Classy and Gear
The first sign of evening stars glimmered above Classy’s head as he walked through the streets. It was late, so most of his company was limited to the dimly lit street lights above flickering on one by one as the last traces of twilight left the night sky. He had a long day of travel, and behind him, he drug along with him a suitcase that was considerably heavy. The cool air whipped at his body and caused his neatly pressed tie to flap in the wind. He grumbled under his breath at the suit he had so meticulously pieced together looking distinctly more ruffled and less pristine after a day of travel. Being half-zebra it was already difficult for him to look well put together when his stripes clashed with everything. He tried his best to smooth it out with his hooves, but he knew that nothing short of a proper iron would do the trick for good. No bother. It wasn’t like his clients knew the difference between an expensive-looking suit and a sub-par one.
At the very least it was his outfit that was out of sorts and not his plans. Classy always made sure to keep his plans in neat order. So much as arriving late or skimping on the terms of a contract just wouldn’t do for his profession. He took those sorts of things very seriously. Those were the sort of details he would never lose track of. He wouldn’t be a professional if he did, after all.
Classy arrived at the front door to the home exactly one minute ahead of schedule, which he checked quickly via pocket watch. Right on time, as usual. He fished into his pocket once more to retrieve a key that he had received at an earlier time. It glimmered a bright gold. He used it to unlock the door and pushed his way in without any sort of warning.
His client was already awaiting his arrival. The pony’s name was Gear, and he stood against the wall of the well-decorated but spacious room. He was a brown pegasus with black hair full of streaks of gray. He had a sly look on his face that Classy recognized well. It was the look of a brat. His shit-eating grin was the only welcome that Classy received. He looked at the stallion like he was above him and truly believed that.
“Got a drink?” Classy asked. “It was a long trip.”
“Over there,” Gear said with a nod of his head over toward a small cart full of glasses and various bottles of booze.
Classy made his way over, still lugging the luggage behind him, and began to pour himself a glass of whisky on the rocks. It seemed like the pricy stuff. This guy didn’t skimp, that was for sure. He took one brief sip and then shrugged his shoulders.
“Be sure to enjoy that drink,” Gear said with a bit of a huff. “It’s probably worth far more than what I paid you.”
“Is that so?” Classy asked as he took one more sip and then set the glass down. He eyed the stallion up and down. Everything about him from his stance to his grin screamed that thought he was better than Classy. He had the role of a brat down to a T. “Can we get around to the deal? I’m awfully busy. I have the papers for the product here if you want to go ahead and sign it.”
“I’m not signing anything,” Gear said. “You expect me to just do it instantly? Without even seeing the product?”
“Well, I did come all this way,” Classy said with a slight glare in Gear’s direction. “I assumed that’s what you wanted me for.”
“Listen here,” Gear said as he got closer to Classy. He reached out a hoof and took Classy by the chin so their eyes would meet. It was rare for a client to dare look him in the eye so haphazardly. “We do this how I want or not at all. You’re don’t make the rules, I do. That clear?
“You’re giving me an order?” Classy asked as he pulled his chin away. “That’s bold.”
Without warning, Classy ducked and swiped his leg. He yanked the legs right out from under Gear with one motion and sent him falling to the ground with a thud followed by a loud grunt. Classy moved forward and pressed one hoof down against Gear’s chest as he picked up his whisky glass again and took another sip.
“Can’t I at least finish my drink before you be so difficult?” Classy asked. “I’ve had a long day.”
“Wh-Why?” Gear asked. He was still grinning despite easily being taken down. “That tuckered out from your trip, old man?”
“Old?” Classy asked with a raise of his brow. That was new. “Cutie like yourself should watch your tongue.”
“I ain’t cute!” Gear snapped as he squirmed underneath Classy’s hoof.
“That’s a clear lie,” Classy said with a roll of his eyes. He used his unicorn magic to begin to undo the zipper on his bag. He yanked out a black mask first thing and hovered it over to Gear. The stallion’s eyes widened and for a moment that smug expression wiped from his face. “Well, I suppose since you want to see the product before you sign the deal I’ll have to oblige. Though I also think you deserve a bit of punishment for how rudely you’ve treated your guest.”
“What’s that?” Gear asked.
“Did I say you could speak?” Classy asked.
“I’ll do whatever I wa— MMMPH!”
Gear tried to respond with yet another bratty response, but Classy was having none of it. He forced the mask right over Gear’s face. It was tight and seemed to fit him perfectly. For a few moments, the pegasus whined until Classy reached down and began to unzip the area right in front of the mouth. The first thing he heard was a loud gasp from Gear.
“Ahh! Y-You bastard!” Gear whined.
“Shush,” Classy said. He moved his hoof up and pressed down further up Gear’s chest until his head was forced to go back down against the floor. “I let your mouth out not so you could keep jabbering, but so I could have some fun.”
Classy pulled another toy from his luggage using his magic. A dildo. It was bright pink. Classy brought it forward and without warning thrust the head of it right into Gear’s mouth. The sound of a muffled cry of surprise was all Classy heard before he forced in more until it was right at the base. Gear continued to whine despite the cock near touching the back of his throat now. He squirmed, but only a little.
“Listen here,” Classy said. “I know everything about you. Your likes. Your fantasies. I also know how to get what I want from young upstarts like yourselves, even the brattiest of you, and I will get what I want one way or another.”
Classy finally took his hoof off of Gear’s chest. The poor masked pegasus was left there panting and whining softly as the fake cock continued to rest on his tongue. Classy adjusted his necktie once more as he turned to begin properly emptying out his luggage.
First came a video camera, and then a slew of toys of various shapes and sizes. The last two items were a breeding bench followed by a motorized machine that he placed to the side for the moment. Classy placed the breeding bench directly in front of the armchair and took a few moments to determine where it would look best.
The sound of more whiny cries came from behind Classy. The brat was getting restless. The zebra looked over his shoulder to see Gear squirming and trying to sit up. Classy went over and put his hoof back down on the boy’s body.
“One last chance, cutie,” Classy said. “Submit and this will be far easier on you.”
Gear was defiant and tried to push away Classy’s hoof from his chest. That was okay for Classy, who merely smiled at the young brat’s continued defiance. He enjoyed a bit of a fight from his playthings.
“Have it your way,” Classy said.
Classy didn’t dare lift a hoof and risk dirtying himself fighting and struggling to get Gear where he wanted him. He let his magic do the work in picking up the fighting pegasus and brought him over toward the breeding bench. Leather straps began to fly about and bind the squirming boy to the bench. He continued to let out muffled whines through the dildo lodged firmly in his mouth. Eventually, he was hunched over onto the bench with his back end sticking up. Classy had gone to the work of pulling back his tail so it wouldn’t hide that wonderful-looking rump of his. The zebra grinned as he moved forward and rubbed his hoof against it only to be rewarded by a defiant whine from the still resistant pegasus.
Classy used his magic to pull the machine from before over. A long pole stuck out leveled directly at the perfect height to point at Gear’s presented ass. Classy moved over to the pile of toys he had put out on the armchair before and watched as Gear’s eyes followed every movement of his hoof from toy to toy both big and small.
“I know your tastes well,” Classy said. “You have a MeanLizard Extra Large somewhere, don’t you? Awfully large for somebody who wants to come off so tough looking.”
Classy looked over. He could swear that Gear was glaring at him through his mask. That only made the zebra put on a sly grin.
“Then I suppose it isn’t too much to ask you to handle this boy,” Classy said as he grabbed one of the larger toys from the pile. “This one is extra extra large. Don’t worry, it’ll fit. Eventually. I’ll make sure of it.”
For the first time, Classy saw a flicker of nerves flicker in Gear’s eyes. That was good. He was too distracted by what was about to happen to him to keep up that brat act too consistently. Classy enjoyed that moment of distress. The fear the client might be a bit too in over their head. It only lasted a moment, but it was always delectable to watch.
“Of course, I’m not a monster,” Classy said with a chuckle as he used his magic to pull out a large bottle of lube from the nearby suitcase. “You certainly aren’t going to take it on dry.”
“Mmmph!” Gear whined.
“Quiet, colt,” Classy said as he snatched the bottle from the air and made his way toward the back of Gear’s body. “You yourself said you wouldn’t sign my deal until you had some idea of how it worked. First-hoof experience is always the best and most direct approach I’d say.”
Classy twisted off the cap of the lube and let a glob fall into his hoof. He used his other hoof to reach out and slap down against Gear’s bare bottom. The pegasus’ whine was audible even through the gag, especially when Classy pulled apart the cheeks to reveal his hole.
“My, that looks delectable,” Classy said as he lowered his hoof down and began to smear a helping of lube against the hole and all around. He made sure to use slightly more than necessary just to assure that it went smoothly. “Shame it’s going to be utterly wrecked in a few moments.”
Another whine. That made Classy smile. He could feel the cocky colt squirm on the breeding bench. The leather straps keeping him down twisted and tugged as he helplessly tried to wriggle to freedom. That wasn’t happening. Classy was a professional and could probably tie up any creature blindfolded at this point. Nopony got out of his bindings until he allowed it.
Classy took the bottle of lube over toward the fucking-machine. The massive dildo attached to the end of it was the size of Classy’s forearm. It certainly was going to be an experience for the bratty colt. He used more lube on the dildo to assure that every inch was covered. Though he was teaching Gear a much-needed lesson it wouldn’t be fun for either of them if there was zero pleasure.
Classy then set up a grill underneath the machine and attached wires to it. It would catch any accidental leakage that may result from Gear’s showcase, and when that happened a fun surprise would await the pegasus.
As soon as he was finished Classy went over to pour himself another drink. He took his time tediously refilling the ice and taking a small sip of the whisky. He could hear Gear whine behind him, and the sound of it was enough to bring a slight smile to his face. He composed himself before turning around and wandering over to the armchair which he had intentionally placed in front of the breeding bench. He sat down with a sly grin and stared into the eyes of the pegasus who was trying his best to glare at him.
“Aw, don’t give me that look,” Classy said with a chuckle. He used his magic to pull a remote from his bag and pulled it to his free hoof as he leaned back. He raised his hind leg and pressed the tip of his hoof right against the dildo still lodged in Gear’s mouth. The pegasus gave a whine of protest. “Let me explain how this is going to work.”
Classy pressed a button on the machine. It began to roar with life. Gear’s eyes widened as he struggled to look over his shoulder. Classy stared on as the head of the dildo drew closer and closer toward him. He let it get right up to Gear’s lubed and ready hole before pressing stop. The head of the dildo must have been practically kissing that hole now, and any slight movement from Gear would only make it go inside.
“You try to escape this bench, and I push this further down your throat,” Classy said with a threatening tone of voice. He pressed the tip of his hoof slightly against the dildo in Gear’s mouth. Gear whined as it went in just a little more than a centimeter. “If you squirm too much you’ll get pushed forward, which will also send it further down your throat. If you do anything I just don’t care for I’ll also push it further in. Do we have an understanding, Cutie?”
Gear responded by whining and squirming. He glared at Classy once he was called cute.
“I’ll take that as a yes,” Classy said.
Classy pressed the button on the remote again, and once more the machine came to life. Gear’s eyes widened as the dildo’s head pressed against his hole. His eyes went back slightly as it inserted, and a whimper so loud he might as well have not been gagged escaped his mouth. Classy could see his hind legs tremble slightly as the first few inches of the cock pressed roughly to his hole. The head went in, and Gear let out a whine.
“That easy?” Classy asked. “Well you aren’t screaming in pain, so I take it you’re used to that hole of yours being used for large objects. How slutty.”
“Mmmmph!” Gear let out a loud whine as he shook his head slowly. Classy watched as Gear’s body both tensed and relaxed in equal spurts as his body grew used to the new massive cock in his rear.
“I do enjoy this machine,” Classy said as he lifted the remote in his hoof to examine it with a sly grin. “It has everything one could ask for. Speed variation. How far I want that cock to thrust into you. How fast I want it to go. I can even make it feel just like a real stallion if I so choose. Top-quality stuff, really. Why don’t we start off slowly? You may be a cute little brat but I don’t want to overwhelm you too quickly. After all, it’s no fun playing with broken toys. Although perhaps you do want to be broken deep down. Or not that deep. Thoughts?”
Gear’s eyes widened the more Classy explained all this machine could do.
“Sorry, I forgot you can’t answer,” Classy said with a chuckle. “But those yes tell me oh so much. Alright, enough foreplay. Let’s get going, shall we?”
With a single press of a button, the cock pushed itself in. Or at least it tried too. Gear’s hole might have been well lubed and prepared, but the force of the machine was a bit too great. It popped right out of his hole and grinded lengthwise up his buttcheeks like a hotdog. This caused Gear to skid forward an inch, which pressed the dildo in his mouth further down his throat.
Perhaps a kneejerk reaction to the dildo in his mouth or just plain foolishness, Gear decided the best course was to jerk his body back. This only caused the dildo to twist more and somehow end right back up against his hole. The head of the cock inserted itself, and the noise that Gear made was wonderfully loud and whiny.
“Those noises are awfully slutty sounding,” Classy said. “Which tells me that you’re awfully used to large cocks like this one.”
“Mmmph!”
“So, about my business,” Classy said as he leaned back. He kept his hoof on the intensity and made sure it was at a minimum. Right now the dildo was tediously moving in and out of Gear at such low speeds that it could hardly be considered fucking. However, it was certainly enough to make Gear’s nerves go haywire all the same. His eyes bugged out each time the dildo pushed forward, and he would whine and moan. His little friend had come out to play as well as his sheath displayed a cock that had half hardened during this endeavor.
“My toys are high quality, as I’m sure you know first hoof by now,” Classy said. “What do you say? Will you sign my papers? I just want to sell them someplace and you seem like a respectable, if rude, pony of interest to do so.”
Gear let out a grunt and a glare in Classy’s direction. Classy responded with a slight frown as he swirled his glass of whisky around in his hoof.
“So resistant,” Classy said before taking another sip. The liquid burned his throat as it went down. “Don’t you like my toys? Your friend certainly seems to.”
Classy reached out his hoof and gave the cock a long stroke. Gear squeezed his eyes shut, but it wasn’t enough to stop the obvious moan from squeaking out behind his gag.
This bratty boy was so damn adorable. Classy couldn’t help but smile mischievously as he lightly stroked at the cock. The look in his eyes was pure bliss. All of his senses were overwhelmed by pleasure and overrode his desire to act angry or annoyed. As the cock continued to move in and out of his hole he only whined louder and louder. Eventually, a single stroke was all it took for Classy to coax a dry orgasm out of the squirming boy. His cock spurted a wonderful helping of pre directly overtop the grill he had set up before.
“Silly boy,” Classy said as he drug his hoof down the cock until it ran over the head. Gear trembled from sensations.
His pre-cum hitting the grill triggered the machine. It began to thrust in faster. On top of that, a loud buzzing sound could be heard. Gear’s eyes widened in a panic as the dildo not only picked up speed but began to vibrate as well.
His squirming turned out to be a mistake because very quickly Gear accidentally pushed himself forward and shoved the dildo further down his throat. That, and the intensity of the machine was gradually gliding him forward every few thrusts. Gear’s whining got louder and louder as his eyes went back. A mix of panic and pleasure filled his eyes as the dildo went deeper and deeper into his mouth.
“What’s wrong?” Classy asked. “Getting difficult to breathe? I’d have thought that throat of yours would be used to something of this size.”
“Mmmph!” Gear whined loudly. He could barely be heard over how loud the buzzing was getting. His insides were being stimulated so much so that his mind must have been numbing to anything but pleasure, though it couldn’t ignore for very long the need for air. His eyes darted over to the contract near Classy’s belongings that he had refused to sign earlier.
“Mmmph! Mmmm!” Gear whined loudly and nodded his head in the direction of the papers.
“Oh, feeling less resistant to signing now?” Classy asked.
Gear nodded his head enthusiastically. Classy smiled.
“Good boy,” The unicorn said.
Classy pressed a button on the remote, and very quickly the dildo inserted itself all the way into his hole. Gear’s eyes widened and for a moment Classy swore he could see them glimmer with stars as his prostate was hit. He pressed the remote again, and it began to thrust in and out. Though this time, it was only moving back and forth about four inches. The head of the long and buzzing dildo kept hitting down against Gear’s prostate again and again.
“Mmmph! Mmm! Mmmmmmmmm!” Gear whined loudly with undeniable pleasure. Even the most annoying and irritable of all stallions couldn’t help but get overwhelmed from pleasure at that feeling. By now his hole was properly stretched and there was likely no discomfort even with the size in question.
Classy knew from the start that he could fuck the brattiness out of any colt, yet he never tired of the process. The journey from resistant to blind and pleasure-driven toy was a beautiful thing to watch unfold time and time again. Right now Gear was practically putty in his hooves and would do anything just to keep that cock thrusting into him. He moaned so loudly that the cock in his mouth vibrated slightly as Classy grabbed at it and pulled it out a few inches to give him the opportunity to breathe. He then pushed it back in, and mimicked the movement of the fucking-machine as he thrust it in and out to stimulate the sensation that the stallion was being spitroasted.
Gear’s eyes were glimmering from just how far the cock was down his throat. His eyes rolled back briefly as he continued to whine with pleasure.
“It’s a bit disappointing just how quickly you gave in,” Classy said. “Perhaps you truly just are that much of a slut, though. You want to cum bad, don’t you?”
Gear nodded his head. He was helpless to the whims of Classy. The unicorn smiled mischievously as he continued to thrust the dildo in and out of his mouth. By now Gear was practically suckling on it, and needy for more.
Judging by the way Gear’s cock was practically twitching he seemed to be awfully close to orgasm. Classy debated giving him a helping hoof, but thought watching the poor colt whine and squirm his way to orgasm from nothing but a good pounding was far more entertaining even if it took longer.
Despite how horny and desperate Gear was for the pleasurable bliss of release it still took a total of three minutes for him to finally cum. When he got close his eyes shut and he began to moan louder than ever before. If it wasn’t for the dildo Classy had no doubt he would be panting like a dog in heat.
Classy grinned and pressed one final button on the remote. It stopped the fucking machine right as it thrust in the deepest and dug into Gear’s prostate. The vibration continued though and pressed down to the pleasure spot. That alone was enough to push the stallion over the edge. His legs trembled almost like they were jelly as he hit the point of no return and a gushing torrent of seed exploded from his cock. There was such a massive amount of it to the point even Classy raised his eyebrows in surprise. Spit dribbled out from the corners of Gear’s lips as he cried out in pleasure and threw his head back as far as both the bondage and his body would allow. He shot not once, not twice, but three times. It was so much cum that some of it shot right past the grill and onto the armchair where Classy was sitting.
“My,” Classy said before lowering his hoof down to Gear’s cock and gliding it over some of the dribbling cum. He brought it to his lips and nearly purred with delight as the taste hit his tongue. “Somepony was worked up.”
Gear looked like he could hardly hear Classy. The poor stallion must have been so overwhelmed he practically passed out. His eyes looked glazed over and even a little teary from just how intense the experience had been. Classy slowly removed the cock from his mouth and watched as he panted. He quickly hit the button on the remote to stop the machine and pull it out. It didn’t look like Gear was going to be doing anything on his own for quite a bit.
“One moment, dear,” Classy said. “Let’s get you cleaned up.”
———————————————————————————
It was some time later when Gear finally came to his senses. By then he had been freed of all of his bondage and was lying on a mess of towels on the armchair. His hole felt like it was throbbing, and his jaw ached from being open for so long. He whined slightly as he shook his head only to feel the touch of hooves tighten around him. He hadn’t even realized he was being held until lips found their way to his neck and gave him a gentle kiss.
“Shhh,” Classy said to the stallion he was holding so tenderly. “You coming around, dear?”
“Y-Yeah,” Gear said with a slight stutter. “That was really intense.”
“Not too much so, I hope,” Classy said. “Are you alright? Do you need anything?”
“No, no, it was great,” Gear said. “I don’t know if I can walk anytime soon but… wow that was good.”
“You sure?” Classy said. He rubbed his hoof up and down Gear’s chest in slow and tender circles. “I’d hate to think you had a bad time. My clients should always walk, or limp in your case, away feeling good.”
“You worry too much,” Gear said with a slight chuckle.
“Mhm,” Classy agreed as he buried his muzzle into Gear’s neck and squeezed him gently. His horn glowed as a glass of water was levitated over toward them. “Drink something.”
Gear did as he was told and took a few sips of the water. Truth be told his throat did ache a bit from just how deep the dildo had gone down it. However, this discomfort was worth it for the thrill he had just experienced. He settled down into Classy’s arms and allowed the zebra-unicorn to nuzzle him gently.
“You’re awfully cuddly when you aren’t in character,” Gear said with a slight giggle.
“My clients deserve the best pain, and the best care,” Classy said. “You’re no exception.”
Gear giggled again as he shut his eyes and allowed himself to rest his head on Classy’s chest. Truth be told any aches or pains he felt right now were practically meaningless next to how comfortable he felt.
“Remind me to hire you again,” Gear said sleepily as he turned and buried his face into Classy’s fur. “Soon.”
“Hehe, will do,” Classy said before running his hoof through Gear’s mane. “Get some rest before thinking of that, though. The last thing I need on my hooves is you passing out on me again.”
The two of them sat there like that for some time just cuddling and resting. It was an easy enough job for Classy, and having an adorable client made it even more enjoyable for the unicorn. Moments like this were when he was glad to be in the profession he had. When all the leather and dirty talk was gone all that was left was a satisfied stallion happy to have experienced something enjoyable.
Classy smiled softly as he shut his eyes and relished in the opportunity to rest. He would have many more clients soon enough, but for right now all that mattered was the one he was cuddling.