Timmy's Prison Cavity Search Ch. 04 free porn video

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After Sheba pumped her spunk into Timmy's suck hole and had him swallow her load, she shaved him smooth and hairless like a woman should be. She then dressed him up in a patchwork of lacy lingerie similar to the way Madonna used to dress when she started her career. She even put a bow in his hair and had him put on the lacy fingerless elbow length gloves. A lacy garter held his fishnet stockings thigh high for a nice sexy effect. There was no need for a skirt or panties. They wouldn't be on long enough for the bother.

When Sheba walked him back out and reintroduced him to Kong and his crew of gangsters, no one could believe their eyes. No longer could anyone possibly think of Timmy as a man. That wasn't even an option. The only thing that even hinted of masculinity about him was his hard little two inch pecker shamelessly pointing straight ahead like it was telling him which way to go. It danced around like a little puppet whenever he would take a step. There was no sign of male left in Timmy's appearance except for that little thing and that didn't really matter to anyone except maybe Timmy. Timmy had been transformed into a pretty girl. Granted he was a flat chested, shapeless girl, but lots of pretty little prison girls were that way until some big strong prison daddy decided to start feeding them hormones or inject them with silicon in all the appropriate places. Timmy was soft, smooth and pretty with a delicate fragile body and that was what mattered in the beginning. Everyone was speechless, even Johnny for once. Johnny kind of stared with a mixture of shock and lust. Then Sheba introduced Timmy with the announcement of his new name.

"Meet Tiffany, everyone. We'll call her Tiffy for short," Sheba said. It made Johnny snort out a laugh and mimic the name. It made Timmy/Tiffany put her head down in shame. Kong approached her and took her chin gently in his hand. He lifted her head and forced her to look up into his eyes.

"Is that little white monkey bothering you, Tiffy darling?"

Tiffany rolled her eyes sideways at Johnny who nervously backed up and stared in disbelief. "Maybe a little," she said with a shrug.

Kong let go of Tiffany's chin and stomped over to Johnny. "Get over against the cell wall and stand in the corner."

"Are you serious?"

"Either stand in the corner with your pointy nose stuck to the wall or Sheba is going to take you into the back and fix you up nice and pretty so you can join us."

"I... I'll just leave, okay?" Johnny asked.

"No, it's not okay. You have two choices. Pick one."

Johnny hustled over to the corner of the cell and pressed his nose into it.

"That's right, boy. Press your nose right up against it. And close those fucking eyes and keep them shut. You know the drill, boy! Don't make me take off my belt!" Kong reached for his belt and Johnny trembled. Kong turned back to Tiffany with a wink. "Is that better, baby?"

Tiffany wasn't sure how to answer.

"Of course it is," Sheba cut in, wrapping her arms around Tiffany and licking her ear. She was actually cutting Tiffany off before she could answer to make sure she said the correct things. "I'll bet she wants to thank you for getting rid of that annoying little shit but doesn't know how. You can just give him a little 'thank you', baby. That's all Daddy needs."

Sheba smiled at Tiffany and Tiffany took the hint. Tiffany glanced at Kong, "Thank you, Daddy."

"That's alright, Princess. I'm sure you'll be showing me how grateful you are in a few minutes here."

Tiffany looked to Sheba for guidance. Sheba slid down Tiffany's torso to her knees and took Tiffany in her mouth. Tiffany gasped. She thought for a moment Sheba was about to return the favor Tiffany had done for her in the rear cell moments ago. She was, actually, in her own way, just not yet. Sheba brought Tiffany to the edge only. Then she wrapped a piece of twine tightly around the base of Tiffany's cock before she could cum. In addition to making her unable to cum, it kept her hard without the possibility of going soft.

"This will keep you right on edge. We heard about you and that female officer and Daddy doesn't want you cumming too quickly."

Tiffany heard Kong behind her. He was unfastening and unzipping his pants. She heard the material drop to the floor. She watched the pants slide forward past her feet as Kong kicked out of them and scooted them out of the way. Tiffany started to turn her head to glance back over her shoulder and get a good look at Kong's cock, but Sheba popped up and grabbed her face and kept her looking straight ahead.

"Don't," Sheba warned. "If you see it before you've had it, you'll be too afraid to take it and it will make the pain worse. Just look at me and lean backwards. That's right, just like that. You're doing great."

Tiffany felt it now. It felt like someone was trying to force a baseball bat up her tight asshole. She started to scream and Sheba slapped her face. Sheba grabbed Kong's pants from off the floor and pulled his belt through his pants loop. She folded it and put it in Tiffany's mouth and told her to bite down. Tiffany did. Sheba reached around her and grabbed both her ass cheeks and spread them apart as wide as she could. She pushed her back down onto Kong's cock. The pain was excruciating. Tiffany felt as if she were being split in two.

"Remember, don't look back and keep biting down," Sheba warned. Then she disappeared back down to her knees and between Tiffany's legs. She took Tiffany back into her mouth sucking and licking and lapping. She was an expert; Tiffany felt that. As good as she was though Tiffany couldn't cum because of the cock ring of twine wrapped tightly around the base of her little hard on. This kept her on edge and horny and wanting to fuck. Unfortunately, those feelings didn't overpower the excruciating pain of Kong's monster cock going deeper and deeper into her asshole and spreading her ass cheeks and hips wider and wider apart. She bit down hard on the leather in her mouth and felt the wet tears rolling down her cheeks. Her asshole burned like someone had fired up a blow torch and was using that to fuck her with. She imagined the head of Kong's cock all the way up inside her belly. It felt like it wasn't going to stop until it rode up through her throat and poked its head up out of her mouth. She felt his big hairy balls, one under each ass cheek and almost as big, and then...

Then the pain stopped.

Tiffany couldn't hide her sweet surprise so everyone knew what had happened. She had been blacked, turned out, emasculated and feminized by the master of prison sissy slut creators. Her asshole had been turned into a pussy for all intent and purposes and she accepted that. Sheba came up smiling and kissed her on the mouth. "Are you alright, baby?"

Sheba already knew the answer, but felt compelled to ask anyway. Tiffany confused, submissive and dreamy eyed, nodded. Kong grasped her hips and began sliding her up and down his fat hard meaty fuck pole until Tiffany's asshole began making wet, sloppy, squishy sounds like a used and abused hooker's snatch that had been working all night without a shower. Tiffany was no longer in pain. She had fallen in lust, love possibly, but definitely lust. The only thing keeping her from cumming was the twine wrapped around the base of her lady-cock sissy-clit. Her cock was twitching crazily, trying to cum, but failing. She had a case of "the cum shooting dry heaves". She was dizzy, euphoric and ready to faint from the pleasure of being on edge too long.

Sheba went back down and took her back in her mouth and started sucking. She released the twine, and Tiffany had an intense orgasm and flooded her mouth with cum. Sheba kept sucking until Tiffany's balls were contracting and aching from being drained dry. Then she climbed back up Tiffany's torso and sealed her lips over Tiffany's. Sheba hadn't swallowed. She flooded Tiffany's mouth with Tiffany's own spunk. Almost at the same time, Tiffany felt Kong filling her up with hot steamy spunk deep inside her bowels. His cum burned and stung because of the damage his huge HGH mutated cock had done to her insides, but it felt good too.

Kong allowed Tiffany to relax back against his hard muscular torso for a bit as she came down from her orgasmic high. She was exhausted and limp like a rag doll.

"You have some cocks to suck, baby," Kong whispered in Tiffany's ear.

"How many do I have to suck?" Tiffany asked.

"As many as you can handle, sweetheart."

"I'll suck them all if you keep your big fat cock in me, Daddy." Daddy? She couldn't believe she had heard herself call him that. It was like she had been put under a spell.

"Doesn't it hurt, baby?"

Tiffany nodded and winced. "But it feels good too."

"I think we might have ourselves a pain slut here," Sheba told Kong.

Kong kept his cock in Tiffany's tight ass pussy as he pushed her forward onto all fours. "Who's first?"

There was practically a fight as gang members raced to be the first to stuff their black meat into Tiffany's talented cock sucking mouth. Kong was so afraid they might damage her suck-hole, one he was certain was going to make him a lot of money, he felt compelled to calm them down.

"One at a time! Form a line! Hurry up or none of you will get anything!"

The gangbangers cursed and fumed but did as they were told. Tiffany sucked lots of black cocks and swallowed lots of black cum. She sucked most of the cocks more than once and some as many as three times. She had even started playing a little game with herself where she would close her eyes and try to guess who was shoving his cock in her mouth from taste alone. She had gotten to the point where nine times out of ten she could guess right.

She sucked on all fours while Kong fucked her doggy style. His dick never stayed soft for long, and more than once during her cock sucking smorgasbord, he came, went soft without slipping out due to his size, and then got hard once again. She sucked while sitting on his lap and leaning forward. She sucked where Kong spun her around on his dick so she was on her back and he held her ankles on his shoulders so she could hang her head back over the bed and stretch her throat to get face fucked like her mouth and throat were a pussy. When she was done with Kong's real male crew, she even sucked off Sheba again along with Kong's other bottom bitches.

When Kong finally pulled out of Tiffany's used and abused ass cunt with a sloppy slippery plop, she felt cold air rush up into her stretched out fuck tunnel chilling her insides. Kong's cum began to drain out of her like a waterfall of sperm, the cum cascades. She felt it running out of her ass pussy, down her stretched apart ass crack and over her cock and balls to stick to the insides of her thighs making her legs sticky almost all the way down to her ankles. When she had finished up the last suck of the last cock of the last man, she should have been exhausted, but she wasn't. Actually she was quite jacked. There was actually one more cock left to suck, and finally she got to see it and she was glad she had listened to Sheba and waited. Kong's cock was that big and scary. It looked like a third leg in size. It even had the muscles and veins. It was dripping with spent cum and Tiffany's insides. Tiffany moved to it on her hands and knees. She stuck out her little pink tongue and licked it. Kong tried to stop her, but his heart wasn't in it so he did it in a half assed way. Tiffany blew a kiss across it and her breath made it stand straight out like it was flexing or stretching itself awake following a short nap.

"I'm not sure you should do this, sweetheart."

"Why not, Daddy?"

"You've heard how it has messed up some punks permanently?"

"I'm not a punk remember. I'm a bitch. I'm going to be your top bottom bitch."

"Is that a fact?"

"It is." Tiffany glanced at Sheba. She wasn't trying to be mean or ungrateful, but it was a fact. She didn't know why, or what had gotten into her, but that's what she wanted. She had come to prison wanting to be a rough tough gangster and leave with the props to do so, but that was a fantasy. Now all she wanted was reality and that was to be Daddy's pretty little prison sissy and get as much more of his fat daddy prison cock as she could.

She started licking up and down Kong's fat filthy cock, up and down from base to head making it glisten and shine with her slippery slimy saliva. She was feeling it out more than cleaning it, but she was making it very clean as well, clean and sloppy and slippery and wet. It was dripping slimy with her drool. She did the same to his big fat hairy balls until they were dripping droplets as well. She tried to put one big ball in her mouth but it was too big, like a tennis ball. She finally stretched and stretched her jaw and pushed while Daddy pulled on the back of her head. Finally one fit in almost dislocating her jaw. She couldn't do much because there was so little room. She was lucky to be able to slightly massage it with her tongue, but Kong liked it. He groaned out his pleasure. She also found he liked when she hummed around it, probably due to the vibrations she caused. When she tried to pull her mouth off, she couldn't, everyone laughed. Kong finally showed some mercy and pulled her off by a yank of her hair.

She went for the head. It was dark, dark purple, swollen, wet and at least as big as a fist. She stretched her lips and jaw around it. It started to squeeze and compress some until she felt it pop inside her mouth. It shocked her and showed in her wide eyed expression. Kong couldn't help smiling. He was oozing generous amounts of pre-cum and she could taste it. He stepped back a couple steps now until he was dragging her little skinny sissy body with his cock. She was forced to follow while keeping him in her mouth. She ended up on all fours, her little sissy cock swinging as she tried to keep up with him. Her lips were so tightly sealed around his massive meat that no pre-cum could leak out. Her neck was stretched out in a straight line stretching her throat out in similar fashion. Kong used the pre-cum as lube to start pushing his cock down her throat.

Tiffany gagged. Her eyes bulged and then flooded with tears that ran down her cheeks. Kong began fucking her like her mouth was her ass pussy. Pre-cum flowed into her mouth. He was gentle with his hands brushing her hair out of her face and tucking it back over her ear. But in contrast, his fucking was brutal. He plowed in and out of her mouth stabbing her like he wanted to kill her. He kept face fucking her until she passed out.

When she awakened a lot of faces starred down on her, lots of black gangbangers, bottom bitches, Sheba, and of course Daddy. Most of them looked concerned. Johnny had even broken Daddy's command and was glancing over his shoulder to check out the situation. Tiffany stared a while at Johnny and wondered if he had any concern for her really. She decided he didn't. He was probably just afraid that Daddy would punish him for bringing him a faulty bottom bitch if she hadn't been able to perform properly and up to prison sissy standards.

"Are you alright, Baby?" Kong asked, brushing her hair back.

Tiffany nodded, "And I think I know what I want for my present now."

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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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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...

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