I was only nineteen when this happened. I was in San Francisco, playing guitar with a rock band who I won't name. After the show I was back at my hotel and I got a strange phone call. It was from a guy who had been in the audience at our show the previous night. He said he had seen me on stage and thought I was nice and he really wanted to meet me! Maybe I should explain that I have very long brown hair, I am skinny and quite feminine looking for a boy. My name's Chrissie. I was a little nervous about meeting this guy, but he sounded nice. He invited me to his house, it was on State street I remember. His name was Sandy. When I got there I rang the bell not knowing what to expect. The door opened and this pretty girl greeted me. As soon as she spoke I knew she was a boy. I wondered what I had let myself in for, but I was strangely excited. Sandy was wearing a short black skirt and black nylon stockings and a peach-coloured chiffon blouse. He had beautiful blonde hair, long and wavy. His body was slim and he had long, sexy legs. He gave me a glass of white wine and we sat and talked for a while. He had a beautiful face like a girl, with big blue eyes and soft, red lips. He must have had hormones because he had lovely rounded, sexy little breasts. He said he had watched me playing on stage and he thought I was beautiful. He kept telling me I was pretty. He loved my long hair. I was flattered. I told him I thought he looked like a very sexy girl and he loved that. He kept stroking my hair. It felt nice and I let him. He asked me if he could kiss me. I said OK and he gave me a sweet little kiss on my mouth. It was lovely. He kissed like a girl, really softly. We spent a long time kissing. It was so exciting kissing him, knowing he was a boy. We drank more wine and just kept on kissing and kissing. He told me I was delicious. He really made me feel good.
It felt incredible just kissing him. We were kissing with our tongues in each other's mouths, licking each other's lips. He had bright red lipstick on and after about an hour we had kissed it all off. I loved his mouth, it was so full and soft, very sexy. As we were kissing I felt his breasts. They felt so beautiful, small but so soft and round like a teenage girl's. He wasn't wearing a bra and he sighed as I slipped my hand inside his blouse and felt them naked. I unbuttoned his blouse front and pulled it wide open so I could look at his lovely breasts and kiss them. I took off my shirt and we sat kissing and feeling each other for ages. He said he loved my smooth skin and he kept telling me I was "so feminine". I told him I loved being girly and I asked him if he had anything pretty I could put on. He went over to his wardrobe and brought out a red satin dress. It was short with a deep V-neckline and short sleeves. I took the rest of my clothes off and sat naked in front of him. It felt so wild and sexy, with nothing on, sitting with a beautiful half-naked transsexual. He told me I had a beautiful body. He came and sat next to me holding the dress and we started kissing again. He was touching me all over. He was very gentle. He stroked my thighs and touched my cock. Ooh. I have never felt anything quite as sexy as having my cock played with by a pretty transsexual. He dropped the dress on the bed for the time being. He told me my cock was "so cute" and he fondled it for a long time. Then he went down and kissed it with his beautiful soft, girly lips. He took it in his mouth. I was in sexual ecstasy. He was sucking my little cock and making it really wet. It felt absolutely divine and it wasn't too long before all my five and a half inches was rock-hard in his lovely wet mouth. I wanted to see his cock too and I pushed his skirt up his legs. He had lovely smooth thighs above his stocking-tops. I couldn't help but feel them. He was wearing sexy black panties with lace on them. I could see that his little cock was hard inside them. He lifted his bum a little and I slipped his panties down his thighs. He looked so sexy with skirt up, his panties pulled down over his black stocking-tops, his little cock sticking up all hard. It was just a little bit bigger than mine. I was feeling outrageously sexy and I started kissing him all over his thighs and his cock, making him wet everywhere. He was making little girly moans, he kept saying "Oh, Chrissie" as I kissed and licked his thighs and his cock. He wanted me to put the red dress on. I stepped into it and slipped it up over my naked body. Ooh, the satin sliding over my bare skin. It made me tingle. My pretty boyfriend zipped it up for me. I looked at myself in the mirror. I did look very sexy and feminine, the front of the dress was very low-cut and showed off my smooth chest, and the hem came half-way up my thighs. I felt so pretty and girly. It was a delicious feeling to wear a dress and have no panties on underneath. My naughty boyfriend had taken his panties all the way off too and he was laying back on the bed looking at me with skirt pulled up and his legs wide open, showing me his hard, sexy cock. I could see his pretty little bum hole. I slipped my dress up my thighs and showed him my cock. I went and got between his thighs and started rubbing little cock against his. That made him really excited. Suddenly he cried out and I felt him spurt come all over my cock and my tummy. It was so wet and warm and lovely. I slid my little cock around in the slippery mess of his come. I laid back on the bed and he came and started kissing my cock and licking his come off it. I can't remember everything we did that night. I know I asked him to put make-up on me. I wanted to look sexy and feminine for him too. I was feeling so outrageously naughty, and I wanted to try on all his pretty girl's clothes. I remember him putting a pair of black stockings and a garter belt on me. I kept calling him Sandra and he loved that. We were kissing and feeling each other all night, dressed as really slutty girls. He told me I looked like a vamp. At one point we laid together on the bed and sucked each other's cocks. I loved sucking his cock. We both licked each other's bum holes too. He was so clean and sweet and pretty. Then we spent a long time just laying together in our pretty dresses with our arms around each other, kissing like lezzie girlfriends. It felt so nice. I think we drifted off together into a light sleep. I do remember that hours later, in the early morning, we both started to get really hard again. We were both so horny then and we got disgustingly sexy. I remember him sitting with his dress pulled up and his gorgeous girly legs wide open showing me his hole. He had some cream he was rubbing all over his bum, it was glistening. He kept mouthing the words "fuck me" and slipping his finger up his hole so I could see. My cock was raging hard and I got between his legs. He took hold of my cock and touched the tip of it on his slippery little hole. I pushed and my hard cock slid right up inside him. It was lovely fucking him using the cream, my cock slipped in and out so easily. I wanted to keep fucking him for hours but after a few minutes I couldn't hold back, the sexual feeling was too intense. I cried out loud and I spurted a big load of come inside him. After that I let him rub lots of cream all over my bare bum and he fucked me too. I was just in a cute little bra, nylons and a garter belt by then. I acted really girly for him, wiggling my hips and wrapping my legs around him. He loved the feel of my stockinged legs around his body. He kissed me a lot while he was fucking me. It was lovely to feel his cock inside me. He squealed like a girl when he came. It felt so warm and lovely inside me. I love being fucked by pretty boys. When we finally kissed goodbye it was noon the next day. He gave me the red dress as a keepsake. I took a taxi back to the hotel in a trance.
It's a true story.
If you liked it, email me at sweetlissy2001@yahoo.co.uk