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
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
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
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