Small Penis Prison Ch. 16

Ryan watched as Charlie walked through the door and turned on the lights. He had been awake for a long time. After a month in the SPP sleeping was very difficult, between the continuous horrible pain in his balls and the constant erection he was not able to sleep a wink.

"Ryan, you have a visitor." Charlie exclaimed.

Once a month the inmates had visitors, Ryan assumed they would be his parents.

After showers and breakfast he went to the visiting room, there was his mother with his lawyer.

"Hi Ryan." she said very seriously.

"Hi Mom." he said without looking at her face.

"I'm very disappointed in you, how could you end up like this?" she asked him.

"I haven't done anything, someone has set me up." he said.

"I would believe you if it weren't for the various Charlotte's thongs we found under your bed and the countless videos and photos you had of her on your computer." she said looking into his eyes very seriously.

Ryan was silent and blushed, he had forgotten about the thongs.

"Ryan, this is very serious." said Stacy, her lawyer, "They have sentenced you to 5 years and at first everything was very strange, a quick trial and practically without evidence, it seemed rigged, but now in view of the photos and videos and the stolen underwear, even if we appeal we are going to lose."

Ryan was silent looking at the two of them. Without thinking, he realized that he had an erection, his lawyer was a very pretty brunette girl in her early 30s, she was dressed very formally with a gray jacket, skirt and heels, but underneath he could see that she had a very nice body, only with that and his condition made Ryan unable to think of anything other than imagining her naked.

"Are you listening to me?" Stacy said, "Only a miracle would get you released, either that or Charlotte drop the complaint."

"Charlotte?" he asked, "She was the one who denounced me?"

"Well of course." Stacy said, "Didn't you know that?"

They continued talking about legal issues but he could only think that Charlotte had deceived him from the beginning, it was her fault that he was stuck here and she had made him believe that she didn't know anything, what a fool he had been.

Ryan stormed into Charlie's office.

"Hello Ryan!" Charlie greeted him smiling, "Ready for your big day? Today you will have your chance to cum."

"You've fooled me all this time!" he yelled at her, "I'm locked in here because of you!"

"Look, Ryan, first of all, if you yell at me again, forget about cumming for a looong time, second, yes, you're here because of me, I sued you because I was sick of you spying on me all the time while you jerked off that tiny dick of yours, third, it made me veeery horny." she said letting out a laugh.

"It's not funny." he said very seriously.

"Yes it is, also remember that here there are cameras everywhere, I heard your conversation with your lawyer, the one who's really angry is me, I thought you were just spying on me, but I see that you were recording me and stealing my underwear, You're a fucking pervert." she said very seriously, "Let me tell you the truth, at first all this was some kind of punishment for spying on me but since you are a real stalker you deserve all this."

"I'm not a stalker, I'm in love with you!" he yelled at her.

"What?" she said, freezing.

Ryan began to blush, he had said it out loud.

"You're not in love with me, don't talk nonsense." she said smiling.

"Yes I am." Ryan decided that once he had started he would tell her the whole truth, "I've been in love with you since the first time I saw you, 5 years ago when you moved in next door you seemed like the most beautiful woman I've ever seen in my entire life, and then, the few times we spoke you seemed charming, funny, happy, intelligent, you're perfect."

Now the one who was turning red was Charlie.

"What are you saying, have you been in love with me all this time?" she said blushing.

"Yes, we also have the same tastes, we like fantasy and science fiction movies, we are both fans of Star Wars." he said very seriously.

"But...how do you know all that?" she asked almost speechless.

"Of the few times we talked, we talked about that kind of thing, books we had read, etc. At first when you moved we talked a lot but since you started dating Marcus we practically stopped talking." Ryan said.

"It's true, we got along very well, I always found you charming. Why didn't you ever tell me how you felt?" she asked.

"I don't know, it seemed like I didn't have a chance." he said looking at the ground.

"Don't be silly, to tell you the truth you are quite handsome, maybe I would have said yes, if you had asked me out." she said smiling.

"And what about the size of my dick?" he asked blushing.

"Yes, that would have been a problem, really." she said thoughtfully.

"And the fact that you only fuck black men?" he said even redder.

"Well, until I met Marcus, I was also fucking white men." she said smiling, "Well enough, let's stop with this nonsense. You have to roll the dice to see if you can cum."

"So you're not going to drop the complaint?" asked Ryan seriously.

"Of course not." Charlie said.

"Good bye." Ryan said, and left closing the door.

He lay down on his bed in a rage, he didn't care about cumming, he didn't care about anything, he only thought about that spoiled girl, because of her he was stuck here.

After a while Gina appeared through the door and went to Charlie's office, they were inside for a while.

"Ryan, come here!" Gina called from the office.

Ryan entered the office, after having been thinking for half an hour the anger had turned into fear, he didn't know what would happen now after having spoken to Charlotte like that.

"Ryan, Charlie told me that you've been behaving very badly." Gina said seriously.

Ryan looked at Charlie, she was looking at the floor.

"We have decided that you are going to spend a week with Freya so that you understand what respect towards girls is." Gina continued.

"What? That's not fair, I haven't done anything." he yelled looking at Charlie.

Gina gave him a tremendous kick in the balls.

"If you scream again, instead of a week it will be a month." she said, Ryan was sprawled on the ground clutching his balls in excruciating pain, "Now follow me, and not another word."

"Don't worry honey, after this week he'll be a new boy." Gina said with a wink at Charlie as they walked out of the office.

Ryan glared at Charlie as he left the office, she didn't say anything.

By the time they got to Freya's side, Ryan was shaking.

"Another little pervert being mean to Charlie." Freya said looking into his eyes, "I'll show you how I treat little boys like you."

She was quite a bit shorter than Ryan but she was scary.

"I'll take care of him Gina, you can go." Freya told Gina.

"Okay, all yours." Gina said as she left.

"Now we are going to have fun, you and me." Freya said with a smile, Ryan couldn't stop looking at her huge tits, she was wearing a black latex jumpsuit that covered her entire body but had the front zipper pulled down almost to her belly button which made her big braless tits stick out and they would bounce with each step although without coming out completely, covering her nipples, her pink hair was shaved on one side and the other with braids and she was wearing knee-high boots with a metal tip.

She tied him to a cross leaving him with his legs open and his balls completely exposed.

"Let's start with 20 little kicks." Freya said smiling.

Ryan looked around the rest of the room and there were several men tied to chairs, in chastity cages, all with huge blue balls covered in marks and bruises.

Then came the first kick, it was indescribable pain, any other kick that had been given to him since he was there was a mere touch compared to that kick, he let out a piercing scream.

"Are you ready for the next one?" Freya said smiling as she delivered another terrifying kick to Ryan's balls.

Ryan was gasping for breath, the pain was excruciating.

Upon reaching the tenth kick Ryan was knocked unconscious from the pain.

He woke up to Freya slapping his face.

"Wake up weakling!" Freya yelled at him, "You still have 10 more to go!"

While he was regaining consciousness, Freya gave him another strong kick that ended up waking him up completely.

Ryan screamed again with all his might in pain.

When they reached the last kick he was shaking with pain, he couldn't even speak, it was the biggest pain he had ever felt in his life and he was half dizzy.

"Okay, now we're going to put you in your cage." Freya said very seriously.

She went to grab the chastity cage and knelt under him, despite the pain seeing her tits spilling out of the latex bodysuit was making his cock hard.

It was an inverted cage, in the process of putting it on, Freya crushed his cock against his pelvis, causing him severe pain due to his erection, but despite his screams, Freya continued without flinching until after a while he already had the cage on.

Then he saw the state of his balls, very swollen and full of bruises from the kicks that Freya had given him, they seemed even bigger due to the fact that where his cock should have been there was only a metal plug.

"Perfect." Freya said smiling, "Charlie told me that today was your chance to cum, so to show you that I'm not that bad I'm going to let you empty those big balls of yours a bit."

Then Freya untied him from the cross, Ryan almost fell to the ground, he was dizzy, and the pain in his balls was unbearable.

She tied him to a wooden rack with holes in the front where he put his hands, he was tied on all fours on top of the rack without being able to move an inch.

"Since I know you have no experience, I'll do it gently at first." Freya said walking up to him and squatting down facing Ryan, "That's how my boys cum every 6 months, if they don't cum after 1 hour they weren't desperate enough and we'll try again after 6 months.", some have been here for more than 3 years and still have not come, bad luck." Ryan looked at her confused.

Then she got up and he listened to her behind him for a few minutes until she appeared again in front of him and he understood everything.

"What do you think?" asked Freya smiling.

Ryan looked at her with his mouth and eyes wide, she was wearing a strapon with a dildo at least 9 inches and very thick. Then Ryan started shaking, this was going to hurt.

"Wait, the last touch is missing." she said putting a rubber ball in his mouth and tying it behind his neck, "That's better, the first time is usually quite noisy."

He heard her get behind him and then he felt it, something big slowly trying to enter his ass.

She continued slowly inserting the dildo while he screamed inconsolably, it seemed to him that she was going to break him in half.

Until he noticed how he had it all inside his body, that was a horrible pain, he screamed non-stop through the rubber ball.

"You like it huh? What a bitch!" Freya said.

Then she took it out completely and put it back in all at once.

Then slowly she began to pick up speed, after a few minutes she was pounding him like a jackhammer, and then the screams began to change to moans of pleasure, despite the tremendous pain, she was hitting something inside him that gave him some pleasure over and over again.

"Look, you're dripping like a nasty bitch!"

Freya exclaimed laughing as she kept pounding him relentlessly.

She continued like this for half an hour, it was very frustrating because despite giving him some pleasure he was not able to reach orgasm, although he noticed how his cock was dripping all the time.

"Let's level up a bit." Freya said.

Then she showed up with a bigger, thicker dildo full of little bumps.

"How about this one, you little bitch?" she said slapping him with the dildo in the face.

Ryan was freaking out, that was huge.

When she began to penetrate him, he began to scream again, that was too much.

"If you yell like a bitch I'll have to treat you like one." Freya said laughing as she slammed the whole dildo into his ass. Ryan gasped, then she went back to pumping like before. They spent another half hour like this, without stopping.

Ryan was sweating, his ass on fire, his cock trying to get hard inside its tiny cage as precum dripped nonstop and his balls ached like never before in his life.

"We're done. I'm sorry you didn't come, but you've released a lot of precum, if it's any consolation." Freya said giving him a spanking in the ass.

She untied him and freed him from the rack.

"Look at all that mess you've made!" she said pointing to a huge puddle of precum under the rack, "Now you're going to lick every last drop."

She took the rubber ball out of his mouth and smashed his face into the puddle of precum.

"Lick it!" she commanded.

He began to lick it as she got behind him and kicked him with all her might in the balls. Ryan cried out loudly.

"Until everything is clean, I'll keep kicking you." she said laughing.

They went on like this for 5 minutes until there was no trace of the puddle of precum, while Ryan cried in pain with each kick, he lost count of how many kicks Freya gave him in the balls.

"Good boy." Freya said, "Now go sit next to your buddies."

Ryan went trembling to the free chair, when he got there he saw that in the middle of the seat there was a 7-inch dildo attached, not as thick as the others but quite a bit.

He turned around confused looking at Freya.

"Sit there right now if you don't want any more kicks in those big balls of yours, little boy!" she exclaimed very seriously.

Ryan began to sit down letting the dildo slowly penetrate him aching and moaning with every inch until his ass touched the seat.

"Perfect!" Freya exclaimed smiling, "Don't even think about getting up!"

Freya walked over to Ryan and tied him to the chair.

"Now let me explain how things are around here." she said, looking into his eyes, "Every morning when I wake you up you will go to shower and have breakfast, then you will sit in your chairs waiting for your turn, when your turn comes I will punish you as I see fit, I will only give you a hint, pain, a lot of pain." she said smiling, "Then you will go to eat and when you come back you will sit in the chairs again, in the afternoons for 4 hours while you are sitting in your chairs I will put some videos on you while a machine slaps your balls over and over again."

"Before bed you will go to dinner and then a pegging session with each of you, before bed I will put a buttplug on you and I will check your balls, if they are not the size and color that I like I will hit them again until they are to my liking, then to bed everyone." she said with a sadistic smile, "Those are normal days but every once in a while there are surprises, you'll see." and winked at him.

Ryan sat with a great pain in his balls and ass as he watched as one by one Freya released each of her quivering boys to punch, kick and spank them until she got tired and tied them back to their chairs to untie the next, she was like this all morning with the screams of the boys resounding throughout the room, that woman was tireless.

When she was done, Freya released all the boys and sent them to the dining room.

Ryan followed the rest of the boys walking with difficulty because of the intense pain in his ass, no one spoke, they were all trembling as they looked at the ground, all of their bodies were full of marks, bumps and bruises, and their balls were in a sorry state, very swollen and blue.

Returning from the meal, everyone sat down in the chairs without saying a word, Ryan sat down in pain.

They began to hear moans coming from Freya's office, after a few minutes she came out of her office in a purple bra and thong, the bra squeezed her gigantic tits that bounced with every step she took, she was sweating and her face was red.

Behind Freya came a huge, heavily muscled man in a black suit.

"See you tonight." she said laughing giving him a spanking on the ass.

"Yes my Lady." he said very seriously kneeling down and kissing her feet.

"You can go." Freya said.

"Okay pervs, I'm with you now." she said smiling as the man left, "That big man is my boyfriend Lance, everything you boys aren't, a real man with a huge dick."

Then she put a screen in front of each boy and she knelt in front of each chair opening a hole that left his balls dangling and exposed.

She took several machines and put them under each chair. The machines were a kind of crank with a wooden paddle attached to the tip.

"Look loser, since it's your first time I'm going to show you how it works." Freya said looking at Ryan with a mischievous smile.

Then she pressed a button and the paddle began to slowly hit the air over and over again, she was hitting a wheel to increase the speed and the paddle hit faster and faster until at the end it was hitting non-stop at full speed.

"See where it hits? That's where your balls go." she said with a laugh, her huge tits bouncing up and down.

She placed it just under the chair and stood up.

"Now I'm going to cover your mouths otherwise this is going to be very noisy, don't you think?" he said looking at Ryan.

She took several rubber balls and put them in the mouths of each one, tying them to their necks.

Then she put headphones on them and turned on the screens.

"Enjoy the movie." she said laughing as she began to activate the machines.

When she activated Ryan's suddenly he felt a sharp thud on his balls, and another, and another, 1 per second as the video started.

It hurt less than Freya's kicks but 1 hit per second for 4 hours, that was going to be a real nightmare.

Ryan stared at the screen, moaning in pain with each blow to his balls. The video consisted of clips of black men with huge cocks fucking girls mixed with Freya's voice calling them betaboys, pervs, small dick losers, etc. then images of girls in swimsuits undressing but without seeing anything because it was censored at the right time, then clips of Freya hitting different guys hard in the balls and laughing while looking at the camera.

It went on and on as the paddle kept hitting him in the balls.

Freya sat looking at her phone and from time to time she looked up and smiled seeing how her boys suffered.

During the 4 long hours that the session lasted, Freya left and entered the room from time to time, increasing the speed of the blows or lowering it as she pleased.

Ryan was in extreme pain in his balls from the constant pounding, screaming and drooling through the rubber ball.

Freya walked over to Ryan and picked up one of his headphones.

"Last 5 minutes little boy." she whispered in her ear, "Be strong."

Then she went up to full speed and the paddle began to hit him hard at top speed like a machine gun.

Ryan screamed with all his might as Freya put the headphones back on him and looked into his eyes smiling.

At the end of the 5 minutes Freya turned off the machine and the screen and took off the headphones.

"How was the experience, little boy?" she asked smiling as she fingered a nipple through her bra.

Ryan couldn't even speak, his throat hurt from yelling and the pain in his balls was indescribable.

"Did the cat get your tongue?" she said with a smile, sitting on top of Ryan, "Darling, you're in for a long week with me."

She took the rubber ball out of his mouth as she rubbed her huge tits against his chest.

"Do you like my tits? My nipples are as hard as diamonds." she said keeping her tits pressed against his chest with her face inches from Ryan's, then she licked a tear from Ryan's cheek, "Mmmmm how I like the taste of desperation." she said letting out a laugh.

Ryan felt his cock begin to throb inside its tiny cage.