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.