A sea of red and crimson from the rays of the ongoing twilight hung above Canterlot. A sign that the day was coming to an end and the nightlife was about to begin.

The door to one of the many luxurious restaurants opened, and a classy, clean-cut earth pony stallion strode inside with a cocksure gait. With his gray, well-trimmed coat perfectly contrasting with his white mane, and cutie mark in the form of mirrored shades on his flank, he was oozing suave charm.

“Well, well, if it isn’t Mr. Stylish,” Lucky, the unicorn bartender, said. “What will it be, Dapper? The usual?”

“Nah, today, I want the most expensive whiskey you have.”

Lucky smiled, levitating the bottle and already predicting to come home with a generous tip. “Here you go,” he sent full glass towards his customer. “So, I get it, you earned a lot of cash again?”

Dapper smirked. “As I always say, there is no shortage of gullible, stupid mares.”

“Anypony important?”

Dapper took another sip from the glass and chuckled. “Hrmph, she was like the rest of them, trying to threaten me with friends, princesses, and even prison. And for what? She willingly gave me that money, after all. Stupid whorse...”

“Always playing innocent, huh?”

“Hey, not my fault that I have a charm that stupid mares fall for!” Dapper protested with a purposely over-dramatic tone, quickly followed by a crafty smile. “The compromising photos and movies I take are just insurance.”

They both let out an ironic chuckle, and for a moment, began talking about other things. It wasn’t until Dapper’s glass was almost dry when a female voice filled the air.

“A glass of margarita, please, with three ice cubes.”

“Coming right up, ma’am.”

In the corner of his left eye, Dapper could see a classy white unicorn mare with a curled violet mane. Her azure eyes locked on a sketchbook.

“Here you go, ma’am,” Lucky said, passing the drink to the mare.

“Thank you,” the mare said, levitating a sack filled with bits onto the bar. It was enough money to drink till morning. “Keep the change.”

Luck’s eyes widened up in disbelief. “Thank you, ma’am!”

“Name is Rarity, darling.”

“Of course, Miss Rarity! If you need anything, just give me a holler.”

Rarity answered with a nod and levitating her drink, quickly returned her attention to the sketchbook.

Well, well. Gorgeous and rich, huh? Dapper couldn’t let that chance pass him by. “Excuse me, madam, may I ask what such a beautiful mare like you, doing in the place like this?”

“Trying to find inspiration for my work,” Rarity said with irritation, quickly followed by a sigh of resignation. “Not having much luck. So, if you don’t mind—”

“Is that a sketch of a… tuxedo?” The inquiring tilt of Rarity’s head was a dead giveaway that Dapper’s words got her attention. “I know a good suit when I see one, and this one looks magnificent.”

“Oh, a fellow designer?”

“Only a customer, I’m afraid. A customer that has a taste for good clothes,” Dapper shot her a few brief glances and smiled. “And other rare and beautiful things.”

“Is that so, mister... I’m sorry I didn’t get your name?”

“Dapper, ma’am. A pleasure to meet you.”

“Dapper...” Rarity smiled back, eying his perfect body the same way he eyed her. “Your name suits you well, I see.”

“Likewise. An intelligent, beautiful mare working as a designer is a rare occurrence in these parts.”

The cheap and cheesy compliment filled Rarity’s face with a blush, and a sultry look quickly followed. It was working faster than he thought it would.

“Hmm, maybe someone who has a taste in clothes could help me find the… inspiration I need...” Rarity said, then took a long sip from her martini, swirling the ice cubes with her tongue. Then, I added a teasing smile to the mix. " Would you be so kind to accompany me to my private chambers and help me pick up the right design?”

Jackpot, you cheap whore! Dapper smiled. “That would be wonderful, Miss Rarity.”

“Please, just Rarity...”

They quickly finished the drinks and went outside...

***

“You’re staying here?!” Dapper said in awe, eying the elegant walls of the palace tower suite. “Rarity, I must say you’re full of surprises!”

“Oh, it’s nothing, really, just a little indulgence on my part. It’s the only place in Canterlot with perfect privacy and a great, inspirational view of the entire city.”

“But it must cost a fortune.”

“Thankfully, money is not an issue for me. Besides, when you’re in my line of work, privacy is paramount. My career couldn’t handle a scandal if you know what I mean.”

Dapper nodded with casual expression, but deep down inside, he was grinning to himself. A rich mare that needs to have a clean reputation, it sounded almost too good to be true. If he played it right, he could be set up for life.

“All right, so... You want to show me some of the designs?”

With her magic, Rarity locked the door and pulled the blinds. Then shot him a seductive glance. “Darling, I think we both know you’re here for something very different…” She walked by, rubbing his chin with her curly tail, and drilling his nostrils with her scent. “Now, be a gentlecolt and lay on the bed.”

He didn’t need to be told twice. With a grin, he laid back, relaxed.

“Already eager, I see,” Rarity said, eying his hardening erection. “But first we need to make a little adjustment,” she levitated a red ribbon to Dapper’s front hooves. “This is OK, isn’t it? You wouldn’t mind a little role-play, I hope?”

Great, another kinky bitch… “Of course not, Rarity. Anything for a lady like you.”

With a nod, Rarity quickly tied his front hooves to the bed, then did the same to his hind legs. When she was done, a series of tight knots held him in place – like some slave just before a grand sacrifice. But the pre-cum oozing from his rock-hard cock was a dead giveaway, this slave was enjoying his torture.

“Now, let me just take out the tools for tonight,” Rarity said, bending over an opened saddlebag on the ground. “Oh, my, there is such a mess in here, it will be a moment…”

Dapper said nothing. His eyes were locked onto Rarity’s moisty flower, the alabaster white opening was winking towards him, teasing him and inviting him to deflower it. And glancing at the various sex toys Rarity pulled out of her saddlebag, the night was looking promising. Until...

“Ah, here it is!” Rarity brightened up. “And I thought I forgot about it, silly me.”

Dappers’ smiled evaporated in an instant. What Rarity was levitating, looked like giant pliers. “H-hey, what the hell is that?” But this time, Rarity was silent, just approaching him with a dark grin on her face. “Hey! I’m talking to you, bitch! What is that?!”

Still, no reply.

With adrenaline flooding his veins like a river, Dapper jerked, wrestling with the restraints, but neither the bed nor the ropes showed any signs of falling apart anytime soon. He was trapped like a rat.

“Don’t bother, darling,” Rarity said. “My friends and I made sure that all restrains can easily hold a stallion twice your strength.”

“What the hell do you want from me?!”

“I’m here to teach you some things about life, and... to help you become a better pony.”

“W-what?!”

Rarity sighed. “Maybe this will explain it,” she took out a picture from her bag and levitated it to him. “Ring any bells?”

Dapper gulped, the air around him suddenly a bit too hot for comfort. “T-that’s...”

“The naive mare you met in the Confidential Blind Date program. You know, the one you later used, robbed, dumped, and threatened with embarrassing photos?” Rarity frowned, her glare cold as ice. “Her real name is Fluttershy, and she is my friend.”

Cold sweat flooded Dappers’ forehead, but he decided to play it cool. “Let me go, bitch! I have powerful friends you can’t even imagine!”

“Like the Lord of Chaos, princesses, and a human super soldier? Oh, wait… That’s MY friends, and Fluttershy’s friends, too. Do you know anyone who can top that?” Seeing his bluff falling apart like a house of cards, Rarity smiled again, reveling in terror filling his face. “Thought so—”

“Help! Somepony, help me! Help me! He—hrmm!”

Rarity’s magic shut his lips tight. “Don’t bother, darling. When I locked the door, I put on a sound dumping spell around the entire room, nopony is coming. Now, if you promise not to scream, I will...” Rarity paused, and tapped her chin, then nodded to herself. “On second thought, maybe I better keep that gag for a few more seconds.”

Dapper was twitching and jerking, in total panic. His eyes locked onto the pliers-like tool that was descending towards his defenseless scrotum.

“Hrrr! Hrm?!”

“Oh, that? It’s a little device my human friend brought from Earth. It’s called the... burdizzo, I believe. They used it to emasculate stallions, to make them less aggressive…”

Dapper’s jerking intensified, shaking the entire bed. His terrified eyes frantically going from left to right. But Rarity didn’t care. Using her magic, she began gently examining the left part of the sack until she located the spermatic cord. It was throbbing, proudly sending the life-giving blood down to his fat baby-maker. But not for much longer.

Rarity placed the cold metallic tool around his scrotum and smiled gently. “This may sting, a little...”

She clamped down on the handles, hard, forcing the jaws to close completely just above his left ball, crushing the cord with a loud, sickening crunch. The effect was immediate.

“HRRRRRR! ARHHHHH!!”

He screamed and screamed and screamed. Even with his lips shut tight by Rarity’s magic, Dapper’s desperate muffled hollers spilled all over the room. His body thrashed and jerked, bucking his hips, and shaking the entire bed – like a mad bull during branding.

With the frantic scene playing in front of her eyes, Rarity caught herself, licking her lip and panting with excitement. When she decided to masquerade as the naive mare and arrange this encounter, she had convinced herself it was just to get justice for Fluttershy. She promised she wouldn’t be doing that to fuel her dark fetish. But with the view of helpless playboy writhing in agony, sending waves of pleasure up her love canal, she had to admit defeat.

She came hard! Her alabaster pussy began contracting, squirting her juices down her hind legs, and forcing a series of uncouth moans and grunts out of her. It was the power-driven orgasm of dominance and submission, fueled by the torture her partner was going through. She loved every second of it.

Rarity came to her senses a few minutes later, when his trashes died down and yells turned into desperate whimpers. The damage was done; the bruised and swollen left side of his scrotum was proof of that. With no blood coming through the flattened vein, the fat orb that had powered his proud cock for the entire life was doomed to painfully wither away and die.

“My, my, and it didn’t even cut through the sack! James was right. This tool is marvelous!” Rarity un-clamped the steel jaws, forcing a painful groan out of her partner. “Well, one down, one to go.”

“Y-you whore...” Dapper mumbled through tears, still trying to play a tough guy. “I’ll... kill... you.”

“This aggression is exactly why we’re doing this,” Rarity leaned on the bed, glancing him in the eyes. “You see, when James – my human friend, and Discord learned about what you did to Fluttershy, they were... upset. The first one wanted to skin you alive and cook in boiling oil, while the other wanted to send you to the... the dimension of eternal torment, or... something. Both of them were dead serious about it too. Fortunately for you, I was able to convince them that too much testosterone can force you to make stupid and nasty things...”

Dapper flinched, then bit down, hard, hissing and shaking. Cold sweat began flooding his forehead. As if the searing pain in his scrotum wasn’t bad enough, there was a new squeezing sensation coming from his dying ball. Like a powerful kick to the nuts, getting worse by the second.

“Yes, I know. A dying testicle is a painful thing,” Rarity said, then frown. “Then again, after what you did to Fluttershy, you deserve every second of it!”

Another pliers-looking tool floated out of the bag. This one was smaller and had a tiny rubber ring at the end. Without further ado, she squeezed the handle, expanding the circle, pulled his sack through, then let go. The rubber band snapped back with a vengeance, biting the skin just above his nuts, sending another wave of pain up his spine.

“Ugh! Oh, f-fuck! Get it off, get it off!” Dapper let out a begging scream, feeling the ring cinching tight around his balls. “Fuck, that hurts!”

“It will only get worse, I’m afraid. It usually takes a few hours for the testicles to die down.”

“H-hours?! No! Get it off now!” Seeing Rarity rolling her eyes in annoyance, Dapper’s tone switched to pathetic pleading. “P-please... I beg you, take it off. I’ll do anything!”

But Rarity shook her head. “Darling, you still don’t understand, do you? When you hurt Fluttershy, you sentenced your family jewels to death. If I don’t do it, then one of her other friends will, and believe me, you don’t want that.”

Dapper’s eyes filled with tears, whether from the guilt crushing his conscience, or the elastrator crushing the cords of his balls, Rarity couldn’t tell. But the stud that just a few moments ago was cocksure and arrogant was now whimpering like a little boy. Even after all he has done to Fluttershy, she still found him a pitiable man.

“Oh, don’t be like that. With the voluntary castration still illegal in Equestria, I have dozens of stallions who pay me good money for the treatment you receive. Believe me, they’re much calmer and happier afterward.”

Dapper let out another series of whines and whimpers, his body twitching and sweating profusely as the pain was starting to consume him. But to Rarity’s surprise, his dick was standing upright, rigid, and hard as steel. As if it was begging her for one more ride before the end. Maybe it was the final act of generosity, pity, or kindness, or maybe she just wanted to extinguish the fiery inferno that once again began forming inside her twitching vagina. Whatever the reason, she had decided to honor the request.

Rarity’s lowered her lips, and without warning, swallowed his throbbing erection. Bobbing her head up and down, she began working the shaft, making sure to push the cock against her swirling, rough tongue. At the same time, she pushed a vibrating black dildo deep inside her needy cunt, and turned it on.

With the mix of the sudden impact of delight coming from Rarity’s blowjob, and the agony coming from his starving nuts, Dapper jerked and grunted in confusion. But when Rarity pushed his dick past the entrance to her tight throat, she could feel his dying balls contracting, readying for the final release.

Knowing what was about to happen, Rarity levitated her heavy-duty 12-inch tailors’ shears and placed it against his sack. Then, she pushed her dildo to the maximum setting and waited for him to cum. And cum he did, his body arched, and he fired like a hydrant, filling Rarity’s mouth with his thick seed. It was the most violent orgasm of his life – his body’s final attempt to fertilize something, anything before his balls were gone. It was going and going and going...

As the first wave splashed against the back of her throat, Rarity closed the handles of her scissors. The razor-sharp blades came together, cutting through the bulged scrotum like a hot knife through butter.

“F-fuck!” Dapper yelled, his mind drowning in the sea of pain and pleasure.

His sack hit the bed a moment later, even as his cock was still pumping his jism. The wave of delight coming from the view of his ball-less prick, mixed with the stimulation coming from the vibrating dildo embedded in her love canal, sent Rarity over the edge. She came harder than before, squirting her juices like a garden hose. The contractions of her alabaster pussy were violent enough to push the dildo outside, lunching it into the air with a force of a missile, sending another wave of pleasure up her body. Just like her partner, she just came and came and came, lost in a sea of heavenly delight.

When her senses returned, her cheeks were filled to the brim with fresh, warm cum. Dapper’s cock that just a moment ago was like a rod of steel was now shrinking rapidly. It plopped out of her mouth a moment later, getting smaller and smaller, like a frightened, defenseless snail trying to hide inside its shell, and to stay there forever. The pathetic sight was like poetical justice, justice for Fluttershy, and it put a smile on Rarity’s face.

Dapper was a different story. The former stud was lying on the bed, confused, with eyes wide open, not understanding what just happened. The pain in his groin was still there, but it switched from squeezing to searing. He knew Rarity’s mouth was full of something, but not what. Even when Rarity had levitated his severed scrotum above his abdomen, Dapper’s mind was still stuck in the loop.

It wasn’t until the first ball hit Dapper’s belly that the epiphany struck him like lightning. His jaw hit his chin, and he stayed there frozen, just gaping in horror at the lifeless nut. The second one landed next to its neighbor a second later, completing the picture. The testicles that defined him as a stallion fueled his giant cock, gave him confidence and power for his entire life were now rolling freely on top of his stomach. But that wasn’t the end of it. Rarity swirled the potent seed, still residing in her mouth, and with a smile spat it out, marinating both nuts in his own jism.

The view of his dead balls, drowning in the same seed they have helped create, was the final act of humiliation and punishment. Judging by the tears that flooded his face a second later, it worked like a charm.

Without wasting time, Rarity quickly glanced at what was left of his scrotum, making sure the elastrator ring was still in place, and there was no bleeding. With a few swift motions, she sewed the skin around the rubber band to hold it in place. Then, she packed her bags, and went towards the door, leaving the wailing Dapper tied to the bed.

“H-hey, you c-can’t leave me like this!”

“You need time to think about some things. But worry not, the mare that will find you in the morning is very discrete. Which reminds me... My friends and I expect you to return Fluttershy’s money and those nasty pictures you threatened her with, by Monday. If not, well... " A few room amenities launched into the air, revealing a bunch of well-hidden cameras, which Rarity quickly placed inside her bag. “Let’s just say, you’re not the only one who can threaten others with ugly pictures. And remember that Fluttershy’s other friends are more than eager to pay you a visit. If that happens, then today will be like child’s play. Do you understand?”

Dapper said nothing, he didn’t have to, the sobs and whimpers coming from his trembling body was confirmation enough. Without further ado, Rarity left the tower’s suite, leaving the former stud defeated and broken. He would pay, Rarity was sure of that. They all pay. They always pay.

With that thought, Rarity left the palace area, and as if nothing happened, and went to the train station to catch a ride back to Ponyville…

Author's Note

'Why,' you ask? Because there weren't enough castration fics, that's why. I regret nothing