Shortening His Sentence

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The shemale on male sex you’ve become accustomed to from me takes a bit of time to build to, but if your mind is a little warped and your cock a lot hard by the end of this story, Sugar’s done right by you. 😉


Foster didn’t know what to expect as he opened the door. Foster entered the warden’s office with more than his fair share of trepidation. She didn’t usually call for an individual inmate to meet her in her office. The warden had a reputation of being a little out there.

The air in her office was markedly cooler than out in the hall. She didn’t acknowledge him at first; her eyes focused on paperwork. Her expression was blank. She was probably closer to thirty than forty. She was a pretty type, with an hourglass figure. Foster noticed her full breasts. He tried to focus on her face instead.

“You’ve been here what, about three months now?” She said, never taking her eyes off the papers on her desk.

“Yes, that sounds about right ma’am.” He told her, still standing at the door.

“Sit down Foster.” She looked up at him for the first time. Her piercing blue eyes cutting right through him. He followed her instructions and sat down at the chair across from her desk. Has your time at Creekwood been alright so far?”

“All in all. I think so.”

Foster had spent the last three months incarcerated at Creekwood minimum security prison. He embezzled from his company, little by little, and couldn’t stop himself. It started with a surprise vacation for his girlfriend and the spending ballooned from there. Melanie liked nice things. His partners found out and took him to court. The lawsuits bled him dry. He was a young successful businessman one day and the next he was practically penniless. That wasn’t the worst of it, though. Foster was brought up on criminal charges and convicted of embezzlement, along with whatever else they could trump up.

Foster took a plea deal, he made love to Melanie one last time and then started his stay at Creekwood. He wasn’t lying, though, when he answered the warden; things weren’t so bad here. It was just minimum security. Foster was allowed a lot of privileges. Plus the other inmates were just white collar criminals and drug offenders.

“You’ve got about another two years in here, don’t you?”

“Yes ma’am.” He answered.

“Call me Miss Julia. I read through some of your file. You used a company credit card to purchase Tiffany jewelry, clothing at Chanel. Your girlfriend or your wife must have expensive taste.”

“My girlfriend, yes. That’s behind me though… Miss Julia.”

“The crime or the girlfriend?” She asked him skeptically.

“The crime. I know it was wrong.”

“Is the girlfriend still in the picture?” Miss Julia shifted in her chair.

“She is. We live together. Well, we did,” he told her with a hint of sadness in his voice.

She got up from her chair and put a book from her desk back on the bookshelf. Her skirt ended just below mid-thigh and hugged her curves. “Two years is a long time for a woman to wait.” She took her seat again and eyed Foster. “Are you sure she will? An expensive taste like hers has to be quenched. Then you’ve got to figure that a woman has needs. What if she finds a man who can give her the things you can’t?”

Foster shifted uneasily in his chair. This was a nightmare of his. Miss Julia had hit the nail on the head. Melanie was materialistic, and a bit of a nymph on top of that. He couldn’t bare to think of her with another man. “I don’t know Miss Julia. I’m just trying to do my time.”

“What if I told you your sentence could be shortened to just a year? Or six months, maybe even less. The bed you share with your girlfriend might still be the way you left it – not dirtied by another man.”

Foster started to get the feeling he was walking into a trap. Regardless, he was too afraid of her to answer the question in any other way. “That would wonderful if that were possible.”

Miss Julia rapped her fingernails on her desk and looked at him closely, “It is. I have the ability to make it happen. You could be out in just a few months with good behavior.”

He tried not to get excited. There was always a catch. “What, what would I have to do?”

She leaned back in her chair, almost seeming to consider whether to continue. “Have you ever heard of a prisoner by the name of Desiree?”

The hair on the back of Foster’s neck stood up. Everyone knew who Desiree was. It’s worth mentioning that Creekwood minimum security prison occupied the same land as another prison. This one was maximum security; the two were separated by a fence. People called them Creekwood min and Creekwood max. Miss Julia was the warden of both prisons. But this wasn’t just any maximum security prison; it was for shemales. The ones which other facilities couldn’t handle. Every time he was out in the yard, he’d get whistles and cat calls from the other side of the fence. Foster trained himself to ignore it.

Desiree was one of the top shemales. Rumor had it that because of her immense size, she’d originally been placed in Ümraniye Öğrenci Escort a men’s facility. He heard that she victimized the inmates there until finally being transferred here. Foster knew enough to know that he didn’t want her name to roll off Miss Julia’s tongue.

“I’ve heard of her.” He answered nervously.

“She’s being released soon.” Miss Julia let her words hang in the air for a moment before continuing, “Have you heard the rumors about her Foster?” He nodded his head yes. “They’re mostly all true.” She watched his face start to lose its color. “The state says she’s served her time. There’s nothing I can do about it.”

“That’s terrible.” Foster offered, not sure how this concerned him.

“I believe Desiree is woefully ill-equipped to abide by the rules on the outside. Her idea of a first date is dragging a man into a dark alley and having her way with him.” Foster got the chills, and this time it wasn’t from Miss Julia. “If we don’t do something before she’s released, Desiree will be free and she’ll be on the prowl, and she’s not going to take ‘no’ for an answer.”

Foster thought hard about whether “we” included him. It couldn’t, could it? How was Foster supposed to help. He felt relieved just knowing he was locked away in prison and not in danger of being dragged into that dark alley by Desiree.

“I believe her only chance for rehabilitation lies in teaching her what a healthy relationship is. I need you for that.”

“What?” Foster cried. How could this possibly involve him?

“Relax. She’s not going to hurt you. If she just interacts with a man in a positive way, goes on a couple dates with you, we might instill this responsible behavior in her going forward. It’s a roll of the dice I’m willing to take.”

“I can’t do that!” Foster said emphatically. He wasn’t going to be some guinea pig and stick his ass on the line in the most literal sense. The guards from the hall heard the commotion and barreled into her office but Miss Julia shooed them away with a snap of her wrist.

“You’d rather be stuck here while some asshole shoves his prick up your girlfriend’s snatch?” She asked him in a stern manner.

“I, I didn’t say that. I just can’t be part of this.” Foster calmed down, remembering that Miss Julia could make his life a living hell.

“Every dream you have will be of your little girlfriend screaming another man’s name. She’ll scream it at the top of lungs while she cums – while you’re rotting here.”

“Please stop.” Foster couldn’t help but imagine it in his head.

“With one word I can have those guard back in here. I can have your clothes removed and your ass thrown in with you know who. I can fuck you for life.”


“Or you can do what I tell you to and go on a couple supervised dates with Desiree. Maybe give up a couple kisses, and then you can go home to your girlfriend and your old life.”

“That would be better than–”

Miss Julia cut in before he could finish his sentence, “Good. Someone will come for you tomorrow. Now get out of here.”

Foster got up, feeling more scared and confused than he had when he first walked in, and started to leave. He turned back for a moment and asked, “Why me?”

Miss Julia returned to the work on her desk, but looked up at him, her lips opening into a frightening smile, “She chose you.”

Foster was escorted back to his wing. He spotted a few of the guys playing cards by the window. His best friend Kevin called out to him, “Hey Foster! Sit down, we’ll deal you in next hand.” Foster sat down, but didn’t converse with any of the guys. He looked out the window quietly, his eyes locked in on Creekwood max across the way. Desiree was in there somewhere. Lurking; waiting.

“What did the warden want?” Kevin dealt out the cards.

“Miss Julia,” Foster corrected him, still with a faraway look in his eyes.

“Miss Julia.” Kevin mimicked Foster’s voice and everyone at the table laughed.

“I don’t want to talk about it.” Foster looked at his hand and then slipped the cards back down on the table and headed back to his room.

Miss Julia had a way of laying out things in a way that left little room to say no. Foster knew that now. He was attached to this plot of hers. Rehabilitate Desiree? From what he’d heard, such a thing wasn’t possible. Desiree was a predator.

“What did she want? You’re acting like a dick so she must have said something.” Kevin appeared at the door.

“What do you know about Desiree?” Foster asked instead of answering.

Kevin had been at Creekwood min for a few years now. He was pretty connected, which meant he heard a lot of stories. He filled Foster in on everything he knew, trying to figure out why Foster would ask such a question as he did. Desiree was a big hard blonde. Kevin didn’t know her original crime, but his educated guess was that it had to be sexual-related. Her reputation now was as a sexual fiend who lived for sex. She climbed the fence a couple years ago and cornered one of the male inmates before the guards Ümraniye Çıtır Escort could stop her. The stories went on and on.

Every inmate was locked in their room for the night. Sleep wasn’t easy to come by for Foster. He tossed and turned most of the night; falling in and out of dreams about his girlfriend with other men and himself with Desiree. In his dream, they were together in a cell together and Desiree pulled her cock from her jumpsuit and told him to bend over. Foster was still exhausted in the morning. He ate with his friends and then watched television well into the afternoon. They were just complaining about the channels available when Foster noticed a man he’d never seen before out of the corner of his eye. The man walked right up to him and said, “I’m Ed. You’re Foster, right?” Foster replied that he was and Ed asked Foster to follow him.

Creekwood min was silent as Foster followed Ed through the halls until they ended up at the back entrance. The guards there opened the door for Ed. They walked through the field, Foster realized they were heading toward that ominous fence and the even more ominous Creekwood max. “Where are you taking me?” He asked.

“I know you talked to Miss Julia yesterday. She filled you in on the need-to-know. I don’t have time for the details right now. Just follow me. Desiree is waiting.”

The steps Foster was taking started to get heavier. They were doing this right now? This was news to Foster. He wasn’t mentally prepared in the slightest. “Wait. I think I deserve the details if I’m going to be spending time with this woman.” Ed shot him an impatient look and grabbed Foster’s arm; their pace quickening by consequence. Foster had a bad feeling as a guard unlocked the gate and let them through. They walked through the yard and then into Creekwood max. Foster had never been here before. Creekwood min looked like a hotel in comparison; this place, it was a real prison.

The facilities were massive. Foster’s feet started hurting from all the walking. “Where are we going? It’s taking forever to get there.”

“There’s a shortcut, but it would have taken us right through general population. Would you like to try that route instead?” Ed asked sarcastically.

Foster shook his head no and shut up, reasoning that they’d get there when they get there. They finally stopped outside a door. Ed pulled out a card and flashed it to the camera on the wall. Foster heard a click and Ed pulled the door open. He stepped inside and started going through a locker. “She’s next door waiting.” He told Foster with little interest in his voice.

“What do you guys want me to do! I don’t understand this.” Foster whined. Just knowing that she was in such close proximity made his stomach knot.

“Miss Julia wants you to put these on.” Ed tossed him street clothes. Foster picked through them. A dress shirt and a pair of black khaki pants. Foster couldn’t wrap his head around this.

“Are we going somewhere? I mean leaving Creekwood?” He asked, removing his jumpsuit and sliding the khakis up his legs.

“No. But this isn’t something we just slapped together yesterday. Miss Julia has personally inspected everything and made sure that it’s to her liking. Are you ready?”

“Ready for what! Who the hell are–” Ed lurched forward and covered Foster’s mouth.

“Did Miss Julia inform you what she’s going to do to you if you fuck this up? Keep your voice down. These women are like animals. Rile them up and you’re screwed before we even start.”

If Foster wasn’t afraid before, he certainly was now. He watched the man do something curious: he stripped. He shoved his prison official uniform in the locker and pulled out a suit. “This is your first date with Desiree. You’re meeting her at a french restaurant. Tell her that her eyes are beautiful and she’s wearing a lovely dress.” Ed slipped the suit jacket on over a dress shirt and pulled a speechless Foster out of the room with him. They walked through the next door, Ed whispered, “And remember, I’m the only thing standing between you… and her.”

Foster was amazed at the detail of the room. It looked like a place he might take Melanie. There were ten or fifteen dinner tables set out. He saw the woman he knew was Desiree from Kevin’s description in the middle of the room, sitting at a table. Foster’s feet felt like they were trapped in quicksand; he couldn’t move. Kevin’s description was spot-on. A big hard blond. She was wearing a dress with a low neckline which showed off a valley of big boob flesh. Her long blond hair hung off her shoulders and when she looked at Foster, her full lips opened into a grin.

Ed realized Foster wasn’t moving and gave him a push; he then walked a few tables down and took a seat. Ed watched Foster walk slowly over to Desiree’s table. Ed was satisfied that the wheels had been set in motion and pulled the sports section out of a pocket in his jacket.

“I was beginning to think you stood me up,” she chuckled in a lighthearted manner which Foster didn’t totally trust.

“No, no, Ümraniye Elit Escort of course not. You have lovely eyes and your dress is beautiful,” his voice echoed throughout the large dining hall. Foster then remembered that Ed had said beautiful eyes and lovely dress, he almost corrected himself, but then decided they were interchangeable anyway.

“Sit down. I’m starving,” she said in a voice which told him the starving part wasn’t in reference to dinner.

Foster gulped and pulled his chair out. He sat down. Desiree just kept looking at him, not saying anything, just staring at him. It made Foster feel even less settled. He noticed a menu on the table, they really thought of everything. It looked professionally made. Neither of them said anything. Foster was starting to sweat. A guy dressed in a waiter’s uniform walked over to their table and asked about their order in a french accent which sounded authentic enough. Foster was just relieved to have the silence broken.

“I’ll have the streak frites.” He told the waiter, and Desiree ordered something Foster didn’t recognize. The waiter left with their orders.

Desiree looked around the room and spoke, “Not very crowded tonight, huh?”

“No. I guess not.” Foster shook his head.

Desiree adjusted her strapless dress, which jiggled her tits and attracted Foster’s eyes. She started to play with her hair and took a drink of ice water. “Not much conversation here either.” She lamented.

“I’m, I’m sorry. I’m just nervous.”

“That’s sweet.” Her hand fell on top of Foster’s and he jumped at the touch. He instantly felt frozen and unable to talk. Ed was watching them carefully now. “I didn’t say I wasn’t having a good time though. Looking at you is a good time.”

“Ummm, thank you.” Foster started to pull his hand away but Desiree wouldn’t let him. She held it in place and started to rub it as she stared into his eyes.

“I was so excited when I asked you out and you said yes. I’ve been thinking about it ever since. This dress is new. Could you tell?”

“Well, it did look new, but I wasn’t sure. It’s very nice,” he told her awkwardly.

She leaned across the table, causing her neckline to slip lower, and started to whisper huskily, “It is. If I’m letting you in on a little secret though, it’s a little tight around the cleavage.” She leaned so close that Foster could feel her warm breath and see she wasn’t wearing a bra. The smell of her perfume washed over him. “I was fiddling with it earlier and one of my tits just about flopped out. That would have been a memorable first date experience, wouldn’t it?” Desiree said seductively.

They heard a loud flap of Ed’s newspaper. Desiree sat back in her chair and gave him the finger. Foster’s face was red. Much to his chagrin, all the visuals and talk of tits had left him with a bulge in his pants which he was determined to hide from Desiree at all costs. The waiter came back with a cart that had their food on it. Foster saw that Desiree’s mystery dish was in fact some sort of stew.

Foster poked around at his fries until they turned to mush. He wasn’t very hungry. “Would you like to try mine?” She asked.

“No thanks.” But Desiree didn’t take no for answer. She offered him her spoon. It tasted pretty good. Foster kept catching himself sneaking peeks at her cleavage. It was concerning. This whole absurd dinner date was concerning. They were at Creekwood max, not a french restaurant. They shared a little small talk, here or there, still pretending this meal was the real deal. Once they finished the main course, Desiree and Foster ordered dessert.

“We should probably discuss who pays the bill before it comes. I’m not opposed to going halfsies, but I did ask you out, so that’s sort of cheap of me.” She smiled so sweetly that Foster nearly forgot that this was the same Desiree he’d been hearing horror stories about for three months.

Their desserts were served soon afterward. Desiree took one bite of hers and rumbled, “My burnt cream is cold!” Foster didn’t say a word. He looked at her worriedly. “It’s cold!” She said again, louder this time.

Ed dropped the sports page on the table and marched over to their table. “Mine is too. I’ll take it back to the chef. I’ll be back in thirty seconds,” he told them. Desiree’s manner at the table put Foster and Ed a little more at ease than they should have been given the circumstances. Foster didn’t think much of it when Ed hurried back to the kitchen.

Once the doors closed, Desiree leaped forward and grabbed the back of Foster’s head. She pulled him across the table until her lips were nearly touching his ear. He opened his mouth to scream, but she hissed, “Don’t you dare make a noise,” before he could. ” That dumb fucker is going to realize my dessert was supposed to be cold in about ten seconds and run back in here. Once we’re done with dessert you’re gonna tell our chaperone that you want to go back to my cell with me to continue our date.”

They heard the doors open again and Desiree released her hold on him. She smiled at Foster like nothing had happened. Ed gave her a cross look and dropped the dish back down on her table. He returned to his table and resumed reading. Foster’s world had collapsed again. She was quite convincing and he’d fallen for it. It was all an act, though. Desiree was intent on getting him back to her cell with her.

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