Small Penis Prison Ch. 12

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Ryan realizes that the days in prison are going to be long.
4.6k words
4.63
7.9k
7

Part 12 of the 32 part series

Updated 04/27/2024
Created 06/20/2023
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Lordoflol
Lordoflol
128 Followers

Ryan was exhausted, his balls ached like never before and his cock was hard as hell, dripping precum uncontrollably. He stayed in bed lying down looking at the rest.

The rest of the men were in a similar situation to him, sweaty and in pain on their faces, with their hard, throbbing cocks and their swollen, blue balls.

He saw some of them get up and go to the bathroom, to throw cold water on, he supposed.

He noticed John, the man's face was red and sweaty and he was gritting his teeth as his eyes watched as his tiny cock trembled and danced while beads of precum trickled down from the tip down to his already coated balls.

"John!" Charlie yelled walking into her office with Mia, "To my office, now!"

John flinched, then got up quickly and headed for Charlie's office with terror on his face as he left a trail of precum along the way.

Ryan knew what was going to happen inside the office.

"Poor guy..." Ryan said to himself almost muttering

Then Samuel approached his bed, the man had a raging erection and his balls were quite swollen.

"How was your first session?" he asked.

"Horrible, my balls hurt like never before, I don't know how you can put up with all this, plus all that stuff about jerk off instructions and edging games has had me on edge all the time, after all it was what I I liked to watch when I masturbated at home." Ryan said with a sad smile.

"What are you taking about?" Samuel asked confused, "What was your video about?"

"Well, it was a video of Charlie giving me instructions on how to jerk off while interspersed with videos of her fucking and then Mia fucking, and stuff like that all the time, for the 3 hours." Ryan said, "Wasn't yours something like that?"

"No way!" Samuel exclaimed, still confused, "Upon arrival, she does a kind of test for each of us and then, based on the results, she shows us videos of what she knows will make us hornier and we jerk off at our own pace, at least we have to get to 30 edges at the end of the session, if we don't get there she punishes us."

"And how does she know if you've reached 30?" Ryan asked.

"I have no idea, but you know." Samuel said, "There are cameras everywhere, maybe that's why, although I think she has some kind of sixth sense that makes her aware of that kind of thing, that woman is a demon."

"And what are your videos about?" Ryan asked curiously.

"Well I'm an ass man, so the videos focus on that, beautiful women with big round asses, dancing, twerking, fucking, anal, etc., although from time to time there are boobs and something else, but especially butts, butts everywhere, lots of butts..." Samuel said as if engrossed, remembering the video while his cock seemed to be throbbing again, "For the rest are similar videos, although changing the theme, there are some who like boobs, other feet, John for example is obsessed with schoolgirls, cheerleaders and things like that."

Then they began to hear a banging from inside Charlie's office while Mia and Charlie laughed.

Ryan knew what it was, they were already finishing and Charlie had started punching John in the balls.

Ryan winced at the memory of the poor man biting hard on that stick while drooling.

After a while John came out of the office, staggered to his bed, looking dizzy and had a continuous grimace on his face.

"What a bitch." Samuel muttered, "If ours is torture, that man's is hell."

"Samuel and Ryan, come to my office!" Charlie exclaimed.

Ryan was startled.

Samuel made a terrified face that made Ryan worry even more.

They entered the office and there they were both sitting smiling at them.

"Shut the door!" Charlie ordered.

They both stood in front of the table.

"Seems like you've become friends, right?" asked Charlie smiling, "What are you all talking about?"

The men looked at her in silence.

"Answer!" Charlie ordered.

"Nothing, I explained to him a little about what life was like here so that he could adapt as soon as possible."

Samuel responded quickly, trembling with fear.

"What a good boy..." Charlie said, "You wouldn't be talking bad about me, would you?"

"No, no, of course not." Samuel said, trembling even more.

"Are you sure?" Charlie asked raising an eyebrow while still smiling.

"Yes, yes, I swear." replied Samuel stuttering.

"Very good, I believe you, I already knew you were a good boy." Charlie said, "Come closer!"

Samuel came to her side.

"And how is life here, then?" Charlie asked as she grabbed him by the balls.

"Well, I was explaining..." Samuel began to shake and get stuck, Charlie was crushing his balls with her hand.

"Keep going." she said smiling as she squeezed his balls harder.

"I told him that life here wasn't so bad, that you were an understanding and fair girl and that if he behaved well, he wouldn't have any problems." Samuel said through clenched teeth as Charlie squeezed his balls even harder.

"Very good!" Charlie said releasing the pressure a bit, "Would you say he was lucky?"

"Yes, of course, he could have gotten a much worse girl." he said with a relieved face.

"Oh yeah?" Charlie asked amused, "Like who?"

"Like Freya or Kayla, from what I know they are much worse." He said.

"Ah ok, would you say they are sadistic bitches?" Charlie asked, squeezing his balls again.

"I guess..." he said without thinking clearly because of the pain in his balls that little by little Charlie squeezed harder.

"So you're saying that my friends are bitches?" she said very seriously.

"No, no, I didn't mean..." then Charlie started punching him in the balls really hard relentlessly while Mia started laughing out loud.

She kept going like that for half a minute, the man jumping with each punch while gritting his teeth.

"Could you explain this to me anyway?" Charlie said when she stopped.

Then she approached the computer and gave several clicks with the mouse while looking at the screen.

Then the audios of the conversations they had had since the morning began to be heard.

"'Don't trust appearances, even though she looks like an angel, she's a real devil.', 'But that doesn't make Charlie good, far from it', 'What a bitch.'" that last bitch resonated as if there was echo in the room.

"So I'm the devil and a bitch?" Charlie said smiling, "Is that it?"

"No, no, it wasn't about you." Samuel was shaking non-stop.

"And now you lie to me." Charlie said quietly, "I always thought you were a good boy, what a disappointment."

"Yes, I'm a good boy, I'm sorry, I'm sorry, it won't happen again, I swear." he said very afraid, "Please forgive me."

Then someone knocked on the door. It opened and Freya appeared.

She was wearing a tiny pink bikini that barely covered her massive tits and jean shorts.

"Hello Charlie!" she said very seriously, "Did you call me?"

"Hello Freya!" Charlie said smiling, "Right on time!"

"Here, my boy Sam and I were having a very interesting talk." she said still smiling, "He says that I am the devil and a bitch, and that you are also a bitch but much worse, what do you think?"

Freya approached Samuel and kicked him in the balls lifting him off the ground several feet, the man screamed inconsolably and grabbed his balls, throwing himself to the ground.

"So a pervert like you thinks I'm a fucking bitch, huh?" Freya said.

"Why don't you take him with you for a week to show him that you're not a bitch at all?" Charlie asked, "So when he comes back to me he'll also appreciate how well I treat him, how about that little boy?"

"It will be a pleasure." Freya said grabbing Samuel by the balls and dragging him across the floor to the exit.

"Noooooo, please, nooooo!" Samuel yelled desperately, "I'll be good, I promise, it won't happen again!" he said as the door closed behind them, though they still heard his screams as they walked away.

"Of that I am sure." Charlie said smiling,

"Ryan, this is just so you know, there are cameras and microphones everywhere here, before you badmouth any of the girls, think twice, okay?"

"I understand." replied Ryan scared to death.

"Don't worry, I know that you are a very good boy, aren't you?" she asked smiling.

"Yes, of course." he responded quickly. "Good boy!" Charlie said, "Now go back to your buddies, and lock the door on your way out."

Ryan sat down to watch TV next to the man in his forties he'd met at the showers.

"I am Richard." the man said, "Ryan, right?"

"Yeah." Ryan said, still thinking of Samuel, worried.

"I always tell Sam not to talk too much, that mouth of his would end up causing him trouble." he said with a sad smile, "You see, in the end I was right."

"The best thing is not to think too much, I am erect for 24 hours and with pain in my balls, but I can't do anything, right?" Richard said, "I have a couple of months left and I'll be free, I've been here almost 4 years and the best advice I can give you is this, don't get involved in other people's business, don't get in trouble and do everything what they tell you, if you do all that you will do much better." and he kept watching TV.

Ryan stared at the TV, everything they put out seemed sexy or provocative to him, he didn't know if there was some kind of special filter or it was simply because of the state he was in.

"Even if you change the channel, they always show the same kind of shit." Richard said.

One channel was showing Cool Hand Luke, just the scene where Joy Harmon comes out cleaning the car with her tits bouncing up and down, Ryan's dick started to throb, Richard changed the channel, it was one of those reality shows where they come out muscular men and beautiful half-naked women looking for 'love', he changed the channel again and there was a parade of lingerie models, women bombshells with their tits and asses bouncing as they walked, that was too much, Ryan thought, getting up and going to his bed.

"I already told you, they only play shit." Richard said, still watching TV.

Soon it was time for lunch. They went to the dining room, again the same food from the morning, he ate without talking to anyone and then he returned to the room with the rest.

Ryan was very tired, he hadn't slept at all with the erection he had. He inadvertently fell asleep, had a nightmare in which he was in hell and a succubus very similar to Charlie kept edging him over and over again for all eternity until he suddenly woke up to Charlie's screams.

"Come on guys!" Charlie exclaimed. "Come here!"

The men gathered around her and Mia.

"Today I won't be able to be with you for the afternoon exercises." She said, "Mia and I have plans for this afternoon, but don't worry, Ilsa, my personal trainer, is coming, I've already explained to her what she had to do and she's delighted, she'll come in a few moments, I'll be back at night."

Suddenly the door opened.

"Hello!" said a smiling girl who appeared by the door.

"Hello Ilsa!" Charlie said motioning for her to come closer, "I was just telling the guys about you."

The girl was in her early twenties, she was very tall, almost 6'4 feet, blonde, blue eyes and a beautiful face, she had her hair in a ponytail, m quite muscular and was wearing tight and very short red leggings that marked her big round ass and a very tight top that squeezed her huge tits, they were really huge, they had nothing to envy to Freya's, when she walked closer they bounced up and down, they were definitely natural.

"She is Ilsa, she is from Sweden but she has been here for more than ten years, she has been my personal trainer for several years, I hope you make them sweat as much as I do." Charlie said as she winked at her smiling.

"That's for sure." Ilsa said with a slight accent.

"Well, we're going now." Charlie said, "Bye guys, have fun!"

Ryan watched as Charlie and Mia headed for the door and couldn't stop watching Charlie's thong-clad ass wiggle as she left, his cock throbbing.

"Okay guys, let's get started." Ilsa said, "Everyone to bed, with your tiny cocks in your hands."

"I don't know how Charlie does it but I want you to jerk off to the beat of the music, I'll be watching you." she said winking at them with a smile.

Ryan sat on his bed leaning his back against the headboard when he saw the rest get into a similar position. He thought he saw the other boys looking confident, perhaps thinking that Charlie not being there would make it easier.

"Let us begin!" she said taking a remote and putting on music, it was quite hard electronic music.

The music started slowly but gradually increased the pace, Ryan followed the rhythm with his hand.

Ilsa did aerobics to the music, her tits bobbing from side to side.

Suddenly a very fast rhythm came, Ryan barely managed to keep up, if he kept up a little more he would come, plus Ilsa's bouncing tits about to come out of the top didn't help at all.

Suddenly he was on the edge and he pulled his hand away to keep himself from coming.

"Hey you, little boy!" she yelled at him without stopping dancing, "Get back to grab your tiny dick right now!"

"But I was on the edge, I either stopped or cum." he said.

"I don't care, do like your little friends, but don't stop playing with that little thing!" she yelled at him pointing to the rest.

Ryan looked at the rest, they were all jerking off to the rhythm of the music but stroking their cock with only the tips of their fingers to avoid cumming, then he realized when he saw their faces, they were all riding the edge.

He jerked off again to the rhythm of the music but following the technique of his buddies, just brushing his cock with the tips of his fingers. Anyway, in a few minutes he was back on the edge and continued riding it.

That was torture, despite the pace going up and down, he was still on the edge the whole time while a monument of a woman danced in front of them with her tits bouncing non-stop and her chiseled ass wiggling from side to side.

After a long while of music, aerobics and edging, Ilsa stopped and the men stopped jerking off.

Ilsa was sweating profusely, beads of sweat falling between her tits.

"Now, Spinning!" Ilsa said, "Just like before, jerk off to the music."

She got on the stationary bike and began the exercise. When the rhythm of the music increased, she got up and pedaled faster, when it decreased, she sat down and pedaled slowly.

"Faster, boys!" she yelled getting up from the chair and moving her ass with each pedal stroke while her huge tits bounced continuously.

Ryan suffered staying on the edge, brushing his cock to the rhythm of the music watching that goddess sweating and her ass and tits bouncing endlessly.

He didn't know how long it had been but it seemed like an eternity to him, when the music stopped and Ilsa got off the bike.

"Damn, it's really hot in here!" Ilsa exclaimed, still sweating profusely.

Then she took off her top revealing her huge and beautiful tits, she had a piercing on her left nipple, despite being massive, gravity seemed to have no effect on them, they were perky and round.

Then she took off her leggings and was left with only a white thong with little red hearts.

That ass was a masterpiece, chiseled by the

gods. She had several tattoos that had been covered by clothing. She had a tattoo of a Q inside a black pike on her right buttock, "Daddy's little whore" on her left hip, a phrase just below her left buttock that Ryan couldn't quite see, "Jungle Fever" below her left boob and finally a voluptuous version of tinkerbell with her legs open and raising her skirt, in the lower part of her back.

"That's better." she said rubbing the sweat from her tits, "What are you looking at?" she asked.

"Ah, my tattoos." she said laughing.

She started to tell them what each tattoo was in case they couldn't see it, when she got to the sentence that was under his left buttock she read it, "Pussy tighter than a wet suit." and she laughed out loud.

"But I still have one left that you can't see." she said leeringly.

She lowered her thong a little and just above her pubic hair in the shape of a triangle it read "BBC ONLY"

"As you can suppose I am a queen of spades, or what is the same, I only fuck black men." she said, "My hubby didn't like the idea, but after a long time in his chastity cage he got used to it, I guess."

"What can I say, I'm in love with big black cocks." she said letting out a laugh while her tits bounced all over the place.

Ryan was getting more turned on by all of this, if that was possible.

"Okay, now step!" she said pulling out a platform.

The music started again and Ryan's agony too, but this time much worse, seeing that perfect woman jumping over and over again while her huge tits bounced to the rhythm of the music, every time she bent down her perfect ass was fully exposed, that was too much, Ryan only raised and lowered his hand brushing his cock from time to time and still kept riding the edge all the time.

They continued like this for a long time until the music stopped again, under his balls there was a puddle of precum and it kept falling endlessly from the tip.

"Lastly I like to finish with a bit of Pilates." she said, "For this I like to play classical music."

"How about the four seasons?" she said smiling, sweating profusely.

Then Vivaldi's spring began as she did pilates and stretching exercises.

After spring came summer, she began to do the splits, Ryan almost came when he saw her with her legs wide open, flexing her buttocks to the rhythm of Vivaldi.

Then fall, she kept stretching while emitting little moans, that was too much, she leaned on her elbows and her knees stretching one leg at a time with her huge tits hanging and swaying.

Finally, she spent the whole winter doing squats, seeing her big and beautiful ass, made Ryan ride the edge with every slight touch.

When they were halfway through winter the door opened, it was Mia and Charlie chatting.

As soon as they saw them Charlie stopped.

"Are you still doing the exercises?" she asked confused, "It's been almost 3 hours."

"I'm sorry." Ilsa said smiling, getting up sweaty, "You know that when I start exercising, time goes by without me noticing."

Charlie and Mia burst into laughter.

"Okay, do not worry." Charlie said still laughing, "A little cardio wouldn't hurt the boys."

"Can we join?" Mia asked.

"Yeah, sure, it'll be fun!" Charlie exclaimed. "Of course!" Ilsa said smiling brightly, "I was doing pilates."

The three of them began to do pilates, Ryan noticed the rest of the men, they were sweating, clenching their teeth, puffing and doing anything to avoid cumming while they continued riding the edge.

Mia and Charlie were still in bikinis and thongs. Charlie and Ilsa doing the splits and Mia trying, but she couldn't quite spread her legs.

Ryan spent the rest of the winter riding edge almost without touching his cock, and the three of them did squats nonstop until winter was over.

Three perfect asses moving up and down to the rhythm of Vivaldi's winter while Ryan jerked off, it should be Heaven, but it was Hell.

When the music ended, the three of them got up.

"Okay boys, you can stop!" Charlie said.

"Girl, what a great body you have, huh?" Charlie told Ilsa, admiring her body.

"You see, years of training." she said proudly.

"No, no, there's genetics here too." Charlie said tugging at Ilsa's nipple piercing as she smiled.

"Hey!" Ilsa exclaimed, laughing, slapping her on the hand.

Ryan's cock trembled and throbbed continuously.

"Hey, I like your tattoos!" Charlie exclaimed,

"What does it say here?" she said bending down and looking at the phrase she had tattooed under her buttock. "Oooh, what a naughty girl!" Charlie said with a laugh.

"The truth is I'm a very, very, very naughty girl." Ilsa said winking at her and laughing.

Lordoflol
Lordoflol
128 Followers
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