Jailhouse Ass

by Jethro Maki

12 Oct 2006 4464 readers Score 7.9 (20 votes) PDF Mobi ePub Txt


When I was in my late twenties I met this guy in the baths. He was a couple years older than me, and obviously had had in interesting life. His arms were covered in tattoos, and he had longish hair and a gap between his front teeth. He attracted my attention right away, and we cruised each other warily for a bit until we finally got together in my room.

He had a great cock, and a way of sighing as I got to my knees and took him in my mouth. His hands sat on the back of my head, his fingers locked together, and he kept a downward pressure on me that increased on the upstroke. I was thoroughly turned on, and after sucking his cock while caressing his balls softly I stood up and our eyes met.

We looked at each other for a moment or two, and I had time to notice that he had brown eyes before he broke into a leering grin and put his hands on my hips. He turned me around, and began to lick my ass, deeply and with much force. I moaned and pressed against his face. His hands stayed on my hips, and he pulled me closer to him.

His tongue felt incredibly warm and soft on my ass, and his rough stubble brushed against me, making the senses all the more keen. We continued doing this for what seemed like a long time, time enough for me to be aware once again of the background noises of the baths, which are always such a fascination to listen to.

At length we stopped, and he stood up and turned me around. Our lips met, and I could smell the scent of ass, strong upon him, which touched yet another chord of sensuality in what was building between us. There could only be one next step.

He put on a condom and entered my ass, with absolutely no regard for my own comfort, and this turned me on all that much more. The note of excitement was singing high between us, and getting stronger all the time.

His cock felt so good in my ass, it was the subjugation that I knew I needed, that was the keystone of so many fantasies. He thrust in and out, his hands still on my hips, holding me in place. At one point he roughly pushed me forward so that I no longer stood, but knelt on the edge of the bed, my ass exposed and entirely at his command.

He had no mercy, and neither should he have, since that was the unspoken agreement between us. Civilized behaviour might return after the climax, but for the now I was completely under his control. He held my ass in just the right position, and let me stroke his balls as they hung down and slapped against my ass as he fucked me powerfully.

For all this, and maybe because of it, the fucking didn't last all that long. He thrust quicker and quicker into my ass, and then without any warning he came, making only a soft moan to announce the fact. I could feel the head of his penis expand inside me, his breath became quick, and then it was done.

He pulled his cock out of my ass, stripped off the condom and flopped on the bed. I lay beside him, and we shared companionable silence as he recovered his breath. I wanted him to fuck me again, and so pulled out my pack of cigarettes and offered him one, hoping this would be an encouragement to conversation and another round. He took it and I lit him up in silence, then he looked me in the eye and nodded.

We started to talk, and it turned out that he had been in prison (my cock started to get hard again about here), and that he had just been released a couple weeks before. He had missed the male sex, and he knew just where to go and find it. We started to talk about prisons, and what the sex was like there. He told me of when he had been in custody for a court appearance, and had been put into a cell for holding with a bunch of others. On that particular night there was a young man in his early twenties that was put in the cell with the rest.

He was pretty scared, and didn't talk to anyone at first. By a coincidence, some of the most notorious ass fuckers in the prison were in the cell waiting for court appearances, and my partner was buddies with one of them. He was talked into going over and making an approach to the young man. A bet was raised, as they sat there looking at this new entrant and talking in low voices. My friend was bet a carton of cigarettes that he couldn't talk the young guy into giving up his ass for anyone who wanted some.

The young guy wasn't too talkative when my friend approached him at first, but the offer of a cigarette and a kind word started off a level of trust. At length they got to the cell and what happens in prisons. My friend told the young guy that there were guys in here who wanted to fuck him, and in a few minutes when the shift changed outside and the night watch started, they were planning to come over and get what they wanted.

The young guy started to freak out at first, of course, and looked around defensively. My friend calmed him down though, and told him that there was an easier way to deal with the situation. He was going to get fucked up the ass eventually by a bunch of guys whether he liked it or not, and so it would be much better for him if he took his pants off and bent over the bunk on his own, because then they would be less rough with him. As a final plug for this course of action, my friend mentioned that since he was obviously going to get fucked a lot while he was in prison, it would be a good way to learn to take it now.

It apparently took a number of repetitions of this argument in order to get through to the young guy, but in the end my friend did convince him. When the shift changed, and after a couple more promptings, the guy got up and solemnly took off his pants, then got onto his knees on the edge of the bed and offered up his ass to the waiting throng.

It wasn't long before this invitation was answered, and in the hours that followed my friend told me that after he had taken and enjoyed a generous slice of this fresh, sweet ass he walked around the bed and knelt before the guy's face. He watched it intently, and as he did so the buddy of his who he had made the bet with walked over and made the young guy suck his cock. As he did so, he said out loud, and with a chuckle, that he had lost the bet, and that he owed my friend a carton of cigarettes. Apparently the look on the young guy's face as he heard this and as the cock went into his mouth was enough to make my friend come without touching his own cock at all.

By the time he had finished this story his cock was as hard as mine, and without another word I got up and knelt on the edge of the bed. This time, with the edge of his excitement worn off, and the true full flow of sensuality taking the place of the first and more uncertain stream he fucked me on and on, sometimes covering my mouth as though I were about to yell out, lost in some other memory of his own from his years of enjoying hot prison ass. My own imagination kept pace with his, and in this way our passions became synchronous, and we came together as though we were lovers who had practiced for years, thundering great climaxes that left us breathless and panting.

We collapsed again on the bed, bathed liberally in the sweat of our exertions, myself stretched across his lap, and his hand on my ass. After a period of catching our breath I lit us some fresh cigarettes, and asked him to tell me more about prison sex. He took the cigarette in his hand, inhaled greedily, and then smiled as he slowly and luxuriously exhaled. It was going to be an interesting night.

by Jethro Maki

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