Small Penis Prison Ch. 22

Story Info
Gina introduces the girls to Sif.
4.4k words
4.5
8.7k
6

Part 22 of the 32 part series

Updated 04/27/2024
Created 06/20/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Lordoflol
Lordoflol
128 Followers

Gina was with Sif in her office, she was wearing her black suit with skirt and jacket and her hair in a bun like always, Sif was with her long black hair loose but dressed much more daring, she was wearing a long-sleeved turtleneck without a bra with a big hole in the neckline revealing a deep cleavage, with every step her huge tits bounced everywhere, a very short plaid skirt that exposed almost half of her ass, and high heels that made her quite a bit taller than Gina.

"Well Sif, how about I introduce you to the girls you don't know?" Gina asked.

"Perfect." Sif said, "That way I'll also get to know the prison, it's so big that sometimes I get lost."

"Follow me." Gina said.

They reached Lucille's room, she was sitting next to a short man with his tiny cock in a pillory while another man stood waiting over her.

"This is Lucille, she is one of our most creative girls." Gina said smiling, "Hello Lucille."

"Hello girls!" she exclaimed smiling as she got up.

"Hello Lucille, nice to meet you." Sif said.

"You are very tall!" Lucille exclaimed looking up at Sif, Sif was at least a couple of heads taller than her, "I look like a little girl next to you."

Lucille was wearing a short flowing white sundress and was peering through her black glasses at Sif, smiling as if she'd remembered some joke she'd been told.

"Just now I was giving little Petey his semi-annual ruined orgasm, we've been edging for a couple of hours, I think it's time to cum, huh Petey?" she said looking at him smiling.

He nodded quickly, looking into her eyes, he had something inside his mouth.

"Once a month I give him one of my thongs for being such a patient guy, it's usually one that I've been wearing for several days, they're the ones he likes the most, aren't they, my little perv?" she said sitting back down, "That's why he can't talk right now."

"And where are the other boys?" Gina asked.

"Since I got the edging machines I leave them with them all morning, I think my boys have grown quite fond of them." she said laughing while Petey couldn't stop looking at Sif's huge tits.

"It seems he loves my beautiful tits." Sif said smiling.

"Excuse him, he's always horny and frustrated, he hasn't thought clearly for a long time, I think." she said gently stroking his big blue balls as his little cock released a trickle of precum, "Okay, let's lighten these bitches up a bit."

Sif pulled up a chair and sat cross-legged right in front of Petey while Lucille slowly rubbed a finger under his cock. With the short skirt she was wearing, Petey was able to see her beautiful legs and part of her buttocks.

"Your boy looks like he's right on the edge." Sif said smiling watching as his cock throbbed.

"Yeah, he's dying to cum, a few quick jerks and it's over, but I'd rather take it slow and easy." Lucille said.

Then Sif spread her legs showing Petey that she wasn't wearing anything up her skirt, Petey's eyes almost popped out when he saw her full bush and his cock started to throb and bounce.

"Oops, not so fast, little boy." Lucille said laughing, letting go of his cock, "You almost caused an accident, Sif."

"You know what?" Sif said still with her legs spread, "I've decided no orgasms for the boys until Gina leaves, sorry little Petey but you'll have to wait a few more months to empty those big blue balls of yours."

The man was still engrossed looking at Sif's pussy and it took him a while to realize what she was saying, until suddenly he looked into her eyes and began to scream desperately with the thong in his mouth.

"Sorry, little boy, but orders are orders." Lucille said smiling as she got up, "You'll get your chance in a few months."

"Well, we're leaving." Gina said. "It's been a pleasure, Lucille, we'll get to know each other better." Sif said getting up from her chair.

"Of course." Lucille said, "See ya."

"Who's next?" Sif asked as they headed into the next room.

"Cecilia, she has been here for about 2 years." Gina said, "How did you like Lucille?"

"She is a very sweet girl, I think we'll get along very well." Sif said.

"She's a hippie, but don't let that mislead you, she has her boys to the letter." Gina said smiling.

"Perfect." Sif said smiling.

When they entered the room, Cecilia was standing with 4 of her boys surrounding her, sitting on the floor with their legs open, their eyes covered and their hands tied behind their backs, the rest were each in their beds holding their balls. She was only wearing a tiny white bra and a white thong that revealed her huge and toned ass, she had a bottle in her hand. The boys were trembling with fear.

"Hello girls!" she greeted.

"What are you doing?" Gina asked.

"Playing spin the bottle." Cecilia said smiling, "I kick the balls of whoever it is, over and over again until one by one they can't take it anymore, the last one gets 10 points and at the end of the month the one with the most points have a chance to cum."

"How fun!" Sif exclaimed, "Can we look?"

"Of course." Cecilia said, bending down and turning the bottle.

They waited a few seconds until the bottle stopped pointing to one of the boys.

"Ooooh, poor little Gus, you again, bad luck." she said picking up the bottle and giving a tremendous kick to a boy the bottle wasn't pointing at.

Sif and Gina started cracking up.

"Surely unlucky Gus, huh?" said Sif.

"Yes, the poor guy has 3 in a row, but he holds up like a champ, he's the one who hasn't cummed the longest of all my boys and his desperation is stronger than pain, isn't it, little Gus?" Cecilia said smiling as she winked at Sif.

The boy clenched his teeth, trembling without saying a word.

"Do you play this often?" Sif asked.

"Every morning." Cecily said.

"Well, we won't bother you anymore, you seem quite busy, we'll talk later." Sif said, "See ya."

"Of course." Cecilia said, "Bye."

"Next round!" Cecilia exclaimed as Sif and Gina left, "You again Gus? This bottle looks like it's alive."

They went out into the hallway while Cecilia kicked him again.

"The next one is Cammie. She's Charlie's cousin." Gina said reaching a new door.

Cammie was sitting on top of a man's face, one finger slowly stroking his frenulum. She was wearing a red and black checkered sling bikini and a white miniskirt that left her ass completely exposed, she wore a black headband with her hair brushed back and falling to her shoulders.

"Hello girls." she greeted smiling without stopping to rub his cock.

"Hi Cammy." Gina said, "I've come to introduce you to Sif."

"Nice to meet you, Cammie." Sif said.

"Same here. I would shake your hand but mine is a bit sticky." she said smiling.

"Is that Theo?" Gina asked.

"Yes, little Theo and I have grown very fond of each other, now he is my favorite, ahead of that loser Timmy." Cammie said pointing to Timmy who was tied to his bed with his big blue balls covered in bruises.

"I believe you." Gina said pointing to Theo's balls smiling, "In almost two months his balls are more swollen and bluer than his peers."

"Well, my work has cost me to get him in tune." Cammie said, still rubbing her frenulum very slowly.

Then he started to yell and shake and she pulled her hand away from his cock.

"Perfect, that was 10 edges." Cammie said smiling, grabbing his balls with one hand as his cock trembled and throbbed, "Now 50 punches and we're done."

"I remember when I brought him to you 2 months ago, the fool thought he was going to have a bunch of orgasms, look at him now." Gina said laughing, "Okay, let's go see the next girl."

"Yeah sure, bye Cammie." Sif said.

"Bye girls." Cammie said, starting to punch Theo hard in his big blue balls.

"You already know Kayla, Freya's friend, Charlie and Freya of course, we only have left Mia, our newest addition." Gina said reaching Mia's room.

Upon reaching the room, they saw Mia's boys tied to their beds with their eyes looking at a screen in which Mia was doing a striptease while dancing and twerking. She was dressed in a pleated skirt and top, all in black with her blonde hair loose, bouncing her curls to the music.

"Now comes the good stuff, watch out." Mia said turning around and slowly pulling up her skirt revealing a buttplug for half a second and pulling it down again quickly, "Have you seen it? Don't worry, you'll have plenty of chances."

Gina looked towards the boys, they hadn't even realized they were there, their eyes were fixed on the screen while their cocks throbbed and trembled inside their little cages.

"She is not here." Gina said, "Maybe she's in the dining room."

When they got to the dining room they saw Freya sitting drinking a soda looking at the screen of her mobile.

"Have you seen Mia?" Sif asked.

"She's in the infirmary, she went with Charlie to see Samuel." Freya said.

"Well, let's go see them in the infirmary then." Gina said.

"Bye little sister." Sif said.

"Bye bye." Freya said.

When they got to the door of the infirmary they heard some music.

"Wait." Gina said, "Let's go to the mirror room."

Upon arrival, they saw the two girls with Samuel through the window. While Mia danced in front of him, a camera located in front of the bed recorded her and Charlie played with Samuel's cock sitting next to his bed.

Charlie was dressed exactly like Mia in a black top and a very short black skirt.

"These girls are naughty, I love it." Sif said laughing.

"Don't show him too much Mia, you know I don't like my virgin boys seeing naked women." Charlie said continuing to stroke Samuel's dick who was on the edge, "I always censor all the porn in your edging sessions because otherwise, you surely could have a little accident, right, little boy?"

The boy only made small moans as he stared at Mia's ass every time her skirt rode up while she danced.

"Don't worry, I'm just teasing him a little." Mia said smiling, "Anyway, I let my boys see me naked, so in a little while you're going to have to do something if you don't want him to see my beautiful tits." Mia pulled her black top down a bit almost to the point of showing a nipple.

"Or my lovely bubbly ass." She said turning around, raising her skirt a little, revealing her buttocks and a little bit of the buttplug.

"Or maybe my pretty little pussy." She turned around again lifting her skirt and covering her pussy with one hand, only revealing a bit of her pubic hair.

"Woow, relax little boy!" Charlie exclaimed, letting go of his cock, "See why I don't let you see naked women? Just showing you a little bit almost drives you over the edge."

His cock bounced and throbbed with precum as Charlie looked on smiling.

"These two blondies are like two little devils." Sif said laughing again, "You know what I like the most about all your girls?"

"What?" Gina asked.

"That everyone seems to really enjoy doing their job, I love that." Sif said.

"I know, to work here you have to enjoy torturing these little boys, there have been stunning, beautiful girls, but in the two weeks of testing I have seen that they weren't worth it." Gina said, "The appearance is very important, of course, but the enthusiasm when it comes to torturing these boys is even more important."

"I know what we should do." Charlie said, "I'm going to put my ass in front of your face so you don't have to worry about having a little accident watching Mia tease you naked, how about that?"

Charlie got up and got to her knees on top of the bed with her ass inches from his face and then she plopped forward against Samuel's stomach with her face very close to his cock lifting her skirt up and showing him her perfect round ass only covered by a white thong.

"You see?" Charlie said with a mischievous smile beginning to stroke his cock again, "Now you won't have to watch that mean girl try to tease you."

Mia kept dancing to the music until she began to lower her top, completely showing her tits.

"You like it, huh?" she said pinching her nipples.

"You know that Samuel is obsessed with big asses?" Charlie said looking at Mia, "My big round ass is like a dream come true for him, it's a shame he'll never touch it, but I have a little surprise for him."

Charlie slowly pushed her thong aside to reveal her black spade shaped buttplug.

The boy started to gasp for air.

"I knew you would like." Charlie said smiling, playing with his cock again.

Mia kept stripping and dancing and Charlie edged Samuel over and over again while Gina and Sif enjoyed the show.

"Well, we'll talk to Mia later." Gina said, "Although you can already get an idea of ​​what she's like."

"Yes of course." Sif said laughing.

As they went out into the corridor they met Susan.

"Are they done yet?" she asked them.

"I don't think they'll be far from finishing, why?" Gina said.

"More than an hour ago they told me that they were going to talk to Samuel for a second and since then I've been waiting, I have to wash him and put this cream on his balls, they're so swollen and blue that the poor boy must be hurting a lot." Susan said.

"Well, when they go out make sure you put a lot of that cream on him, he's going to need it." Gina said laughing out loud.

After going for a drink Gina and Sif returned to the infirmary, when they opened the door they saw nurse Susan next to Samuel with a tub of soapy water.

"Poor little boy, your balls are a mess." she said softly pouting as she gently rubbed her soapy hands over his cock and his swollen balls, "You must be in a lot of pain."

Samuel couldn't stop looking at her big tits that overflowed over her cleavage with a pair of little keys dangling between them.

"You like them?" she asked with a mischievous smile, "Look at them all you want darling, it's the only thing you can do in your state, isn't it?"

The man's eyes were riveted on her breasts as she undid a button, letting her tits hang out almost completely, covered by her red bra.

"I'm sure you'd rather have your tiny cock rubbed against my big tits, wouldn't you, little boy?" Susan said rubbing one of her fingers in between her tits without stopping rubbing his cock with her other hand, "But no, I'm not like one of those mean girls who have been teasing you, I'm just trying to make you feel better, my poor boy."

"Hello Susan." Gina said.

"Hello girls." Susan said smiling as she continued to rub Samuel's dick gently, "I'm giving Samuel a little washing up."

"I see." Gina said smiling, "Where have the girls gone?"

"They left a while ago, I think they were going to Mia's office." Susan said picking up a wet rag from the tub and rubbing it gently over his cock and balls.

"Ok, so let's go see them." Gina said.

Sif put her face close to Samuel's cock as Susan continued to rub with the cloth and saw a couple of drops of precum drip from his cock.

"Sorry Susan, but it seems like it's leaking, maybe you should start over." Sif said smiling.

"Again?" Susan said grabbing his cock with two fingers and watching him closely, "You're right! Honey if you don't stop dripping we're going to be like this all morning, and I still have to put the cream on your balls."

"Well, we'll let you continue." Sif said.

"Yeah sure, bye girls." Susan said as she slowly rubbed his cock and balls again with her two soapy hands as her big tits bounced, "And you little boy better hold your own or we'll never finish."

Samuel kept looking at her bouncing tits without blinking, it seemed that it was going to be quite a long morning.

They entered Mia's room and saw her boys stil lying on the beds staring at the screen, reached the door of Mia's office and saw that it was open, the two of them were talking when they arrived.

"In the end Marcus and I have broken up, I told him what my plans with Ryan were and he didn't like it at all." Charlie said.

"Well, I already told you that if you were only interested in sex you weren't going to have a problem replacing him." Mia said.

"Yes, now I just need to know how I can get Ryan out of here, that seems the most complicated." Charlie said.

"Didn't you say you'd drop the charges and be done?" Mia said.

"It's not that simple, apparently that won't help, there's enough evidence to know that he was really stalking me." Charlie said.

"Then, what are you going to do?" Mia asked.

"I have no idea." Charlie said.

"Hey girls, I'm sorry but we've been listening to your conversation and I think I have a solution." Sif said entering the room surprising the two girls.

"Sorry girls, we didn't mean to, it's just that the door was open and... well, you know." Gina said.

"No problem." said Charlie, "And what is your solution?"

"Well for starters, is that boy one of your boys?" Sif asked.

"Yeah." Charlie said.

"Good, What are your intentions with him?" Sif asked.

"Well, it's a bit complicated." Charlie said hesitantly, "I'm romantically interested in him, you could say."

"Let me guess, you have an interest in him but with his tiny dick you want to fuck as many giant cocks as you want while he waits for you at home in his chastity belt to eat your pussy when you get back from a night of wild sex, right?" Sif said smiling.

"More or less, yes." Charlie said laughing.

"I think I've seen that before." Sif said laughing.

"Well then, yes, there is a solution." she said, "There is a clause that if the boy has good behavior while in prison and both his guard and the prison council agree, the case can be sent to a judge and if he considers, he will leave on parole in charge of a trustworthy person."

"That would be perfect." Charlie said.

"Wait, there's more." Sif said, "It will be a period of 1 year minimum, with reviews every two weeks in prison."

"No problem." Charlie said excitedly.

"Not so fast." said Sif, "The boy will always be in a special chastity cage owned by the prison, one key will be held by the person in charge and the other by the prison director and during that year he will be completely prohibited from cumming, if he tries to escape, he has an orgasm or is released from the cage without permission, he will immediately return to prison and have a minimum of 5 years added to his sentence."

Charlie's jaw dropped.

"1 year without cumming?" she asked.

"As minimum." said Sif, "Do you think the boy will accept it?"

"I don't know, it seems too long, I'll discuss it with him." Charlie said.

"Later we can go talk to him and I'll explain everything, if you want." Sif said, "Changing the subject, girls, I think you're fantastic."

"What are you talking about?" Mia said.

"The little show you put on in the infirmary, I loved it." Sif said smiling.

"Oh did you see us? Thank you very much, I think we work very well as a team, don't we, Charlie?" Mia said.

"Yes, of course, it's because we've been friends for years, we get along very well, here and in bed." Charlie said winking at Mia.

"That too." Mia said laughing.

"I've seen that you have your boys in chastity, I like that." Sif said.

"Of course." Mia said, "I like knowing that only I have access to their little cocks, not even they can touch it without my permission."

"Would you introduce me?" Sif asked, "The rest of the girls were busy and I didn't get to meet any of their boys in person."

"Yes of course." Mia said getting up, "Come with me."

"I'll go back with my boys, bye girls." Charlie said.

"Bye bye." they said

They got to Gene's bed and stood next to it, the boy looked at them a little fearful.

"This is one of the new ones, isn't it?" Gina said.

"Yeah, this is Gene, the youngest of my boys, he's a very good boy, maybe this month he'll be the lucky one who gets to cum, would you like that, little boy?" Mia said smiling.

The boy looked at Mia without saying anything, scared.

"He's a little scared." Mia said.

"Answer her little boy!" Sif exclaimed grabbing him by the balls with force.

Lordoflol
Lordoflol
128 Followers
12