30 Days In Jail Pt 1

Then he brutally kissed me again, this time working his tongue into my mouth and causing me to gag as his dick had already done. My jaw came unhinged and I just let him have his way.


I was only in for thirty days, and then not because of something I’d actually done. My buddy Phil had left drugs in my car, and the cops found them when they stopped me because I was driving a little too fast when I pulled away from a country beer hall they were staking out. I should have known better. I was only nineteen, and I shouldn’t have been in that beer hall at all, let alone drinking. But I’d just finished my first year up north at Yale, and I was on the top of the world.

Thirty days in a county lockup had been my sentence. And not a lockup in a suburban county like the one I lived in but in a county back in the hills, where life is a lot rougher than where I came from.

I stopped going to the workout room, but the inaction was making me so jumpy that I volunteered to go out on work details. This proved to be a big mistake.

On my seventh day, my first work detail came up. We were going out to a rural spot to clear brush from the side of a road running through a heavily forested and hilly area. It was with great dismay that when I jumped up into the back of the van, I saw both Bobby Joe and Maurice among those who were going out on the detail.

It was a hot day and the work was hard. We had small saws and machetes and were clearing brush and saplings back some twenty minutes from the road. There were six inmates and three guards. Maurice clearly was in charge and everyone there, including the two other guards, were afraid of him. Everyone, of course, except Bobby Joe, who seemed to be a special friend of Maurice’s.

Bobby Joe was probably the best and fastest worker among us. It wasn’t long until he was so heated up that he stripped off his shirt and undershirt and was swinging away, covered with sweat that matted the thick, black hair on his chest and arms into swirls and made his undulating muscles gleam in the sunlight. The other inmates quickly followed suit in stripping down to their waists–all except for me.

“Take off that shirt,” Maurice called out to me in a booming voice. “Can’t you see it’s too hot to work in?”

I pretended that I hadn’t heard him.

“Take off the shirt, I said,” Maurice boomed again.

“I’m okay the way I am,” I answered in the most pleasant voice I could muster. “But thanks, anyway.”

Maurice stomped over to me, and all of the inmates stopped to watch us.

“I said for you to take off that shirt, son, and I meant what I said.”

“Sure thing, Sir,” I said and I stripped my shirt and undershirt off. My eyes flicked over to Bobby Joe, and I could see a wide smile of appreciation on his face.

“And because you didn’t do what I asked, you can go ahead and strip all your other clothes off too and work that way for a while.”

I was dumbfounded. “But, Sir, this is a public road.”

“Good point,” Maurice said with a big smile. “You can go on into the woods there a bit and clear brush over by the picnic area. We’ll see that no one goes in there, but not much of a chance they will. Not many want to picnic next to where a chain gang is working.”

I started to argue, but I could see that this would just get me into more trouble, so I started to move off toward the picnic area.

“No. You can strip here,” Maurice said. “The clothes will still be here when you get back.”

So, I stripped all the way down to my work boots and could see that this gave both Maurice and Bobby Joe a little thrill. I was in very good shape and was better hung than the average.

“Okay, now go on over into the picnic area and start working,” Maurice said. You can’t go there alone, and if a guard goes, that will leave too few guards here, so . . . Bobby Joe, you come on over there with us. The rest of you go back to what you’re doing here.”

“Oh, God,” I thought, as I stumbled off into the brush, trailed by Maurice and Bobby Joe. The very worst situation I could think of.

Maurice and Bobby Joe watched me work for a while, and the first thing I knew they both had their dongs out of their pants and were working them. Bobby Joe had one of those championship dicks in length and Maurice’s was regular sized but was extra thick, and his balls hung low out of his fly.

I tried to make a break for it then and run back to the road, where maybe I could get some help from the other guards. But Bobby Joe lashed out with a hand and caught me as I ran past him and slammed me up against a tree. The blow caused me to sink to my knees, my back to the tree, and Bobby Joe was standing up against me, his pelvis pushed into my face.

“Suck me,” Bobby Joe commanded in a husky voice.

“Maurice,” I called out plaintively, begging for help.

“Maurice ain’t going to help you none, pretty college boy. Open those lips and suck my dick. And don’t do nothin’ funny while you’re about it.”

He grabbed my hair with one hand and his dick with the other and forced his tool into my mouth. I gagged as he filled my mouth cavity.

“Ain’t done this before, have you pretty boy? Well, you’re going to get real good at it in days to come. Open wider and get your teeth out of the way and your tongue runnin’ under my dick. There, that’s good. Now let it slide in and out. There, yes, like that. Ahhh, such a sweet, soft mouth.”

I felt tears coming to my eyes, and I was having trouble not gagging. His dick was getting bigger and harder as he slowly worked it back and forth in my mouth.

“Now, I’m going to pull out,” Bobby Joe said, “and I want you to suck on the head like a lollipop and to work your tongue around it. Ahh, yes, I like that. You’re going to be a good bitch.”

His dick head was big and the pisshole was leaking precum. It tasted salty. The sweat of his groin was giving off a strong musky smell. These were entirely new sensations for me, and were not all that unpleasant. I admit that when I was being propositioned in high school, I let my imagination play with the possibilities, and I could feel my own tool coming to life under these new sensations. I also admit that being forced took much of the guilt away and was also turning me on.

“There, that’s good,” Bobby was saying after he’d pushed his dick back in and had pumped my mouth for a couple of more minutes. “Stand up.”

I did so, and he pulled away from me a bit. I was trembling there, close to him. He held my head between his hands and came in for a kiss. I struggled with him, holding my lips together hard, straining to create a solid barrier to him, my arms went between us, and I tried to elbow him away from me. He brought his chest in hard against mine and lashed out with one of his hands, backhanding me hard across the mouth. Then he brutally kissed me again, this time working his tongue into my mouth and causing me to gag as his dick had already done. My jaw came unhinged and I just let him have his way.

The next thing I knew, Maurice was next to us and was digging my arms out and swinging them up and around the tree, where he used handcuffs swung over a branch above my head on the other side of the tree to suspend my arms over my head.

Bobby Joe continued his long kiss, as his hands flew over my naked torso and explored my balls and cock, which started to engorge at his touch.

“Whooie!” Bobby Joe exclaimed, as he broke away from my lips and started to wander down my body with his lips. “You’re one fine bitch. Candy, candy. How sweet.”

My lips now free, I started to yell, trying to get help from anywhere it might come. The ever-helpful Maurice whipped a dirty handkerchief and a roll of duct tape out of his pocket and had me quickly gagged.

All I could do was tear up in frustration and make muffled sounds of objection as Bobby Joe tongued and teethed my nipples and continued working his mouth down across my belly and taking possession of my dick, which responded to his attention, and my balls. In no time, he had his strong hands under my thighs and jackknifed my legs up and off the ground and swung my ass up to his waiting lips and tongue.

I was being penetrated and wetted with his tongue, which dug ever deeper, widening and lubricating my hole.

“Ah a really tight ass,” Bobby Joe was saying as he dropped my legs and stood and turned toward Maurice. “We got ourselves a virgin, Maurice. Young meat. Yum, yum. Can I have him? Can I get firsties on a fuck?”

“Yeah, fine,” Maurice answered. “But then you gotta do me, Bobby Joe. I’m dying here. And you gotta go easy with the kid. You’ve got a real club. The damage can’t show when we get back.”

So this was how it was between the two of them.

“Thanks, Maurice. You got a condom and some lube? He’s gotta be open a lot more if I’m goin’ get up in there.”

Maurice, the walking supply closet, produced a small tube of lubricant and a condom in a packet.

“Now, let’s get him turned around and hangin’ on a lower branch,” Bobby Joe said.

The two of them manhandled me while Maurice released the handcuffs and got me turned facing the tree. Then he handcuffed my arms again around the tree on a somewhat lower branch than before. Bobby Joe pulled my legs away from the tree by the hips and his lips went to my asshole again. Maurice slipped up between my legs and hunched in front of me, with his back to the base of the tree. He proceeded to take my cock in his mouth and give me head, while Bobby Joe was lubricating my ass, first with his tongue again and then with his fingers, heavily laced with lubricant.

I grunted in pain as he worked first one finger, and eventually three, into my ass, probing ever deeper and opening me up. The pad of a finger found my prostate, and, under the spell of circular rubbings on that, I ejaculated down Maurice’s throat.

Then both Bobby Joe and Maurice rose and stood near me, where I could clearly watch, as Maurice opened the condom packet and rolled a condom onto Bobby Joe’s huge tool. The two of them hugged and kissed deeply and worked each other’s tools until both were fully hard again. Then Maurice stood in front of me, his eyes glued on mine, his hands wrapped around his dick, as Bobby Joe got behind me, pulled my hips back again, positioned his dick head at the entrance of my asshole, and slowly worked the head in.

I was screaming in pain and shock behind my gag, and my eyes were tearing up again. Bobby Joe pushed in a couple of more inches and then his hands went to my butt cheeks, encasing them and squeezing them and pulling them apart, giving him as bigger opening. I lifted my hips as best I could and arched my back, trying myself to widen the opening, knowing that all was lost now and no fight was possible.

At the same time, a little guilty thrill ran through me. All of that dick was going to be inside me. I was turning this dude on. I was being forced, raped, and none of this was my fault. I was both in control of being the object of his lust and being controlled by a hot stud. All of my “what if” fantasies were being brought to life, and no one could blame me for what was happening.

I gulped for breath, pulling as much air as I could through my nose. Maurice saw that I was in distress and said that he’d pull the gag out if I promised to be quiet. I nodded my head in assent, and he ripped the gag off. My mouth now free, I couldn’t help but grunt and whimper at the four inches of dick pulsating inside me. Bobby Joe was going slow. When he sensed my canal opening to him, he pushed in another couple of inches. Six inches in now, and he went into a slow pump, two inches out and then back in two inches. After a couple of minutes of this, though, he came in another inch when he pushed back in; seven inches up my ass now. I yelped when he did this, and his hands went to my pecs.

He stroked my nipples, and I began to tremble and sigh for him, not wanting to do so, but my anger at being violated was being overcome with a new sense of pleasure mixed with the pain. He took his dick in one hand and revolved it in my ass. My ass walls responded by widening to him, and he pushed in another inch. I flinched, but I was managing him now.

“That’s so nice,” he whispered as he brought his mouth to the side of my neck and nuzzled me there. “Don’t you feel it? Don’t you feel yourself opening to me?”

“Yes,” I whimpered softly. “But please, please stop.” But I grunted in vain, as he went in another inch; nine inches now. But of course I didn’t know how far he was in me. All I knew is that I felt totally stuffed and stretched, and my ass walls began to tremble under the strain. I also didn’t know how long that was for any normal person to take until he whispered it to me. “God, I’m almost all the way in, son. Do you know there aren’t many that can take this much of me even after a long time of trying? You’re one sweet bitch.”

I was panting and giving little yelps and grunts with the progress of the last inch he had to give. He had his chest pushed into my back now, and I could feel the wet hairs of his pelt on my shoulder blades. He was giving off a sweaty, musky scent that I found heady.

When I felt his curly pubic hairs tickling my butt cheeks, I knew he was in all the way and assumed that this torture was close to the end. But the ordeal had just begun. He started to stroke me deep then, pulling the head of his cock back to where it rubbed across my prostate and then, slowly at first, and then ever quicker, stroking back into me to the hilt.

No more gentleness now, and Bobby Joe himself was no longer in control. Instinct took over, and he went into a primordial fuck, no longer being sensitive to how new I was to this. But by now, my body had adjusted to him, and the pain was tolerable. At length, I felt him tense and the bulb of the condom fill up, and he just more or less collapsed against me.

30 Days In Jail Pt 2

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7 thoughts on “30 Days In Jail Pt 1

  1. Alex says:

    Hey people, don’t count on the whole story being published. Udatz pulls the rug out and stops publishing in the middle of the story

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