No Luck in Jail

Kyle's prison assault continues, as he begins his anal punishment... and awakening.

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  • 10 Min Read

As I stood under the hot shower, my sore body relaxed and unkinked itself. 24 hours earlier, I was a normal horny 18-year-old, finishing high school and having fun. But I messed with the wrong girl, and now her cop father was punishing me by throwing me naked in a jail away from my hometown, a sex toy for the hardened Black and Hispanic criminals to use.

I scrubbed the cum and piss from my chest and face, closed my eyes as the water cleansed me. I was starting to feel like a human again.

No luck.

“Hello.”

Startled, I jumped at the voice from the entry to the showers. Standing there was a short Asian guy, probably early 30’s, already partially undressed. “Hello,” I replied.

“They sent me in here to get you prepped. I doubt they plan on waiting too long so best we get started.” With that he completed his garment removal and walked naked towards me. “I’m Han, by the way. They said you’re the new meat right now, broke your throat in last night?” The lilt in his speech implied a question, but he clearly already knew the answer.

“Yea” was all I replied.

“OK, well now we got to get that bussy ready.” He reached out and grabbed my ass cheek, squeezing it a bit.

“Hey! Hands off!” One on one I felt some bravado. It didn’t last.

“Sure, sure, no need to get mad at me. I’m just like you, a cell-block pussy. But if you don’t want to get hurt too bad when they start fucking you, then best you shut up and listen to me. OK?”

While I had no desire to be fucked, I knew it would soon happen in this hell, so I simply agreed with a nod.

“Good. OK, this shower over here is what you want.” He took my arm and moved me over to a shower at the entrance. It was the only one that had a handheld showerhead clipped to the wall. “This is for use by injured or chaired inmates. Got to be ADA compliant, LOL.” He unscrewed the head off so that water could spill from the end. “OK, so you need to clean out you ass-pussy so the men don’t get dirty. If they get dirty, they will hurt you, or hurt you more. Bend over.” He gestured at me, and I reluctantly turned my butt to him and tried to touch my toes.

“You just need to get the water flowing a bit, not too strong, then you insert it like this.” As I watched from over my shoulder, he soaped up the end of the handle and started to slip it inside me just a bit. I could feel the water filling me up. “Hold it in. Your instinct is to push out, but you need to get enough in first. Then when you feel full, drop the handle out and rush over to the toilet there and expel.” I did as instructed, running and emptying my bowels. As I returned to him in the shower, he was smiling and holding the handle towards me.

“Perfect. Now do that again and again, until you only shit clean water. And hurry, because they’re going to come get you soon. Best you be fully ready.”

He turned to get dressed and leave. “Wait, please. One question.” He turned back to me and nodded. “Does it hurt, like bad?”

He let out a huge laugh. “They are going to rape you, over and over. Not make love, not even have sex. Rape. They are going to force their big cocks inside you, over and over. Of course it’s going to hurt! A lot! If you’re lucky, maybe, you’ll find you enjoy it. I hope for your sake you never get to that point.” With that he snatched up his clothes and scurried away.

Despite not wanting to, I got myself prepped for the upcoming ordeal. Best not to give them a reason to hurt me. But it was humiliating, making myself complicit in this abuse.

I dried off and walked out of the bathroom to find two of T-dog’s men waiting and smiling.

“Follow us, pussy.” They turned and walked back in the direction of the empty cell from last night. I followed sheepishly.

Waiting in the cell was T’, also grinning, and buck-naked. He was reclining on the lower bed, pillows behind him, smoking a cigarette. His huge flaccid cock was displayed. He reminded me of some X-rated Jabba the Hut. “Alright, cuntboi, hope you got re-energized, LOL. You gonna be a busy beaver today.”

“Yes sir.” I replied, standing in the doorway.

“Well, whatcha waiting for? You had the snacks, time to get the full meal deal. NOW!”

There was no doubt as to what he wanted, so I crawled onto the cot with my head at his enormous tool. He began to slap my face with it, it’s size enough to go from my chin to my forehead.

“Yeah, that’s what you been working up to… get those balls in yo mouth, boy!” I immediately opened up and began to tongue-bath his large nuts. I knew it was in my best interest to please this mountain of flesh. He controlled how much abuse I would get in here, and though he had shown no inclination to be nice, being a good ball-licker and cocksucker certainly couldn’t hurt. The thought alone made me ashamed.

“Ummmm, yeah, that feels good. I bet you already knew your mouth was made for serving black dick. You probably been dreaming of it, at night when you touch yourself, haven’t you?” I said nothing, just continues my licking. That wasn’t the correct response, because he grabbed my hair and pulled me up, mean eyes staring at me. I felt one of the henchmen behind me grab my nuts and squeeze. “When I ask you a question, bitch, you better respond.”

“Yes sir, sorry sir.” I squealed.

“Alright. Now tell me, did you dream of tasting black dick?”

“No sir.” Wrong answer. The guy behind pulled my torso up to him, and T’ punched me in my balls.

“Really? You a slow learner, ain’t you? Stupid cunt.” He punched me again, this time in the belly.

“Now, tell me how much you been dreaming of getting that pretty mouth on a big black cock like mine.”

The sexual abuse wasn’t enough; they wanted me to pretend to want it. Bastards! But I had no choice, as the punches had made their point quite well. “Sir, I wonder every night what it would be like to suck on big black cocks. Please, can I suck yours?” My voice was flat, but the words were what he wanted.

“OF course you can. Get down there and put that tongue into gear.” I crawled back down between his legs and wrapped my lips around the big mushroom head of his cock, already leaking pre-cum. I tasted the salty spooge and opened up to swallow more of his shaft. This was different from most of last night, as then my mouth was more of a passive vessel for their thrusts. Now, T’ was allowing me to explore his cock at my pace, reveling in my subjugation, knowing that I would try and please him out of my own self-interest.

And explore I did. I was a smart and adaptive guy, and now that I had some sleep and time to think, I had given myself some intellectual armor. I had wanted Janet to suck mine, and girls generally did it all the time, so it would be hypocritical to think of it as disgusting. Why would I want my girlfriend to do something disgusting? No, it was just part of sex, flesh on flesh and mouths on body parts. While I had no desire to actually suck cock, I had no desire to eat her pussy either, but I had been willing to do it, as part of the price of sex. I was bullshitting myself and I knew it, but it helped nonetheless.

Despite my revulsion, having the veiny shaft in my mouth was a curious experience. I knew gay guys enjoyed sucking cock, so I just let myself get into it. It was more enjoyable than the forced face-fucks of last night, so I slurped along the meaty black shaft, licked his balls, and generally gave as great a blow job as I could. My jaw muscles had grown last night, and they had broken my gag reflex completely, so I was able to sink my face all the way down and bury my nose in his pubes. I alternated doing that, licking the sides, and slathering his balls. I could tell he was enjoying it from the sounds and words of encouragement he was sending my way.

“Yeah, baby, that’s right. Suck all of T-dog’s cock. Look at you go, taking that all the way down! I knew you were a natural. MmmmmmHmmmmmm, that so good.”

Despite myself, I actually appreciated the encouragement. I found I wanted to please, my nature was to try and excel at whatever I was doing, whether sport, school, or, it seemed, sucking cock.

“Damn, I could have you suck me for hours, that mouth so good. But I got things to do, so time for you to get your reward. No more back and forth, just up and down that shaft boy.” I did as instructed, bobbing up and down the cock as fast as I could, swirling my tongue as I went.

“Oh yeah, that’s it baby, you gonna get my load for sure now. Uuuuggggghhhhh!!!!” He let out a roar and shot a firehose of cum in my mouth and down my throat. Amazingly, I swallowed it all, even milking the last drops from him.

“Hot damn, seems we got your mouth-pussy properly trained. Now my fellas are gonna break the other end open,lol.”

T’ got up and flipped me onto my back on the cot, then stepped back as his two henchmen, who had been standing by, watching and jacking, moved onto the bed. One got at my head, his junk in my face, and held my legs back to expose my clean hole. The other pulled out some lube from somewhere and started to finger me, two fingers working the lube inside. T’ just stood watching and smiling.

“JT won the bidding last night, so he gets to pop your cherry. Then Mugs here. After that, you’re open for business, both those sweet holes. I’ll be back a little later, to properly fuck you with my beast once they opened you up enough. I like a sloppy hole.” Grinning, he left the cell.

I had come to terms with the blow jobs, but hadn’t been able to intellectualize my ass getting broken in. Nevertheless, JT was about to take my virginity, already having three fingers working in and out of my hole. It felt strange, them wiggling around, but not unpleasant. Then he found his goal, my prostrate, and began massaging it with a finger. Boom! “Fuuuuuck, that feels good.” I said out loud.

“Yeah, I found your honey spot. Now I know where, we gonna rub it with the big stick. LOL”

He pulled his fingers out and immediately his mushroom head was pressing against my anus. He slipped in a few inches, causing me to wince aloud, and he stopped for a few seconds while I got used to him. I was surprised he was being so kind, but knew that would be hit or miss going forward with these thugs. Another couple of inches pushed in, rubbing my ‘honey spot’ again. I moaned, clearly in pleasure not pain, and heard a chuckle, followed by a final push filling my ass. I opened my eyes to see JT’s face grinning a few inches away.

I felt him slowly back out, then slide in, over and over, slowly but persistently, all the while smiling at me. The inner massage actually felt amazing, and I couldn’t help myself expressing my pleasure.

“You like that dick, don’t you white boy.” It was a statement not a question, and I answered truthfully. “Yes Sir, it feels fantastic.”

“Uh huh. Now that you’re hooked, the real fun begins.” He started fucking harder, with longer faster strokes, really going for it. While my inner ego was ashamed by this, my sex drive wasn’t listening.

Soon JT exploded inside me. I felt the pulsing of his cock shoot several times. That felt good, not like the rape I had been expecting. Hopefully all the fucks would be like that one.

No luck.

JT slipped out, grabbed my ankles, and spun me around 180 degrees so that the other thug, Mugs, could take his turn. Mugs smacked my ass, hard.

“That took too long. JT must be sweet on you, bitch.” Without warning he shoved forward, sinking most of his cock inside me in one quick thrust. I yelped out in pain. “Shut the fuck up.” Mugs pushed forward and began to relentlessly piledrive my ass, folding me over like a pretzel practically. This fucking hurt, but there was still an undercurrent of the pleasure coming through; my brain was so confused by the contrasting sensations.

“Fuck, this is good boy pussy here! Still nice and tight. Won’t be in a few, LOL.”

Mugs punished my hole with his cock, causing as much pain as pleasure inside me, But soon he also shot deep inside. I guess all that back and forth got him shooting fast. He slipped out and dropped my legs to the cot as he got up.

“I got to get to the gym. Fix him up for the others.”

I looked up at JT, who was nodding affirmative to Mugs. “I will. Most guys here won’t want him looking at his face, so I’ll get him ready to doggy.” He helped me up off the cot, turned me briefly to the cell door. I gasped, there was already a long line of criminals waiting to fuck me. “Please no,” I whispered.

“Yeah, they all gonna turn you out like a proper bitch.” He smacked my ass and grinned.

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