Small Penis Prison Ch. 19

"Polly said something about weekly chastity photos, what's that?" Charlie asked on the way to the other office.

"Yes, the weekly chastity check pics, once a week we send a message to the guys, at any time, they have to send us a picture of their cock in the cage in less than 1 minute, I also do it with Mr Littledick but with him there are 3 photos a week." Gina said laughing, "It's a way to make sure they don't take it off, when they come for an appointment we would find out if they had taken it off, with special locks, they're also practically unbreakable, but we don't want any surprises."

"And if you catch them at a difficult moment and they can't send you a photo?" Charlie asked.

"That's their problem, if that happens, Polly punishes them by denying them their orgasm in the next 4 orgasm requests, I'm more benevolent, I only take 10 points." Gina said, "I'll show you the whole point system later."

They arrived at the office and Mr. Littledick was still in the same position, tied to the gynecologist's bed, with his legs open and sniffing Nika's thong like his life depended on it, his cock was trying to get hard inside its cage., Charlie noticed that he had huge blue balls, they had nothing to envy to those of the SPP boys.

"Did you miss us, Littledick?" Gina asked.

"Yes, Miss Gina." he said.

"Well, let's free that frustrated little cock of yours, we still have an hour to play with it." Gina said smiling.

Gina sat between his legs and took one of the keys from his key chain, as soon as she unlocked the cage his little cock got rock hard, almost 1 and a half inches long.

"Look who woke up, it's Littledick's little dick." Gina exclaimed laughing out loud, "This is going to be a looooong hour, I hope you enjoy it." Gina said with a naughty smile.

"It truly is one of the smallest dicks I've ever seen, if you can call that a dick." Charlie said laughing.

"Don't be mean to Littledick, he doesn't have such a small dick, you're just used to real men's big, veiny, thick, fat, black cocks." Gina said with a naughty smile, wiggling Littledick's small cock with two fingers from side to side, "It's true that out of all my clients he's one of the smallest, if not the smallest, but he makes up for it by being the nicest of them all, right my little good boy?"

"Maybe you're right, but it's still one of the most pathetic dicks I've ever seen." Charlie said as she and Gina burst out laughing.

"Let's take him to the edge 1 time each, what do you think, Miss Charlotte?" Gina asked looking at Charlie, "Not that he has much stamina though, you've always been a premature loser but since you haven't come in so long, yours is an exceptional case, isn't it, Littledick?"

"Yes, Miss Gina, I'm so sorry." said Littledick trembling.

"Ohhh, there's nothing to forgive, most small dicks like yours are premature." Gina said smiling at him and winking. "You know, as soon as you get to the edge you have to say our magic word, 'stumblebum', as always, okay Littledick?" Gina said looking into his eyes still smiling.

"Y-yes." he said stuttering.

"First let me get comfortable." Gina got up, turned around and began to slowly lower her pants revealing little by little her big round buttocks with a black lace thong until she lowered her pants with her hands to her ankles revealing her beautiful big ass in all its glory. His little cock began to throb frantically and precum fell from the tip like a waterfall, his eyes were fixed on Gina's ass as he continued to sniff vigorously at Nika's thong.

"Although I know my tits are your favourites, my ass takes your breath away too, doesn't it Littledick?" Gina said sitting down again looking into his eyes still with the naughty smile.

"Y-yes, Miss Gina." he said stuttering again.

"Okay, let's get started." Gina said.

She scooped up some oil and squirted it onto his cock, then grabbed his cock with two fingers and slowly moved up and down for a few seconds.

"Stumblebum!" he exclaimed trembling, Gina quickly released his cock.

"What did I tell you, Miss Charlotte? He has absolutely no stamina." Gina said standing up looking at Charlie smiling, "Your turn."

His cock continued to throb and bounce for a few seconds, Charlie waited for his cock to calm down a bit.

"Now I'd better make myself comfortable, too." Charlie said winking at him.

"Be strong Littledick, this is the best ass you'll ever see in your pathetic life." Gina whispered in his ear, "You're going to understand the true meaning of pawg."

Charlie turned around and slowly began to lower her red leggings until she was reaching with her hands to her ankles fully baring her perfect round buttocks in her white thong that had a black spade symbol with a Q in the center.

"Stumblebum!" he exclaimed quickly.

"Already, Littledick?" Gina said smiling, "Do you know what that symbol means, Littledick?"

"Yes." he said breathing heavily through the thong fighting not to cum, "That she only fucks black men, she's a snowbunny."

"Very good, Littledick, you have done your homework." Gina said clapping her hands a little, sarcastically, as she laughed, "It was clear that an old pervert with a midget dick like yours would know what a snowbunny is, although I have to tell you, girl, those buttocks look chiseled by the gods, what an ass."

His cock was throbbing non-stop as precum kept dripping from the tip.

Charlie turned around laughing. "You really weren't lying when you talked about his lack of stamina." she said still laughing.

BBC ONLY was written on the front of her white thong. He stared at her thong as his cock gave a little twitch and he leaked more precum.

"I'm sure you're an interracial porn addict, Littledick, which is why I'm sure this is going to blow your mind as well." she said pulling her thong down a little, seductively, showing her BBC SLUT tattoo that crossed her trimmed blond landing strip.

"Stumblebum!" he exclaimed again with his cock twitching and throbbing like mad.

"I knew you would love it." Charlie said with a naughty smile winking at him.

Charlie waited a few seconds for his cock to calm down, then she slowly turned around and bent over a little, separating her buttocks with both hands until only the string of her thong did not allow Littledick to see her asshole, suddenly with one of them she gave herself a strong slap on one of her buttocks.

"Stumblebum!" he exclaimed again.

"Girl, you better hide that ass of yours, it's a weapon of mass destruction." Gina said with a laugh, "We don't want Littledick to have a little accident."

Charlie turned around and sit down almost falling over with laughter looking at his cock bouncing and throbbing.

"3 edges without even touching his little dick, beat that." Charlie said, still laughing, looking at Gina.

They waited another few seconds for him to calm down again.

Then Gina rested her two big tits on the cardigan over his chest and brought her mouth close to his ear.

"I think you like her ass too much, you're going to make these two girls jealous." Gina whispered softly.

"Stumblebum! Stumblebum!" he yelled shaking.

Gina and Charlie started cracking up again watching his cock bouncing up and down like crazy dripping precum everywhere.

"See? I can do it too." Gina said laughing, "I hope you're ready because you still have a looong hour ahead of you." Gina said laughing harder as she sat back down in front of his small cock.

They kept taking him to the edge in turns, losing count when they had more than 100.

"We're already finishing, Littledick." Gina said smiling.

He was exhausted, his cock didn't stop throbbing and bouncing, he was practically on the edge all the time, a slight blow already made him reach the limit. Gina gently gripped his cock with two fingers and gave it a couple of very light strokes on the frenulum.

"Stumblebum!" he exclaimed in agony.

"My turn!" Charlie exclaimed smiling.

Charlie didn't wait a second, she grabbed his small cock by the base with two fingers, brought her mouth close to his cock and began to blow hard all over it.

"Stumblebum!" he exclaimed again with his cock bouncing, it was endless torture.

"Okay Littledick, we're done." Gina said, "Now we're going to look at your file, I hope you're lucky, cross your fingers."

She sat next to him, crossing her legs and putting her laptop on top.

"Let's see..." she began looking at the screen, "Francis Littledale Jr., Littledick to friends, 54 years old, virgin, I still can't believe you're a virgin Littledick, don't get me wrong, with that tiny dick It seems normal to me that no girl approaches you but with the money your father had you could have at least hired the services of a professional, if you know what I mean." Gina said with a laugh, "Although it's also true that she wasn't going to do much with that wretched cock of yours."

"Are you a virgin? How sad and pathetic..." Charlie said pouting.

"Let's move on..." Gina said, "cock size 1.3 inches, last orgasm 28 months ago, ruined, last real orgasm, never, in the 4 years you've been with me you've never had a real orgasm, that's very fucked up, you know that if it were up to me I would have let you cum from time to time but that stepmother of yours is a total bitch, don't you think?"

"Y-yes, Miss Gina." he said shivering, his cock still dripping rock hard.

"Now we will add up the points, depending on their behavior points will be added or subtracted, and in the end there are 4 possibilities, if they are 70 or less, they will go home with big blue balls, without orgasm, between 71 and 90 it will be a ruined orgasm, between 91 and 99 it will be a full orgasm and if they get to 100 points, which no one has ever done, they can have a full orgasm while looking at my bare tits, that would be great huh, Littledick?" Gina said unbuttoning a button on her cardigan, leaving only one buttoned that almost impossibly contained her two huge tits. Gina brought her tits closer to his face and began to sway them from one side to the other, almost coming out from time to time but containing them as if by magic.

"That would be a dream come true." Gina whispered in her ear.

"Stumblebum!" he exclaimed.

"Be careful Littledick, no accidents." Gina said smiling, looking at Charlie again, "Also for 500 more bucks you can roll a special dice, it's not a normal dice, it can give you 30 points but it can also take away 30, but to reach 100 it can only be for good behavior, no dice, although by order of his stepmother Littledick cannot roll the dice, also for each month without cumming 10 points will be added, although Littledick's case is special, he only has 3 points per month, orders from his stepmother, you know."

"Let's see, 28 months since last orgasm is 84 points, it was a ruined orgasm but an orgasm nonetheless, you have paid your dues on time, 20 points, you sent all the chastity control pics on time since the last time you came here 3 weeks ago, another 20 points, that makes a total of 124 points, very good Littledick."

"So he can cum looking at your naked tits?" Charlie said standing up and brushing his cock with his bare leg as she approached the laptop.

"Stumblebum! Stumblebum!" Littledick yelled, his cock beginning to throb again dripping with precum.

"Be careful, Miss Charlotte, he is really desperate, can't you see?" Gina said smiling.

"I'm sorry Littledick, it was unintentional." Charlie said laughing and sitting back down.

"No way, he has 124 points but I still have to subtract some and finally his stepmother's points, anyway don't think that all the boys reach these scores, Littledick is a very good boy, he does everything I order and never behaves bad, others are very lucky if they reach more than 90 once in a while." Gina said, "Aren't you my very good boy, Littledick?"

"Yes, Miss Gina." he said, still shaking.

"Lastly, I deduct points from all the boys if they have behaved badly, or if they have been late with the quotas or whatever occurs to me at the moment, really." Gina said with a laugh, "And also 4 points for any inches their little cocks need to get to 10 inches, my ideal size."

"Well, he's missing quite a few." Charlie said laughing.

"Yes, poor Littledick, in all you are missing 8,7 inches, we'll round it up to 9, as always, 4 points per inch is 36, if we subtract them from 124, that's 88." Gina said pouting, "Too bad, Littledick, three points and it would be a full orgasm, but hey, there's still your stepmom, she can subtract or add 15 points, if she adds 12 you'll even have the big prize, a full orgasm with my twins in all their glory, cross your fingers, Littledick."

"I'm going to video call hee right now." Gina said smiling, "I hope she answers this time, normally she doesn't even answer my calls, in those cases or if she answers but hangs up before giving him his points, 15 points are automatically deducted, something that has also happened sometimes, isn't it, Littledick?"

Then on the screen appeared a girl in her early twenties standing in the middle of a room, she was skinny, although she had tits that were too big for such a skinny body, and an ass that was also quite big and round, she had a perfect hourglass figure, her skin was white as porcelain and she had clear blue eyes, her black straight hair was loose, it was so long that it reached almost to her waist, Charlie thought she was one of the most beautiful girls she had ever seen. She was wearing a white top with no bra that barely contained her large bust and very short jeans that revealed half of her buttocks.

"Hello Gina, what do you want?" she asked.

"Hello Megan, It's about your stepson, he's here for an orgasm request." Gina said.

"Again? That little boy is obsessed." she said dismissively.

"Will you give him your points?, Otherwise you know that 15 points will be taken directly from him." Gina said smiling.

"Ok, but lets make this quick, I don't have so much time to take calls from my perverted stepson." Megan said.

Charlie found it hilarious that a 54-year-old man would be called a stepson by a girl less than half his age and couldn't help but laugh.

"Well, how many points will you give him?" Gina asked.

"Wait a second, show me Littledick Jr, I want to talk to him before I decide." Megan said smiling.

Gina turned the laptop towards Littledick.

Megan started laughing out loud.

"I'm sorry Littledick, but every time I see your tiny dick I can't help but laugh. And why are you wearing a thong over your face?" she said still laughing, "You know what? Don't answer, I guess it's your pervert stuff."

"You remind me of Littledick Sr., poor little thing, he was such a good boy, I don't remember how many times I took him to the edge that night, it was a game I played with him, count the edges, I know that we had broken his record that day, was it 300? or 400? I think so, over 400, I still remember how the poor boy begged for mercy, and asked me to please end his suffering, many, many times, over and over, edge after edge, pleading and begging, I have to say that even if you don't think so, I was a girlfriend who was fully dedicated to him, I unlocked him every night and played count the edges for at least two or three hours, every single day for 2 years, not letting him cum even once, until we finally got married, on our wedding night, right after a wild sex session with Deion, I let him into the bedroom, tied him to the bed, unlocked his cage and started to jerk him off slowly, I remember saying him, 'Littledick, get ready for the best orgasm of your life', how excited he was! you should have seen his face, full of joy and happiness. I had been taking him to the edge over and over again for 6 or 7 hours when I told him, 'It's okay Littledick, I think you deserve it for being such a good boy, after years of waiting I am finally going to show you these big beautiful tits of mine that obsess you so much and I'll finally let you cum' then I slowly unbuttoned the white corset I was wearing and when I got to the last button he was gone, I still remember his huge, swollen blue balls, and his tiny cock throbbing until the end, as if desperately screaming 'Please! Let me release!' could never be, he left with them full and swollen to the brim and with his tiny dick with a raging boner, poor, poor boy, so sad." she said pouting. "At least he had time to see my big beautiful tits before he was gone, or so I think, I'm not sure."

"Yes, very sad, but what about Littledick's points?" Gina asked.

"Oh, yes, I'm sorry, I completely lost track remembering my dear little hubby." she said smiling, "So you want to cum, Littledick?"

"Yes please." he pleaded with his throbbing cock bouncing up and down.

"I don't know if you really deserve it, have you been a good boy?" she asked.

"Yes, yes, I have been a very good boy, please." he begged again, trembling.

"Gina, how many points does he need to cum?" Megan asked. "The truth is that he has 88 points, even if you take away 15, a ruined orgasm is guaranteed, but with just three points I'll give him a full orgasm, and if you give him 12 I'll even show him my tits." Gina said smiling sarcastically.

"No, no, that would be too much, with what happened to his father when he saw my tits, I don't want the same thing to happen to Littledick Jr." Megan said thoughtfully, "But I think he deserves at least the three points since he's been such a good boy, right?"

"Actually, he's been a very, very good boy, haven't you, Littledick?" Gina said.

"Hey girl, what are you doing?" a man's voice was heard.

"Oh, it's Deion, hello daddy, I'm talking to my stepson." Megan said.

"That perverted old loser?" said the man.

"Don't be mean to him, daddy." Megan said laughing.

"Fuck that little dick loser!" Deion said, then appeared on the screen, a muscular, shaved black man in a skintight white tank top and sagging jeans.

Then Charlie realized, she already knew Deion, he and Marcus had fucked her together several times in the last few months.

"Deion? It's me Charlie!" Charlie said, "Marcus's girlfriend, remember me?"

"Charlie, how's it going girl?" Deion said, "How could I forget that perfect bubble butt of yours?"

"Well, you know, whenever you want you can have this ass." Charlie said turning around, showing her ass to the screen and smacking herself hard, "I haven't forgotten about your big cock either."

"Damn girl! What an ass! You're making me so horny." he said pulling his huge cock out of his pants, "Megan, give me one of your amazing blowjobs."

"Now daddy? Can't you wait?" she asked.

He brought his dick up to her face.

"No, suck me now." he ordered.

"But, daddy..." she said, but before she finished the sentence he put his cock in her mouth.

"Fuck yeah, suck me good!" he exclaimed.

He began to squeeze one of her huge tits while she sucked on his cock.

"To the bottom!" he exclaimed grabbing her hair with his other hand until she shoved his entire cock down her throat, "That's it, bitch!"

"Stumblebum! Stumblebum!" Littledick yelled, Gina quickly moved the laptop out of sight.

"That was too hot for you, huh Littledick?" Gina said smiling.

"Turn that shit off!" the black man said.

"Sorry, I have to leave you." she seemed to say, with his cock still in her mouth and the call was cut off.

"Whew, Deion, what a man, he likes to be very dominant, every time we fuck he takes my breath away, he's a real man." Charlie said getting a little horny.

"Yeah, I wasn't expecting that." Gina said laughing, "What a coincidence."

"So I'm going to have a full orgasm?" he asked shakily looking at Gina.

"Sorry Littledick, I would like nothing more than that but your stepmom hasn't given you the points, you know that if she doesn't tell us exactly the points she gives you, it's like she doesn't pick up the call, 15 points will be deducted, but, hey, at least it's a ruined orgasm." Gina said.