Small Penis Prison Ch. 15

Freya walked through the door and saw her boys sleeping in their beds.

"Wake up you pervs!" she yelled turning on the light.

She was wearing a red leather corset that made her huge tits bulge out, an above-the-thigh black tulle miniskirt, and her favorite black metal-toed boots that went up to her knees.

"You!" She said pointing to Samuel, "Now I have to take you to Charlie, but that doesn't mean we can't have some fun first."

She tied his hands and legs against a cross, leaving him with his legs spread wide and his balls fully exposed. Samuel was shaking with fear, that week had been a nightmare come true, Freya had mistreated his balls and his cock to levels he didn't think possible. His cock was full of whip marks and his balls were swollen, blue, and bruised from the constant abuse.

The rest of Freya's boys were practically speechless, in a constant state of fear and pain.

"Do I still look like a bitch to you?" she asked raising an eyebrow as she kicked him hard in his balls.

Samuel cried out inconsolably.

"Answer to me!" she yelled giving him another kick.

"No no!" he yelled, stuttering in pain.

"Good boy." said Freya, "And does Charlie look like a bitch to you?" she asked giving him another kick.

"No." he said through gritted teeth.

"Okay. Well, let's go with a little punishment so you don't forget and then I'll take you with her." she said picking up a cane.

Then she began to hit him with all her might in the balls with the cane without rest.

Samuel screamed in agony.

After a few minutes she stopped.

"Seems to me you've learned your lesson, haven't you?" she asked smiling.

"Yes." he said with a suffering face.

"One more kick and we'll be good to go." she said giving him a tremendous kick that lifted him several feet.

Samuel was breathless for a few seconds, he was in extreme pain.

"Now go take a shower and then have breakfast, we'll meet at Charlie's." she said going to her office.

When Freya got to Charlie's room she found her dressed as a cheerleader. She was wearing a white and blue sleeveless crop top that covered her neck with a hole in the middle that revealed her cleavage and a blue and white pleated skirt that covered little more than her buttocks. She was wearing two pigtails and had two pompoms in her hands.

"Do you like it?" Charlie asked Freya smiling.

"It seems a bit excessive to me." Freya said seriously.

"Don't be a killjoy, I think little Johnny is going to love it, after all today is his big day." Charlie said.

Charlie's boys started coming in.

"Ok boys, everyone to your beds, except you little John, today is your big day." she said smiling, "Come here."

John walked over to Charlie and sat in a chair.

"One year, time flies." Charlie said smiling as she tied his hands and feet to the chair, "You must be desperate, aren't you little boy?"

John was shaking continuously, his cock throbbing nonstop as droplets of precum dripped from the tip.

"Perfect." Charlie said, "Are you ready to..." "C" "U" "M" "Cum!!!" Charlie yelled, jumping up and down moving her pompoms as her tits bounced and her skirt rose with each jump revealing her white thong.

"Well, first the usual." Charlie said smiling as she picked up the pill and popped it into his mouth, she spat into hi mouth afterwards, "To help you get it all down."

The rest of the boys were already lying on their beds with the virtual reality glasses and jerking off.

Then Samuel came in with Gina.

"Sammy boy!" Charlie exclaimed, "I had forgotten about you."

"I ran into this little guy in the hallway and I made things clear to him, if he insults one of my girls again, the punishment will be much worse." Gina said seriously, "It won't happen again, will it, little boy?"

"No ma'am." Samuel said trembling.

"Good boy, now go back to Charlie." Gina said giving him a spanking on the ass.

"Lie on your bed and put on your glasses, it's your edging session, after the session we'll talk." Charlie said kneeling in front of John.

"What are you doing?" Gina asked intrigued.

"It's little John's annual orgasm!" Charlie exclaimed.

"Oooh, can I see?" Gina asked.

"Of course, Freya you stay too, then we'll talk about Samuel." Charlie said winking at her.

"OK." Freya said.

"Well little Johnny are you ready?" She said picking up the cream and starting to spread it on his balls.

"Y-Yes!" he said stuttering.

Charlie grabbed him tightly by the balls.

"Bite hard." Charlie commanded, jamming the stick between his teeth, "Even if it's your day we can't forget the traditions, can we?"

Then she gave a series of strong punches for a few seconds. John bit down hard on the stick, little moans escaping with each punch. His balls were very swollen and blue.

"They look like they're about to explode." Charlie said massaging his balls with both hands gently, "Let's lighten them up a bit."

"First the dice." She said picking up the 6-sided die, "What number would you like to see, little John?"

"A 3." John said shakily.

"Aaah an abandoned orgasm, good choice, well, I wish you good luck." she said rolling the dice.

The dice fell to the floor and bounced several times until it came to rest on the carpet.

"Let's see..." Charlie said, approaching the dice, "Oops, it landed between two numbers."

The dice had been left standing on the carpet with the 5 and 1 in full view.

"Now what do we do, little John?" she said looking at him thoughtfully.

"What does each number mean?" Gina asked.

"1 is 'milking the monkey' and 5 is 'the drums.'" said Charlie.

"For me it's a 1." Gina said smiling.

"Well, I think it's a 5." Freya said.

Charlie laughed.

"Your opinions don't apply to me, you Gina want a one because you love taking cocks to the limit and you Freya want a 5 because you love ballbusting." said Charlie who was still laughing.

"I know, I'll do the following, a mix of the two, repetitions of 5 pressures on the frenulum and 5 punches in the balls." she said smiling, "What do you think, little boy?" John's cock throbbed.

"Look, your tiny dick just nodded, all right then." the 3 girls began to laugh out loud.

"But..." John started.

"But nothing, don't protest, the boss is the dice, I have nothing to do with it." she said, making a circle with her index finger and thumb and placing it on his cock at the level of the frenulum.

She squeezed 5 times slowly and John was almost on the edge.

"When you're on the edge, warn me, be a good boy." she said letting go of his throbbing cock, "Freya, how about you help me with the punches?"

"Of course." Freya said smiling as she knelt next to Charlie.

Then she gave him 5 strong punches in his huge balls.

John screamed with each punch.

"Tsk, Tsk, Tsk, no yelling, you know I don't like it at all, take the stick, bite down hard." Charlie said, jamming the stick between her teeth again, "I know Freya hits very hard but you have to control yourself, okay?"

"Now my turn." She said smiling, putting her fingers back to the level of his frenulum.

"I'm on the edge." John said trembling when she had given him 4 squeezes.

"So soon?" Charlie asked, "And 5." she said squeezing him one last time.

His cock began to bounce up and down throbbing and releasing precum continuously.

"1 inch of real rage." she said laughing, "Don't even think about cumming, not until I give you permission, now it's your turn Freya."

Freya grabbed him by the balls without waiting and delivered another 5 devastating punches.

They continued like this for about an hour taking him to the edge and punching him in the balls countless times.

"How old are you, little John?" Charlie asked after Freya had delivered her round of punches.

John's face was contorted and tears of pain fell down his cheeks, his jaw ached from biting hard on the stick all this time.

"46." he could be understood badly through the stick.

"You're 21 years older than me." Charlie said smiling, "Well we're going to do 21 more rounds and then you can cum, what do you think?"

"No, please..." he started begging.

"Don't complain perv, Charlie is too good to you boys." Freya said very seriously.

Charlie took the cock again with two fingers smiling and started the process all over again.

John came to the edge all 21 times, gushing precum from the tip and groaning in pain with each punch.

"And now I'll let you come." Charlie said winking at him.

"Wait, I'm 21, we should do 4 more for me." Freya said with a mischievous smile.

"You're right. It wouldn't be fair to little Freya, would it, little boy?" Charlie said smiling.

"Pleaseeeeee!" John pleaded desperately, babbling through the stick.

4 more rounds began.

John couldn't take it anymore, his balls hurt like never before from all the punches and the desperation to cum was unbearable.

"The last round." Charlie said when they finished the third, "Now I'll let you cum, focus."

Charlie made a circle with her index finger and thumb again.

"1" she said, squeezing her fingers at the frenulum, John was already on the edge with that first squeeze.

Charlie waited a few seconds and pressed again.

"2" Another edge.

John was drooling all over the stick and his cock was dripping and throbbing continuously. Charlie waited a few seconds again, giggling.

"3" Another edge, John was on the verge of madness, that was inhuman, "Relax Johnny boy, we're already finishing."

Charlie picked up a pompom and rubbed it gently across his cock, another edge.

"4" she said with a new squeeze, John was breathing hard, his eyes bulging, his cock bouncing up and down.

"And finally...5" in this final squeeze as she squeezed she went up and rubbed the head of his cock until she let go of it.

His cock began to bounce much more violently up and down while he moaned, screaming through the stick, it seemed like he was going to cum.

After a few seconds of gasps and gasps suddenly, a tiny translucent white droplet came out of the tip of his cock and began to slide down to his balls.

"Is that cum?" Charlie asked with a mischievous smile.

"I would say yes." said Freya laughing wickedly.

"It just can't be." Charlie said laughing, "If it's cum, it's the best ruined orgasm I've ever seen, it can't even count as a drop of cum."

John kept pushing and fighting with all his might to get something out of his cock, his cock kept throbbing and bouncing but nothing else was coming out.

Then Charlie very carefully caught the droplet with one finger and looked at it closely.

"I don't know, it could be precum." she said still smiling, "What do you think, Gina?" Gina walked over and studied the droplet.

"That's cum." Gina said smiling.

"Are you sure?" Charlie asked.

"Yeah, it's almost a perfect ruined orgasm." Gina said, John still gasping for breath and his cock throbbing.

"What are you talking about?" asked Freya, "It seems pretty perfect to me."

"A perfect ruined orgasm is when once you ruin the orgasm absolutely nothing comes out of his dick, but it's there, waiting for you to take it out, if you now squeezed his dick from base to tip it would start squirting, but if not, it will continue there for a while bouncing and pulsing with absolutely nothing coming out. It's very complicated to do, I once did one for Roger, he told me it was the most horrible feeling he had ever felt, he felt an enormous impotence pushing and pushing while screaming and moaning but nothing, not a measly droplet came out." Gina said while laughing, "Now it's up to you Chalotte, do you want him to drop something else or not? If you want, you know what to do."

"In other words, if I touch him a little, a little more semen would come out, just by touching him a little." Charlie asked with a mischievous smile looking into John's eyes.

John was looking at her in agony his cock kept bouncing up and down.

"Correct." Gina replied.

"Pleaseeeeee!" John pleaded through the stick.

Then Charlie made a circle with her index finger and thumb, encircling his cock but not touching it and began to move up and down without even touching him.

"Something like that, right?" she said laughing looking at John in the eyes.

"Pleaeeeee." John begged again.

"What? I'm already doing it, if nothing else comes out it's your fault." she said, pretending to be offended as she moved her hand away, "By the way Freya, your turn."

"Oh, that's right, I had forgotten." She took his balls smiling and began punching him repeatedly, each one stronger than the last, going over 5 by far, while droplets of cum splashed everywhere.

John screamed in pain, impotence, anguish, despair, Samuel was right, John was in hell.