Confession #38062 | Anonymous Confessions

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Bi-Sexual Male / 20

One of my friends just got sentenced to 3 years in prison.

This past two months leading up to his court date for his conviction and sentencing I've been going over to his house almost daily to fuck his ass. He wanted me to break his ass in so that when he gets to prison he's used to getting fucked.

So my thick 7" cock stretched out his tight 20 year old asshole. Wonder how prison is going for him. He looks young, small framed and blond hair. He already said he can't fight a d he'll definitely probably end up some guys wife while in there.

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# 38062 - by Anonymous

by Anonymous

My 35yo married, professional life long friend was sentenced to 3 years for a white collar crime. He was homophobic his entire life, mocking me for defending gays and bi's (men and women). I came out of prison a jock, masculine power bottom relieved his wife had divorced him. Needless to say, he recovered professionally (better than when he went in) and love nothing more than getting his ass fucked. He said, the first guy to get him was hung, and when it went in it was like a red hot poker splitting him into. In about 2 minutes that pain had turned to pure pleasure and he blew a major load without touching himself .. said his legs jerked, his body quivered, it was like electricity running from the bottom of his feet up the back of his legs, his back and to his head. He almost passed out it was such an intense orgasm - without touching his dick. He can milk my dick and his ass is hotter than any pussy I ever had. Did he cum without touching himself? Yes, one time. However the other hundred fucks were just as intense.

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by Anonymous

I was a cutie as a boy, precoscously in trouble a lot and got a few months in a young offenders detention center at fourteen.

The older and tougher boy's were all over my prettyboy rosey cheeks and pouty lips from day one. I had an exceptionally gorgeous freshly firm and well shaped set of boy cheeks. Cheeks like to little mounds that attracted attention since I was a little kid. Within a week I had more boycock of various sizes well planted inside while smooth skinned bellies both tight and fleshy bouncing off my firm cheeks.

I went home to Mom and Dad with the smoothest skin, most likely from sucking so much boycock and I still had those two tightly gorgeous twin mounds. Still well shaped and firmly tight and though they looked just as fresh as the day I went in, they'd been freshly fuckd daily and sure needed satisfying after a week back home.

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by Anonymous

#1 I've never known anyone to enjoy prison sex. I work with a guy that is a homophobe because he had to get his ass fucked in prison to survive his 4 year sentence. He's marr with kids now but still recalls his days of taking it up the ass

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by Anonymous

If you know how to please a guy in prison, really please him. You'll have an easy ride (Pardon the pun) in prison. I know, my asshole was serviced and rented out to over sixty different men in my eight year sentence. As a free married man, I still entertain at least four of them every year...

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by Anonymous

I did ninety days for a possession charge when I was eighteen. I was attractive and really feared what was going to happen to me. I ended up having sex but wasn't r**ed, it was consensual with two guys.

I don't know if it was out of boredom or that I really found them attractive. I had sex with these two guys pretty much daily. There were three cell's with two bunks each to a block with one shower.

It was just the three of us most of the time. They were in their early thirties. I was taking a shower after a couple of days and noticed them watching me. They remarked how beautiful I was for a young kid,"beautiful skin, really smooth looking, and a cute butt too, prettyboy lips" they both joked laughingly.

I masterbated in my bunk that night thinking about what they joked about. The next day I secretly had oral sex with one of them while the other was out on a work detail in the morning, asking him not to say anything. I did the same for the other that afternoon. I felt ashamed. I'd fooled around with another boy when we both were preteens starting puberty, and yes it was a lot of touching, spooning and even oral, but thought I'd outgrown it.

I laid with the morning guy that next day, felt his manhood swelling between my cheeks as he spooned me. He took me, I gave up my virginity without any struggle. Snuggling my naked still boyishly cute cheeks with his cock that seemed too big till it was all in. I regained a sense of clarity, of needing to be touched and to touch, flesh against flesh.

I wasn't in a large prison, but rather a small county jail. I'm sure if it was a prison my days would of been a nightmare rather than moments of dream like bliss.

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