Small Penis Prison Ch. 08

"Have you been working here a long time?" Ryan asked.

"About 5 years, I started at 20 years old." she said, "And no talking without my permission."

Ryan was silent as he followed her, unable to stop staring at her perfect ass.

"These are going to be your buddies." she said pointing to the boys, who were still lying on the beds sweating, "You'll get to know each other."

The boys looked at him blankly.

"With you I have 4 virgins, you know?" she asked.

"Yes I know." he said sheepishly, "The nurse told me."

"Awww poor thing." she said pouting, "There's nothing to be ashamed of, a lot of guys with small dicks like you, are virgins."

They passed a door and entered Charlie's office.

"Sit down!" she commanded.

He quickly sat down in the chair while she went to a closet and grabbed a towel.

"Let's see..." she said as she took Ryan's file with one hand and wiped the sweat from her forehead with the other with the towel.

"Wow!" she exclaimed, "5 years!" "What did you do?" she asked.

"They caught me looking out the window while I was masturbating." he said tremendously nervous.

"Looking at what?" she asked with a little smile.

"To you." he said looking at the ground.

"You were spying on me!" she exclaimed, "What a pervert!"

"Even so, it seems too little to me to put you here for 5 years." she said, looking at the file, "Are you sure you didn't do anything else?"

"I swear." he said.

"Okay I believe you." she said smiling, "But now you're here and it is what it is."

"I'm seeing that you have a 3 inch cock, amazing." she said with a laugh, "And that you masturbate a lot looking at me." she said raising an eyebrow as she looked into his eyes.

"So you think i'm hot, right?" she said with a mischievous smile as she slowly caressed his cock with her foot under the table.

"I'm going to explain my rules to you." she said as she continued stroking him with her foot, Ryan's cock was harder than a rock. "For starters I'll tell you that I have my boys without a chastity belt, there are girls who prefer them with it but I like to see their tiny cocks erect all day dripping with precum as they sway from one side to the other." and she started laughing.

"Every month we will meet in private and you will have a chance to cum."

"I'll roll a pair of 6-sided dice and if you roll 14 or higher you can cum." she said with a smile, "A 12 or 13 is a ruined orgasm."

"Now I guess you're wondering, how can I get a 13 or a 14 with 2 6-sided dice?" she said looking into his eyes, "Pretty simple, for every inch of your little dick, one point will be added, and thus you can reach more than 12."

"I'll show you!" she said with an amused smile.

She opened a desk drawer and took out 2 dice and threw them on the table. A 5 and a 6 came up. "That would be 11, plus your 3 inches, 14." she said, "What a lucky boy!" she exclaimed.

"Too bad this roll is just a test." she said laughing.

"It's very easy, isn't it?" she asked as she kept rubbing her foot against his cock.

"Yes." Ryan replied.

At that moment there was a knock on the door.

"You may come in!" she said looking at the door. Then the man who had said he was at the edge earlier entered the office.

"Oh, little John!" she said looking at the man, "Come here, I forgot about you!"

The man walked over to her and stood by her side. He was a tall, skinny man in his mid-forties, with graying hair and a tiny dick no larger than 1 inch. What drew attention were his huge balls, Ryan hadn't noticed before but they were abnormally big, bigger than Timmy's but maybe not as blue.

"This is John Amos Forrester III, a wealthy man from the city, he comes from a wealthy family and has had everything in life since he was born." she said pulling a couple of jars out of the drawer, "He was a brilliant businessman and ran the family business successfully."

"What people didn't know is that he forced girls to have sex with him in exchange for hiring them." she said taking a green pill out of one of the jars and popping it into his mouth, "Swallow it!"

"Many girls over the years were forced to fuck him or even suck him off." she said with a disgusted face, "It's a good thing they caught him, otherwise he would continue taking advantage of young girls."

"He's been with me since I started working here." she said smiling, "What a great time we've had, haven't we?"

"Yes Charlie!" he exclaimed nervously.

"6 years together, huh little John?" she said, "How fast time flies!"

"Every day twice a day he comes to my office and I'll give him one of these pills and then this cream." she said, opening the other jar, "I'll give him a little massage for 10 minutes."

"The pills are to increase sexual desire and sperm production." she said putting on a pair of latex gloves, "They're designed for horses but it doesn't matter because little John here is quite the stallion, aren't you?"

"Yes Charlie!" he answered again.

"The cream does something likely, it increases sperm production and makes his balls bigger, like a big strong boy, although it has a couple of small side effects, for example it makes your penis smaller and makes his balls very sensitive, a pat on his balls is like being kicked, they are pretty tender." she said as she gave him a little pat on the balls and he groaned in pain.

"When he came in here his dick was just over 4 inches and now you see it." she said letting out a laugh. She picked up the cream with her gloves and put some on his dick and rubbed it in very gently for a few seconds.

Then she took more cream and began to massage his balls gently.

"Little John hasn't always been this docile, haven't you, little one?" she asked, looking at the man.

"When he came in, he thought he was a macho, that's why we had to calm him down and I sent him with Freya for a week." she said smiling, "He came back a new boy."

"And since then he continues this daily treatment." she said pouring more cream on his balls.

"I don't play the same game with him as with the rest of the boys, he throws a 6-sided dice once a year and depending on what comes out he has a type of ruined orgasm, there are some that are a little more pleasant than others but they are ruined after all." she said rubbing his balls a little harder, the man looked like he was suffering.

"In a week it's his annual dice roll, fingers crossed!" she exclaimed laughing.

"How I like to play with these huge nuts!" she said, groping his balls hard while he suffered in silence.

"Okay, this is it." she said as she took a stick out of the drawer, "Bite!" she said as she put it into his mouth.

The man made a terrified face and began to bite the stick while breathing heavily.

"Don't you dare yell." she said quietly as she took the rubber band out of her hair and put it on her balls, making them look even bigger and veinier. She grabbed his balls with one hand and with the other she began to punch him very hard without rest.

The man was drooling through the stick that he kept biting down hard, he had an expression of extreme pain on his face but he did his best not to scream, only small moans were heard with each punch.

Charlie went on like this for a while until she seemed satisfied.

"Okay, you can go." she said as she removed the hair band from his balls and took off her gloves.

The man took the stick out of his mouth and slowly walked out of the room, it seemed as if each step was a kick in his balls.

"Well, as I was telling you." she said smiling, "If you roll a 14 or higher you will have a real orgasm, 12 or 13 a ruined orgasm and less than 12 denial."

"If it rolls a 12 or 13 then we'll play the same game as little John, we'll roll a 6-sided dice to see what kind of ruined orgasm you get."

"Du yo understand?" she asked.

"Yes." he said, "But I have a question."

"What?" she asked.

"What kinds of ruined orgasms are there?" asked the nervous.

"Very good question." she said with a mischievous smile. "There are more than 6 but these are my 6 favourites, and don't ask me why they are called like that, it's up to Gina." she said.

"If you throw a 1, it will be 'Milking the monkey', it consists of making a circle with your index finger and thumb and just continuously pressing below the frenulum until you reach the edge over and over again, and at the end you go a little over the edge and you release the cock, if it's done right, only a few drops of semen will be released."

"2, it'll be the corkscrew, that's Cammie's favourite, you slowly bring the cock to the edge over and over again until you have it riding the edge for as long as you want massaging the frenulum with your thumb.

Just push a little over the edge, you drop his cock and punch him hard in the balls, same thing, if it's done right only a few drops of cum will be released, Cammie is a master at this."

"A 3 is abandoned, it's the boys' favourite, because with this, a large amount of semen is released, you quickly bring your cock to the edge and just before it cums you release it, very simple."

"A 4 is the queen of ice, you have a bowl of ice water ready, you bring his cock to the edge as much as you want and when you're ready you let it go a little over the edge and you put his cock and balls in the ice when it's cumming."

"A 5 is the drums, you do reps of 5 strokes 5 punches until you get past the edge and ruin the orgasm." she said, "Although it may seem cruel it's one of th boys' favorite because it releases a lot of semen." she laughed.

"Lastly, if you shoot a 6, there is my favorite, the silk stopper, the first thing is that you tie the base of the cock tightly, then you only gently caress the tip the cock, almost without touching it until you take it to the edge repeatedly, at the end he is practically riding the edge all the time until a little breeze blows it over the edge." she said, "Then your cock starts to throb uncontrollably and after a while you untie the base of your cock and watch a little trickle of semen slowly fall from the tip. It's perfect, don't you think?" she said laughing.

"Little John had a 6 last year, you should have seen it, it was so much fun!" she exclaimed with a laugh, "The poor boy only released a tiny droplet."

She kept laughing for a while as if remembering the magical moment.

"I'm going to explain your day to day." she said more seriously, "Every morning when you wake up you all go to the showers, some prefer cold showers, I leave that to your choice, then breakfast." she said, "During the morning you will have 3 hours of edging while you watch your favorite porn, except the virgin ones, I always have special videos for them." she said laughing, "Then it's time for lunch and after that some free time."

"In the afternoon I have my exercises, a bit of stationary cycling, running on the treadmill, squats, etc." she continued, "It's like that for 1 hour, while you masturbate looking at me, that's what you saw when you arrived."

"Then another bit of free time and finally after dinner, before going to bed I will have a little time alone with each one where we will talk and maybe I will take you to the edge a few times." she said with a wink.

"What do you think?" she asked, "It doesn't matter what you think, it is what it is." she said laughing.

"That's the day to day but there are always surprises from time to time." she said with a smile. "If you behave badly or don't obey me you will be punished, and if you do it repeatedly I will send you a week with Freya, you don't want to meet her, believe me."

"And no cumming without my permission, under no circumstance." she said very seriously, "It would entail a severe punishment, understood?"

"Yes." he said nervously.

"Any questions?" she said looking into his eyes.

"Well... I do have a question." he said very nervously, "Before I came with you the nurse Susan said that I was going to be able to cum today, is that true?"

Charlie started laughing out loud.

"What a bitch!" she said to herself, "Yes, don't worry, today I'm going to milk you dry so you can start your sentence with empty balls" and laughed again.

Then they knocked on the door again.

"Who could it be?" Charlie said to herself confused, "I'm not waiting for anyone..."

The door opened and a beautiful blue-eyed girl with blonde curls and olive skin walked in.

"Mia!" Charlie exclaimed, "What are you doing here?"

"Hello Charlie!" she greeted, "Well, my boys won't arrive for another 2 days, so I'll be with you that time, is that okay?" she said with a sad smile.

"Of course." she said getting up from the chair and giving her a hug, "Poor thing..."

"Don't worry, we're going to have a great time these two days!" she said laughing.

"Come with me." Charlie said as she left the office.

Ryan and Mia followed her until they reached another door, they went into a small room, there was a chair with harnesses and a huge screen in front of it.

"Sit here Ryan." Charlie ordered.

Ryan sat down and the two of them tied his hands and feet.

"Now I'll leave the two of you alone while I go take a shower." Charlie said, "Mia will take care of you while I put on your screen one of my special videos."

She turned on the screen and started the video, it showed Charlie looking at the camera in silence.

"Have fun!" she exclaimed smiling as she left.

"Well, we're left alone." Mia said kneeling in front of him, "Don't worry, I know what I'm doing."

"Well, first I'm going to take this off, I don't want to get it dirty" she said with a mischievous smile, pointing to her dress.

She was wearing a tight yellow short dress that enhanced her curves, she was very hot.

She undid it on one side and let it fall to the floor. Underneath she was wearing a shiny purple bikini and thong, they were tiny, covering little more than her nipples, and the thong revealed some of her trimmed pubic hair. Just looking at her almost sends Ryan over the edge. He was rock hard dripping precum non-stop.

"That's better." she said smiling, as she got back on her knees in front of him.

On the screen Charlie was talking to a man in a sensual way.

Then Mia took his balls with one hand and began to massage them while with her other she held his cock, brought her mouth a little closer and spit on the tip. She spread the spit all over his cock and began to rub it very slowly.

Ryan wasn't going to last long before reaching the edge, it was the best feeling he had ever felt in his life.

A man suddenly appeared on the screen, Ryan recognized him, it was Marcus, Charlie's boyfriend. He stood up in front of her and took his cock out of his pants, that cock was huge, the biggest Ryan had ever seen.

Then Charlie got closer to Marcus's dick and suddenly everything was pixelated, from the sounds he could tell that she was sucking it but he couldn't see anything.

"Ah, one of Charlie's videos!" Mia said laughing, "You're a virgin, aren't you?"

"She edits them so virgins like you can't see anything." she said laughing as she rubbed his cock a little faster.

"I am going to cum!" Ryan said gasping for air.

Mia suddenly released her cock.

"It don't think so." she said with a smile.

"So you're Ryan, Charlie's neighbor, right?" she asked as she slowly rubbed his cock again.

"Yeah." he said trying to keep his composure.

"And why are you here?" she asked with a little smile as she rubbed a little faster.

"Because they caught me spying on her while I masturbated." he said, realizing that he had said it out loud, he turned very red.

She started laughing out loud.

On the screen Charlie had stopped sucking Marcus off and now she was starting to undress but every time it looked like he was going to see something she got pixelated.

"Shit!" He exclaimed out loud in frustration.

"Ooohh poor thing..." Mia said pouting, "You wanted to see Charlie naked and those damn pixels won't let you, what a shame." she said rubbing quickly.

Ryan was on the edge and Mia stopped again.

A rush of frustration coursed through his body as he watched his cock bounce up and down dripping a bit of precum.

She continued like this for the entire duration of the video, almost an hour.

At the end of the video, Marcus could be heard pounding Charlie over and over again as she moaned and screamed, her face, which wasn't pixelated, in close-up with an expression of pleasure and rolling her eyes.

"I'm cumming!" Marcus yelled.

"Cum inside me, daddy!" Charlie yelled.

Marcus screamed, he was cumming inside her.

"How good is the video?" asked Mia who was now rubbing Ryan's frenulum.

Ryan couldn't even speak, he'd been pushed to the edge so many times he'd lost count.

"Fine." he said with a suffering face.

"I'm on the edge!" he said warning Mia.

"I know." she said smiling as she began to rub her frenulum very slowly, "Let's hold you there for a while." and winked at him.

Ryan was breathing heavily trying to break free from the bondage.

"Please!" Ryan begged, "I can't take it anymore!"

"And what do you want?" she asked with a mischievous smile.

"Please!" he begged again, "Let me cum!"

"No, no, that can only be allowed by Charlie." she said still holding him on edge, "But if you beg real loud like a good boy maybe I will stop."

"Please! PLEASE!" he begged, "I beg you to stop!"

"I don't know, it sounds a bit fake." she said smiling.

"PLEASEEEEE!" he yelled.

At that moment Charlie walked through the door.

"What's going on here?" she said looking at them seriously.

Mia looked at her as she continued to hold him on edge.

"We are only playing." she said letting out a giggle.

"Let him breathe a little." Charlie said smiling looking at Mia.

Mia released his cock.

"Poor little boy!" Charlie said looking at Ryan's cock bouncing back and forth dripping with precum.

She had showered and changed her clothes, now her blond hair was in two buns. She was wearing a skintight knee-length white lycra bodysuit. It was so tight that you could see her hard nipples and her cameltoe since she wasn't wearing any bra or panties. Just looking at her almost makes him cum.

"Leave me a spot." she said kneeling next to Mia,

"I promised you I was going to let you come so here we go!" she began massaging his balls gently. "They seem filled to the brim." she said, looking into his eyes with a little smile, "Has Mia been bad to you?, bad girl!"

So while with one hand she massaged his balls with the other she caressed his cock very gently.

"Looks like you're on the edge, huh?" she said very sensual.

"Yyyy-Yes!" he exclaimed stammering.

She released his cock and got up.

"What do you like in me the most?" she asked looking into his eyes.

"Your perfect ass." He said breathing heavily.

"Ohhh, this perfect ass?" she said turning around.

Mia couldn't stop laughing.

"Yeah..." Ryan said wide-eyed, it was the best ass he'd ever seen.

Then she began to very gently stroke his cock with her ass.

"You like this?" she asked.

"Yes." He was back on the edge, closer than ever.

Then she pressed her ass against his cock, rubbing it up and down in one quick motion, then pulled away from him.

His cock started to throb, he had gone over the edge and his cock was dancing in the air. Suddenly semen began to drip from the tip of his cock without him feeling the slightest pleasure. A trickle of semen traveled from the tip of his cock to his balls as it continued to throb. It was horrible, he moved his hands as if he were trying to touch his cock but it was impossible. Mia and Charlie burst out laughing.

"The first of many, pervert!" Charlie exclaimed, "Now it's time to dinner."

With her index finger she wiped the semen from his cock.

"Open your mouth." she said looking into his eyes, he opened it and she stuck her finger in him, "Good boy!"