Small Penis Prison Ch. 30

Mia arrived early, today was a big day, finally Gina was going to leave the SPP and all the prisoners were very nervous, after 4 whole months they could have a chance to cum. She had dressed elegantly for the occasion, wearing a pale pink long split thight dress, every time she took a step her left leg was visible up to the hip, thanks to the fact that she was not wearing anything underneath.

Sif had decided to make a game to determine who would be the lucky one who could cum today, 1 boy from each girl could volunteer and would compete against the rest during 4 challenges.

"I know that you are all eager to cum but remember that during the competition you are going to suffer a lot, perhaps more than what you have suffered so far here, so think carefully before signing up because then there is no turning back and It's going to be painful and I mean terrible pain." Sif had told the entire prison the day before, "Once you have registered you will have to compete in the 4 challenges until the end."

Mia went inside the conference room that was already packed with the prisoners and sat in the first rows, reserved for the guards, in a space between Charlie and Cecilia.

"Hello girls." She said sitting down with a smile, "Are you nervous or is it just me?"

"To be honest I find all this hilarious." Cecilia said laughing.

"By the way, congratulations on the cruise to you both." said Mia, "You girls are some lucky bitches."

"Thanks!" Cecilia exclaimed, "Roro and me are going to have a lot of fun, or at least me."

"Roro?" Mia asked.

"Yes, he is my cute sweetheart." she said, "The sweetest, cutest boy I've ever met, we've been dating for almost 6 months, he's the nicest boy in the world."

"Are any of your boys competing today?" Charlie asked.

"Gene." Mia said with a laugh, "I don't think he knows what he's gotten into, poor bastard."

"Gus has volunteered from my group." Cecilia said smiling, "I practically never let him cum, he better take advantage of his chance."

"And yours?" Mia asked Charlie.

"You don't even need to ask, John is desperate to relieve his huge blue balls." Charlie said laughing, "For the first time in years he has the chance to have a real orgasm, he will do anything to take advantage of it."

"That's what I don't understand, your guys signed up because they're really desperate but Gene has cum a couple of times since he got in here, I don't know why he signed up for this madness." Mia said laughing.

"Well, he's little older than a teenager, those boys are horny 24 hours a day." Cecilia said laughing out loud.

"Yes, maybe that's why." Mia said laughing too.

Suddenly the stage curtain opened and a huge sign appeared with 'SPP Olympics' written on it.

"Welcome to the SPP Olympics." said Sif who appeared on stage as all the girls started clapping.

She was dressed in a very short and tight black dress, squeezing her huge tits that bounced with every step, leaving all the desperate boys in the room drooling.

"Please competitors, come up to the stage." Sif said.

6 men got up from their seats and began to walk onto the stage.

"Only 6?" Mia asked.

"Well, keep in mind that although the winner is going to be able to cum, he is going to have to pass several painful tests and not all guys are so brave." Charlie said with a smile, "Also some girls, like Freya, didn't allow her boys participate."

"Ohhh, poor boys." Cecilia said laughing.

The 6 boys went on stage.

Gene, Gus, John, Pete, Lenny and Theo.

"As far as I know, Kayla hasn't let Lenny cum not even once and Theo has been Cammie's pet since day one so I guess he hasn't either." Mia said.

"Those two came in at the same time as Ryan, right?" Charlie asked.

"Yeah." said Cammie who was sitting near them, "And no, Theo hasn't cum in the 8 months he's been with me, I mean, you just have to look at his big blue balls."

Mia looked at Theo, the old man's balls were blue and swollen, ready to burst, although the others were in similar condition, except Gene's, which although they were blue, did not look so swollen like the rest.

"It looks like the best have signed up, right?" Mia said, laughing, "Or at least the most desperate losers."

"Come on Petey, make me proud!" They heard Lucille shout from her seat and all the girls burst into laughter.

"Very good, now while my assistants are removing the chastity cages from these boys, I will explain to you what the 4 challenges will consist of." said Sif, "This is very simple, the winner of each challenge will gain 6 points, the second 5, the third 4, and so on, at the end of the 4 challenges the one with the most points will win, and then his guardian will give him a handjob and will let him cum, no tricks, it will be a full orgasm."

Little by little Sif's assistants were removing the boys' cages.

"The first challenge will be strength, the second intelligence, the third endurance and the fourth speed." said Sif, "The boys are ready so let's start the games!"

"If you allow me, I will be in charge of the first challenge. I'm sure that several of you would do it better than me, but let me have some fun too." Sif said with a big smile looking at the audience as she took off her dress, now wearing only a tiny black sheer thong and her black high heels, "Let's get started!"

All the girls began to applaud excitedly while the 6 boys were left alone standing on the stage with raging erections looking at Sif scared.

"Hands behind your backs, boys!" she shouted, approaching the first of the boys, John, with a seductive walk and a naughty smile.

"Hello, little Johnny boy, how long!" she said still smiling, "Are you ready?"

He nodded with a terrified expression, not knowing exactly what was going to happen until suddenly she gave him a tremendous kick in the balls that sent him to the ground.

"Get up boy!" she exclaimed, looking at him harshly.

He stood up still with an erection although with a pained face as she gently brushed his small cock with the tips of her fingers while looking at the audience.

"The first game will consist of testing the strength of their erections, as soon as their tiny cocks go limp they will be eliminated." She said, clinging to him, pressing her huge tits against his side, still rubbing his cock while he stood trembling as if he received an electric shock with each delicate touch of Sif's body.

"By the way, I'm getting a little fond of you, little boy, maybe when your sentence here is over I can accept you into my house as my caged pet, what would you say?"she said still looking at the audience with a mischievous smile.

"It would be an honor." He said stuttering as she moved her hand away from his cock.

"We'll see..." she said, still smiling, giving him a couple of slaps on his swollen blue balls, making him jump a little.

She approached the next boy, Lenny, who trembled helplessly knowing what was coming.

"What a huge pair of balls, little boy." Sif said with a laugh, "It's a shame your tiny cock isn't sized to match them."

His cock remained erect, dripping with precum and the truth is that it was a pathetic image if you compared it to his balls, Mia thought smiling.

"Finish him, girl!" a girl from the audience shouted and the rest began to laugh and applaud, encouraging Sif.

Mia looked at her, it was the first time she had seen her, she was a girl in her late twenties, with bubblegum pink hair combed in a braid, she was wearing a white crop top, a black pleated miniskirt, and knee-high black combat boots. She was very pretty, with very white skin and light blue eyes.

"Who is she?" Mia asked Charlie as the girls screamed and clapped again when Lenny received Sif's kick.

"No idea." Charlie said.

"It's the new girl." said Cecilia, "Apparently 5 more boys are coming soon and they needed another girl, her name is Nicole, yesterday I was with her showing her around the prison a little."

"And they're going to leave her alone from the beginning with the new boys?" Mia said.

"She comes from another SPP, don't worry about her, she's more than capable of controlling 5 little losers." Cecilia said smiling, "It looks to me like Freya is going to have competition."

"Destroy that loser!" Cammie shouted which made Mia look at the stage to see what was happening, just at that moment Sif unleashed a hard kick on Theo's balls.

Now it was Gene's turn.

"Come on Gene!" Mia shouted, "You can do it!"

The boy turned a little red looking at Mia and Sif took advantage of the fact that he was distracted to kick him hard in the balls.

"Poor thing..." Mia said smiling.

Mia suspected that Gene was falling in love with her, despite all the difficult times she put him through, that little boy was fascinated by her, he looked at her like a puppy in heat every time they were together.

Mia was lost in thought about adding another boy to her harem while Sif continued with the challenge.

After almost half an hour Gus was the first to lose his erection after Sif's last kick, who had already lost count.

"Loser!" Cecilia shouted, "I didn't expect you to win but being eliminated first is a shame!"

Little by little they fell one by one until only John and Pete were left.

"I think little John is going to win." Charlie said with a wicked smile.

"Why are you so sure?" Mia asked her.

"I didn't know what the challenges were going be so I put a Viagra in his breakfast to make it more fun." she said, laughing.

"You're so mean." Mia said smiling.

"Well, we're going to be here for a while then." Cecilia said laughing, "Lucille told me this morning that she was going to do the same with Petey." The three of them started laughing as they continued enjoying the show.

After a while Sif asked for a volunteer because she was getting a little tired.

"I will do it!" the pink-haired girl shouted, getting up from her seat, next to her there was a black guy, a little chubby and a couple of heads taller than her, who stood up to let her pass.

"And who is that?" Mia asked Cecilia as Nicole took the stage. "He's her boyfriend, yesterday she came with him too, he waited for her at the entrance until she finished." Cecilia said.

After almost an hour more of ballbusting, Petey's erection seemed to be starting to go down, which Sif took advantage of to stick to him and gently rub her nipples on his back while rubbing his tiny cock, which made it become completely hard again.

Mia watched as Nicole hit their balls mercilessly and without taking a break for another half hour until Petey's cock finally went limp.

"Petey!" Lucille shouted, "What a disappointment!"

"This is the classification." said Sif, "John, 6 points, Petey, 5 points, Theo 4 points, Gene 3 points, Lenny 2 points and Gus 1 point."

"Let's not waste any more time, let's move on to the next game." said Sif who had already put her dress back on, "For this we will need the help of your girls, please come up to the stage girls."

Cecilia, Mia, Charlie, Kayla, Cammie and Lucille went up to the stage laughing while the boys were tied to chairs. "

For this challenge the most important thing is intelligence, next to each chair there is a small glass, these dripping boys will have to fill their glasses with precum, we are lucky that these boys drip a lot." said Sif laughing out loud, "But there is one catch, on each glass there is a small mark, the first to reach the mark will win, but he will not be able to look at the glass during the test, he will have to decide when to stop when he thinks he has reached that mark, if he exceed the mark, he will lose, and if no one reaches the mark, the one who comes closest will win."

Mia sat next to Gene while he looked at her with puppy eyes.

"So far you're not doing bad at all little boy." Mia said as the rest of the girls sat down, "I'm so proud of you, you've withstood Sif's kicks like a champ."

"Thanks Mia." He said with a proud smile turning red.

"I want you to address me as your queen." Mia said smiling.

"Of course, my queen." he said, turning even redder.

"Good boy." she said, "You should know that that is quite an honor for you, only my true slaves call me that."

"Thanks my queen." He said.

"You're welcome, my good little boy." she said smiling.

"You may begin." said Sif, "You can do whatever you want to fill those glasses with precum, but of course no cumming."

Mia gently grabbed Gene's small cock with two fingers and began to slowly jerk him off as he moaned with each jerk. After a few seconds he was close to the edge and was beginning to drip precum, so she brought the glass closer and collected the droplets that came out of the tip of his cock.

"There's a long way to go to reach the mark, little boy." She said smiling, looking into his eyes, "We better get to work."

She began to rub faster, bringing him to the edge again in a short time, the precum fell like a small waterfall from the tip and she collected it all with the glass. Mia looked at the rest and all the girls had tried the same technique as her to make their boys release precum, except Cammie who had left the glass on the floor right under Theo's cock and was squeezing his balls tightly with one hand while she jerked him with the other making a large part of the precum fall out of the glass, and Kayla who had put on some latex gloves and while holding the glass with one hand near the tip of Lenny's tiny cock with her other hand she mercilessly penetrated his ass with a huge dildo, which made the droplets of precum slowly fall into the glass.

After half an hour Mia saw that Gene was in first place, quite close to the mark, next was Petey, then Theo surprisingly, since more precum had fallen out of the glass than in it, then John, then Gus and finally Lenny quite a bit more far off the mark than the rest.

"Maybe you should change your technique, Kayla." Cecilia said smiling.

"I'm not going to jerk this pathetic little dick, if he's last, fuck him." She said as she continued to penetrate him with force while he clenched his teeth.

"Am I close to the mark, my queen?" Gene asked with pleading eyes.

"I'm sorry little boy but I can't tell you, it's the rule." She said smiling, taking him back to the edge and bringing the glass closer to his cock for a new batch of precum.

After about 10 more minutes Gene seemed pretty confident in his chances so he asked to stop. Mia let go of his throbbing cock and picked up the little glass almost full of precum that narrowly missed the mark.

"You did great, Gene." she said, "I think you have a chance of winning, good boy."

"Thanks my queen." he said, catching his breath after the effort.

"One of the boys has already stopped and he has come very close to the mark." said Sif, "Maybe this will make the rest of the boys work harder."

Mia looked at the rest and now the one in the lead was John, who had gained momentum, his face was red while Charlie smiled, taking him to the edge again and again quickly, filling the glass drop by drop.

"I think I want to stop, Charlie." John said breathily as she quickly took him to another edge.

"You think?" Charlie said with a mischievous smile looking at the glass that had precum up close to the mark but not as close as Gene, "I can't give you clues so whatever you want, when you're sure let me know."

After a few long minutes of several edges and a few more drops John decided to stop, narrowly finishing second behind Gene.

"Not bad, little boy." said Charlie, "But you could have pushed it a little more."

"I'm sorry Charlie." he said exhausted.

"No problem, after all, it's your orgasm that's at stake." She said, slapping his balls a few times, "But I'm sure these huge balls deserve a little rest."

"Come on Gus." Cecilia said, "Get your shit together, you're making me look bad."

"I'm sorry Cecilia." He said, breathing hard, "I'm trying, I really do."

"Well, try harder." She said, instead of Charlie's fast edges she had decided to slowly jerk Gus, keeping him on the edge with a continuous flow of precum falling into the glass. Now Petey and Theo were in the lead followed closely by Gus while Lenny was still at the back at quite a distance.

Lenny looked at Kayla who, unfazed, continued penetrating his ass over and over again while droplets slowly fell from the tip of his cock every once in a while.

"Mistress?" he said with a scared face.

"What?" she said without looking at him.

"Maybe if you put a vibrator on my cock I could fill the glass faster." he said trembling.

"Don't tell me how to do my job, loser." she said without stopping, "Besides, how do you know if the glass is filling quickly or not, you can't see it."

"You're right, Mistress." he said looking defeated.

"Oops." Cammie said giggling as she covered her mouth with one hand watching the glass rolling across the floor spilling all the precum it had accumulated.

Mia saw that Cammie had, supposedly inadvertently, knocked over the glass of precum by kicking it with her foot which right now put Theo in last place.

He began to hyperventilate, looking at Cammie pleading with his eyes.

"Awww, sorry, little boy." she said with a smile, "It was unintentional, but don't worry, this isn't about who finishes first but whoever comes closest to the mark, you can still win."

She got up from the chair and went to pick up the glass, she stood in front of him and opened her legs a little to take the glass with one hand. As she did so, her tiny pink plaid miniskirt rose up, revealing her beautiful naked ass and her redhead pussy which made Theo's cock throb uncontrollably releasing a trail of precum that fell to the floor accumulating in the puddle that was already on the floor.

She continued playing with the glass for a few seconds until she got up and sat down next to Theo again, placing the glass where it was before.

"You've discovered my little secret." she said with a smile, "I'm not wearing anything under my skirt, I did it for you, little boy, I knew it would give you strength for the competition."

"Thank you, Cammie." He said half drooling, still thinking about Cammie's round ass and her pink pussy.

"You are welcome." She said, returning to her tactic of squeezing his balls hard and jerking him off slowly, "Maybe I should change tactics now that you're in last place, right?"

She began to masturbate him quickly, taking him to the edge again and again and hitting the glass a little better with all the drops that fell from his cock.

In less than 20 minutes he had already passed Lenny who was filling his glass very slowly drop by drop.

"I want to stop, Cecilia." Gus said.

"Don't fuck with me, Gus." she said, "You can hold on longer, don't be a pathetic loser."

Mia saw that Gus was in the lead right now, his glass was more or less like John's but he still hadn't gotten as close to the mark as Gene.

"Am I still far away?" he said through gritted teeth.

"I can't give you clues, idiot." Cecilia said.

"I'm sorry, Cecilia." He said, putting on a face of concentration.

Petey was very close to Gus but he looked like he was in agony, Lucille was massaging his small cock with her delicate hands with grace, keeping him on the edge from the beginning of the competition and filling the glass slowly.

Petey should have already passed the mark many minutes ago but Lucille had accidentally spilled a little of his precum in the middle of the competition but had continued as if nothing had happened.

"I want you to know, Petey, that if you win I will not only give you the best handjob of your life but I will give you my little thong so you can do whatever you want with it while you look at my sweet naked pussy." Lucille said without stopping jerking him while she slowly opened her legs revealing the turquoise thong she was wearing under her gray plaid dress, "What do you think?"