Two boys discover they are more alike but never had let the other know. One boy is model of feminine attire the other boy just enjoys dressing as a girl and being with boys. The one thing the two boys discover is their affinity for each other.

 

The Model and the Cross Dresser

by Jill Micayla

 

I went over to visit my friend Jimmy, he had called and told me his parents were out of the house. I asked him if his sister was there and he told me she was gone for the next two weeks. I liked his sister Elaine, she and I had dated a few times but we never got beyond kissing at the front door. I rang the door bell and saw the curtain open and close, then the front door opened and I walked in. I began to turn when I saw a familiar dress behind the door. I was stunned to see my friend Jimmy standing there smiling. He told me that he had wanted to tell me he liked dressing as a girl but did not know if I would accept it. I stood there staring and then realized what he had said. I asked him if he liked boys as much as dressing like a girl and he answered he was not sure about the boys' thing. I told him that what eh did was his own business and since we were friends I did not mind as long as he did not ask me to wear his sister's clothes.

Jimmy said he had been dressing as a girl since he could remember and had done so without his mom and dad knowing. I asked if Elaine knew and he told me that she had caught him in her room in her bikini. He went on to tell me he usually went to the mall as a girl but today wanted to let me know that he was into looking like a girl. I told him that he almost did look like a girl to me, but that he still had that Jimmy sort of look. He thanked me and then we went to his room to play on the video game. I followed him up to his room and he did move like a girl and behind he looked like a girl

When he got close to me, I could smell the perfume and I looked at him closer and with more depth. Here was a guy I knew dressed in his sisters clothes. I was not sure if Jimmy was really a guy as we sat and played. He was terrible at the video games and the more we played the worse he got. I finally said that maybe if we just talked that would probably suit him better. I asked him about his sister. He told me that she was the one who suggested he begin learning what it was to be a girl. She taught him about cosmetics and hair styling. She encouraged him to spend hi allowance girls tings and they began to share wardrobes. He said he had double dated with Elaine before she started dating me. He said that he needed to be honest, he had lied when he was not sure if he liked boys more than dressing like a girl. He said that he had kissed each boy he dated and one of the boys wanted oral sex. Jimmy said he enjoyed making boys happy. I asked him about me, what about me was so different. He said I was his closest friend and that he was afraid I would hear about Elaine's cousin that was a slut.

I looked at my watch I needed to be home and told Jimmy he was very nice looking and before I could get to the door he came to me and put his arms around me and we kissed. I was supposed to be repulsed by the kiss but I enjoyed it and then we French kissed and I knew that I was going to have a hard time as a boy in a dress was turning me on.

I hurried home and began preparing dinner for my mom and sister. Once I had the potatoes on slow cooking, I placed the casserole in the oven and headed upstairs to change. On my bed was my newest dress. Mom had wanted Jolene and me to be twin sisters as we were fraternal twins. I had no problem with it and until a week ago I was really very comfortable with it. Jolene started dating and had suggested a double date. I put my foot down. My argument was I could never kiss a boy. I was unsure of why I was so turned on by kissing Jimmy and it was working on my mind.

I was dressed when mom and Jolene came in. Supper was ready shortly after that. Mom liked me to be in dresses as much as possible. She was a psychologist and her specialty was gender dysphoria. Mom told me that she thought it better to have me be a girl and to be a rowdy boy. She said that my friend Jimmy was one of those boys she did not trust. I had heard her tell me many times that Jimmy was up to no good. I wanted to tell her that he turned me on and I was not sure how to handle it.

When we finished dinner mom and Jolene did the dishes and I went top the living room to watch the news. I sat and pondered how Jimmy would react if I told him I was a boy who did not mind being in dresses and actually spent most of my time as a girl. I had developed breasts' thanks to moms insistence that I take hormones since I was nine. I was a teen model for a clothing manufacturer. I only modeled dressed and skirts. Jolene and I would often do twins in certain clothes, sometimes, and we would pose in bikinis'.

Mom noticed I was a bit quiet at the dinner table and she came into the living room and sat next to me. Being a caring mom, she asked me what was bothering me. I looked her in the eyes and tried to tell her and began to cry.

"Oh mom, it was horrible, I discovered I like kissing boys and I am so ashamed that I do."

"And how did you discover that kissing a boy was pleasant for you?"

"Mom, I went over to Jimmy's and he was dressed like a girl, I did not react and before I left to come home he came over and put his arms around me and kissed me." I was sobbing; " Oh mom, I did not want to kiss him but when our lips touched I wanted it to keep going, mom! I French kissed my best friend."

"What did Jimmy do?"

"I do not know I left to come home. I never even told him thanks you or anything."

"Don't you think you ow him an apology for just walking away, and it is about time you let him know that you make a living modeling girls clothes for a catalog?" She smiled at me. "Sweetie if he kissed you and did not react when you began to kiss him back he is probably doing what you are doing right now trying to figure out how you are going to tell him he turned you one."

"Mom, maybe I should invite him over and let him see me as Colleen and go for a walk to tell him I enjoyed kissing him."

I went to the phone dialed the phone number for Jimmy and when his sister answered I asked for Jimmy. I invited him over so we could talk, I told him that it was something we needed to take a walk with and discuss.

I made sure my makeup was correct and that I was not in disarray as I waited for Jimmy. Mom kidded me that I was just like a girl primping for a boy. She said that if she did not know better I was infatuated with Jimmy. I was blushing when she looked at me. She smiled that motherly smile and when the doorbell rang she went to the door and opened it. She greeted Jimmy and told him that I was in the living room.

Jimmy walked into the living room and called me Jolene. I told him that I was Colleen and he looked at me. He asked where Rick was and I said he stepped out for the evening and will not be back until school starts in the fall. Jimmy said he just got a call from Rick and I told him he was right, but Rick is not in picture and that maybe a walk will help him understand. Jimmy and I went out the front door and after we were away from the house I told Jimmy that I was his best friend who knew that Jimmy liked dressing as a girl. He looked at me and said there was no way I could be a boy. I asked Jimmy to kiss me and when we embraced and had kissed for a short time he suddenly stepped back and looked at me. He started to speak and I put my hand over his mouth. I told him to call me Colleen. He and I walked to the strip mall and got a soda. We sat in the park as we talked. I told him I had been raised as a girl and that one day I discovered I was a boy and began to wear boys' clothes. I was still a model and that I was a girl whenever I was not in school. I told Jimmy that when he kissed me I felt tingly all over and was startled that I liked being kissed by a boy.

Jimmy said that when he kissed me he felt different from when he kissed other boys and that he was trying to figure out why I was so different. I told him that was probably because everything I do is centered around being a girl. He reminded me I dated his sister and how was I going to tell her I was a boy who liked being a girl. I told him she already knew, she reads different glamour magazines and has seen me in many different catalogs. I told him Elaine never mentioned that he was into wearing girls clothes. Elaine had in fact given me an ultimatum a week ago, either sleep with her or she will find someone who will. I told Jimmy that I told her I was not going to sleep with her. I told him that the kiss certainly had me wondering about my own sexuality. I let him know that he could date me anytime he wanted and that I would be a good girl for him. Jimmy said he already had a boyfriend. He said that one of Elaine's class mates is gay and likes Jimmy dressed as a girl so they can go out and no one will know he is gay. I asked Jimmy how far he and his boyfriend had gone, Jimmy said all the way and he certainly was not ashamed that he was a girl who liked boys. I reminded him that if anyone in school finds out he may be in for a hard time. When I told him that I saw three guys from school walk by. Jimmy got a bit nervous and I asked him why. He said that one of the guys had suspected Jimmy of being gay. I told him to kiss me so that the guy would lose that thought. I kissed him as though we were serious lovers and when we were done the guys came over and asked who I was. One of the guys said I was Colleen Springer Jolene Springer's twin sister. He said eh read about us on the internet and that we were Hotties as models. The big guy said to Jimmy that he had thought Jimmy was gay, but if he is dating a top model than he had to be straight and said that he would leave Jimmy alone. Jimmy thanked him and the three left us alone to talk. Jimmy looked at me after they were gone "A model?' "You are a model of girls' clothes?"

"Yes, I am." I told him, " I have been modeling since I was a small child, I have modeled exquisite evening wear to lush lingerie."

Jimmy hugged me and said he would walk me home and talk to me in the morning. I told him Jolene and I had an upcoming shoot and would be leaving in the morning for two weeks. Jimmy asked if I was going to stay as a girl for the summer and I told him that until school started I was Colleen everyday twenty four seven.

We arrived at my house and I gave him a long kiss before we said our goodbyes. I had felt his hands on my buttocks and on my body as we kissed, when he got to my breasts he stopped and looked at me. I shook my head yes and we went back to kissing. When he left, I went inside and mom told me that she knew I was in love.

Jolene and packed our suitcases, we were doing a twin shoot and so we decided to wear opposite clothes when not being shot for the article. I loved pink and she loved yellow, we both liked periwinkle and satin was our favorite followed by silk for materials. We wore our hair the same even when we were dressed differently.

Jolene and I were better sisters than a brother sister, we would talk about boys and decide on our own scale who was a hunk and who was not. When we were on a shoot, we were chaperoned wherever we went. We were quite used to it and behaved ourselves so we would not be discovered as not identical twins. We were modeling string bikinis on a real beach and the shoot was taking longer than usual. When we finished for the day, we had sunburn and I was upset. I now had a bra line. I was to do a mesh one piece the next day and Jolene was to do a teal one piece. Either way we were going to be dressed we both had red that would stand out. We would be at the shoot for one extra week so we could tan.

When we arrived bak home, we had two weeks before school began. There was no way I was going to go to some boys gym class with the way I was. Mom met us at the airport and told us she had enrolled us in Heatherfield School for Girls. She told me since I had a boyfriend I needed to remain a girl at all times. Mom did not want a scandal. She told us we were going to Denmark for spring break and that when we were done we would be identical girls. I would have fought with her all the way a few weeks ago, but I was now enjoying being a girl. I was dating Jimmy and enjoying our time together. I went to some of his school dances and not only dance with him but several other boys who wanted to know me because I was a model.

Jolene and I had another busy summer coming up. We were going to the Carribean for almost three months for a special shoot. I knew that while we were there we would finally enjoy ourselves even more because we were both girls. Jimmy and I began dating even more, he found that he like me more as a girl and ahd quite going out with boys.

  

  

  

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