Small Penis Prison Ch 32

Ryan was very tired, the day before Charlie had been teasing and edging him for hours, all for Hannah's stupid page, what bothered him the most was that in the 4 months that he had been out of the SPP Charlie had not let him see her naked even once, that killed him.

Of course, Charlie had banned him access to porn and he couldn't even watch his own videos.

He hadn't realized how much control she had over his phone until one day when he was watching a video on YouTube and a lingerie ad popped up, the girl was gorgeous, with a killer body and the face of an angel, she was so pretty that she seemed from another world, he visited the advertising page and started seeing photos of the girl, in less than 5 minutes a message from Charlie popped up on the screen.

"Are you sure this is what you want to see, little boy?" She had written to him, "Leave that page immediately if you don't want to be punished."

Ryan quickly left the page and went back to watching YouTube videos. Since then he had not seen anything remotely sexual, just in case, it had been a very hard 4 months and it did not look like his situation was going to get better, quite the opposite.

"As soon as you finish your session at the SPP, come home, don't worry about your luggage, I'll take care of everything." Charlie had told him before leaving, "Don't be late."

"Stupid cruise..." he said to himself, "The last thing I need is to see a bunch of girls in bikinis, it's going to be real torture."

He arrived at the SPP at 9 in the morning, and went straight to the usual room.

Ryan had asked Charlie to talk to Laurie, to tell her that she was the one who freed him from his cage every afternoon, she had told him that she had already done it but she only told her that they would have to study his case, this was the fourth time he had come to her sessions since Jo had retired and the sessions with Sif were a real torture, edging and ballbusting for 3 hours with Sif was a total nightmare.

Ryan got naked and sat in the chair and waited for Sif to arrive, after a few minutes the door opened, to his surprise it was Laurie with a very young girl, she couldn't have been more than 20 years old.

"Hello Ryan." Laurie said.

"Hello." He said getting a little flushed.

"This is Tammie." she said.

"Hello." Tammie said, she had olive skin, long dark brown hair and black eyes, she was dressed in a white shirt and a black pleated miniskirt and high heels, she was a little shorter than Laurie, with a very cute face although she seemed a little shy.

After a fleeting glance Ryan couldn't take his eyes off Tammie's big breasts, they had nothing to envy of Sif's.

"Tammie will take care of you from now on, she'll be Jo's replacement." said Laurie, "I hope you guys get along, well, I'll leave you alone now, I have something to do, I'll be back in a couple of hours."

"It's your first time?" Ryan said smiling, trying to relax the atmosphere a little.

"Yeah." She said, smiling back, "I'm a little nervous, I hope you don't mind."

"No not at all." He said much more relaxed, now that he would no longer have his sessions with Sif his future looked much brighter.

"Perfect." she said, "Now I'm going to tie you up, it's protocol, don't move, please."

"Of course." He said with a smile, if he played his cards right this could even be fun. She got on her knees in front of him and his eyes were glued to her cleavage while she tied him up, his cock trying to grow inside its cage, despite so many months locked in chastity, he still hadn't gotten used to the pain of his cock when it get hard inside its tiny cage and winced a little in pain.

"Does it hurt a lot?" She asked after tying his hands when she noticed his grimace.

"The cage?" he asked.

"No, I meant the rope." She said, looking away shyly, she was sooo cute, he thought.

"Oh no, not at all." he said with a smile.

"And the cage bothers you a lot?" she asked emboldened.

"Sometimes...but don't worry, I'm getting used to it little by little." he lied with a smile.

"It must be really hard..." she said, "I've seen a lot of guys in chastity and it seems like it hurts a lot, but you seem to handle it very well."

"Yes, I'm a grown man, this is nothing." He said trying to pretend, although he felt a little ridiculous.

"I see...a big grown man..." she said smiling as she finished tying him.

"And how does such a young girl dedicate herself to this?" he asked.

"Well, I just graduated from SPP school." she said proudly, "The first of my class."

"Excellent!" he exclaimed, although he had no idea what that was.

"Right now I'm on trial, but if everything goes well I think I'll be able to keep this position and who knows if I'll be promoted in the future." she said.

"Good luck with that." He said, "And what does your job consist of, apart from these sessions with me."

"Well, apart from you there are 12 other guys who are also on probation and I have to do these same sessions with them, make reports and give them to Laurie." she said.

"12?" He said amazed, "It seems like a lot, can you handle all that on your own?"

"No problem." she said, "Especially if they're as good boys as you."

Now he was flushing again, such a young girl calling him a good boy.

"My girlfriend works here." He said, calling Charlie his girlfriend was a big fat lie but Tammie didn't know that, "She's a guardian."

"Oh yeah?" she said, standing up, "I also thought about that job but in the end I changed my mind."

She approached the backpack that she had left on the table and after searching, she approached him with a key in her hand.

"Here it was!" she exclaimed excited.

She freed him from the cage and his cock immediately became erect, then she took off her shirt and left it on the table and Ryan was left gawking at her tits.

"Just in case." she said winking at him, "You can't cum but I've seen plenty of boys like you have little accidents..."

She was wearing a white lace bra and her big tits were spilling out everywhere, she had a little mole on her left breast and Ryan couldn't take his eyes off it.

"I thought the session would be more of an interview like Jo did..." Ryan said, worried again.

"Oh no, it will be edging, it clearly says that on your file, Lurie's rules." she said with a smile.

"But..." he said.

"No buts." She said, kneeling in front of him, "I know what you thought as soon as you saw me, with this young girl I will have everything much easier, don't you, little boy?"

"No, no, I just don't think all this is necessary, really." He said trying to sound calm.

"I know that you think so, but Laurie thinks otherwise and she's my boss, so it'll be edging and ballbusting, and that's it." she said, "And don't let my looks fool you, I've edged more cocks, hit more balls and ruined more orgasms than you can imagine, this isn't my first rodeo, you're under my control now, and if you're a good boy maybe I'll give you my little thong at the end of the session, deal?"

"That would be great..." he said, flushing again, after all this frustration he has become a total pervert, he thought.

"That's what I thought, all of you little dicks boys tend to be perverts and you are no exception." she said laughing, "Now let's get started, shall we?"

She gently grabbed his cock and began to slowly rub it until in less than half a minute he was on the edge.

"Wow." she exclaimed, laughing, "When I saw your file I was excited to meet you, I have never played with a boy who hasn't cum for as long as you, your huge blue balls were the first thing that caught my attention but I didn't expect such a lack of stamina."

"I'm sorry." was the only thing Ryan could think of to say.

"Oooh you truly are a very good boy..." she said smiling, "There's nothing to apologize for, most boys like you have little stamina, well, enough chitchat, let's keep playing."

She grabbed his cock with her soft hand and in a few seconds he was back on the edge.

"This session is going to be very long if my mere touch brings you to the edge." she said with a mischievous smile, "I think I have a solution."

Then she grabbed him hard by the balls and started slapping them hard.

"Better not?" she said between slaps.

She didn't hit as hard as Sif but after almost 5 minutes of slapping, his balls hurt like hell.

"I think that's enough." she said, winking at him, "Let's play with this little boy again."

She jerked him off again and he was now able to hold out for a little longer.

"You see?" she said, "Sometimes a little heavy-handedness is the best solution."

In a few minutes he was on the edge again and she slapped his balls again for almost 5 minutes, at a slow but sure pace.

"So Charlotte's your girlfriend, huh?" She said, raising an eyebrow as she went back to jerking him off again.

"Y-Yes." he said trying to concentrate.

"Liar..." she said, laughing, "I've already told you that I've read your file, I know who Charlotte is, who you are, where you live, everything I need to know is in your file, you don't need to make up any kind of story in which you end up being a big macho man, I won't believe it, plus seeing your tiny cock is enough to get to know you better."

"Maybe she's not my girlfriend right now, but in the future she will be, you'll see." Ryan said a little angrily.

"Oh yeah?" she said laughing out loud, "Let me tell you something, and I'm going to be very honest with you, maybe in the future she will be your girlfriend but don't think for a second that you will be anything more than her cuckold, with a little dick like yours, she will fuck real men day in and day out, while you will jerk off at home, alone, thinking about your beautiful girlfriend being pounded by cocks 4 or 5 times bigger than your little thing, and that's if you're lucky, If it were me, I would lock your cock in a cage and throw the keys into the ocean."

"I don't think so." He said, although deep down it seemed like a pretty likely scenario, "At least she would be nicer to me than you think."

"Maybe you're right, I wouldn't really throw your keys into the sea, I love playing with tiny cocks too much." she said, laughing again, "I have to tell you that you look a little like my boyfriend, he has a much bigger cock than yours but physically you look a lot alike, maybe that's why you awaken in me a kind streak that I don't usually show to others pervs like you."

She continued jerking him off and slapping his balls until Laurie opened the door.

"How are you doing?" she said with a smile.

"We got along very well, he is a very good boy." said Tammie, "Isn't that right, Ryan?"

"Yes." He said half distracted while she kept jerking him, he had already lost count of how many edges she had.

"That's great!" Laurie said, "Now finish up, we have to go, we have a date in 1 hour with another guy."

"OK." Tammie said getting up, "I'll lock him in his cage and we can go."

While Laurie was writing something down on her notebook Tammie stood looking into Ryan's eyes, he couldn't take his eyes off her big breasts in her bra.

"Now we're going to have to get this down somehow..." she said with a mischievous smile, "Do you have any ideas?"

"Maybe with some ice it will go down quickly." he said nervously.

"Yeah, I guess so." she said still smiling, "Is there any ice around here, Laurie?"

"No, but don't bother so much, punch him in the balls and in no time his erection will go down, that's what Sif always does." she said just as she closed the notebook, "I'll wait for you outside, don't be too long, please."

Laurie left the room and Ryan stared at Tammie who had a strange smile on her face.

"Do you know what I liked most about my classes at SPP?" she said, looking him in the eyes, "When they brought some of the prisoners to us to practice ballbusting, it was hilarious, the poor boys screamed and cried non-stop, but screw them, they were the only ones to blame for being there, their perverted impulses had led them to prison, so I don't feel sorry for them."

She kept looking into his eyes until suddenly, without flinching, she kicked him hard in the balls. Ryan let out a sharp cry of pain, that kick had taken him by surprise.

"Ssshhh." She said softly, placing her index finger on his lips, "You don't need to make so much noise, little boy."

Ryan could only stare at her deep cleavage while she continued leaning with her finger over his mouth.

She stood looking at him again.

"I know." she said, "I promised you my thong if you behaved."

She put her hands under her skirt and slowly took off her thong.

"Do you want it?" She said raising an eyebrow, holding her thong with two fingers, it was pink with little white hearts.

"Yes." He said looking at her intently.

"Open your mouth." She said, as soon as he opened his mouth she quickly shoved the thong into him, "You may notice a funny taste, my boyfriend came inside me just this morning, but I'm sure you don't mind."

And suddenly she unleashed another tremendous kick on his balls, Ryan couldn't stand the pain and let out a scream muffled by the thong.

"That's better." she said winking again at him.

After about 10 minutes of ballbusting Tammie finally put his cage on him.

"We're done." she said, getting dressed, "It wasn't that bad, was it?"

Ryan couldn't even speak, the sessions with Tammie weren't going to be much better than Sif's. After untying him and letting him get dressed, the two of them went out and at the exit they met Laurie and a man.

The man was Kevin, another inmate, Ryan had seen him several times, he seemed a little angry.

"Have they released you?" Ryan said.

"Something like that." he said through gritted teeth.

"I don't know why you're so angry, if you've lost 2 whole inches it's solely your fault." said Laurie, "Anyway, don't worry, you won't use it too much."

"What are you talking about?" He said.

"As I already told you, your dick will be locked in a cage and only I will have the key, you will take care of my house and Tarek, you will be my cuckold." She said, "I'll only let you free when I feel like it, and even though I've forgiven you, I haven't forgotten everything I've been through because of you, so I hope your tiny cock is cozy crammed in there because it's not going to come out to play in a looong time."

"But..." Kevin said a little confused.

"No buts, let's go, we're in a hurry." She said,

"Ryan, Tammie is going to come to the next sessions alone, I've seen that you get along very well and everything has gone perfect, so there's no need for me to come."

They said goodbye and Ryan headed home.

When Ryan got home Charlie was ready to leave, she was wearing a black fishnet sarong, a black micro bikini, and some jean shorts with the thong straps showing on the sides.

"Do you like it?" She said with a smile putting on some big sunglasses, "What do you say?"

"Yes, yes, amazing." Ryan said with his mouth wide open and his cock getting as hard as possible inside its little cage.

"I thought I'd get...where is it?" she said thinking, "Oh, I know."

She turned around and bent over, leaving her perfect ass in her shorts in plain view, and began rummaging through a small pile of clothes on the floor.

"It has to be around here..." she muttered.

Ryan stood there staring at her ass, studying every curve, the two straps of the black thong that were increasingly visible, the cleft of her buttocks, the seam of the shorts that cut her ass in two right by her asshole and those two little mountains that outlined her beautiful camel toe, Ryan was about to explode but he couldn't stop looking at such a work of art.

"Here it is!" she exclaimed, standing up suddenly with a hat.

"Better?" She said, putting on her hat, covering her hair except for the two blond braids that hung down to her shoulders.

"Yes, you are perfect." He said without thinking too much, still with the image of her ass in his mind.

"Oooh, you are such a sweetheart." she said smiling, "I have a surprise for you."

"A surprise?" He said confused, Charlie's surprises usually ended up with him in some very frustrating situation, with his cock dripping and his balls even bluer than before.

"Yes, take off your pants and underwear." She said looking him in the eyes, "Now."

He took off his clothes quickly.

"Good boy." She said, taking off her key necklace that she carried everywhere, crouching down and opening his cage in one quick motion, "I don't think you're going to need this on the cruise."

"What?" He said surprised and very excited, "Don't I have to wear the cage during the cruise?"

"Exactly. That's what I said." she said, standing up with a sweet smile, "Besides, I think you deserve it, a vacation after so much teasing, edging, torment and agony, it's the least your little cock deserves, I think you could use a rest, don't you?"

"Thank you very much Charlie." He said, his heart began to pound, "You're the best, I'm sure it'll be good for you to get a break from me too, right?"

"Ooh no, no, no, I love being with you, you're a sweetheart, the truth is that I think I have became a little fond of you, Ryan, do you feel the same?" She said smiling at him with a hint of shyness.

"Yes, I've felt the same way about you for a long time, you know that." He said.

"I know." she said, "But I didn't know if after what you're going through you would have changed your mind."

"Of course not, my feelings are the same, if not stronger." he said, his heart beating wildly.

"What a sweet boy." She said, approaching him and giving him a wet kiss, putting her tongue in his mouth and playing with his very gently.

Ryan almost came, his cock was throbbing like crazy just inches from his flat stomach, he was practically on the edge, he was in paradise, kissing Charlie, his Charlie, the most perfect girl in the world, was a dream come true.

"Thank you." He said with his eyes closed.

"You're welcome, it has been a pleasure." She said with a seductive smile winking at him, "Now be a good boy and grab those two little suitcases, we're leaving now."

Those 'two little suitcases' were two huge suitcases that weighed a ton each.

They arrived at the cruise ship and Cecilia was already waiting for them with a man in his thirties and a woman in her fifties. Ryan noticed the woman, she was a very attractive lady with long blonde hair, quite jeweled and dressed in a gray dress that highlighted her voluptuous curves.

"Hello." Charlie said.

"Hi guys." Cecilia said, she was wearing a white one-piece swimsuit, a leopard print sarong, her hair afro and sunglasses, "This is my Ronnie and his mother, Mrs. Candy."

Ronnie greeted them with a slight nod and a small shy smile.

"Good morning." said the lady smiling.

"Babe! We're in a hurry!" said a man waiting leaning on a black sports car near them.

"Yes, mom, hurry up." said a guy in his twenties.

"Don't be like that, I'm saying goodbye to your brother." she said, giving Ronnie a kiss on the cheek.

"That's your brother?" Charlie asked.

The man was nothing like Ronnie, he was a very good looking guy, black hair, hot body and looked full of himself while Ronnie was a shy little boy and quite ugly, Ryan thought.

"Yes, they are brothers, my poor Ronnie had the bad luck to inherit his father's bad genes, scrawny, half bald, short and worst of all, a tiny penis and a wanker, not like Lars, his little brother, tall and athletic, and if we talk about his penis, 3 times bigger than Ronnie's, my poor thing, but he has other attributes, he is a very sweet and disciplined boy."

Ronnie was flushing.

"Well, my sweet boy, I'm going to miss you, have a good time." She said giving him another kiss on the cheek.

"Bye, Mom!" He said still very red.

"Forget about it, darling, you're perfect to me." Cecilia said, hugging him and giving him a kiss on his forehead, "Let's have a good time!"