Small Penis Prison Ch. 18

Charlie waited in her office thinking about the whole situation with Ryan, she didn't know what was going on in his head.

"Ryan, come to my office!" she yelled.

A few seconds later, Ryan appeared in his office. After the edging session, his cock was throbbing and dripping, although what was striking were his huge blue balls, covered in bruises after a week with Freya.

"Close the door and sit down." she commanded, "Tell me, how was this week with Freya? Have you learned your lesson?"

He looked into her eyes with a blank look.

"Awful, although I suppose you already know that." he said very seriously.

"Well if you behaved like a good boy these things wouldn't happen to you." she said,

"Besides, this is for your own good, believe me."

"Ok, whatever..." He said.

"That's enough!" she yelled angrily, "Come right here!"

Ryan got up and walked over her trembling and Charlie grabbed his balls hard with one hand.

"I've had enough of your behavior, now we're both going to talk seriously, for every time I think you're lying I'll punch you on the balls." she said squeezing his balls as she stared into his eyes, "Got it, little boy?"

"Y-yes." Ryan said stammeringly.

"Okay. Let's begin." she said, still looking into his eyes, "Is it true that you are in love with me?"

"Yes." He said.

"Would you be willing to have a relationship with me on my terms?" Charlie asked.

"Yes." Ryan said seriously.

"Now tell me, do you like it when I play with your tiny dick?" she asked mischievously.

"Yes." he said trembling again, his cock still dripping and rock hard.

"Do you like it when I tell you that your dick is tiny?" she asked still smiling.

"No." he said.

Charlie punched him hard in the balls, that made Ryan groan in pain.

"No lies!" she yelled.

"I like it." he said quickly.

"Very good." she said, "Does your little cock throb when you imagine me fucking a big black cock?" she asked smiling again.

"Yes." he said blushing.

"Well, actually I think you would make a very good cuckold, Ryan." she said slapping him lightly on the balls, "We'll see how we figure this out, for now you're going to be here with me for a while, what do you think, little boy?"

"But..." as he was speaking Charlie punched him again hard.

"What?" she asked very seriously.

"What do you mean I'm going to be here with you?" he asked concerned, "And what do you mean by cuckold?"

"Well, first we have to think about what kind of relationship we're going to have, plus there's still the matter of Marcus." she said smiling, "And as for the cuckold thing, I think you already know that I like big cocks and, I'm sorry to break it to you little boy, but you don't have one, we'll talk about that later." "

"And what are we going to do in the meantime?" Ryan asked.

"What are you talking about?" she asked laughing, "You will remain locked up here with me until I decide, don't worry, it won't be long, but first I have to collect my thoughts, now go, it will be time to eat shortly." Charlie gave his balls a couple of small pats before releasing them.

Ryan left the room while Charlie looked at him eager to tell Mia everything.

She quickly went to Mia's room. Upon arrival she saw a new boy in one of the beds, he seemed exhausted.

"Who's your new boy?" she asked closing the door to Mia's office.

"It's Benny, you know him, the one who was locked in the cell." she said with a naughty smile, "I've kept it for myself."

"What?" Charlie said laughing, "How? Why?"

"Well, Gina told me that she had to go see Benny this morning, I asked her if I could go instead and she agreed and when I met him, he left me dazzled, he's gorgeous." she said smiling, "Besides, he told me he's innocent, I think he's telling the truth, you know me, I'm just an innocent girl."

"And do you think it's safe? He's already tried to escape several times." Charlie said. "Yes, do not worry." Mia said winking at her, "I have him wrapped around my finger."

"And in the end who managed to win your little contest?" Charlie asked.

"Nobody, in the end I let Benny cum, you should have seen what amount of cum." Mia said laughing. "I can't stop laughing remembering Kevin's face knowing he wasn't going to cum, what a loser."

"I've talked to Ryan." Charlie said thoughtfully.

"And what have you decided?" asked Mia interested.

"I haven't figured out how yet, but I want to start a relationship with him." Charlie said smiling, "The truth is that I do feel something for him, with Marcus it's just sex, so I thought I could have both things at the same time, what do you think?"

"Sounds great to me, if that's what you really want, go ahead, and he wants the same?" Mia asked.

"He's a cuckold with a tiny dick, what do you think? He's delighted with the idea." Charlie said laughing, "Honestly, just thinking about controlling his orgasms, having him 24/7 in chastity and playing with his tiny dick, I'm getting wet."

"That's normal, you know what?" Mia said smiling, "As much as I love a big black cock there's nothing that turns me on more than watching Morty suffer as his cock bounces up and down while he begs for me to let him cum."

"The problem is Marcus." Charlie said seriously, "I don't know how he's going to take it."

"Look girl, if it's just sex with him, don't worry, if he takes it badly, you have a line of men waiting for you." Mia said smiling, "Hey, let's meet for dinner today and keep talking?"

"I can't, I have a date with Gina, she's been wanting me to join her business as a keyholder for months and finally I told her that I would go today." she said.

"How cool!" Mia exclaimed.

"Okay, I'm leaving." Charlie said going to the door, "Bye girl."

"See you soon." Mia said.

Gina had told her to wear comfortable clothes, nothing too fancy, so Charlie had decided to wear red leggings and a red tank top. She rang the doorbell and a few seconds later Gina opened, she was wearing a very short white cardigan that showed the underboob of her big tits without a bra and black jeans that accentuated her big round ass with her black hair tied up in a bun as always.

"Fuck Gina, you look great!" Charlie exclaimed. "The bare minimum to tease those losers." Gina said smiling, "Come in."

"Roger, come say hi to Charlie!" Gina yelled, "Do you want a drink? A glass of wine, maybe?"

"OK." Charlie said. "Bring two glasses of wine!" she said.

A few seconds later, Roger appeared with two glasses of white wine, he was completely naked except for his chastity cage. Despite a little over a month having passed, his blue balls were still swollen and bruised from Freya's kicks.

"Hello Charlie." Roger greeted, handing them the wine glasses.

"Hello Roger." Charlie greeted, "How are your balls?"

"Well, they still hurt a little, the doctor said that I had to rest for a few months, it's hard but I'm taking it." Roger said.

"Well, you'll see how fast it goes and then I'll let you drain those huge balls of yours, don't worry." Gina said grabbing his balls and caressing them gently while with the other hand she took a sip from her glass of wine.

"Thanks my queen." he said smiling enthralled.

He started to wince as his cock tried to get hard inside the cage. Then someone knocked on the door.

"Oh, your cuckysitter is here." Gina said going to open the door.

"But my queen, please, I don't need a babysitter, I'm a grown man." Roger pleaded.

"Since when are you a man, little boy? And she's a cuckysitter not a babysitter." she said laughing, "Last year I went out on a date and when I came back I caught him playing with a vibrator on his cage, since then whenever I go out someone comes to watch him, I found an app that takes care of everything, it's called Cuckysitter, it's super cheap with just a little money a month you have someone to keep your hubby in line while you're gone." she said looking at Charlie.

"That's cool!" Charlie said smiling amused.

"That's how we met Sarah, she's the best." Gina said opening the door, "Hello, Sarah!"

Sarah was a petite, blonde, slim, and busty girl in her early twenties, with her curly hair down to her shoulders, dressed in jean shorts, a tight pink T-shirt with a large v-shaped cleavage that revealed her big tits, and flip-flops, she had a big beaming smile on her pretty face.

"Hello Gina!" greeted Sarah with her big smile, "How's little Roger?"

"Well, you know that whenever you come he gets very excited." Gina said, "Isn't that right, Roger?"

"Yes my Queen." said Roger looking at the ground a little blushing.

"I'm glad to see you too, Roger." she said approaching him, "We'll have so much fun together."

"Take the keys." Gina said handing the keys to Sarah.

"Do you want me to give him a bath and massage his balls like always?" Sarah asked caressing his balls while pouting and looking into Roger's eyes, "They seem to hurt a lot, don't they?"

"If it can be, today I want you to remove his cage, clean his little cock and balls thoroughly and then shave him, I want him to be smooth down there." Gina said smiling, "Rub his little cock thoroughly to keep the blood pumping, after so long without leaving his cage he needs to stretch a bit."

"No problem, anything else?" Sara said, continuing to massage Roger's balls.

"Yeah, no cumming, of course." Gina said still smiling.

"Of course." Sarah said, "By the way, may I have my boyfriend over for dinner later?"

"Yeah sure, put Roger to bed early and the house is all yours until I get back." Gina said, "Have fun."

"That's for sure." Sarah said winking at Gina, "Okay little Roger, let's go take a bath, I brought my bikini to get in the tub with you while I leave that little cock of yours clean as a whistle." Sarah said grabbing Roger by the balls and leading him towards the bathroom, "Have fun girls!"

"Bye Sarah!" Gina said, "You better be a good boy, Roger!"

"Now let's go!" Gina said to Charlie walking out the door.

"I only attend to my clients in my office, as I have already told you, you can earn a lot of money with this." Gina said while driving her red Porsche Carrera, "Today I'm going to show you a bit about my business to see if you're interested, we have so many clients that we can't handle it, that's why I need someone else and I think you would be perfect."

"But what exactly does your job consist of?" Charlie asked.

"I'm a keyholder, I charge them 1000 dollars a month to keep the keys to their chastity belts and every time they want an appointment for an orgasm request it's 500 per request, plus 100 dollars an hour if they want a session beforehand." Gina said pulling a key chain with a bunch of keys from her bag, "Look, these are all the keys I have."

"Fuck, there you have more than 30 keys." Charlie said laughing.

"Yeah, I've been at this for quite some time." Gina said smiling, "Today's boy is special, he is a rich heir in his 50s, his father was almost 80 years old when he started a relationship with a sugarbaby 6 years ago, she was a gold digger, she seduced his father and ended up forcing him to marry her after 2 years having him locked up in chastity, on their wedding night he died of a heart attack when she was giving him a handjob as a reward for having left everything to her as an inheritance."

"Oh my god!" Charlie said with her mouth open.

"That's not all, the father stated in the inheritance that she would take care of her son and that he would never lack for anything, so from the moment he died, she put him in a chastity belt and started to treat him as his slave." she said, "4 years ago she contacted me and told me the whole story, she told me that she was bored with him and that she would pay me for my services."

"And she pays you for everything?" Charlie asked.

"No, just for keeping his key, she lets him live in a small apartment and gives him a small payment every month and with what he saves he pays for his orgasms requests." Gina said smiling, "That's not the worst of all, to decide if a client cums or not I have a point system, in the end the result will tell me if I deny the guy an orgasm, if it's a ruined orgasm or a real orgasm, but what makes him special is that every time he has a request before the final decision I have to call his stepmommy and she would add or subtrack some points, I'll just tell you that she's usually quite a bitch." she said letting out a laugh.

Gina kept telling her how the business worked until they arrived.

The place was quite modest, a dark-haired girl under 20 with glasses was sitting at the reception, she was chewing gum while talking on the phone.

"Oops, I'll call you later, my boss has arrived." She said quickly hanging up the phone.

"Hello Nika." Gina said.

"Hello Gina." she said, getting up from her chair, "Mr. Littledale is waiting for you in office 2."

"Nika, I told you not to call him that, it's Mr. Littledick." said Gina, "And why is he in office 2? Has Polly come?"

"It's just that I feel weird calling him that, he's an old man, and yes, Polly is in office 1." Nika said.

"I didn't know she had a client today." Gina said looking at Charlie, "Polly is my partner, we run this together, I'll introduce her to you later."

"I'm going to take you to Mr. Littledick." Nika said giving emphasis when pronouncing the last name.

Charlie noticed Nika, she had her hair in a ponytail, she had a very good figure, her ass was not very big but you could tell she was working out, it was quite toned, she was wearing a short tight black skirt, an open white shirt that showed a lot cleavage, she didn't have very big tits but they looked firm, black stockings and black high heels. As they passed through the door of office 1 they heard what sounded like the voice of a man moaning.

"She's definitely with a client." Gina said laughing.

"Hello Mr. Littledick, here is Gina." said Nika entering office 1.

Walking in Charlie saw a man in his 50s naked except for his chastity belt, sniffing deeply a white thong with little pink hearts, he looked pretty desperate and pathetic.

"What a pervert, Littledick." Gina said, "And whose thong is that?"

"It's mine, I just sold it to him for 100 bucks." Nika said making a bubble with the gum.

"Well, you can leave us Nika." Gina said.

"Goodbye Littledick." Nika said, blowing him a kiss.

"Lie down on the bed, Littledick." Gina ordered.

He couldn't stop looking at Gina's big tits, which swayed under her cardigan, every time she moved they were about to pop out and show her nipples.

Between Gina and Charlie they tied him to the bed hand and foot, it was a special bed, similar to the gynecologist's. They lifted him up until he was sitting with his legs spread, they continued to bind him around his legs and arms and then his chest and stomach until he was completely immobilized.

"Very good, Littledick." Gina said, "What have you come for?"

"Well, I've come to make an orgasm request." he said trembling.

"Oh yeah?" Gina said, "And do you think you deserve it?"

"Yes, I really need it, please." he pleaded still shaking.

"Well, let's go through your file and we'll see." Gina said smiling.

"I brought 100 more bucks for a one hour session, I hope that today I can finally cum." he said with a nervous smile, "The were 200 but Nika teased me so much with her thong that I couldn't resist, sorry Miss Gina." he said blushing.

"There's nothing to be ashamed of, everyone here knows you're a pervert." Gina said, "Give me her thong, please." Gina ordered.

Gina took it from his hand and put it on his head leaving the part where Nika's pussy had been right up against Littledick's nose.

"There you go! Now you can enjoy Nika's scent for the entire session" Gina said smiling, "What do you say?"

"Thank you Miss Gina." he said, sniffing deeply Nika's pussy scent still completely focused on Gina's tits.

"I know you love them, you've always being obsessed with them, like most little dick losers that come here." Gina said sensually, rubbing her tits gently and pinching one of her nipples over the cardigan, "Maybe one day, if you're very, very lucky and a very, very good boy, I'll let you see them."

"Yes please!" he exclaimed with wide eyes still looking at her breasts.

"But not today." She said going for her laptop and sitting next to him leaving the laptop on a table, "Oops, how forgetful I am, I haven't introduced you to my friend, this is Miss Charlotte, she will be with us during the session."

"Nice to meet you, Miss Charlotte." he said very politely still with a pretty desperate tone.

"Nice to meet you, Littledick." Charlie said smiling.

"Well, we're going to leave you alone for a moment, be good" Gina said going towards the door, Charlie followed her.

"Let's go pay Polly a visit." Gina said.

"So you don't let them see you naked." Charlie asked.

"Not at all, at most sometimes I show them a little bit of one areola or some bush, just to torture them a little, nothing more." Gina said with a laugh, "You'd be surprised how horny these losers get with a little pubic hair."

"I thought maybe you'd have a special client, like you told Littledick that you'd show him your tits one day." Charlie said.

"Look at it this way, I hardly ever let Roger see me naked, these losers weren't going to be any better." Gina said, "These girls are only for real men." Gina lifted her cardigan showing Charlie her big tits, Charlie had been always surprised by how beautiful her tits were, they were perfect, they were huge but it seemed that gravity didn't affect them at all, they bounced up and down with each step in a hypnotic way.

"Girl, your tits are a work of art!" Charlie exclaimed, "So what you told Littledick was a lie."

"Well, I like to leave him with a little hope, who knows, maybe one day I'll change my mind and let him see them, although I'm not counting on it." Gina said with a laugh, lowering her cardigan again.

They stopped in front of office 1 and Gina knocked on the door.

"May we come in?" she asked.

"Of course." a girl was heard from the other side.

Upon entering Charlie saw a girl in her early twenties sitting on a chair across from a very fat man in his 30s tied to a chair similar to the one in the other room.

"Hello girls, how are you?" she asked getting up, "I'm here with Mr. Morton, say hi to the girls."

"Hello." he said with difficulty, his little cock throbbing as he dripped with precum, looking exhausted.

Polly wore a pair of very long blonde braids that reached below her waist, she had a body similar to Gina's, big tits and a great round bubble butt, although she was quite muscular, she wore a very tight green leotard that made her big tits stick out the sides, the back ended in a thong which exposed her toned buttocks, her legs were bare, she was wearing red gloves, a red beret and red high boots.

"You're dressed as Cammy!" Charlie exclaimed.

"Yeah!" she said smiling, "Do you like street fighter? I was at a costume party when this loser told me that he needed an urgent appointment, that he couldn't take it anymore, I charged him triple for the inconvenience, right Mr. Morton?" she said smiling, "You must be Charlie, right? My aunty has told me a lot about you."

"Is she your niece?" Charlie said puzzled looking at Gina.

"Yes, she is the daughter of my older sister, Molly." Gina said.

Charlie noticed that they did look alike although Polly had blonde hair and blue eyes and was much taller than Gina, she was just over 6 feet tall.

"Yes, you two look alike now that I realize it." Charlie said.

"You wish you had this ass." Polly said, turning around and smacking her round, muscled ass hard.

"You know that going to the gym bores me." Gina said sticking her tongue out at her.

"She looks more like your little sister than your niece." Charlie said smiling.