From my earliest memory, I liked trying on girls’ things. My mom’s slips, sister’s panties, even my aunt’s nightie, (that is another story). I even went as far as dressing up completely when I was home alone. Mostly I wore my sister’s things. I loved her short shorts and halter tops. We were about the same size even though I was a year older. I didn’t necessarily want to be a girl, just dress up and pretend. I loved to feel like a sexy, pretty girl. But, of course I always hid it from everyone.
As I got to be a teen I stopped experimenting with these kinds of things. I met girls, and it seemed that maybe I shouldn’t be doing those things. I felt a little guilty inside. So, I stopped, though I still had an interest in doing it.
One day by chance, opportunity came knocking.
My girlfriend at the time was a little older by about two years; I had just turned sixteen at the time, and she was much more experienced than me. A very beautiful girl, she taught me so many things, including how to properly kiss. She was my first real kiss. She is the love of my life. We spent all our time together. We were inseparable. Sometimes we even hung out with her girlfriends.
One day, she and her friends were all doing their nails and she suggested they do mine. I was kind of excited but wanting to appear more masculine, so I resisted. Finally, though, I gave in. She and her two friends laughed at me, but I enjoyed the pink glittery polish on my nails. My girlfriend gave me extra hot kisses for complying later that evening.
Over the next days, I admitted to her, as did she to me, that we enjoyed doing my nails. It made me feel pretty. She admitted she had always had a thing for androgynous looking guys. She even encouraged me to let my nails grow out long. We evolved into make-up and doing my hair, which was very long at the time, to look as feminine as possible. I felt pretty with make-up, my sexy long hair curled and my nails painted and long.
We shared lots of sexual thoughts and fantasies during this time and I admitted I used to try things on when I was younger. She decided to see how far I would go.
She decided to dress me up completely. She and I were about the same size. I was so excited; of course I was shy and tentative about it, and even scared, but inside I wanted to try it so much. During my teens, I was very thin. 5′ 7″ and about 130lbs or so, twenty-seven inch waist. We started slow. Girls’ skin-tight jeans, peasant top, sandals. All done up I looked pretty and not at all like a guy. I was thrilled. We made out so hot; she loved it.
One day she suggested we go to a movie. I was dressed similar to the first time. Nothing that would attract attention. No one noticed I was a guy. I felt so pretty. She called me Michele. We were like best girlfriends when she had me dressed up.
Over the next few weeks, we played dress-up more and more. She thought I was very convincing as a girl. Eventually she even started dating another guy. An older guy. A very hot older guy. She promised me it was just for dates. She said she needed to be with a strong masculine man sometimes. But she assured me that she loved me. I was not happy, but I accepted this as part of our relationship. I felt I had no choice.
Finally, after a few more weeks of experimenting, she challenged me to dress up super slutty with her one night and go to a party so we could see if I would pass. I protested strongly, I was very scared of being found out. I wore a very short denim miniskirt, black off the shoulder 3/4 length sleeve tee shirt that let my smooth tummy peek out and very, very tall black heels. A pretty pink string bikini panty under. Makeup, sexy pink nails hair curled long and flowing. My girlfriend wore tight white slacks, a pretty pink top and sandals.
I felt like everyone would know I was a guy. But, no one let on at all. Some guys even flirted with me. But still I was so scared. I danced with my girlfriend a good bit. She danced some with other guys, but I tried to avoid dancing. I did have one older guy, like twenty-two, pressure me in to one dance, he was a college guy. Slow dance. His hands were all over my back and bottom, he even kissed my neck. I felt so turned on. No one could tell I was a guy. But, there was no one there that knew me as a guy so I felt that was the difference.
My girlfriend pushed me harder and harder to dress up slutty and practice in my heels. We did something almost every day. Even went shopping. She liked having a boyfriend that was also her best girlfriend. We loved making out stopping short of going all the way. I wanted her so badly, but she would not let me fuck her. I loved dressing, experimenting. I felt I was bi sexually, but romantically and emotionally straight and totally in love with her. She is the love of my life. I love serving her.
She had become more vocal in telling me about her dates. And I loved hearing about it. She loved his assertive kisses and said that she felt so good with him sexually. She was getting more adventurous. In a way it turned me on so much to hear about him and how he made her feel.
She wanted to dress me up for her friends to see if they noticed. This seemed very safe to me and I was excited to go along with it. We decided on white short shorts, flowered halter cropped top, tall pink heels, and white string bikini. I was totally made up. My girlfriend was so pretty in a yellow sundress and heels. Her three best friends came over. I was so nervous. They were there for about thirty minutes before my girlfriend asked if anyone knew me. They were all very uncertain, she looks familiar. But no one got it. Finally, she told them who I was. They seemed so surprised, lots of compliments. From then on, they did not see me as my former male self. I was totally accepted. I even got a few kisses. I loved being one of the girls. From then on, I was asked to go out with them, shopping, dancing, everything. I was totally Michele.
My girlfriend wanted to push things further. She knew my best friend Donny very well. She asked him if he would go on a double date with her and a guy she was dating along with a cute friend of hers. A blind date with a very cute girl. He agreed to go as he was always very outgoing and social. She was talking about ME!
When I found out, I was adamant I would not do it. For sure he would know who I was. She said she had told him that Michele was one of my cousins that she knew from a music class she was taking. She told me that would account for any resemblance. Oh my! I was so shocked! How could I do this? Not only is my friend very outgoing and social. He is known for being a make out person, a real stud. He is tall 6’ 3’’athletic and so very cute, he is also two years older than I am.
The night came and I realized I was also going to meet for the first time her other “date” boyfriend she had been seeing about once a week. I had heard all about him and them, but had not met him. We dressed at my girlfriend’s house. She did our makeup, hair, nails, perfume etc. It took a long time. She had picked a red with black trim, mini dress for herself.
The guys were taking us to a party at some friend’s house. My friend Donny got there first to pick us up. My girlfriend introduced us. He was very nice, talked about his friendship with my male self like I was new to him. Or course to him I was new to him. I was Michele and we had never met before.
When my girlfriends date arrived we all went to the car. I couldn’t help but notice he was older and very hot. Tall and a hunk. I sat in the back with Donny. He was nice; we made small talk eventually he reached over and held my hand. He leaned over and told me I smelled pretty. I thanked him as he kissed my cheek. I felt so scared he would figure me out, but so far so good.
We went in to the party. It was at a very nice house on the lake. I could see my girlfriend with her dates arm around her waist as we walked in to the house. I must say, I was more than a little jealous. But, Donny was doing the same thing to me so I guess it was ok. I felt his arm around my waist. Occasionally he patted my ass. I was surprised that he was so bold; actually kissing me once when we started to dance. I was shocked; I had never been kissed by a guy before. He was a very good kisser.
My GF came over and danced with me. I had been watching her with her boyfriend; he was so tall and strong. I totally understood her attraction to him. He was kissing her and I could see him rubbing her back and ass. She doesn’t let me do that. Even in private. She was telling me to make sure I was friendly to Donny, so he doesn’t suspect anything. I asked her how friendly. I mean he was kissing me and touching me. She told me I was doing good.
Her boyfriend came and asked me to dance. It felt good in his arms. I completely understood why she liked him so much! When we were done he told me what a pretty girl I am. I knew that he knew who I really was! But, he didn’t let on. I was totally a girl.
Donny and I were sitting talking for a bit. He was holding my hand, touching my knee. Told me how pretty I was and how sexy I smell. He told me he likes girls that dress sexy like me. I felt him rubbing my thigh as we talked. I loved him looking at my legs. I felt entirely like Michele, not my friend Donny’s best friend. He even kissed me a few more times and I welcomed his hot tongue in my mouth.
I was glad when it was time to leave. I felt a little dizzy from drinking some wine. Donny held my arm as we walked to the car. It felt nice. I felt so small next to him.
I saw my girl and her boyfriend making out by the side of the car as we walked up. He was kissing her so hard. As we got in he suggested we go down to the park for a while. They passed a little flask back to us and asked if we wanted a drink. Donny took a sip and handed it to me. I took a sip too, it burned going down. It made me feel warm and a little dizzier. Everyone took another drink and we parked at the river.
Now I know this is a make out spot. I never thought my girlfriend would let me get in to this position. I mean, now I am trapped in the back seat as a girl with my best friend. Even though she had been encouraging me all night to make out with him and feel like a girl.
Donny put his arm around me and slid me over next to him holding me tight. Kissing my cheek. Telling me how pretty I was. I looked in the front seat and my girlfriend and her guy were passionately making out. I could hear her moaning as he kissed her neck and was clearly feeling her up. Donny was doing the same to me and I found myself liking it, even moaning a little myself. My girlfriend had told me early on if he tried to touch me to tell him I was on my period so he would leave my “pussy” alone. He was rubbing my thigh and I warned him and he complied. Instead as he was kissing me deep he put my hand on his hard cock through his pants.
I glanced back to the front seat and my girlfriend was clearly rubbing his cock, up and down still kissing him. He was telling her how sexy she was and how good that felt. I saw him put his hand on her head and push her down. She was sucking his cock, RIGHT THERE! She never did anything like that with me!
Donny was kissing my neck and I was so hot. He kissed me hard and deep and it felt so good. I was glad my small cock was tucked away tightly to hide it. He opened his pants and pulled his cock out. I was shocked. It was so big. It was about twice the size of mine. No wonder she wants another guy I thought.This is what a penis should look like.
He took my hand and placed it on his cock. As I rubbed his rock-hard cock he whispered things to me, how hot I was, how sexy. How good that felt as he continued to make out with me. I could hear my girlfriend sucking and slurping on her lovers’ cock. I had never dreamed of anything like this.
Donny told me to kiss it one time. Just once he said. Like your friend is doing to her lover. He strongly pushed my head down to his lap. He commanded, go ahead. Lick it, kiss it. I heard my girlfriend’s voice. It won’t bite babe. I glanced up and she was watching me. I took him in my mouth and sucked it, like I thought I would like. I felt like such a slut. I mean, we just met. My girlfriend said, “I knew you would be good at that.”
Shortly heard her guy moan and say oh yes suck me. Donny was enjoying my attention. It felt so hot and hard in my mouth. I really had no idea what I was doing. But clearly my girlfriend did. In a few minutes, I heard him say oh yes. I am going to cum. And I heard her gulping and swallowing. He was saying yes, yes baby. Suck me. Swallow all my hot cum.
Donny was getting hotter and bigger. He was telling me how good my sexy mouth felt. I could feel him rubbing my chest and ass and legs. I started thinking what do I do when he cums. My girlfriend was in the front saying mmm that was good. Donny was pressing his big hard cock down my virgin throat. Donny said I am going to cum, I didn’t move away. I sucked harder. As he started to shoot he was moaning and saying yes, what a fucking slut you are. I sucked him until he was going soft swallowing every drop of his hot cum.
When I sat up my girlfriend leaned over the seat and kissed me. She said you did good for the first time. Donny said, hell yeah, she did as he tucked his big cock back in to his pants.
They gave me another shot of whisky. The taste of his cum lingered on my lips. We drove back to my girlfriend’s house. Donny asked if we could go out again. I told him maybe. The guys walked us to the door and got their goodnight kisses. By now I was totally accustomed to having a male tongue in my mouth.
My girlfriend is still MY girlfriend. She is the love of my life. We will always be a couple. But we play lots of fun games. By the way my girlfriend had told Donny who I was from the beginning. But to this day he has never let that he knows. Even though we have since gone on many dates. I love tasting his cum.
