive. I bought the dress and the jacket. “I think that we should try to move up the hem,” Amy said. “The problem is that I don’t have a sewing machine, otherwise I could easily do it.”

“Well, my mother does, and she is pretty good at using it,” I volunteered.

“You told me that your parents just tolerated your dressing. Do they tolerate it enough for us to go over there and hem you ball gown?” Amy asked.

“Why don’t I call my mom, and find out,” I concluded.

So, when we returned to my apartment, I called my mon. After the usual, like why haven’t you called before, and are you still trying on girl’s clothes, I got down to the problem at hand.

“Yes, I still do, and that is part of why I’m calling you.”

“Oh?”

“Well, I have some solo and duet work at a concert staging of parts of operas. It’s a paying job,” I added.

“That’s wonderful. Are you calling to invite your dad and me to the performance?”

“Well, sure, but I need a favor from you. Amy and I need to come by the house and hem a ball gown.”

“Whose ball gown?”

“Mine.”

There was a dead silence on the line.

“Mom?” I asked.

“I’m still trying to digest what you said,” my mom answered.

“You never had a problem with it before.”

“Your dad and I tolerated it, we just didn’t like it or want to see it.”

“So, I guess the answer is ‘no’,” I said resignedly.

“I didn’t say that,” my mother countered.

“While I really don’t like it, why don’t you come over on Sunday afternoon. Your father will be visiting this Aunt Emily at the retirement home, and he should be gone for a few hours. Come over about one o’clock.”

“Okay, mom,” I finally said, “Love you.”

“Your dad and I love you, too. We just wish you would get over this skirt and dress stuff.”

I didn’t want to talk about my dressing, so I just said, “Okay, see you Sunday. Bye.”

“Bye.”

After hanging up the phone, I turned to Amy and said, “It’s all set. We can go over on Sunday, and hem the dress while my dad’s away visiting his aunt.”

“Are you going there as Jenny or Jeff?” She asked.

“Jeff. But I’ll bring all my stuff and change there, after dad leaves.”

So, on Sunday, Amy and I loaded the ball gown, some of my Jenny clothes, shoes and make-up in the car and headed to my parents’ house. I was wearing panties, a garter belt, and nylons under my Jeff clothes and wore regular boy’s socks over the nylons, figuring I could get away with that. When we got there, I saw dad’s car in the driveway. “Oh oh, we better leave the stuff in the car. Dad’s still here. We’ll bring it in after he leaves.”

Amy and I visited with both of my parents until dad left to visit his aunt. When he pulled out of the driveway, Amy and I went out to my car and brought in all my stuff. I took it to my old room, and changed into my Jenny clothes and the ball gown and four inch heels. I very carefully walked down the stairs and into the living room, where my mom and Amy were talking and having a coffee.

When I entered the living room, my mother heard the rustle of fabric, and turned to look at me. “Oh my!” was her only comment.

She left the room but came back a minute later with a stool. “You’ll need to stand on this stool while Amy and I mark the hem.” With that, I stood on the stool while my mother and Amy got down on their knees and pinned up the hem. “Okay, you can step down and take off your dress,” she said.

“I want you to know that you look absolutely fabulous in that gown. If I had a daughter, that’s what I’d want her to look like.”

“You do have a part time daughter who happens to also be your son,” Amy suggested.

I could see the grimace on my mother’s face, but she said nothing. She stood up, and picked up the gown. “Let’s go up to my sewing room and get this done.”

She looked directly at me and said, “I don’t think it is a good idea to be standing around in just your undies and a slip. Let me get you a robe or something” she said. “I’d suggest that you change back into your male clothes, but we’ll have to put this back on you to make sure it is right, so you better keep on what you are wearing.”

My mother walked out of the room and came back with a pink robe. “Here, put this on,” she said.

I sat in a chair, and crossed my legs in a feminine manner, while mom attacked the hem. Amy had suggested that she do the sewing, but my mother dismissed it with a wave of her hand and said, “It’s the least I can do for her, I mean him. Amy and I got a chuckle out of her use of pronouns.

When she was done, she handed the gown to me, and said, “Put it on, and let’s make sure it is right. We walked back downstairs, and again I stepped on the stool while my mother pulled at the skirt and made little approval sounds. Finally, she said, “It looks good to me, what do you think Amy?”

“It looks great. Thank you for doing this.” She could see that I really liked this.

I stepped off of the stool, and saw that my mother was examining my made-up face. “You really look great. I see that you had your ears pierced. Wait here for a minute.”

My mother went back up stairs, and returned a few minutes later with a small box. She handed it to me, and said, “These earrings were your grandmother’s. I never had my ears pierced, so I could not wear them. I want you to have them and think of your grandmother whenever you wear them.”

I could see that both she and I were starting to tear up, and I moved to her and wrapped her in my arms. Amy came over and joined the hug.

“Thank you, mom. This means a great deal to me. This is the nicest gift I ever received.”

My mother dabbed the tears from her eyes, and said, “Why don’t you take off the gown, so we can hang it up, but don’t put on your Jeff clothes. Put your skirt and blouse back on, and put the earrings in your ears. I want to enjoy my part time daughter.

“What about dad,” I asked.

“Maybe it’s time for him to come to grips that he has a daughter, who also happens to be his son,” she answered.

We sat in the living room sipping tea until I heard my father’s car in the driveway. I stood up and said, “I don’t know if I can go through with this. I’m afraid of disappointing dad.”

“Don’t you worry about it. I’ll take care of your father’s feelings,” she responded.

When my father walked in the door, my mother said, “Frank, this is your daughter Jenny, who also happens to be your son. We’ve talked and it doesn’t seem likely that he’ll change. It is best we accept him for who she is, and love him, or her. She smiled at her use of pronouns.

“You’re not going to change?” he asked me.

“No,” my mother answered for me, “I want us to accept and love her, I don’t want her to feel that she is not a part of this family. I want her part of our lives.”

My father slumped down in a chair, and continued to stare at me. “It’s not easy, but I don’t want you to feel alienated.” After a minute, he held out his arms, and said, “Come here and give your dad a hug, Jenny.”

I went over to him, and we gave each other a big hug. I could feel tears starting in my eyes. Tears of happiness. My mascara started to run and streak down my face, but I just didn’t care.

The Chorister Part 3 - Conclusion

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Voluntary

TG Elements: 

  • Fancy Dress / Prom / Evening Gown

Other Keywords: 

  • Singing

Permission: 

  • Posted by author(s)

The Chorister Part 3 - Conclusion.
By Pentatonic

My name is Jeff. I am a musician and a music teacher. I love to crossdress. While crossdressed as Jenny I sang in a performance, and was later invited to sing in a concert as a soloist.

One evening I was sitting at my kitchen table, pen in hand, with a look of concentration on my face. I heard the door open and Amy, my girlfriend, walked in. “I’m in the kitchen,” I yelled.

“You’re still in you school clothes, Jeff,” Amy exclaimed as she entered the kitchen. The school at which I teach has a loose dress code for the faculty. Men are expected to wear a shirt with a collar. Women can just about wear anything within the scope of decency.

“Yeah, I got busy,” waving my hand at a bunch of papers which were on the table. Normally, if Amy was coming over, I would wear my Jenny clothes, which usually included a skirt.

“What are you up to?” she asked.

“I’ve got to write a bio for the concert program.”

“Well, that shouldn’t be too hard. After all, you have a master’s degree and your teaching certificate has an endorsement for English. You must have written them out for other performances.”

“Yeah, but the circumstances were different,” I said, picking up the latest draft from the table, “I’ve got to be careful. I don’t want anyone to know where I teach, because someone might put two and two together, and come up with zero Jenny’s on the music faculty at that school.”

“I see,” Amy said.

“Yeah, if anyone found out that Jenny was Jeff, the teacher, the administration would know about it in a very short time, and I could have problems.”

“Aren’t there laws to protect you?” she asked, “They couldn’t fire you, could they?”

“I just don’t know if the non-discrimination laws apply to crossdressers, but even if it does, there are other ways the school administration can get to you. First, you get a lousy annual review, secondly, they assign you to classes filled with lazy or block-headed students and blame you when your classes do miserably on the state tests. Not to mention that some parents would go nuts, After a while, they could fire you, based on the lousy reviews and low state test scores, and not because you are a crossdresser. So, you’re out of a job, and would have a hard time getting another one. You would have to hire a lawyer to pursue a complaint. So, you find yourself out of work for a year or more, with lots of legal bills, Furthermore, there is no guaranty you’ll be able to keep or get your job back.” I put my head in my hands.

“So, what are you going to do?” Amy asked.

“For starters, I’m going to write a vague bio for the performance. I’ll just say that I have degrees, without saying from where. I’ll also say that I teach music ‘at a local highschool’ with no name. I can’t put in any prior work that I have done as Jeff, and I don’t have much as Jenny.”

After a pause, I added, “And I have to get a photo, a head shot. I can’t very well use my Jeff photo.”

I just sat there, and stared into space.

“Well, you have to write the bio,” Amy said, “I’ll help you.” The two of us sat down and came up with a plain vanilla bio. It might be the shortest bio in the program, but what was written was all they would get.

A few days later, I made an appointment with a photographer. Amy came over and helped me with my makeup and hair styling. I only wore a pair of slacks, a low-cut top, and flats. I did, however, wear my grandmother’s earrings. Even with makeup and with my hair styled, I still looked a lot like Jeff. It was later that I decided to wear a wig for a new photo and when I performed as Jenny.

At the next rehearsal, I brought in my bio and photo, and gave them to Mrs. Benson. She read the bio, and looked at me with a frown on her face. “You don’t say where you went to school. You don’t say where you teach. I thought that you took your school band and chorus downstate for statewide competitions. You don’t mention that.”

She paused and looked at me. “It’s almost like you’re hiding something,” she finally said.

If only she knew.

“Oh well, enough of that,” she then said, “let’s sing.”

At the next rehearsal, she guided me to a corner, and began speaking only above a whisper. “I didn’t like your bio, too general, and too short. I thought that someone mentioned that you taught at East, so I called them to confirm. To my surprise, they told me that they didn’t have a Jenny on the music faculty, but that they did have a Jeff, with your last name. You want to tell me about that?”

I hung my head, and after what seemed to be an eternity, I said, “I’m a crossdresser. The first time you met me, I was with my girlfriend Amy. She likes it when I crossdress, and that is why I was wearing a dress. After that, things just happened, and I couldn’t figure out how to tell you. I’m sorry if I deceived you, and if you want me to withdraw from the performance, I will.”

“At this late date, that wouldn’t work. You have a remarkable voice, and we need you,” she said. “I only wish that you had found a way to come clean with me before now. We would have found a solution. As it stands at this time, you are going to have to go through with the performance as a girl. However, the problem is, with your voice, and your good looks, it is likely that you will get further offers after the concert. I’ll let you figure out how to deal with them.”

I lifted my eyes, and with a small smile, I asked, “You really think I look good?”

“Absolutely, If I didn’t find out just now, I never would have believed that you weren’t an attractive woman.”

She turned to go, but at the last moment she asked, “You aren’t, you know, err. . .?”

I got the drift of what she wanted to know. “Gay? No. Remember, I have a girlfriend, who really is a girl.”

That seemed to satisfy her, and with a smile, which contained the slightest bit of an invitation, and said, “Good,” and went to start the rehearsal.

At that point I stopped thinking about what I was and what Jenny was, and focused on my singing.

The next day I called Amy and related the events of the prior night. “She still wants you?” Amy asked.

“Yes,” I replied, “and maybe not just for singing.”

“She better not,” Amy retorted, “you’re mine, panties and all.”

“Hey, let me take you out to dinner tonight,” I said.

“As Jeff or Jenny?”

“I just got home. It was a long day,” I explained. “However, under my manly exterior, I’m wearing a camisole, panties, garter belt and stockings.”

“Does anything show?” she asked.

“I hope not,” I answered, “I’m wearing an oxford cloth shirt, which is a bit loose and heavy and loose pants, so I think my secret is safe. I have regular men’s socks over my stockings, too.”

“So, back to my original question, as Jeff or Jenny?”

“As I said, I’ve had a long day. I’m tired and hungry. I want to go as I am,” I replied.

“Well, I guess it’s okay. Just don’t make a habit of it,” she snickered.

The next rehearsal, I pulled Mrs. Benson aside. “Could I use an assumed name for the program?” I asked.

“I guess so,” she replied. “What name did you have in mind?

“I want to use my mother’s maiden name”

“That’s somehow fitting,” she said with a smile.

One potential problem was averted. So I would sing the concert using my mother’s name. Since I had got tickets for my parents, I hoped they would appreciate the choice of my stage name.

“I also had another picture taken, this time with a wig, as more of a disguise,” I added.

“Probably a good idea.”

On the day of the concert, Amy came over to help me get dressed. I had showered and closely shaved everywhere below my ears. I then filed my nails and put a dark red polish on my fingernails as well as my toenails. I had been using breast forms, and because I was a soloist, I decided that it would be a good idea if I glued them on. I put on a black garter belt, black, sheer, thigh high stockings, and then a gaff and black panties with a lace front and lace around the leg holes and waist. I lay on my bed and Amy came over with the breast forms and adhesive. I could feel her put on the adhesive, followed by the breast forms. “Don’t move right now, wait for the adhesive to set,” she warned.

After the adhesive had set, I stood up and Amy handed me a black lace-trimmed bra, which I put on, followed by a black waist nipper. I wasn’t wild about how it restricted my breathing, but it was necessary to make the gown fit properly. We had decided on a full slip with lace on the hem and the bodice. I sat at my makeshift vanity, and put a towel around my shoulders. I started with foundation to cover any possible shadow of a beard, and followed that with the remainder of my face makeup. Because I would be on stage, with stage lights, Amy and I decided to use more makeup than usual. An important part would be my eyes. I used a dark blue eyeshadow, with lighter blue highlights. I decided to use false eyelashes, and heavier eyeliner. This was followed by blood-red lip liner and lipstick. While I was doing my makeup, Amy was putting on my wig. I thought that a darker color for my wig would help my disguise. She gave my wig a soft wave. I put on my grandmother’s earrings. When Amy and I were finished, I looked approvingly in the mirror while Amy gave a soft whistle. “You look gorgeous,” she said softly.

I removed the towel and Amy went to the closet to get my gown. It was a black cap-sleeve beaded-waist formal gown with rhinestone details and made of a stretch crepe fabric of polyester and spandex. It had a jewel neckline and was lined. Very carefully, to not disturb my hair or makeup, Amy lowered it over my head, and slid it down my body. I added a jacket which came to my waist, also in black, with muted beading. I couldn’t help running my hands up and down the gown, smoothing it to my body. “Quit admiring yourself, and put on your shoes,” Amy demanded. I sat on my makeup stool and Amy knelt in front of me. She picked up a strappy, open toed shoe in black with a four-inch heel, and put it on my foot, followed by the other shoe. One could see the nail polish on my toes through the sheer hosiery.

I loved the sound of my heels clicking on the floor. I loved the feel of the slip and dress on my nylon clad legs as I walked. I picked up a black purse and stuffed some necessary cosmetics in it along with a lace-trimmed hankie and my wallet.

We decided that Amy would drive, and I carefully and gracefully slid into the car seat, keeping my knees together, even though with the long gown no one could otherwise see my panties.

I met Mrs. Benson at the stage door of the auditorium, and she looked me over with admiration and approval. “You look absolutely fabulous, honey,” she said. The other singers and I then walked to the stage and ran through some of the music with the orchestra to warm up our voices. We then went to a lounge to await the beginning of the performance.

The audience applauded when we walked on the stage. There is nothing like the rush you get from this. I smiled at the audience. The concert was a success. Everyone stayed on pitch and our voices blended nicely. The audience seemed to like it. I felt secure and comfortable with my disguise, well, as comfortable as a person can be while wearing a waist nipper.

On Sunday, I called my parents’ house and spoke with my mother. She told me how wonderful I looked and sounded. She was flattered that I used her maiden name for my stage name. I did mention that it would be best if she did not tell anyone about my performance as Jenny.

The next Monday, I was savoring a cup of coffee in the faculty lounge. One of the other teachers came up to me and said, “I went to a great concert on Saturday. It was your kind of music. I kinda thought that I would see you there.” I was tempted to say that he did, only that I was on the stage, but I kept my thoughts to myself.

“Oh?” was all I said.

“Yeah, they sang a bunch of stuff from operas. Look, I brought the program with me,” and he handed me the program. Although I had seen it many times, I kept up my disguise and read it.

“Yeah, these are great works,” I said as I looked at the program. “What did you think of the singing?” I asked innocently.

“It sounded quite good. The women who sang were really good looking, especially the alto. I’d like to meet her,” he added.

“Oh?” was my only reply. If only you knew that you met her and were speaking with her this instance, I thought, but I kept my mouth shut. Inwardly, I was pleased, because I felt that this was an unexpected compliment.

That evening I related my conversation to Amy. “Well, it looks like no one ‘read’ you,” she concluded. A wicked little grin crossed her face. “How does it feel to have a man lusting after you?” she said.

“Oh, get real,” I said, “it was nothing like that. I’m sure that wasn’t the case.”

“Oh yeah? Don’t bet on it,” she said. “You better watch out as Jenny, in case he, or any other man, sees you. They’ll want to hit on you, and be careful around Mrs. Benson.”

“Oh bah,” was my only comment, but I took her comments to heart, and decided to be more careful when I was Jenny.

Over the next few weeks, I thought about my future with Amy. While wearing the emerald green dress that started everything, I proposed to her and she accepted. “Are we going to get matching bridal dresses?” she playfully asked me, and then laughed at her own cleverness. I just made a face at her and stuck out my tongue.

I instantly realized that what I had just done was rather girly, so I composed myself, and in my most serious voice said, “That wouldn’t work. We’ll have to invite some of the faculty from my school, and they can’t know about Jenny. It would cause too many problems, and I might end up unemployed.”

“Yeah, I know. It’s just a thought,” she said.

“Not a good one. It would be fun, but no,” I added.

I looked at her for a minute, and then said, “At this time, only you, my parents, and Mrs. Benson know that I am Jenny. As far as I know, no one else knows. I’d kind of like to keep it that way. When we started with me singing as Jenny, I, for one, never saw it becoming a problem.”

“What kind of problem?” she asked.

“You know, if my school finds out about me, I would really be in trouble. I just don’t know how to handle it,” I said.

“Well, we just have to make sure that your school never finds out,” she said.

“But the more that I appear as Jenny, the more likely they will find out. After my last performance, one of the other teachers talked to me and said he thought that I would have attended. Naturally, I didn’t confess that I was there, in a dress. However, there are events in which I would be expected to be in the audience. Someone might make the connection between Jenny and Jeff, and then the cat’s out of the bag,” I explained.

Amy just sat there, digesting what I had just said. With a sad look in her eyes, she finally said, “It almost seems that you don’t want to be Jenny anymore.”

“No, that’s not true,” I responded. “I really like being Jenny, at least part time, and I don’t want to let her go. What I’d like to do is to plan for a way to be Jenny and still be Jeff at school.”

“You mean to carefully control when you appear in public as Jenny?” she asked.

“Yeah, kind of like that,” I responded.

“You could sing as Jenny,” she suggested. “Mrs. Benson knows, but you said that she promised to keep it a secret. I certainly won’t spill the beans, and I think that your parents will keep it quiet, for various reasons, not the least that they might not want their neighbors and friends to know that I crossdress

“Yeah, that might work,” I said. “I am now using my mother’s maiden name as a last name for my performances, and I have established an email account under that name. I’ll do what I can to disguise myself when I sing as Jenny.”

Amy finally let a small smile emerge on her face. “That sounds like a plan, but I think that you will have to keep Jenny’s singing career on a rather low key. No talking with the media, no interviews, no recording contracts, or anything else which will bring attention to you while you are Jenny.”

“Yeah, I think I could do that,” I said. “Do you really think it would work?”

“If you or I see the situation getting out of hand, we could have Jenny back off from further performances,” she suggested.

“How about when we go out shopping or go to dinner? It’s no secret that we are engaged. If people see you with Jenny at the mall, or out to dinner, they may wonder where Jeff is,” I said.

“That may be a problem,” she responded. “Any ideas?”

“Maybe we could put lots of miles between us and this town when I shop or dine with you as Jenny?” I asked.

“We would be seen only as Jeff and Amy around town,” she added. “Yeah, we may have to do that.”

“It’s a shame that people don’t seem to tolerate crossdressing,” I commented. “I can continue to dress, but on a limited basis. I don’t like that, but it may be the only thing I can do.”

“Yeah, but you can still be Jenny on evenings and weekends when you’re home.”

“It’s just not the same,” I complained. “I really like to go out dressed and I don’t like to be limited.”

“Yeah, but we have to compromise,” she said. “Life is full of compromises, and this is one of them. At least you don’t have to give up dressing completely.”

“True,” I responded, “I think that we have a plan that will work, even if it carries some risk of exposure.”

We then retired to the bed to celebrate our plan, wearing matching nightgowns.

The Jon Boat

Author: 

  • Pentatonic

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 7,500 < Novelette < 17,500 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Age Progression

TG Elements: 

  • Gynecomastia

Permission: 

  • Posted by author(s)

THE JON BOAT
By Pentatonic

Chapter 1. The Thunderstorm
Summer, Age 14. Before Freshman year at High School.

It was a hot, humid, summer day. My family and I were spending the summer at my grandparent’s cottage on Ringer Lake. My name is John Hoorn and that summer I was 14 years old. My father would spend long weekends with my mother and me and return home to work during the week. My mother taught school, so she had the entire summer free to spend at the lake.

Since I had spent summers at the lake for many years, I had made friends with a couple of boys my own age who lived year round in the town of Ringer Lake. One of them, Carl Bush, was my age, and like me, he was small and slender. It appears that puberty and growth spurts were taking their sweet time getting around to Carl and me.

I had picked up a rather sad looking jon boat the prior year, and had spent a lot of time sealing up the leaks, painting it, fixing the oarlocks, and replacing the thole pins. Its sole means of propulsion were two oars. It was a major part of my entertainment during the summer. I used it for fishing for blue gills, red ears and perch and exploring the more remote parts of the lake where the power boats could not go. Often times Carl would accompany me on these excursions, but for some reason I seemed to end up doing most of the rowing.

I had been taught lifesaving, but for some unexplained reason, my parents did not want me to swim alone. So. when I wanted to swim, I would search out Carl or Ralph Siddons. The interesting part of this was that Carl’s and Ralph’s parents thought that my lifesaving training made our swimming safer. Well, I went along with this because I was taught to use the “buddy system,” where you did things with at least one buddy, for safety.

My family had just come up for the summer, and the weather had turned hot, so on this hot, humid day, I was dressed in a T-shirt and old cut-off jeans. I brought a pair of old trainers, and wore a pair of flip-flops when in the boat. I embarked in my faithful water craft and went to look for Carl. Carl’s family’s house was not on the lake, so I rowed to the community pier, tied up my boat and walked to Carl’s house, which he shared with his mother and sister Emma. There was no mister Bush evident. Mrs. Bush had divorced him some years ago for reasons which I later found to be important.

Carl’s mother answered the door. “Carl went over to the library. He said that he wanted to get some books, but I suspect that he went there to just get out of the house. He shouldn’t be too long. You can wait for him here, or you can take a hike to the library.” I decided to wait for a while and cool off. It appeared that Emma also was out. She was Carl’s sister, a year older than Carl, and rather attractive.

“Would you like something cold to drink while you wait?” Mrs. Bush asked.

“Yes, if it isn’t too much of a bother.”

Mrs. Bush went into the kitchen and returned with two glasses of lemonade. “Sit down and relax,” she suggested. I sat in an old easy chair, and Mrs. Bush sat on the sofa, facing me. It had been hot work rowing that morning, so I quickly finished my lemonade and set the empty glass on the coffee table in front of my chair.

“Let me get you a refill,” she suggested, and bent over to pick up my glass. When she did that I was able to see her cleavage. For some reason, she smiled and slowly stood up. She then took my glass to the kitchen.

After seeing what I had seen, I felt a little hot and bothered. “Thank you for the lemonade, but I think that I’ll head down to the library and look for Carl.”

“You sure you don’t want more lemonade?” she asked.

“No, I’m okay,” I answered, and headed off to the library. I found Carl hunched over one of the library’s public terminals. When he saw me, he quickly switched to a different screen.

“Hey, dude. Want to go swimming?” I asked. Carl and I used to swim just about every day, but, as far as I knew, he hadn’t gone swimming so far this summer.

“Naw, I was thinking of vegging here all day.”

“That’s not a good idea. How about just kicking around town, maybe get something to eat,” I suggested.

“Are you paying?” Carl asked.

“Yeah, my mom gave me some money.” I said.

“Well, then what are we waiting for? Let’s get some hotdogs, fries and root beers, and eat them at the picnic grounds.” The town had built a shelter in a large open area, and put in some softball fields. It was generally known as the “picnic grounds,” for the lack of a better name.

“Sounds good to me,” I said, “you taking out any books?”

“Naw, I just came here to return some books and check out some stuff on the internet,” he replied.

“What stuff? Anything interesting?” I asked.

“Naw, just stuff,” was Carl’s rather evasive reply.

I figured that Carl was uncomfortable letting me know what he had been looking at, so I let it drop. I did wonder why he had gone to the library to use the internet and not use his family’s computer at home. Then it came to me: he didn’t want any record of his browsing where his mother or sister could see what he had been up to.

We made our way to the hotdog stand, and then headed to the edge of town to where the picnic grounds were located. I guess it was too hot and humid for most people, and the picnic grounds were empty. We sat at a picnic table and had lunch.

“Hey,” Carl exclaimed, “I was looking at some history of the interurban trains in this area, and there was a line not far from here. We could walk there and check it out.” The old abandoned interurban line was even further out of town. There was a dirt two track road from the town to the line.

Out here the trees had grown up and much of the road was shaded. This was good and bad. Good, because we were not in the direct sun; bad, because we could not see the sky. The first inkling that things had changed was the sound of thunder.

“Hey, it sounds like a storm is coming,” Carl said.

“Obviously,” I responded.

“Let’s head back to the picnic ground. Maybe we can get to the shelter before it hits,” Carl said in an excited voice.

No such luck. We were halfway between the old interurban line and the picnic ground when the sky opened up. We ran the rest of the way to the picnic ground, but to no avail. By the time we got to the shelter, we were both soaked.

“I don’t like the lightning and thunder,” Carl said in a frightened voice. He moved closer to me, as if I could protect him. His T-shirt was so soaked, it clung to him and was practically transparent. It was then that I noticed what looked like straps over his shoulders. I had no idea what they were.

“Hey, whatca wearing under there?” I asked, pointing to his shoulders. It was too hot to wear even a T-shirt, but wearing something under it made even less sense.

His face began to redden. “Nothing,” he replied.

“No, there’s something,” I persisted.

He just stood there, looking at me. His face was even more red. “If I tell you, you’ve got to keep it a secret. Will you do that?”

“Of course,” I said. Now I was really interested.

He pulled off his T-shirt, and there was some kind of garment there. Not having any sisters, and being rather naive about girls, I had no idea what it was. “What is that?” I asked.

“A camisole,” was his reply. I could see that it looked like something a girl would wear, but the word “camisole” meant nothing to me.

“Is that something a girl would wear?” I asked.

“Yeah, sorta.”

“Then why are you wearing it?” was my question.

“Well, sometimes they turn up the AC at the library, and it can be cold with just a T-shirt,” he offered in the way of an excuse.

I snorted in disbelief. “Come on, tell me the truth. I won’t tell anyone.”

“You promised,” he said. “The reason I’m wearing it is that my nipples have been bothering me when I don’t wear it.”

I was dumbfounded. “How is that?” I said softly.

He did not immediately answer. We stood there for a moment as the lightning flashed and the thunder rolled. He finally spoke. “Remember, you promised,”

He looked at me as if he wanted reassurance of my confidentially. “A few weeks ago, I noticed that my nipples got bigger and more sensitive. Mom took me to the doctor, and he said it was a hormone imbalance, which is not uncommon with boys our age, and the problem would eventually go away. He suggested that I wear this until then, ” he said, pointing at the camisole.

“Could I see them?” I said without thinking this might make Carl uncomfortable.

“I guess so,” he replied and took off his camisole. His nipples and his aerolae were much larger than they had been the prior summer, and his nipples stood erect. I also noticed that he seemed to have the beginning of breasts.

“Satisfied?” he questioned. “Remember, you promised to say nothing about this.”

“Okay,” I replied. “You know, they look a lot like girls’ tits.”

“Thanks,” he said, his voice dripping with sarcasm. “That is hardly something I wanted to hear from you.”

“Sorry,”

He stood there for a few moments, and then put the camisole and his wet T-shirt back on.

“Anyone else know about this?” I asked.

“Only my mom and sister, and now you. My sister thinks it’s funny as hell, and offered to lend me a training bra and some of her clothes. At least she did, until mom made her stop. My sister can be a real pain sometimes,” he added. Carl’s sister is a year older than Carl, and a very attractive teenage girl. I didn’t ask if he ever wore any of his sister’s clothes.

I looked outside of the shelter and saw that the rain had let up a bit. There still was some thunder, but it was more distant. “Maybe we could head back to your house. If we go now, it’s not likely that anyone will be outside, and they won’t see what you’re wearing”

“Okay,” he said, and we started toward his house, through the rain.

His mother was waiting for us as we entered Carl’s house. “I got worried when the storm hit,” she said, “I was hoping that you found a place to keep dry, but I see that wasn’t what happened.”

The storm had brought in some cooler air. “I think you should get out of those wet clothes, and I’ll put them in the dryer. I’ll find something for you to wear while your clothes are drying.” With that, she left the room, only to come back a few minutes later carrying a bath robe. It was pink. I put it on. It looked rather girly.

Carl looked at me, and smiled. “You want to dry your hair? I have a blow dryer in my room.”

“No, I don’t think I’ll do that. As a matter of fact, I have to take my boat home. The seats will be wet, and I’ll have to bail it out before I start, so whatever I am wearing will get wet again.”

Carl saw a flaw in my logic. “You gonna dump the water from the boat on your head?” He snickered at his own cleverness. I ignored his question.

About a half hour later I looked at the clock. “Uh, I think I better go now. It looks like the rain has stopped, and I want to get my boat back to the cottage,” I said.

“Okay,” he said, “let’s see if your things are dry.” We went to the dryer, and in fact they were dry, and still warm. I grabbed them, and looked around for a place to change.

“You can change in my room.”

“Okay.”

We walked up to his room. I expected him to leave, and give me some privacy. He didn’t. I turned around, faced the wall and took off the robe.

“Modest, are we?” he said with a chuckle. I noticed that he was intently staring at me.

I said nothing but put my clothes on. “Well, I’ve got to be going,” I said. I picked up the robe which I had been wearing, and started back downstairs to return it to Mrs. Bush.

“Thank you for everything,” I said, as I offered the robe back to her. “Well, I guess I’d better take off, before it starts raining again,” I added.

When I got to the boat, the first thing to do was to bail out the water from the rain. My PFD was soaked, so instead of putting it on, I put it on the transom seat. I sat in the rowing seat, pushed off, slid the thole pins of the oars into the locks, and started back to my grandparents’ cottage.

My mother met me at the door. “I was worried about you until Mrs. Bush called me and said that you were drying off at her place. That was very nice of her”.

“Did you have a good time?” she then asked me.

“It was okay,” I answered.

“What did you and Carl do?”

“Stuff. We played computer games until my clothes were dry.”

“What did you wear while your clothes were in the dryer?”

“A robe which she had laying around. I didn’t pay much attention to it.”

My mother gave me a knowing look. I wondered just how much Mrs. Bush told her.

Chapter 2. The Island
Summer, Age 14, continued. Before Freshman year at High School.

It was some time before Carl or I mentioned the events of the day of the thunderstorm. Then, one day, a week or so later, my parents told me that they were going back home for a few days, and suggested that I stay at the Bushs’ house during that time. My mother said that she had asked Mrs. Bush, and Mrs. Bush said she and Carl would be delighted.

After my parents left, I packed a picnic lunch, enough for Carl and me. I put two PDFs in the boat, along with my swim suit and towels. I got in my boat and rowed to the community pier near Carl’s house. I walked to the house, and asked if Carl wanted to go on a boat ride and a picnic lunch on the island. The island is actually a little peninsula in a shallow part of the lake. It really was more of an island, since the piece which connected it to the land was more like a marsh. This made the island accessible by row boat or canoe, but not suitable for hiking or motor boats. This little island had a nice smooth beach of small rounded gravel, which worked well for swimming. There was a clear area near the beach, and the guys and I had taken a picnic lunch there many times. All in all, it was rather secluded.

When I mentioned the island, Carl brightened up and said, “Maybe we could go swimming.” As far as I knew, Carl hadn’t been swimming since his “condition” had started.

“Did your, uuh . . . you know, go away? I asked.

“Unfortunately, no,” he answered. “But I don’t think that anyone will see us at the island, so it’s okay if I go swimming bare chested.

Mrs. Bush said that it sounded like a good idea, and Carl said he was going to get his swim suit and a towel. We walked to where my boat was moored, and headed off to the island.

It seems like none of my friends ever volunteer to row, and today was no exception. I sat in the rowing seat, facing backwards and Carl sat in the stern, facing me. I couldn’t help looking at him. I noticed that his breasts were just as prominent, if not more so than they had been when we were caught in the thunderstorm.

I’m a teenaged boy, and teenaged boys are not known for their tact and sensitivity, so, when we were in the middle of the lake, I decided to find out more about Carl’s “condition.”

“I see they didn’t go away. What did the doctor say?”

“He said it’s a condition known as gynecomastia, where a boy develops breasts. He said it’s usually caused by a hormone imbalance, and it usually corrects itself in a few years,” he answered.

“A few years? Bummer,” I said.

“Yeah, it is a bummer,” he said, “but there is a side benefit.”

“Huh?” I replied, not being able to see any side benefit.

“Yeah, remember when we all wanted to touch Sandy Williams’ tits?”

I remembered. We were not successful.

“Well, I don’t have to try anymore, now that I have a set of tits all of my own. I can grope and fondle them any time I want,” he said, rather ruefully.

It was almost funny, if it wasn’t for the disadvantages.

“My sister thinks it’s hilarious,” he added, “she always wants to look at them, and I even let her touch them on occasion. She told me how a girl gets pleasure when someone plays with her breasts, and she wanted to know if I did.”

“And do you, if I may ask?” I said.

“Yes and Yes,” he said, “yes you may ask, and yes it gives me pleasure.”

“What does it feel like,” I said, without regard to Carl’s blushing.

“It’s all tingly. And sometime it makes me hard,” was his response.

I silently rowed for a minute. “What are you going to do when you start school? Will you have a problem?

“I can bind them down with an elastic bandage or the doctor mentioned some kind of top I could wear. I’ve decided to join the band, and that excuses me from PE. I don’t want to even think about what some of the neanderthals at school would do if they saw them in the locker room,” he answered.

“Yeah, that’s probably a good idea,” was my comment, “Look, I don’t want to embarrass you, so if you don’t want to talk about it anymore, just tell me it’s none of my business.

“No, it’s not a problem,” he said, “you are one of the few people I can talk to about it. My mom is vague about what the doctor told her, and, as I said, my sister just thinks it hilarious. At least you, as a guy, can understand some of the problems that mon and sis can’t. You probably are the only friend I have now, since I don’t think any of our other pals would understand.”

We were now at the island, and I directed all of my attention to beaching the boat. I got it up the beach as far as I could with rowing. I then unshipped an oar, sat next to Carl to raise the bow, and pushed it further up. I did a good job, because when Carl and I got on the beach, we didn’t even get our feet wet.

I spread an old blanket on the ground and we unloaded all of our stuff, including the picnic lunch, from the boat. I had brought a portable radio in a plastic bag to keep it dry, and turned it on. Carl and I then went behind some trees and changed into our swim suits. It wasn’t long that we took to the water. When we were in the water, Carl said, “I’ve missed swimming, but you can understand that I couldn’t go swimming at the community beach.”

“Yeah, I can understand that.”

After a swim, we sat on the blanket and had our lunch. While eating lunch, I could not help but stare at Carl’s breasts. He ignored my stares for while, but finally he looked at me and put his hands over them, just like a girl would do.

“I’m sorry if I look like a freak,” he said.

“No, you don’t look like a freak,” I said, “I’m sorry for looking at them so much.”

“Now that you’ve looked, do you want to touch?” he added.

I must have turned several shades of red with embarrassment and shook my head. “It’s not a problem,” he said, “actually, I want you to touch them, just to see if having someone else fondle them makes me as tingly as when I do. I can’t very well ask my sister or mom to do it.”

His comment caused me to chuckle. He slid closer to me, until my right side was touching his left. He reached over and took my left hand and put it on his breast. “Now rub gently,” he commanded.

I did, and he made little sounds which appeared to be sounds of pleasure. “Oh, wow,” he gasped, “it’s even better.”

“Do you want me to stop?” I asked.

“No, not unless you want to,” he replied.

I closed my eyes and imagined that I was fondling Sandy Williams’ breasts. This caused a my cock to get large and hard. I opened my eyes, and tried to get it down. It didn’t behave.

While this had been going on, I noticed that Carl had put his left arm on my shoulder, while he continued to make sounds of pleasure.

Carl looked at the bulge in my crotch, and said, “Maybe we had better stop.”

I dropped my hand and Carl moved away from me.

We went swimming again, and then packed our stuff in the boat and headed back to the cottage. We went inside and changed out of our wet swim suits. Since I was spending the night at Carl’s, I packed my pyjamas and clothes for the next day and we walked to Carl’s.

Carl had a full sized bed in his room. The mattress and springs were rather old, and the whole thing sagged in the middle. That evening, Carl and I put on our pyjamas, and climbed into bed. I was slightly concerned, after the events of the day, but I figured that everything would be okay.

I was wrong.

During the middle of the night, I woke up to discover that Carl and I were “spooned” in the middle of the bed, with his breasts against my back. I moved away, and turned until I was facing Carl. It appears that he had also woken up, because he whispered, “I enjoyed what we did this afternoon.” He took my hand and put it under his t-shirt and on his breast. I began to gently massage his breast and play with his nipple. He was obviously enjoying this.

“You’re acting like a girl,” I commented, “are you sure that you’re still a boy?”

“Now that you mention it, I’m not always sure,” he answered. “Does that bother you?”

“No, I’m still your friend, whatever you want to be,” I said.

“That’s sweet,” he replied. To me, that’s something I’d expect for a girl to say, not a boy.

“Do you ever think that you’d like to be a girl?” I asked.

Carl didn’t answer me, and I was genuinely surprised when he put his hand behind my head and pulled my head towards his, and I felt his lips on mine. His actions gave me the answer to my question. I didn’t know what to do.

“I wanted to kiss you this afternoon, and I want to kiss you now,” he said, “that is, if you don’t mind.”

I grunted a reply, not being sure what to say or do. It didn’t matter, since Carl kissed me again. It wasn’t unpleasant, no, it actually was pleasant. One hand on a breast and lips kissing. Needless to say, my cock was as hard as a rock.

“I’m pretending to be a girl, since I have tits. Why don’t you pretend that I’m a girl,” he whispered. I just grunted again. He took his hand away from my head, and the next moment I felt him touch my cock. “That feels good, doesn’t it?”

I finally regained my sense of propriety, and said, “We shouldn’t be doing this.”

“Okay,” he said reluctantly, and for the rest of the night we kept our hands to ourselves.

Carl and I spent the rest of the summer with each other, but there was no more touching.

Chapter 3. The Outboard Motor
Summer, Age 15. Before Sophomore year at High School.

The next summer, when I was 15, my parents and I returned to the cottage on Ringer Lake. After we were settled in, I went to the shed and pulled out my jon boat. I set it upside down on saw horses and looked at the bottom. It needed paint. So I headed over to the marina to buy some sealing paint. While I was there, I saw an ancient 3 hp outboard, next to a pile of junk, and I walked over and looked at it.

“That outboard is older than you are,” said one of the marina employees, “hell, it’s older than I am.”

“Does it work?” I asked.

“Naw, some old guy had it in his garage, and I don’t think it’s been run for years. When he died, his children brought it in to sell it, but we told them it isn’t worth anything. It needs a whole rebuild, and even then it might not work. Anyway, all of the people on the lake want big outboards. The only thing that you can power with it is a small rowboat, and even then, it’ll be really slow.”

“How much do they want for it?” I asked.

“I donno. You want to make an offer?” he asked.

“How about $10.00,” I said.

“Write your name and phone number on this card, and I’ll ask them.”

After buying the paint and painting the bottom, I decided to stop by Carl’s and let him know I was back at the lake.

“He’s at the library,” Carl’s mother told me. You can probably find him there.”

I hiked to the library, and sure enough, Carl was there hunched over a terminal. We talked as much as we could in a library, and I told Carl that I wanted to look for a book on repairing small old outboards.

“Why would you want that?” asked Carl.

“I put an offer in for a really old 3 H.P. at the marina, and I want to see if there are any books about fixing them,” I responded. Carl just snorted as I went to the stacks.

Because the town of Ringer Lake is on a lake, there is quite a bit of interest in books on boats and motors. I finally found a very old book about repairing outboards like I saw at the marina, and I sat down near Carl and started to read it.

After about an hour, Carl turned off the terminal, stood up, and stretched. “You got any money?” he asked.

“Why,” I said.

“Because I don’t, and I’d like an ice cream cone,” he replied.

“Okay, if you check this book out on your card, I’ll buy you an ice cream cone,” I said. Since I had never got a library card for the Ringer Lake library, I could not take the outboard motor repair book out.

“Deal,” he said, “but if you let it go overdue, I’ll have to hurt you.”

I smiled. Carl hadn’t seemed to grow much in the past year, with one exception. Last summer, I found that Carl had gynecomastia, and he still had it. If anything his breasts were larger, even though he had bound them down. I really wanted to find out about what happened over the past year, but that discussion needed a lot more privacy that one would find in a library, or anywhere in town. As we walked to the ice cream stand, I noticed that Carl was walking more like a girl, and wiggling his behind. I thought about what he had told me last year about maybe wishing that he had been born a girl.

I let the paint dry on the boat for another two days, and floated it in the lake. I loaded up the oars, floatation devices and an anchor, and headed over to the community pier. From there I walked to Carl’s house.

“Hey, I’ll make some sandwiches, and we can have a picnic on the island,” Carl suggested.

“You want to go swimming too?” I asked, well aware of Carl’s gynecomastia.

“Yeah, the island is a good place, and you already know about my condition. I haven’t been swimming yet this summer,” Carl answered.

Carl and I rowed to my grandparent’s cottage, well, I rowed and Carl rode, as usual. I went inside and got my swimsuit, some towels, and an old blanket, and we headed to the island. I think that Carl liked it because it was so secluded. It was almost like a private beach.

On the way to the island Carl said, “Look, I don’t want you to get freaked out, but the gynecomastia is worse this year than last.”

That was obvious. I just grunted.

“I’ve can’t get by with just a camisole. To my sister’s evil delight, I now wear a bra some of the time,” he commented. In fact, I’m using a bikini for a swimsuit,” he said, “That’s okay with you, isn’t it?”

“If it isn’t, what then?” I asked rhetorically.

“I donno,” he said.

“Well, it’s okay with me, as long as I don’t have to wear one too,” I commented. This caused Carl to chuckle.

“Well, with your long hair, you might make an okay girl,” Carl responded. Sometimes Emma gets me dressed in girls’ clothes. Mom wouldn’t mind it if you or anyone else did, but for some reason, she doesn’t want me to. Maybe it’s because my dad dressed as a woman on occasion. My mom caught him with another man and she threw him out of the house. Maybe she’s afraid I would end up like him if I dressed like a girl.”

“Do you like wearing girl’s clothes?” I asked.

“It isn’t bad. I actually kinda like it,” he answered, “but it makes me wonder if I should have been born a girl.”

“How about your hair?” I retorted. Carl’s hair was longer than mine. “Do you ever get mistaken for a girl?”

“Yeah, it happens, especially if my tits are not bound down.”

When we got to the island, we beached the boat and unloaded it. I went behind some trees and put on my swimsuit. Carl was wearing his under his clothes and he only had to take off his jeans and shirt. As Carl had mentioned, he was wearing a bright green bikini. His breasts filled the cups on the bra. “A cup,” he commented, noting that I was staring at his chest.

“Still get a reaction?” I asked, referring to events of the prior summer where I had fondled his then much smaller breasts.

“Even more so,” he said, “you want to try it out?”

“No, I think I’ll take a pass,” I said.

“Chicken!” he said.

We ran into the water, and goofed around like two teenaged boys, well, not exactly, because I purposely tried to keep a respectable distance from him. Carl was not so inhibited, and more than once I found myself in contact with his breasts.

We got out of the water, sat down on the blanket and had lunch. After lunch, we let the sun dry us off. “Hey,” I said, “aren’t you afraid of getting some funny tan lines,” referring to the straps of his bra.

“If anyone sees these tan lines, they’re going to see a lot more, so I don’t worry,” he replied. “But since you mentioned it, maybe I’ll get a little sun all over,” and with that he took off his bra. His breasts were small but delightfully shaped, the kind any 15 year old girl would love to have.

“Holy cow!” I exclaimed.

“Moo,” he responded, cupping his breasts in his hands. We both got a good laugh out of this. This was followed by a serious look replacing his smile.

“Come here,” he said, grabbing both of my hands and pulling us closer to each other. He guided my hands to his breasts and rubbed them. “They miss your attention,” he said softly. I just sat there and rubbed his breasts.

He surprised me by grabbing the back of my head and putting our lips together. I could feel his tongue against my lips, and I finally gave in an let his tongue into my mouth. We finally pulled slightly apart. “I needed that,” he said, “its been a long time since our last kiss.”

I actually liked the kiss, and I actually liked playing with his breasts. Does this make me gay? I wondered.

“I don’t think that I’m into boys,” I said, “I really prefer girls.”

“Then think of me as a girl,” he said, “after all, I have the tits of a girl.”

“Yeah, but...” I said, leaving my statement unfinished.

“Look, I want to tell you something, but you’ve got to never tell anyone else, and that includes my mom and sister, at least for now.”

“I promised that last summer,” I said.

“No, this is different,” he said, “promise?”

“Okay, I promise, What is it that is so secret?”

“I think I’m turning into a girl. When I look at myself in the mirror after a shower, I see girl. I often wish I could wear girl’s clothes all the time and do girly stuff.”

I was dumbfounded. “But you can’t be a girl,” I said, “you’ve got a cock!”

“I’ve looked it up on the internet,” he said, “that can be changed by surgery.”

The thought of someone getting near my male parts with a knife sent chills through my body. I couldn’t understand why anyone would want to do that. “That seems drastic, not to mention painful,” I blurted out.

“From what I’ve read, it’s not that bad. Surgery one day and about a week to recover, and then they send you home,” he explained.

“You can walk after that?” I said incredulously

“Yeah, from what I’ve read,” he reassured me.

“You really want to do this?” I asked.

“I’m thinking about it,” was his response.

I was silent for a moment. “Why are you telling me this before you even talked about it with your mon?” I wanted to know.

“Mom said she didn’t want me to turn out like my father. She told me that my father thought he should have been female, and she really hated that. I don’t think telling her would be a good idea.”

“But you’re telling me,” I responded.

“You’re one of the few who know about me, and after last summer you’re still my friend. I need all of the friends I can get, and you are one of my closest.”

“If I’m gone for most of the year, and you consider me to be one of your closest friends, you need to work on getting more friends,” I suggested.

I’ve been separated from most of the guys I knew,” he responded. “They all seem to be macho types and I doubt they would understand. They may want to beat me to a pulp. But you’re different, more understanding, more in tune with me. Don’t take this the wrong way,” he warned, “but you may be more in tune with your feminine side than they are..”

“I have no desire to be a girl.” I exclaimed defensively.

“I didn’t say you should be,” he responded, “and you are taking it the wrong way.”

“Well, if you were a girl, I wouldn’t have to worry about being gay if I kiss you,” I said with a weak smile on my face.

“I don’t think you’re gay. I don’t think I’m gay. You’re a straight guy, and I’m a straight girl, trapped in a boy’s body.

This surprised me an I sat and thought about what he said, or maybe what she said. “If you have this done, I can’t call you Carl anymore,” I said.

“Try Carole,” she replied.

“You’re not thinking about doing this in the next week or so, are you?” I asked.

She laughed. “No, It’s a much more complex and takes a lot of time from start to finish.”

“Like how long?”

“I’m not sure. I’ll have get mom’s permission, and I’ll have to see psychologists first, to determine if I was born the wrong gender. After a bunch of doctors see me, I can get hormone replacement therapy. They’ll give me estrogen. After I start estrogen, I’ll begin to look more like a woman. Then there are more psychologist visits, and I can then start the real life test, where I have to dress and be a woman for a whole year before I will be even considered for surgery. I think I have to be 18 before the surgery I’m not really sure about the procedure, or if what I told you is accurate, but sufficient to say, it is a long process. While I’m going through with it, I’m going to need a lot of support from my friends. That’s where you come in.”

“That’s a lot to dump on me all at one time,” I said.

“I don’t know any other way,” she said.

“Does this mean I’ll be your boyfriend when it’s all finished?” I said.

“If you want to be.”

We sat silently for a few minutes.

“You don’t hate me for wanting to do this, do you?” she finally said. “I think that the idea of it freaks out mom.”

I thought about it, and I thought that there were a lot of guys who would beat the daylights our of her if they found out. “No, I don’t hate you,” I finally said

“Just to know that you don’t hate me now, I’d like a kiss.”

“I don’t hate you, and if you need a kiss, that’s what you will get.”

We leaned towards each other and our lips met, our tongues explored each other’s mouth, and held each other tightly.

“I needed that,” she said. She looked down at my crotch, and saw an enormous bulge. “Wow,” she said, “look what I did to you. I bet if you kissed a boy, that wouldn’t happen.”

I couldn’t be sure of that, not having the experience, except being kissed by Carl last summer.

After a few more kisses, and more fondling of Carole’s breasts and nipples, we got Carole reverted back to Carl, putting on jeans and a loose t-shirt. We packed up the boat, and went home.

A week or so later, I decided to go fishing, and I went to the marina to get some bait. I met up with the guy with whom I had left my bid for the motor. He had a big smile on his face, and said, “The motor’s yours, they took your offer. Fishing was forgotten as I rowed as fast as I could back to the cottage for the ten dollars. I rowed back to the marina, where I paid for the motor, and carried it to my boat.

I was excited about the motor, and immediately began work on it. Since Carl had no interest in mechanical devices, I was left by myself and the motor for extended periods of time between picnic lunches at the island and swimming with Carole..

Chapter 4. Confrontation and Separation
Summer, Age 15, continued. Before sophomore year.

A few weeks later, Carl showed up at the cottage.

“Ready to get your hands dirty and help me with the motor?” I asked cheerfully. Carl gave me a look of disgust. “Then what brings you here?” I asked.

“Can you come back with me to my house?” he said, “something has come up and I need your support.” His eyes were red and it was clear that he had been crying

That could only be one thing, Carl becoming Carole. We decided to go by boat, and a while later were at Carl’s house. Mrs. Bush, and Emma, Carl’s sister, were sitting in the living room with less than pleasant looks on their faces.

Mrs. Bush started the conversation. “Have you heard what Carl wants to do? He’s just like his damn father.” I didn’t even get time to grunt, when she answered her own question. “He wants to become a girl! Have you ever heard anything so silly? You’re his friend, and I want you to talk him out of it!” she demanded. “I’m so embarrassed. What will all my friends think? What will the family think? Will they think that I was a bad mother?”

It appeared that Carl had not told his mother or sister that he and I had discussed it at length, and I did not think it would be a good idea to confess that now, so I just sat there with a blank look on my face.

Carl’s sister then put in her own two cents worth. “All my friends will make fun of me. I’ll never get another date because we have a freak in the house. My life is in ruins.

What was patently obvious was that Carl’s mother and sister were only thinking about themselves, their standing in their family and community, and not one bit about Carl’s well-being. Carl just sat there silently with a wounded look on his face, and tears on his cheeks.

“You want me to talk to Carl?” I asked incredulously.

“He won’t listen to his family, and you’re his best friend. Maybe he’ll listen to you, I don’t know what else to do to get this silly idea out of his head.”

“Okay, I’ll talk to him. Alone. But I really don’t know what I can do.” I said.

“Take him up to his room and talk to him!” his mother demanded.

“I was thinking about going for a boat ride with Carl,” I said.

“Do whatever you have to do but make sure that you talk him out of it.” was the final command.

“Come on.” I said to Carl and walked to the door. Once outside he began sobbing in earnest. I wanted to hug him and comfort him, but I could see his mother and sister watching us as we left. All the way from his house to the boat, nothing was said.

“I want to stop at my cottage and get some things, and then let’s go out to the island. My idea was to get the old blanket to sit on and some snacks and something to drink.

The ride to the island was silent. Only the splashing of the oars and the creaking of the oar locks. I wished that I had got the motor working, but now was not the time to bring it up. We landed at the island, and I brought the blanket and goodies to the beach. Once there, I folded Carl into my arms and held him tightly as he sobbed. “I’m sorry to put you in this,” he said between sobs.

“You’ve got nothing to be sorry about. It’s not your fault. You told your family how you felt, and rather than getting unconditional love, they only thought about themselves. I’m the one who’s sorry, sorry that you had to get that reaction.” We finally sat down on the blanket and I continued to hold him.

“Thank you for getting me out of there,” he said, “I don’t know how much more I could take.”

I stroked his face to try to calm him down.

“I’m your friend, and I won’t let you down,” I calmly said.

“I need a kiss,” he said.

What the heck, I thought, we’ve kissed before, what difference would a few more kisses make. It wasn’t like it would make me gay. Not that being gay would be such a bad idea; at least it would protect me from having a wife as unfeeling as Mrs. Bush or Emma. I pulled him closer to me and our lips met, and our tongues intertwined. I could feel his breasts against me, and it had the expected reaction. I wasn’t kissing Carl, I was kissing Carole.

I also knew that I was not going to even try to talk Carole out of becoming a girl. Even if I were to try, I knew that I would not be successful. Anyway, I liked Carole.

We sat there for hours, with me comforting her and giving her reassurances that her decision was correct. If Mrs. Bush could have seen us, she would have been furious.

When we got back to Carl’s house he turned to me. “I think that you better go home, and not go into there. They are already extremely pissed at me, you don’t need to be around when they show how pissed they are at you for not talking me out of this.” I could see Mrs. Bush looking at us out of the window, so I though that a goodbye kiss would be inappropriate.

I decided to let things cool off before I would go back to Carl’s house. However, before I could, I received a note from Mrs. Bush, telling me that Carl had been sent to a special camp. The note did not say which camp or give an address. Mrs. Bush obviously thought that I was a bad influence.

Thankfully, I had the motor to work on, and after many hours of work, it finally returned to life. I loved to be able to sit in the stern seat and see where I was going, and I continued my detailed exploration of the lake.

Finally, late in the summer, I received a letter from Carole. She told me that she had someone smuggle it out, since she was not to communicate with anyone other than her family. She said the camp supposedly “cured” people of homosexuality and gender dysphoria. She said it was absolutely terrible and they almost resorted to torture. She had decided to claim that they were right, and that she no longer wanted to be a girl, nowithstanding that the gynecomastia was still there, making everything look rather foolish. She just wanted to get out of there. She knew that home life would be miserable, but it was better than the camp. Her letter sadly said that it was likely that I would never see her, or Carl for that matter, again. There were tear stains on the letter.

Chapter 5. Working At The Marina
Summer, Age 16. Before junior year at High School.

The next year I was 16. My parents were making noises about my getting a job. They thought that I could spend a week at the cottage, and then come home and look for a job. I knew from talking to my friends at high school, that I had zero chance of landing a summer job, since I had waited too long. Be that as it may, I knew that I had to at least make the effort.

As it turned out, I didn’t even have to try. After unloading the car and getting settled in, I went back to the shed and pulled out my boat and the little 3 H.P. ancient motor which I had brought back to life the previous summer. Since I had made sure that there was no gas in it to turn to jelly, and generally followed instructions, I felt that I shouldn’t have any problems with it. I grabbed a gas can, and loaded it and the motor on my boat. I rowed to the marina where they had a fuel pump with pre-mixed oil and gas for outboards.

I filled the fuel can and the tank on the motor and after a few pulls, the motor caught and ran. Hearing the sound, the owner of the marina turned around to look.

“Hey,” he said, “isn’t that the piece of junk you bought from us last summer?” he asked.

“Yeah,” I replied.

“You got it running by yourself?” he asked. “I see that you repainted it too. It looks and sounds great.”

“It was a bit of work, but here it is,” I proudly said.

“How old are you?” he asked.

“16”

“Got a summer job?”

“Not yet.”

“How’d you like to work here?” he asked.

I could hardly contain my excitement. “Sure,” I immediately answered.

“What would I be doing?” I wanted to know.

“Whatever I want you to do.” he responded.

“That works for me,” I said.

“Aren’t you going to ask how much you’re going to be paid?”

“I’ve known you for a few years, so I figure that you’ll be fair.” I answered.

“Good enough. For starters, minimum wage, plus an employee discount of ten percent.”

“That include gas?” I asked.

“Sure, but with that tiny motor that won’t be a problem, since it doesn’t use much gas.”

“When do I start?” I asked.

“As soon as you can. How about right now? Go in to the store and tell Edith that I just hired you, and she will get the paperwork ready.” he said.

“I better go back to the cottage and tell my parents that I have a job.” I said with great pleasure.

I told my parents, who were delighted. “Looks like all that time you put in on that motor and the boat is paying off.” my father said proudly.

The hours at the job were long. Because the weekends were the busiest at the marina, I had to work every weekend. This was hardly a problem because I loved my job, and in the course of working there I learned a lot more about boats and motors.

The down side was that I didn’t have a lot of time of my own. I didn’t see any of the boys I knew until Ralph came in to buy some gas.

“I didn’t know you were working here,” he said, ignoring the obvious.

“Yeah, all summer,” I responded, “What are you and the other guys doing?”

“I’ve got a job flipping burgers,” he answered.

“I don’t have a lot of free time, so I haven’t had a chance to look anyone up,” I said. “Do you know what Carl is doing?”

“That’s weird,” he said, “right after school let out his mom sent him to some kind of camp for the whole summer. Never told any of the guys where it is or what he is doing there.”

I feared that it was a repeat of the camp that Carl’s mom had sent him to last summer after he told her that he really was a girl in a boy’s body.

“Maybe they’re toughening him up,” Ralph added, “he had a really tough time at school this last year. He looked weirder than before, and he got picked on a lot.”

“Weirder?” I asked.

“Yeah, he was acting a lot like a girl, heck, he even looked like a girl,” was Ralph’s explanation.

I just grunted in response, and pumped the gas.

A few weeks later I heard from Carl, or rather, Carole. She sent me a letter:

“Dear John:
“I have trouble writing because I have to have my letters smuggled out of here. Mom sent me back to the same camp as last summer. It is terrible. They censor all of my letters coming in, so don’t even try to write.
“For seven days a week, from early morning to late at night they mentally work me over, telling me that I am a boy, and forget all this girl stuff. It’s kind of funny, because I look more and more like a girl. My breasts are even larger than last summer. Not only that, they hurt, because they won’t let me wear a bra or a camisole.
“I miss you and remember all the good times we had together.
“Love, Carole”

It was near the end of the summer that I found out that Mrs. Bush had sold her house and moved away. It wasn’t clear to where she had moved. It seemed that my last connection with Carole was gone.

Chapter 6. Reunion
Summers and fall, Ages 17 and 18. Before senior year at High School and before and at College.

The next summers were not remarkable, maybe aside from the fact that after only one date, Sandy Williams not only let me feel her breasts, but much more. Sufficient to say, I was no longer a virgin. It appears that my time with Carole had not affected my heterosexual life.

I continued working at the marina, moving out of a minimum wage job to one with more responsibilities and higher pay. I even collected some commissions from boat and motor sales.

That fall, I started college at one of the state universities. One weekend in late September, I went with some of my fellow students to a local pizza palace. While there, I saw a waitress who reminded me of Carole. Same color hair and eyes, but much curvier that Carole was the last time I saw her, some two plus years ago.

I made it a point to return to that restaurant, in the hope that the waitress who reminded me of Carole would wait on my table. Two nights later, it happened.

The waitress came to my table. “Hi, I’m Carole, and I’ll be...” She stopped in mid sentence and just stared at me.

“John?” she asked.

“Carole?” I responded.

“Wow, I can’t believe it. So it is you. Boy, have I missed you,” she said.

“Me too,” I replied. “Hey, can we talk?

“I’d love to. I get off work at eleven. How about we meet then?” she said.

I don’t remember much of the meal, aside from some heartburn from the grease on the pizza.

I returned to the restaurant a few minutes before eleven, and gave Carole a wave. She came over to me.

“Let me get my things, and let’s go somewhere where we can talk,” she said.

“Sounds great to me. I can’t believe how fortunate I am that I ran into you.”

“Me too.”

We found a little coffee shop not far away, ordered two coffees and sat down at a table. “Tell me everything that happened to you since I last saw you,” she said.

“Okay, but you first,” I said. “All of a sudden, after that terrible day with your mon, you just kind of disappeared.”

She then started her story.

“Right after you left, my mother called my Uncle Fred. If there ever was a homophobe, it’s my Uncle Fred. She told me that she was sending me off with my uncle, that night. She also gave Uncle Fred her side of the story of what happened. Uncle Fred is one of those kind of people who think that anything out of the ordinary is perverted. Uncle Fred told my mother that he knew of some people who ran a camp that straightened out “perverts like Carl.” I didn’t think of myself as a pervert, but neither Uncle Fred nor mom wanted to hear from me.”

“That evening I went to Uncle Fred’s house. The next day he took me to a barbershop and I got a buzz cut. A few days later, he had made arrangements for me to be sent to this camp. When the time came, he loaded me in his car and we started out. He told me to “hide those goddamn tits.” I told him that I had gynecomastia, and couldn’t.

“The camp was into deprogramming and other horrible mind activities. We were told that we weren’t and never could be girls. We were told that we were nothing but perverts and that they would get that out of us. I later found out that the camp has some attempted suicides and some successful ones. I decided, for my own protection, I would pretend that they were being successful.

“When school was about to start, Uncle Fred took me back home. My mother asked me if I had gotten that girl stuff out of my head, and, just to keep her quiet, I said that I had. Unfortunately, my body had other ideas. The hormone imbalance not only caused the gynecomastia, but was also affecting other parts of my body. My hips grew bigger and my waist smaller. She told me that with my buzz cut, I at last looked like a boy. When I looked in the mirror, I thought that I looked like a girl with a buzz cut, and a few extra parts.

“School was a nightmare. I had trouble hiding my appearance, and I was constantly bullied and picked on. My body was a collection of bruises. I was still in the band, so I was exempt from PE which was the only good thing that happened.

“Mom had already sold the house, and we moved quite a distance away. The next summer mom sent me back to the same camp. A few weeks later, it was on the news that the camp had been closed by the state for abusive practices. I didn’t write to you because if you wrote back to me, mom would go ballistic.

“Anyway, the big break came from, of all places, my sister. She had taken some psychology courses, including one which dealt with gender dysphoria. She realize that what had happened was a big mistake, and that we should all see a psychologist who specialized in gender issues.

“What came out of that was that the psychologist said that I indeed was a girl trapped in a boy’s body, not that my body could be called a boy’s body with my breasts and big butt. My hormone imbalance was more dramatic, and that I would look more female as time went on. The psychologist suggested that we all accept what was happening and that I start on hormone replacement therapy. After a lot of talk, and some unpleasant scenes, mom finally agreed.

“That fall, I started my senior year in high school. I took typing and courses on business skills, and graduated with some employable talents.

“I’m hoping to have gender reassignment surgery one of these days, and as you can see, I’m into my real life test as a female, which I have to complete before I can have the surgery. With my typing and business skills, I have landed a job with a law firm, and I wait tables to earn more money so I can pay for the surgery.

“I have a small studio apartment in the cheaper part of town, and I drive a junk yard reject. Now, how about you?”

“Nothing as exciting as your story,” I said, “I worked at the marina during the summers and graduated from high school last spring. I was accepted at the college here in town and I am looking to go into engineering.”

“Do you still have the boat?” she asked.

“No. A funny thing happened. As you can guess, I used the boat to get back and forth from the cottage to the marina. One day, this guy came to the marina. It appears that he collected antique outboards, and he came looking for old parts which we still had. He and I started talking, and I mentioned my boat and motor. He just had to see them. Well, it appears that he was looking for the exact motor that I had to add to his collection. He offered me an obscene amount for the boat and motor, so I sold them. Since I wanted a car at college, I used the money, plus a little more from my parents, and was able to get a serviceable used car.”

The coffee shop owner was making moves to close shop. We were the only customers left there. Carole looked at her watch. “Look, I’ve got to get up early tomorrow morning for work at the office, so why don’t we plan for another time together,” she said.

“Sounds great.” I replied, and we exchanged phone numbers.

After we walked out of the coffee shop, she turned and faced me. “You were my first kiss. I think about it a lot, and I miss those kisses,” she said, “could I have one now?”

I responded by embracing her and putting my lips on hers.

“Just as good as they were before, if not better,” she smiled.

Chapter 7 A Deepening Relationship
Age 18. After the reunion.

A few weeks later, Carole invited me to attend one of her group sessions. “They are for girls in transition to share their experiences and problems,” she said.

“Why do you want me to go?”

I told the group about you, how you were my friend since we were little and had supported me, and they all want to see you. Maybe they think I’m making it all up. Anyway, I want to show you off,” she concluded with a chuckle.

The group session was fascinating. There were six girls, in one stage of transition or another. They all wanted to know how I felt about Carole and what happened during high school. Carole delighted telling about our time on the island and our first kiss. All of the girls and counselor were fascinated. The girls shared their stories. One or two were sweet, the balance were from bad to horrible. My heart went out to them. They were all facing an uncertain future.

A few months later I finally decided that Carole had to meet my parents. As Carl, she was well acquainted with them, but they had never seen her as Carole. Before that happened, I felt that I needed to fill them in with what happened. They were surprised at first, but slowly came around to acceptance. I think that they saw how much I liked her, and this turned the tide. After that Carole and I visited with them on a frequent basis. They seemed to accept Carole and a delightful young lady, and over time came to like her.

We began to date on a regular basis, as well as her work schedule and my studies would allow. The dates caught the attention of some of my friends at college. “Wow, you’re going out with Carole. Lots of guys had tried to get a date with her, but you’re the only guy who succeeded. What’s your secret?” one of the guys asked.

“A 12 foot jon boat,” I replied.

“Huh? What?” he said.

“Never mind,” I answered. I certainly didn’t want to discuss my past with Carole.

One night, several months later, Carole invited me to come up to her apartment after our date. “I was able to get some beers. You want to come up and have one?” she asked.

“Sure, sounds good,” I answered.

When we were in her apartment, I plopped down on her couch. She went into the kitchen area, and retrieved two beers from the refrigerator. She sat down next to me and handed me a beer. “Cheers,” she said, as she raised her bottle up.

“Cheers, and to old times,” I said, as I raised my bottle. We both took a swig. She put her bottle on the end table and touched my cheek with her hand. I leaned over and we kissed. It was a long and passionate kiss. While we were kissing, I moved my hand to cup her breast.

She broke off the kiss, and pulled her top off. I reached behind her and loosened her bra. I moved my face down and began to lick and nibble her breast. She let out low moans of pleasure. By this time, I was as hard as a rock. Carole moved her hand down and touched my cock. I let out a little moan of pleasure.

“You like?” she asked.

“You know that answer,” I said.

With that, she loosened my belt and opened the zipper of my pants. My cock, no longer restrained, popped out and stood at attention. She moved her head down, and began licking the tip. Then she stopped for a few seconds and straightened up.

“I’ve wanted to do this ever since that time on the island,” she said, “but you wouldn’t let me then because you said it was too gay. Do you think it’s too gay now?

In response, I just kissed her again. After that she bent over and put my cock in her mouth, began to work it with her tongue, and then moved her head up and down.

I knew it wouldn’t be too long. “I’m cumming,” I blurted out. She kept her mouth on my cock as I spurted my load in her mouth. She straightened up and kissed me with my full load in her mouth. She pushed some of it into my mount, and then moved her head away. I could see her swallow.

“Swallow it.” she commanded, and I obeyed. It wasn’t unpleasant. We cuddled up with each other until it was time for her to go to bed and for me to go back to my dorm room.

A few weeks later, she again invited me up to her apartment. “Business before pleasure,” she announced.

“What kind of business?” I asked.

“I want to schedule my sexual reassignment surgery, and I really want you to go to Montreal with me, to keep me company and be my support. I’d like to know when you might be available,” she said.

“I’m working at the marina again this summer, and our slowest time is late July and early August. I could probably get some time off then. How long do you have to be there after your surgery?” I asked.

“Maybe a week or so,” she said

“Why don’t we shoot for the last week in July?” I said.

“Okay, I’ll check with everyone and let you know,” she said.

“Are we done with business?” I asked leeringly.

“I guess so,” she said with a wicked smile.

“Then pleasure.” I declared.

“Get your lazy butt off the couch and help me make it into a bed,” she said. Her couch was a convertible and made into a bed as is common in studio apartments. We pulled the bed section out, and she took some bed linens, blankets and pillows out from a compartment in the larger of the end tables. We stood on either side of the bed and made it.

“I’ll be right back,” she said, “in the meantime why don’t you lose your shoes, pants and shirt?” With that she disappeared into her combination dressing room and walk in closet. When she returned she was wearing a short silky nightgown, and holding something in her hand which she put on one of the end tables. I couldn’t actually see what it was. She climbed into bed with me and we kissed and fondled each other.

Then she sat up in the bed, with a prophylactic in her hand, which she rolled on my cock.. She then picked a tube of KY Jelly from the end table and rubbed in on my cock. She then reached between her legs and put some on her butthole.

“I want you to fuck me,” she said, “but remember I’m a virgin, so go easy.” With that she lifted her legs up, leaving her butt hole exposed. “Come to me, my lover,” she said invitingly.

I moved in close, and touched the end of my cock against her anus, and began to slowly push it in. She gasped with pain.

“Do you want me to stop?” I asked.

“No! Just keep it up, but go slowly.”

I felt the head of my penis go into her anus. “Keep on coming,” she said, and I did.

“Does it hurt?” I asked.

“It did at first, but now it feels wonderful,” she said.

I began to slowly move my cock in and out, as she moaned with pleasure.

“Don’t stop, Don’t stop,” she urged.

Suddenly she bucked up and down and almost let out a scream of pleasure. I felt some fluid squirt out of her little penis and on my stomach. With that, I shot my load. I pulled my cock out and we collapsed into each others arms.

It took both of us some time to recover, and when we did she turned and kissed me. “That was like nothing else I ever felt,” she said between kisses.

“I love you,” she said.

“And I love you,” I replied.

Chapter 8 Surgery and Matrimony
Thereafter

When the time came we both went to Montreal. I stayed in the waiting room during the surgery and sat by her side when it was finished. Her recovery was slow and painful, but a week after the surgery she was discharged and told that she could go home. We took it very easy getting on and off the plane. Standing in line was the worst, but you can’t fly without enduring it.

At long last I had her in her bed. “I’ll be gone for a while, but you have my cell number. If you call me, I can be here in twenty minutes. But before I go, I think that you should go potty once more.” Just using the toilet was a long and unpleasant process, and I did not want her getting out of bed to use the toilet if I wasn’t there.

The next day included a surprise. Carole’s sister Emma called. “How did it go?” she asked.

“Okay, I guess. She’s still in a lot of pain and not too mobile. I’m staying with her until she feels better.” I said.

“I have some time off, and if she wouldn’t mind, I’d like to take care of her for a while.”

I let Emma talk to Carole, and it was arranged that Emma would be here tomorrow. I was a little concerned after the unpleasant scene when Carole told Emma and he mother that she was transsexual. However, both Carole and Emma were very happy to see each other.

“How is your mom taking this?” I asked.

“Not as well as she could, or maybe should,” Emma replied, “Most of the time she doesn’t want to talk about it, and when she does, it is clear that she still harbors a lot of anger.

With Emma there, I could go back to Ringer Lake and my job at the marina. I kept in touch by telephone. Emma told me that Carole had used up all of her vacation, sick days, and personal days at the law firm, and that she was going back to work the next day, no matter what. She liked her job and didn’t want to lose it. As for the waitress job, she wasn’t yet up to the long work days it entailed, and the standing almost all day, and if the job was available when she felt like returning, that was okay. If it wasn’t available, that also was okay, since it shouldn’t be that difficult to find another job like it.

It was, some time later, when I was sitting with Carole at her apartment. “There’s something I want to show you,” she said, and with that she handed me three long plexiglass rods of different diameters and rounded at one end.

“What are these?” I asked.

“Dilaters.”

“What do they do?

“They keep my vagina from closing up. I have to use them until I have sex. That’ll be your job,” she said with a wicked grin, “and if you don’t they’ll find a place in your tender body.

I grimaced at the thought.

“On the other hand, you might like it too much,” she mused, “After all, I did.”

Carole didn’t need the dilaters.

It was fortunate that Carole worked at a law firm, because they took care of the name change procedure, which is done in the Court. With the name change order and a Physician’s Statement of Gender Change she got a new drivers’ license in the name of Carole Bush, showing her gender to be female.

Because she had completed the reassignment surgery and had legally changed her name, she could then get an amended birth certificate in the name of Carole Bush, a female.

At the end of Carole’s lease of the studio apartment, we decided to live together, and found a bigger apartment. We stayed there until I graduated.

Shortly after graduation, I knelt before her and asked her to marry me, and she accepted.

Emma squealed with delight when we told her about our engagement, and made it clear that she expected to be Carole’s maid of honor.

“What about mom?” Carole asked Emma.

“I’m not sure,” replied Emma, “let me talk to her.”

In the end, Carole’s mom became a typical “mother of the bride,” and seemed to accept what Carole had done.

Oh, one last thing. Carole and I bought a new jon boat as our wedding present to each other. We didn’t buy a motor, saving that for later. So, when we took the boat out, I rowed and Carole rode. Some things never change.

The Potty Policy

Author: 

  • Pentatonic

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Real World

TG Elements: 

  • F2M sex change

Permission: 

  • Posted by author(s)

The Potty Policy
By Pentatonic

Author’s note: This story is based upon an actual case decided by the Seventh Circuit Court of Appeals on May 30, 2017 in Ashton Whitaker, etc. v. Kenosha Unified School District No. 1 Board of Education, et al., case Number 16-3522. In summary, this is a case concerning a transgendered female to male student’s using the boys’ washroom at school, and his battle with the School District. The School District lost and the transgendered student won. I have taken great literary license with this case, changed names, modified facts and created dialog out of thin air. However, the ruling by the court has not been changed. Please do not rely on this story as a statement of law or legal advice.

Sarah Daniels could not be considered beautiful, or even cute. She was larger than most girls in her class, and did not have the curves associated with eighth grade girls. She looked a lot like a boy. She was physically strong and enjoyed sports.

On a warm spring afternoon after school, Sarah walked into the kitchen of her family home and dumped her book bag on the floor. “How was your day, honey?” her Mother asked.

“Okay,” Sarah replied as she walked over to the refrigerator.

“Learn anything interesting?”

“No.” she started. “Wait, Yes, In health class they talked about boys who think they are girls, and girls who think they are boys, or something like that. It got me thinking. I am more boy than girl.”

“Oh my,” her Mother responded, and then said, “We won’t be ready to eat for another two hours, why don’t you practice your music?” Mothers have a way of changing the topic when they want to avoid discussing something, like whether a daughter should be a boy.

Sarah persisted, and at dinner that evening she brought up what had been discussed in health class. “Sometimes I think that I should be a boy, not a girl. I’m not pretty or petite. I look a lot like a boy and I like doing boy kind of things.”

“But you are a girl,” he Mother said.

* * *

Sarah’s Mother did not forget what Sarah had said that evening and over the summer after her graduation, her Mother observed that she acted more like a boy than a girl. It became more difficult to get her to wear dresses or skirts. Sarah preferred androgynous clothes. Sarah had friends who were boys, but no ‘boyfriend’ as in ‘boyfriend/girlfriend.’ Sarah had some friends who were girls, but none who were close, as might be usual for girls Sarah’s age. She never tried out makeup with them, and when the girls reached puberty and developed curves, Sarah didn’t.

Before starting high school, Sarah had a frank discussion with her parents. “Mom, Dad, I’m really a boy in a girl’s body, not that my body is that girlish. From now on, I want to be a boy.” Accordingly, at the beginning of her freshman year at Riverwoods High School, she began to openly identify as a boy, He began to use the name Samuel or Sam and asked be addressed using male pronouns. As Sam, he cut his hair and began to wear more masculine clothing. This continued through Sam’s freshman year, without any significant problems.

On the first day of his sophomore year, Sam approached his home room teacher, Mrs Fletcher. “Mrs. Fletcher, I’ve decided to be a boy. Please call me Samuel or just Sam,” he said.

Mrs. Fletcher was taken aback. “Can you just decide to do this?” She looked at the home room attendance sheet. “But this has you down as Sarah, I don’t know if I can change this, It’s all on the computer, you know.”

“You don’t have to change the attendance sheet,” he continued, “Just when you see the name ‘Sarah’ just say the name ‘Sam’ and use masculine pronouns.”

“Well, err, I guess so,” Mrs. Fletcher said with an uncertain tone in her voice.

Sam repeated this for all of his classes. Since he had a good grade point average and didn’t cause any problems during his freshman year, most of the teachers more or less went along with him.

He also told his classmates to call him Sam and use masculine pronouns.

In the fall of that year, Sam continued to publicly transition and began to see a therapist. The therapist subjected him to a battery of tests and held lengthy interviews. The therapist diagnosed him with Gender Dysphoria. The therapist explained it in technical jargon as ‘a marked
incongruence between one’s experienced/expressed gender and assigned gender’.”

In January, Sam took part in an orchestra performance, wearing a tuxedo. His orchestra teacher, classmates, and the audience accepted this without incident.

Wearing a tuxedo is one thing, using the boys’ restroom is another. Sam and his mother met with Nancy Groton, Sam’s guidance counselor at school. “I’d like Sam to be permitted to use the boys’ restrooms while at school and at school-sponsored events,” his mother said.

“I see,” Ms. Groton said, but it was clear that she didn’t. “I’ll have to take this up with the principal, and let you know,” she added. There was no immediate decision made, and Sam and his Mother had several additional meetings with Nancy Groton, at which the request was repeated.

“It’s a simple request, and we are entitled to an answer,” Sam’s mother said.

“No, it’s not that simple,” Ms. Groton said. “You see, Sarah ... I mean Sam, is registered as a female.”

“But look at him,” Sam’s Mother asserted. “Does he look like a girl?”

“How Sam or Sarah appears to me is not the point.”

“Then what is the point?” Sam asked.

“The point is what the principal and administration decide.” Ms. Groton responded.

Then came the decision. “The administration has decided that you can only use the girls’ restrooms or a gender-neutral restroom in the school’s main office,” Nancy Groton told Sam and his mother at the final meeting.

“But the restroom is quite a distance from all of my classrooms,” Sam complained.

“I’m sorry, but that is what the administration decided,” Nancy Groton responded in a tone of voice which indicated that she was not sorry at all.

“But I’ve already publicly transitioned, and using the girls’ restrooms will undermine my transition.” Sam complained.

Ms. Groton said nothing in reply. “Will I be the only student permitted to use that washroom?” Sam asked.

“Yes.”

Sam paused a moment, and then added, “using it will draw further adverse attention
to my transition and status as a transgender student.”

On the way home from the meeting with the guidance counselor, Sam confided, “I’m worried that I might be disciplined if I try to use the boys’ restrooms. That discipline might hurt my chances of getting into college.”

“I understand,” his mother said

“Maybe if I drink less water, I can avoid using any restroom at school for the rest of
the school year,” he concluded.

***

Shortly after that, Sam related his decision to his Physician. “If I don’t drink a lot of water, I won’t have to pee as much, and won’t have to use any washroom.”

“I can’t recommend that,” his Physician responded. “Your body needs a certain amount of water to function properly. Your decision could have serious consequences.”

“Like what?” Sam’s Mother asked.

“Sam has been diagnosed with vasovagal syncope,” the Physician said, “This condition rendered Sam more susceptible to fainting and/or seizures if dehydrated. To avoid triggering the condition, I advise him to drink six to seven bottles of water and a bottle of Gatorade daily.”

“I don’t know whether I want to do what the Doctor advised,” Sam later confided to his Mother, “I hate having to use that washroom.”

Accordingly, Sam decided to restrict his water intake to ensure that he did not have to utilize the restroom at school, and he indeed suffered from symptoms of his vasovagal syncope, including fainting and dizziness. He also suffered from stress related migraines, depression, and anxiety because of the policy’s impact on his transition and what he perceived to be the impossible choice between living as a boy or using the restroom.

After being sent home following a fainting attack, he told his Mother, “I wish I was never born. In fact I wish I were dead.”

“Honey, you’re not thinking of killing yourself?” his Mother asked anxiously.

“I am,” Sam replied.

* * *

The next September, Sam started his junior year, and only used the boy’s washroom. For six months he did this without incident.

Then it happened. A teacher saw Sam in the boy’s restroom and reported it to the Principal. The Principal called Sam’s Guidance Counselor, Ms. Groton, and explained the matter to her. “I want you to put a stop to this. Talk to this student and advise her of the adverse consequences of her behavior.” Suitably briefed, Ms. Groton had Sam summoned from his class.

What followed was not pleasant, at least for Sam. He was seated in a hard chair in the reception area for his Guidance Counselor, Ms. Groton.

“I’m really disappointed with you,” Ms. Groton said in the way of a greeting. “You’ve been told many times that you may not use the boys’ restroom. Why do you insist on disobeying this rule?” The session went downhill from then. Finally Ms. Groton told Sam, “If you want to change this, you have to speak with the Principal.”

Sam reported the substance of this incident with his Mother, who requested a meeting with the Principal. On the appointed day Sam and his Mother appeared at the Principal’s office for a meeting with the Assistant Principal, Ms. Stephanie Stevens, to discuss the school’s policy. Like before, Ms. Stevens stated that Sam was not permitted to use the boys’ restrooms.

“I don’t see why,” Sam’s Mother stated.

“Your child is listed as a female in the school’s official records,” Ms. Stevens said, “and to change those records you need legal or medical documentation.”

“Like what?” Sam’s Mother retorted.

Ms. Stevens did not know, but she didn’t want to admit it. “Documentation that Sam is really a boy.”

“I’ve given you his Physicians’ and counselor’s reports, aren’t they enough?

Apparently they weren’t enough, because the school records were not changed.

Then Sam’s Mother submitted two letters from Sam’s Pediatrician, identifying him as a transgendered boy and recommending that he be allowed to use male-designated facilities at school. These were reviewed and deemed not sufficient to change Sam’s designation.

In response, the school changed it’s story. At a subsequent meeting with the administration Sam and his Mother were told that the school maintained that Sam would have to complete a surgical
transition. Sam’s Mother went ballistic. “That is pure nonsense,” she said, “that procedure is prohibited for someone under the age of 18!”

She also said, “Further, not all transgender persons opt to complete a surgical transition, preferring to forgo the significant risks and costs that accompany such procedures. You have never given me a written statement of your policy and how a person can change his or her status.”

The School did not give any explanation as to why a surgical transition was necessary. Indeed, the verbal statements made to Sam’s mom about the policy were never reduced to writing. As it later appeared, the School never provided any written document that detailed when the policy went into effect, what the policy is, or how one can change his status under the policy.

Fearing that using the one gender-neutral restroom would single him out and subject him to scrutiny from his classmates and knowing that using the girls’ restroom would be in contradiction to his transition, Sam continued to use the boys’ restroom for the remainder of his junior year.

* * *

Meanwhile, at the Principal’s office: The Principal sat at his desk. All of the school’s security guards stood in front of the desk.

“We have a problem here,” the Principal began, “we have a girl using the boy’s restroom, against what we have told her is not permitted. The student’s name is Sarah Daniels, but she goes by the names of Sam or Samuel Daniels.”

The Principal picked up some photographs from his desk. “Here are photographs of Daniels.” You are instructed to monitor this student’s use of the boys’ restroom, and report the same to me.
I will have the student brought in to me when it happens.”

Some people watch too many action and espionage movies, and a certain school security guard was one of them. He had romanticized his job as one requiring stealth and immediate action to enforce the school’s rules. Therefore, this school security guard stood in a darkened recessed doorway off the hall, waiting to nab his quarry which he only knew as a student named Sarah. He was dressed in his uniform shirt and black cotton twill BDU pants, the cuffs of which were neatly tucked in his uniform boots. Only his right hand was visible, and in that hand he held a small mirror by which means he could view the entire hallway. He had studied the photograph and felt that he could identify ‘Sarah.’ He had conducted subtle reconnaissance a short time before and knew that his quarry was in room 214. Only a boy’s lavatory stood between his darkened doorway and room 214.

He stood there waiting, until suddenly a loud bell sounded and the occupants of room 214 flooded into the hall. In his mirror he recognized his quarry, who moved down the hall toward him, only in the last minute to dart into the boys’ lavatory accompanied by other former occupants of room 214. There was no indication that his quarry was aware of his presence.

“Now I’ve got you, red handed,” he said to himself, and not wishing to waste a moment, he rushed into the lavatory. He spotted his quarry who was dressed in khaki pants and a long sleeved cottons shirt, almost identical to the attire of the other occupants. He quickly moved up to his quarry and loudly announced. “Hold it right there, miss, you’re not allowed in a boy’s washroom. You’ll have to come with me,” and he pointed to the door. Sam, his quarry, muttered a dark oath, and headed for the door with the guard.

Sam’s next class was English, where the class was studying Shakespear’s ‘Twelfth Night’ which ironically is a play where a girl disguises herself as a man. A messenger from the Principal’s office interrupted the class and handed the teacher a note.

“Daniels, you are to report to the Principal’s office,” the Teacher said. With that, Sam accompanied the messenger to the Principal’s office.

“Miss Daniels,” the Principal started, with emphasis on the word ‘Miss,’ “Why do you insist on violating school policy by using the boy’s restroom?”

“Could I see a copy of that policy?” Sam responded.

“Er ...” the Principal said, “It’s unwritten, but you know well what that policy is. It has been explained to you multiple times.”

“With multiple variations,” Sam responded, “so I’m not exactly sure what that policy is.”

The discussion went downhill from there, only to be repeated on future occasions.

Sam fended off questions from other students as to why he was called to the Principal’s office, but it was embarrassing.

* * *

Sam and his Mother had enough, and in April they consulted an attorney, who sent the School District a letter demanding that it permit Sam use the boys’ restroom while at school and during
school-sponsored events. In response, the School District repeated its policy that Sam was required to use either the girls’ restroom or the gender-neutral facilities.

The school didn’t appear to want to change its position.

Sam met with his attorneys. “We suggest that you file an administrative complaint with the United States Department of Education’s Office for Civil Rights, alleging that the school’s policy violated your rights under Title IX.”

The attorneys also suggested that Sam file a federal case seeking to enjoin the school’s restroom policy.

“If we want to pursue the case in federal court, we will have to dismiss the administrative complaint. We can do this ‘without prejudice’ which means that we can reinstate it if we have to.”

Sam filed suit, seeking a preliminary injunction against the school. The preliminary injunction sought to prevent the school from continuing its washroom policy.

While all of this was going on, Sam started hormone replacement therapy and a month later legally changed his name to Samuel Daniels.

It was not long thereafter that the district court entered a preliminary injunction prohibiting the school district from: (1) denying Sam’s access to the boys’ restroom; (2) enforcing any written or unwritten policy against Sam that would prevent him from using the boys’ restroom while on school property or attending school-sponsored events; (3) disciplining Sam for using the boys’ restroom while on school property or attending school-sponsored events; and (4) monitoring or surveilling Sam’s restroom use in any way.

It is not surprising that the school filed an appeal. The Court of Appeals affirmed the district court’s granting of a preliminary injunction.

At long last, Sam was allowed to use the boys’ room


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