Prison Wager free porn video

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"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. She's a fine woman."

"Don't say that about her!" Tom yelled at the guard.

He stared at Tom. "What are you going to do? Tell the warden because that doesn't scare me. I do love when your wife arrives and sits in the visiting room. You can't see from your view behind the glass but she has a beautiful set of legs."

"Please stop talking about her." Tom pleaded with the guard.

"I have a deal for you, convict. Do you want to hear about it?"

Tom asked. "What kind of deal?"

The guard smiled. "It isn't a deal; it's more like a wager."

"What kind of wager?"

The guard smiled again. "If you win, the guards will give you a break throughout your time here in prison. I mean you will not break your balls or we won't."

"If I lose?" Tom asked.

"If you do then it will be the worse six months of your time here. What do you say? Are you in or out?"

"Let's hear the bet." Tom replied. He loved gambling. That is what caused his little stay in the prison. He fudged his books at work to pay for his gambling habit. He was found guilty for embezzlement. He has been in for twelve months. He was sentenced for eighteen months.

"Ok. Here's the bet. That little wife is seduced by me. If she is, I win. If she doesn't then you win. What do you say?"

Tom was shocked over that statement. He knew he could win the bet. His wife loved him. He asked the guard. "You need proof that you did it."

"Ok. I will have a videotape of the sex for your viewing." The guard told him. "Plus I will only need two weeks to do it. You can't warn her and I will keep my word that I will not tell her anything about you or that I'm a guard at the prison."

Tom realizes that he had a sure win. He knew Mary would never cheat on her. He was going to have an easy six months left. He nodded his head. "I want to do it."

They shook hands to make the deal official. He told Tom. "I hope you know but you are going to lose and I am going to have your wife every way possible."

"You wish."

Mary arrived for her weekly visit with her husband. She missed him very much. She is forty and should be having sex with Tom but he had a gambling problem. He would be at the track instead of their bed.

Mary walked toward the entrance to the prison. She didn't like the place. She was always hit on by someone, from the guards or prisoners. She knew she would because the way she always dressed. She was wearing a black skirt that stopped at her knees, black blouse with see through sleeves, black pantyhose on her legs, and black high heels on her feet.

Mary had to admit that dressing like that did make her feel younger and sexier. She loved teasing the guys but the prison was something else. The guys here were here for rape and murder and other things. She was scared when it came to that.

Mary walked into the visiting area. She met the first guard, who was Mr. Roberts. He informed her that they have to search her. She nodded her head. She watched as the guard stepped closer to her. She held her breathe as the big guard approached her.

"Sorry for this." Mr. Roberts informed her. "It is just we have to do it once in a while."

Mary held her arms up, so the guard could run the wand over her to see if she had anything metallic under her dress. She couldn't believe the guard couldn't see the sheer outfit couldn't hide anything.

"Nothing with that. Now, I have to pat you down to make sure you aren't carrying anything." He set down the wand and ran his hands slowly over her sides to her hips and proceeded up her front. "I'm sorry but it is policy."

Mary nodded her head as the guard touched her breasts on the way up. He finished and told her that she was clean. Mary started to blush after the feel of her breasts.

Mary walked away and headed for the cubical where her husband was sitting behind the glass. Tom was smiling from behind the glass. He picked up the telephone and spoke. "Hello Darling. How are you doing?"

"Fine." Mary replied but remembered the feel of the guard against her body. She couldn't say anything to her husband. He couldn't do anything, being behind the bars.

They talked about the usual stuff about the children and how they both are. Mary sensed that he was holding something back. She wanted to ask but the feel of the guard was still on her mind. She needed to go home and play with herself.

"Are you sure you ok?" Tom asked his wife. "You seem disturbed."

Mary shook her head. "Nothing is wrong, honey."

"If you are sure. You can tell me anything you know." Tom was trying to find out if Mr. Roberts had tried something with her.

"I know. It isn't anything special." Mary replied.

The rest of the talk was about the future, when he gets released. Mary smiled as her husband told her the plans. She was prefect wife, but she still wanted to have her brains fucked badly. She hadn't had Tom make love to her in over twelve months. Her pussy needed some treats other than her own finger. She had to get out and get some.

Mary returned home a couple hours ago and went straight to the bedroom drawer. She pulled out her toy and began to masturbate with it. Mary played with herself until an hour ago. She needed a real one. She needed a cock badly inside of her.

She made a call to a friend and asked her out. Melissa agreed to go. They decided to go to the pub in town. Melissa was a known for partying lately. She walked to the closet. She needed the right outfit to find someone to fuck her. She didn't want cheat but the urge was too great.

Mary found the right one. She had a one piece white dress. She wasn't going to wear a bra with the tight dress. She had a thong on. Her legs would be in nude color stockings, and red high heels.

Melissa arrived at the house wearing a red dress with black shoes. She smiled to her friend. "Ready to have fun."

"Oh yes."

A short time later, Mary walked to the door of the pub with Melissa and noticed a black van pulling into the driveway. She thought that the van was following her. It couldn't be following her. She didn't get stalkers. She thought not.

Eric Roberts pulled his black extended van into the parking lot. He waited to see where the little wife would go after the feel up. He felt the nice size breasts what she thought was normal checking. He waited for a couple of hours for her.

Eric wanted her inside of his portable studio. His van had plush carpeting, mini camera with special photo film for night. He was going to seduce her here. He opened the door and walked to the front door of the pub.

Mary liked the pub as the music was being played. Her hand holding the white wine as she listened to Melissa's adventures with her boyfriend. She finished the drink and told her that she would be back in a few.

Mary returned to the bar. She waited for the bartender. Her eye caught the same prison guard down the bar. He caught her eye and walked towards her. Her heart started to beat quickly as he walked towards her. She couldn't help herself.

Mary smiled as he ordered a beer and asked what she was having. Mary told him she is having a white wine. The bartender gave them the drinks. He turned to her. "My name is Eric."

"Thank you, Eric."

"You are welcome." Eric indicted a clear table near the bar.

"I'm sorry but I am with a friend."

"I don't think so. Look." He pointed to Melissa kissing a blonde guy really deep. "Please sit with me."

Mary shrugged her shoulders and sat with the prison guard. The guy, who felt her up in the prison visiting area. Her body was still throbbing because of the guy across from her. She found the guy to have fun with.

They talked to each other and he hadn't touched her. She found out that he has been a guard for ten years and he was five years older than she was. He lives in the plush East Side. She felt slight jealous because she used to live in that area, now in the dumps. He smiled and leaned closer to. "I want to tell you, Mary. I did it on purpose."

"Did what?" Playing coy with the big guard. She wasn't going to tell him that she remembered everything.

"Don't play stupid. I know what you are doing. Well, I liked touching those huge breasts. I wouldn't mind sucking them. Do you?"

Mary was shocked to hear it. She became very blushful. "Please don't."

Eric smiled at her comment. He knew he was getting to her. He spoke to her again. "I bet you have big nipples also. I can see them though that dress."

"Stop please."

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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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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...

2 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,...

2 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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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...

2 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...

3 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....

2 years ago
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PrisonChapter 8

The HM Mount Prison was about a forty-five-minute drive from Cheshunt. Five other guys and I were taken there by a prison bus. On arriving, the driver stopped in front of two big gates. The guard sitting next to him grabbed his radio to speak to someone. Then a few seconds later the gates started to open. On exiting the bus, we were all put in line then taken to a room where an older guard explained to us the prison rules in a secure, orderly way. The guards took us to another room where...

2 years ago
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Prison Girl1

I went to one of our states many Correctional Facilities to visit my son in that state prison. I visit him about once a month on the first Saturday of the month. This time however when my son arrived in the visiting room he said hi to the inmate at the table next to me first then gave the girl sitting with him a light kiss on the cheek and said hello to the lady with them. After all of that he finally gave me a big hug and sat down. He then introduced me to the other inmate Juan, his...

2 years ago
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Prison Aint So Bad

"I can't fucking believe it, not too long ago, to this day, I was living a good life, I was drinking champagne with my girlfriend Alexis, not the brightest of girls but damn she had a nice body, that night we drank until we couldn't and fucked until the sun came up, now look at me, travelling on this bus heading to prison, all because I was stupid enough to commit fraud".The bus pulled up at the prison and instantly the convicts gathered by the fence, I could hear them all screaming and...

3 years ago
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Prison Break

This story is written by an adult for an adult audience. If you're not an adult or are offended by graphic sex or themes of gender transformation either you or this story are in the wrong place. Read no further. If this is your cup of tea, I'd welcome any comments or criticism as this is my first contribution. Do not redistribute this story. Prison Break By Amber S We were forty-five minutes from gone, when the cops moved in and grabbed Steve. I watched for a second while they...

2 years ago
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Prison Guinea Pig

Prison  Guinea Pig-part 1Having been arrested for drug possession in a small European country while traveling,  I was sentenced to five years hard time. I had been carrying a stash of cocaine,  and the amount, I found, was over a certain limit making it a much more serious crime.My life collapsed around me as I was hauled off to serve my term in one of the toughest prisons in the country. I was simply numb after being processed and shoved in a cold cell, and the looks of depravity from my...

4 years ago
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Prison Strapping

The most sexually exciting and, I have to say, the mostshameful experience I have ever witnessed was the bare bottomwhipping of a young English woman at the women's reformatory inGeorgetown, Queensland in 1948. I was just twenty five then andemployed as a security guard along with seven other guys. Therewere only 120 women prisoners in the reformatory and most of theroutine minding was done by the twenty or so female warders. Theeight men were employed primarily in case of fights...

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