The Story of My Life - Part I

It must have been when I was 14 years old; masturbation was an exciting new thing for me. I was picturing myself with older women (at 40s or 50s) who guided me around sex. One day, I don’t know why, I thought of myself as a young girl who was invited in a woman’s house. Innocent and naive. For a long period this was my favorite fantasize. I never thought that it could be something out of the normal as I was imagining having sex with women.
About one year later, I was alone at home as my parents were both at work. For some reason I cannot recall I tried my mother’s underwear and stockings. I lied down to bed and started masturbating thinking myself as a girl having lesbian sex. Suddenly I realized that I my legs were spread and I was touching my asshole, at the same time I was thinking that a guy was fucking me. My cock was never that hard before. To my surprise I came harder than ever, not to mention the quantity of sperm. To be honest I got scared. Me being gay?
I like girls, I even had a girlfriend. We were not having sex (we were 15 after all) but I enjoyed touching her. I never thought of boys.
I came to the conclusion that those were fantasies and nothing more. I kept dating and a few months later I had my first sexual experience with a girl. I also kept dressing in my mother’s clothes and thinking of me as a girl with a man.
It all changed when I was 16, during autumn. There was a big party in a club, a theme party to be accurate. The theme was 1920s and everybody had to show up dressed for it. Me and my best friend (let’s call him Jim) decided to dress like young cabaret dancers. We got short dresses, fishnets, jigs and everything else needed. We would meet at my friend’s house were his s****r would help us with the makeup. She was 19 and she knew how to do it…
I arrived early that afternoon, Nick was taking a shower so I waited at his room. His s****r came in and we were talking casually. Suddenly she pointed out that we should something with my body hair. She said that wearing fishnets on hairy legs would not be something good. She was right. Nick had just came out of the shower and she explained to both of us that we should shave our legs. We agreed to do so. While we were shaving our legs, she came in the bathroom and pointed out that since we were doing it, why not shaving our hands, armpits and chests. All of those parts would not be covered by the clothes we chose to wear. We did that too.
All that was left was our pubic hair.
She started to apply makeup on Nick while I was waiting. It took her around 20-25 minutes to finish with him. I was next. She told me that mine would take longer as my skin was darker. After 40 minutes I could not recognize the person I was seeing in the mirror. It was not me, it was a young girl. Same as the one I had in mind during masturbations.
We went to the bar and we had a really good time. Everybody thought that our outfits were among the most successful ones. We spotted some girls we liked and hanged up with them, at around 22:00 they had to leave but we managed to get their phone numbers. Extremely happy with our success we decided to celebrate it with a beer. We sat at the bar and ordered two beers. We were drinking and chatting when two more beers came. The bartender informed us of the two guys who bought us the beers. We thanked them, we never thought of anything naughty on that. A few minutes later they came close to us and asked if we could all hang up together. They were at their 40s. We agreed and we had a casual talk. It was almost 23:00 when they suggested to have another drink. As both of our parents were out of town, time was not an issue for us. We said ok but they said that since it was too loud in the bar and we could not talk we should go somewhere else. We told them that this would be ok in any other time but we would look a bit ridiculous in women’s outfit. We laughed about it and then they suggested to go to their place which was close to the bar.
Usually we would have declined but after several beers our defenses were down. Fifteen minutes later we were sitting at their living room having shots of tequila. Both I and Nick were not drinkers and it didn’t took long for us to get dizzy. Peter (one of the guys) and Nick decided to continue drinking at the kitchen while Simon and I sat on the living room’s sofa. We were talking and drinking, suddenly I realized that his hand was on my thighs. I tried to move back and he laughed, he said that this was going on for the last five minutes and it was obvious that I was enjoying it. I told him to stop and I tried to stand up, a difficult task to accomplish when you are almost d***k. He told me to relax and not to worry and I replied to him that even if I wanted to do something with him, which I didn’t, this could not happen when I was at the same house with my best friend. He laughed again, stood up and asked me to follow him quietly. I stood up to (he actually assisted me to do so) and we moved close to the kitchen quietly, I heard some moans and then I saw Nick giving a hand job to Peter.
We went back to the sofa and he came close to me. I could feel his hard cock under his jeans. He kissed me on my neck and slowly moved my hand towards his cock. I remember unzipping his jeans and touching it, I had never done this before and it was a strange feeling. Immediately I moved down and licked it. I opened my mouth and took it in very gently as I was afraid not to hurt him. While doing so I could feel him touching my ass. He spitted his finger and started to play with my asshole. He did that for some time, playing with it but not fingering. At the same time I was blowing him and his cock was growing. It was big, I could not take it all in my mouth so I was just reaching below his dick head. We continued like that for a few more minutes until he came. His sperm was warm and salty, like mine (yes, one of the first things I did after I started masturbating was to try my own sperm).
I was feeling embarrassed, he understood that and tried to calm me. He told me that I did nothing wrong and I shouldn’t feel bad for myself. He talked to me for several minutes and that helped me to relax, maybe more than needed. “I want you to fuck me” I told him and immediately I started to lick his cock again. Somehow I became aggressive; I took his hand and moved it in my back pushing his finger in my asshole. I have to say that during masturbations I had fingered myself in the past. And I had managed to take two fingers so far. I told him that and asked him to be gentle. He told me to move at the bedroom, we did so and I lied down to the bed. He opened his drawer and took out some lubricant. He applied it to my ass and everything seemed so easy now. I kept blowing him until he stopped me and asked me to bend over, I did so. The excitement cannot be described. I felt his cock on my ass, he gently pushed it and after a few seconds he was inside me. A small shout came out of me. He started to move slowly inside me, I was feeling like a girl and asked him to fuck me. He did so, I was feeling his cock coming in and out. The first cock I ever had in my tight asshole. He went faster as time passed but he was careful enough not to hurt me. He came inside me (he was wearing a condom). I took his condom off and licked his cock to clean it. I was feeling that my ass was destroyed. I moved my hand down to check for bl**d, not a drop. He laughed at me and told me not to worry.
Suddenly I realized that we were more than one hour in the bedroom; “where is Nick” I asked terrified. He told me that he was in the next bedroom, “you heard him, right?” he said. I didn’t, he told me that he was more slutty compared to me, he was shouting in a girlie’s voice asking to be fucked harder and harder.
Half an hour later we all met in the living room. It was almost 3 in the morning and we had to go. Even if our parents were not at home, Nick’s s****r would be waiting for us. They drove us back and said that we should meet again during next weekend.
When we returned to Nick’s home we went to his room. We were looking each other without saying a word. His s****r was not there, he left a message saying she was sl**ping over at a friend’s house. Nick was the first to talk when he asked me what I and Simon did. I decided not to be honest with him and just told him about the hand job. He asked me if I listened to him and I said yes. He got red from shame and told me that he was not a gay. I didn’t say anything and he got angry. He came close to me shouting that he is not gay; we had a short fight when suddenly we started kissing each other, passionately kissing. It didn’t took us long to start blowing each other, Nick’s cock was thick and long while mine was fatter but smaller. We kept blowing each other when I stopped and stood up. He tried to do so but I didn’t let him. I turned around, facing him and slowly sat on his cock. My hole was still wide and it was not difficult for his cock to get inside me. I start to move up and down and I was moaning like a bitch. I was going faster and faster until I felt Nick’s sperm in my asshole. He then gave me a blow and I came in his mouth. As I was sitting on his chest, while he was blowing me all of his sperm came out of my ass on his belly. I licked it all and then we kissed swapping cum.
We felt asl**p together. The next day we didn’t talk about it. For several days it was as nothing had happened. Until Friday afternoon when Nick asked me if I wanted him to call Peter and Simon and arrange something for the weekend. I did want it and I asked him to do so.

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Categories: AnalGay MaleShemales
Posted by georgette32hk
7 months ago    Views: 2,274
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5 months ago
amazing story!!
7 months ago
Great story I loved it! I will add to my favorites!
7 months ago
Thank you x
7 months ago
Loved it
7 months ago
great story! thanks for posting!