Small Penis Prison Ch 34

Ryan and Charlie returned to their room in an awkward silence when they heard a murmur coming from the end of the hallway.

"What's that?" Charlie said.

"No idea." Ryan said and the two kept walking to find out.

As they turned the corner they saw Teddy on his knees in front of a door with his small cock still hard, dripping precum free from its cage and with Mara standing next to him with her arms crossed.

"Okay, now I'll leave you, you know what you have to do." Mara said leaving him there and going towards them with a smile on her face, "Be good."

Teddy stayed there on his knees staring at the door.

"Mrs. Laura owns my little dick, Ms. Laura owns my balls, Ms. Laura owns my orgasms." he repeated over and over again like a mantra.

Mara passed by them, her big tits were still only covered by the stickers and they bounced with every step, she winked at Ryan smiling and continued on her way.

"What is he doing?" Charlie asked her.

"My mom makes Teddy repeat those mantras in front of her door whenever she's inside fucking one of her lovers, sometimes he's there waiting for hours." said Mara giggling, "Of course, that's only if he doesn't have any tasks to do, now Teddy has a couple of free hours, later he will have to prepare everything for dinner, so for now it's mantra time."

"And no one watches him?" said Charlie, "I'm sure when you're gone he'll stop doing it."

"Oh no, no, he knows what he has to do and he wouldn't even dream of disobeying my mother, he knows what's best for him if he wants to win his prize at the end of this week." she said, laughing again, "Besides, he never knows if someone might be watching him, well I'll leave you to it, see you."

Mara left, Ryan looked at her beautiful round ass bouncing and they glanced again at Teddy who was still in his place repeating the mantra with his gaze fixed on that door before returning to their room.

"What's this about Teddy's prize?" Ryan said.

"Laura told us earlier while you were playing with your friend Mara." She said when they got to their room, "As she told us, Teddy owns several ships that work throughout the year but this one, Teddy's Cravings, is where they live and twice a year they do these types of super exclusive cruises where Laura gives him a chance to cum, but for that he has to command the staff perfectly and make sure everything runs smoothly for her guests during this week, and be a perfect good little boy the rest of the year, of course."

"That's why he seemed so anxious earlier when he told us to obey whatever Mara ordered us..." Ryan said, thinking out loud.

"Of course." she said laughing, "In the end it's up to you, boys, whether he has an orgasm or not, so...you better do everything he tells you if you want that old pervert to cum after such a long time."

Ryan remained silent, thinking about that poor man.

When they arrived at the room they heard some bangs and high-pitched screams coming from the next room.

"It seems like Amelia is teaching Hector to value their relationship." Charlie said with a chuckle.

"Poor guy, he hasn't done anything wrong." Ryan said looking at the ground.

"That's what you think because you're like him, always thinking with your tiny cock, I saw you looking at her ass just a moment ago, perv." said Charlie, "At least he has a big cock, what's your excuse?"

"I don't think only with my cock." Ryan said getting angry, "The problem is that you never let me cum and I'm obsessing over it, it's your fault."

"Oh yeah?" she said, raising an eyebrow, "So I was the one who was spying on my neighbor and stealing her underwear..."

"No...but..." Ryan said without really knowing how to answer her.

"But what?" she said, "Look Ryan, it's not me that doesn't let you cum, it's the law, for a year you can't cum, you know that, although I had thought..."

"What?" Ryan said.

"Well, I was thinking that if you behave like a very, very, very good boy this week, maybe I'll let you cum..." she said, looking at him sideways.

"Really?" he said enthusiastically.

"It's something that has crossed my mind...why do you think we haven't brought your cage?" she said with a smile, "It wasn't an accident, I'm not stupid, but it will all depend on you, at the end of the week if you deserve it I will let you cum, it will be our little secret, the SPP doesn't has to know it."

"Thank you, Charlie." He said with a big smile as another high-pitched scream echoed through the room again, "I promise, I'll be very good."

"I hope so..." she said, "Now I'm going to rest for a while." Charlie began to undress and when she was about to show her tits she stared at Ryan.

"No peeking." She said, "Why don't you go to the pool or have a drink, you still have some free time until the evening."

"Okay." He said, somewhat disappointed, looking at her, "I'm going to take a dip in the pool."

He put his swimsuit back on, grabbed his towel and went to the pool.

When he was walking down the hallway he bumped into Big Snake who seemed to be looking for something.

"Boy." He said to Ryan, "What's your friend's room?"

"Charlie?" He said.

"Yes." Big Snake said.

"It's our room and now she was going to rest for a while, it would be better if you don't bother her." Ryan said getting a little angry.

"Oh don't worry about that, I won't bother her at all." He said with a mocking smile, "Now tell me, where is your room?"

"Right there." He said pointing to his room.

He left without saying anything else and Ryan stood watching from the corner, when he got to the door he knocked a couple of times and waited in the hallway.

"What do you want? I already told you I was going to rest for a while." Ryan heard as the door opened, "Oh...hello."

"I thought you might want to know where my name comes from..." he said, still smiling in the hallway. Charlie laughed.

"Of course." she said, "Come on in, I'm looking forward to knowing everything."

She grabbed him by his shirt, shoved him forcefully into the room and slammed the door.

"Fuck." Ryan said to himself as he leaned against the wall, and just then he realized that Teddy was a few feet away from him still kneeling repeating his mantra like if Ryan wasn't even there.

When he got to the pool Lia was there sunbathing topless next to the pool.

"Hello pretty boy." She said smiling, "Isn't your girlfriend coming?"

"No, she stayed chatting with Big Snake in the room." He said, looking at her tits out of the corner of his eye while he noticed how his cock was squeezing into its cage.

"Chatting?" she said with a laugh, "You can't be so innocent."

Ryan blushed as he left his towel on a lounge chair away from her and quickly got into the pool. After swimming for a while, he leaned on the curb to rest while Lia looked at him through her sunglasses.

"Do you mind if I get in too?" she said.

"No not at all." He said.

She began to swim while he sat on the curb and watched her, then she dove in and came out a few seconds later between his legs.

"So...How are you doing so far on the cruise?" She said resting her arms on his legs smiling, her face was really close to his crotch.

"I guess I was expecting something different..." he said as she played with her fingers on his legs, getting closer and closer to the edge of his swimsuit.

"Oh yeah? Something different like what?" she said.

"I don't know, I was hoping for something more like a vacation, not being here by myself while Charlie is in our room with some guy named Big Snake." He said a little disappointed, "Besides, that whole thing about having to serve drinks while everyone else enjoys the cruise is bullshit."

"Well...I've been with Big Snake a couple of times, rest assured that Charlotte and him are going to have a long and hard...talk." She said, giggling, "Besides, you're not alone here, you have me."

She quickly pulled down his trunks until his caged cock was completely on display.

"What are you doing?" he said surprised.

"I'm giving you some love, I see you're lacking it." She said with a smile as she grabbed his balls with one hand and placed a wet kiss on them.

Ryan's cock began to throb inside its cage, no one had ever touched his balls with their mouth and she continued giving him little kisses with a giggle, enjoying his discomfort.

"Hello." said a voice behind Ryan, he quickly turned his head to see Ivy and Goo, she was only wearing a black thong and sunglasses, her beautiful tits swaying with every movement.

"Hello." Lia said, releasing his balls, "I'm leaving, I have some chores to do, we'll resume our little games another time, dear."

Ryan watched disappointed as Lia got out of the pool and followed her with his eyes as her big, beautiful ass wobbled away.

Ivy had sat on the lounge chair searching for something in her bag while Goo was waiting next to her with an umbrella.

"Where have I put it?" She said, she took out her wallet, then a keychain with four keys, a retractable metal rod..."Ah, here it is."

Then she took out the sunscreen from her bag and gave it to Goo.

"You know what to do, and don't forget any corner of my body, if my skin burns you'll be in trouble, little boy." she said, lying face down.

"Yes, Miss Ivy." said Goo, who was already eagerly pouring the cream into his hand and beginning to spread it over Ivy's back.

While Goo was pouring the cream Ryan saw how his cock was throbbing furiously inside its pink tiny cage, his little pink bow seemed to tremble and his big purple hanging balls were throbbing.

"May I ask you something?" Ryan said doubtfully.

"Of course." she said.

"What are the four keys for?" He said.

"Oh, that..." she said, taking the keychain, "This little pink key is for Goo's cage, the other three are for my ex-husbands' cages."

"And that one works?" Ryan said pointing to one of them that was completely rusted.

"No idea, I've never used it and I don't think I ever will, but I like to keep it as a cute souvenir." She said smiling, she looked at him through her sunglasses, she turned onto her back motioning for Goo to continue, "It's my first husband's, that little loser, I meet him twice a year, I let him see me in lingerie while he puts a vibrator in his cage until he cums, he doesn't deserve more than that, since we divorced he's bankrupt and my services are expensive, he's lucky that I let him see me, I think he's still in love with me, poor bastard."

"And the other two?" He said.

"With them it's different, I tie them to the bed and play with them a little, I give my second husband a handjob twice a year, sometimes I ruin his orgasm, his face of agony makes me burst out laughing. " She said, laughing, "I fuck my third husband, Goo's father, it's a pity Goo didn't inherit his father's big cock, and I even let him cum inside me. Of course, I charge them both a considerable sum for such a privilege. They have ended up becoming friends and everything, they even meet a little earlier to talk about lifes and all."

"What?" Ryan said, "Are you meeting both of them at the same time?"

"The three of them." she said with a wicked smile, "That way I do it all at once and I don't have to worry."

"And how does that work?" Ryan said.

"Easy." she said, "They book a room twice a year and when I arrive they all have to be in their positions, my first husband locked in the closet and the other two in the beds, I tie them up and start playing, usually first I fuck my third husband until he cums, while the second looks at us with frustration and envy, then I sit on my second husband's face and give him a handjob while he eats the creampie and finally, I put my underwear back on, I free my first husband from the closet and make him eat the cum of the second, I give him a vibrator and 2 minutes for him to cum, while I get dressed, don't worry about him, he doesn't usually last more than 30 seconds, I supervise him to clean everything up with his tongue and I leave him in charge of freeing the other two."

"And they have never asked you to free them?" Ryan said.

"Well...the one who protested the most is Goo's father, although he quickly got over it when I told him that if he kept going with his little tantrums I will make a place for him in the closet with the other loser, my second husband assumed years ago that this is his life now, and the first one...well, he's a complete loser." she said giggling, "Do you want to see a cool trick?"

"Okay." Ryan said a little surprised by the sudden change of topic.

She stood up and took off her thong revealing a trimmed heart-shaped bush above her pussy.

"Goo, lie on your back." she said pointing to the lounge chair, "I have a little gift for you."

He lay down and she sat on his face.

"I had have a pleasant, sweaty and hot session of crazy sex recently in my room and he came inside me, a delicacy for my Goo." she said smiling and wiggling her ass, "Look at him, he is already a horny mess."

Ryan saw that Goo's cock was throbbing hard inside its tiny pink cage, he seemed to be at the edge of cumming.

"The taste and smell of cum turns him on like a puppy in heat." she said giggling again while his little dick dripped precum everywhere.

"Alright Goo, since you've been such a good boy I'll let you cum." she said, "He hasn't cum in a looong time, my poor little creature."

Ryan was getting horny too.

"But first..." she said searching for something in her bag again until after a few seconds she pulled out a wooden spatula with some little bumps on the head and looked at Ryan with a sadistic smile, "My ball hitter. "

"You have ten seconds, don't let me look bad in front of our little friend." she said winking at Ryan. She began the countdown smiling hitting his balls with all her might with each number while Goo screamed in agony under her ass, "7, focus little boy, and remember, no cumming until I reach zero."

Goo clenched his fists tightly and moaned under her ass, while thrusting again and again into nothingness until reaching number 4 when precum began to slide slowly from the tip of his cage to his balls like a waterfall, he let out a loud moan from under Ivy's ass.

"Check it out!!" She said, laughing and began to hit even harder his blue and swollen balls even harder and faster, "It looks like his tiny dick is melting from the inside, you better hold it pervy little boy." His cock continued to throb while she kept counting and hitting his balls.

"3." She said with another loud blow with her spatula on his balls, winking at Ryan, "You're already super close to the goal, keep it up."

"2." she said smiling with another swipe, "1."

She started hitting his balls at a slow pace but still harder than before.

"Hang on kid, I haven't said the magic number yet." She said with an authoritative voice as Goo clenched her fists tightly and an indecipherable sound came from under Ivy's ass, "I've thought about it better and I'm not so sure you deserve it, what do you think Ryan?"

Ryan seemed to come out of the trance he was in when she addressed him, that was one of the hottest things he had ever seen, even he looked like he was about to cum, he felt that if someone released his cock at that moment only a slight breeze would be needed to empty his swollen balls and he knew exactly what Goo must be feeling at that moment, that boy really needed to cum.

"Well...I think he deserves it." He said with a high-pitched voice, the only one he was able to make at that moment, "I mean, look at his balls, they're so swollen and blue, they look like they're about to burst."

"That's a good point...have some mercy on my little Goo for the size of his huge balls, he must be suffering after so many months without emptying them, but it's not enough, keep holding on Goo, I haven't decided yet, we are still at 1." She said, looking at Ryan without paying the slightest of her attention to Goo who lay stiffly beneath her while his cock throbbed furiously inside his cage, "Do you have any other reason to finally let my Goo cum?"

Ryan cleared his throat, looking at her, trying not to fall hypnotized into her eyes.

"He does everything you tell him...he's a very good boy." He still couldn't get rid of that ridiculous high voice.

"But of course, he's the best of all the good little boys." she said smiling, "But that's the least asked of my Goo, don't you think so, my sweet little boy? And don't you dare to cum yet, I haven't said the last number." She stared at Ryan who remained silent, paralyzed without even being able to open his mouth.

"Well? Anything else?" she said after a long minute of silence only broken by the continuous and tremendous blows to Goo's balls.

"Eehhm..Well...I..." Ryan was trying to think of something to help Goo get his precious release, but after a while without saying anything rational she raised her hand.

"Enough." She said, gave Goo a final hard blow on his balls and got up, "I'm sorry but you're not going to cum today, your friend hasn't managed to give me a good compelling reason to let you empty those pretty, cuddly balls of yours."

Goo's face was completely red, his veins on his forehead were about to explode and his open mouth still had a drop of semen on his lower lip. He had a lost gaze directed towards the sky, his fists were clenched tightly and his cock was dripping with precum, throbbing uncontrollably inside his cage.

"Pleeeease..." he said with a small voice and with barely any strength.

Ivy gave him a tremendous blow with the spatula on his balls.

"What have I told you about speaking without my permission!" she shouted, slapping him on his balls again, "I think it's going to be a looong time until I even begin to consider letting you cum."

Goo pursed his lips and held back a moan.

"That's better. Now look at me." She grabbed her big, perfect tits in front of his face.

"Look at them." She said smiling, watching as his cock began to disappear quickly, "It looks like a little turtle hiding in its shell."

She started laughing out loud, Ryan's cock was throbbing hard in its cage watching her tits bouncing with her laughter.

"Now get up and lick your lips clean, you still have some of my gift left there." she said still with a giggle, "And what do you have to say?"

"Thank you Miss Ivy." Goo said, getting on his knees, licking his lips.

"Good boy." She said spanking his ass a couple of times with her spatula, "So, what do you think of my trick?"

She looked at Ryan with a raised eyebrow and a mischievous smile.

"Well..." he said shakily, "It seems a little extreme to me, I don't think it's for me."

"Oh, you don't think so?" She said with a bigger smile, "Well, your tiny cock loved the show, look at it all hard, trying to get out of its little cage with every throb, tiny cocks don't lie, dear."

"Look, it was hot to look at but it's not for me." Ryan said, turning red, "Also just thinking about the kind of training and suffering Goo had to undergo to get that control gives me chills."

"Suffer?" she said, "But that's the best part, all the nights I've spent molding Goo into a very good boy have been the best nights of his life, right Goo?"

"Yes, Miss Ivy." He said quickly, pursing his lips.

"Do you see it?" she said, "Honey, he's living life to the fullest."

"Now I want to read for a while." She grabbed a magazine from her bag, sat down and started reading still topless.

"Well, I think I'm going to go." Ryan said.

"Alright, see you later." Ivy said smiling, without even looking at him.

It had been almost an hour since he had left the room but he returned with some fear for what he might find when he arrived, he passed by Teddy and turned the corner of the hallway until he came face to face with Big Snake who was just coming out of the room with a big smile and walked past Ryan without even looking at him.