Jane/Joe's Prison OrdealChapter 2 free porn video

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He had been hitchhiking from school to home and was offered a ride by a middle aged man in a pickup truck. The forty-five minute trip started innocently enough, blah, blah, blah, but it soon turned to the sexually interesting ideas of getting a blowjob. The man appeared to be an expert on the whole matter.

He went on about how it was so great to have a hot mouth on your dick. At that point he asked, "Know what I mean?" Joe said, without even thinking about it, "Oh, yeah, ain't nothing like it!" Oh, yeah, what a liar. But a liar whose hardon could now be seen running down his pant's left leg. He was turned on, no two ways about it.

Maybe that's why he mumbled a "Sure." when, a short while later, the man asked him if he'd like to have a good blowing right now. Who knows?

The man pulled the truck off onto a wooded side road and wasted no time in reaching out for the pant's bulge. The first touchy squeeze sent 50 million volts throughout Joe's body. The cattle prod he had accidently touched on the business end one time, just to see what it would feel like, was nothing compared to this.

In the dim moonlight, Joe watched in fascination and pleasure as the man fished his boner out and put his mouth on it.

The man's mouth felt fantastic. It was hotter than hell and wetter than water. And it was doing things he'd never even imagined. Squeezing him hard-like, then soft-like, as it went fully up and down his shaft. Unreal and unbelievable.

Joe only lasted a couple of minutes before he felt the cum just get ripped out of him. He'd never cum this intense before, not even that time he jerked off to a polaroid of Becka Worthington's titties as seen through her bedroom window, a picture snapped by her next door neighbor, Will Turner.

The man sat back in his seat, Joe's cock just hanging out in the air like that, surprisingly still hard, and unzipped his fly. Joe just sat there, euphoric and mesmerized as the stranger's cock appeared. It looked fat and long and untouched by the sun. And it was obviously fully aroused. The man, not even looking at him, said, "Your turn. And do it nice and slow, just the way I did it to you. Don't rush none, I don't like rushers." He reached over and put his right hand behind Joe's neck and bent his head over in the right direction.

Why he hadn't refused, then and there, he didn't know. Maybe it was that old saw he'd been raised with and heard a million times. "Fella does a good turn to you, it's only fair you return the favor." Whatever the reason, he soon found himself with a full mouth of strange cock head.

The man, knowing Joe was a pure beginner, directed him step by step with comments such as, "Now, that feels good, but tighten your lips a bit." And "Move your tongue from side to side on the underside, pressing it in as you do." Joe followed every directive immediately as if grateful for the expertise.

The cock had felt good to his mouth as he, without any shame, sucked the man off. When the man finally ejaculated, Joe knew enough to swallow, but the amount of the load surprised him. Not at first, for it had started very slowly with just a mild dribble. A puddling on his tongue. Then the dribble became a bigger dribble as the man's spasms increased. Then more and bigger dribbles flooded in. The man hadn't spurted as he knew he had, but there was way more of the sticky stuff.

He had swallowed early, but found he had to swallow again. And again. And, lordy, even a fourth time. It was here that the taste of the cum made itself known. It tasted like sweet, but slightly salty, onions. And also made itself evident with a slightly burning sensation in the back recesses of his throat.

Joe had liked it, the getting and giving of oral pleasure, but when the man asked for his phone number as he dropped him two blocks from his house, he had turned him down, with no real reason given. The man had seemed truly disappointed, but he soon drove off leaving Joe to ponder on it all.

But that was then and this is now.

Aware of Sir Cougar's cock in his ass, Jane/Joe struggled to get Sir Thor's trouser off and down to the floor. His wiggling made his ass sensations even more pronounced. He tried to hurry the chore, but it resisted hurrying. As Sir Thor's trousers and boxer shorts finally fell to the man's ankles, Jane/Joe got the full picture of the man's cock and crotch area.

Though it hadn't been obvious when he man had his pants on, Jane/Joe saw the guy had a full hardon. Somewhere between 7" and 8," it had, at its base, zillions of wiry, curly black hairs. For some reason it looked as evil as the man who owned it.

"Suck it! And do a good job!" Sir Thor growled.

A moment later, Jane/Joe had Sir Thor's cock in his mouth, aware of his own full erection that, right now, Sir Cougar was back to fondling and teasing. Sir Cougar fiddled around with the tip, just twice, a few seconds apart, and then stopped. He had used just the right pressure to make Jane/Joe involuntarily moan each time around the hard cock in his mouth.

Jane/Joe didn't want to moan, lord knows, and he knew if he concentrated he could prevent it, but he also sensed that moaning made the sensations seem less. The moans were a relief of sorts. Whereas, he felt, the other path would soon have him climbing the walls and screaming. With whatever cock he had in his mouth at the time.

"Deep-throat me!" Sir Thor barked. Jane/Joe thought of balking, but decided to give the throat spray a chance instead. He found it was easy now to take the man's cock all the way down his throat. His throat felt nothing. His gag reflex had died, too.

Even when Jane/Joe's lips were pressing against Sir Thor's groin and he had his nose pressed against the guy's belly, he didn't feel like gagging. He also felt the man's pubic hairs brush against his nose. It amazed him. Shit, he was deep-throating a large, thick cock and it didn't hurt a lick. With his lips locked around the base, Sir Thor now gave him more instructions.

"Stay way down on it like that to the count of five. Then scoot back up to the head. Work my head a few times and then throat it again for five. And through it all, don't swallow your saliva. Just let it flow out. Remember that, because I want you to do it with every cock you suck from here on in. Now, do the deep-throat routine again and again until I shoot my wad."

Jane/Joe complied. He brought his mouth back up to the cock head, went up and down on it three times, varying just how far past the ridge he would venture, and then deep-throated the pulsing, throbbing member, staying down on it there for five seconds. Then he repeated it. His saliva flowed freely, too. Sir Thor's dick was covered with it, making it slick and slimy feeling. And, for some weird reason, it felt very erotic to Jane/Joe's mouth.

As he sucked, he could feel Sir Cougar's thumb rubbing back and forth over his cock head. It was driving him wild. The sensation was one that made him want to cum, but the damn cock ring prevented that release. It was exquisite and pleasurable torture. And, try as he might, he couldn't extinguish the incessant sensations from his mind. They even seemed to be sending their messages to his mouth as he worked SirThor's sizeable saliva-slick 7+" dick.

As he repeated his deep-throating, Sir Cougar's cock in his ass seemed to get harder, if that was possible. His own cock head had hardened up more, too, if that was possible. It was all having a strange effect on Jane/Joe. He was getting too many pleasant and unpleasant sensations and too many painful sensations, all at the same time.

He was aware of his mouth and his body in ways he had never dreamed about. His mind was getting fucked up. And damn that Sir Cougar with his rub, rub, rubbing! He knew that Sir Cougar knew what he was doing. He was expertly reading Jane/Joe's head movements, body language, and ass twitches to time the thumb rubs. He knew just when to apply them. Just when it would have the greatest effect. To make him so fucking hot he'd suck a gorilla's cock if the ape promised him he could jerk off afterwards.

There was no doubt that it was all having an effect on Jane/Joe. And he knew the men could see it, the changes happening to him. His ass twitching, his erection jumping around, throbbing and twitching wildly, his legs trembling with nervous excitement, his mouth working Sir Thor's erection more and more passionately, slobbering over it--they all gave the game away. He was sucking a cock and they knew he both liked it and hated it. If anyone had told me this two weeks ago... Oooo! His thought died as Sir Cougar's thumb rubbed again.

As his nipples and cock tingled incessantly, adding to the strange and not unpleasant sensation of the hard cock up his ass, the cock in his mouth started to feel very nice. As he worked his mouth, lips, and tongue on the throbbing prick with the very hard cock head, sucking it and deep-throating it, saliva flowing, with Sir Cougar moaning loudly above him, he felt sexually aroused and horny. And he didn't understand why he couldn't control himself. Why his resistance was breaking down from mere sensations. Mere? No, he thought, they're far from being mere!

As the action heated up, Sir Bruiser said, "Jane! When Sir Thor is gonna spurt, put both your hands on his ass cheeks and pull him to you. You unnerstan'?" Jane/Joe nodded as he went up and down on Sir Thor's hot penis. Sir Bruiser added, "And I want you to remember to do that with each guy that comes in. Hands on their ass cheeks when they shoot. Unnerstan''?" Again Jane/Joe nodded on the thick, slobbery-wet dick.

Then Bruiser had another idea. He bent down and looked at Jane/Joe's face. "Open your eyes, Jane!" Jane/Joe complied. "Closing your eyes is an insult to whomever you're sucking! So, keep your eyes open at all times. Someone will be taking peeks at you from time to time and it's shit eating time if you get caught with them closed. OK?" Jane/Joe nodded up and down on the dick, his eyes wide open.

He was now staring at wiry pubic hairs and he could see the shaft clearly as he sucked away. If he needed a reminder that he was sucking cock, this sure did the trick.

In wasn't too long before Sir Thor started to tense up. Jane/Joe knew he was going to cum soon. Heeding Sir Bruiser's words he reached behind Sir Thor with both hands and grabbed and squeezed the ass cheeks, then drew him toward his mouth. A moment later Sir Thor's cock erupted.

Sir Thor pushed his cock into Jane/Joe's mouth so only the head was inside. At the very same time Sir Cougar tickled his cock head-- fiercely. As Sir Thor's cock twitched, spasmed, and spurted it's hot cum, Jane/Joe moaned deeply. "Mmmmm!" Damn that Cougar! The saliva in his mouth added to the copious amount of cum coming in and Jane/Joe was fearful he would gag and have to spit up.

Remembering Sir Bruiser's admonition, he forced himself not to gag. Though a very rough struggle ensued, he swallowed every drop, gurgling and sputtering to be sure, but not missing a thing. His eyes threatened to close up on him, but he forced them to stay open.

He could taste the cum and yet he couldn't. Not fully. Too much was happening to him and he had way too much saliva in his mouth.

He was ordered to keep sucking until it was drained and told to stop. A short time later, Sir Thor pulled his moist limpish cock from Jane/Joe's mouth. It flopped out with a shlooshing noise.

Sir Cougar, that bastard, moved his thumb across the tip once more. Then stopped. Oh, God, thought Jane/Joe, how much more of this can I take? The thought of 60 or more guys drove his mind into a tizzy. He swallowed loudly and tasted cum in the back of his throat. It burned slightly. And it burned with each and every swallow, reminding him that cum was there and had just been swallowed by him.

"You know, Sir Bruiser," Sir Thor said, pushing his dick back into his trousers, "This bitch has potential!" He laughed.

As Sir Thor made his exit, the three remaining men in the room also laughed. Joe didn't. He just sat there, impaled on Sir Cougar's stiff prick, with mixed feeling running through him. He now had nothing to do but wait for the ordeal to resume itself with the next man to cross the doorway. He didn't have long to wait. Oooh! You bastard! Stop that! Leave the fucking head of my cock alone, all ready!

One by one, one after another, the men arrived. One after another, Jane/Joe sucked their cocks, deep-throated them and swallowed their salty-tasting, burning cum. The taste of cum was inescapable to Jane/Joe's tongue. The taste was everywhere in his mouth. It coated his teeth. His gums. His tongue. And it burned itself deep in his throat. His mouth felt awash in it. He could have used a little water to help wash it down, but he knew that it would be futile to ask. They wanted him to suffer. There would be no water coming his way. Water? You don't need no stinkin' water, not when you got delicious cum to drink. Yeah, he could hear them now.

The third guy brought a scary realization to Jane/Joe. As much as he hated to admit it, that damned Sir Cougar's cock felt good! Very good. He had the overwhelming urge, and a great desire, to just surrender to the good feelings and start bouncing up and down on the man's big prick. Wildly, as a wanton slut might. But as nice as he knew it would feel, he refused to let it happen. He didn't want them to see him like that.

However, he did make one small concession to the sublime sensations. He went surreptitiously up and down on Sir Cougar's cock with an up and down movement so miniscule he felt sure no one could detect what he was up to. Not even Sir Cougar. He tried to make it appear that it was part of his normal movements. And, oh God, it felt sweet! So much so that he found himself, at times, beginning to increase the length of his up and down moves. Whenever that unwelcome event happened, he would immediately go back to the tiny moves.

He was doing this routine again with the fourth guy, too, but something occurred that scared him a little. On one of his downward pushes, a tiny push to be sure, he felt the truly unmistakable repeat spasms of Sir Cougar's prick. Oh, oh, he thought, I've made him cum!

Would that please him or piss him off? He tried not to move. The spasms were numerous, too. Seven? Eight? More? He didn't know, but when Sir Cougar stayed in him for some minutes after the last one had come and gone, and didn't push him off of his lap, he felt it just might be okay.

Around five minutes later or so, Sir Cougar's spasms started again! Right after a fresh miniscule up and down movement by him. He ain't cumming again! He thought. No, it was obvious to him now. Sir Cougar was sending him Morse code! Of a sort. He was letting him know that he knew about his little miniscule up and down secret. The bastard! Just too fucking clever by far. How long had he known? Probably from the gitgo, he surmised.

Why hadn't he said something about it to the others? They would certainly get a big kick from knowing. Perhaps Sir Cougar was making it their little secret to inspire him to keep doing it.

Well, fuck it, he thought, if that's the way he wants it, fine. He now felt he had slightly more freedom with the man, a silent permission of sorts, and could now increase the distance of his up and down excursions, which he knew would make it feel much better. But he didn't want to make it public knowledge, however, so he merely went from miniscule to an inch each way. Oh, God, he thought, this is fucking heaven--on a man's lap, no less!

Sir Cougar kept up his cock spasms here and there with timed variations. Pulse, pulse, Pause. Pulse. Pause. Pulse, pulse, pulse, Pause, Pulse and so on. Morse tapped out with a penis.

Just for shits and giggles, on one of Sir Cougar's spasm episodes, Jane/Joe used his ass muscles and squeezed back. His ass executed a sequence of squeeze, squeeze, squeeze, pause, squeeze, pause, squeeze, pause, squeeze, pause, squeeze, squeeze, squeeze. Any old salt would easily read this as... - - -... and translate it to SOS. Save Our Souls or Save Our Ship, take your pick. Jane/Joe almost let out an audible giggle at his cleverness.

Then Sir Cougar surprised him by pulsing right back with pulse, pause, pulse, pause, pulse, pulse, pulse, pause, pulse, pulse, pulse. Unless Jane/Joe was mistaken, the man had telegraphed ASS with his cock! What fun!

Throughout the night, and with each and every blowjob, the pulsing gibberish from both parties involved continued. As did Jane/Joe's up and down movements on the stiff, 10-1/2" cock rammed fully and snuggly up his ass. Accompanied by Sir Cougar's sexually arousing thumb foolery and Jane/Joe's audible moanings. If Sir Bruiser and Jose noticed anything different in him, they were keeping it to themselves.

And, as he sucked each cock, his eyes wide open, he had the clear vision of the many different kinds of public hair available. And he could see the cock shafts disappearing somewhere below his eyes as he deep-throated each man. In some cases, he could actually see the man's balls rise up, just seconds before his ass grabbing and cum swallowing act.

How many dicks so far? How many to go? He had no idea. It had to end before he was eligible for Social Security, didn't it? Maybe not.

And, as he sucked, Jane/Joe couldn't help but let out those moans from time to time. They were forced out of him by Sir Cougar's thumb manipulations. And, every now and then, his thumb would leave the cock head's tip to explore that super-sensitive area on the underside of the head where the two roundish hemispheres come together, the area known as the glans penis.

Whenever Sir Cougar touched the blessed glans penis area, Jane/Joe went wild. His ass, his body, his head, and his legs, all involuntarily twitched and he was forced to moan throughout a shudder. It was involuntary and he had no choice about it, he knew, but he felt embarrassed knowing it appeared he was enjoying sucking each dick. Which he sure wasn't now, was he?

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Most Convicts enjoy... secretly or otherwise... the occasional bitch... who gets sent to Colefax... or any other jailhouse... prison... or incarceration facility... who arrives already on hormones... halfway through her own sex change... or just before the final cut anyway... as you overhear the lewd commentary... and casual conversation... about sex... and what Most Men only talk about anyway... "hail... iffen uhh white bitch gonna go tuh awl dat trubble... jest tuh bee uhh bitch... den...

3 years ago
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Jerry In Prison Part 1 Warden Polinski

About seven months ago, Jerry and four of his buddies, drugged out and drunk, had driven up to a convenience store/gas station. Through his buzz, Jerry knew that he was about to do wrong, but he could not control himself for being so fucked up. The five men put on ski masks and bandannas, grabbed guns, and burst into the store, shooting bullets into the air to make everyone inside get down. One of the men had gone right up to the cashier and demanded money. Little did the robbers know that a...

2 years ago
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Deputy MorpheusChapter 6 Prison Escape

I glanced up as the commander stepped into the room and everyone quieted. He looked at me, “Morpheus, take Swift, Taylor, Samson, Adams and Michaels. They had a prison escape on Devlin.” I nodded and stood, “How many?” He shook his head, “Nine.” I grabbed my bag and started towards the lifts. The other marshals followed me as I dropped to dispersing. We had a four hour wait in the starport before boarding a shuttle up to the cargo transport that was headed to Devlin. There were only a few...

4 years ago
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Lesbian Femdom Stories The Japanese Prison Camp

Part 1 The Prison CampThe Japanese Lieutenant looked down at her prisoner. She was happy to see her stretched out, naked on the ground. Arms and legs all secured tightly to the wooden pegs which were standing erect from where they had been knocked deeply into the sand that lay beneath. ?You slut!? She screamed. ?You think you make fun of Lieutenant Nashiba and get away with? You think Lieutenant Nashiba a easy touch, you do? You must learn some manner, girl. I teach you manner now so you know...

3 years ago
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A Prison Story Part 1

CHAPTER 1 - The New Punk By JIMMY SEAY 27 year old Brian Butler was a fit muscular man. While his face was considered ruggedly handsome by some, his body was what had gotten him his choice of women on the streets. At 5 foot 8 inches, the 180 pounder was a cut and chiseled mass of beefy rippling muscle. He had broad shoulders, strong arms, meaty pecs, a ripped washboard 29 inch waist, big strong legs, and a butt that could fill out any pair of pants known to man. Women had been...

1 year ago
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Prison Props

He's making you... with frequent Pimp beatings... slightly cross one eye... or both eyes... always... while you're attempting to address... speak to... or even respond to a question or remark from certain Men... the crossed eye(s)... makes you look slightly stupid... somewhat clueless... and decidedly... intellectually disenfranchised... even bimboish... which makes it even easier for Men... to lean in... much sooner... and more quickly... and take advantage of you... you're forced to...

3 years ago
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Prison Wager

"Convict!" the guard yelled into Tom's cell. Tom looked up from his bunk at the large prison guard looking down at him through the bars of his jail cell. Tom Waters is in prison for embezzlement. He answered with respect. "Yes, Mr. Roberts." "I see your wife was here for a visit." Tom nodded his head. "Yes, Mary was here." The large guard replied. "I know because we like seeing her cute little ass as she strolled out to that shit box of a car that she now drives. That's a shame....

3 years ago
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Letter from Prison

Dear family. This is my first letter from prison. They said that they would mail it and I could write anything. I hope you receive this letter. I will be blunt and honest with you. You know why I am here so we'll not talk about that. It's been three years and I've had plenty of time to reflect. You need to know what it's like over here. Not that you can do anything about it. I doubt you'll ever read this letter. They won't mail it bit I will write it anyway.I am locked in a 6 foot by 6 foot...

4 years ago
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Fucked in Prison PT2 Gay

I sometimes struggle to remember why I married Melvin in the first place, since I had my pick ofnumerous athletic and handsome men. It was probably his outgoing personality and intelligence thatoriginally drew me to him in college, but he is not now, and never has been a man’s man. But I hadthe feeling that he would be successful and able to provide me with the finer things in life. We were doing very well, with a beautiful home on the Hudson River, when he fucked up and gotcaught bribing a...

2 years ago
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Prison Bitch

*********************************************************************** Note to Readers, this story contains racial stereotyping. If you do not like this do not leave a comment saying so...JUST DON'T READ IT *********************************************************************** Of course I dodge my taxes everyone does, it's the American way. Of course all the big businesses dodge taxes in fact with their high paid lawyers it's doubtful most pay any taxes at all! So I failed to...

2 years ago
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Prison Raid

I joined the army when I was seventeen. Han had a basic course and a few advanced courses but all officers had to go to Genta. When I came back it was three months later and as a second lieutenant in a combat team. Two years and I was a captain in the Han rangers. My company was more a large platoon and I was the only officer. With the new advance into Clar, fighting was fierce and we were getting more and more hidden bases behind our lines. When we got the recon report of a company of Rus...

2 years ago
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Prison Cum Control

It is almost time for Travis Kellys second punishment session with Dr. Gerard. He had a difficult two days with the chastity device. Although it took some getting used to, he had little trouble voiding his bladder while squatting on the toilet. It was embarrassing but doable. However the erections were another story. Unbeknownst to him, he has been loaded up with various sexual stimulant d**gs. They are designed to not only boost his sperm count and increase his production of cum, but they...

2 years ago
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Prison Cum Control

It is almost time for Travis Kellys second punishment session with Dr. Gerard. He had a difficult two days with the chastity device. Although it took some getting used to, he had little trouble voiding his bladder while squatting on the toilet. It was embarrassing but doable. However the erections were another story. Unbeknownst to him, he has been loaded up with various sexual stimulant d**gs. They are designed to not only boost his sperm count and increase his production of cum, but they also...

2 years ago
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Prison School Ch 01

Chapter 1 – Week1 – Monday Morning - Arrival and OrientationARRIVALThe four boys were getting pretty restless after the three hour long ride from the state penitentiary to the prison school, as it was called. The state had contracted with the training school to take minimum security inmates that had at least  one year to serve and train them under an apprenticeship program to become employable and certified skilled construction workers.They were all fitted with special bracelets that were not...

Gay Male
2 years ago
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Prison Story

Life can be sweet until you fuck up. Life was going great for Michael Brand. He was living the high life. He had beautiful girls following him around. Nice cars and a cool house. He wore fancy sneakers and all the cool hoodies any guy would want. He loved designer clothes and living the high life. Michael had the greatest parties. Everybody who was anybody went to them.Michael was a drug dealer. He'd been selling drugs since he was eighteen. He made friends with somebody who was in the mob....

Gay Male
2 years ago
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I am a Prison Bitch Now Gay

Life can be sweet until you fuck up. Life was going great for Michael Brand. He was living the high life. He had beautiful girls following him around. Nice cars and a cool house. He wore fancy sneakers and all the cool hoodies any guy would want. He loved designer clothes and living the high life. Michael had the greatest parties. Everybody who was anybody went to them.Michael was a d**g dealer. He'd been selling d**gs since he was eighteen. He made friends with somebody who was in the mob....

2 years ago
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A Wife a Prison Officer

1st attempt comments welcome Firstly let me say I was a normal housewife, Happily married and had not a clue my Husband of 5 years was anything other than what I then percieved as being normal. To cut a long story short I found some internet sites he had been browsing and several floppy discs of images I should have found shocking but strangely didnt. These were images of females being brutal to males, Not your glamour girl types either just normal females stacking a few pounds...

2 years ago
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Prison Camp

This is the first chapter of a very long story, with connection to a North Africanprison camp. In this first chapter we follow half a day in an inmates life.She has been there for a long time, and through her we get a impression ofa modern prison system for foreigners in this region.    The story of Linda and Lajla Hard labour The whistle sounds and 311991 lets herself drop hard down on her knees, puttingdown the heavy sledgehammer carefully at her side. She knows that toolsare much more...

3 years ago
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Prison Love

I never expected prison to be like it was. Sure, I had heard all the stories about **** in prison, and the gay guys, but I never, ever believed it. I would always laugh, and punch them. But then, I got into real trouble. It was the day I took a chair and threw it, and it shattered, blinding a person by hitting him in the eyes. I got three weeks in prison and then 40 hours community service. I was very stressed.So, I was practically being dragged down the dark, murky hallway of the prison cell,...

3 years ago
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Prison Love

I never expected prison to be like it was. Sure, I had heard all the stories about **** in prison, and the gay guys, but I never, ever believed it. I would always laugh, and punch them. But then, I got into real trouble. It was the day I took a chair and threw it, and it shattered, blinding a person by hitting him in the eyes. I got three weeks in prison and then 40 hours community service. I was very stressed.So, I was practically being dragged down the dark, murky hallway of the prison cell,...

3 years ago
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Prison Prey

Nathan was a pretty gay boy who loved attending to college. School life had been far too stuffy for him and being a bright student, he was far happier being left to his own devices. Unfortunately, his life was about to change dramatically, due to a very cruel twist of fate. The college had been plague by drug problems in recent times and everyone one in authority, was sick and tired of all the hassles. Unbeknown to Nathan, during one of the regular raids someone had offloaded their stash into...

Gay Male
3 years ago
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Turning Gay in Prison

Just after my 19th birthday in the winter of 1993 I found myself in trouble with the law.I was arrested for selling dope and stealing a car with a friend. I was released on bail and two months later I was in front of a judge for sentencing, my lawyer and the crown attorney agreed to a 90 day jail sentence and probation, but the female judge had a different idea, she sentenced me to 30 MONTHS in prison I almost puked on the spot!I had been to jail before but only for very short time, 90 days...

3 years ago
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New to Prison Lesson 1 Gay

James had never had to share a room with another man in his life. He'd never had a brother, he'd lucked out for his first year of college and snagged a single room, and then his whole life had changed. The guards escorted him down the halls, the sound of men stomping their boots and smacking their cell bars following him. James hung his head, his blond hair falling into his face. He was - or had once been - a cute college k**. He was a little nervous, a little bookish, his frame slender and...

4 years ago
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Prison Bitch 1

James had never had to share a room with another man in his life. He'd never had a brother, he'd lucked out for his first year of college and snagged a single room, and then his whole life had changed. The guards escorted him down the halls, the sound of men stomping their boots and smacking their cell bars following him. James hung his head, his blond hair falling into his face. He was - or had once been - a cute college k**. He was a little nervous, a little bookish, his frame slender and...

4 years ago
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Prison Bitch

James had never had to share a room with another man in his life. He'd never had a brother, he'd lucked out for his first year of college and snagged a single room, and then his whole life had changed. The guards escorted him down the halls, the sound of men stomping their boots and smacking their cell bars following him. James hung his head, his blond hair falling into his face. He was - or had once been - a cute college kid. He was a little nervous, a little bookish, his frame slender and...

4 years ago
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  • 75
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Kareems BBC Prison Cock Pt1

I'm the prison guard and Kareem Mwangi is the prisoner, so you would have thought I had the upper hand, and until a few weeks ago you would have been right.When I first heard of the trailer addition to the prison I was furious. A few states permit conjugal visits and the prisoner has to be married (just for a start) before his application to schedule one is approved. The prisoner requests a block of time and the Warden has final approval, but giving prisoners any sort of privileges is something...

2 years ago
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A Lonely Night On Prison Duty

HMP Wormwood Scrubs (Her Majesty's Pleasure) 1145 Hours, Dee's Night Shift.It was a lonely night for Dee. She was on prison duty tonight and she knew why. She had rejected the advances of her overweight, slimy boss, David, who would not take no for an answer, and when he was told otherwise, knew how to make her come around: night shift in the men’s quarters of the prison.She was beautiful, her long, red hair hung around her shoulders and neck like a burning flame. Her piercing hazel eyes bore...

Love Stories
3 years ago
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Prison Break

It was stiflingly hot day. Ken and Jill had spent it at the beach where they'd met fifteen years ago. Back then, Ken had proudly shown off his trim figure with tight swimming trunks. These days he kept his burgeoning beer gut covered with a pale summer shirt. But the day beach had taught him one thing—his wife looked as good in a bikini now as when she was a teenager. Maybe even better. He sat in bed, propped up against the headboard, naked from the waist up with the bed sheets folded back to...

2 years ago
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Prison Pimped BBC Gay

It was around 9 pm on a Friday only two weeks past New Years in 2001. I had been in prison over 4 years with eleven months to go. After my release I would have served 5 years and 45 days. During my incarceration I had seen men stabbed, beaten, killed, pimped out and gang ****d. You learned to keep your mouth shut. Snitches did not live long. I did not belong to any of the prison gangs or groups. Being a white inmate without affiliation, I knew I lived on borrowed time since the beginning. I had...

4 years ago
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Prison Story

Life can be sweet until you fuck up. Life was going great for Michael Brand. He was living the high life. He had beautiful girls following him around. Nice cars and a cool house. He wore fancy sneakers and all the cool hoodies any guy would want. He loved designer clothes and living the high life. Michael had the greatest parties. Everybody who was anybody went to them. Michael was a drug dealer. He’d been selling drugs since he was eighteen. He made friends with somebody who was in the mob....

1 year ago
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Wife protects you from bull in prison

Author's note: Hey reader, this is my first story. Hope you like it, if you have any feedback, let me know! For now, enjoy! "Smack, smack, smack", the sound of crotches slapping each other in prison surrounds you. The most beautiful woman shouts, “Fuck my white pussy”, she moans as she grinds all the way to the shaft of the black gang leader. She gets thrown with her stomach flat on the bed. She spreads her legs and you see her beautiful wet pussy. The big black brute takes place behind her...

4 years ago
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Pretty Pinky Life Of A Sissy In Prison

Two inmates walk from the cellblock to where a correctional officer sits at a desk. The C.O. is a middle aged black guy. One of the inmates is a buff black guy; the other is a small slightly built young, Caucasian. The black inmate is dressed in standard prison garb. He has the Caucasian by the upper arm - the way a man walks a woman - and is walking him to where the C.O. sits. The Caucasian has on brown work boots with dark socks rolled just above the tops. He has a towel tied around him,...

3 years ago
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My Big Powerful Negro Bruno Day out from Prison w

...At last after a few months inside and behind those solid bars. my hung stud Bruno was allowed to come outside for his day with me. Of course he was shackled to a guard and wore a GPS tag on his ankle!It now all meant I did not have to see Bill, that is hubbies mate who was in prison 1st as a visitor, using Bill as the excuse to go over there.No I could now see Bruno outside the prison, OK, with his guard there!Most of the more intimate meeting outside were in a park about 10 miles from the...

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