tagTranssexuals & CrossdressersShortening His Sentence Ch. 02

Shortening His Sentence Ch. 02

bySugarandSalt©

I knew when writing the first chapter that I'd get around to writing a follow-up chapter. This one definitely requires another installment sometime as well. I mentioned at the start of the last chapter that there wouldn't be tons of sex from the get-go, the same can't be said for this chapter. ;)

*

Foster's tongue lapped at Miss Julia's cock head. It'd been just a day and a half since Foster had sucked her cock that first night in her office. He was already learning the ropes. He was discovering all the little flicks of his tongue that sent pleasure tremors pulsing through her cock; the things that brought her that much closer to cumming.

"It's not like I'm feeding you to the wolves," Miss Julia told him, her fingers entwined in his hair. "You'll be safe as long as I'm there. Mmm... do it more there," Miss Julia said, responding to the movement of his lips around her shaft.

Foster used two hands to pump up the long stalk as her cock slipped from his lips and he said, "You said it yourself, Desiree doesn't really respond to authority." Foster placed Miss Julia's tip between his lips and sucked hard on the end while stroking her.

"I know what they say about Desiree: she's the baddest shemale at Creekwood max. Well, they're wrong. I am." Miss Julia pet his head gently, looking down on his cock-loving, "In her heart of hearts, Desiree knows that."

Foster looked up at her somewhat skeptically, but then dove his head down into her lap, taking as much of her shaft as he could. It pressed deep into his throat, and when his lips were nearly at the base, he swallowed hard and let his tongue dance around her underside.

Miss Julia moaned, then told him, "Keep that up and you'll have three loads from me in as many hours." Her balls were tightening, she could feel the cum rising. His tongue suddenly swept along the entire length of her cock and she nearly lost it. "I'm a little jealous today. I have to share you with Desiree. Promise me your sweet treasures won't belong to her afterward? I'd keep you to myself if I could." Foster looked up at her with those big eyes and started dislodge her cock from his throat to speak, but Miss Julia held him firmly. "Finish this first, love. I sure need it."

"ghmmmokay," he said around her cock.

Foster concentrated all his efforts on milking the jizm from Miss Julia's balls. His hand massaged her balls while he sucked her hard. Miss Julia couldn't stand up to this for long. She was already sweaty again. They'd only just showered thirty minutes ago; soaping up each other's bodies and letting the shower head wash over them.

"Here it is!" Miss Julia shouted down at him as her cock began to spew. Foster swallowed, with a few drops dribbling down his chin. Even though she'd just cum in the shower, there was still a lot of it. Miss Julia didn't let go of his head until she was sure he'd swallowed all of it. Her tip kept jerking and shooting in his mouth until finally the last drops slid down his throat. "You do such a good job at that."

***

Across the yard in Creekwood max, Desiree laid back on her bunk as a chubby shemale nursed on her breasts. The chubby shemale's name was Brenda. She was young, naive and willing to put out; exactly Desiree's kind of friend. Brenda teased Desiree's nipple with her tongue, but when her teeth accidentally grazed it, Desiree screamed. She shoved Brenda's mouth off her tit and yelled, "What the fuck was that!? No teeth!"

Desiree loved having her tits sucked. Her nipples had always been extra sensitive. She wanted her nipples nursed like a baby would, not with teeth. Any girl who knew enough to stay off her bad side knew that. Desiree roughly squeezed and pulled on Brenda's fat nipples and said, "Ain't you ever sucked titties before? Keep those fucking teeth to yourself."

"I'm sorry, Desiree. Do you want me to try again? Or I could try something else..." Brenda smiled, her hand sliding down Desiree's stomach and grabbing the shemale's massive cock. She gave Desiree a seductive wink.

Desiree pushed her hard against the wall. "I'm not wasting a load on you. You know where that cock is going tonight." Desiree wrapped her fist around her long, veiny shaft and gave it a slow stroke as she spoke, "I have a date with a little bitch tonight. No dumb slut is making me cum before tonight. That's for him to do." Desiree stood up and glanced down at Brenda, "Now hop off my bed and get out of here, piglet."

Brenda left Desiree's cell and walked through the zoo that was Creekwood max. A few girls who'd broken the rules and weren't allowed out of their cells waved at Desiree and tried to get her attention. One of them pulled out a titty and told her, "You can bite on these. Come here girl!"

She didn't pay much attention to them as she walked past. Then she bumped into a girl from her cell block. Teresa was a beautiful black shemale who looked downright amazonian, almost goddess-like. Brenda, who besides her more than ample curves and full lips, wasn't supermodel beautiful, had always been jealous.

"Hey there," Teresa said. "You seen Desiree today?"

"Yeah. I just left there."

"I was just heading to see her. How is she today?" Teresa smiled, her pearly white teeth on perfect display.

"Good mood, I think," Brenda lied and kept walking.

Brenda had been here six months now. She'd earned no respect in that time. Brenda had spent the entire time being passed around from girl to girl. She wanted to command the respect that Desiree did. She knew she never would, though, not while she was just another one of Creekwood max's good fucks and nothing more. Brenda's stomach growled, but she'd just had lunch.

"Hey, Brenda!" a voice called out behind her. Brenda turned around and another shemale she knew named Susan who she did favors for sometimes said, "I was just looking for you. I got something back in my cell we could make a trade for. How about it?"

A few minutes later they were back in Susan's cell on the bottom bunk naked. Brenda gritted her teeth as she lowered her butt down on Susan's spit-lubed cock. Susan moaned, holding Brenda's hips while bucking her own up. Susan enjoyed the view of Brenda's bubble butt sliding up and down her cock, so they always did reverse cowgirl. Once she'd taken all of it, Brenda started to bounce up and down, her fat ass slapping and slamming down on Susan.

***

Elsewhere at Creekwood max, back in Desiree's cell, Teresa sat on the bottom bunk while Desiree paced back and forth. "I tried. I couldn't get any information on tonight," Teresa told her.

"You tried everything?" Desiree asked her.

"The dude was tight-lipped about it," Teresa replied. "We weren't getting anywhere."

Desiree jumped on top of the startled Teresa and started to rip her clothes off, "You offered all this, whore?" Desiree shouted, her hand grabbing Teresa's ass. "You offered him this whore hole?" Desiree started to a jam a finger in and out of Teresa's tiny asshole.

One of the guards was sweet on Teresa. It usually only took a little flirting to get all the information about the comings and goings at Creekwood max and Creekwood min out of him. This time, though, he said he didn't know anything. Desiree found that unsettling. She wanted to know what Miss Julia was planning. It couldn't just be anything she wanted with Foster's butt tonight, there had to be strings attached when it came to Miss Julia.

Teresa's eyes were clenched shut. Desiree's finger slid in and out of her little hole while her other hand roughly massaged her ebony tits. "I'll try again," Teresa murmured.

"I'd fuck you right now if I weren't focused on tonight. Get your ass outta here before I change my mind," she told Teresa with a growl.

***

Foster was back in his room when Ed appeared. "Come on with me. I want to show you something," he said mysteriously. Foster barely had time to think before Ed was dragging him across the yard to Creekwood max. Foster entered the dark, scary prison again and got chills. They walked all the way to Miss Julia's office. Ed motioned for Foster to be quiet as he slowly opened the door. The layout of her Creekwood max office was quite similar to the one at Creekwood min, Foster thought. One difference was a second door in the room. Ed shushed him and opened the door, pushing Foster in, then shutting it behind him.

"You know I don't approve of prostitution in my prison." Miss Julia and another shemale were in the room. The other shemale was stark naked and tied to a table. Miss Julia circled the visibly shaken shemale and said, "Ed found you whoring yourself to another inmate. And for what?" Miss Julia lifted a box off the table and Foster could see it was a box of cookies. "For these? We don't feed you enough here?!"

"I'm sorry, Miss Julia. I'm sorry!" the girl cried.

Miss Julia turned back around and saw Foster standing there for the first time. "Foster, I didn't see you there. I was just disciplining an insubordinate inmate. Isn't that right, Brenda?"

"I'm sorry, Miss Julia. I won't do it again!"

Miss Julia's hand came down hard on one of Brenda's big butt cheeks and she squealed. There was a red smack mark where Miss Julia's hand had been. Miss Julia hit her again on the other cheek, which caused Brenda to squeal even louder. Miss Julia's skirt was tented. It made her look even more powerful to Foster.

"You're lying when you say you won't do it again. Someone else is going to come along and offer you their dessert for an after-dessert happy ending and you'll fall back into your old ways!" Miss Julia punctuated her remark with another hard smack on Brenda's bottom.

"I won't! Please, I won't. I promise!"

Miss Julia stopped spanking Brenda and started kneading her big butt cheeks; they were red and Foster felt his butt sting just looking at it. Miss Julia walked in front of the table and looked down at Brenda, who began to calm down. "I think we'll put you on a diet, Brenda." Miss Julia lifted up her skirt. She wasn't wearing any panties and Foster got a charge out of her seeing her hardened womanhood again.

Miss Julia plunged her cock into Brenda's mouth. "Suck it and maybe you'll get your cookies after all," she moaned. She started to snap her hips back and forth, fucking Brenda's face. Foster could hear loud sucking and slurping sounds as Brenda tried to blow Miss Julia through the face-fucking. Miss Julia grabbed her face and slammed her cock all the way down Brenda's throat. Tears were running down Brenda's face as Miss Julia held her cock there and stared the young shemale down.

Foster's cock had become painfully hard. It chafed against his prison uniform uncomfortably. Foster pulled his dick out without thinking and started stroking. Miss Julia heard it and looked up, she said, "I didn't tell you could do that."

The back of Foster's neck got red as he answered, "Sorry. I didn't mean to..."

Miss Julia ripped her cock from Brenda's lips and strolled over to Foster. He was still a little worried, but Miss Julia caressed his cheek soothingly and told him, "It's okay, baby. I'll give you something really nice to jerk that too." Miss Julia gave him a quick peck on the lips.

"I don't want to wear my dear Foster's asshole out before tonight. You're lucky, Brenda, that I don't feel the same way about yours. And from what I've heard, it's pretty loose already. Ed told me you'd fuck for a french fry." Miss Julia spread Brenda's bubbly cheeks. She spit in her hand and then rubbed it along her shaft. Miss Julia pressed her tip against Brenda's little hole and pushed through. Brenda grunted and Miss Julia said, "Hmm... feels plenty tight to me," then thrust deep into her asshole.

Miss Julia could feel Brenda's body shake. Brenda was scared and that made her tight asshole even tighter. It clung to Miss Julia's sizable package as she began to thrust in and out. Miss Julia held Brenda's hips and leaned down to whisper, "Now that I'm inside you, you can tell me. How do I stack up against some of the shemales at Creekwood max?" then giggled.

"Oh, Miss Julia! Please! Okay... yes... keep fucking me. I'm a fucking whore!"

Foster's cock couldn't have been any harder. He stroked it furiously as he watched the single most erotic sight of his entire life. Miss Julia was riding Brenda's fat ass like there was no tomorrow! He watched Miss Julia's butt bounce in time with her thrusting and her balls slap against Brenda's. Brenda whimpered under Miss Julia, her butt--still red with smack marks, wiggling.

"You're a good little fuck, Brenda. I can see why you're so popular. Mmm... I'm almost there." Miss Julia's thrusts were quicker now, harder; they had more need behind them. Miss Julia needed to cum and bad. "Foster, come here!" Miss Julia told him after a deep breath. He strode up beside her in a flash, his hard cock waving through the air as he did. "Suck his cock you dirty whore," she screamed at Brenda.

Foster was on cloud nine when Brenda sucked his cock into her mouth like a vacuum. Actually getting a blow job from a Creekwood max inmate, that just didn't happen! In a flash he had his entire length buried in her mouth and his balls pressed against her chin. She sucked wildly with Miss Julia fucking her behind like a woman possessed. Foster was just glad she didn't accidentally bite him as her lips and tongue worked together to pull him over the edge.

"This is what you wanted... come into my prison selling your body..." Miss Julia slapped Brenda's abused buttocks. "I'm CUMMING!" her eyes shot up to Foster's as she spoke. Once Miss Julia's words settled in the air, Foster felt the burning in his balls. Just moments later they were filling Brenda's body from both sides. "Swallow it like a fucking good t-girl whore," Miss Julia warned her.

Miss Julia continued cumming long after Brenda had swallowed Foster's last drops. He pulled his cock from Brenda's red, messy face and slipped it back inside his jumpsuit. Miss Julia panted, her hips still humping Brenda's backside. Her cock pulsed once more inside Brenda's asshole as she finally withdrew, Brenda's asshole clinging to her as she did.

"Ed!" Miss Julia shouted. No more than two seconds passed before he stepped into the back room and waited for her next direction. "Take Brenda back to her cell. Don't give her a prison uniform. Giving this whore clothes would be giving other girls the wrong impression. It's a free-for-all on her ass from now on."

Ed untied Brenda, her ego obviously bruised even more. Getting fucked by Miss Julia's and sucking off some Creekwood min bitch was something you didn't live down. Once they left, Miss Julia and Foster were all alone. She smiled at Foster and motioned him back into her office.

"Did we have fun today?" she asked him coyly.

"Oh yes, Miss Julia! This day has been the best," he told her, becoming a little shy afterward. He'd been fucked by Miss Julia twice and sucked her off as well, all in one day. What's more, he'd been happy doing it. Then he got blown by a Creekwood max girl! The old Foster, whoever he had been, he wasn't anymore.

***

Teresa walked softly through the halls. Away from the other girls, this place was eerily quiet. She could actually hear herself think for a change. The story of how she got mixed up with someone like Desiree is a long one. It could be worse, Teresa thought. She could be like Brenda.

She came upon a checkpoint and smiled to herself as she saw him; the guard that had been drooling over her luscious body since she arrived. He stood a little straighter when he saw her. She walked slowly, seductively, toward him.

"Hey you," she said in a playful, sexy voice.

"Hi," he told her, a big, country grin plastered on his face.

"Think you got a little time to spare?"

He led her to an empty room. The guard was enthralled by Teresa, he'd never seen a more beautiful ebony goddess. The room he led her to was a place where some of the guards took their lunch break. Teresa sat down on the table and flashed him a smile.

"Got anything more on what we talked about?" she asked.

"I guess one thing, but it isn't really important. I don't think so, at least." he shook his head.

Teresa grabbed him by his collar and pulled him closer, until he was in between her long ebony legs, she looked up at him. "Tell your honey girl, Teresa."

"Uhh..." he turned a little red, his eyes falling to the swell of her large bosom, "I'm really not supposed to."

Teresa shook his shoulders gently to get his attention again, then said, "How about for a blow job? That sound fair?" she licked her full lips until they shined perfectly.

"Oh hell. You'd let me do that?"

The dumb, horny guard thought she meant blow her! Shit, no use correcting him. She could use a blow job. "Of course, baby. Only if you promise I'll get my information afterward."

"I promise! I promise."

Teresa, with the air of a model even in her prison jumpsuit, pulled her thick, black pole out. The guard dropped to his knees and looked at it closely, his eyes lit up with desire. His stare had her womanhood growing in size. The day was really shaping up for Teresa.

Teresa moaned as his lips wrapped around her thick pipe. He sucked it into his mouth and started to bob his head up and down on it. Teresa pulled his guard cap off and put it on her head. A mirror would have been nice about now.

"Suck it. Yeah, that's good. Suck that cock real nice." Teresa stopped being as playful, she'd given a couple to survive, but hadn't been blown herself since arriving at Creekwood max. The guard's tongue rolled around her girth and then teased her tip until she was leaking precum. His hands reached around her back and grabbed her full, sculpted ass. He groped it in his hands and started to take more of her shaft.

Teresa's toes scrunched as she entered his throat. He started to deep throat her. Teresa was glad she'd sat down, because the pleasure would have been too much for her standing. One of his hands let go of her ass globe and slipped inside her jumpsuit for a handful of tit meat. Teresa had never been more surprised in her life. This country boy was pretty smooth, and he could deep throat too!

She loved watching him blow her; her jet black cock sliding in and out of his pretty pink lips. Teresa held the back of his head and thrust her hips forward, forcing almost every inch of her length into his mouth. She could feel his throat contract around her prick. He looked up at her, his eyes welling up just a bit, pure desire on both of their faces. Teresa didn't want to end so soon, but she was ready to cum.

"You're good at this. Making me cum so fast. Your sweet mouth." Teresa let out a low moan and began to ejaculate. Her sleek black balls churned, sending globs of semen up her long shaft and out her tip. He swallowed every drop of it, greedily continuing to suck even after she'd given him everything.

Teresa caught her breath and asked, "Now how's about that information?" The guard slowly let her shrinking cock slide out of his mouth and looked up at her with that same, dazed, silly country boy grin.

***

"What the hell's been going on with you?" Kevin asked Foster.

"Look," Foster said, "I can't tell you everything."

Kevin didn't like that answer. He sat down and asked, "What can you tell me?"

Foster actually didn't know how much he was allowed to divulge to anyone at Creekwood min. If they knew that Miss Julia was having him sleep with a Creekwood max inmate, this place might go crazy. Everyone was deathly afraid of those shemales. Foster pictured Desiree and understood why.

"I'm not sure. Miss Julia has me doing a lot of things for her. That's all."

"Things? What does that mean! Why did you want to know about Desiree yesterday and why do you keep disappearing?" Foster sighed, then looked around for a moment, and decided to let him on what was going on tonight. Kevin looked more and more worried as Foster told him the story. "Fuck..." was all he could say once Foster had finished.

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