Small Penis Prison Ch. 28

"Roger, I'm here!" Gina shouted as soon as she arrived home.

"Hello my Queen." He said, quickly kneeling in front of her.

"How is my good little boy?" she said.

"Good my queen." he said still kneeling.

"Go make me a drink while I go change my clothes." she said, "A special guest is coming today."

"My queen, I must tell you that Holly is here." said Roger, "She arrived a few hours ago."

"What are you talking about?" said Gina, "Here in our house?"

"Hello auntie!" exclaimed a girl in her early 20s coming out of the kitchen with a can of soda.

"Holly!" Gina said confused, "What are you doing here? You should be in college, if your mother finds out she's going to be so pissed."

"I'm going to drop out of university, it's boring." Holly said taking a sip of the soda.

"What? No way!" Gina exclaimed, "You're the smartest in the family, and as far as I know one of the smartest girls in the country, didn't you have an IQ of a genius?"

"Yes, but that's worthless." She said, "I want to make money like you and Polly, not work my ass off to make a shitty salary like Mom." she said.

"Sometimes I doubt you're that smart..." Gina said, "And please, if you're going to stay here don't go around the house half naked, look at Roger, my poor boy, his tiny cock is about to burst his cage."

The two stared at Roger who did not take his eyes off Holly as if he were a hunter watching his prey, she was only wearing a fairly short white top that made most of her big tits visible from below and a white thong, Holly was much shorter than her sister Polly, although at 5'8 feet she was taller than most girls, she was a curvy girl like Gina, but a little more plump, with bigger tits and ass, with her long black hair, blue eyes and very pale skin, many tell her that she looks like Kat Dennings.

"One of the reasons mom doesn't let me come see you is because of your perverted little hubby, now I see what she meant." she said, laughing.

"Well in his defense I have to say that he hasn't cum in several months." Gina said laughing, "But hey, that's not the point, you can't stay here, your mother would kill me."

"Please, it'll be like I'm not here, I promise, I'll behave." she said pouting.

"Okay, but you better call your mother, I don't want any trouble." Gina said, "I'm expecting a visitor today, I don't want you to bother us, ok?"

"Of course, I'll be a very good girl." she said smiling.

"Roger, bring me that drink, I really need it now." Gina said.

Roger ran away and returned in a few minutes.

"I love how those huge blue balls dance from side to side when he walks." Holly said with a giggle, "I could spend all day looking at them, you must be desperate to cum, right little boy?"

"Yes, Miss Holly." He said looking at the ground turning red.

"The truth is that I have never seen your hubby's cock but with that flat cage it looks like he doesn't even have one." she said, laughing, "Is it too small?"

"It's tiny, believe me." Gina said smiling. "When you fuck you don't even feel it, right?" Holly said.

"We've never fucked, who do you take me for?" Gina said, laughing while Roger continued looking at the ground.

"No? You must miss fucking a good pussy, don't you little Roger?" Holly said smiling.

"No, no, Roger is a virgin, he doesn't know what it feels like to have his cock inside a pussy." Gina said smiling.

"No way!" Holly exclaimed in amazement, "Poor boy, at your age and you're still a virgin, you could be my father, how does it feel knowing that guys half your age are fucking girls like me every day while you're a virgin cuckold in chastity? you don't need to tell me, pretty frustrating, right?" Gina and Holly started laughing out loud while Roger turned even redder.

"Don't be like that." Gina said still laughing, "He already has enough punishment knowing watching me fuck real men everyday, you don't need to remind him of all the hot girls who are being pounded by huge cocks while his tiny cock is locked in its cage."

"There's nothing to be ashamed of, little boy." She said, "I'm surrounded by virgins on campus all day, and I know that many of them jerk off looking at my photos, so it's a shame you can't even do that."

"Yes, your mother told me that she didn't like it at all that you uploaded those provocative photos to your social networks." Gina said.

"It's fun, I also do social work, there are a lot of loser virgins jerking off non-stop looking at my photos, I'm sure if it weren't for good girls like me, some of them would be harassing some poor girl." Holly said smiling.

"Yes, of course, tell your mother that." Gina said.

"By the way, who are you waiting for?" Holly said.

"It's a new client, but this one is special." Gina said.

"Why?" Holly asked.

"It is a long story." she said.

"I have plenty of time." Holly said smiling.

"Do you know Amelia?" Gina said, "She was a friend of mine and your mother's years ago, although we've lost touch a bit now."

"Yes, that friend of yours who married the millionaire genius, her stepson Arthur is in one of my classes, what a loser, a virgin like you, Roger." Holly said looking at him.

"Well, she told me that her stepson Artie used to get very good grades, but since he went to college his grades have dropped so she called me to help him." Gina said.

"Arthur? He spends all day jerking off in his room." Holly said, laughing, "Wes, one of my fuck buddies is his roommate and he's caught him jerking off a bunch of times to my photos, one day after fucking him I forgot my thong there, and I never got it back, Wes thinks Arthur kept it, I don't want to know all the dirty things he's done with it."

"Well, I'm going to become his keyholder, Amelia told me to do whatever it takes to straighten him out, that boy doesn't know what's coming to him." Gina said laughing.

"Oooh, let me tease that virgin." Holly said pouting, "Please auntie, I promise I'll do anything you tell me, please."

"No, no way, this is what I do, you don't know anything about this business." Gina said very seriously.

"Yes, I know, Polly tells me everything she does and I think I would be more than capable, it's easy." she said.

"You say that because you have no idea, and you're also inexperienced. I spent half a year teaching Polly until she had her first boy." said Gina, "I said no and it's no, and there's nothing more to say."

"You're worse than mom." she said angrily leaving the room.

Half an hour later there was a knock at the door, Gina went to answer it, she had told Roger not to leave his room, she didn't want Arthur to get scared seeing a small 46-year-old man suddenly walk by, naked only wearing a chastity cage and Holly had locked herself in her room since they had argued.

"Hi Artie, how are you doing?" Gina said with a big smile.

"Hello, you must be Gina, right?" He said very nervously.

"Yeah!" She said, "I've known your stepmother for years but since she married your father we have grown apart a bit."

"Yes, she told me." He said.

"It's okay, we're not here to remember old times." She said smiling, "Come in, don't stay at the door."

Arthur was a short boy with short black hair, very thin and with large metal glasses, not very attractive to say the least.

"Follow me." she said.

Gina had put on a beige two-piece dress, with a very tight skirt that reached above the knee, a blazer, and a white blouse with 2 buttons unbuttoned that showed a lot of cleavage. As they walked to her office, Gina swayed her big ass exaggeratedly, knowing full well that Arthur would be taking a good look at her.

"Lie here, please." She said, pointing to a stretcher next to one of the walls of her office.

"Are you some kind of doctor?" He said very nervously getting closer to the stretcher, "Amelia hasn't explained to me why I'm here."

"Something like that, I improve the lives of all my boys, I make them more focused on the important things." she said with a mischievous smile, "Amelia told me that lately you were quite distracted and your grades have gone down, I think I can help you, in fact, I'm sure that your grades will improve incredibly."

"Well, my grades have dropped a little but I can fix it, I don't think any of this is necessary." He said looking at the stretcher.

"Lie down, now." Gina said softly but convincingly.

Arthur lay down and Gina approached him and began to tie him with straps on his wrists, ankles, waist and when she was tying the last strap that held his head she leaned over putting her cleavage in his face while she smiled, that boy was really doomed.

"Is all this really necessary?" He said very nervously.

"Of course." She said, taking a pen and a notebook and sitting next to him, "Now I'm going to ask you some questions and you have to be very honest, I want you to know that I have a sixth sense to know when a little boy is lying to me, so don't lie, I'll know."

The boy looked at her without saying anything with a mixture of fear and confusion.

"Why do you think your grades have dropped so low?" Gina said.

"I don't know, I guess I'm a little distracted." He said.

"With what?" she said, "You should be focusing on studying."

"Well, partying, going out with girls and stuff." he said timidly.

"Oh yeah?" she said smiling, "So you're a bad boy, you fuck a new hot girl every night going from party to party, huh?"

"Yes something like that." he said with a nervous smile.

"And how many girls do you usually have sex with in a week?" Gina said.

"2 or 3, it depends." he said, slowly relaxing as Gina took notes.

"And do you have one special girl you sleep with more often?" she said.

"Well, I don't know..." he said.

"Name one, the one that makes your dick harder." she said.

"Holly, I guess." He said.

"Holly? That name sounds familiar." she said, laughing to herself, "And what is she like?"

"She has a very pretty face, with beautiful blue eyes and long black hair." He said.

"She looks gorgeous." Gina said smiling, "And what is her body like?"

"Well..." he said.

"Don't be shy, does she have tits as big as mine?" Gina said, "You haven't taken your eyes off them since you arrived."

"Bigger." He said, "She's...thick, huge tits and a big round butt, do you know Kat Dennings? She looks a lot like her."

"What a woman, you are a lucky boy." Gina said holding back her laughter, "And she's just one of the many hot girls you're fucking lately, I'm sure you're quite the bull in bed."

"I suppose." he said with a smile.

"Well, let's get to the physical exam, now don't be scared, I'm just going to strip you from the waist down." Gina said getting up.

"What?" He said trembling, "No way, why?"

"I have to take measurements of your body, don't worry, I'm not going to be scared, I've seen a lot of big cocks in my life." Gina said pulling down his pants and boxers.

Gina started laughing out loud, the boy had his cock fully erect and it was no more than 3 inches.

"And with this tiny cock you fuck all those hot girls?" she said laughing, "Look boy, I already told you at the beginning that I know perfectly well when little boys like you are lying to me and everything you have told me is bullshit."

"What? But..." he said.

"Shut up!" Gina said, "Let's start again, what do you think is distracting you?"

"Girls, that's the truth, I swear." He said.

"And that Holly in particular, right?" Gina said with a little smile.

"Yeah." he said turning red.

"Is she your friend?" she said.

"No, every once in a while she fucks my roommate." He said.

"While you're in the room?" Gina said.

"Sometimes." he said, "But she won't let me look, when she comes she makes me cover my eyes with my sleeping mask but I can hear her moans."

"And I'm sure when you're alone you jerk off your tiny cock thinking about her, right?" Gina said.

"Yeah." he said turning red again.

"Does that Wes guy have a big dick?" Gina said.

"Yes, it's huge." he said, "And he can be fucking for hours, he brings girls almost every day to our room while I'm trying to sleep in the next bed."

"And that makes you jealous?" she said, "You'd love to stick your tiny cock in Holly's gorgeous pussy, wouldn't you?"

"Yeah, he's a lucky bastard, she's perfect, plus she's the smartest girl I know." He said more calmly.

"Poor boy, you have to watch your roommate fuck the girls of your dreams, what a shame." Gina said, "Tell me one thing, and be honest, are you a virgin?"

"Yeah." he said, turning even redder.

"There is nothing to be ashamed of, there are guys like your roommate who are real men and fuck hot girls and then there are other little dick boys like you, who are addicted to jerking off, it's the order of things, you can't fight that." said Gina, "How many times do you masturbate a day?"

"I don't know, maybe once." he said trembling.

"Bullshit, tell me the truth." She said looking at him seriously.

"3 or 4 times a day, on days off it can be even more." He said.

"That's it, that's your problem, you're obsessed with girls, especially that Holly girl, you're probably even afraid of them, and you spend all day thinking with your little cock and jerking off non-stop." Gina said getting up, "Don't worry, I have the solution."

"Do you? And what is it?" He said, "Are you going to help me not be so shy around girls?"

"Much better than that, I'll be back in a moment." She said smiling and winking at him.

Gina went to her room to get one chastity cage that Polly had left there in the morning. Passing by the room where Holly had settled, Gina saw that she was lying on the bed listening to music and decided to enter.

"Go away, I don't want to talk to you." she said without looking at her.

"Okay, whatever you want." Gina said, "I had a proposal to make you but if you're not interested I'm leaving."

"A proposal? About what?" Holly said looking at her as she turned off the music.

"I have decided that I will let you participate but if you are no longer interested I will leave." Gina said smiling.

"Stop playing, auntie, let's torture that poor boy." Holly said smiling.

"Okay, but you will do everything I tell you, understood?" Gina said.

"Yes do not worry." she said, "Do you want me to change my clothes? I'm in my pajamas."

Gina took a good look at her, she was wearing pajamas that were too small for her, it was a very tight pink romper with little red hearts that must have been from when she was a teenager, before her body had developed. Her huge tits were overflowing, the top three buttons would be impossible to fasten even if she tried with all her might, leaving her with an incredible deep cleavage.

"You know what?" Gina said smiling, "I think you look perfect dressed like this."

"I brought my assistant, I hope you don't mind." Gina said sitting back down in the chair.

"Hey Artie, it looks like your tiny cock is happy to see me." Holly said with a naughty smile as she stood next to Arthur.

"Holly? What are you doing here?" He said turning red again, his cock was hard as a rock.

"It is a simple coincidence, Gina is my aunt." She said, "Don't worry, I'm sure we'll have a great time together."

"You should know that Artie has a huge crush on you." Gina said, "What was that thing you told me before? Oh yeah, Holly is perfect and the smartest girl I've ever met."

"Oooh what a sweet boy, you're going to make me blush." Holly said winking at Arthur.

"Holly help me, let's sit him down." Gina said.

Between the two of them they moved several levers and the stretcher became some kind of chair with Arthur sitting but still completely tied.

"Better." said Holly, "Now you can enjoy all my charms."

"Artie's a virgin, aren't you, little boy?" Gina said.

"Yy-yes." he said almost stuttering.

"No way!" Holly said making a sad face, "I didn't know, poor thing, half the campus fucking like rabbits and you're still a virgin, what a shame."

"I guess it's because of his tiny dick." Gina said.

"Don't be like that auntie, I like it, it's a cute little cock." Holly said, leaning in to get a closer look.

Arthur was gawking at Holly's tits as she leaned over and his little cock began to twitch.

"Well, let's see how your little tool works." Gina said.

"Can I do it, aunt?" Holly said looking at Gina pouting.

"Are you sure?" said Gina, "I don't know if you have the experience to do it."

"Of course I do, Polly has taught me a lot of tricks." she said.

"Well, you should ask Artie, if it's okay with him, no problem with me." Gina said.

Holly knelt in front of him and looked into his eyes.

"Artie, would you please let me play with your little cock, I'll be gentle, I promise." Holly said pouting again.

"Yes, yes, of course." He said quickly with a nervous chuckle.

"Thank you Artie, you're a very good boy." Holly said, gently grabbing his cock with one hand, "Look auntie, it's so small it disappears in my hand!"

"It's normal with little boys like Artie, that's because you're used to big cocks from real men, with these small cocks just using a couple of fingers is enough," said Gina.

"You're right, all the guys I've ever fucked had cocks at least twice as big as this one and they were still flaccid." said Holly, starting to rub his cock slowly with her thumb and index finger, "A few months ago I met a very hot guy at a club, we made out and went to his house, when I pulled down his pants I saw his small cock, well, it was bigger than yours, Artie, but at most it would be 5 or 6 inches and I have a rule, I don't fuck anything that isn't at least 7 or 8 inches and if it's 7 it better be extremely thick, so after laughing out loud I told him to jerk off and left."

"What a bitch." Gina said laughing.

"Don't talk nonsense, you wouldn't have fucked him either." Holly said.

"Of course not, but if you say that he was so hot, I would have let him eat my pussy and give him a handjob, I love edging small cocks, some of them I have even ended up ruining their orgasm, but usually I am a good girl and I let them have a complete orgasm, it all depends on how they eat my pussy and the size of their cock, if it is too little it is a guaranteed ruined orgasm." Gina said laughing, "You have a lot to learn, dear."

Arthur began to moan.

"Are you close, little boy?" Holly said, looking into his eyes as she continued jerking him with her two fingers.

"Yeah." He said.

"Well you better hold on, it's not time for you to cum yet." she said smiling.

"I'm very close." he said brokenly.

Holly let go of her cock and stared at Gina.

"What's the plan?" she said.

"Excuse me girls, but I don't understand anything, what are you going to do to me?" Arthur said very nervously with his small cock dripping a little precum as it throbbed.

"It's very simple." Gina said showing him the cage, it was a small model with a size of at least an inch, "Do you know what this is?"

"Yes, I think so." He said even more nervous.

"Tell me what it is." Gina said.

"A chastity belt." He said.

"Very good!" she said, "What a smart boy."

"How cute." Holly said looking at the cage.

"Well, we're going to lock your little cock in this cage at least until you finish college, and if you ever want to cum again you better start studying hard because the only way we're going to let you have an orgasm is if you get straight A's on your exams." She said looking into his eyes, "The only question I have is whether we'll let you cum today or not, what do you think Holly?"

"I think we should let him empty his balls one last time before we lock him up." She said smiling, rubbing his small cock with two fingers again, "When was the last time you came?"

"2 days ago." he said trembling again.

"So long?" said Holly, "But you said before that you jerked off several times a day, I think you're lying to me, little boy."