So these are going to jump around quite a bit as I feel write what I’m remembering as I remember most of it. I was 22, and I got gotten into a bit of a pickle. I got caught on a possession charge and was going to do 8 months in prison. I was told I would be out in 4 months, so I wasn’t that worried going in. By the way, this is like 12 years after the last gay thing, and since then I had only ever done anything with a guy once after that, and it was only looking and jerking together. I won’t lie, I was a bit nervous about getting in a shower with guys, for obvious reasons. This is back before prisons had hd cameras everywhere and the cameras they did have had a bad habit of dying when the COs wanted them to.
My first few weeks there went mostly fine, though I couldn’t help getting a little hard showering with the guys. But no one tried anything. Until one night, as I’m sleeping, I hear my door buzz open. CO Owens came over and told me to get up and follow him. I did as I was told and he took me outside. Offered me a cigarette and led me behind a shed in the yard. As we smoked, he laid it all out for me.
“So here’s what’s going to happen. By the end of your first month here, you are going to have some people here who are going to want to fuck you. Willing or not. Depends who gets to you, it might be more than one, and it might hurt you a lot or kill you. And a couple of my fellow COs might join depending if you get it bad. But I like you, so I’m going to offer you this. I protect you from both guards and inmates. In return, you are going to do some favors for me. Whenever I want, I will take you somewhere and you will make me cum. Starting right now.” He started unbuckling his pants and unzipped. I stared in disbelief, but made up my choice pretty quickly. Gang rape or one guy was pretty easy choice. So I told him okay.
He pulled out his big white cock, and told me to get on my knees and open my mouth. I did as I was told. As his cock got close enough, I reached out and grabbed it and starting kissing it. He called me out, said he knew I was going to like this choice. I gagged and struggled sucking his cock, until he pulled out and starting jerking off on my face until he came in my hair. And it would go like that for a couple of months. I was told I was getting out in a month, and did my best to just keep my asshole a virgin and keep my chin up. I failed one of them.
My last week, my last three days. Owens got me late one night. Didn’t bother taking me anywhere. He stepped into my cell and took his pants off. My cellmate, a 70 year old black man who I liked a lot but never told him about Owens. He told me to get in the lower bunk and take off my pants, something he never did. I sat next to my cellmate Clive, and took my pants off. I could see in his eyes he was not cool with this, but he did keep glancing at my cock. Owens told me to get hard, and that’s what I did. Owens told Clive if he acted out he was going to fuck him every day for his next ten years. Owens jerked his cock off on Clive’s face just to make the point. Then Owens told me he was going to fuck me. I could barely hear it before he was shoving his finger up my ass. I begged him not to. I cried and begged. He told me it was the last time so he was going to make it last, and he shoved the tip of his hard cock inside me. It hurt so bad as he slowly shoved six inches of cock inside me. I cried, and hated myself for getting hard, and hated Clive for watching intently as my ass was raped. Owens flipped me over after a minute to my hands and knees and shoved my face against Clive’s crotch, which I found to be hard as a rock. I cried on his cock as Owens fucked me from behind. Owens saw Clive was hard and told him to take his cock out and shove it down my throat so I would stop begging and crying. Clive, the sweet old man I had bunked with for months, pulled out his thick black cock, hard as he could be, and shoved it down my throat as I begged him not to.
The two of them used me like that for what felt like hours, but was probably less than one. Clive never fucked me, but he got his. After I felt Owens cum deep in me, he told me he was going to rape me again unless I could make Clive cum before he could get hard again. I gave Clive the best blowjob I could at that point, as exhausted and in pain as I was. But I did make Clive cum on my face before Owens could get past a semi. I collapsed on the floor, used and dirty and shameful. I cried and tried my best to ignore as Owens forced Clive to suck his dick once he was hard again. Next thing I know, Owens was leaving, and Clive was putting me into his bed with him and holding me as I cried. A few days later I was gone and never told a soul what happened that day.
Source: reddit.com/r/sexystories/comments/ve67y9/my_life_has_been_weird_part_4_mmm