The Babysitter - Part 2

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?”


“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?”



“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.

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