Small Penis Prison Ch. 09

"I'm exhausted." Gina said sitting down in her sister Lena's office.

"A hard day at the office?" Lena said looking at the computer screen with a half smile on her face.

"You know so." Gina said, "The days when new prisoners arrive are always like that, the preparations, the presentations, the check-ups..." she said, snorting.

Lena was Gina's little sister, a little taller and a little thinner but they looked alike. Lena was married and had two children, although she had her husband in chastity, they had a fairly conventional marriage.

Gina was also married although their marriage was far from conventional.

Poor Roger, her husband, was lucky if she paid him any attention between her continual affairs. She had met him in prison when she was a guard, he was there for 1 year for a minor thing.

Gina ran a business outside of prison as a keyholder, men paying her large sums of money to keep their chastity keys. In addition to the monthly payment, they also paid her a fortune for each hour of session, she tied them up and then played with their cocks. She then decided whether or not to let them cum, most of the time with little luck for the boys.

It should be said that many of his clients were ex-convicts of the SPP.

Roger had been one of her clients when he got out of prison, after a while she had grown fond of him, and after repeatedly asking him to marry her, she had ended up accepting, with certain conditions.

They had been married for 5 years, time flies, she thought.

"Freya wanted to see you." Lena said.

"Why?" Gina asked.

"I have no idea." Lena replied, still looking at the computer.

While Gina ran the prison, Lena handled all the administrative paperwork.

"Well I'll go talk to her and then I'll go home." Gina said.

"Don't forget the gimp." Lena said.

"Oh it's true!" she exclaimed.

The gimp, as they called him, was Benjamin Coulson, a prisoner who had rebelled as soon as he arrived at the prison, they had sent him with Freya but not even she had been able to straighten him out, so they had kept him in isolation for 3 years.

Gina saw him 3 times a day to feed him and Lena took him out to the patio every morning for half an hour to stretch his legs a bit.

Gina left the office on her way to meet Freya.

She entered Freya's room, Freya was in the middle of the room with a man in front of her tied to a cross.

The man was wearing a gag other than that he was completely naked with a flat chastity cage, his balls were big and full with bruises and wounds. In his eyes was a mixture of terror and pain.

There were 4 other guys around the two of them, all tied to chairs with similar chastity cages and their balls in a similar state.

"It's only 30, you have 70 left and we'll be done with the exercises before going to bed." she said with a sadistic smile.

Freya was a short Asian girl about 5 feet tall at most, she was skinny but she had huge tits that caught the eye. His pink hair was cropped on one side and the rest was down to his shoulders. She was wearing a miniskirt and a black leather corset, the corset made her breasts spill out on all sides, leaving her with a huge cleavage. She was wearing thigh-high black metal-tipped boots.

Then she kicked the man tied to the cross in the balls with full force.

"31" she said as the man yelled under the gag.

"32" she said after another devastating kick, her huge tits bouncing endlessly with each kick.

"Ahem!" Gina said when she was already on kick 38, trying to get Freya's attention.

Freya turned around and looked at her.

"Oh, sorry Gina, I didn't hear you come in." Freya said, "We'll continue later!" She said to the man on the cross.

"Don't worry." Gina said, "I heard you wanted to talk to me."

"Yeah, it's a silly thing." she said timidly.

Gina was always struck by the fact that Freya was a ruthless sadist at work but was so shy outside.

"What is it?" Gina asked.

"It's for your party tomorrow, I wanted to know if I could bring someone with me." she asked in a small voice.

"Of course!" Gina exclaimed, "Was that it?"

"Yeah." she said looking at the ground.

"Of course you can bring a companion." Gina said, "Someone set you up?" she asked smiling.

"Something like that." Freya said smiling shyly.

"Well I have to go, I still have to pay the gimp a visit before I go home." Gina said, "I'll leave you, I see you're busy. Bye."

"See you tomorrow!" Freya said as she turned around to go back to the man on the cross.

"I'm sorry but I forgot where we were going." Freya said, "We'll start over."

The man screamed in despair under the gag.

"1" Gina heard as she closed the door after a violent kick.

She went to prepare the gimp's dinner in the prison kitchens, it was the usual, a flavorless nutritious paste with a splash of liquid Viagra and one of the pills she gave Charlie for little John and a glass of water.

The door to the gimp's cell was down the hall.

She entered the room, it was dark. When she turned on the light, she saw the man lying on top of a blanket on the floor.

It was a small, square white room with no windows, there was only a blanket on the floor and a stretcher attached to one of the walls.

The man on top of the blanket had his hands tied behind his back and a neck strap attached to the wall, he wore a leather hood on his head with holes for his eyes and a small hole in his mouth with a rubber tube inside.

As soon as Gina turned on the light the man began to tremble and looked up at her. He began to make unintelligible noises, nothing could be understood due to the tube in his mouth.

"Sssshhh...I'm here little boy." she said in a loving tone, "How is my Benny?"

The man was completely naked except for his chastity cage and hood. Under the cage he had a very small black leather bag that squeezed his balls, at most a couple of inches in diameter.

"I bring you your dinner." she said approaching him.

She grabbed him by the head and began to release the paste down the tube.

Then she emptied the glass of water and spat into the tube.

"Swallow it all like a big boy." she said smiling as he swallowed it, "That's it, good boy."

Then she helped him up and laid him on the stretcher after releasing the neck strap. She released her hands to tie them to the sides of the stretcher, then tied her feet as well.

"Perfect!" she exclaimed, "Now let's start stretching before going to sleep."

She unzipped her dress exposing her big tits that overflowed in her red bra and took the key that hung between her large breasts, the man looked at her desperately while he moaned through the tube.

Gina opened her chastity cage and the leather bag of her balls while the gimp screamed in pain.

As soon as she opened it his cock was already rock hard, throbbing, leaking precum, very red and with cage marks, his balls were huge and purple, at least 4 times bigger than the little bag where they were confined.

"That's better, isn't it, little pervert?" she said with a giggle.

The man was sweating, despite the suffering he couldn't stop looking at her big tits.

"You like my tits, huh?" she said as she brought them slowly up to her face.

"Do you like my new perfume?" she asked while her tits brushed against the hood, the man made some desperate sound but she couldn't understand with the tube in his mouth.

"I guess the answer is yes..." she said sensually looking into his eyes.

The man had bloodshot eyes, he looked like a zombie who only thinks of one thing, cum.

"Look at your little thing raising and shaking as if greeting me..." she said smiling.

"Hello little dick!" she waved, "Have you missed me?"

"But you've seen me at lunchtime?...you love me too much, I don't deserve you." she said bringing her mouth to his cock.

"A little kiss." and she brought her mouth to within an inch of his cock and gave him an air kiss.

She exhaled into his cock with a moan.

His cock throbbed as precum dripped from the tip.

"Does it seem bigger or is it me?" she wondered.

She brought her face closer to his cock again.

"No, you still have a tiny dick like always, sorry." she said pouting. "But hey, your balls are huge, you should be proud!" she exclaimed laughing.

"Now let's play for a little while." she said approaching his face and giving him a little kiss on the hood.

She began to stroke his cock very gently with the tips of her fingers. His cock danced from one side to the other, it seemed that a light breeze would make him come.

Then she made a circle with his index finger and thumb and she gave him an extremely slow stroke from top to bottom.

The man moaned and began to shake, his cock throbbing and he began to gush precum.

"With that alone, are you already on the edge?" she said with a laugh, "Sometimes I'm surprised at your lack of stamina."

She waited a few seconds for him to calm down and she did the same thing very slowly, taking him back to the edge.

It went on like this for half an hour or so, the man just a whimpering thing unable to think straight.

"Good boy." she said after getting him to the edge for the umpteenth time, "Now we're going to put you back in your cage."

The man gasped into the hood. He began to speak, to plead, to scream, all to no avail.

She went away from the stretcher and came back with his cage and the little leather bag for his balls.

Despite the small size of his cock, with how hard it was it was going to be impossible to get it into the cage.

Gina grabbed him by the balls and began slapping him hard to make his erection go down, with each slap the man screamed under the hood, she knew that with the viagra she had given him it would be impossible for his erection to disappear but he didn't.

"I'll have to hit you harder because it doesn't seem to be working." She said looking into his eyes with a smile.

Then the loud slaps turned into devastating punches.

The man screamed in agony. After 10 minutes like this his cock was still rock hard.

"Well, it will have to be by force." she said snorting.

Then she took the chastity cage and began to put it on, after several minutes and many cries of pain from the man, his cock was squeezed inside the cage.

"Now your big balls, that's going to be more complicated, I think." she said.

She grabbed his balls and squeezed them into the bag.

The man was screaming inconsolably, high-pitched screams muffled by the hood.

Considering only one of his balls was bigger than the little bag it was going to be a tough job for Gina.

Little by little, ball by ball, Gina was able to put his balls in the bag, but not before hearing the man's howls of pain.

In the end his balls were crushed and squeezed in the bag.

"Okay, now to bed." she said releasing his hands and feet.

The man was dizzy with pain.

She tied his arms behind his back and the wall strap around her neck.

She slipped her hands under her black dress and removed her lace red thong leaving it coiled in the tube.

"That's it, have sweet dreams Benny." she said with an affectionate voice as she sent him another kiss through the air.

She turned off the light and closed the door, listening to his cries as she walked down the hall.

Gina sat in Lena's office.

"How's the gimp?" Lena asked.

"As usual." Gina said, "With his stiff dripping cock and his huge balls." and burst out laughing.

"Sometimes I feel sorry for the poor boy, don't you?" Lena asked.

"No, he deserves all of this and more." she said very seriously.

"Why did they put him in prison?" Lena asked, "I don't remember."

"From what I remember, he spent years harassing a poor girl, sneaking into her apartment, calling her at all hours and things like that, he was obsessed, there came a point where the girl was very scared." Gina said.

"When they caught him they ended up sentencing him to 15 years in prison." Gina said, "Although he always denied all the charges, that's why he made such a fuss the first day and that's why he's been in solitary ever since."

"Maybe he's already reformed and behaves like a good boy." Lena said.

"We will know it in 12 years when his sentence is over, until then he will continue in his little cell." Gina replied laughing.

"Ok, you're the boss." Lena said, "By the way tomorrow I'm going to your party alone, Mike is staying with the kids at home."

"OK no problem." Gina said, "Now I'm going home." She said getting up from the chair.

"See you tomorrow, Lena" Gina said.

"Bye Gina" Lena replied.

In half an hour Gina was already parking her car in the garage of her house.

"Roger!" she yelled, "I'm home!"

Roger suddenly appeared and knelt in front of her, completely naked except for his flat chastity cage.

He was a short man about 5'2 feet tall, Gina next to him in heels looked gigantic at almost 6 feet tall.

"Good evening, my Queen." He said.

"How is my little boy?" she asked.

"Very good, my queen" he replied.

"Glad to hear it." she said, "Manny is coming to dinner today, have you got everything ready?"

"Yes, my Queen." He said.

"Perfect, come with me, I want you to help me choose what to wear." she said going to the room.

Manny had been a professional basketball player, retired a couple of years ago.

He was a white, blond man, 7'1 feet tall, very muscular, and with a huge cock.

Gina had been seeing him regularly for about 8 months.

Roger hated him, he was everything he wasn't and he was so jealous when he came regularly to fuck Gina while he slept in the guest room.

"Wait here while I shower." Gina ordered.

Roger waited on his knees in front of the bed.

Gina emerged from the bathroom 20 minutes later wearing only a white silk robe, completely naked underneath. The robe ended above the thigh.

"I'm going to wear white underwear, it makes me look virginal, don't you think?" she said with a seductive smile.

"Yes my Queen." he replied.

"Turn around." she ordered.

Despite having been married for a few years, Roger only had the pleasure of seeing Gina naked on rare and precious occasions.

Roger felt how his small cock was squeezed in its cage trying to get hard while he listened to Gina behind him and imagined her perfect naked body.

"Perfect!" she said, "You can turn around now."

Roger turned around and his cock nearly burst the cage at the sight of her in a bra and thong. She was wearing a semi-sheer white bra and thong that hinted at her nipples and gave a glimpse of her pubic hair. The bra squeezed her tits that practically overflowed.

"How does it fit me?" she asked raising an eyebrow.

She turned around to show the back, her big beautiful ass a joy to behold for Roger.

"Impressive, you are like a goddess, my queen." he said almost drooling.

"Thank you dear!" She said, giving him a kiss on the forehead, when doing so her tits wobbled in front of his eyes, which almost caused an explosion in his cage.

"If you behave well today, maybe tomorrow I'll let you cum." she said smiling.

"Thank you, my queen" he said very eagerly, he hadn't cum for more than a month, she only released him from his cage once a week to clean his cock and shave him and for the sessions of more than two hours on Saturday nights in which she edged him repeatedly to cage him again without letting him cum.

His balls ached all the time and his cock kept dripping with precum.

"I have three outfits to try, I bought them yesterday, tell me which one you like best." she said taking them out of the closet.

The first was a pink summer dress with a knee-length skirt, it cut her neckline quite low and left her back bare.

"What about this one?" she asked turning around.

"Very good, my queen." He said.

"I don't know, let's go for the next one." She said taking it off and leaving it on the bed.

Next was a fitted dark blue dress with a V-neckline that fell to just above her knees. It highlighted her curves and made her an incredible ass.

"I like this a lot but I don't know." she said hesitantly, "Let's go for the last one."

"I think this one looks better on me without a bra, so turn around." she ordered.

He waited with his back to her as she put on the last dress.

"You can watch now." she said after a few minutes.

He turned around and her heart sank, his hard, raging cock squashed inside its cage.

The last dress was black in one piece, it had two straps that joined at the nape of her neck and went down to her waist, covering little more than her nipples, causing her huge tight tits to overflow from the sides of the straps, at her waist they were joined with a gold brooch with an open, floor-length, flared skirt that left her legs bare from her waist to her high black heels.

"I think we have a winner, don't you?" she said smiling turning around.

As she did so, her skirt rose, showing that she had also removed her thong.

"Yyy-yes, my queen." he stammered as his clenched cock almost reached the edge and he released a trickle of precum.

"Perfect." she said smiling, "Now go get everything ready before Manny gets here."

She waited in the living room having a glass of wine while Roger left everything ready.

"Very well, now to sleep." she said, "Sweet dreams dear!" she said giving him a little kiss on the forehead.

Roger went into the guest room and left the door half open so he could listen. It was torture to listen to how another man fucked his wife but at the same time it turned him on too much.

He was dying of jealousy thinking of another man impaling her, something he had never done, not with her or with any other woman, but that was something Gina had made very clear when they got engaged, he would remain a virgin for her.

When Manny arrived Gina put her arms around him and gave him a passionate kiss.

"I've missed you darling." she said, "You and this huge cock." she whispered in his ear as she stroked his cock through his pants.

"Oh yeah?" said he, "Prove it!"

She bent down, pulled his cock out of his pants and began to suck him sensually.

"I've also missed that mouth, nobody sucks my cock like you do, you have a gift!" he said with his eyes rolling.

"Thanks love!" she said licking his balls.

"Do you want to have dinner before?" she asked, "Roger has been up all afternoon getting everything ready."

"No, I am not hungry." he said, "Let's go to the bedroom."

"Whatever you want." She said grabbing his cock and leading him to her room.

"I'm going to fuck your ass so hard you won't even be able to walk tomorrow!" he said giving her a hard slap on her ass.

"You better..." she said smiling.

Roger was listening to everything from his room with envy with his rock hard cock inside his cage.

They reached the bedroom and she pushed Manny onto the bed. She got on her knees on the bed and began to suck his cock.

His cock was hard and veiny.

She sucked it from top to bottom, slowly putting it down her throat while she played with his balls with one hand. She started going faster and faster.

She kept going like that for a few minutes until he was about to cum.

"I'm going to cum, baby!" he exclaimed.

She went a little faster.

"Oh fuck, I'm cumming!" He exclaimed with his eyes rolling, grabbing her head and pulling her down, thrusting his entire cock into her as he came.

She swallowed it all smiling.

"Now we go for the second round." she said winking at him.

She got on top of him cowgirl style and began to slowly go up and down with his cock inside her with her dress still on.

"Oh my God!" she exclaimed, "I'm in love with your huge cock!"

She increased the pace and in a few minutes she was moaning very loudly with her first orgasm.

Then she got out of bed and seductively took off her dress, looking into his eyes.

Her large breasts bounced as she jumped on the bed.