Shortening His Sentence

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SugarandSalt
SugarandSalt
4,414 Followers

"Why the long face sweetheart?" She asked, knowing perfectly well what was wrong.

They finished their desserts and Ed walked over to them once again. "It looks like this place is about to close. We better all go. I'll escort you two lovebirds out," he chuckled.

"We had such a good time that we're gonna continue the date back at my place. Right honey?" She looked over at Foster expectantly.

Foster's mind reeled as he tried to think his way out of it. "I'd like to, but I think we're moving a bit too fast baby. I mean, I don't want to do anything to jeopardize our relationship. I don't want to mess this up." He thought the excuse sounded convincing, but Desiree was shooting daggers at him.

"It sounds like you've got a good man here," Ed patted him on the back. "Taking it slow is a good idea." They walked out of the room together and it instantly became a dark, dull prison again. The guards situated there walked with them. They came to the door of a wing. Foster could hear collective screaming and unruly noise from inside.

"This is my stop," she smiled at Foster. "Aren't you going to kiss me goodnight?" Foster hesitated, but Ed gave him another push and he slowly walked toward her. He expected to give her a peck on the lips and then say goodnight, but as soon as he got within a foot of her, she grabbed him. Her lips crushed against his. Her hands flew down his back and roughly grabbed his butt. Foster jumped when she did, and Desiree's tongue darted into his mouth. When his tongue moved, she caught it with her teeth. He was sure she'd bite it, but she sucked on it.

"It's getting late. You two have the rest of your lives to express your love," Ed chuckled. He grabbed Foster's arm and pulled him from her clutches. Foster was stunned. He blinked a few times while being dragged away by Ed. The guards opened the door for Desiree. The mayhem from inside got louder when they did.

Foster tried to get a handle on things as they left Creekwood max and headed back to Creekwood min. It was difficult to do, especially since that kiss had left him with an aching hard-on.

"Miss Julia specified that she wants to see you directly afterward," Ed told him as they made it back to Creekwood min. Ed escorted him to her office. Foster entered Miss Julia's office and Ed slammed the door shut behind him.

"Did you have a good time?" Her office was dark, but Foster could make out Miss Julia's figure at her desk.

"I, I guess so. I'm not sure. This is all so crazy."

"How was your steak? I hope Henri didn't cook it too long. Take a seat by the way."

Foster apprehensively sat down. "How do you know what I ordered? You had a spy?"

"I'm the warden here. I don't need a spy. I have eyes everywhere; not all of them are human." Miss Julia turned her computer monitor toward him and clicked something on the screen which caused a video to play. It was footage of the dining hall. He could see himself eating across the table from Desiree. "She's a good actress, isn't she?"

"She told me she wanted me to go back to her cell with her," Foster confessed.

"Of course she did. And if it had been just you and her, she would have dumped the table and threw you on top of it."

"You're gonna make me go out with her again, aren't you?"

"Would you like to see another video? Ed took this one. He's been staking out the apartment you share with your girlfriend." Miss Julia clicked around on the computer and another video came up.

The possibilities of what could be on that video set Foster's brain on fire. "Are you trying to torture me Miss Julia? I did what you wanted. I played into your game."

"You had one date! One kiss. My video's a little grainy, so tell me if I'm wrong, but I think the camera caught a bulge in your pants after the kiss. You liked it." She told him confidently.

"I've been locked up here with dudes for three months. I know she's got a dick, but anything with tits makes me hard. What do you want from me?"

"And what a pair of tits they are. Desiree is one of our most well-endowed inmates. That goes for her cock too, but you'll find that out for yourself soon enough."

Foster was clinging to his last shreds of dignity. He started feeling like Miss Julia was pimping him out to Desiree. "You told me it would only take a couple kisses and I could go home..."

Miss Julia clicked her mouse and the light went on, she stood up and walked around her desk. She sat down on top of it. Her skirt rode up her legs and distracted Foster. "Desiree is getting out of here and she's gonna have a lot of sex. She needs to learn how to do so without hurting her partner. Her rehabilitation will never take if we don't teach her how to fuck in a way that's pleasurable for both participants." Miss Julia brushed her thumb along Foster's lips, "She'll need to see an example first," she leaned down and kissed him. Her soft lips and supple tongue got to him, his brain stopped, and he kissed her back.

When their lips parted, he asked, "You want me to have sex with you?"

Miss Julia laughed in response. "No, that's my job. Or you didn't realize I was packing..." Foster's eyes fell below her waist and he noticed the unmistakeable bulge of a cock. She was a shemale too! In retrospect, he probably should have realized that. "Seeing you and Desiree together got me pretty turned on. Since the three of us won't start our lessons until tomorrow, would you mind helping me take the edge off?"

"That's--"

"Great!" Miss Julia lifted her skirt up. She wasn't wearing any panties. Her hard cock sprung out and waved around in the air. It was at least seven inches and thick! Miss Julia grabbed Foster's head and pulled it between her legs. He opened his mouth, to speak rather than suck, but Miss Julia wasn't keen on details like that. She took the opportunity to shove her womanhood into the warmth of his mouth. "I've been so fucking horny. I can barely get any work done. This is going to help a whole lot," she thrust deep into his mouth, making it a struggle for Foster to stop from gagging. "I'm cooped up here all day." Foster had never sucked a cock before. The act was so sloppy, and that just made Miss Julia hornier.

Her penis twitched in his mouth. Foster quickly learned that the more he used his tongue, the more her cock twitched and the hornier she got. Miss Julia held his head firmly in her grasp, her icy blue eyes took in everything. Foster gave up having any control over the situation; this was Miss Julia's prison; Miss Julia's office; and Miss Julia's cock he was sucking. The wet smacking sound of his lips and tongue along with the occasional moan from Miss Julia filled the room.

"You look so cute between my legs with my dick in your mouth. How does a guy not look sexy doing this. Really suck it now," she told him, easing up on her grip. Foster responded by bobbing his head up and down on the big pole. The swollen head drove deep into his mouth. "I'm gonna cum. This should tide me over 'til tomorrow," she moaned.

Foster sensed a difference in her demeanor and realized she was mere seconds from exploding in his mouth. Miss Julia's plunged as deep as she could into the depths of his mouth and her cock lurched. Cum sputtered from her tip and shot down Foster's throat. He swallowed the hot goo as fast as he could. By the time he'd gulped down one mouthful, Miss Julia produced another. Her hands held him in place long after she'd finished cumming, enjoying the sensations of his soft lips around her shaft and her cock head lodged in his tight throat.

"Good work Foster. Mmm... that felt nice," her shrinking penis popped out of his mouth. Foster sat back in his chair, the reality setting in. Miss Julia smiled when she saw the bulge in his pants. "I think you're gonna make it out of Creekwood min quicker than you think. Now get back to your room and jerk off. I don't want you too tense tomorrow."

"Yes Miss Julia." He pushed up from the chair and left her office. A guard escorted him to his room and handed him a clean prison uniform. The first thing he saw on his desk was a picture of himself and Melanie. The video Miss Julia had mentioned came to mind; he turned the picture away. Foster fell back on his bed and pulled his cock out. He compared it to Miss Julia's in his head.

Kevin found him the next morning at breakfast. "Where'd that guy take you yesterday?" He asked.

"Miss Julia called me back to her office is all."

"She really has her claws into you. I heard a rumor that you were spotted on the way to Creekwood max. Is that true?"

"Forget about it Kevin. I can't talk about it," Foster answered. He didn't even really know himself. The last two days had been a whirlwind. After sucking Miss Julia's cock and jerking off, he fell asleep and dreamed about being taken by both Miss Julia and Desiree. Crazy things were happening to Foster, things he didn't know how to resist; even more scarily, he didn't know whether he wanted to.

Ed popped up after breakfast. He took Foster to a shower room. Foster showered and shaved. Ed handed him a pair of boxers. "Where's the shirt? The pants?" Foster looked behind Ed's back as if he were hiding them.

"Miss Julia says you won't need them." He grinned, leading Foster down a long corridor once he'd dressed.

"Is she... I mean are they waiting for me?"

"I just take the orders. Miss Julia didn't tell me anything else. Just get you from point A to point B." They stopped outside a room on the other side of the prison. Foster had only been down here once. There was a concentration of guards in the hallway. Ed saw Foster looking at them and said, "They're for Desiree. That's serious business. We'd have a bunch of scared shitless friends of yours if they knew Miss Julia was bringing a shemale on the premises."

Foster went into the room alone. The lights were out. He suddenly felt extremely afraid, his hand searching for a light switch in the dark. He heard a noise and froze. "Is somewhere there?" He called out. There was no answer. Foster stumbled through the dark room.

"Do you think we should help our poor friend?" It was Miss Julia's voice.

"Lemme out of these things and I'll help him real good." Desiree's voice stopped Foster dead in his tracks.

"That's sweet of you. But I doubt anyone has ever accused you of being too nice Desiree. Foster, I want you to keep walking forward. You'll find us eventually." He listened to Miss Julia and kept walking. He walked right into something. Foster fell forward and landed on a bed. Miss Julia laughed. "Our visitor has arrived." He felt a hand on his back and not knowing whether it was Miss Julia or Desiree, jumped back. Foster landed at the foot of the bed.

"Boo!" Desiree's voice seemed right next to him. He jumped again and a pair of hands caught him.

Foster tried to wiggle out of the person's grip, "Easy. It's me." Miss Julia held him tighter.

"Whatever game the two of you are playing - just stop it!" He shrieked.

"Lights on!" Miss Julia yelled. The lights turned on. It took a moment for Foster to see properly. They were in a room with a bed. A king-size bed. Desiree was tied to the foot of the bed. She was naked! He looked back at Miss Julia, she was naked too! "I know what you're thinking, you're over-clothed. We'll fix that soon," Miss Julia chuckled. Foster looked back and forth between them. Between Desiree's massive breasts and Miss Julia's full pert ones. Miss Julia's cock was hard. He couldn't see Desiree's cock.

"Bitch give him to me and I'll have him naked and hogtied in thirty seconds," Desiree snarled.

"Watch your language bitch. You said something we can build off of. Men don't want to be forcibly stripped and 'hogtied.' Men have to get pleasure from this as well or they won't want to do it. Do you understand?"

"I don't care what men want!" Desiree spat.

"That's how you ended up at Creekwood max. In a pen with a bunch of shemales and no men. And ultimately tied to the foot of my bed. I doubt either of you thought this bed was standard prison issue. I couldn't remove you two from Creekwood, so I brought the most important part of my bedroom here: my luxurious bed. Never fuck without it," she smiled.

"I don't care how I ended up here and I don't care about your bed. Free my hands so I can fuck this little bottom!"

"I just want to prove to you Desiree that you can have sex with men, tons of them. I mean you can drain those big balls of yours morning, noon, and night, and not get in trouble for it later. That's how I do it because I know how to treat men." Foster started to get very wary of this entire conversation. How could these two big-dicked chicks drag him into this. "Take Foster for instance. Until yesterday he'd never sucked cock. Never had a fantasy which wasn't pussy, pussy, pussy. Today he's halfway toward becoming my dick-taking bitch."

Foster opened his mouth to protest, but Miss Julia put her finger to his lips, she winked at him and mouthed the words, "play along," before saying louder, "The big girls are talking now." She glanced down at his lap and said, "Look at him Desiree. He's scared, but look at his cock." Miss Julia snaked her arm around him and grabbed his dick. "He's hard as a rock. With a little guidance, a little push in the right direction, he can be a bottom bitch for the rest of his life. Instead of a witness at your next trial." Foster was embarrassed that they'd caught him with a hard-on. He had two pairs of beautiful tits staring him in the face for crying out loud. Miss Julia's gesture had helped him calm down a little. This was a show for Desiree.

Miss Julia let go of his cock and started to rub her finger in a circular motion around his nipple. He thought of what Miss Julia had said and tried to play along. "That feels good Miss Julia," he moaned.

"Desiree wants to hurt you. I want to make you feel good. Feel things you've never felt before. Doesn't that sound better than what big bad Desiree was planning?" Miss Julia said in a seductive voice that sent a jolt down Foster's spine.

"Yes, yes it does." He whimpered and meant it.

Miss Julia made a show of licking up his neck next. She grazed his earlobe with her teeth and whispered to him, "Mmm... you're so sexy. You're doing a good job. Let's see how hot and flustered we can make Desiree." Foster glanced over at Desiree and saw how frustrated she looked, yet she couldn't look away. Foster turned his head toward Miss Julia and they started to kiss. Their lips smacked together and their tongues mingled.

"Release me!" Desiree shouted at Miss Julia, her frustration building and building. "I'm gonna fuck his little ass so hard he'll be dripping cum for days!"

Miss Julia pulled her lips from Foster's and smiled at Desiree. "Let's take a look at it." She pushed him down on the bed and pulled his boxers off. Foster felt the cool air on his ass and went along with what Miss Julia said. He felt her hands on his cheeks. She spread them. Foster could feel two pairs of eyes on his backside. "Look at that cute little hole. You see Desiree? I didn't have to force him to show us his treasure. He let us see it because he wanted to. He's going to let me fuck him because he wants to be fucked."

"His virgin hole is mine! Don't you dare." Desiree growled. "You promised me if I cooperated with your dumb ass date idea I could have him!"

Miss Julia had laid it out in stark terms. Until now, it was mostly innuendo. But she made it clear she was going to fuck him. He had conflicted feelings about it. Miss Julia was making him feel very good, but he was straight, how could he let her fuck him! The reality set in that Foster didn't have much say in the matter.

"I promised you'd get some booty off him. I didn't promise you'd be the first. I'm going to teach you how to butt fuck a bottom like Foster while hurting him as little as possible and bringing both of you the most pleasure."

"You fucking bitch!" Desiree thrashed against the bed but couldn't free herself.

"I told you to watch your mouth once! If you ever want a taste of this sweet asshole, you better fucking behave yourself Desiree," she cautioned her.

Miss Julia stared at his virgin opening and struggled to contain herself. She felt a rush of excitement, witnessing the fruition of her master plan. She could kill two birds with one stone. Fuck this little hole and maybe teach Desiree a little something while doing it. Miss Julia had to control herself, though, because her penis was battling her brain over what to do next. Her cock wanted to plunge into his tight bottom with every ounce of force she could muster. Her brain told her that doing so wouldn't be a good example for Desiree. Miss Julia relished the absolute control she had over the room. Foster was face down on the bed with his ass hovering in the air; Desiree was tied to the foot of the bed and drooling over Foster's ass; and she had the power over both. Yep, being warden at Creekwood was a sweet job.

Miss Julia sucked a finger into her mouth. She touched the finger to the opening of Foster's asshole and he winced, "Don't get wound up Foster. I'm not going to hurt you and I'm not going to do anything without telling you first. It's just my finger, I'm gonna loosen you with a bit first and lubricate the area," she told him in a calm, authoritative tone.

"I'm so damn horny! Can't I just fuck him for a few minutes first?" Desiree eyed his tiny bottom hopefully.

"Do you remember a new inmate at Creekwood max a year or two back? She had red hair and freckles, and a big bubbly butt. Her name was Vanessa. Do you know what she told me you did to her?" Miss Julia began to press her finger into Foster while she spoke. His hole was incredibly tight, warm, and caused a lot of friction for her finger which she wished was her cock. "She said you fucked her in the ass on her first day here and you didn't even use lubricant. That's rough." Desiree didn't respond, she just stared at Foster's ass. "I prefer natural lubricant. Spit and precum. When you're gonna fuck a guy, make sure you've prepared him for it like I am now. Foster's hole is so tight - I can barely move my finger. I'm sure you'd love it Desiree."

Foster grunted as her knuckle passed through his sphincter. His anal walls pulsed around her finger as it penetrated him. Miss Julia's cock was aching so badly, having it just inches from his pleasure hole and not diving into him took a lot of inner strength. She consoled herself by reasoning that she'd be balls deep inside him soon enough. That time finally came. She withdrew her finger and spat a glob onto her hand. Miss Julia stroked her shaft with it, making it shiny and sticky.

"Lemme fuck him first and I won't hurt him! Guuuhh! When I get out of here I'm gonna..."

Desiree didn't finish her sentence as at that very moment, Miss Julia pressed the head of her cock against Foster's asshole. "This time it's my cock Foster. I'm going to take it slow. It'll hurt at first, when you feel pain - stay calm. You'll forget the pain once it starts to feel good. You're gonna find out pretty quickly just how good my cock can make you feel." Miss Julia held his hips and began to enter him.

"Move your ass! I can't see." Desiree said from her vantage point at the foot of the bed.

"Oh! I'm sorry. Am I blocking?" Miss Julia asked coyly. She poked her ass out until it was right in Desiree's face. Desiree lunged forward and tried to bite it, but couldn't reach - Miss Julia's perfect butt and a sliver view of her asshole stared back at Desiree. "If you want a better view, you'll have to ask nicely."

Desiree exhaled hard and thrashed around on the bed again. She suddenly seemed like an adolescent girl who wasn't getting her way to Foster. Desiree was known as the biggest baddest bitch at Creekwood max and Miss Julia had reduced her to begging for a better view of the sex going on without her. He started to feel more comfortable with Miss Julia, almost like she was protecting him and taking care of him.

SugarandSalt
SugarandSalt
4,414 Followers