Small Penis Prison Ch 29

"Professor Pudgy is waiting for you in your dungeon, Debbie is preparing him." Kayla said.

"Pudgy?" said Freya, "I had completely forgotten."

Pudgy was one of the first slaves Freya had since she and Kayla had opened the dungeon. His real name was Pudney, he had been Freya and Sif's professor when they went to college, they had always hated him, he was a real pervert, he treated Freya terribly because her older sister had him kicked out of college for a couples of months.

He seemed obsessed with the sisters' huge tits, Freya was usually more covered up but Sif always wore scandalous cleavages which made him continually distracted during his classes. What Pudgy didn't know was that at that time Sif had the principal wrapped around her little finger, he was another pervert who she had put in chastity a few weeks after starting college, she didn't need help getting straight A's on her exams, she simply thought it was fun to have a grown man as her puppet, she had made it clear to him that if he wanted to cum from time to time he had to do everything she told him to.

Pudgy had treated Freya badly from day one because he assumed she was like his sister.

The first day he went to her dungeon, Freya had been quite surprised, she didn't know she was going to be that lucky, after the way he had treated her she destroyed him with all her rage in those first sessions, now she had turned him into a very good boy.

"So you like young girls, huh perv?" Debbie said, whipping Pudgy's ass when Freya entered the room.

Debbie was Kayla and Freya's assistant. She was a 19-year-old girl, skinny and full of tattoos and piercings. She had her hair with a red mohawk. She was always naked when she was in the dungeon. She knew she made the slaves horny.

She found it very amusing to know that everyone was gawking at her with their cocks squeezed in their tiny cages. Despite having no experience, they hired her because they saw that she had a future in the business. She was more sadistic than Freya and always came up with creative ways to torture slaves.

"How's everything going, Debbie?" Freya said.

"I was just softening this pervert up a bit for you, Lady Freya." Debbie said smiling.

Pudgy was a fat, gray-haired man of about 60 years old, he was tied to a rack in front of a wall with a huge mirror, completely naked, he had on a mechanism that Debbie had invented, his balls were tied to his head, every time he raised his head to see Debbie naked in the mirror, metal spikes dug deep into his balls causing him to scream in pain, and his ass was full of bruises and wounds from Debbie's whipping.

"Poor Pudgy." Freya said smiling, approaching him and giving him a couple of spanks, "Those horrible spikes are hurting your huge blue balls, don't they, little boy?"

"Yes, Lady Freya." He said almost crying from the pain.

"I have a surprise for you, Pudgy." she said, "Today I'll let you cum."

"Yeah?" He said deeply surprised, "Thank you very much, Lady Freya, I really need it."

"I know, I know." she said, "How long has it been?"

"8 months and 24 days." he said trembling.

Despite all the pain his little cock was hard as a rock.

"Ooooh, that's a lot for my poor little Pudgy." she said, "Debbie, you can go."

Freya approached a wall where several strapons were hanging.

"But first you'll let me play with your ass for a while, won't you, my good little Pudgy?" she said picking up one about 12 inches, "Deep down I know you love it."

"Yes, Lady Freya." He said, raising his head a little to see her.

Freya smiled as she saw him moan in pain as he raised his head to look at her in the mirror, she knew that he was completely obsessed with her tits and he was going to love her huge cleavage, those balls were going to suffer like hell today.

"I know the most I've ever fucked you with is 10 inches but I think you're ready for 12, don't you think Pudgy?" She said moving closer to his ass.

"I suppose so...Lady Freya." he said trembling with fear, lowering his head again.

"I don't like when you put yourself down, Pudgy." she said, starting to penetrate him with her huge dildo, "Like that time you said you couldn't handle 100 kicks in the balls and in the end you held on like a champ, I know you can do it, take it like a man."

Little by little she inserted the strapon into his ass until with a gasp it disappeared completely.

"Look at that!" she said, laughing, "I knew you could take it."

She began to thrust again and again while he moaned between pain and pleasure, slowly at first but gradually increasing the speed.

"Look at me, Pudgy." she said, "I want you to watch me while I rape your ass."

He raised his head with effort as the spikes dug into his balls to see how her tits bounced in her corset with each thrust.

Freya fucked his ass for half an hour, forcing him to raise his head every few seconds.

"I think thats enough." She said pulling the strapon out of his ass with a loud 'Plop', "Now I'm going to let you cum."

She took off the strapon and approached him again with a vibrator in her hand.

"Don't cum until I say so, Pudgy." She said putting the vibrator on his cock while turning it on at low intensity.

"Yes, Lady Freya." He said.

Within seconds he was dripping precum.

"Looks like you're close, aren't you little boy?" she said.

"Yes, Lady Freya." He said.

"Your ass has been left completely open." she said, laughing, "I think my whole hand would fit inside."

She began to insert her fingers one by one into his ass until almost effortlessly she had her hand inside.

"Look!" she said, laughing, "I knew it."

"I'm going to cum Lady Freya!" he exclaimed, as she quickly moved the vibrator away.

"Not so fast." she said, "Let's play a game."

She pulled down her corset, leaving her huge tits on display.

"I know that you are obsessed with my beautiful tits and I have never let you see them, so I have decided that I am going to give you a prize today for being such a good boy." she said as he tried to lift his head, "Don't lift your head until I tell you!"

"Sorry Lady Freya." He said looking at the ground again.

"It's a very simple game, right now if you lift your head you would see my tits in all their glory, what we will do is this, when you are about to cum you can lift your head and see them but I will move the vibrator away and ruin your orgasm, or you can continue looking at the floor and having a complete orgasm, your choice." She said with a mischievous smile as she put the vibrator back on, turning up the intensity a little.

The man looked at the ground trembling, indecisively weighing his options.

"What a dilemma, huh little boy?" she said, laughing, "Seeing my huge beautiful tits for the first and maybe only time or having that full orgasm you've been desperately wanting for so long."

"I'm at the edge Lady Freya." He said.

"What will it be then, Pudgy?" She said, increasing the intensity of the vibrator.

After a few seconds Pudgy couldn't take it anymore.

"I'm cumming!" he exclaimed, quickly raising his head as the spikes dug into his balls and Freya put the vibrator away with a naughty smile, looking into his eyes, raising an eyebrow.

"I knew it, little boy." she said still looking into his eyes while his cock dripped cum, throbbing in the air pathetically.

Pudgy stared at her tits as if seeing for the first time the most beautiful thing made by nature as he gritted his teeth through the devastating pain in his balls and the agony of a frustratingly ruined orgasm.

"All the pathetic little dick boys like you would do anything only for ten seconds of my naked tits, even if it means ruining his long awaited orgasm." she said smiling and covering her tits again, "I hope you enjoyed it, loser."

"Thank you Lady Freya." He said without taking his eyes off her tits, his small cock still dripping cum, making a small puddle on the floor.

"Debbie!" she shouted.

A few seconds later Debbie appeared through the door.

"I'm done with him." Freya said, giving her the vibrator, "Untie him, put his little dick back in the cage and make him lick that disgusting puddle he made until the floor is shiny."

"Of course, Lady Freya." she said.

"But first slap those balls a few times, the sight of my beautiful tits cannot go unpunished." Freya said.

"Your wish is my command, Lady Freya." she said with a mischievous smile grabbing his balls hard and beginning to punch them with all her strength while he sreamed in agony.

"I said slaps, Debbie...nah, nevermind, keep going." Freya said stopping at the door with a big smile, "And you, little loser, in a few months we will play the same game again, although I am sure it will end in a similar way, it seems to me that only ruined orgasms await you in the future, or maybe not, it all depends on how obsessed you are with my amazing huge tits."

She closed the door as Debbie's punches and Pudgy's desperate screams echoed through the hallway.

When she arrived at the SPP, Sif told her to go with her to Olivia's office. Charlie, Cecilia and Olivia were there along with another girl that she didn't know.

"Hello Freya." Olivia said, "This is Lia."

"Hi, nice to meet you." Lia said with a smile.

She was a black woman in her late 30s, she was quite pretty, she had long straight black hair, and was wearing a gray top and matching leggings, she looked like she was dressed to go to the gym, she had small tits and a flat toned stomach but what caught the eye was her huge round ass.

"As I was saying, I work for a cruise company, Sky Adventures." she said with a smile, "For about 10 years we have been working with the SPP and we raffle among their workers a free week on our cruise, 'Teddy's cravings'."

"And Charlie and I won!" Cecilia exclaimed, laughing.

"Yes." said Lia, "As I was telling you, you can bring a companion, whoever you want, the only requirement is that if it is a man, he has to wear a chastity belt during the entire trip, without exceptions."

"Cool." Charlie said laughing, "Can I go with Ryan?"

"Yes of course." Olivia said.

"And what do I have to do with all this?" Freya asked Sif.

"Since they are going to go on that cruise for a week, you and I will take care of their boys, is that okay?" Sif said with a smile.

"No problem." said Freya, "When are they leaving?"

"Next week." Sif said, "By the way, it's your turn with Samuel, I'm sure he misses you."

"I'm sure he does." Freya said as she and Sif laughed.

When Freya got to the door she heard some banging and moaning, she opened the door slowly and saw Cammie fucking Samuel's ass mercilessly with a huge strapon while squeezing his blue balls hard.

"Where have I seen this before?" she said laughing, "By the way, sorry for interrupting."

"No problem." Cammie said, "It's your turn already?"

"Yes, it's my turn." Freya said looking at Samuel.

He was completely naked, only wearing an inverted chastity cage and a black hood that covered his head, with one hole for his mouth and two for his eyes, and a ballgag.

"Time flies when you're having a good time, doesn't it loser?" Cammie said smiling as she pulled the strapon out of his ass.

Freya looked at the large blackboard on the wall, it was Olivia's idea, it was divided into the days of the week and each day was divided into 8 plots, each girl put her name and what she had done with Samuel, at the end of every Sunday everything was erased and every Monday they started from scratch.

Today Freya was the fourth, the first had been Charlie, she had written 'Edging' then it was Lucille, 'Edging + Asslicking', then Cammie who just at that moment was approaching the board to write 'Strapon'.

"What am I going to do with you, loser?" said Freya thinking out loud, "I know, a little ballbusting won't hurt you at all."

Samuel began to make muffled screams, knowing what the near future held for him.

He was tied to a rack with his legs spread, leaving his huge blue balls completely exposed.

"Have fun." Cammie said laughing as she left the cell.

"I will." said Freya laughing, "Are you ready? It's going to be an hour, nothing more, you don't have to worry."

Then she kicked him tremendously in the balls while he screamed uncontrollably.

"Don't complain, that was one of the weak ones." She said, laughing again as she prepared to give a new kick, stronger than the previous one, "Besides, after me comes my sister, I'm sure she will be much more lenient with you."