Author's Note
This is my story for the Kinktober 8rd writing prompt, and the fetish of the day is imprisonment. The writing prompt is written in cursive, with my writing continuing the story in regular text. As always, comments are appreciated, and I hope you enjoy the story! 
Busted And Arrested
--It didn't work anymore. Nothing he did worked anymore. He'd been trying all the old stuff for over a week now, and he'd never felt more frustrated and unsatisfied. He'd tried everything! The basement, the attic. Tartarus, he'd even used his closet. It still didn't give him the feeling he wanted, not anymore.
With a sigh he plopped his rear onto a street bench and just watched the other ponies walk by, going about their day, as he brooded. He bet no other ponies had to go through this, he was certain he was the odd one out when it came to his fellow ponies. He wished he had something that could make him feel it once again.
A flash of gold and a loud cry caught his attention and drew his gaze. It was a beautiful mare in a Canterlot guard uniform restraining a pickpocket. He felt a bit jealous of that pickpocket. He got to have a mare all over him before he got take... And and idea clicked into place. His eyes followed the mare guard as she led the pickpocket away and were out of his sight before he started to quickly make his way home to prepare. He never noticed the wide, almost manic smile on his face. He would finally get satisfaction. Tonight.--
Upper East Stride spent the day coming up with the perfect plan - not to get away with crime, but to get arrested by a sexy guardsmare. This was not a trivial matter as most of the guards were stallions, but he could think of one place that should be off limits for them; The royal bathhouse. Of course that meant getting in wasn’t going to be too easy either, but that would only make his quick arrest all the more likely. He rubbed his hooves together, giddy with anticipation and feeling like a true mastermind about to set his plans into motion.
As the night fell, he walked casually past the bathhouse entrance to check it one more time. As expected, the front entrance was guarded by two sexy mares in golden armor, looking firmly straight ahead. He stepped behind a corner and put on a ski mask. He knew he didn’t need it for identity protection, but oh boy did it make him look suspicious! He could hardly believe his luck when he noticed an open ventilation window right on the unguarded side of the building.
It took him some trouble to actually climb through the small opening, but with a great deal of effort and determination he managed to squeeze himself inside. He fell in through the window, landing on a pile of cleaning supplies and making a ton of noise in the progress. ”Okay, time for stealth is over!” he thought to himself, throwing the supply room’s door open and dashing out for the most exhilarating chase of his life.
”EEK! Intruder!” an upper class mare screamed, covering herself with a towel as Stride dashed past her. He grinned at the sight but kept running, not satisfied until he’d be caught by a real, uniformed guard. No rules, no safewords, this time he was going to be a mares captive for real! He made it through two more rooms with mares in various states of undress, before bursting into a hallway and coming face to face with a tall, purple unicorn in golden armor.
”Stop right there criminal scum!” Commander Tempest shouted, but Upper East Stride was already bolting away from her. He wanted her to chase him, to pin him down, and to truly take away his freedom like no mare had done before. His cock was already starting to peek from his sheath as he prepared to get tackled from behind.
Instead of a tackle, his escape was halted by a mind-shattering kick to the balls. His eyes bulged as Tempest delivered a spinning kick right between his legs, crushing his sack against his pelvis with enough force to send him tumbling over with a filly-like scream. The sudden explosion of pain made him curl up instantly, his vision filled with stars as he tried to deal with the nauseating agony emanating from his groin. Before he could gain his bearings, a strong, feminine hoof rolled him onto his back, followed by another stomping down right onto his freshly kicked balls.
”GYAAAH!” he yelled, his eyes shooting open in an instant. Commander Tempest was standing over him, her rear hoof firmly planted on his ballsack as she calmly reached for a pair of hoofcuffs on her hip. He was frozen by pain, watching and whimpering as she clipped the hoofcuffs around his forelegs before finally lifting her weight from his agonized nutsack. She made no effort to stop him from curling up to soothe his aching balls, while she addressed the two guardmares running in to check the commotion.
”The intruder has been arrested. Take him outside while I alert the princess.” she commanded. The guardmares saluted her before grabbing Stride by his armpits and starting to drag him away.
He groaned in pain, his rear legs dragging behind as he attempted to keep them apart to give his throbbing sack some much needed breathing room. The unbearable pain had knocked all thoughts from his mind for a while, but now his situation was starting to dawn to him again. He was hoofcuffed, and tightly in the grip of two strong mares. There was no escape. Even without the hoofcuffs just one of them was probably trained enough to subdue him, especially so after Tempest had stomped his nuts into an aching mess. Considering how efficiently she had immobilized him by his balls was actually turning him on even more.
The guards dragged him outside, where a small cart with a cage had been brought for him. The mares unceremoniously tossed him inside and slammed the door shut, leaving him crumpled on the floor with his nuts in his hooves. Lucky for him, they didn’t see his smile, nor his growing erection as he relished in his confinement. He started slowly stroking himself, careful to keep his back towards the guards to keep his activities secret. He wanted to savor every moment of this, feeling about to cum from the sense of confinement alone.
He was still edging himself when the words of one of the guardmares snapped him out of it. ”Get ready, the princess will be here any minute!” His eyes snapped open as he realized that he was about to face the princess with his cock still out at full mast, trying to desperately think of a way out. To his dismay there was no escape, which only served to turn him on even more.
”Sweet Celestia, he has a boner!” one of the guards gasped. He blushed hard, feeling completely trapped with his predicament.
”Oh no no no, we can’t let Celestia see him like this!” another one said, trotting in place nervously.
”Take it easy, I think I can handle it!” the first guard said, more to calm her friend than out of confidence. ”Hey you! Scoot over here!” she said to Stride, gesturing towards the edge of the cage.
He was blushing like no tomorrow, but the cat was already out of the bag and out for all to see. With his erection bobbing around, he shuffled to the edge of the cage, pushing his rear legs between the bars to get closer to the mare staring at him with urgent expression. Before he could ask what she had in mind, she grabbed one of his legs and pulled hard, yanking him balls first against the bar of the cage.
”GAAH!” he yelled, his left nut squashed between his pelvis and the iron bar. Still holding his leg, the guardsmare allowed him to back away and give his balls some room, while his friend got the idea and grabbed him by his other leg. ”AARGH!” he yelled again as they both pulled simultaneously, slamming his aching nuts against the metal pole once again. ”GYAAH!” he cried as the mares pulled him into the bar one more time, his nuts squashed against the bar like he had fallen legs wide on top of it. His bruised balls were in excruciating pain, but even as he fell over half unconscious, he couldn’t help being aroused by his helplessnes in the hooves of his captors.
”...We can’t keep delaying her any longer! It’s been ten minutes already!” one of the guardsmares said, audibly exasperated. He had been too busy dealing with his nut pain to pay attention to anything else for a good while.
”I’m out of excuses too, but he’s just not going soft! We have to let her see him no matter what!” the other one said with resignation.
At that moment, a very irritated Celestia walked out of the bathhouse with Commander Tempest by her side. The two guardsponies bowed down to her as she approached the cage.
”Allright then. Now that I’m finally here-” her eyebrows lifted as she saw Upper East Stride trying to bow down deep enough to hide his erection. His blush got even deeper as he realized he wasn’t fooling anypony.
”I-I’m sorry princess...” he muttered in apology.
Celestia’s expression softened as she saw his embarrassment. ”Apology accepted-” she said with a soft chuckle ”-mister... Upper East Stride?” she finished, surprising herself as she recognized him. ”What are you doing here?”
Stride opened his mouth to speak, but quickly realized that telling the truth might not be in his interest. If she knew he wanted to be imprisoned, she would no doubt use something else to punish him instead. ”Peeking.” he lied.
Celestia narrowed he eyes. ”Oh really?” she asked, staring at him inquisitively. He gulped nervously, sweating bullets as he tried to desperately think of something to substantiate his story. After watching him stew in his nervousness for a while, Celestia turned to Tempest instead. ”Check him for a changeling disguise.” she commanded.
Before Stride could react, Celestia’s magical aura surrounded his handcuffs, lifting him upright with his forehooves in the air. He wondered how Tempest was supposed to use any kind of detection magic with her broken horn, until she stepped forward and pointed it directly at his aching ballsack. His eyes grew wide with fear, but before he could draw breath to protest it was already too late. A powerful stream of electricity shot forth from her horn, electrocuting his balls with searing intensity. He screamed and trashed wildly, his balls aching like they were about to explode as the constant stream of lightning danced over them . His erection was bouncing around between the bars as his tortured groin finally reached the point of overstimulation - the captivity, humiliation and pain driving him over the edge into the most powerful orgasm of his life. With a half crazed scream, his cock erupted like never before, shooting massive load after load all over the two surprised mares.
Tempest cut her lightning stream short as the first sticky splash landed across her face. Celestia could only gasp as another long squirt of jizz sprayed her from chin to horn, clenching her eyes shut as Stride’s abused balls kept unloading all over her.
His screams slowly faded into moans, his whole body clenching as each squirt forced their way through his rock hard erection. After what felt like eternity, his shaft started softening as his squirts finally dried out into a dribble. Celestia, her coat and mane now matted with semen, could only stare at the spent stallion with her eyes wide and mouth agape. There was a long, awkward silence before anypony could say anything.
”Well.” Celestia said as she gently lowered Stride onto his knees. ”I guess you were just a little pervert after all.” she concluded. One of the guardsmares ran inside, returning quickly with towels for the two cum-soaked mares. They took a while to wipe some of his semen off their faces, giving him some much needed time for recovery while they concluded that they were going to need another full bath right away.
Stride was still in a haze of post-orgasmic haze and post-ballbusting agony, resting his forehead against the bars with his throbbing balls in his hooves. Celestia levitated her cum-soaked towel back to the guardsmare before finally giving him her verdict. ”As far as crimes go, this was pretty harmless. A night in jail should be enough of a lesson - especially since you seem to have suffered enough already.” she said with a giggle.
He watched with mouth agape as Celestia started turning around, surprised by her lenient sentencing. Thinking fast, he grabbed the bars and shouted after her as loud as his pained breath allowed.
”Your flank was too fat anyway!”
Faster than eye could see, the alicorn’s rear hoof shot between the bars, hitting his swollen nuts like a cannonball. He screamed in agony as her golden horseshoe squashed his balls into pancakes, the excess force throwing him against the back wall of the cage. He flopped down like a wet rag, screaming his lungs out at the incomprehensible levels of pain radiating from his utterly demolished balls.
”Make that a month in the dungeon.” Celestia said bluntly as she lowered her leg and continued her way to the bathhouse. ”I’ll make sure to visit him before his sentence is over.”
Stride was struggling to breathe, his stomach churning like he was about to puke his nuts out. But it was going to be worth it - as for the next thirty days he would be literally forced to live out his greatest fetish. Just the way he liked it.
The End
