My First Encounter
With Gay Sex
by Sissyboytom
This is my first time writing a story. This story takes place back in the mid nineties when I was 13 years old. I would appreciate any positive comments that you have for me. I am sorry for any grammar mistakes. If you don’t like this kind of story then DO NOT READ IT!!!!!!!!!!!!!! Thank You.
When I was ten years old, I began to wear girl’s clothes. I do not know why but I always felt that I was a girl in a boy’s body. I always had to make sure nobody was home while I did this, or I would have probably been sent away. Let me tell you about my self. My name is Tom. I am Five feet Nine inches tall; I have brown hair, and Hazel eyes. I have always had more of femmene body shape to me. Even girls thought that I was a little girlish. One day while I was home, my neighbor came over to play. I had told her how I believed that I was a girl and she helped me pick out some clothes. By the time I was thirteen I was dressing more frequently, but still kept it a secret. I was working during the summer with my friends neighbor John. Now John was an older guy in his Fifties. He owned a construction company and every day after work we would go to his house for some supper. On night we got home kind of late that I just had John take me home instead of going to his place. When I got home there was a note telling me that my parents were gone for the evening, and my sister and brother were gone for the weekend so I decided to get a shower and dress up to play house. I went to bed in just my panties and bra. I woke up the next morning for work and decided that I would keep my panties on but just take off the bra before I went to work. I felt like a real girly wearing panties in public but still tried to keep it a secret. That night after work we went to the store to get some beer. However, when we got to John’s my friend decided to go home, so I stayed to get messed up. After about twenty minutes I decided I would go to my friend’s house and see if he was coming back over but he was asleep.
When I got back to John’s he was watching the television when I looked over and saw a girl having sex with a guy. I was just looking wishing I was her. After looking closer I saw that the girl was actually a guy dressed in female clothes. I got hard instantly and I guess John noticed because he asked me if I liked that. All I could do was nod my head, and he said that he thought I had a girl’s body. He asked me if I had ever dressed up in girl’s clothes and again I didn’t say anything. When he asked me again I said that I did it almost everyday when I was alone. He asked me what I did and I told him. I even told him that I had my panties on then.
What he said next surprised the hell out of me. He asked me if I would like to wear Girls clothes in front of somebody other than a girl. I was thinking about it when he said he had some of his daughter’s clothes at his house for when she comes and visits him. He said I could wear them if I liked. I decided I would love to. So I went to the room he showed me and got dressed in a little school girl outfit. I had a plaid skirt (pink and white) a white blouse with pink bra and pink thong panties. I felt like I was a real girl. More than I did when I left the house this morning for work that morning. When I came out of the room John had just stared straight at me and told me I was beautiful. I felt very beautiful standing in front of a boy. John had me lay down on his bed while he kissed my body all over. I was the hardest I had ever been in my life. John asked me if I had ever had sex before and I told him I had messed around with a girl before but I had never been with a guy before. He asked me if I would like him to suck on my clit, which when he said that started bouncing up and down. He took that as a yes and moved my panties to the side. He was able to get the whole thing plus my balls in his mouth. It is easy to do when there is only three inches to work with. He sucked me for a little bit and then asked me if I would like to suck his cock. I told him I would and got up on my knees and undid his belt. After I got his belt off I pulled his pants down and was amazed at how big his cock was. I had never seen one that big before. He had a nine inch cock and it was very thick. I started liking his head, and then I licked the shaft. After get his shaft wet I was stroking his cock and went to work on his balls. Then I came back up and stuck his cock in my mouth. I was sucking a mans cock and I loved every minute of it. After about 15 minutes of me sucking him he said he was about to cum, so I started sucking faster and faster. About 3 minutes later he blew his load in my mouth. I have drank my cum before but his tasted different and I swallowed as much as I could. When he was finished Cumming I was still sucking trying to get as much as I could. He sat down and help me get the rest of the cum off my face and fed it to me. Then we kissed and he asked me if I wanted to do other things.
To be continued….
Please let me know what you think. If the comments are good I will write what happened after that night. Thank you, Tom.