Before I went into prison I was 100% straight. Absolutely no man was going to try anything with me. I'm a big guy, six feet three and through my last job and hitting the weights, I've also built me a damn fine muscular body. It helped with my door work, but alas it was performing my duties on a door, I got a little out of hand.
No matter what anyone tells you, time inside is either productive or it's total bullshit and wasted time. I spent my eighteen months being productive, studying and getting incredibly fit. However I did after a few months begin to suffer with my sexual needs. Wanking is ok, but it doesn't fully scratch that itch. I knew of some guys who had bitches and used them daily. They on the outside were married men, straight men, but inside they needed that little extra to get them through the day. I resisted even though some of their sluts were offered to me, and I might have succeeded in making through my sentence had it not been for Jack.
Cutting this bit short, I ended up having my cellie moved (Drugs, dickhead) and two days later had a newbie placed in with me. He was young, vulnerable and not at all what you'd think of as a criminal. He was also and I say this with hindsight, a very good looking young man. Straight away the men who were interested, started to move in on him. He was beaten for refusing to suck the dick of one guy, and I had sort the guy out. Which cost me three months on my sentence, but I couldn't be seen to be weak. Another attempt to get him to have sex, only ended up with me warning off the the two men who'd wanted to fuck him. Then one of my training buddies inside told me, if I didn't take him myself as a bitch, I'd probably be fighting every other day.
That same night after lights out, I'd just turned over when I heard Jack say "You'd better get this over quickly as I'm not sure I can take this any longer". Apparently the same guy who I trained with, had spoken to Jack and told him, he needed to make himself my fuck piece.
Getting off my bunk I went to his bed and spoke to him for over quarter of an hour. We were both reluctant to enter into something sexual together, so we planned on telling everyone he was now my bitch. Unfortunately in prison it isn't as easy as that. Not wanting to go into it too much, I had to be seen/known to be fucking Jack.
The following night he got onto my bed naked and slipped his hands into my shorts. There was no kissing that first time. Only Jack stimulating me with his hands, then removing my shorts he went down on me. For someone who'd not sucked cock before, Jack was instantly very good at it. My dick became rock hard and I must own up to wanting to fuck him by the time my cock was twitching and pulsating so hard.
Spitting on his arsehole, and then using cream he had for a cut eye, I eased my cock up his arse from behind. It took an age for it to bottom out, but then I do have an eight and half inch cock. Throughout our first fuck, Jack felt pain and was uncomfortable, but the prowlers as I called them, also heard his moans and groans as my cock pounded deeper and deeper into his body. By the time I was ready to cum I was actually enjoying being inside his arsehole. Cumming up him made everyone know he was mine and it also instantly stopped further attempts by other men to fuck him.
For me that was going to be that. But the next night Jack entered my bed again naked. Only when he sucked on my cock, I spun him around and took his much smaller cock into my mouth. I wanted him to feel at least a little bit turned on when I fucked him, so I gave him as good a blow job as he was giving me. It was Jack again who took the lead. Getting me to lay back he used the cream again and mounted my cock. It was a much more sexual time the second time, as I got into watching his face and seeing his cock bounce as he fucked himself on my dick. Then like a rubber band giving way, his arsehole opened up and my cock slid right in. At the same time he moaned out loud, but it was a moan of complete and utter joy. We fucked one another for over an hour with Jack taking two loads of my cum deep inside his bowels. The second time I fucked him, he was lay on his back and I fucked him missionary. Driving my cock into him, he reached up and pulled me down to him. We kissed and for me it sealed everything. It also proved to me, I was going to protect him as I was fully prepared to make him my prison lover.
Jack and I fucked almost every night from then on. I found that I was eager to be inside his rear hole and often wanted to fuck him in other places, other than our cell. But that was too much and you had to show the other side of yourself beyond the cell door door.
After five months Jack left prison and I got on with my time. He kpt in touch by writing and I found writing to him a way of making myself horny. I did take another younger lad under my wing, but he was much more cock sure of himself. And within a month was fighting his own battles and not relying on my cock to get him some piece.
Time done and on the out. My wife picked me up and I soon merged back into my home life again. Yet there was something missing and that something was Jacks mouth, cock and arsehole, plus he himself.
It wasn't hard to track him down as I had letters from prison. I had to hide them as they were all very sexually explicit. Arranging to meet up with him at a hotel, we spent a whole afternoon sucking and fucking, and I did something I'd never done inside. After cumming up his sweet tight arse, I actually licked and sucked my cum out and fed it to him by kissing him hard.
Our lives have moved on, yet we still find time to have sex. I've told him I'll never leave my wife or betray her with another woman, but I doubt from now on, I'll ever stop fucking younger men.
Jack has proved one thing to me. Never say never.

Comments

Anonymous

by Anonymous on Nov 29, 2017 at 9:23 AM

I spent time in prison when I was 19. Had 15 months to serve. Being that young and going into a prison you could imagine all the hits I got. I didn't last two weeks before a group of three guys r**ed me. After that I knew something had to be done. I was in a cell with an older guy, he told me one night if I sucked him I wouldn't have to worry about being r**ed anymore. Well it turned out that it was just sucking involved, he ended up fucking my ass the next night. I let him fuck my ass daily for my whole sentence. And I swear everyone in prison has a huge cock. He was definitely 8” and uncut.

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Anonymous

by Anonymous on Nov 29, 2017 at 9:25 AM

My first experience with a man was in prison - best blow job of my life and the tightest ass I ever fucked. I rather have a man suck me than a chick.

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Anonymous

by Anonymous on Nov 29, 2017 at 9:48 AM

How old were you when in prison?

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Anonymous

by Anonymous on Nov 30, 2017 at 4:46 PM

I got ninety days in a county jail and being smoothly cute it wasn't long before I had a friend. I was sucking and letting him fuck me because I was really afraid of getting r**ed. I actually started liking it too? When he was out on a work detail I had my first BBC, he said my ass "was like cotton candy, sweet,tight and so good to look at!" We kept it our secret, and when my cellmate was on details we'd get together. His was the first cock I sat on too!

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Anonymous

by Anonymous on Dec 3, 2017 at 12:00 PM

We hired a mail boy in the office and soon after he began he approached me and told me (we knew he had done time) he had come out of jail with a "hot and horny asshole" he had been fucked so many times. He said, "I need it constantly up my poop-chute, man." I had little experience with males then but just looking at his wild eyes hardened me. The first moment I was alone with him he gave me a world class blow job and then pulled his pants down and backed into me until I was balls deep. That was a while back and I have now have dumped half a gallon into him. He was so needy that I told my boss about him and he is now also cum-dumping into the kid. The kid is insatiable.

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Anonymous

by Anonymous on Dec 4, 2017 at 6:41 AM

#5. I know how the poor kid feels. I was a fresh sweet faced kid when I went to a young offenders youth detention center for joy riding in a "borrowed" car. I was the only one of us kids that did any time, 6 months because my strict parents thought it would teach me a lesson.

Being a preppie looking suburban kid, smoothly cute with a fresh well shaped little ass I was fresh meat for the tougher inner city kids. I was pretty naively innocent and though shocked at the request of two boys on my second night there I reluctantly sucked or more like slobbered there boycocks. I was embarrassed and pleaded with them not to tell anyone.

The next night one of them snuck into my bunk and in my underpants. I soon started having sex with other boys too. This continued till I was released, I'd even got it from two of the weekend staff members. I'd swallowed and had volumes of cum dumped in what was once a fresh and cute boy's bottom in my short incarceration.

I still looked preppie and sweetfaced when Mom and Dad took me home. I still had the beautiful smooth fleshed boys body with the same looking pert, innocent well shaped boycheeks. I now had desires that I couldn't control. I'd began to love my boy lover's as aggressive as they were.

My first indiscretion was with the older guy who'd sell me beer at the liquor store because he thought I was cute. He'd give my butt a little pat telling me how cute I was as I carried the case of beer out the door.

I'd asked him for a part-time job after school and he bent me over the stack of cases in the back room my first day. He said he wanted to Fuck me, I nodded okay. My jeans down he slid the back of my underpants down exposing my firm pink cheeks. He lubbed his cock and worked some between my cheeks and pushed a finger in. It startled me and I clamped down on it. I immediately ralaxed with a sighing whimper telling him it feels good. The scratchy feel of his rough fisted hand gripping his cock against my soft smooth fleshed cheeks as he searched momentarily for my sweet spot.

I arched my back and wiggled my cute boy's bottom telling him he found it. I gripped his cock tightly. I uncontrollably came in my tighty-whitie underpants still barely covering my boyhood in the front. He'd barely started his penetration and here this cute kid that he's been trying to Fuck for over a year was before him, bent over with cute fresh little boypanties down in the back. his tight ass wiggling about on the end of his dick barely in his boypussy. He couldn't help it, he blew his first load of hot cum defiling his innocent boycheeks.

I felt his cumload filling me as he pushed all in till his low hanging old man balls my smooth skinned inner thighs. He fucked me every day I worked, sometimes twice. I couldn't say no to anyone it seemed. My preppie prettyboy looks became my burden.

Everywhere I went guys were hitting on me. It wasn't different than before my incarceration, boy's and men hit on me before. Now though, I couldn't say no. I'd turned into a boyslut going home daily with my underpants buttered with my and my lover's cum. It was either that or a tummy full of it.

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Anonymous

by Anonymous on Apr 8, 2018 at 1:11 AM

#5 - Stop adding your BS comments to all these stories. It's obvious both that you're a frequent poster and that your comments are nonsense.

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Anonymous

by Anonymous on Dec 17, 2018 at 11:37 PM

#5- More pae do bullshit from Mr Tighty-Whitie.

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