Small Penis Prison Ch 33

Their room was huge and luxurious decorated in red and gold, with a large double bed and large windows.

"Let's go to the pool for a while." Charlie said.

"Why did you tell me I didn't have to wear the cage?" Ryan said after putting down their bags.

Then they heard a moan of pleasure coming from the next room and Charlie burst out laughing.

"Those aren't wasting any time, right?" she said still laughing.

"Answer to me." Ryan said angrily.

"Relax, little boy." said Charlie, "If you want your little cock out of that cage soon you better behave yourself, understand?"

"Yes." He said, "I'm sorry, Charlie."

"That's better." She said smiling, "Well, the thing about the cage was a mix-up, I must have misunderstood, it's not a big deal, is it?"

"Well..." Ryan said.

"Well, there's nothing more to talk about." Charlie said when suddenly they heard another high-pitched scream coming from the next room, "See? People here are already enjoying the trip and we're here arguing, let's go to the pool."

"And when are you going to ask Mrs. Laura for the key?" Ryan asked with his eyes fixed on Charlie's beautiful, perfect ass as she walked ahead of him swaying it from side to side seductively towards the pool, she had taken off her shorts and now he could see her round ass in that tiny black thong through the fishnet sarong.

"Why do yo care so much? You are completely forbidden to cum." she said without even looking at him.

"But it's too small, it squeezes me all the time and the minute I get an erection it hurts a lot." Ryan said.

"Then I advise you not to look at my ass for a second." she said with a giggle.

When they arrived at the pool they saw that Cecilia was already lying on a lounge chair sunbathing and they lay down next to her.

"Where's Roro?" Charlie asked.

"He's getting me a drink." Cecilia said.

"Good idea, Ryan, be nice and bring me a mojito." Charlie said.

"Right now." He said.

When he arrived at the bar he saw Roro waiting for the bartender.

"Have you already ordered?" Ryan said.

"There's no one working here." He said.

"Maybe we have to serve ourselves." Ryan said, jumping over the bar to start preparing the mojito.

"And who do we pay for the drinks?" Roro said.

"Everything is free on this ship, darlings." Lia said, grabbing a stool and sitting next to Roro, her huge ass sticking out from all sides of the stool, "While you're at it, make me another of whatever you're preparing, please."

"Do you like mojitos?" He said.

"I love it, especially when such a cute boy does it to me." she said winking at him.

Was that girl flirting with him? It can't be, Ryan thought, since he got out of prison, Charlie had made him to eat healthier and exercise regularly so he now had a fairly athletic physique, not very muscular but he even had his abs, something that had never happened to him before in his life, maybe that was the reason why some girls smiled at him on the street or on the subway, something that had never happened before either.

"It will be my pleasure, then." He said winking at her which made her smile shyly, she was little older than him and that made her even more attractive.

Ryan only had eyes for Charlie but with the cuteness of Lia and that huge and unforgettable ass she had, his cock was about to burst in its cage, round asses were his weakness, he couldn't help it, big ones, small ones, black, white, it didn't matter, it was beyond his strength, as soon as a nice round ass passed in front of his eyes he was hypnotized, it could also be because he hadn't cum in months...or the constant edging...who knows.

"So there are no waiters or any other staff working on this ship?" Roro asked.

"Something like that, they will inform you later, don't worry." Lia said still smiling at Ryan, "And what about that mojito?"

"Relax. The best things take time." Ryan told her.

"Is that the excuse you give yourself for going so long without cumming?" Lia said looking at him with her big caramel eyes and showing her perfect white teeth with a big smile.

"And what do you know about how long I have been without cumming?" He said, with a red face just as he gave her her mojito.

"I know it all, dear." She said, winking at him again as she took a sip from the straw, "By the way, this is delicious, thank you very much."

Then she got up and went to lie down on another lounge chair, swaying her big, beautiful ass back and forth along the way knowing full well that Ryan was watching her, drooling, his cock trying to get hard inside his cage and his mouth wide open.

"What an ass." he said to himself.

"I'm telling you." said Roro who had not missed a second of the show either.

"Do you want me to make you a cocktail or something?" Ryan said looking at Roro.

"Well, if you know how to make a margarita I would appreciate it because I have no idea." he said smiling.

"Of course." He said, getting down to it, "And tell me, how are things going with Cecilia?"

"Very good, she is the best." he said.

"How lucky, she's a beautiful girl." said Ryan, "I only know her a little from the SPP and from what I was told about her she was pretty tough on her boys, although she might be a completely different person outside of there, I guess."

"Well..." Roro said doubtfully, "I'm not going to lie to you, she's the first girlfriend I've had so I can't compare but I would like to have some intimate moments with her, if you know what I mean."

"You mean fuck?" Ryan said.

"Anything." He said, "We haven't done anything since we've been together, for months, we've gone to dinner together, to the movies and so on but nothing else, we've just kissed a couple of times but that's all."

"Well, it will come." Ryan said, "Although I guess her fucking your little brother is kind of fucked up, right?"

"That's the other thing that bothers me, nothing with me but she fucks my brother 2 or 3 times a week, at least." He said, "At first she asked me if I cared but I didn't expect her to keep fucking him, or at least so frequently."

"And who was the guy who was waiting for your mother?" Ryan said.

"Silver." Roro said with a pout.

"Silver? That's his name?" Ryan said.

"Yes, a total asshole." He said, "He treats me terribly, he calls me a faggot all the time and I still have to put up with he fucking my mom every night like an animal, her screaming as if she didn't care about having neighbors and hitting the headboard over and over again against the wall, a real nightmare."

"And what about your father?" Ryan said.

"He and my mother divorced when I was 10 years old, he caught my mother and Silver in bed one day when he came home early." He said, "Silver worked as a plumber in the neighborhood and had a reputation for having fucked all the wives in the area, even my father believed that Lars was Silver's biological son but he never took the DNA tests, I believe it too, he doesn't look anything like him and much like Silver."

"And you see him often?" Ryan said.

"Yes, although a few years ago he married another woman, a total bitch, having so much money attracts many gold diggers." He said, "I'm sure she's only with him for the money and she also cheats on him, I know. She calls me beta boy when I visit them at their house, but every time I say something to my father, he doesn't listen to me, it seems like she has him by the balls, literally."

"Boys! How are those drinks going?" shouted Cecilia from the lounge chair.

"They're coming!" Ryan said, giving his drink to Roro and walking towards the girls.

Just when they arrived they were joined by the tall man and the short woman couple. They were both naked and sweaty and his cock seemed ready to burst in its cage.

"Hello!" the woman said smiling, "I'm Amelia and this is Hector."

"Nice to meet you." said Charlie, "You're the ones who were making all that noise in your room, right?"

"Could be." she said with a naughty smile, "I can't go long without my Hector's huge cock inside me, I'm addicted."

"I don't know how you were able to fit all that inside the cage, it seems huge." Cecilia said without taking her eyes off Hector's caged cock.

"Years of practice." She said with a giggle, "Hector, go get me a Martini, please."

"There are no waiters, if you want I'll prepare it for you, I know how to make a lot of cocktails." Ryan said.

"I haven't seen room service either." Amelia said, "Isn't there anyone working on this boat?"

"Laura will tell you everything later, don't worry." Lia said without flinching, lying on her lounge chair, "And you, cute boy, be a sweetheart and make me another one of those delicious mojitos of yours."

"You're talking to me?" Ryan said.

"Of course." She said smiling at him and winking at him.

Ryan looked at Charlie who had a strange smile.

"Yes, cute boy, go make your friend a mojito." she said still with that smile.

"Hector go with him and get me a martini." Amelia said, lying down with her legs open, showing her hairy pussy without any shame.

Ryan went with Hector to the bar and Roro joined them shortly after.

"Better to leave the girls alone, I don't have good experiences being alone with a group of girls." Roro said.

"Hector, right?" Ryan said, "I'm Ryan."

"Nice to meet you." He said.

"I'm Ronnie." Roro said, "What was that noise you were talking about earlier?"

"Looks like Hector and Amelia had some fun before heading out to sunbathe." Ryan said smiling, "You lucky bastard, Charlie doesn't even intend to get my key back anytime soon and you're fucking as soon as you get to your room."

"It's not what you think." Hector said.

"What are you talking about?" Roro asked.

"Amelia doesn't let me cum when we fuck, I better hold on or else I will be punished, and we fuck a lot, believe me." said Hector, "And she hasn't let me cum in a long time, nowadays it's almost impossible to hold it in, it's getting very very hard."

"Is she your wife?" Ryan said.

"Yes, we've been married for 5 years." he said, "And it's been the same ever since."

"It was always like this?" Ryan said.

"Yes, I was quite a flirt, I could get any girl I wanted." He said, "When I met Amelia she was the shy, geeky friend of a hottie who I was fucking at the time, when I found out that she was a rich heiress I told myself that although she wasn't the type of girl I normally dated, she was quite cute so I started dating her, although I'm ashamed to admit it, it was because of her money, I knew that with her I could live like a king."

"And how did you end up in your situation?" said Ryan, "She seems pretty cheerful and unimportant."

"Don't let her fool you, I made that same mistake, under her appearance of a milquetoast she is a true lioness, a very sadistic one." He said, "At first everything was great, she is naughty in bed, again, don't be fooled by appearances but soon everything started to change, she knew my reputation as a womanizer so the first thing she did was put a driver who took me everywhere, she said it was for my comfort but that was bullshit, since the sex with her was great I didn't protest, then came the chastity cage before we got married, I agreed because I knew the prize was worth it but what I didn't know is that she already had several lovers, I found out on the wedding night when she fucked some of them, then she started restricting my orgasms more and more and to this day, which I am at her complete mercy."

"What a story." Roro said.

"Don't get me wrong, I have a great life, servants for everything, I don't have to work and at home I do whatever I want, she is the vice president of her father's company so she works a lot, but when she is at home she just wants to fuck or have her pussy or ass eaten all the time, that woman is insatiable, everything would change if she let me cum more often." he said crestfallen.

"And why don't you get divorced?" said Ryan, "Golddiggers do it all the time and take half of their ex-husbands' fortune."

"She forced me to sign a premarital agreement, it was a moment of weakness, I hadn't come for a long time and she promised me that if I signed it, she would let me have an orgasm, I signed without even knowing what I was signing, and all so that in the end that bitch ruined my orgasm." He said as if he were remembering it vividly, "Plus she has told me several times that if the idea of ​​getting divorced crossed my mind she would flush the keys to my cage down the toilet."

"Hector, what about my martini?" Amelia said with a sweet tone as she continued sunbathing with her legs open on her lounge chair.

"I'm coming dear." He said.

"Do you know that I know her uncle?" Charlie said to Ryan pointing at Amelia when they came back with the drinks.

"Yes, she is a friend of Francis, dear." Amelia said taking a sip of the martini.

"Well, I don't know if I'd say I'm friends with Francis Littledale." Charlie said laughing.

"Are you Amelia Littledale?" Roro said, "That's why your face sounded familiar to me, your family is filthy rich."

"Yes, my father is the one who runs the whole business, I am second in command, my uncle is the black sheep of the family so to speak, totally useless." Amelia said smiling, "That's why my grandfather gave his share of the inheritance to his beautiful young wife."

"Do you know Megan? She's super fun." Charlie said.

"I don't dislike her but my father is doing everything possible to recover what my grandfather left to that girl."

"And why did he left Megan in charge of her son, a man more than twice her age?" Charlie said with a big smile, all of this seemed to amuse her a lot.

"My uncle is a wanker, a liar, and a bum, he always has been, my father knows it and my grandfather knew it, I guess my grandfather thought that leaving Megan in charge of my uncle's share was giving him some kind of punishment, I don't know, my family doesn't tolerate the weak." Amelia said, "I didn't know he was a virgin, but I'm not surprised, and what you told me about his tiny cock is hilarious."

"Gina calls him Littledick." Charlie said laughing.

"The name suits him perfectly." Amelia said, laughing too.

"Wait a second, Littledale?" said Lia who seemed to have woken up from a nap, "That's the name of one of Teddy's partners, that's why Laura said someone important was coming, I thought she meant her sister."

"I don't expect any special treatment, don't worry." Amelia said taking another sip of her martini, "I just hope to relax and enjoy my vacation."

"Hello, I'm Ivy and this is my pet, Goo." said the woman they had met at the entrance.

This Goo followed her with an umbrella, constantly blocking her from the sun while she sat next to them as if he did not exist.

"So you're Laura's sister?" Lia said after the introductions.

"Yeah." She said, lying down while Goo moved a little to try to shade her with the umbrella.

"It's strange that being twins, your sister had hardly even mentioned you." Lia said.

"Well, we hadn't talk for years but now we get along again." she said.

"It must have been a very big dispute, she told me that when you were young you were very close." Lia said, "She told me you were real sluts."

"Laura always so rude." Ivy said, "What happens is that my sister and I have always known how to take advantage of our looks, between the two of us we have broken up many marriages, later we became real gold diggers, I got a mansion in Miami from my last husband, Louie through divorce, almost 500 millions, and that's just the last one, I've had 3 divorces and all of them very lucrative, men only think with that little appendage they have between their legs, like here my pet Goo, although you can't even call him a man, isn't that right, dear?"

"Yes, Miss Ivy." Goo said without looking up from the ground.

"And Goo is your last husband?" Cecilia said.

"Of course not." she said, laughing out loud,

"He's my ex's son, since I married his father I started training him secretly, he was a party animal, a whoremonger and a drug addict, being the son of a billionaire, he had anything he wanted, I saw how he undressed me with his eyes since I arrived at that house and I took advantage of the situation."

"And how did you do it?" Charlie asked.

"Easy, as I told you before, men think with their cocks, even one as little and pathetic as Goo's, so I started making advances and he completely fell into my trap." she said with a smile, "Before long I had him locked in a chastity cage and eating out of my hand, but that was only the beginning."

"Then what?" Cecilia said.

"Then the training began, do you know Pavlov's experiment?" she said.

"A bit." Amelia said smiling, "This looks interesting."

"It's very simple, look." Ivy said looking Goo in the eyes, "Goo, dear, imagine a huge, veiny black cock."

Ryan saw how Goo closed his eyes tightly with an expression that was difficult to decipher, with a mixture between pain and pleasure, then he saw how in a few seconds his cock became hard inside its small cage, dripping precum and throbbing like crazy.

"That's it, good girl." Ivy said with a mischievous smile, "Now imagine me sucking that huge black cock up and down, sweetly."

Goo's cock seemed ready to burst inside the cage and a waterfall of precum flowed from the tip.

"Alright..." she said with a playful tone, "Now imagine that big cock sticking into my pussy and fucking me until I cum over and over again."

Goo's cock throbbed angrily and he let out a little moan with his eyes still squeezed shut.

"That's my girl." said Ivy, "What do you think?"

Ivy stared at the rest of the group who were staring at them with their mouths open.

"That's nothing." said Cecilia laughing, "My SPP boys also get horny if I start talking dirty to them."

"No, no, no..." Ivy said laughing, "You see, this is years of training, I have conditioned Goo so much that today he can only cum while eating a creampie from my pussy, isn't it like that, dear?" said Ivy, "And only with my express authorization, what's more, the next step is that his cock could only get hard when I fuck black men but we still have some more training to do."

"But how?" Charlie said.

"Years of positive and negative reinforcement." said Ivy, "For years when I was fucking another man it was the only time I allowed him to have pleasure and I have only allowed him to cum when he cleans my pussy, to this day the smell and taste of cum makes him super horny, it takes him right to the edge in an instant."

"That's amazing!" Amelia said, laughing, "And what about negative reinforcement?"

"Look." said Ivy, "Goo, open your eyes."

He opened his eyes and looked at her, his cock still rock hard squeezed inside its cage. Then she slowly lowered her swimsuit top, leaving her big, beautiful tits on display and now it was Ryan who was beginning to have an erection inside his cage.

"Look at them." Ivy said smiling, "They're very pretty, huh? They cost me a lot, don't they look real?" Now she said it looking at Ryan who had his eyes glued to her tits.

"Y-yes, very, very pretty." he said almost stuttering.

"Thank you dear." she said, "I went to the best surgeon in the country, he made them look like a twenty-year-old girl's tits, perky and big, and they look completely real."

Then Ryan looked at Goo's cock, now it was all shrunken it had almost disappeared inside its cage.

"Oh my God!" Amelia exclaimed, "That was fast."

"For years I've trained Goo to associate tits with pain and suffering, so when he sees them his cock shrinks and returns to its pathetic, tiny state." Ivy said, laughing, "Many days of ballbusting and CBT, but they worked out in the end."

"You've screwed the boy's head over." Cecilia said laughing.

"Maybe, but you're much happier this way than with the life of debauchery you led before, aren't you, dear?" Ivy said, pulling up her swimsuit again, "The poor boy doesn't know where to look on the rare occasions that I let him jerk off watching me fuck one of my bulls, if he looks at my big bouncing tits his cock goes limp, so he has to be very careful, that's why I always tell him to focus on their huge cocks and his little cock comes to life again."