Small Penis Prison Ch. 31

Gina arrived at the SPP door walking slowly with Roger by her hand.

"Are you nervous?" Roger asked her.

Gina looked at him with a smile, Roger was such a sweet boy and she loved him a lot, in her own way of course.

"A little bit." She told him, despite having been working here for years, the fact that today was her last day made her tremendously nervous, "Let's go in."

Gina came in squeezing Roger's hand tightly and all her girls were there.

"SURPRISE!!" they all shouted in unison.

Charlie and Sif brought her a white cake with a candle on top.

"Thank you very much girls." She said still holding onto Roger's hand tightly.

"Blow the candle!" Charlie said.

She blew hard and they all applauded. After almost an hour Gina had already spoken to almost everyone and was chatting with Charlie.

"Girl, you really look stunning." Charlie said.

"Thank you so much." she told her.

Gina had put on a very short and tight transparent black dress, which left nothing to the imagination, her big tits were overflowing and gave her an impressive cleavage.

"You could let Roger go a little, you've had him on from the beginning and the poor boy follows you everywhere like a lapdog." Charlie whispered to her.

Gina had been holding Roger's hand from the beginning without realizing it. He was dressed in a black tuxedo that she had bought him for the occasion.

"Roger, if you act like a good boy today, I'll let you cum tonight." she had told him before leaving the house.

"Oh, sorry Roger, dear." She said, letting go of his hand, "Where is Mia? I haven't seen her yet."

"Well, she must be with Gene, she went to give him his reward for winning the competition, she loves playing with that boy, I think she's getting too attached to that boy...."

"Did Gene win?" she said.

"Yes, it's a long story but in the end Gene won." Charlie said smiling.

"Tell me about it while we go look for her." Gina said.

Charlie told her how the competition had been and when they arrived at Mia's room they were both laughing out loud. They opened the door and saw Mia on the bed, sitting on Gene's face completely naked while he licked her ass relentlessly.

"Mia, you missed Gina's surprise." Charlie said still laughing.

Mia looked up while still gently rubbing Gene's cock with one of her hands.

"Sorry Gina, I'm giving Gene his reward and you know, time flies..." Mia said smiling.

"Don't worry." Gina said with a smile.

"Well, you two must have been here for more than an hour and a half." Charlie said.

Gene started moaning under Mia's ass and Mia slowly released his cock.

"How many has been already, little boy?" Mia said lifting her ass off his face.

"39, my queen." he said catching his breath.

His little cock was red and raging, bouncing and throbbing, he had left the sheets all wet under his balls from all the precum dripping from the tip.

"I think that's enough." she said, "Are you ready for your reward?"

"Yes, please, my queen, I am ready, please." he said trembling.

"Do you think he's ready?" Mia said, slowly rubbing his cock and sitting on his face again, "The other 39 times I asked him he didn't seem desperate enough."

"It seems pretty desperate to me." Gina said smiling.

"Yes, let him cum once and for all and come to the party." Charlie said.

"I don't know." Mia said looking at his cock that was throbbing again, she slowed down the pace even more and a few seconds later muffled screams were heard again under Mia's ass.

"Hang in there, little boy, don't even think about cumming yet." She said as she went on to rub his frenulum very gently with her index finger.

After more than a minute of muffled screams Mia let go of his cock and watched as it throbbed hard.

"Okay, I'll let you cum." She said with a smile, grabbing his cock tightly and slowly jerking him off again, although faster than before, in a few seconds the muffled screams began again, "Cum for me, my good little boy."

Mia kept jerking him off and put her other hand in front of his cock as Gene began to convulse. Suddenly his cock began to shoot jets of cum and Mia caught it all in her hand quite skillfully. After a while he finally stopped cumming.

"That is a lot of cum, I think it's the biggest load I've ever seen in my life." Mia said laughing as she showed his cum on her hand to the girls.

"Roger shoots bigger loads than that on the rare occasions I let him." Gina said.

"Maybe one day we should have a competition between the two of them..." Mia said smiling, she stood up and showed her cum filled hand to Gene.

"Now drink it all." Mia said emptying her hand into his mouth, "That's it, very good boy."

Mia got dressed again and went with them to the party, leaving Gene tied to the bed with his cock still hard.

After two hours of party Gina and Roger were opening the door to their house and Roger immediately began to undress.

"What are you doing?" she said.

"Undressing." He said looking at her confused.

"Stop it." she said, "I think you look gorgeous like that, let me enjoy such a handsome boy."

He looked at her with puppy eyes.

"Of course, your wishes are orders." He said.

"Good boy." she said, "For such a special night, I just hope everything is perfect, and you being so handsome in your tuxedo is the icing on the cake."

"Thank you, my queen." he said turning a little red.

"A night of unbridled sex awaits us, dear." she said smiling, "I hope you're ready."

"Are we going to fuck?" he asked with a mix of surprise and excitement.

Gina let out a laugh.

"You and I?" she asked still laughing, "Of course not, silly boy, after all these years I thought we were over all that."

"I thought maybe, since it was a special night..." he said, visibly disappointed.

"And it will be a very special night, dear." she said, "Don't be disappointed, I promise, if you behave I will let you cum all over my big, beautiful tits, it has been a long time since I have allowed you such an honor."

"Yes, I'll be very good, I promise." He said all excited again, although there was a certain desperation in his voice.

Gina smiled, Roger had not cum for many months, the frustration must have been practically unbearable.

"By the way, I have a little favor to ask you." she said.

"Anything for you, my queen." he said with a smile.

"Good boy." She said, "You see today a new friend of mine is coming to dinner and I need you to behave like a true gentleman, will you do it for me?"

"Of course." He said.

"The thing is that I met Nate a little over a month ago at a friends' party, and he is a very special man, a true gentleman, funny, intelligent and on top of that a body to die for." she said, "We met up a couple of times but he isn't into all that cuckolding stuff so I didn't tell him I was married, so today you'll have to be like my butler, you don't mind, right?"

"But..." he began to say.

"No buts, remember you said you'd be good, you don't feel like cumming on my tits, then?" She said, gently pinching one of her nipples over her dress while looking into his eyes.

"Yes, I will be your butler." he said, looking down.

"Great!" she said.

"And what do I have to do?" he asked.

"Do everything I tell you and it will be fine." she said, "Where's Holly?"

"I think she's in her room." he said, "I thought I heard some noises as I passed through the hallway."

"You wouldn't be stalking her again, would you?" Gina asked, Roger was trying to hide it but Gina knew that he was gawking at Holly all the time, although her always going half naked around the house didn't help.

"No, no, I promise." He said.

"Alright, I'm going to talk to her." Gina said going to her room.

When she opened the door, Gina saw Holly in front of her bed, dancing in a very sexy way, wearing a very tight T-shirt and a white thong, her huge tits without a bra bouncing from one side to the other, she was wearing large headphones and she hadn't noticed Gina was watching her from the door.

"Holly!" she exclaimed.

Gina looked at the bed and saw a man of about 50 years old with his hands and legs tied to the bed sitting with some pillows behind his back looking very excited at Holly, his mouth was covered with duct tape and he was covered with a quilt up to the waist. Then he saw Gina and his eyes widened.

"Milton, Milton, Milton." She said looking at him, "I didn't expect this at all, I'm very disappointed."

"Aunty, I thought it would take you longer to get home." said Holly who had already taken off her headphones.

"Well, you see, we've already arrived." Gina said looking at her, "What's all this?"

Holly looked at her with a good girl smile.

"You mean Milton and I?" she said as if playing dumb.

"Yes." said Gina, already starting to get angry, "Are you fucking him? He hasn't cum in more than 6 months and you go and fuck him?"

Holly laughed.

"Of course not." she said, "You know I have a soft spot for older men, but real men, not small-dicked losers like Milty."

"And what are you doing?" Gina said.

"Ok, relax, let me explain it to you, a couple of weeks ago I went to see my sister at your office, while I was there the receptionist had to leave for a moment and asked me if I could replace her for an hour, I accepted and during the entire time no one called until just before she arrived, Milty called." Holly said, "He told me he had been trying to contact you but you hadn't answered his calls so he was calling there to make an appointment."

Gina looked at her waiting to see how this whole story would end.

"I told him that you weren't there but if he wanted he could have an appointment with me for 3,000 dollars." she said, "He said no, so I asked for his phone number and told him I would call him in a moment."

"How loyal!" Gina said looking at Milton with a tone full of sarcasm.

"Then I took a selfie and sent it to him asking him if I was hot enough for him." Holly said with a smile, "It didn't take him a minute to call me and in less than half an hour we were both in a hotel room, we bathed together in the hot tub, I was wearing my cute tiny pink bikini, remember that Milty?"

He stared at them with a mixture of perplexity and embarrassment.

"And you let him cum?" Gina said, "You don't have the key."

"No, that time we just played a little, I gave him a looong massage on his poor swollen blue balls, you are so cruel with him, aunty, to leave a boy as good as Milty for so long without cumming..." Holly said, pouting, looking with her big blue eyes at Milton, "So the least I could do was relieve a little of all the pain and frustration accumulated in his huge, full balls. That massage felt amazing, didn't it, Milty?"

"Yes, Miss Holly." He said looking at her enthralled.

"So I promised him I'd let him cum for me for $10,000 on our next date." Holly said looking at her aunt again, "And here we are."

"And you stole my keys?" Gina asked now, visibly angry.

"No, no, who do you take me for?" said Holly, "Milty was soooo disappointed when he found out I didn't have the keys, he was so desperate that he offered me 10,000 more if I would look for them all over the house, but I told him no, I would never betray my dear aunty."

Holly approached Milton as he followed her with his unblinking gaze and she lowered the covers, revealing a vibrator strapped to her chastity cage, vibrating at the lowest intensity.

His cock tried to grow inside its tiny cage without success and throbbed again and again dripping precum onto his huge blue balls as she ripped the tape from his mouth with a quick tug.

"I tied one of my favorite little toys to his cage and promised him I would dance for him until he came." She said, sitting on the bed next to him while she got her mouth close to his ear and pressed herself against him, rubbing one of her big tits against his chest, "But the poor little boy still hasn't cum after more than half an hour, maybe I'm not pretty enough for you, is that it, Milty?"

"No, no, you are the most beautiful girl I have ever seen." He said, closing his eyes tightly as she began to rub his balls gently with her hand.

"So what is it?" She whispered, "Aren't you as desperate as you said?"

"Yes, I promise, I need to cum, please let me cum." He said, moaning as she squeezed his balls a little, "Maybe if you turned up the intensity a little..."

"Oooooh, so that's what it was..." she said, bringing her hand closer to the vibrator, "I left it like this because I wanted you to enjoy the experience as much as possible, but don't worry, now I'll turn it up a little."

Then she turned it up to maximum power and Milton let out a loud moan, he looked like he was about to cum.

"Stop!" Gina said looking at them, "Holly turn that off!"

Holly quickly turned off the vibrator, looking at her aunt with a smile like a naughty girl who had been caught misbehaving, while Milton let out a small cry of despair.

"Milton, forget about cumming for a long time, this is the last straw, you tried to cum in front of me, without my permission, you are a very, very bad boy, Milton, you will be severely punished..." She said, looking into his eyes, while the man looked at her terrified, "As for you, young lady, we'll talk later, now untie him and let him go."

"At your service!" Holly said, jumping out of bed.

"And please, change your clothes, I'm having guests today." Gina said closing the door as she left the room.

Gina went to the living room and sat on the couch, still a little angry.

"Roger, be a sweetheart and bring me a glass of wine, quick!" she said.

Roger quickly appeared with the wine glass in his hand and she drank it in one gulp. What was happening to her? She was nervous about her date with Nate like she was a schoolgirl waiting to be picked up to go to the prom.

In less than an hour Roger had finished preparing dinner when someone knocked on the door.

"It's him." Gina said to Roger, "I hope you behave, don't let me down little boy, do what I told you and everything will be fine, now go open the door."

Roger went to open the door and a few seconds later he appeared with Nate in the living room.

"Mrs. Gina, your guest has arrived." Roger said.

"Alright Roger, you can leave." she said with a smile, "Nate, dear, what a joy to behold."

"Gina, you look great." He said smiling, looking at her cleavage without hiding it.

She was still dressed in the same black transparent dress from the afternoon, after all she had worn it for Nate, he was her retirement gift, she thought, smiling.

He was dressed in a black suit and tie, very elegant, Gina looked at him for a while appreciating his athletic body, he had been a professional basketball player like Manny and they were friends.

Nate was a couple of heads taller than her hubby, that added to his muscular body made Roger look more like a little boy than ever.

"What would you like to drink?" Gina asked motioning for him to sit next to her on the couch.

"A glass of white wine, please." he said smiling.

"Roger, bring another glass of wine." She said, watching as Roger appeared with the glass and bottle and served them both.

"So you have a butler?" he said, "Manny didn't tell me any of that."

"Yes, Roger has been with me for several years, he is a very helpful boy." She said smiling as she put her hand on Nate's leg just as Holly entered the room.

"Hi!" she said with a big smile, "You must be Nate.".

"This is my niece Holly." Gina said looking at her, she had put on a bright yellow dress, with a great cleavage that had nothing to envy of Gina's.

"What a beautiful girl, it seems that you have very good genes in your family, nice to meet you." He said taking her hand and kissing it.

"Oh, what a wonderful man." Holly said smiling, "Roger bring me another glass of wine."

After chatting for a while, they went to the dining room and began to dinner. Roger served them like a real butler, Gina thought he was doing a great job, if everything went well he really deserved a reward at the end of the night.

"So you're dating my aunt?" Holly said just as they finished the dessert.

"Well, I would say that we are just getting to know each other at the moment, but she is a wonderful woman, that's for sure." He said looking Gina in the eyes with a smile.

"She is more than ready for you to take the next step in your relationship." Holly said winking at him with a naughty smile.

"Leave it Holly." Gina said, turning a little red, "Why don't we go to the living room to continue with the evening?"

"Of course." he said getting up.

They sat down while Roger refilled their glasses.

"So how long have you had a butler?" he asked.

"Roger?" She said looking at Roger, Why is he asking me about him again? she thought, "For several years now, I think I've already told you."

"Well, as I told you, Manny never told me anything about a butler, what he did mention was that you had a husband." He said staring into her eyes still with a smile on his face.

Gina took a long sip from the glass, thinking how to get out of this mess.

"Okay, I'll be honest, Roger is my husband." She said looking at Roger and then at Nate waiting for his reaction.

"I know." He said, "I guess you know that I'm not really into the whole cuckolding thing, I understand that's why you've tried to hide it." he said, sipping calmly from his glass of wine.

Shit, my whole plan is falling apart, Gina thought.

"Why not?" she said.

"Well, maybe you can say that I'm a little traditional, but I like having a relationship with a woman, without other men having sex with her, even if he is her cuckold, I don't feel comfortable knowing that she is not just for me, it's like she is cheating on me with him." he said taking another sip.

Gina laughed.

"Don't worry about Roger, we don't have sex, we never have and we never will." she said, looking at Roger, "Isn't it, my good little boy? Tell him"

"Yes, Gina." He said, turning red, looking at the ground, "We never had sex."

"Never?" He said surprised, "And how does your relationship work?"

"Well, he worships me like a goddess and in return I let him play with his little thing from time to time, I control when, how and if he cums at all." Gina said laughing, "Don't get me wrong, I love him a lot, but only a measly handjob is enough for him, that little dick is pathetic, it doesn't deserve more than that, let him see it, honey."

"What?" He said, visibly red.

"Get naked, now." She said looking into his eyes. He undressed until he was completely naked with only his chastity cage.

"Oh my god, he has one of those things." said Nate, "I've never seen one in person."

"Yes, and I have the only key, he can't do anything without my permission." she said.

"Do you jerk him off?" He said looking at her, "I'm not very comfortable with that either, to be honest."

"I mean, it's a handjob, nothing fancy, do you care that much?" She said looking at Roger and then at Nate.

"I don't like it." He said, "But, hey, it's your lifestyle and I respect it, don't get me wrong, it just doesn't suit me."

"Well, what if he did it himself would you be okay with that?" she said looking at Roger.

"Yes, of course, I'm not heartless, I know what it feels like when you need to cum, the poor man will need relief from time to time." he said laughing, "But he's okay with that?"

"Of course." She said looking at Roger, "No problem at all, tell him, Roger."

Roger was red with rage, Gina knew perfectly well what was going through his mind, they were taking away the little pleasure he had in his life right under his nose and without a second thought.

"No, no problem." he said through gritted teeth.

"Like I said." she said, "Roger is a very good boy, he knows his place, he won't give you any problems, don't worry."