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Ass Fucking at Fifteen

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This happened when I was a sophomore in high school and lasted only a few weeks. When it ended, I spent the next several years denying and suppressing the memory because at the time it was so taboo and unthinkable to be "queer." Years later, I am a straight male with no desire to repeat these experiences. But finally allowing myself to revisit and embrace the memory, I can say that it was one of the most exciting sexual experiences of my life. Partly that was because I was young and it was my first real sexual contact with another person. Partly it was the erotic, forbidden nature of what we were doing and the acting out of things I had fantasized about in my secret life of masturbation. To some degree, it was a substitute for things I wanted to do with girls, but thought they were too risky re: getting her pregnant and humiliating myself and my family.When I was fifteen, friends would sleep over and we would talk about girls and sex, and sometimes wind up masturbating. One night, an older friend slept over because his parents and my parents were going out together and would be home late. He had a girlfriend but I now believe he was bisexual. We were talking about sex and openly masturbating when he asked if I had ever had anything like a dick in my ass. I did not think of myself as gay, but I loved anal masturbation, going back to childhood enemas, and sometimes fantasized about a hard, bare dick in my ass. Of course, I couldn't just say, "Sure, let's do it." There had to be some "Oh, I don't know if I want to try that" and "You should try it, it feels really good" kind of talk. My whole body was trembling at the thought that it might actually happen tonight. Eventually, we decided I would get it first, and I turned onto my stomach and put some Vaseline where his dick was going to go. It felt so good that I shivered with anticipation as the tip of his bare dick rubbed up and down between my buns and centered on the spot I wanted it to find. The fleshy sensation was so different from the hard, inanimate objects I had penetrated myself with in the past. When I felt it stop right at my hole, I knew that in a moment it would be pushing into me, and I couldn't wait to have it inside me. He pushed it deep into my tight anus in one long motion. It was too painful and I quickly gave up on the idea. The end; clean up and go to sleep.A couple weeks later, he was hanging out at my house with no one home, and he said, "I think you should get fucked tonight." Despite the previous experience, I was horny and actually wanted to try it again, so we got undressed and beat off casually, talking about how and where we would do it. In my many masturbation sessions, I had often bent over various things, sometimes looking at my bare ass in the mirror and thinking about having it fucked or somehow penetrated. It was fun and exciting to talk about this with another person while unashamedly beating off and knowing it was actually going to happen very soon--just a matter of where and how and when. After a few minutes of this, we went into the bathroom where I had done much of my beating off. I liked to go up on my tiptoes so the corner of the sinktop went between my thighs and I could feel the coolness of the tile against my balls as I stroked myself and watched in the mirror. My mom had a makeup mirror by the window behind me, and if I adjusted it just right, I could see my bare ass reflected into the larger mirror in front of me. I often masturbated that way so I could see both my dick and ass at the same time and imagine (or watch) something pushing into it. With its history, this was my perfect private place to have my bare young ass fucked.As I bent over, he slowly pushed just the head of his dick inside me. It hurt, but it felt a little good, too. I loved the feeling of the flared head pushing past my sphincter and popping inside. After several times of pulling out and penetrating an inch or so, I told him to push it in a little more and he pushed about half of his stiff shaft into me. This time, it felt really good, but I said to wait a minute while my sphincter got used to the fullness. With a little more stretching, I was ready for all of it. When it was all the way in, I reached back and spread my buns apart to get it in even deeper. This was the feeling of deep penetration I had craved all my life and through many masturbation sessions. I straightened up a little and, looking in the mirror to fully take in what I was doing, beat off with Vaseline until I came, heaving great sighs of breath.One weekend, our parents went to a convention and I stayed at my friend's house. We spent most of the weekend walking around naked or in our boxer shorts, doing a lot of beating off and ass fucking. I was never interested in sticking my dick in him, nor in any other kind of touching. This was all about being naked and having something big and hard up my ass while I was stroking my dick. The best feeling of penetration was once when he laid on his back and I lowered myself in a sitting position onto his dick. I would describe the feeling as "pleasure-pain" because it was so deep and intense. It felt like the end of his dick was pushing high up against my insides. I wanted to hold that feeling and beat off until I came hard--which I selfishly did.I almost forgot to mention that I was dating his younger sister, and it added greatly to the intrigue of what I was doing. She was fifteen also, and I can still remember the intoxicating smell of her perfume while we made out in a parked car. She had nice breasts that I would fondle through her soft sweater on a chilly November night. We never went any farther than that. One week night, I came over to visit her brother. He had the entire basement as his room, and he said his family knew better than to interrupt his privacy. We were enjoying ourselves when his sister opened the door and called down to ask him a question about her homework. She could not see us, but it felt very dangerous and exciting to hear her voice and know she was there, fully dressed, while I was in this very erotic and exposed position. I later fantasized in great detail about what it might have been like if she had come downstairs, walked around the corner, and seen me naked, bending over, and stroking my dick, with her brother's dick in my ass.___________________[sig]Ben[/sig]

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