The Babysitter
By Pentatonic

“Young lady, you aren’t allowed in the pool without something on top,” commanded the life guard at our community pool. I looked around to see to whom he was talking. “You, yes you,” he added, pointing at me.

“But I’m a boy, not a girl, so I don’t have to wear a top,” I complained.

“Are you sure? Isn’t your name Emily?” he asked.

“No, she’s my sister. We sorta look alike,” I answered.

My name is Chris, and the truth of the matter is that Emily and I look a lot alike. Both of us have shoulder length honey blond hair, which our Mother makes us brush every day. She says it makes our hair “glow.” Both of us are petite and about the same size. We both have pretty faces, except I’m prettier and Emily’s breasts have started to grow. This was certainly not the first time I had been mistaken for a girl. Ever since I was little, Mother liked to emphasize that Emily and I looked like twins.

My pals, Tom and Joe, thought the exchange with the lifeguard to be hilarious, and they referred to me as “miss” and “young lady” the rest of the afternoon. When I returned home, my Mother looked at me and said, “Go take a shower and get the chlorine out of your hair. Make sure you use a conditioner and brush it out when it is dry. By the way, did you have a good time at the pool?”

“The stupid lifeguard thought I was a girl, and wanted me to wear something on top. He thought I was Emily,” I answered.

When Emily heard her name, she joined in the conversation. “I have a nice tankini top you could borrow,” she suggested with a snicker, “or maybe you’d like a string bikini?” I just scowled at her in response.

“I only say that because when you were younger, you liked to dress up in my clothes,” she replied.

“Maybe so,” I admitted, “but those days are long gone.” I had to admit, only to myself, that I had enjoyed and missed those times. However, that was then and now is now, and I had grown tired of being mistaken for a girl.

“I’ve wondered what you’d look like with a little makeup and in a dress,” my Mother mused.

“That’s a great idea,” my Emily chimed in.

“I don’t think so,” I rejoined.

“Oh, come on,” Mother asserted, “it’s only once, and only for a little while.”

Emily came over to me, and cupped my chin while she examined my face. “A little mascara, some eyebrow pencil, and lip color would do the trick.”

I myself wondered how I would look. “I guess so, but only once, and no one else can know,” I reluctantly said.

“Stay right here, don’t move a muscle. I’ll be right back with some clothes and makeup,” Emily commanded. She returned a few minutes later with an armful of her clothes and a shoebox full of makeup.

“Strip!” she commanded.

“But,” I asserted.

“No buts,” Emily rejoined with a chuckle, “it’s not like we haven’t see all of you before.”

She was correct, so I took off all of my clothes. Emily handed me a pair of pink panties, which I put on. “Put on this camisole and slip,” she said as she handed them to me. She then slid a dress over my head. Since we were the same size, if fit me perfectly.

Emily then commanded that I sit, and she commenced with the makeup. Mother just sat there, enjoying the proceedings with a smile.

“Consider yourself lucky that I’m not going to trim your eyebrows, although I should. I’m just going to defined them a bit with the eyebrow pencil,” Emily declared. This was followed by an application of mascara and lip color.

“How about some blush on her, I mean his, cheeks? Mother suggested.

“Great idea,” Emily answered, and she immediately added the blush.

“Stand up, and turn around,” Mother commanded, “so I can see it all.”

“Are you two quite finished?” I said, “because I want to get back in my clothes.”

“No, I want to enjoy this for a few minutes more,” Mother answered. “It reminds me of the times years ago, when you and Emily dressed like twins,” she reminisced.

“Can I sit down, now?” and I began to sit.

“NO! Not like that,” Mother injected. “That’s not how a refined young lady sits.” I just looked at her questioningly. “You don’t just plop into a chair, You smooth your skirt under you, and sit on the front of the chair, with your hack straight.”

“But I’m not a young lady.” I asserted.

“Looking like you do now, you are,” Mother said. I just let out a sigh and did as I was told.

“Are you happy now?” I asked. “Can I get rid of this makeup and put my own clothes back on?”

“After we get a few pictures of you with your sister,” Mother added.

“NO WAY!” I shouted. I had no idea where those pictures would end up and I certainly didn’t want to find out. My complaint went unheeded, and I, sometimes by myself and sometimes with Emily, had to pose for pictures. I could see Emily trying to figure out how to get copies of those pictures for her own evil purposes.

At last I was free to change back into myself. Before changing, I paused at a full length mirror in the hallway, and examined my transformation. I did make a good looking girl, even prettier than Emily, I commented to myself.

It was then that I decided that the shoulder length hair had to go, if I were ever to stop being mistaken for a girl.

That evening at dinner, I announced that I needed a haircut.

“Why?” Mother asked, “your hair is great looking just as it is. It’s just like Emily’s,” she added.

“That’s the point,” I responded, “I don’t want to be mistaken for Emily.” I recounted the incident at the pool to my Father. “I don’t want Emily’s admirers hitting on me.”

“Well,” Mother finally relented. “I have an appointment at the beauty shop the day after tomorrow. I’ll call then up and see if they can fit you in.”

“How about a regular men’s barber?” I interjected. I was thinking about a buzz cut.

“If you want me to pay for it, it’ll be at my salon,” Mother said. “If you want to go to a barber shop, you can pay for it yourself, and walk there, because I’m not giving you a ride to a barber shop.” She had me there. She knew that I had no money of my own, since I had asked for some cash earlier that day.

My Dad just observed this exchange with a bemused smile on his face. He well knew that Mother usually got what she wanted.

The problem with Mother’s salon was that she could exercise a lot of control over what was done to my hair. I would end up with what she wanted, not what I wanted.

On the morning of the salon appointment, I sat down for breakfast wearing my usual summer grunge clothes. This was met with stern disapproval by Mother, not only for what I was wearing, but also by the way I just plopped down into my chair. “You’re not going anywhere with me dressed like that,” she said, “and sit down gracefully.”

After breakfast Mother marched me to my room to find “suitable clothes.” Suitable clothes meant a pair of tan shorts and a light blue t-shirt. “You have to brush out your hair before we go,” she said.

“Why?” I asked, “they’re just going to cut it.”

“Just do it,” she responded in a tone of voice which invited no argument. So I sat down and gave my hair a hundred strokes. When done, I studied my reflection in the mirror. My hair looked great, for a girl. Finally I passed inspection and Mother and I got into her car.

When at the salon, Mother continued to control the entire situation. “What can we do for you today, miss?” the beautician asked. I hoped that mistaking me for a girl would end with a haircut. “She’d look great with some highlights.” the beautician suggested to my Mother.

“No,” I answered. “I want a buzz cut.”

“Not with such beautiful hair,” the beautician exclaimed. “Why would you want to do that?”

“Because I’m a boy, and I want people to stop thinking that I’m a girl,” I answered.

“A buzz cut won’t stop that,” the beautician said. “You have such a pretty face,” she added. “If you get a buzz cut you won’t look like a boy, you’ll look like a girl with a buzz cut.”

“There are a lot of girls with buzz cuts,” my Mother injected, “so a buzz cut won’t solve your problem.”

The beautician said that she could give me a “boyish” cut, which turned out to be a lot like a pixie cut. I wasn’t happy with the final result, but there wasn’t much I could do about it.

Emily was at the door when Mother and I returned home. “Let me see,” she said. “Tinkerbell!” she exclaimed with great glee. “You still look like a girl!”

I retreated to the bathroom \to see what I could do with the disaster on my head. After fiddling around I was able to get rid of the Tinkerbell look, but I was only partially successful in getting to look like a boy.

In addition to Emily, I have a three year old sister named Ann. After lunch, Mother suggested that I take Ann in the stroller to the park, “for some fresh air.” Ann loved the park. As usual, after installing Ann in the stroller, I also packed some of her favorite books, and some goodies to eat. The park is only a few blocks from the house, and when we arrived there I found a shady place to spend some time. I let Ann climb up on the park bench next to me, and I pulled out her favorite books. “Which one do you want to start with?” I asked her. After she made her pick, we sat side by side, and I read and showed her the pictures.

After about an hour a woman came down the path with two girls who appeared to be about four or five. When I looked up, she smiled at me and said, “You two make such a pretty picture, Do you mind if we join you?” Her girls climbed up on the park bench, and one of them asked, “Can we listen to you read?”

“Sure,” I said, and I continued to read, but now I had to pass the book around so all of the girls could see the pictures.

After some time amusing all three girls, the woman turned to me and said, “I’m Mrs. Benson and these are my daughters, Amy and Susan.”

“I’m Christopher Parker, and this is my sister Ann,” I said in the way of an introduction.

“Christopher?” she said questioningly, thankfully not saying that she thought that I was a girl. So much for the haircut.

“Yes,” I responded. “Ann loves it when I read to her. My older sister Emily never reads to her.”

“The two of you make such a pretty picture, I just had to stop and say so,” Mrs. Benson added. “Do you babysit for your sister?” she asked.

“Yes, I have since Ann was born. Like I said my older sister always seems to have other things to do. I don’t mind it, and it brings Ann and me closer.”

“Do you babysit for any other children?” she asked.

“Not really, I just turned fourteen,” I explained.

“Are you interested in babysitting?” she asked.

“I never really thought about it, but I guess I could. However there doesn’t seem to be much a market for boy babysitters,” I said.

“Boy?” she questioned. “My girls seem quite taken to you,” she added, “I don’t think that your being a boy would be a problem. Would you mind if I called you?” I gave he my phone number and we parted, and I went back home.

I recounted the events at the park to my Mother. “Is it all right if I took a babysitting job with Mrs. Benson?” I asked her.

“If she doesn’t mind you being a boy, I don’t see any problem,” Mother answered.

So began my career as a babysitter. I really liked the Benson children, and Mrs. Benson told me that the children liked me because I paid attention to them and read and played games with them. A big plus was that I got paid and now had my own money, which frosted my sister.

It was several months later that a problem arose. I was scheduled to babysit for the Bensons. On the Monday before, Mrs. Benson called Mother, and Mother told me about the situation. It appears that the Bensons had a dinner arranged with their friends, the Carlsons. The Carlsons had one child, and their babysitter had cancelled. The Carlsons had suggested that maybe they could bring their six year old daughter to the Benson’s house, and I could sit all three. This was hardly a problem. The problem was that the Carlsons did not like boy babysitters.

“Mrs. Benson wondered if you would mind dressing up as a girl for the babysitting job,” Mother related. “I don’t have a problem with it, but it’s up to you.”

Inwardly I was excited. I hadn’t lost my desire to dress as a girl; I just wanted it to be on my own terms, and not to be mistaken to be a girl unless I intended it to be so.

“I don’t know if I could pull it off.” I said.

“I think you could,” she said. “Why don’t we ask Emily.”

“I’d rather not,” I answered.

“I think you have to, because you will be borrowing her clothes,” she said. So Emily was invited, much to her glee, to join in this endeavor.

“Chris will have to part with some of his, or her, cash and buy her own makeup,” my sister declared, “It isn’t a good idea to share makeup.”

“How about clothes?” Mother asked.

“I don’t want to share underwear,” Emily answered.

“Okay,” Mother said, “we’ll make a trip to the mall tomorrow after supper.”

So the next day, after supper, Mother, Emily and I went to the mall. The first stop was at the lingerie section at the department store, where I purchased two pairs of pink lace trimmed panties and nude pantyhose. The two pairs of panties were to help me “tuck.” I drew the line at buying a training bra, however, much to Emily’s disappointment.

“If she isn’t going to get a bra, she needs a camisole,” Emily insisted, so I bought a camisole.

Next we stopped to buy some cosmetics. “I’d like some starter makeup for my daughter,” Mother told the clerk, “she’s only 14, so it should be minimal. Maybe eyebrows, mascara, blush and lipstick,” Mother added. The clerk applied the suggested makeup. When completed to Mother’s approval, she told the clerk, “We’ll take whatever you used, and maybe some perfume.”

“Maybe a pair of shoes?” Emily then suggested. So we went to the discount shoe store and purchased a pair of flats.

On our way out, we passed an earing kiosk. “Let’s have her ears pierced,” Emily suggested. While I did not like the idea, Mother did, and I ended up with two gold studs in my earlobes. I successfully resisted purchasing more earrings, mainly because I was paying for everything that was purchased.

When we arrived back home, Mother told me to go to my room and put on the panties, pantyhose and camisole, while she and Emily looked for clothes. “Do you want a dress or a skirt?” Emily asked with a chuckle. Emily was enjoying this far too much, I thought. “Neither!” I replied. “How about just a pair of slacks?”

Mother and Emily selected several slacks, and I ended up with a pair of dark brown ones with a zipper up the left side. They selected a tan sleeveless blouse with ruffles up the front, to hide, as Emily put it, “your lack of boobage.”

“You need to practice putting on your makeup,” Mother declared, so I sat at Emily’s vanity, and I learned how to apply makeup. “Remember, you will have to refresh your lipstick during the evening,” Mother advised.

When my makeup met Mother’s approval, I finally got a chance to look at the finished result. I was impressed. I really looked like a teenaged girl. “We’ll do something with your hair on Saturday,” Mother declared.

Mr. Benson picked me up for the babysitting job. “Wow,” he said when he first saw me, all dressed, with makeup and my pixie hairstyle. “When I heard what my wife suggested, I never thought it would be this good.”

When the Benson’s daughters saw me, all they did was to say how beautiful I was. There was nothing about the fact that I had not dressed as a girl before this time. Likewise, when the Carlsons arrived, their daughter just took me at face value, and didn’t question my gender.

Just before they left, Mrs. Benson pulled me aside for some last minute instructions. “You really look fabulous tonight,” she said. “I’m really impressed. Are you sure you’re not really a girl?” she said with a laugh.

The evening went smoothly. We played some simple board games, watched some television, had snacks, and I read to them. It was readily apparent that the Carlsons never read to their daughter. When the Bensons and the Carlsons returned, I was doubly delighted, not only did the Bensons pay me, which was all I expected, but the Carlsons also insisted on paying me. I also got a nice tip from both. The second delight was when the Carlson’s daughter asked if I could be her babysitter in the future. I agreed, even if it would require buying more girl clothes.

Based upon recommendations from the Bensons and the Carlsons, I began sitting every weekend when I was not sitting for my little sister. Of course for my sitting jobs, I dressed as a girl, which I was really beginning to like doing.

Along the way I acquired a lot of girls’ slacks and blouses and yes, I did buy some training bras with Emily’s gleeful help. Then came the time when the Carlsons were going to dinner and a show with their daughter, and they invited me to come along, since their daughter behaved better when I was there. This invitation meant that I would have to wear a dress. Again, Emily offered her help, with glee.

Mother, Emily and I went to the mall to find a dress. I was wearing panties, panty hose, flats, a camisole and a nice blouse and slacks. We found a light blue dress with cap sleeves, a tight bodice and a pleated full skirt, to hid any bulge. We stopped at a store that sold costume jewelry, and I bought a fake pearl necklace and bracelet.

I was pleased that the Carlsons liked the way I was dressed. Their daughter held close to me the entire evening, and I made it a point to talk to her without being condescending which pleased her and her parents. “Our daughter looks to you like an older sister,” Mrs. Carlson said during a washroom break. “You are going to make a really good mother,” she added. I smiled back at her and thanked her.

With my babysitting jobs, I was a girl every weekend night. I really liked this, and later, even though I was not at a babysitting job, I began to dress as a girl after school on week nights.

“Are you sure that you’re not a girl?” my Mother asked me one Wednesday evening when I was fully dressed.

“I’m not sure,” I replied. “I do like being a girl.”

Several months thereafter, Mother asked me the same question. “I’d really like to be a girl,” was my answer this time, and with my parents’ help, I started on the long process to meet that goal.

The Babysitter - Part 2
By Pentatonic

Author’s Note: This is a continuation of The Babysitter. All of the people who commented wanted me to continue the story. This part starts where The Babysitter ended, so you might want to read that first.

During the summer it came to my attention that the shorts being worn by basketball players seemed a lot longer than they had previously been. In fact they came down to just above the knee, sort of the same length as the kind of skirts I liked. Not only that, they were made of a shiny fabric. I just had to have a pair. With my babysitting money in my pocket, I hopped on my bicycle, and headed to the local discount store. To my delight, they weren’t all that expensive and I bought a pair in black polyester. To my further delight, I found that the mens’ version had two pockets.

The weather the next day was one of those delightful mid August days. I put on my new shorts and a light blue t-shirt and rode my bicycle to Tom’s house. Tom’s mother met me at the door. “Come on in, Chris, they’re in the den,” she said, as she followed me into that room. Tom and Joe were sprawled on the furniture, watching something on the television. A grunt from Tom was my sole greeting. I looked for somewhere to sit, and saw a straight backed chair. I walked over to the chair, and instinctively smoothed out the shorts as if they were a skirt before sitting on the front edge of the chair, my back straight, my knees together, and my legs crossed at the ankles, exactly as my Mother had instructed me to do. This was not lost on Tom’s mother, who was closely watching me. I saw her stare, and gave her a small smile. She smiled in return, but it looked like there was a question in the smile, like why did I sit like that?

No one said anything for a minute, then I said, “I was thinking of taking a bike ride to the Purple Horse and getting some ice cream.” Neither Tom nor Joe even looked at me, but this time it was Joe who grunted. The Purple Horse is an ice cream parlor on the other side of town, known for its ice cream.

“I donno,” rejoined Joe. “Whose paying? I can’t, I don’t have any money.”

“I’ll treat,” I answered, “I babysat last night, so I have cash.”

“That sounds like a great idea,” Tom’s mother said, “but you don’t have to treat, I’ll give Tom some money.” She turned to Tom and Joe, and said, “Get off your lazy butts and go out for some fresh air with Chris.” Tom and Joe stood up and slouched to the door. I followed with my back straight up, taking measured steps like I would as if I was wearing a skirt.

Before we got to the front door, Tom’s mother pulled me aside. “You look somehow different,” she said in a low voice. “Not bad, just different.” If she was looking for an explanation from me, she wasn’t getting one. I just smiled at her, and followed Tom and Joe out to our bicycles.

There were some boys at the Purple Horse when we arrived. They gave Tom and Joe cursory glances. However, they obviously were checking me out. Joe came close to me and whispered, “They think you’re a girl and they want to hit on you.” I just frowned at him in return.

This didn’t deter Joe. “Heck, if I didn’t know, I’d want to hit on you. You really look foxy right now.” I just jabbed my elbow into his side to show my displeasure, even thought I was inwardly pleased that the boys thought I was a girl and that Joe thought I was “foxy.” Thankfully the boys got their ice cream and left with no further incidents.

When I got back home, Mother asked me about the ride to the Purple Horse. I related that some boys were checking me out and that Joe thought that I was foxy. At this point Emily joined into the conversation. “Foxy?” she questioned. “Now if you had some mascara and lip gloss on, then you would look foxy.”

“Who asked you?” I rejoined. “This is none of your business.” Emily just laughed. But she is right, I thought to myself.

***

Even though my hair was short, Mother still insisted that I brush it a hundred times each evening. One evening when I was doing this, Mother commented that my pixie cut was getting a bit shaggy. “I’ll make an appointment for you for the next time I go.”

When I got up on the morning of the appointment, Mother said, “Wear some of the clothes you wear when babysitting.” This meant dressing like a girl. “Maybe a little mascara and lip gloss would also be in order.” I smiled at her, inwardly happy to be a girl for the morning.

When we arrived at the salon, the beautician asked me what I wanted. “A trim. It’s getting a little long,” I answered.

“How about some highlights?” she asked.

“Not today,” I answered. I would have loved to have highlights, but I didn’t think it would go over well when school started in the fall.

***

On the afternoon after my salon appointment, I was hanging out with Tom and Joe. Although I had removed all traces of makeup, my hair style seemed to pique their attention, and they were curious. “Isn’t babysitting a chick job?” Tom asked.

“Maybe most babysitters are girls, but there is no rule,” I replied. “The people I sit for don’t seem to mind that I’m a boy,” I added, intentionally failing to mention that the Carlsons thought that I was a girl.

“So what do you do when you babysit?” Joe asked.

“Pretty much what your babysitters did when you had a babysitter,” I said, but then I added, “I also read to the children, play games, and otherwise entertain them.”

“Does that mean you play dolls with them?” Joe said with a smirk.

“On occasion I have to do things that five to seven year old girls like to do,” I answered.

“Sounds kinda girly to me,” Joe rejoined.

“Maybe it is, but at the end of the evening I have cash in my pocket. That’s more than you can say after playing computer games all evening,” I added. Actually, I liked the girly part, because I had recently wondered whether I wanted to be a girl. Doing girly things gave me something that I had missed when I was being brought up as a boy.

***

My babysitting for the Bensons and the Carlsons continued, and from their recommendations, I gained some additional clients, one of whom was Mrs. Sloan. Mrs. Sloan was a single mother with a six year old daughter, Ellen. I had recently discovered that the “Wizard of Oz” was part of a series of Oz books, and I was able to take one of the other books out from the library. Therefore, I took the Oz book with me to read to Ellen.

Because it was the first time I sat for Ellen, I paid special attention to how I was dressed. I had a relatively new pair of black capri pants and a white blouse with cap sleeves. I did not tuck the blouse in the pants, because it helped hide the fact that my hips were somewhat small. I brushed out my hair. My chest was totally flat, which was not a real problem since a lot of girls my age had nothing on top. I did decide to help things along and I wore a training bra. Mother agreed with me that makeup was not necessary.

Mrs. Sloan had, as she described it, a hot date, and needed time to prepare, so my Dad drove me to the Sloan house. As soon as I arrived, it was clear that Ellen didn’t like being left with a babysitter. “She’s always like this when I go out on a date,” Mrs. Sloan said, as if this explained everything, which it didn’t. It wasn’t until I started reading to her that Ellen calmed down.

“No one ever read to me before,” she said as she snuggled up to me.

“Do you like this story?” I asked. She nodded her head in affirmation.

About an hour and a half later the front door flew open with a bang, and there stood Mrs. Sloan with a very angry look on her face. “The bastard!” she exclaimed, “He’s married! No more dates with him,” she fumed. Perhaps because her daughter and I were present, she gave no further details. “Just keep on doing what you’re doing and ignore me,” she said as she plopped down into a chair.

Ellen and I just looked at each other. “I don’t like it when Mommy’s mad,” she said softly.

“Do you want me to keep reading, or should I go home?” I asked Ellen.

“Please keep reading,” she replied, and so I did. All this time Mrs. Sloan looked at the two of us, and slowly her face relaxed as she began to take in the story. I was almost afraid to stop, not knowing what would happen if I did. However, after another hour, my voice was tired and we were at the end of a chapter.

“I think it’s time for bed,” I told Ellen, and she nodded her head. “Do you want me to put her to bed?” I asked Mrs. Sloan.

“If you wouldn’t mind,” Mrs. Sloan answered, “I’m still angry about that bastard.”

“Will you read to me some more?” Ellen asked.

“If your mother wants me to sit for you again,” I said, “sure.”

After getting Ellen in bed, I sang a short lullaby to her. It seemed to please her. When I came back downstairs, Mrs. Sloan was still sitting in the same chair, but now she had a glass with amber liquid in her hand. I assumed, correctly, that it was a stiff drink.

“I’m sorry that I blew up and made a scene,” she said.

“That’s okay, I think I understand,” I replied.

“I’m not sure you do, since you are only fourteen,” she said, “you aren’t dating boys yet, are you?”

“No,” I said.

“I want to say that you handled yourself very well. I can tell that Ellen is quite taken with you. Reading to her was brilliant. No other sitters ever did that.”

“I read to my baby sister, and to all of the kids when I babysit,” I explained. “I, and they, enjoy it. It seems to calm them.”

“You are a very interesting girl,” she said, “sit down next to me and tell me about yourself,”

I sat down as gracefully as I could, and started to talk. “There isn’t much to tell. I’m fourteen, and have a younger sister, Ann, and an older sister, Emily. I’m starting high school shortly, and I enjoy reading. I sit for Ann, and recently I’ve started sitting for other people. That’s about it,” I said.

“Do you like babysitting?” she asked.

“I do. I like children, and I like the money I earn. Emily doesn’t like to sit, and it frosts her that I am earning money and she isn’t.

“Well, you’ve had a full day, and I imagine that you want to return home,” she said, and reached into her purse and handed me some money. A lot of money, more than I expected.

“This is a lot more than I charge,” I said.

“Maybe, but you’re worth every penny.”

I called my Dad to pick me up, and we both stood up. Unexpectedly, she reached over to me and gave me a hug. I hugged her back, and she put a finger to my face, and looked into my eyes. She moved her face close to mine and gave me a kiss on my lips.

“Oh, if only you were older,” she said. I couldn’t quite understand what that meant, but let it go without comment.

***

A week before Labor Day Mrs. Benson called me. That she called was hardly unusual, since this is the first step in a babysitting job. However, what she proposed was different. Her church holds a Labor Day picnic every year, and she had related that when I sit I often read to the children. Some of the Elders thought that having a “Story Lady” at the picnic might be entertaining for some of the children, and Mrs. Benson wanted to know if I was interested in volunteering to be the Story Lady. Volunteering, as opposed to being paid.

The Bensons had been very kind to me over the summer, and volunteering would be a way to show how much I appreciated their kindness. Okay, I didn’t mind the no pay part, but there was a much larger problem. I was starting high school, and I was registered as Christopher, a boy. A boy with a pixie haircut. I could deal with that by manipulations to my hair style, as long as there could be no other connection with me as a female. If I showed up at the picnic as the Story Lady, even the most dense of the neanderthals at the school could connect Chris, the boy with the funny haircut with Chris, the girl in a full skirt with a pixie haircut who was the Story Lady at the picnic. Since Mrs. Benson knew that I was a boy who dressed as a girl for my babysitting jobs, I felt that I could tell her that I was concerned that someone might connect Christopher the high school student with Christine the story lady. “I see what the problem is and I understand your concerns. Maybe it is best to drop the whole idea.” I felt badly about this, but neither Mrs. Benson nor I could see a solution.

Then it came to me. “I could be the ‘Story Teller’ and dress androgynously, pretty much as I would when I went to school.” The Elders approved of the change and everything was set.

My exposure came not from any of the students at my highschool, but from an unexpected place, namely Tom’s mother. Tom and his parents attended the same church as the Bensons, and as it turned out, the Carlsons. Tom’s mother was standing next to the Carlsons, watching me read, and Mrs. Carlson turned to Tom’s mother and said, “She’s babysat for us, and she does a wonderful job reading and entertaining the children.” Tom’s mother caught the use of the feminine pronoun. This brought to her mind the time at Tom’s house when she caught me sitting down in a refined feminine manner. Thankfully she said nothing to Mrs. Carlson.

Later that day, after my time as the story teller was finished, she came up to me and asked if I had a few minutes.

“Sure,” I said, “what’s up?”

“Should I call you Christopher, or maybe Christine?”

I was thunderstruck and made no response. “I was talking with Mrs. Carlson, and she thinks you are a girl,” she said, “I’ve known you for years, and I know that you are a boy, so why does Mrs. Carlson think you are a girl?”

I explained as best as I could that the Carlson only wanted a female babysitter, so I pretended to be a girl.

“That’s not all there is to it, is there?” she questioned. Without waiting for an answer, she said, “I’ve noted that you are acting a lot like a girl recently. You move, you sit, you stand and you walk like a girl. Why?”

I didn’t answer her.

***

In September Mother recalled something I had said the past summer. She had asked me, “Are you sure that you’re not a girl?”

At that time I answered, “I’m not sure, I do like being a girl.”

Recently Mother asked me the same question. “I’d really like to be a girl,” was my answer this time. After consulting with our family doctor, we were referred to a specialist child and adolescent Gender Identity Clinic because I was only 14.

Mother made an appointment, and on the day of the appointment we left my little sister in the care of my older sister, who recited a litany of complaints for being forced to babysit.

No healthcare can start without paperwork, and this was no exception. After filling out what seemed to be reams of forms and a written gender identity test, we finally met with a psychologist who told us that I needed to have a full physical exam with complete blood work, and to come back in when this was done.

Our second session was more productive. I was surprised when the psychologist told us that the majority of children with suspected gender dysphoria don't have the condition once they reach puberty. Notwithstanding this, she recommended that treatment should be arranged with a multi-disciplinary team. This is a group of different healthcare professionals working together, which may include specialists such as mental health professionals and pediatric endocrinologists.

“Why do you feel that you are a girl in a boy’s body?” she asked. I told her of my experiences and feelings, after which she asked, “Who have you told this to?”

“Well, Mom, of course, and she told Dad. I’ve been babysitting this past summer, and Mr. and Mrs. Benson know. I babysit for their daughters. I think that a friend’s mother is suspicious.

“Have you told any of the other parents of children for whom you sit? When you sit for these children do you dress in girl’s clothes?”

“I haven’t told anyone else, and yes, I dress like a girl when I babysit,” I answered.

“Have you told any of your friends?”

“No, but my friend Joe thinks that I act awfully girly,” I answered.

“You might want to talk to the families for whom you sit and tell them that you are a boy,” she suggested, “if you think that they can keep it confidential. There is the danger that some of the parents or your friends will react badly, so you have to move with caution. I assume that you don’t want the school to know.”

***

I decided that I would talk with the Carlsons and Mrs. Sloan, and maybe Tom’s Mother.

I called Mrs. Carlson and said that there was a problem which I had to discuss with her, and I arranged to meet her later in the week.

My heart was pounding when I rang the Carlson’s doorbell. Mrs. Carlson answered the door with a smile. “Whatever the problem is, we can solve it,” she said, “come on in and we’ll talk.”

After exchanging pleasantries, I got down to the problem. “Mrs. Carlson, I haven’t been truthful with you,” I started to say.

“In what way, honey?” Mrs. Carlson asked.

“Well, when I first sat for you, the Bensons said you only wanted a girl babysitter, so I pretended to be a girl. I didn’t expect to keep sitting for your daughter, so I didn’t see the harm in it, especially since the Bensons knew,” I explained.

“Oh, is that all it is?” she said with a big smile. “I’ve known that you are a boy for quite a while.”

“You did?”

“Yes, the Bensons told me, and I have no problem with your gender,” she answered. “Remember when I told you that you are going to make a really good mother? Well I still believe that. Even if you can’t have your own children, you can adopt.”

The end result would be that we would not tell her daughter, and that I would continue to sit for her.

***

Next on my list of confessions was Mrs. Sloan. For my meeting with her, I decided to wear a dress and some makeup. When she opened the door, she said, “Well look at you! You look fabulous. Come on in and tell me about this problem. It doesn’t mean that you won’t be able to sit any more? I certainly hope not. Have a seat and make yourself comfortable”

“After I tell you, you may not want me to sit for your daughter.” I said.

“Tell me what?”

“I’m not a girl. I’m really a boy wearing a dress,” I blurted out.

After a pause, she said. “. . . And wearing it well. You look delightful and very feminine,”

“You’re not angry with me?” I questioned.

“Hardly. How could anyone be angry with such a delightful creature as you are. Like I said, I only wish you were older.”

“Why?” I asked.

“In the parlance of the street, you are a ‘chick with a dick,’ and I find that attractive. If you were eighteen, I’d have my way with you right now.”

“Why eighteen?”

“Laws. Sex with a minor is a crime.”

“Oh,” I said.

With that she stood up and then sat next to me. I could feel our bodies touching. She moved her finger to my face and I turned my head toward hers. She moved her face to mine and kissed me on my lips. I could feel her tongue touching my lips and I opened them to admit her tongue into my mouth. It was like nothing I had ever experience before. At last she broke off the kiss, but continued to stare into my eyes. “We better stop this before it goes to far,” she finally said. “I hope you enjoyed it as much as I did,” she added.

“I did,” I said softly.

“Good,” she said, “because I want you to continue to sit for my daughter.”

***

Talking with Tom’s Mother was a bit of a problem. I satisfied her curiosity, but it appeared that Tom’s Dad was a complete homophobe, and hated anything other than ‘straight’ sex. Tom’s Mother told me that my secret was secure with her, but then she said, “I don’t ever want you to be alone with my son.”

***

I related my experiences with my counselor, and she thought that things went better than expected. “What happened with Tom’s mother is not unusual. I think that from now on you should keep your distance from Tom.”

She made some notes and then said, “I’d like to talk with you about school and your other friends. I think that you should suppress any indication of your gender identity at school, because of the potential adverse consequences.” I had to agree with her.

While I saw less of Tom outside of school, the same was not true with Joe. Unlike Tom, Joe and I shared a lot of advanced classes, and I was helping him with his homework and preparing for exams. Since I had to explain the material to Joe, my understanding increased to the point that my grades improved greatly.

***

One dreary September afternoon, Joe asked, “Hey dude, can you help me with the algebra assignment?”

“Sure,” I replied. “Where?”

“How about your house?”

“Is that because you want to ogle at my sister?” I asked.

“Well, maybe a bit. But if I can’t ogle at her, I can always ogle at you,” he said with a smirk.

“Knock it off, or I won’t help you with math,” I responded with a scowl.

When we arrived at my house my sister Emily was lounging in a most unladylike manner in front of the television. She looked up as we came into the room. “Hello Joe,” she said, and then she added, “Hello Tinkerbell.”

“Why did she call you Tinkerbell?” Joe asked as we headed for my room.

“She thinks she’s being clever, when in fact she’s only disgusting,” I responded.

“Does she mean Tinkerbell as in Peter Pan?”

“Yeah, when I got my hair cut, she thinks it looks like a pixie cut, and therefore she calls me Tinkerbell.”

Joe looked at me closely. “You know, she’s right, you do look like Tinkerbell.”

“Thanks for nothing,” I responded sarcastically.

While going through the math exercises, I caught Joe staring at me. “What?” I demanded.

“You would make a really good looking girl if you combed your hair in a real pixie, put on a dress, and wore makeup,” he commented in return.

“Will you stop that?” I demanded. “Stop hitting on me. I’m not a girl, I’m a boy. Boys don’t hit on other boys unless . .” I left the sentence unfinished.

This didn’t phase Joe. “If I hit on you hard enough, would you give me a kiss?” he asked.

This threw me for a loop. “If you don’t stop hitting on me, I’m going to hit you with this math book.” I said and held the book up in a threatening manner.

“Okay, Okay,” he said, “I give up.”

“Good, and keep it that way,” I said. I lowered the book and continued to glare at him. Deep inside of me I wanted to kiss him, but I would never admit it to Joe or anyone.

When we were finished studying, I walked Joe to the door. “See you tomorrow,” I said.

“See you tomorrow, Tinkerbell,” he responded.

My sister heard that and began to giggle. “See what you started,” I complained.

The next day at school I sat next to Joe in English class. “Hi, Tink,” he whispered.

“Will you stop that?” I whispered back.

“Only if you kiss me,” was his whispered reply.

“Disgusting!” I said as the bell rang and the class started.

A day later, Joe and I were walking home after school, and we passed a fast food joint. “You got enough money to buy each of us a shake, Tinkerbell?”

“Not if you don’t stop calling me that,” I responded.

“You know how to make me stop.” he replied with a smirk.

“If I buy you a shake, will you stop it for at least a week?

“Okay, buy me a shake, and no Tinkerbell for a week,” he promised, and we went inside and ordered the shakes.

Exactly a week later, Joe and I again were walking home from school. “The week’s up, Tinkerbell,” he announced.

I stopped, and looked at him. “You really mean that you want to kiss me? That’s so . . .” I said, not completing the sentence.

“Not only do I want to kiss you, but I want you to kiss me back. A long lingering kiss with lots of tongue,” he said.

“That’s disgusting,” I said, even though deep inside of me I wanted to do exactly that.

When we arrived at my house, I asked Joe if he wanted a hot chocolate before we started studying. “That sounds great, Tinkerbell,” he replied. My sister caught his answer and started laughing. “See what you started,” I said to him with clenched teeth.

“I didn’t start it, your sister did,” he responded.

“Well, I want both of you to stop it,” I said.

“You know how to make me stop it,” he said.

“Disgusting,” I said. While we were drinking our hot chocolate, I felt his leg rubbing mine under the table. “Stop that,” I hissed.

“Stop what?” he said with a false look of innocense on his face.

“You know,” I hissed.

“Oh that,” he said and he moved his leg away from mine.

When we had finished our hot chocolate, we repaired up to my room to start studying. I turned to look him in the eyes. “If we kiss, do you promise to never call me Tinkerbell again?”

“Never? That’s a long time. How about a year?”

Wait, I thought, what am I getting into? I didn’t like the way the negotiations were going. It was almost like I was agreeing to a kiss, which in fact I was.

“Two years,” I countered.

“Let’s compromise on a year and a half,” he said.

When I nodded my consent, he put his arms around me and I put mine around his neck. Our faces grew nearer to each other and our lips touched. I opened my lips to let his tongue inside, and later I pushed my tongue into his mouth. I was really enjoying this. When we broke off the kiss, the only thing I could say was, “Wow!”

“You kiss like a girl,” Joe said. “How about another one, just for fun?”

“Okay,” I said, and we kissed again. While kissing Joe, I compared his kiss with the kiss Mrs. Sloan had given me. I couldn’t decide which was better; they both were wonderful.

***

It was a Wednesday evening when Mrs. Sloan called to ask me to babysit on Saturday. What was different was that it would be a late night, and Mrs. Sloan suggested that I spend the night at her house. “I’ll have to ask my Mom,” I said, “hold on.”

I relayed her suggestion to my Mom. “It sounds okay to me,” she said.

I picked the phone back up and said, “Mom says it’s okay.”

On Saturday afternoon, I packed an overnight bag with my pajamas, robe, slippers and a change of clothes, along with my makeup and a hairbrush. I included the Oz book and some homework from school.

I knew that Mrs. Sloan liked it when I wore a skirt or dress, so I decided on a dark blue dress with a flared skirt. I wore a training bra to give me something on top. Naturally, I wore a nice pair of panties and a full slip under the dress. The dress was a good choice, because when she saw me, Mrs. Sloan said, “You look gorgeous, as pretty as a picture, but then, you always look delectable.”

Mrs. Sloan picked me up at my house at 5:30, because, as she said, she needed time to get ready for her night out.. “You don’t have to eat first, I’ll have something for you and Ellen for dinner.” Her idea of something to eat was take out Chinese.

“I’ve set you up in the guest bedroom for tonight,” she said, and then added, “By the way, I left a present for you to wear on the bed. I hope you’ll like it.”

The present she had laid out on the bed consisted of a white satin nightgown that came down to my knees and a negligee that was mainly chiffon. Next to them were a pair of mules with a one inch heel, and marabou on the toes. They were so beautiful, I could hardly wait to wear them.

After Mrs. Sloan left, Ellen turned to me and asked, “Are you going to put on the nighty that Mommy bought for you?”

“Sure,” I replied. “If you want, we can both put on our nighties and I can read to you. Would you like that?”

“Oh yes,” she said, and shortly thereafter I was wearing the nightgown, negligee and mules and sitting on the couch with Ellen who was dressed in a nightgown and robe sitting next to me.

After I put Ellen in bed, I sat at the kitchen table and worked on my homework assignments for the coming week.

When Mrs Sloan came home a little after midnight, I was seated on the couch watching the television amid a sea of satin and chiffon with my feet up on a footstool. “I see you’re wearing your presents. How do you like them?” she asked.

“They’re wonderful. I love them, but you didn’t have to buy them for me,” I answered.

“But you look so delicious in them,” she said, and with that she sat next to me on the couch. “Everything okay this evening?” she asked.

“No problems whatsoever. Ellen wanted to see me wearing these, so we both got dressed for bed, and I read to her,” I answered. “So how was your evening?” I asked, changing the topic.

“It was nice, but no romance. There were some good looking guys there, but we didn’t connect. However, there was a woman there who seemed interested in me.”

She stood up. “Let’s go into my room so I can take off this dress,” she said, and she grabbed my hand and pulled me up from the couch. Once in her room, she turned her back to me and said, “Unzip me, sweetheart,” which I did.

Much to my surprise, she took off all of her clothes in front of me. I couldn’t help not staring at her naked body. “It doesn’t bother you, does it, seeing me naked?”

“Umm,” I answered, not knowing what else to say. She sat next to me on the bed, and cupped one of her magnificent breasts in her left hand.

“You like?” she asked. I nodded my affirmative.

She stood up, and said, “Let me put on a nightgown,” which she did.

She sat back down and turned to me. “Do you have a girlfriend?” she asked. I shook my head. “How about a boyfriend?”

“Not really,” I answered, “but there is this boy, Joe, who I’ve known for years, who seems interested in me.”

“Howso?” she asked.

“Well, my sister started calling me Tinkerbell when I got my pixie haircut. Joe heard this and kept calling me Tinkerbell. The only way he would stop was if I kissed him.”

“And did you?”

“Yes.”

“Did you like it?” she asked.

“I did,”

“Do you want to kiss me?”

“Yes,” I said in a lowered voice. With that she put her arms around me and pulled my face close to her’s, and we kissed. And kissed again.

“Did you like kissing me?” she asked.

“Yes,” I responded.

When re released our mutual embraces, she looked at me and said, “I was going to ask you if you wanted to keep me company in this bed for the night, but on second thought that might not be a good idea. We might start something we can’t stop.” I nodded my agreement, and with that, we each went to our own beds.

***

The next week Joe and I were walking home from school together, and I was thinking about the kisses with Joe and with Mrs. Sloan. “You never told me why you wanted to kiss me, only that you did,” I said. “So, tell me. Why?”

“I donno,” he answered, “I just did. In fact I still want to kiss you, like right now.”

“Don’t be ridiculous,” I responded.

“Okay. How about later?”

“Not until I know why.” I said, not realizing that by that statement I was agreeing to kiss Joe when he told me why.

“So, if I tell you why, you’ll kiss me again,” he said.

“I didn’t mean that,” I said.

“Well, you’re the one who brought it up,” he said defensively

“Okay, maybe I did, but I don’t have your answer,” I said, “but tell me, are you attracted to me, sexually?”

“You mean, do I want to have sex with you?”

“That’s putting it a little bluntly, but that’s exactly what I mean,” I said.

“Then the answer is yes,” he replied.

“You never told me,” I said.

“You never asked,” he responded.

“Why would I?” I said.

We walked in silence for a few minutes, each lost in our own thoughts.

“So tell me,” I asked, “do you want to have sex with any other boys?”

“No.”

“Girls?”

“The only boy or girl I want to have sex with is you,” he finally said.

“But I’m not a girl,” I interjected.

“You probably could fool nine-tenths of the people on the planet. Not only do you look a lot like a girl, but you look like a very sexy girl, even if you don’t have any tits.”

The thought of tits brought the image of Mrs. Sloan’s naked breast to my mind. Joe and I walked in silence for another minute,

“Look,” I said, breaking the silence, “if you want to remain my friend, this talk of sex has to end right now, and never come up again. That includes kissing and touching.”

“But I thought you liked kissing me,” he said defensively. I didn’t respond. “Okay, I’ll agree with you if you let me see you all dressed up as a girl. Panties and makeup included,” he said.

“I’m not negotiating with you. Every time I do, you twist my words around and I’m agreeing to something I don’t want to do. No conditions.”

Did I mention that Joe wants to be a lawyer?

After another minute of silence, Joe said, “No conditions, but will you let me see you dressed up as a girl anyway?”

“I thought I made this clear, the answer is NO!” I stated.

***

Shortly before Halloween Emily and I were sitting at the kitchen table. Mother walked into the room and announced, “We have to find a costume for Ann, and one of you has to take her around for trick or treating. Who will it be?”

“Chris is so good at it, let him do it,” Emily announced.

“Look, I do all the babysitting,” I said, “it’s Emily’s turn.”

“Okay, if you two can’t agree, I’ll have to ask Ann,” she said. I knew full well that Ann would chose me, so I agreed to take Ann out. “But Emily has to be in charge of getting her a costume,” I added.

A few minutes later Mrs. Benson called. It seems that Mr. Benson had to be out of town on Halloween, and Mrs. Benson didn’t want to leave the house that night. She asked me if I would take her girls out trick or treating. I readily agreed, since I was already taking Ann out, and now I would be paid for my time. It wasn’t long before Mrs. Carlson and Mrs. Sloan made the same request of me, and I would be taking Ann, the two Benson girls, the Carlson’s girl and Mrs. Sloan’s daughter out for trick or treating, and getting handsomely paid for my efforts.

“Are you going to wear a costume?” Mrs. Benson asked.

“I don’t have one, so no,” I answered.

“I have a witch’s costume that I put together a few years ago for a party,” she said. “I found a long black dress with a high collar and long sleeves at a thrift store, along with a black cape, and I bought a witch’s hat and a cheap wig. If you want, you can borrow them.”

“Okay, it sounds like a plan,” I said.

My school allows students to wear costumes to school on Halloween. When Joe asked me if I was going to wear a costume to school, I said that I might.

“What is your costume?” he asked.

“Just wait for Halloween and see,” I replied. An evil thought went through my mind. He wanted to see me in a dress, with makeup, and that’s exactly what I would be wearing, just maybe not as he envisioned it.

I thought that the costume needed a heavy application of green eyeshadow and blood red lips, so I made a trip to the drug store to buy the same.

On Halloween morning I got up an hour earlier than usual. I put on a pair of panties and pantyhose, just because I would be wearing a dress. I put on my training bra, and stuffed a little filling in the cups. Over this I put on a knee length black slip which I borrowed from Mother, and then slipped the dress over my head. I borrowed a pair of black boots from Emily.

“Zip me up,” I asked Mom. The dress was a little loose, but that didn’t matter. Once I had the dress on, I found that there was a slit up the left side, which exposed the lace on the hem of my slip. I also found out that the dress had a pocket, into which I could put my student ID, my phone, and the lipstick.

I sat down at Mom’s vanity, and let her put on a heavy layer of the green eyeshadow. “I think that you need some mascara,” Mom declared, as she applied it to my eyelashes. She then let me put on the blood red lipstick. I was ready, and I headed out the door.

I met up with Joe in the hallway at school, and let out a suitable witch’s cackle at him. He just stared at me for a minute.

“Chris, is that you?” he asked.

“It sure is,” I replied. “You said you wanted to see me in a dress with makeup, so here I am. By the way, you promised that if I let you see me like this, that all talk of sex has to end and never come up again, including kissing and touching.”

“Wait a minute,” he said, “part of the deal had to do with you wearing panties.”

This time I had him. By bringing up a detail, panties, he tacitly agreed with my basic premise of no more talk of sex or touching or kissing. Naturally, I could concede the point of panties, since I was wearing them under the dress, and he would have to agree with the rest. “Okay, I’ll concede that I have to wear panties. That’s hardly a problem, because I am wearing panties under this dress.”

There was nothing he could do, but he didn’t immediately concede defeat. “That’s what you say, but I need proof!”

“Right here, right now, in the hall? That might cause a disturbance,” I retorted.

“No, later, in private, but I have to see it with my own two eyes,” he said, and we walked into class.

It was teasing time. For our first class together I moved my seat close to his right, and when I sat down the parts of my skirt below the slit fell to the right and left, exposing my pantyhose and the lacy hem of my slip. I pretended that I was not aware of this. Joe, on the other hand, couldn’t take his eyes from my shameless display.

This did not escape the teacher’s notice. “If Mr. Joseph Glynn can give me his attention, maybe we can get started.” Lucky for me, the teacher could not see my display, and I did not look at my skirt at all during the class. I also fixed an interested look on my face. Joe, on the other hand, was getting more hot and bothered for the duration of the class.

When the class ended I stood up and executed a quick twirl, which caused my skirt to flare out. I then strutted out the classroom door. I did note that Joe stayed seated, as he squirmed to adjust a bulge in his pants which had grown during the class.

Once in the hall, a girl I knew came up to me. She had been able to see all that had happened. “Great costume, you shameless hussy,” she said with a huge smile and chuckle. “You really had Joe going, not that he didn’t deserve it. Way to go, girl.”

“Thanks, he had it coming,” I replied, and for the rest of the school day, I took every opportunity to tease Joe.

One of the activities of the day was a costume contest. When I arrived at school that morning, one of the teachers handed me a card. “If you’re part of the costume contest, write you name and class grade on this card and pin it to your costume. During the day the student council will be grading the costumes and there will be an assembly after the last class, when the scores for the best costumes will be announced.”

At the assembly, all of the students who wanted to be part of the contest were separated by grade, and went up on the stage. We were asked to walk across the stage, turn at the microphone, say our name and grade, turn again and walk to the other wing of the stage. When it was my turn, I fixed a big smile on my face, strutted to the microphone, did a skirt flaring twist, and said, “Christopher Parker, grade 9.” I then did another skirt flaring twist and strutted to the other side of the stage, accompanied by cat-calls and whistles. When the 9th graders were finished, I found an empty seat next to Joe.

“You’re a hopeless flirt and tease,” he said.

“But you liked it,” I replied.

“Well, yes,” he conceded.

I won second place for my grade, and honorable mention for the entire school, and I proudly pinned the ribbons to my dress.

As Joe and I were walking home, he said, “There still is the matter of the panties.”

“When we get to my house,” I said.

When we got to my house. Joe and I went to my room, and there I proved that I was wearing panties.

There was no time for me to rest on my laurels because now I had to take Ann and my babysitting charges out to trick or treat. All of the girls loved my costume.

“Be back before it gets dark,” Mother said, and we headed out to get treats. Trick or treating went without incident, although I did get a lot of compliments on my costume.

The next day at school I also received a lot of compliments on my costume, all of them from girls. I only got strange looks from the boys. I stayed close to Joe during the day for what protection he could offer. I mentioned the strange looks to Joe, and asked him if I had a problem.

“I don’t think so. Before Halloween, most everyone thought you were kind of weird. Now they’re sure that you are,” he replied. Weird I could live with. Be that as it may, I made sure that I dressed as masculine as possible thereafter, not only at school but also after school, except for my babysitting jobs.

The Babysitter - Part 3
By Petatonic

Thanksgiving can be a hectic time for most families, and mine was no exception. We had Thanksgiving dinner with Mom’s family on the actual day, and celebrated with Dad’s family on the Saturday thereafter.

On Thanksgiving day, we hosted the dinner for Mom’s parents and her brother’s family. I only have one cousin on my Mother’s side, and he is in his twenties. The ‘men’ watched football and the ‘women’ prepared the food. I wore androgynous slacks and a white shirt, and the day was pretty much uneventful. There were some comments about my haircut, but nothing came of it.

Saturday was different. We all met at my grandparents’ house, which was about a two hour drive away. Dad came from a large family, and all of them were there, with spouses and children.

On the way, Emily called me Tinkerbell. Immediately I objected. “Mom, make her stop calling me Tinkerbell,” I complained.

“Emily, don’t call your brother Tinkerbell,” Mother instructed.

“Okay,” Emily answered, “but only for today,”

When we arrived, Dad and my uncles watched some football and drank beer. Mom and my aunts fussed around in the kitchen, getting in each other’s way. I hung around with those of my male cousins who were more or less around my age and watched the games. Emily sat with her female cousins, talking. During a commercial break, I got up from watching football and went to get some snacks and something to drink, and happened to pass my sister and girl cousins.

“While you’re up, Tinkerbell, get me some more popcorn,” Emily said. I shot her a dirty look.

“Tinkerbell?” one of my female cousins asked.

“Oops,” my sister said with a total lack of sincerity, “I’m not supposed to call him that.”

“But why did you?” another cousin asked.

“Look at his hair. He has a pixie cut. Doesn’t he look like Tinkerbell?” Emily said.

While Emily was supposed to not call me Tinkerbell, Mother’s commandment to her had no effect on my cousins. “Now that you mention it, he does,” commented my cousin Ruth.

“With a little makeup, the resemblance would be improved,” another cousin said. I noted that several hands went into purses, and mascara and lipsticks magically appeared. It was clear that a hasty retreat was called for, and I hurried back to the football game.

I tried to remain invisible the rest of the day, but to no avail. After dinner, one of my girl cousins motioned me to come over to her. “Your sister said I should ask you about your Halloween costume. By the way, aren’t you a little old for Halloween costumes and trick and treating?” she said.

“I took my baby sister and some of the kids I babysat for around for trick or treating. I hadn’t planned to wear a costume, but one of the Mothers had a costume and she loaned it to me.” I said.

At this point, Emily piped up, and said, “Tell them about the costume, and don’t forget to mention that you wore it to school on Halloween.”

I decided to refuse to answer that request, and started to walk away. “Not so fast,” one of my cousins said, and grabbed my arm. “We want to know about the costume!”

“If he won’t tell you, I guess I’ll have to,” Emily said. “He dressed as a witch.”

“You mean like a dress and all that stuff?” another cousin asked.

“Naturally,” Emily said. “He sits for the Benson girls, and Mrs. Benson had the long black dress and a witch’s hat. Not only that, but the dress had a big slit up the side. Guess what he wore under the dress.”

“What?”

“Panties, pantyhose and a black slip with lots of lace at the hem,” Emily said with a smug look on her face. “Wait, I might have a photo on my phone.”

Unknown to me she did, and it was passed from cousin to cousin. “You really look like a girl in that dress,” one said, “I like the makeup.”

“Do you like dressing up as a girl, Tinkerbell?” another asked. I walked away before I had to answer that question.

Later on, Emily said to me, “The girls want more pictures of you in a dress, and they asked me to loan one to you. You should be thankful that I didn’t tell them that you have your own dresses.” With that, she started giggling.

That Thanksgiving I only had one thing to be thankful for: none of my cousins went to my school.

***

Joe was over at my house a week later. It was Sunday, and we were in my room preparing for a test on Monday. I had been babysitting the night before, and while I had hung up my blue dress in my closet, I had not closed the door all the way. I guess the color caught Joe’s attention, because he walked over to the closet and opened the door. He pointed at the dress and looked at me. “What’s this?” he asked.

“None of you business,” I replied.

“Is it yours?” he asked.

“Like I said, none of your business,” I answered.

“You don’t deny it, so it must be yours,” he crowed. “You have to let me see you wearing it.”

“I thought we settled all this when I showed you my Halloween costume,” I said.

“But this is different,” he said.

“Look, if you keep this up our study sessions are over. No more help,” I said. Joe knew that this was a real threat, because my help had made a difference in his grades.

“Okay, Okay, I’ll drop it,” he conceded, but I had the feeling it wasn’t quite over.

***

I had made an appointment to sit for Mrs. Sloan’s daughter on Friday night. Since Mrs. Sloan expected it to be a late night, she suggested that I stay the night. She also said that she and Ellen would pick me up at 5:30 and have supper for us.

That Friday, Joe and I walked home from school together, and sat around my house. At 4:45 I realized that I had to get ready, but Joe hadn’t left yet. “Hey, I’ve got to get ready for a sitting job,” I said, hinting that it was time for Joe to go home. He didn’t get the hint.

“I want you to go home, now!” I finally said, forcefully. Well, maybe a little too forcefully, because Emily heard it and stuck her head in the door.

“What’s wrong?” she said.

“I have to get ready for a babysitting job and Joe won’t leave me alone,” I answered.

“I don’t understand,” said Joe. “I’m not bothering him, I’m just keeping him company.”

“He’s not bothering you,” Emily said with a wicked smile on her face, “so what’s the problem?”

“You know what,” I said to Emily.

“Oh, that,” she said.

“Yes, that,” I responded.

“But Joe might like it and find it interesting,” she said, “let me help you to get ready.” With that she went into my closet, pulled out my overnight case, and put it on the bed. It was obvious that we had Joe’s attention. I didn’t think that a four alarm fire would get him to leave.

I had packed the overnight case with my babysitting clothes, including two sets of panties, pantyhose, and training bra. Emily picked out one set and handed it to me. “Go take your shower, Tinkerbell, and I’ll take care of the rest,” she said with a smirk on her face. I grabbed the clothes and headed for the bathroom, but not before I heard her say to Joe, “Tinkerbell likes to dress up as a girl for her babysitting jobs.”

After a quick shower, I came back wearing panties and bra. I sat down and started putting on my pantyhose. I really had Joe’s attention as I ran my hands up my legs to smooth out my pantyhose. “I could help you with that,” he volunteered.

“No thanks, I can do it myself,” I said. It was then that I noticed a bulge in Joe’s pants. “Maybe you should go in the bathroom and take care of that,” I said, pointing at his crotch.

“Maybe you could help me,” he said.

“No way, you pervert.” I replied.

“Look at who’s calling me a pervert. A boy wearing panties,” he said, with a smile on his face.

I tried to ignore him as well as I could, and put on a slip. I then retrieved my blue dress from the closet, the same blue dress that had started everything, put it over my head, and smoothed it over my body.

I turned my back to Joe and said, “You might as well make yourself useful and zip me up,” which he did. I then went to my closet and picked up a pair of one inch heels, which I then put on. I reached into the overnight case and retrieved my makeup bag, fake pearl necklace and bracelet, and began putting on some mascara and lipstick.

“Your lips look so kissable with the lipstick,” Joe said. I scowled at him, “no pajamas?” he said.

“I have some at Mrs. Sloan’s house,” I said, omitting to say that what I had as her house was a satin nightgown and chiffon negligee.

I finished packing by putting some homework and books to read to Ellen in the case. I then started arranging my hair in an unmistakable pixie style.

I turned to Joe. “Okay?”

“More than okay, you’re gorgeous,” he said.

Mother called upstairs to tell me that Mrs. Sloan and her daughter Ellen were out front.

“I guess it’s about time for me to go home,” Joe said.

“About time?” I queried, “It’s more like forty-five minutes late. Not a word to anyone about what just happened,” I added. “If you do, I’ll spread the rumor that you’re hot for me,” I threatened.

“But it wouldn’t be a rumor,” he said, “because it’s true.”

“You’re hopeless,” I said, as I picked up my overnight case, went downstairs, put on a coat and headed to Mrs. Sloan’s car.

When we arrived at her house, Ellen got out of the car and gave me a hug. “There’s Chinese on the table for both of you,” Mrs. Sloan said, “I’m going clubbing, to see who I can pick up, since a certain someone is too young.”

As before, Ellen and I put on our night clothes and I read to her. After that I worked on my homework. About 11:30 Mrs. Sloan opened the door and came in. “Absolutely beautiful,” she said, referring to my satin nightgown and chiffon negligee. “I have a new friend, Sylvia, who should be here any minute. If you don’t want to meet her, you might want to go to your room, but you don’t have to.”

“I have to put my homework away, before I go to bed,” I said. I was half-way through with this when Sylvia arrived.

After Mrs. Sloan introduced us, Sylvia said, “My, oh my, what do we have here? She’s pretty as a picture. I could just eat her up.”

“The paint’s not dry on that picture, she’s only fourteen,” Mrs. Sloan told Sylvia as a warning.

The two women wanted a night-cap and invited me to keep them company. I sat as demurely as I could as they discussed the nightclub and who was there, and very candidly discussed what each of them wanted to do to some of the patrons. It was slightly embarrassing and I began to blush.

“Oh, look,” Sylvia said, “she’s blushing. Isn’t it precious?” I just blushed the more.

While we were sitting, I noticed that Sylvia’s hand was below the table, and Mrs. Sloan was squirming, as if someone was rubbing her leg, which in fact was exactly the case.

“Why don’t we go upstairs,” Mrs. Sloan said.

“Great idea,” Sylvia replied, and she grabbed my hand and all three of us went into Mrs. Sloan’s bedroom. I really wanted to go to my own room and bed, but Sylvia would not let go of my hand.

“Unzip me, please, honey,” Sylvia said as she released my hand.

“Same here, darling,” Mrs. Sloan requested. Both women took off their dresses, and followed it with the rest of their clothes. Mrs. Sloan put on a nightgown, and handed another to Sylvia.

“Now we all match,” declared Sylvia, as she rubbed my behind.

It appeared that things were getting dangerous. “I think that I’ll hit the hay,” I said, and headed for my room and bed.

Sylvia had left by the time Ellen and I rose. I found Mrs. Sloan sitting at the kitchen table, drinking coffee. “I made a pot,” she said, “help yourself.”

When I poured a cup and sat down, Mrs. Sloan said, “Sylvia’s a bit brazen, isn’t she, but that’s exactly what I needed. She’s a really great lover, but you wouldn’t know about that, would you?”

“Hardly,” I replied.

“Well, if you ever wanted to learn, she could give you post-graduate courses,” she said with a snicker.

Before we left for my house, Mrs. Sloan pulled me close to her and gave me a long passionate kiss, which I gladly returned.

***

There was a threat of snow in the air and the Christmas lights were shining through the twilight. Today was the last day of school until the new year. Naturally, on a weekend night in the Christmas season, I had a babysitting job. This time for as family named Werner. I had not sat for them before. They were friends of the Bensons, and the Bensons were hosting a Christmas party and the Werners, along with my parents and the Carlson were invited but the Werners didn’t have a babysitter. The Bensons recommended me to them.

That was great, but the best part of the evening was that Emily had to stay at home and sit for our sister Ann. I was getting paid and she was not. How wonderful.

“I think that Tinkerbell should give me half of what she gets,” she complained.

“I’ll think about it,” I said, “if you stop calling me Tinkerbell. Otherwise all you get is pixie dust.”

The Werners had two sons, Steve, aged 10 and Robert, aged 11. Babysitting for boys was a new experience for me, and I decided that I would I would not dress as a girl. I didn’t think that they wanted me to read to them, so I didn’t bring a book. Almost as an afterthought I grabbed a deck of cards and put it in my pocket.

Robert made it clear that he didn’t think that he needed a babysitter. It didn’t look like it was going to be an easy evening. I then remembered that I had a deck or cards, and I put it on the kitchen table.

“Do you guys know how to play cards?” I asked.

“Yeah,” answered Robert.

“Any particular games?”

“Nah,” responded Steve.

“How about blackjack?”

“No.”

So I taught them how to play blackjack. We used uncooked macaroni as pretend money. After that I taught them some of the various poker games.

It was going to be an early evening, and the Werners returned home before the boys’ bedtime. “Did you boys behave yourselves?” she asked them.

“Yeah, Chris taught us some card games,” said Robert.

“Can Chris sit for us again?” asked Steve.

“Well, that’s something new,” said Mr. Werner, “where did you learn to sit for boys?”

“I just remembered what I liked to do when I was their age, and went from there. I listen to what they say, and don’t talk down to them. When I was their age, I liked to hang around with the older boys,” I explained.

“Well, the Bensons were right when they said you are a good babysitter,” Mrs. Werner said, and she paid me along with a good tip.

“If you’re ready, I’ll give you a lift home,” Mr. Werner said. While in the car, he told me that he was a psychologist, and concentrated in gender issues. “I wouldn’t expect that you have any ideas what that’s about, do you?”

“A little,” I answered.

“Do you know what gender dysphoria is?” he asked.

“Yeah, that’s when a boy thinks he should be a girl, and the opposite for girls,” I said.

“Wow, either you are well read, or I may be touching into a sensitive area,” he commented, almost to himself. Nothing more was said until I arrived home.

I had the opportunity to again sit for the Werners a short time later. Before they left for the evening, Mr. Werner said he wanted to talk to me and we went into his study. “You’ve sat for the Carlsons, haven’t you?”

“Yes,” I replied.

“Now you don’t have to answer the next question, in fact you can tell me to mind my own business,” he said. “Do you remember Mrs. Carlson saying that you will be a good mother?” I thought about what he said, and took a few moments before I answered.

“Yes, I remember, and she did say that,” I answered softly.

“Wow,” he said to himself. He then turned and looked directly at me. “Thank you for being candid with me. As I told you, I’m a psychologist, and everything you told me is confidential. I’m not allowed to tell anyone, not even my wife, and certainly not my children.”

When the evening was over, I told my parents how different it was sitting for boys, as opposed to girls.

“But did you have fun?” Mother asked.

“Yeah, I taught them to play blackjack and poker. They loved it, and the evening seemed to fly by,” I answered.

“What did you think of the Werners?” she asked.

“I like them,” I said, especially Mr. Werner. Did you know he is a psychologist?”

“I think I heard that somewhere.” she said.

***

On the first Monday of the Christmas break, I was contemplating going shopping for Christmas presents. Before I left, Joe called, and I invited him to come along with me. “Maybe we could catch a movie,” he said, and then added, “if you pay for it.”

I had made a list. I would get barrettes or hair bands for the girls for which I sat, and a deck of cards for each of the Werner boys. For Ann, I bought a Barbie Doll, for Mother a CD of oldies, for Dad, a book about golf. That left Emily. I wanted to get something appropriate for her, and that required more thought. That first day, Joe and I just window shopped. I ended up treating Joe to lunch at the food court, and we just wandered aimlessly until it was time for the movie to start. It was an action movie, with lots of car crashes and explosions, but not a lot of plot or quality acting. As usual, I paid for the admission, popcorn and drinks.

Once the movie started, I felt Joe’s hand on my knee. “Stop that,” I whispered, “remember, you promised no touching.”

“But you’re so touchable. When I think about you in a dress I just want to touch you,” he replied in a whisper.

“But you promised,” I responded.

“Sheesh,” he complained. “Okay,” he finally conceded and moved his hand.

But not for long. It might have been fifteen minutes later, and his hand was back, this time rubbing the inside of my thigh. I was tempted to pour what was left of my drink on his head but restrained my impulse. I remembered how Emily used to complain about boys rubbing her leg at the movies.

“Knock it off,” I whispered into his ear.

“But it feels good, doesn’t it?” he said in the nature of a response. I didn’t answer that. Rather, I said, “If you don’t stop now, I’m walking out of the theatre.

“Okay, Okay,” he said.

A half an hour he was at it again. This time he got a physical reaction from me. I couldn’t very well walk out of the theatre with a big bulge in my pants. I was tired of fighting him, so I stood up and moved to a different seat. He did not follow me.

When the movie was over, and we were far enough that no one could hear me, I lit into him. “Joe, you promised. I’m really pissed at you. Come on, both of us are boys. Don’t ever do that again to me.”

“I’m sorry, I thought you’d like it,” he said sheepishly.

“Well I didn’t!” I said emphatically, “I thought I made that perfectly clear the first time you did it.”

Regardless of what I was saying, deep down in me I did like it, not that I’d ever admit it to Joe.

We wandered around the mall, until Joe saw an ice cream store. “Just to show that you’re not mad at me, I’ll let you buy me a shake,” he said.

“What? Where’s the logic in that?” I spouted off.

“I donno,” he said, “I just want a shake.”

“Okay, if you promise to behave yourself,” I said.

“Does ‘behaving’ include behaving badly?” he asked with a silly grin on his face. I didn’t grace that with a comment.

***

By the end of the week I had all of my Christmas shopping done, which was good, because I had no money left. For me, that was not a problem, because I had three babysitting jobs lined up for Friday, Saturday and Sunday, which would put a good amount of money in the coffers. I finally decided to get Joe a gift card for the ice cream shop, good for ten shakes. For Emily, I bought her a nice maroon skirt.

Buying the skirt was an interesting adventure. Joe was with me and I was dressed androgynously in jeans and a sweater. I had seen the maroon skirt on a mannequin in the window and I looked through the racks of skirts until I found it in the proper size, and took it to the register. The clerk looked me up and down, and with a smirk finally said, “Aren’t you going to try it on, Honey?”

“It’s a gift for my sister,” I explained.

“I’m sure it is,” the clerk responded with a voice dripping with disbelief. “But why don’t you try it on, anyway?” she said.

Joe was no help. “Why don’t you try it on. I’d like to see how you look in it.”

“Listen to your boyfriend.” the clerk said.

I finally gave in and went to the changing room with the skirt. “When you have it on, come out and let me see how it fits you,” the clerk said.

“Yeah, I’d like to see it too,” added Joe.

I put the skirt on and stepped out of the changing room. The devil in me decided to give it a twirl, much to the pleasure of Joe and the clerk. “It fits you well,” the clerk said, “but if you are going to twirl like that you should have a matching pair of panties.”

“She’s right,” said Joe. I just gave him a dirty look, but in the end I bought the panties.

***

All of the children for whom I bought the gifts seemed to like them, especially Ellen. When I stopped at the Sloan house, Mrs. Sloan invited me inside to give Ellen her present. While there, I saw Sylvia sitting on the couch. I was wearing girls’ jeans and a frilly top under my coat. “Take off your coat and sit next to me,” she said, as she patted the cushion.

“I’ve got to take Ellen to see her doctor, Mrs. Sloan said, “Why don’t you stay here and keep Sylvia company while we’re gone. It shouldn’t be more that an hour.”

“I’ll take good care of her while you’re gone,” Sylvia said. Yeah, like a shark takes care of a food fish, I thought.

Not twenty seconds after the door closed behind Mrs. Sloan and Ellen, Sylvia had her left arm around my shoulder, and her right hand on my knee. Oh boy, I thought, just like Joe in the theatre. I loved what she was doing, but I knew it could quickly get out of control. I finally steeled myself and said, “Remember, I’m only fourteen.”

“That’s right,” Sylvia said, “I kind of forget that when I see you. You may not know it, but you drive me wild.”

“Would a kiss help?” I asked.

“Definitely,” she answered, and we held each other highly and enjoyed a long lingering kiss.

I realized that Sylvia had only seen me as a girl. “Did Mrs. Sloan tell you that I’m a boy?” I asked.

“No, she must have forgotten that. You don’t look like a boy. Are you really a boy?”

“Yes, last time I checked this morning in the shower I was,” I said.

“But you are so delicious as a girl. Having boy parts just makes it ssoooooo much better,” she said with a big grin on her face.

Sylvia and I petted and kissed until Mrs. Sloan and Ellen returned.

“I can hardly wait until you’re eighteen,” Sylvia said.

“Get in line,” responded Mrs. Sloan, with a smile.

***

After Christmas, Joe and I decided to cruise the mall to see what bargains there were. I was flush with cash from all of my babysitting, and Joe, naturally, had none. I think my purpose of being there was to pay for everything.

“How about a movie?” he suggested.

“Are you paying?” I asked, even though I knew the answer.

“Well, no,” he replied. “I’m kinda broke.”

“I don’t know,” I said. You certainly didn’t behave yourself last time we saw a movie.”

“It’s not my fault,” he said, “when I’m with you I kinda lose control. It’s your fault for being so foxy.”

“Good grief,” I responded.

As we aimlessly walked around the mall, I noticed that Joe was pausing and intently studying some of the dresses in the store windows. “See anything you like?” I asked him.

“I’d like to see you wearing them,” he replied.

“No, not for me, for you. Any you’d like to wear?” As I said it, I noticed that Joe was blushing.

“You’re blushing!” I crowed triumphfully. “You really want to wear a dress!”

“Umm. Err, no,” he stammered.

“Think silky panties caressing your body,” I whispered to him with an evil smile on my face. Joe’s face just got redder. “I could buy you a pair, and you could wear them under your jeans. No one would know except you and I.”

“But you aren’t wearing panties under your jeans,” he protested.

“You never know, and in this case you never will,” I observed saucily.

At this point we were passing a lingerie shop. I grabbed his arm. “Look,” I said with a smirk on my face, “You can go in and buy a pair. I’ll give you the money, and wait out here for you. I’m sure the sales clerks will be MOOOST helpful, but you’ve got to tell them that you’re buying them for yourself.” I had to chuckle at Joe’s obvious discomfort.

“Err, no!” he said.

“Maybe some other time,” I said, continuing to tease him.

“No.”

Despite his protestations, I think I had him. A thought crossed my mind. Valentines day was coming up. Maybe a Valentine’s day present for Joe? Pink, lace trimmed, with little red hearts? I smiled at my own cleverness.

I looked at my watch. I had a babysitting job tonight with the Bensons. They had invited the Carlsons over for dinner, and I was babysitting the Benson’s girls and the Carlson’s daughter. I had bought a delightful pair of burgundy slacks with a side zipper and some burgundy shoes, both of which I wanted to wear tonight. Unfortunately, the slacks had no pockets. I needed a burgundy purse.

“I need to buy a purse,” I told Joe, “and then I have to get home to get ready for a babysitting job.” I looked around, and saw a store that was likely to have what I wanted. I went over to a display of purses while Joe meandered around.

“Can I help you?” a clerk asked.

“Yes, I need a burgundy purse, not too expensive.” I was wearing masculine clothes and the clerk gave me an odd look. “Oh, not for me,” I lied, “for him. He’s too embarrassed to buy it himself.”

I called to Joe. “Come over here. How is this one?” I asked.

“Alright, I guess,” Joe mumbled. The clerk transferred her odd look from me to Joe.

As we were leaving the store, Joe asked, “Why was the clerk giving me funny looks?”

“I told her that the purse was for you, but you were too embarrassed to buy it yourself.”

“Gee, thanks,” he said sarcastically.

“Get used to the looks. You’ll see a lot of them when you buy lingerie for yourself.”

“Fat chance,” he rejoined.

***

New Year’s Eve was only a few days away, and babysitters were in high demand. The Bensons had booked me a month ago, and the plan was that I would sit the Benson girls as well as the Carlson’s daughter at the Benson’s house. Because it would be a late night, It was decided that the girls and I would spend the night at the Bensons. This would mean that I needed some sleep wear. I didn’t think that the nightgown and negligee that Mrs. Sloan gave me would be quite appropriate, and, in any event, I kept them at Mrs. Sloan’s house.

It just so happened that Joe was at my house that day. “Mom,” I called out, “I need to go to the mall. Can you take me there?”

“Sure, honey, what do you need?” she asked.

“Some sleep wear for New Year’s Eve,” I responded.

“Can I go along and help you pick something out?” Joe interjected.

“If I let you pick something out, it would most certainly be a ‘naughty nighty,” I said. “I’ll probably end up with some uninteresting pajamas, a terry cloth robe and some plain slippers.”

“Now, I have to get ready, so scoot,” I said.

“I thought I’m going with you to the mall,” he said, “and I can help you get ready.”

“I don’t need your help,” I said.

“Yeah, but it’s more fun when I help,” he said

“Fun for you, not me,” I asserted.

Since Joe made no sign of leaving, I decided to get ready in front of him. Maybe he’ll get embarrassed, and leave, I thought. Not a chance, was my next thought.

So I undressed, until I was totally naked. I noticed Joe staring at my crotch as I started to put on a pair of panties. “Pervert,” I said.

“Me a pervert?” he replied, “Just like the last time you called me that, I’m not the boy wearing panties.” I just gave him a disgusted look as I put on a bra and nylon knee highs.

“No pantyhose, no dress?” he said as he saw the knee highs.

“What is it about you and dresses?” I said, and then I paused, “Oh yeah, now I remember, you want to wear a dress.”

I put on the burgundy slacks that I recently bought, and an ivory blouse with ruffles, to disguise my lack of boobs. I put on my burgundy shoes, and grabbed my burgundy purse. “A little lipgloss and mascara, and I’m ready,” I told no one in particular.

Mother decided to accompany Joe and me on my shopping expedition. True to form, Joe wanted me to get a baby doll that was more chiffon than substance. I, on the other hand, liked a pajama set in ivory satin.

“Those look like boys’ pajamas,” Joe complained.

“No they don’t, the buttons are on the other side, and there’s no fly,” I explained.

“But they’re not very sexy,” he said.

“If you want sexy, go buy yourself a baby doll and wear it,” was my final comment.

***

New Year’s Eve was hardly exciting for me. Hardly exciting, but profitable. Of course, I enjoyed entertaining the girls as much as they enjoyed me entertaining them. I had brought some sparkling grape juice and some plastic champagne flutes. By 10:45 the girls were drooping, and they would never make it to midnight, so I declared that we were sophisticated New York ladies, and therefore on New York time. That way we could welcome the new year at 11:00 local time, an idea the girls loved.

After the girls were in bed I put on my new pajamas, robe and slippers, put some music on, cleaned up the house and started reading. The Bensons and Carlsons finally rolled in about 1:00 a.m. “You’re still up,” Mrs. Benson said, more of a question that a statement of fact.

“I wanted to make sure that you party animals got home safely,” I responded.

“Yes Mother,” Mrs. Benson said with a laugh. Mrs. Carlson smiled with a knowing look on her face.

I related how the girls and I had spent the evening, and said that they were all safely tucked into bed. “Oh my,” Mrs. Benson said, “you even cleaned up after your little party.”

“Just like a good Mother would,” said Mrs. Carlson, approvingly.

“Those are pretty pajamas and robe,” Mrs. Benson said.

“Thank you,” I said, “I bought them specially for this evening. I wanted to look good for the girls.”

A few minutes later the Carlsons left and everyone retired to bed.

The next morning I was up before anyone else, and started a pot of coffee. Mrs. Benson came into the kitchen a while later and I poured her a cup of coffee. “I could get used to having someone waiting on me like you do,” she commented, with a smile.

“What had you planned for breakfast?” I asked her.

“How about pancakes and bacon?”

I immediately started the breakfast, while Mrs. Benson sat and savored her coffee. “Would you like me to warm that up?” I said, pointing at her coffee cup.

“Yes Mommy, if you please,” she said with a big smile.

I was flipping pancakes when Mr. Benson and the girls showed up in the kitchen. “Something smells awfully great,” said Mr. Benson.

“Chris did everything,” Mrs. Benson said, “all I did was sit here and drink coffee.” She turned to the girls, and asked, “Did you girls have a nice New Years Eve?”

“Oh yes,” responded Susan. “Can we do it again?”

“Maybe,” Mrs. Benson answered, “We’ll have to check it out with Chris.”

On my way back home, I reflected that all in all it had been an enjoyable and profitable evening. I ruminated on how Mrs. Benson and Mrs. Carlson had made reference to me as a Mother, even if it was in fun. Maybe there was a bit of truth in it. I had to admit that I liked being a ‘Mommy.’

***

My first counseling session for the new year was two weeks after New Year. “It’s time to evaluate your progress so far,” my Counselor said, “so I’ve asked Dr. Werner to join our team. I understand that you might already have met him.” Let me call him in.

Dr. Werner was the same Mr. Werner for whose boys I had babysat. What followed was a whole lot of consents from everyone, since I knew Dr. Werner from outside of the counseling center. I liked Dr. Werner and was happy to have him on my ‘team.”

“One of the problems with this is that I may hear things about you outside of these four walls which might influence me. If you don’t like that, I’ll bow out of the case,” Dr. Werner said.

“What have you heard about Chris?” Mother asked.

“That he is the best babysitter one could ask for. Also there is the opinion that he would, or will, make a great mother,” Dr. Werner replied.

My Mother just beamed.

“Now Chris,” he continued, “I understand that when you sit for girls, you dress in feminine clothes, and when you sit for boys you dress as a boy. Is that true?

“Yes,” I replied, “It just happened that way,” and I explained what had occurred.

“Do you like dressing as a girl, wearing dresses or skirts?” he continued.

“I do,” I said, “it kind of feels just right.” I answered.

“I see,” he said. “How about when you dress as a boy?”

“Well, I really have to for school, or when someone might see me and connect the boy Christopher with the girl Christine.” I replied, “It doesn’t bother me to dress like a boy, but if I could I would always dress like a girl. And then there are the occasions when I dress somewhere in between, when I think that it would be a good idea.”

“From what I’ve heard, you make a very convincing girl,” he added.

“Thanks,” I responded.

“Any problems at school?” he asked.

“Not really,” I answered, “most of the kids think I’m a weird boy with a funny haircut, and pretty much ignore me. One thing I have to watch for is acting like a girl when dressed like a boy.

“Oh?”

“Yeah,” I responded, “I have, or maybe had, a friend named Tom. His Mother saw me sitting and walking like a girl, and she found out that I cross dress. She told me to never be alone with Tom. She told me that Tom’s Dad is a homophone.”

“Do you ever see Tom anymore?” he asked.

“Sure, every day at school, and when a group of kids do something, but never alone. I’m kinda scared of his parents.

“Do you ever have sexual urges when you are near Tom?” was the next question.

“No,” I replied.

“Tell me about other friends?”

“I’m sort of friends with some of the girls at school, especially if we went to grade school together, but we’re not close, we don’t share confidences,” I said.

“How about boys?” he asked.

“For the most part, I am friends with some boys from grade school, but not close. I’m pretty much a loner.” I answered. “And then there’s Joe,” I added.

“Joe?” he asked, “tell me about him.”

“He’s probably my closest friend. I’ve known him for ten years. We hang around with each other a lot. He’s the only boy who’s ever seen me in a dress, other than my Halloween costume.”

“Anything sexual there?”

“Yes, I’d guess you’d say so if you’d call a kiss sexual,” I answered. I looked at Mother to see her reaction. She was frowning. I decided to be less than candid about Joe and me.

“So you kissed him?” Dr. Werner asked.

“Or he kissed me,” I said, completing the question.

“How did that make you feel?” he asked.

“As a boy, I was disgusted,” I said, “but the girl deep inside of me kind of liked it.”

At that point the time was up and the session ended. On the way to the car, Mother said, “I didn’t know that about Joe. Maybe you should stop being his friend.”

“Oh Mom,” I complained, “Joe’s the only real friend I have. I can handle him. Don’t worry about him.”

***

The next day Joe stopped at my house to study for a test. Mother gave him a strange look, which was not lost on Joe. “Your Mother looked at me kind of funny,” he said to me, “Do you know what that’s all about?”

“Yeah, she thinks that you’re after my body,” I answered.

“Well, she’s right,” he responded.

The Babysitter - Part 4.
By Pentatonic

It was an ugly late January day. Gray skies, sleet, and dirty snow on the ground. Joe and I were walking to my house to study. “My church is having a Valentine’s Day party for teens,” Joe said, “You interested?”

“Maybe, depends,” I answered.

“Depends on what?” he asked.

“Like is it couples only? Do you have to pay to get in?” I replied. I didn’t want to go as a couple with Joe. I asked about an admission price, since there are not as many babysitting jobs in late January, and my funds were running low. I was sure of one thing, Joe had very little or no available cash.

“I think it’s open to any teen, but there will be couples there,” Joe said, “I think that they charge something to get in, to pay for the refreshments, and stuff like that.”

“Will there be dancing?” I asked.

“Yeah, I think so. They’ll probably have a CD player.”

“Are you going?” I wanted to know.

“If you will,” Joe said.

“You mean, like a date?” I asked.

“Yeah, well sorta,” was his evasive reply.

“Well, either it is a date or it isn’t. Which is it?” I demanded to know.

“It is a date,” he said.

“As in a boy and a girl?” I asked.

“Yeah, I guess so.” Another evasive answer.

“If we’re going as a couple, who’s the girl, or do you plan on two boys as a couple? I don’t think that would be a good idea, Rumors would be sure to follow,” I said.

“I kind of figured that you’d be the girl, since you already have some dresses, and you’re better looking than I am,” Joe posited.

“I’ll agree with you that I’m better looking than you, but why do you always want me in a dress. Isn’t it your turn?” I asked, “or is it that you have some evil intentions to have your way with my tender body?” I had to smile when I said that.

I paused for a moment. “I have to think about it,” I added, “If I get a babysitting job for the same evening, I’m taking the babysitting job over a Valentine’s Day party. Anyway, no matter what, I’m not going as a girl.”

The matter of the Valentine’s Day party was dropped when we arrived at my house and started to study. Ever since Mother had found out that Joe and I had kissed, we did our studying at the kitchen table, in plain view of everyone, as opposed going up to my room. This pleased Mother.

Just before Joe left, I penciled in the date of the Valentine’s Day party on the family calendar. My sister Emily saw me do this, and she came over to see what I had written. “OOH, Tinkerbell is going to a Valentine’s Day party,” she crowed, “are you going with Joe, like on a date?”

I just shot her a dirty look, but Emily wouldn’t let it drop.

“Hey Tink,” she continued, “I have a nice red dress which you can borrow. How does that sound to you Joe? Think that Tinkerbell would look nice in red?” Emily didn’t expect a response, so she left the room laughing.

“Mother!” I complained loudly. “Make her stop.”

“Just ignore her,” was my Mother’s useless advice.

***

I had a babysitting job with the Werners that weekend, so I drew an action movie from the library and looked at the rules for some card games. I wanted enough to keep the boys interested.

I had been unhappy that Mother had heard about Joe and me kissing. I didn’t mind telling the counselors; I just didn’t want Mother to know. So when I arrived at the Werner’s house, Mrs. Werner was still getting ready and I asked Dr. Werner if we could talk for a minute.

“Sure,” he said, “is this part of your counseling?

“Yes,” I answered, “When I admitted that Joe and I had kissed, it upset Mother. There are some things that I’d rather that Mother not know about, but I think that you as a counselor should know. Is there any way I could have a session without Mother in the same room?”

“I see your point,” he answered, “I can arrange that your sessions be one on one with the counselor. Don’t worry about it.”

“Thanks,” I said, “it means a lot to me.”

***

A week before the Valentine Day party, Joe and I were walking to his house from school. “Joe,” I said, “I’ve been thinking about the party next weekend. If I go, I’m not going as part of a couple. You and I can go, but not together. It’s that or nothing.

“I guess that means you won’t be wearing a dress,” he said.

“You’ve got that right,” I responded, “but that doesn’t mean that you can’t wear a dress,” I added with a chuckle.

So it ended up that Joe and I went as singles, not as a couple, and neither of us wearing a dress. There were a lot of kids who were there without dates, so coming as a single was not a problem. There were a fair number of girls, and it was a lot of fun mingling with them. Having an older sister who made me learn how to dance meant that I was a fair dancer, a lot better than most of the boys there, which meant that I did a lot of dancing.

My friend Tom was there, and after a while he and another boy came over to Joe and me.

“Joe, Chris, I’d like you to meet Fred, a friend of mine. He goes to a different school, so I don’t think you’ve ever met him. We shook hands and exchanged greetings. Then something unusual happened; I caught Fred ‘checking me out.’ I knew what this was since I had been checked out by boys who thought I was a girl, but this time I don’t think that I looked like a girl. Then I saw him check out Joe.

I noticed that while Joe and I danced with a lot of girls, neither Tom nor his friend Fred danced with any of the girls. I also noticed that they touched each other more than usual for two boys. I pointed this out to Joe.

“What do you think?” I asked Joe,

“They’re acting a lot like a couple.”

“Are they an item?” I asked.

“Could be,” Joe answered, “but then that’s not our concern.”

“I’m not sure,” I responded. “Did you see Fred checking you out?”

“Yeah, but he also checked you out, and you are much more checkable than I am.”

“Oh well, it’s not my concern,” I concluded, “or yours, unless you want it to be.”

“You’re the only one I’m interested in,” Joe said. “It’s a shame that we can’t dance together.”

“No, it isn’t a shame,” I declared, “if we danced, you’d probably try to have your way over me.”

“And that’s bad?” Joe said with a smile.

“You’re hopeless,” I said, and nothing more was said about Tom and his friend Fred.

Several of the girls made it plain that they would like to date me and we exchanged phone numbers. Over the next week some of them called me, much to the evil delight of Emily, who referred to them as my harem. “Hey Tinkerbell, another one of your harem called. Do you think she wanted to discuss clothes? Did you tell her about the fetching blue dress that you love to wear?” she said.

***

On the day before the actual Valentine’s Day, decided to make good on my intent to give Joe a pair of panties as a Valentine’s Day gift. I first dressed myself in panties, slip, bra and dress and headed off to a nearby lingerie shop. I had been sneaky getting Joe’s measurement. His waist size was easy. It was on the leather label on his jeans. His hip size, which was important, took more effort. I was able to wrap a string around his hips saying I wanted to compare my hips to his because I thought that my hips were getting bigger. I think he went along with it, not because of my weak excuse, but because I let him rub my butt when I measured him In any event, I had the measurements, and I was able to figure out that a size 5 panty should do the trick.

I found a darling pair of pink satin panties with little red hearts and with lace at the waist and leg holes. I’m smaller that Joe, so when I brought them to the register the clerk questioned the size, but I assured her that it was correct. I told her I had a big butt.

I put tissue paper around them and put them in a little box, which I decorated with a big red ribbon and a bow.

When I went to Joe’s house on Valentine’s Day to study, I brought my present with me. We were studying algebra, and during a pause, I said, “Joe, I have a Valentine’s Day present for you, and handed it to him.

“I didn’t know that we were exchanging gifts,” he said.

“We’re not, I don’t expect a gift in return,” I told him.

He carefully opened the gift, and when he saw what it was, he was surprised, and he began to blush. “I want you to wear them under your regular clothes, and feel the silky softness.”

***

Of all the girls which I had met at the Valentine’s Day party, one, Sue Hitchcock, kind of interested me. Not that she was a raving beauty, she was rather plain and a bit overweight, but she had a delightful personality. We talked several times on the phone, and I steeled my courage and asked her out for a date for the next Saturday, to catch a movie and pizza. When Joe found out he accused me to two-timing.

“Why do you want to go out with her?” Joe asked.

“Because I’d like to see a movie without someone pawing all over me,” I replied.

Sue wanted to see a new movie, which was definitely a ‘chick flic.” I certainly had no objection to that. When we sat down in the theatre, she took my hand in hers and smiled at me. After a time, I put my arm around her shoulders and she snuggled up to me. During one particularly romantic part of the movie she put her finger on my cheek and turned my face toward her. She leaned her head toward mine, and I felt her lips on mine. I squeezed her a bit, and kept my lips on hers.

I had no idea what to do next, if anything, since the farthest I’d ever gone was a kiss, except for Joe’s groping, and I didn’t think Sue wanted me to grope her. “You’re awfully shy,” she whispered to me, “I like that about you.”

***

Joe showed up at my house the next day, and boy, was he nosy. “Did you kiss her?” he demanded to know.

“A gentleman never kisses and tells,” I said smugly.

“That means you did, otherwise you would have said that you didn’t kiss her,” Joe posited, “Did she let you touch her tits?” I ignored that question. “You never let me touch your tits,” he said accusingly.

“How could I,” I said, “I don’t have any tits for you to touch.”

“That’s beside the point,” he said.

“No it isn’t,” I said, “I think that you’re more than a little jealous. Why don’t you go on a date with one of the girls you met at the party?”

“No money.”

“Lame excuse,” I said, “If you really wanted to go on a date, you’d find a way to get some cash. I think that the real reason is that girls scare you.”

“You don’t scare me,” Joe replied.

“That’s because I’m not a girl,” I responded.

***

St. Patrick’s Day was just around the corner. While my family didn’t do much about it, Sue’s family did. They were going to have an afternoon feast on corned beef and cabbage, and had invited a lot of their friends. Sue invited me, and I accepted. I told my mother about the invitation and asked her what I should wear.

“Green!” Emily interjected. “You know, maybe like that little green dress that Tinkerbell wears. I’m sure that your new girlfriend would love that,” she added with a laugh.

Mother and I ignored her. “You don’t know if it is casual, so you should overdress a little and wear a coat and tie. If it isn’t casual, you’re okay. If it is casual, you can take off the coat and tie. You might want to consider getting a green tie for the spirit of the occasion.”

That turned out to be good advice. I was able to find a green tie, and wore it with my only sport coat. When I arrived at Sue’s house, most of the men were wearing coats and ties. “I like your tie,” Sue’s Mother said with approval.

Sue took my hand and introduced me to everyone there. After that, I was talking with one of Sue’s cousins, “Sue has a kind of possessive look on her face. She better not catch you chatting up another girl, or there may be a cat fight.”

Sue and I were alone for a few minutes, when she said, “Do you like me?”

“I do, why do you ask?”

“Well, we’ve kissed, but you never tried anything further with me, and I wondered,” she said.

“I didn’t think you wanted me pawing and groping you.” I answered, remembering how I didn’t like Joe’s advances.

“Ever the gentleman,” she said. “I like that about you,” and she kissed me. “By the way, girls don’t send out engraved invitations when they want to go beyond just kissing.”

At that point, Sue’s Mother came into the room, saw Sue and I holding on to each other, and beat a hasty retreat. “Your Mother saw us,” I said.

“She did, but did you see how quickly she left,” Sue observed. “She must like you and want to encourage our romance, which is why she left so quickly.”

“Oh.” I said.

“You haven’t have a lot of experience with girls, have you?” she asked.

“Um, well, no,” I mumbled.

“How sweet,” she said with a big smile.

Sue and I continued to date, much to Joe’s chagrin, and I didn’t need that engraved invitation, but she let me know when I went too far.

I came to really love dating Sue, even if I wanted to be a girl. Boy, was I confused.

***

The weather in March can be just as miserable as it is in January, and on the last Saturday of the month Joe called. I could tell that there was something wrong, by the tone of his voice. “Is your mother home? We need her to drive us.”

“What’s wrong? What happened?” I asked.

“It’s Tom. His Dad caught him in bed with Fred, doing you know what, and he kicked Tom out of the house. Tom’s sitting on the curb with his clothes in garbage bags. We have to pick him up and bring him some place warm and dry.”

I explained to Mother what was going on. She put a complaining Emily in charge of Ann, and we headed off to Joe’s house. Immediately after Joe was in the car we drove to Tom’s house, and found him sitting on the curb, crying. Joe went over to Tom and picked him up and hugged him. Meanwhile I popped the trunk and loaded the garbage bags. We were there only a minute before Tom’s Father came outside, yelling, “I don’t care where you take that queer fagot, just get him out of my sight. I never want to see him again, and tell him to never come back here!” It was actually very frightening, with the yelling and crying.

“Okay, where to now?” my mother asked when we were all back in the car.

“Maybe my house,” Joe said, “we have a spare bedroom for Tom.”

We got Tom and his belongings into the house, and Joe sat with Tom on the couch, cradling Tom in his arms.

“You need to get a hold of your parents, Joe,” Mother said.

“I already did, before I called you. They should be here in about a half an hour.”

Mother sat on the couch with Tom between her and Joe. “Honey, your friends are here for you. Remember we are here to support you. You’re not alone,” she said.

When Joe’s parents arrived, Joe filled them in with what happened. “Should we contact the authorities?” Mother asked to no one in particular.

“Maybe I should call Tom’s mother,” Joe’s mother suggested.

Joe’s dad knelt in front of Tom. “Did anyone hit you?” Tom nodded his head, and between sobs, he said, “Yes, my dad.”

“Where did he hit you, on the face?” Joe’s dad asked.

“That should be obvious,” Joe said, “look at his black eye and swollen nose. The swelling is getting worse by the minute.”

“He needs to see a doctor,” Joe’s dad said, but first we need to call the cops. He then went to the phone, and dialed 911. He related what he knew to the dispatcher.

“The police should be here soon.” he reported.

A half an hour later a police car arrived, and Mr. Glynn, Joe’s dad told the officer what he knew. The officer squatted in front of Tom. “Is that what happened?” he asked Tom. Tom nodded his head. The officer then lifted up Tom’s head and looked at the black eye and swollen nose. The officer then stood up and keyed his radio. “I have a minor who was beaten by his father and thrown out of his house. Black eye and maybe a broken nose. I don’t know if there are any further injuries but he has a bump on his head, so he may have a concussion. He’s at a friend’s house. I think he needs medical attention.”

Two more officers and a child welfare officer arrived, followed by the fire department ambulance. One officer stayed to write up a report and the others left with the ambulance.

“What’s going to happen to the kid’s father,” Mr. Glynn asked the officer.

“Can’t say,” the officer said, “Someone else will make that decision.” When he was finished with his report, he thanked us and left. Shortly thereafter Mother and I returned home.

***

What happened to Tom was very unsettling. While I didn’t mind talking about it with Joe and Mother, I didn’t want to talk about it with anyone else. I felt that it was like betraying a confidence. Keeping quiet about it was a real struggle. On Monday, the whole school was buzzing about it. What I heard from some of the kids was nothing like what really happened, but I took no steps to correct any misconceptions.

On the next Saturday, I was at Sue’s house, just enjoying each other’s company, something I really liked to do. After a while, she said, “Remember the Valentine’s Day party? Do you remember a boy named Fred?”

I could hardly forget, given what happened to Tom.

“He was hanging around with your friend Tom,” she said. “You might remember that Fred goes to my school. Well, somehow word got out that Tom and Fred were fooling around with each other, if you know what I mean, and some homophobic bullies dragged Fred into the locker room and really beat him up. I heard that Fred had to go to the hospital. Fred hasn’t been back to school since, and someone said that his parents pulled him out of school.

“What happened to the bullies?” I asked.

“The haven’t been back to school either, maybe they were suspended or expelled, or maybe, I hope, they’re in jail.”

The thought of what had happened sent chills down my spine. If some one had connected Christine with Christopher, the same could have happened to me. Boy, I thought, have I been naive, and I vowed to be more cautious in the future.

I wondered what had happened to Tom. No one had seen him or heard from him since his Father beat him up and kicked him out of the house. I really began to hate his Father. Two young lives ruined.

It was some time later that I found out that Tom’s Mother had moved away, and took Tom with her. I suspected that it would be a long time, if ever, before I heard from Tom.

***

In mid-April I turned fifteen, although it was no big deal. I was still too young to be able to drive. For dates with Sue I had to get someone to drive me or take the bus, which wasn’t too safe at night.

One time, Mother suggested that Emily drive for my date with Sue. I didn’t like the idea, and told Mother. Emily just sneered. “If you don’t want me to drive, I guess you’ll have to use some pixie dust and fly, Tinkerbell.

To celebrate my birthday, my parents ordered pizza and bought a store made sheet cake. Both were okay, but only okay, not great.

After the traumatic events of the spring, I appeared to be less anxious to transition, a fact which was not lost on my counselor, a result of which was that nothing was done, one way or the other. In fact, I was anxious to transition, but now I was scared.

One day, Sue and I were looking at a book about movies, and she paused at the page describing the movie “Tootsie.” Can you imagine a guy wearing a dress and makeup?” she asked. “I mean, could you?”

I hadn’t planned to tell Sue about my cross dressing quite yet, but here was a question that needed me to answer. “Well, actually, yes.”

“What!” she exclaimed with surprise.

“I wore a witch’s costume for Halloween last year,” I admitted, intentionally omitting any mention of other cross dressing.

“You mean with a dress and makeup, and all that?” she questioned.

“Yes, all that,” I answered. “The Mother of some of the kids for whom I sit had put together a witch’s costume. A long black dress, with long sleeves and high neckline, along with a witch’s hat.” I left off any mention of what I wore under the dress or that it had a long slit up the left side.

This talk of cross dressing piqued Sue’s interest. “I wish I could have seen it,” she said.

Nothing was said as she examined my hair, face, and body structure. At last she said, “Yes, you could pull it off, and wear a dress and makeup.” Another pause followed as she considered what she said next, “Could I see you in a dress and makeup?”

“A bad idea, given what happened to Tom and Fred.”

“Yeah,” she agreed, “but if we could do it somewhere private.”

“Private places are in short supply,” I commented.

“Where did you put on the witch’s costume,” she asked.

“At home. I had to have Mother’s help,” I rejoined.

“Then we could do it there.” she suggested.

“Then there would be a problem, my sister Emily.” I advised her

“Why? She could help,” she said.

“Her kind of help would be more of a hinderance than help,” I responded, “she would probably have a lot of ideas, all of them bad, and some worse than others.”

She didn’t let it drop. “Still, a little mascara and lipstick . . .”

“No,” I said, trying to bring this conversation to an end.

***

A week later, Sue was visiting me at my house. Her visit was Mother’s idea, probably to see if Sue was suitable daughter-in-law material. Of course, Emily inserted herself in the conversation.

“Chris was telling me about his Halloween costume,” Sue mentioned to Mother.

“Oh yes, it was a great costume,” Mother said. I noticed that Emily had started to giggle.

“What’s so funny?” Sue asked, not quite understanding.

“Oh, the dress was great,” answered Emily, “It had a big slit up the left side, coming up to here,” she added, pointing to mid-thigh on her leg.

Before I could object, Emily continued, “But that’s not the best part. Ask him what he had on underneath the dress.”

“No! Enough! I’m sure that Sue doesn’t want to know,” I complained.

“I’m sure she does,” countered Emily. “Well, if he doesn’t want to tell you, I will.”

“Mother!” I complained, “tell Emily to shut up.”

“Given Chris’ objections, I’m sure that you now really want to know,” crowed Emily, “a black slip with four inches of lace at the hem, and long enough to be visible under the slit. Oh, we can’t forget the black pantyhose and high heeled boots,” Emily added with a smirk.

By now I was beet red, half from embarrassment and half from anger at my sister.

Emily was not finished. “Even if we couldn’t get the witch’s costume, Tinkerbell and I are about the same size, and I’m sure that I could find a dress which he could wear.”

“Tinkerbell?” questioned Sue, and the whole ugly story of why Emily called me Tinkerbell had to be brought out, over my strenuous objection.

I was ready to explode by the time the conversation was over.

Later, Sue told me that she would like to see me in a dress, “It would explain some things,” she said.

“Like what?” I challenged.

“My friends have said that you are a little effeminate. I’d like to see how feminine you’d look in a dress, with pantyhose, high heels and makeup.”

After this disaster of an afternoon, I was sure that my romance with Sue was over, but she assured me that it was not. “I kind of like effeminate boys,” she explained, “That was one of the things that initially attracted me to you.”

***

Sue and I continued to date through the end of the school year, after which he parents sent her to an art camp. While there, she fell in love with a “Hunk,” as she said. Our parting was more or less amiable, but she said that she had changed her mind and she wanted a man who was more “Manly.” I was hurt, but not to much, because I could not see where our romance was going.

My Mother wanted to console me. “There are lots of girls out there for you. You’ve just to get over your shyness a bit, and you’ll find another girl. After all, you’re only fifteen, way too young for a serious relationship.” She was right, but I wondered whether I really wanted another girl

Another positive: with the breakup Sue didn’t get to see me wearing a dress.

Joe thought the breakup wasn’t a bad idea. He reminded me of a Samuel Butler quote: “It is better to have loved and lost than never to have lost at all.”

The Babysitter - Part 5 - Conclusion
By Pentatonic

After the incidents with Tom and his friend Fred, I decided that I had to be careful. I had acquired a girlfriend and, other than babysitting jobs, I did not appear outside in feminine attire. This was protective camouflage; to the outside world I was just a regular teenage boy.

Memorial Day is an exciting time for me. That is the weekend the community pool opens, and there are Memorial Day picnics. I had to decline an invitation to a picnic with the Bensons, because I wanted to be very careful of who saw me wearing a dress or skirt. Because the Benson’s daughters had only seen me as a girl, I couldn’t magically show up as a boy. However, Joe’s church was holding a picnic, and Joe invited me to attend.

“If I go to your picnic, it’ll have to be as a boy,” I told Joe.

“No skirt? Huh?” he answered.

“No. All the people who were at the Valentine Day party saw me as a boy. Heck, I’m even dating a girl I met there. It wouldn’t work. As a matter of fact it might be dangerous,” I explained.

Emily, true to form, was a royal pain. “Ooh, Tinkerbell has a date to a picnic,” she declared when she found out. “I’ve got a pair of hot pink short shorts you could borrow,” she added.

“For your information, it’s not a date,” I responded, “and I’m not going to wear any short shorts, no matter what color.”

“So Joe’s going to wear them,” she teased.

“No one is going to wear them. You’re just jealous because you’ll spend the Holiday sitting around the house all the time I’m at the picnic.” I had her there. She had just broken up with her latest boyfriend, and no one else had stepped up to fill his place.

“I’ll tell you what,” I added, “I’ll let you drive me there.” Emily had her driver’s license.

“I’m not taking you anywhere if you’re not wearing a dress or skirt,” she said.

“Mother!” I complained, “Emily’s being difficult.”

“Emily,” Mother said, “if I tell you to give Chris a ride to somewhere, you’ll do it, or else you’ll lose your driving privileges.” With this, I stuck my tongue out at Emily. I would have asked Mother to tell Emily to stop being difficult, but I knew that the chance of Emily stopping being difficult was like trying to keep the sun from rising in the morning.

***

The picnic, while nice, was nothing special. I had brought a German potato salad, and there was a lot to eat, including a plethora of pies, At least I ate well. The entertainment was home grown; someone had set up an electric keyboard, and members of the choir sang old favorite hymns. Because I can play the piano and like to sing, I found this enjoyable and softly sang along with them. But not too softly, because the Pastor heard me. “Do you need another singer?” he asked the choir in general. They did, because I ended up singing with them. During a break, I sat down at the keyboard and played.

“Not only does he sing, but he also plays the piano,” the Pastor exclaimed, “how about joining our choir?”

“I’ll think about it,” I said.

While at the picnic, a girl came up to me. “You’re Sue’s boyfriend, aren’t you?” she asked.

“Yeah, I guess so.” I replied.

“I don’t see her here,” the girl said, “How come?”

“Her family had somewhere else to go, and I’ve got a babysitting job this evening.” I said.

“Oh,” she said, “If you two break up, give me a call,” and with that she gave me a slip of paper with her name and number on it.

As it turned out, Sue found a new love at art camp, and when she came back home, she dumped me. Hardly a newsworthy item, but this girl, Cathy Samuels, heard about it and didn’t hesitate to call me. Emily likes to be close to the phone and answer it. When Cathy called, Emily announced, “Hey, Tinkerbell, there’s a Cathy on the phone for you.” Thankfully, Cathy didn’t hear what Emily said.

“I hear that Sue dumped you,” Cathy said. That’s quick, I thought, Sue only did it a few days ago.

“Yeah,” I responded.

“How come?” Cathy asked.

“I don’t know what Sue might have told you or your friends, but she seems to have found the new love of her life at art camp. What did she tell you?”

“Pretty much the same, and that you are shy around girls, inexperienced, and a little bit effeminate,” she answered.

“Does that bother you?” I asked.

“Not in the least,” she said. “I’d kind of like to be with a boy who can connect with his feminine side, because I think he can understand me better than some macho hunk.”

“Well, as you know,” I admitted, “I’m a long way from being a hunk.”

“So, when are we going to go out together? How does Saturday sound?” she said. Wow, I thought, I’ve just had a girl ask me out for a date.

“Sounds good to me,” I replied, “how does miniature golf sound to you.” It sounded good to her, and we spent some time just talking, like boyfriend and girlfriend.

All during my conversation with Cathy, Emily hung around like a vulture. “Ooh, sounds like Tinkerbell has a date.”

“Mother,” I called out, “tell Emily to mind her own business and leave me alone.”

“Emily,” Mother said, “leave your brother alone.” As expected, this had no effect on Emily.

“But Mother,” Emily whined, “It’s not fair. Sue dumps him, and a week later some hussy calls and he has a date. When I dump someone, it takes me weeks to get another boy to ask me out.”

“That’s because I’m not only prettier than you, but I’m nicer,” I rejoined, “and Cathy’s a nice girl, not a hussy.”

“Maybe you’re prettier when you wear a dress,” Emily replied. “By the way, does that Cathy know that you like to wear dresses and skirts,” she said with an evil look on her face.

“No, and she’ll never know!” I insisted.

“We’ll see about that,” Emily said to herself.

I had just about my limit of Emily’s teasing, and I complained to Father. This brought some results. “Emily,” he stated, “this teasing has gone too far. There is a line between friendly teasing and plain meanness, and you’ve pole vaulted over that line. Someone might hear your snide comments and put Chris in physical danger. It will stop this instant, or there will be severe consequences to you.” Dad listed some of the consequences he would impose for any breach on the part of Emily.

***

One day after a swim at the pool Joe and I were walking home. “What is it about you and girl friends all of a sudden?” Joe demanded to know.

“You ever heard the expression ‘hide in plain sight’?” I said, “after what happened to Tom and his friend, I’m just trying to fit in with the other guys who have girl friends. No one will know that I’d rather be a girl, not if I’m dating girls.”

“But what about us?” Joe asked.

“You’ll always be my closest friend,” I replied. “I just want to keep things cool.”

After a minute of silence when Joe and I digested what had been said, I said, “Cathy has a friend, maybe you could ask her out and we could double date. Cathy and I are going to play miniature golf on Saturday, and it would be a lot of fun if you and Cathy’s friend could join us.” Joe took my advice and we set up the double date.

***

It was shortly after the double date that I mentioned to Cathy that I was thinking of going to the community pool. “I usually ride my bike to the pool. If you have a bike, maybe we can meet there,” I suggested. When I mentioned this to Mother, Emily had to butt in. “You could borrow my string bikini,” she said, “but you’d have to find something to put in the bra.” I ignored her as well as I could, and reminded her what Dad had said.

When I met Cathy at the pool, she was the one wearing a string bikini that left nothing to the imagination.

When it came time to go home, I decided that, as a gentleman, I would escort her to her house, and go home from there. When we arrived at her house, there was no one home. There was a note on the kitchen table, directing Cathy to take a casserole out of the refrigerator at a particular time and put it in the oven. “They won’t be home for hours” she said, as she led me to the couch. We were sitting close to each other, with her arms around my neck. I could feel her breasts against my arm, and we kissed, long, lingering kisses, but nothing more. About an hour and a half later that she suggested that I go home, so I wouldn’t be there when her parents returned. I rode home, savoring the afternoon.

***

It was later in the summer that my counselor noted that my puberty was starting. “You’ve told me that you’ve been dating girls since the spring. Do you still want to become a girl?” she asked. I assured her that I did, and that my dating was to hide this fact from the world. I’m not sure that she believed me/

“Well, then we should talk about hormone therapy,” she said, “there are several different hormones, and each preforms a different function. For starters, we could try a testosterone blocker and some form of estrogen and progesterone. If you do, you will notice some changes in your body. You probably will like it that your breasts will start to grow. The down side is that you will have mood swings, and it is possible that you will develop a severe case of acne. There will come a time when it will be difficult to hide the changes from your fellow students and the rest of the people you know. As I told you before, gender dysphoria in males may just end all by itself when the individual goes through puberty, and we want to rule that out.” Since I was dating girls, I suspected that she might believe that I didn’t want to transition. She just didn’t seem to understand that I put personal safety way ahead of everything else and my dating was a facade to keep me from getting beaten up.

The end result was that I would have to wait some time before starting hormones, to see what was going on in my body. I wasn’t happy about this, but the simple fact was that they had the power to prescribe the hormones, and could withhold those prescriptions.

***

Ever since the beautician had given me a pixie haircut I had devised ways to make it look more or less like a boy’s haircut. Maybe less rather than more, because one afternoon after swimming, Cathy and I were at her house. “Let me dry your hair,” she said.

“No, that’s all right, it’ll dry all by itself,” I responded, but my protestations had no effect and Cathy went to her room and returned with a blow dryer, comb and hairbrush, with which she attacked my hair. The end result was that she returned my hair to the pixie hair style.

“Wow,” she said when she was finished, “you’ve got a pixie hair style, did you know that?”

“No,” I lied.

With that she turned and stared directly in my face. “Did you know that you have a pretty face?” she asked.

“I’ve heard something like that a couple of times,” I admitted. It was a whole lot more times than a couple, but I didn’t want to disclose that.

“With a little makeup, you could be a pretty girl,” she observed. While I knew that well, this was the last thing I wanted to hear from Cathy. I hoped that she would drop the topic, but to no avail. She called her mother over to look. “Mom, look at Chris,” she said, “don’t you think with a little makeup he would look like a pretty girl?”

“I don’t know,” her Mother replied, “Maybe, but I’m not sure that Chris would like that.”

“Oh, come on,” Cathy continued, “let’s try it.”

“I don’t want to,” I protested.

“Look, no one will know. After you get a look at yourself we can wash it right off,” she said.

“And put my hair back the way it was,” I demanded, not realizing that by what I had said I was admitting to allow Cathy to apply some makeup.

When Cathy’s mother saw some makeup being applied, she said, “I didn’t think that Chris wanted you to do that.”

“He said it was okay, as long and I put his hair back as it was,” Cathy said, taking a very liberal interpretation of what I had said. Cathy left and returned with a mirror. The reflection of my face was nothing new to me; it was what I had seen countless times before when I made myself up.

“Mom, come over here and take a look,” she said.

“Very nice, dear,” her mother said without commitment and with some reserve in her voice, “but Chris can’t ride his bicycle home looking like that.”

“Could you take it off now, and put my hair back like it was?” I asked.

Cathy didn’t answer my question, but rather said, “I bet you’d look great in a dress, with some jewelry.”

I was really nervous by now, and quite unhappy, and again requested she undo what she had done.

“But I like the way you look right now,” she said. She then put her mouth close to my ear and whispered, “I like girls as well as boys. With you I can have both.” Alarm bells went off in my head.

A few days later, Cathy suggested that we go to some kind of meeting on the next Wednesday evening. “I hope not too late, I don’t want to be alone on my bicycle in the dark,” I advised.

“Mom can pick you up and drive you home,” she suggested, “how about it?”

“I guess that it would be okay,” I admitted.

That Wednesday evening Cathy’s Mom drove us to a local church. The first thing I noticed was a rainbow-colored banner above the door. “Is this an LGBT meeting?” I said with some concern, “are you . . .”

Without waiting for me to finish that sentence, she said, “Yes, come on, it won’t hurt you.”

Cathy introduced me around as her new boy/girl friend. I didn’t like that at all, because I was afraid of what could happen if that was known at school, but I don’t think anyone considered me as anything other than Cathy’s straight boyfriend, no matter how she introduced me. I found out how often the meetings are, and stowed that information in my brain for future reference.

I was beginning to understand why she had told me she liked boys who had a feminine side.

***

One day at the pool I saw Cathy holding the hand of an older girl. They came over to me. “Chris, I’d like you to meet Sandy. Sandy and Cathy smiled at each other, and kept holding hands. A short time later, Cathy pulled me aside. “We need to talk,” she said, “Chris, you are very nice, and I like you, but I’ve met Sandy, and I don’t want to continue to date you.”

Wow, I thought, dumped again, but this time for a woman. Oh well, time to find a new girlfriend to keep up the facade of being just a ‘regular guy’ as protective camouflage.

Finding a new girlfriend did not prove difficult. Anita latched on to me when she heard that Cathy and I had broken up. At first she seemed to be sweetness and innocence, but that was her facade. Underneath it she had the morals of a female alley cat. A few weeks later she met a male alley cat, and that was that. Dumped again.

A short time later I had a babysitting job for Ellen, Mrs. Sloan’s daughter. Sylvia was there when I arrived.

“How’s your love life as a teenaged boy?” she asked, knowing of my facade.

“I’ve been dumped three times,” I related, “once for a ‘hunk,’ once for a woman, and a third time for a guy with the morals of an alley cat.”

“So, no lasting romances?” she asked.

“No, I guess not,” I replied.

“You know why?” she asked.

“No, not really,” I answered.

“Did you sleep with any of them?” was her next question.

“No, of course not,” I said, almost indignantly.

“There’s your answer,” Sylvia said, rather smugly.

***

It was August when Virginia entered my life. She and I were in school together and shared some classes. I had the impression that she was shy, because I never saw her hanging out with any boys. I was at the pool with some of the guys, and she had come with a group of girls. Naturally, a group of guys are drawn to a group of girls like flies to honey. I took a chance and asked, “Are you taking the music history course this coming year?”

“Yes,” was her one word reply. It took a lot of talking to get her to respond in complete sentences. Later that afternoon one of the other girls pulled me aside. “Virginia told me that she likes you. She said that you’re not a macho boor like most guys. As you may have noticed, she is rather shy. I’ve heard that she was abused by some weirdo when she was little, and as a result she is afraid of boys.”

Virginia and I found that we had a lot in common and she began to warm up to me. We talked about music and dancing, and we found that we both liked ballroom dancing. I had learned it when Emily took some dancing classes, and I was asked to attend since the classes did not have many boys in them.

“My Dad is a member of the country club, and they are having a ‘Founder’s Day’ dinner dance coming up,” she said one day. “Dad asked me if I wanted to invite someone, and since there will be a lot of ballroom dancing, I thought of you. Would you like to go with me?”

While I was surprised, I readily accepted.

While the dance was not formal, all of the men wore coats and ties and the women wore cocktail dresses. Some of the women even wore formal gowns. I danced with Virginia, and then with her Mother. After her Mother and I returned to the table, her Mother exclaimed to all, “He knows how to fox trot, waltz, and can do the rhumba.” It appeared that a lot of the men did not have these talents, so I ended up dancing will all of the ladies at the table.

I had noticed that when I held Virginia while dancing she seemed to stiffen up. I surmised that this was a reaction to when she had been abused and she was afraid of men. However, the more I danced with her the more relaxed she became. As everyone was leaving, Virginia’s Mom pulled me aside. “Chris, we really enjoyed your company, and Virginia seems a lot more relaxed with you than with any other boy,” she confided. I had found a new girlfriend.

***

When school started, I found out that all of my class would have meetings with the guidance counselors at the school. All of us had to fill out a questionnaire to help determine what careers we might like, and this was used to schedule our classes. In addition to the questionnaire we were scheduled to meet with a guidance counselor.

“I’m impressed with your academic record,” the counselor said, “I hope that you are thinking of going on to college, in which case I think that you should look into available scholarships.” He looked at the questionnaire. “You say you are interested in a career working with children. Why is that?”

“I’ve done a lot of babysitting; I enjoy it, and making it enjoyable for the children,” I responded.

“Hmmm,” he responded, “what do you think about teaching?”

“Or maybe working in the healthcare field,” I added.

He consulted a list on his desk. “I don’t know if you’d be interested in this, but St. Luke’s Hospital here in town offers a scholarship for people in the area who want to get a nursing degree. They’ve paired the scholarship with Morgan University, which is also in this town.”

He paused for a moment, and consulted some information on his desk. “Oh,” he said, “I don’t suppose that you know any doctors. It says that you have to have a doctor sponsor you.”

My mind immediately thought of Virginia’s Dad. He’s an MD, I thought. “I might just know a doctor who might just sponsor me. Of course, the operative word is ‘might’ in this case,” I said.

The counselor handed me a sheet of paper. “Here are some of the details of the program, take a look at it and ask to see me again if you are interested.” With that the session ended.

***

Some time later I was invited to a barbeque at Virginia’s house. I have always been comfortable talking to adults, and Virginia’s Dad asked for a minute of my time. “You’re a bright and personable young man. Have you thought of a career?”

“As a matter of fact, I have,” I started to say.

“How are your grades?” he interjected.

“Pretty good, Not straight A, but a solid B+ average.” I responded.

“How about science?” he asked.

“All A’s,” I said.

“Before I interrupted you, you were going to tell me about your thoughts for a career,” he said, in the nature of a question.

“Funny you should mention it, but I recently had a conference with a guidance counselor, and he told me of a scholarship program at St. Luke’s to get a nursing degree,” I advised him.

“Maybe unusual for a boy, but not impossible,” he commented, “in fact, the scholarship committee was considering ways to attract young men into nursing. I should know, since I am on that committee.”

Bingo! I though. If I play my cards right, this may actually work. I smiled to myself.

Virginia and I continued to date, but the relationship never progressed beyond a few chaste kisses, which was perfectly fine with me and Virginia. One real benefit was that the more time I spent with Virginia, the closer I became to her Father.

After a dinner at Virginia’s house, her Father turned to me and asked, “Does your school have career days, where you follow someone for a day, to see if you’d like to do that as a career?”

“Yes,” I answered.

“Let me talk with the Director of Nursing about this, and I’ll get back to you,” he said.

“Thank you,” I responded.

Virginia’s Dad, as I later found out, was quite an important person at the hospital, because a few days later the Director of Nursing, in person, called me. We set up a day for my visit. “Come by my office some time this week so you can sign the necessary papers and I can get you a set of scrubs to wear.”

I really enjoyed learning what nursing was about. What impressed me was how much hard work it was.

***

Although it was only the start of my sophomore year in high school, I had set my goals. The first was to win the St. Luke’s Hospital scholarship and get admitted to the nursing program at Morgan University. The second was to get some progress on my transition. I had been successful in concealing this second goal from just about everyone, which I believed was necessary for my personal safety.

My first goal required that I keep my grade point average as high as possible. My dating of Virginia was a definite plus in this endeavor. Virginia and I shared a number of classes, and we were able to study together. Joe also shared many of these classes, and on weekends the three of us could be seen doing class work together. Obviously, social activities were not as important.

When mid-term grades were sent out, our diligent work was rewarded. The same cannot be said for Emily’s grades. She had come to realize that her grade point average was below what was needed for admission to a good college, but since she was a senior, now was too late to do anything about it.

As to my second goal, I had convinced my counselor that I was serious, and I started on a testosterone blocker. I told the counselor, again, that my dating was strictly for self preservation.

When Halloween rolled around it was pretty much just another day, except for taking Ann around for trick or treating. This year I did not wear a costume, much to the dismay of Emily and Joe. I told them that they just had to learn to live with it. I did keep babysitting, because I needed the money.

The holidays, and in fact the whole next spring, were unremarkable, except that I now had a driver’s license and could get a job. All of my studying had the desired effect, and at the end of my sophomore year my grade point average had improved, as did Virginia’s and Joe’s. Naturally, the study time cut into my social life, and most of my dates with Virginia were study dates.

***

When summer was nearing, I began to think about getting a summer job. As can be imagined, there are more teenagers looking for jobs than there were jobs. Here my connection with Virginia’s Dad helped me.

Virginia would not be looking for a job, since she had enrolled in a summer program at a college which would earn her college credits. The college was in another state, so Virginia would be away the entire summer. Naturally, neither Joe nor I could afford to do the same.

It was a Sunday afternoon in May, and Joe and I were at Virginia’s house, studying. Virginia’s Dad came into the room when we were taking a break. “Chris, Joe, what are you thinking about doing this summer?” he asked.

“Both of us are hoping to find a summer job,” I answered, “and I will keep babysitting.”

“The reason I asked,” he continued, “is that I’m impressed by the two of you. I talked with the facilities’ manager and he said that he could find summer jobs for both of you. They will be minimum-wage, unskilled jobs, like mopping floors or hauling trash, but they are available if you are interested.”

We were very interested, and interviews with the facilities manager were arranged. Joe and I were hired.

My camouflage remained intact. I was a brainy kid, whose girl friend was away for the summer, and who was lucky and had landed a summer job. The net result was that I was totally ignored by the other kids, which just suited me fine.

Joe’s plan was to earn enough money to buy a car and pay for insurance, and in mid-August he reached that goal. The car looked like a junk yard reject, but it ran, and got us where we wanted to go. Neither Joe nor I had taken any auto repair courses in high school, but some of the men with whom we worked knew about cars, and even took some time out to help us with keeping it running.

It appeared that Joe had an ulterior motive in getting the car. “Hey,” he said, “you could put on a nice skirt and blouse and we could drive to a secluded spot and play kissy face and huggy bear.” I made a face at him when he suggested this, even though I inwardly would enjoy it.

“In your dreams,” was my response.

***

The course work for my junior year was harder than it had previously been. Just to keep up required a lot of work. Since Joe and Virginia shared a lot of classes with me, they had to work just as hard.

My sister Emily was not admitted to any of the colleges to which she had applied. It was suggested that she enrol in the community college where they had what could be best described as remedial courses. My course work was well above what she had to learn and she was forced to come to me, hat in hand, for help. Payback time!

“Hey Chris,” she would say, “can you help me?”

“So now it’s Chris, and not Tinkerbell?” I asked.

“I’m sorry for being mean and teasing you about that,” she was forced to admit. I could see that she was at least a little sorry, so I agreed to help her.

***

Throughout my junior year, I had little opportunity to wear a skirt or dress, other than my babysitting work. Since Joe had a car, there were occasions where I would get dressed and Joe and I would drive to another town where it was not likely that Joe or I would be recognized. Naturally, I had to arrange these trips when they did not conflict with my social life with Virginia and my babysitting jobs. These occasions were few and far between.

***

The next summer, Joe and I were able to get the same jobs we had the prior summer, and we were saving up for college. As soon as I could, I applied for admission into the nursing degree program at Morgan University, and made application for the scholarship offered by St. Luke’s Hospital. My time spent with Virginia’s Dad paid off and he sponsored me.

Right after the first of the year, I began Hormone Replacement Therapy. “You know,” my counselor said, “you will begin to see the effects of the therapy, some sooner and some later. You probably will like it when your breasts enlarge and you will have some fatty deposits compatible with females. However, you will need to be patient.”

When I related this to Joe, he was ecstatic. “You mean that you’ll be getting tits?” he exclaimed, “can I be the first to fondle them?”

“Is that all you think about?” I challenged.

“Well, maybe not the only thing,” he said, “but I do think about it a lot.”

“I had hoped that as you got older you might mature some,” I rejoined.

“Not a chance,” was his response.

***

Shortly thereafter my counselor and I discussed my Real Life Experience, where I would present myself as a female full time for a whole year. I told her that I planned to start my RLE right after I graduated from high school.

“You know, if you plan to have gender reassignment surgery, I will not approve it until some time after you have completed your RLE,” she advised me, “Have you thought about how you will handle things when you are in college?”

Now there was the rub. If I was accepted at Morgan University, it would be as a male. Same for the scholarship, if I got it. If I didn’t get the scholarship it would be moot, since I couldn’t afford the tuition without it, even living at home. In any event, I couldn’t address the problem until I was accepted and had the scholarship.

Fortunately, I had joined a support group for transgendered persons. Other members of the support group had faced the same issues, and some were successful in solving the problem.

***

I knew that I would have to tell Virginia what was happening in my life. Therefore, I made plans to take Virginia out to a fancy restaurant for Valentine’s Day.

“We’ve been dating for a long time, and I am very fond of you and the time we’ve had together,” I said, “There are a lot of people who think that we should get married. However, there is a little matter which might make that impossible.”

“Chris, I am very fond of you, but don’t you think that it is a little premature to talk of marriage? We are both looking at college, and I for one anticipate that I will want to go to grad school,” she responded.

“The matter I’m talking about has nothing to do with college or grad school,” I said, “but before we talk about it, tell me if you love me.”

“As I said, I am very fond of you,” she answered, “but in love with you to the extent that I want to marry you? No.”

“That makes it easier for me to tell you about this matter. Virginia, I’m transgendered.”

For a minute, neither of us said anything.

“You mean that you want to be a girl?” she asked.

“Not quite,” I answered, “for a long time I’ve known that I am a girl, but in a boy’s body. I’ve started on hormone therapy, and right after we graduate I will dress and act as a girl, full time.”

“Oh,” she said, “that kind of rules out marriage, even after grad school.”

“Yeah,” I agreed.

“Who knows about this?” she asked, and I told her.

“You know, I think you need to tell my parents, especially my Father,” she observed.

“Yeah,” I agreed, “I think that I have to.”

She smiled. “I know it’s not funny, but I was just thinking of what my Mother will do. I think that she was sizing you up as a son-in-law. I think that Dad will be more understanding. After all, I have told both of them that while I really like you, I’m not in love with you. I’m not sure that they believed me.”

She paused. Then she said, “You want to know why I’m not in love with you?”

“I guess so,” I answered.

“I’ve always thought that you are a bit too effeminate.” She chuckled. “Now I understand why.”

“By the way, I’m not letting you off the hook,” she added, “as of now you are no longer my boyfriend. You are now officially my best female friend. I want to keep seeing you as before. Is that okay with you?”

“More than okay,” I answered, “it’s more than I could hope for.”

***

I dreaded meeting with her parents, but I knew that I had to. I steeled my courage, and told her Dad first. “Well,” he said, “That is some revelation. I need to digest that. You know, it will affect your application for the scholarship, but we might be able to deal with it. Let me think about it and discuss it with the committee. Why don’t we plan on having dinner next weekend? By the way, what name will you be using?”

“Christine,” I replied, “it keeps things easier.”

***

In due time, Morgan University advised me that I was accepted into the nursing degree program. I scheduled a meeting with the director of admissions, where I told him of my upcoming transition, and asked him if I could still attend the school. He said that I could, and that I was not the first person to do it, and they had a policy established to make it happen.

About a month later, I was advised that St. Luke’s was awarding me the scholarship. Thereafter, Virginia’s Dad arranged a meeting with the scholarship committee, and my award was amended.

***

At long last, graduation. I jumped the gun a little on graduation day and wore panties and pantyhose under my clothes for the commencement.

The next day I went whole hog and wore a dress. By this time, my breasts had began to grow, and the nipples and areola had become larger. I definitely needed a bra by now. Naturally, Joe was very interested.

***

Ever since I knew that I really am a girl, I wanted to marry Joe. Now, how to get him to propose? I decided to discuss it with Mother who couldn’t understand why I always wanted to hang around with Joe. I dressed in a ruffled blouse and skirt and sat at the kitchen table over coffee. I started the conversation.

“I want to marry Joe.” I said.

You could have heard a pin drop. After a moment she made some incoherent mumbles, and then said, more of a question than a statement, “You want to marry Joe?”

“That’s what I said,” I replied, “I want to be his wife.”

“When did you make this decision?” she asked.

“When I first discovered that I’m really a girl,” I answered, “maybe around fifth grade.”

“Fifth grade?” she said, with surprise in her voice. “You never told me,” she added, “why didn’t you ever tell me?”

“I didn’t know if you’d like it then,” I posited.

“I’m not sure I like it now,” she exclaimed. She paused. “Does Joe know?”

“Of course not, the prospective groom is always the last to know,” I said with a snicker.

“How do you plan to get him to propose?” she asked.

“Well, I’m not going to put on a short skirt, sit on his lap, and rub him with my butt,” I said.

“Seriously, how do you really plan to do it?” she wanted to know.

“You know how he always wants to see me in a dress. I’ll ask him if he’d like to see me wearing a bridal gown. He’s sure to say yes,” I explained. “I’ll steer the conversation around to see if he gets the hint.”

“And if that doesn’t work?” she questioned.

“Well, in that case, maybe I’ll put on a short skirt, sit on his lap, and rub him with my butt until he proposes.”

“You’re hopeless,” she commented.

“Really, I think that I’ll have to propose to him,” I said.

“Okay, I’m not wild about this, but tell me, when do you want to get married?” she asked.

“Maybe two years from now, after I’ve had my sexual reassignment surgery.”

At that point, Emily walked into the room, having just returned from a class. “Did you tell her?”

“I just did,” I answered.

“You told Emily before you told me?” she asked.

“Of course, sisters always confide in each other before talking to Mom,” I said.

“I don’t know if I liked it better when she was always teasing you,” Mother said.

“That’s over,” Emily said, “ever since she stopped being a snotty little brother and became my dear sister.”

***

It was time to clue Joe in. I put on a short skirt and revealing blouse, showing off my new breasts, with a little help from some rolled up pantyhose. I went over to his house, and I knew I had his attention the minute he saw me. “You like?” I asked.

“I always like it when you wear a skirt or a dress,” he answered.

“Then how’d you like to see me in a bridal gown?” I asked.

“I’d love it,” he answered, “When you going to show me?”

“Some time after you get on your knees and ask me to marry you,” I answered.

“You want to marry me?” he said.

“Yes,” I answered. “I’ve wanted to marry you since fifth grade.”

“You never told me,” he said.

“I couldn’t very well until now, could I?” I said

“I guess not,” he replied.

With that, he got on his knees and proposed and I accepted. He then sat next to me on the couch and began to rub my knee. He progressed further, and then touched my breasts. For the first time I had known him I did not stop him. After all, he was now my fiancee.

***

We were married six months after my surgery. Emily was my maid of honor and Ann a bride’s maid. He really liked my bridal gown. I gave Joe my virginity that night.