Small Penis Prison Ch 25

Charlie wasn't able to sleep, it was close to midnight but she was too nervous to do so. Since she had been told that Ryan would be released to her care, she had become a nervous wreck, not only because of the fact that she was going to live with him in her house for a year but she would have him at her entire disposal too, to tease him all day without letting him cum, was that love? She didn't know it but she was about to have a nervous breakdown and there were still 2 days left.

She decided to call Mia to see if she was awake.

"Hi girl." she said, "Were you sleeping?"

"No, not at all." Mia said, "I'm going home, has something happened?"

"No, no, you know, I couldn't sleep, I'm on edge waiting for the day to arrive." Charlie said half laughing.

"Why don't you come sleep at my house?" Mia said, "I'd go to yours but I have something to do at home."

"Really? It's not too late?" Charlie said.

"Don't worry about that." Mia said, "You might get there before me but my they'll open the door for you."

"Ok, I'll shower and go." Charlie said. In less than half an hour she was ringing at the door of Mia's house.

Morty opened the door completely naked.

"Hello Charlie." he said a little embarrassed.

"Hello Morty, I like your new look." she said laughing.

"Mia's orders, we have to be naked when we're at home." He said as she entered the house.

Charlie was shocked to see another man completely naked.

"Hello, Who are you?" she said confused.

"Hello, I'm Benny, I live here now." he said smiling.

"Benny? Oh my God, Mia has told me about you, it's weird, I've played with your cock for hours but I've never seen your face." she said laughing.

"I know." He said laughing a little, "Our queen will be here in a bit, do you want to have something to drink?"

"Queen? Things have changed quickly around here." she said, laughing, "Okay, bring me a glass of white wine, please."

"Right away." He said.

"What a long day, boys, you wouldn't believe it." Mia said when she got home.

The two boys were waiting for her on their knees at the door completely naked while Charlie waited sitting in the sofa.

"The truth is that I just want to sit down an relax." Mia said.

"But, my queen, you promised us that you would let us cum today." Morty said with a worried look.

"I know, I know, my god, Morty, you're turning into quite a grump." Mia said smiling, "You know what? From now on I'm going to call you grumpy, yeah, I think it suits you perfectly."

Morty lowered his head, looking angry but didn't say anything.

"Has Charlie arrived yet?" Mia asked.

"Yes, I'm here!" she shouted from the living room.

"How are you, dear?" Mia sat down giving her a hug, "Bring me a glass of wine too, please."

"Here you are, my queen." Benny said handing him the glass of wine a few minutes later.

"I don't know what's happening to me." Charlie said with a half smile, "I haven't slept a wink since they told me about Ryan."

"Don't worry, I guess it's normal, you have feelings for him and whether you want it or not, you're going to have to live together for a year." said Mia, "Besides, you're going to live with him for the first time and you don't know what that's like, let me tell you that you shouldn't worry about anything, it's the best."

"What are you talking about?" Charlie said.

"Look at me." Mia said smiling, "I have two good boys at my disposal to do everything I tell them, without question."

"I see." Charlie said, laughing, "I didn't know Benny was living with you guys."

"It started today." Mia said.

"And you'll tell me, What is that about you being a queen now?" Charlie said smiling.

"I have always been it." Mia said laughing.

"I guess you're right, maybe I'm thinking too much about it, in the end being in charge of one small cock will be easier than having several." Charlie said.

"Speaking of little cocks, I promised my boys today that they might cum." Mia said.

"And what do you have in mind?" Charlie asked as the boys looked at them expectantly.

"Okay, let's play a game." Mia said.

She tied them each to a chair and put them back to back.

"Now I'm going to tie some vibrators to your cages. The first one to cum loses. I'll free the other one from his cage and give him a blowjob. Good luck, boys." she said with a mischievous smile.

"Really? You've never sucked me and he can have a chance for you to suck him on the first day?" Morty said angrily.

"Oh, my little grumpy, first, I've already told you to address me as your queen, second, if you want me to give you a blowjob so much you just have to hold on longer than him, it's that easy." she said winking at him.

"Yes, I'm sorry, my queen." he said.

"That's better, now let's start the game!" she exclaimed, clapping her hands a couple of times.

"Although first I'm going to cover your ears so you can't hear the other." Mia said, covering Morty's ears, "That'll be more fun, right?"

Then she tied Morty's vibrator to his cage and turned it on full power, then she went to Benny and freed him from his cage.

"But weren't you going to cover my ears and strap a vibrator to my cage, my queen?" Benny asked with a confused face.

"No, Grumpy has been acting out for a while so I'm going to ruin his orgasm, maybe then he'll learn his lesson, but in his eyes it will seem like fair game." Mia said smiling.

"So you're going to give me a blowjob?" he asked excitedly.

"You wish, that's not going to happen, but Grumpy will think I really gave you a blowjob and that's what matters." Mia said with a laugh, "But look on the bright side, at least I'll give you a handjob."

"You are so mean." Charlie said laughing as she enjoyed the show drinking her glass of wine.

"My queen, I'm about to cum!" Morty exclaimed.

Mia got up and turned off the vibrator.

"You're already on the edge, so soon?" She said, uncovering one of his ears so he could hear her, "You're lucky I turned it off otherwise you would have lost, you better hold on, or would you like me to give Benny one of my amazing blowjobs?"

"Sorry my queen." He said, looking determined, "I'm going to win, I promise."

"That's my Boy." She said winking at him smiling.

Mia turned the vibrator back to full power and Morty jumped a little in surprise.

"Be strong, grumpy, think about the blowjob I'm going to give you, I'm going to suck you dry." She said, licking her lips seductively, looking into his eyes.

Morty groaned loudly, he seemed on the edge again but he gritted his teeth trying to hold on.

Mia returned and got on her knees in front of Benny and began to gently jerk him off.

"Poor grumpy, he has already lost and doesn't know it." She said laughing, "If he asks you, it was an amazing blowjob."

"Yes my Queen." Benny said with his little cock already all hard.

Mia continued to rub Benny's cock up and down as Morty moaned, fighting not to cum.

"I'm going to make myself a little more comfortable." Mia said getting up.

She stood in front of Morty and slowly took off her clothes.

"Oh, I just realized I left my underwear at Cammie's." said Mia already completely naked.

"Have you been to Cammie's house?" Charlie asked, "I didn't know you two got along so well."

"I got to know her better today and it's not like you think." Mia said, "She's a good girl, you should get to know your cousin better, I think she'll surprise you."

"I don't know about that." Charlie said taking another sip from his wine glass.

Mia turned around in front of Morty, leaned over and slowly rubbed her hand over her pussy, ending up putting a finger in her ass, then she turned around and put her finger in Morty's mouth.

"I bet it tastes amazing, doesn't it my little grumpy?" she said with a naughty smile.

Morty looked at her and it became increasingly difficult for him not to cum.

"Come on, I know you can, hold on a little longer, Benny's about to cum." Mia said, sitting on top of one of Morty's legs while she uncovered one of his ears.

"I've been riding the edge since the beginning, I don't know if I'll be able to take it much longer, my queen." he said trembling.

"I'm sure you can, let me tell you that I'm getting all wet watching you hold on like a real macho." She whispered in his ear and then gently bit his ear.

"Thanks my queen." he said stuttering.

Mia covered his ear and knelt in front of Benny again.

"I don't know about you, but I'm having a great time with all this, it's hilarious." she said laughing.

"At what point did you become such a cruel bitch?" Charlie said laughing.

"I always have been, I just didn't know it yet." Mia said laughing as she continued rubbing Benny's cock.

After a few minutes Benny was about to cum.

"My queen, I am on the edge!" he exclaimed.

"Wait a second." she said, "Charlie, can you get me a couple of glasses from the kitchen?"

Charlie returned a few minutes later with the glasses.

"This is an idea from a friend." She said with a wink and went back to jerking off Benny. In less than a minute he was back on the edge.

"My queen, I'm going to cum!" he exclaimed.

"Cum for me, my good little boy." She said smiling as Benny began to have spasms and ejaculated forcefully into the glass Mia was holding, "That's it, good boy."

Soon he had finished cumming and was left sitting in the chair with a face of absolute pleasure.

"My queen, I can't hold it anymore!" Morty yelled.

Mia quickly got up and sat on top of Morty again.

"Can't you take it anymore?" she said, uncovering his ear.

"No, please tell me Benny has already cum, I'm at my limit." He said, fighting with all his might not to cum.

"Sorry, my little grumpy, Benny hasn't cum yet, hold on a little longer, come on." She said, gently caressing the inside of his thigh, brushing his balls a little with her hand as if by accident.

"I can't, I can't, I'm cumming!" he shouted.

Mia quickly turned off the vibrator and watched, smiling, as Morty's cock throbbed and bounced up and down inside its tight cage.

"I stopped it so you don't cum, I know it's cheating but it will be our little secret." She said smiling, looking into his eyes.

He watched her through gritted teeth as his cock continued to throb.

"Your balls really look like they're about to burst." She said, grabbing his balls and massaging them gently while he whimpered.

A few seconds later, white droplets began to fall from the hole in his cage.

"Ooooh noooo, is that cum?" She said, releasing his balls and putting her hand to her mouth in surprise while Charlie began to laugh histerically, "Yes, it's cum, poor grumpy, you've lost, I'm so sorry, and on top of that I've ruined it, forgive me grumpy, I didn't know you were so close."

Morty looked like he was about to cry while Mia took the other glass and put it under the cage so the drops fall inside.

"Hey, this morning I promised you that I would let you cum today and I did, what do you say to that?" Mia said.

"Thanks my queen." he said on the verge of crying.

"That's my good boy." she said, "Now wait here while I give Benny his well deserved blowjob, that boy is going to have the best orgasm of his life." Mia covered his ears again and picked up the glass of Benny's cum again while laughing.

"I'm going to wait a little bit, let his imagination run wild for a while, I'm sure he has dreamed of me giving him a blowjob one day, after all he has seen me do them a thousand times and he knows that I am a true artist." She said to Charlie letting out a laugh.

"It seems to me that you are enjoying all this too much." Charlie said still laughing.

"Of course, besides Morty has been acting horrible lately, he deserves it, believe me." Mia said.

Mia used the time to lock Benny back into her chastity belt.

A few minutes later Mia thought that was enough and returned to Morty with the two glasses

"Now swallow it all, it's your punishment for losing, I'm sorry, grumpy." She said pouting.

"Yes my Queen." Benny said while Mia untied them.

"For now you will share the guest bed and I will take the big bed, I think that will be best."

"But..." Morty began until he thought better of it and bowed his head, "It's okay, my queen."

"Good boy, grumpy." Mia said, "Now to bed."

Mia and Charlie stayed in the living room chatting for a while before going to sleep, Mia told her everything about her dinner at Cammie's house.

"The thing about Fluffy is blowing my mind." Charlie said getting into bed with Mia, "What a story."

"I know, I freaked out too." Mia said laughing.

When they woke up in the morning Mia called her boys to bring them breakfast in bed.

"See? You worry too much, this is going to be your life when Ryan is living in your house, it's all advantages." Mia said smiling as they ate breakfast.

"You're right, I don't know why I've thought about it so much." she said, "I'm still a little nervous though."

"It's normal, but don't worry, you'll see how everything turns out great." Mia said.

When they arrived at the SPP Gina was waiting for them.

"Charlie, Olivia is waiting for you in her office." Gina said.

"Ok, I'm on my way." she said.

When she arrived at her office she saw Olivia sitting reading some documents.

"Good morning Olivia, did you want to see me?" Charlie said.

"Good morning dear, yes, please sit down." she said.

Charlie sat and waited while Olivia continued reading for a few seconds.

"Okay, tomorrow is the big day, are you ready?" Olivia said as she looked up.

"Yes, I'm a little nervous, I'm not going to lie to you, but I'm prepared." Charlie said smiling.

"You have nothing to worry about dear, if you trust that boy everything will go smoothly, although let me tell you that if at any time you think you don't want to continue, for whatever reason, let us know and we will lock him back here." Olivia said very seriously.

"I don't think it's necessary, he'll behave very well, I'm sure." Charlie said.

"Perfect, I trust you." She said, "Are you clear on how this is all going to work?"

"I think so." Charlie said.

"It's very simple, he is going to live with you, you will be the one who decides how you are going to live together, you can free him from his cage whenever you want but no cumming for a year, this has to be very clear, any accident and the boy will be severely punished." Olivia said.

"I know." Charlie said.

"Every two weeks he will have to come here for a check-up." Olivia said, "I guess Sif will be the one to handle it, I don't know."

"Okay." Charlie said.

"For a couple of days you're going to be a little busy with all this so Sif will take care of your boys, don't worry." said Olivia, "First thing tomorrow morning you will come here and take the boy home, you can say that you have the day free to explain to him what his life will be like in your house." she said.

Suddenly someone knocked on the door.

"You can come in." Olivia said.

Sif opened the door and entered the office followed by Ryan, he seemed quite nervous.

"Hello girls." she said smiling.

Sif wore her long hair down, she was dressed stunningly as always, with a very tight black tube dress that could barely contain her huge tits, leaving her with a great cleavage, a small black jacket and very high black heels.

"Hello Sif, I was telling Charlie that during these two days you are going to take care of his boys." Olivia said.

"Yes, don't worry about anything, it will be a pleasure." she said.

"Well Ryan, are you ready for tomorrow?" Olivia said looking seriously at Ryan.

"I think so, ma'am." He said, still standing next to Charlie with his hands behind his back.

Olivia stood up and stood next to him.

"Ryan, there's one thing you prisoners always forget." She said, grabbing his balls tightly, "Once you come in here you belong to us, we own your body, your little cocks and your balls, and of course your orgasms." she said, squeezing his balls more and more,

"Once you go live with Charlotte that will stay the same, don't forget it."

"Yes ma'am." Ryan said with a pained face.

"Perfect, let's go get your new cage." She said, sitting back down in her chair, "Come here." Ryan stood next to him.

"For your little 3 inch cock we have several models, all with sensors installed, so we'll know if you try anything stupid, and of course GPS in case the thought of escaping ever crosses your mind." Olivia said taking out several cages.

There were 4 models, 1 looked quite large, another was little bigger than a thimble, another completely flat and the last one inverted.

"Which one would you like, dear?" Olivia said looking into his eyes smiling.

Ryan looked at her doubtfully.

"This one." he said pointing to the largest one.

"Good choice." She said, taking it and putting it on, she did it quickly, it was obvious that woman had put cages millions of times.

"So?" She said raising an eyebrow still smiling.

"It's fine." He said.

The cage still left more than an inch of free space in case he got an erection.

"With this one your little cock can get hard without it hurting." She said, "What do you think, Charlie?"

"I don't know, what do you say?" Charlie said, surprised that Ryan was allowed to choose.

"I don't think so, I'm sorry little boy, but this model is for guys with dicks a lot bigger than yours." She said, taking the cage off him again, "We can't let you go hard all day without a problem."

Then she grabbed the one that was the size of a thimble and put it on quickly, squeezing his cock.

"How about this one?" she said looking at him again.

"It squeezes me quite a bit." He said with a pained expression.

"That means it's working." She said, "What do you think Charlie?"

"I think that one is perfect." she said smiling.

"Are you sure?" Olivia said, "We can try the other two if you want."

"No need, that one will work great." Charlie said.

"Very good." Olivia said, "Now please leave me alone with the boy."

"Yes, come with me." Sif said to Charlie.

They left the office and went to the rest of Charlie's boys.

"You seem a little nervous about all this." Sif said.

"The truth is that I'm getting on much better now, until yesterday I was a nervous wreck." Charlie said with a smile.

"Why? I'm sure the boy is a lot more nervous than you, he'll do whatever you tell him, you shouldn't worry at all." Sif said when they were already arriving.

"I know." she said.

When they arrived the boys had just come from breakfast and were waiting for Charlie.

"John, come to my office." Charlie said.

John was staring at Sif's huge, swaying tits that bounced with every step she took while his tiny cock was already completely hard.

"Close the door and come here." Charlie said as she sat down.

"You see Sif, since you are going to take care of my boys for these two days I have some things to tell you."

"What I can see is that you still have your boys free." Sif said with a half smile.

"Yes, I know, I know you ordered everyone to wear one but I haven't done it yet, I'm sorry." Charlie said.

"Well, that's okay, but by the time Gina is gone I hope all your boys are already locked in a chastity belt." Sif said.

"Yes do not worry." Charlie said.

"Perfect." Sif said with a satisfied smile.

"As I was saying, this is little John, he has an special treatment, 3 times a day I give him one of these pills and I put this cream on his tiny cock." said Charlie, "Thanks to this he has become a really good boy, when he came in his cock was over 4 inches but look at it now, how cute it is, it looks like a little button."

"Are you making his cock smaller?" Sif said with a laugh.

"Yes, and he's much happier with his tiny cock now, aren't you, little boy?" Charlie said smiling as he looked John in the eyes.

"Yes, Charlie." He said, almost letting out a little tear.