Button Takes Manehattan

He felt something touch his cutie mark. He gasped and quickly turned his head around to try and see the contact being made. Whatever it was had started making slow circles on and around his cutie mark (three different game controllers stacked on top of each other). Try as he might, he was unsuccessful in seeing who it was.

“S-stop!” he called out, a bit more loudly than he had intended. He shrank down what little he could while laying down. He looked to the unicorn mare to his right who was currently serving as his attendant. “S-sorry. Could uh… Could I get a mirror, please? I want to see who it is back there.”

The mare nodded, then lit up her horn, pointing it in front of Button. In less than a second, a full-body mirror had appeared, allowing him to see who was behind him.

A tall, strong-looking green stallion was behind him, hoof raised just above his cutie mark. Button nodded at him to go ahead, and the gentle rubbing continued, making those same small circles as before. For some light petting, it felt surprisingly good.

Button hummed happily to himself. “That feels great...” He closed his eyes, enjoying the peaceful moment.

That was, until he felt something wet and very cold on his rump.

“Ai!” he yipped, eyelids flying open again to try and get a view of what was going on back there.

“Hey now, calm down. Just putting some lube on. Don’t want me to go in dry now, do you?”

Button blinked. Right. The sex. He had almost forgotten.

“O-oh. Uh, yeah, sure. Go right ahead.” He laid back down and tried to relax again, but the massaging now being entirely focused on his backdoor kept up a bit of tension in him that refused to let go.

The hooves left him, leaving the wind open to cool his sensitive—and now wet—bits, eliciting a shiver response. He wondered when the hooves would return to him, but he got his answer soon enough when something else pressed against his ring. It wasn’t as large around as a hoof, not even close, but was way warmer. Button had a few guesses as to what it could be, but then he felt the stallion press his stomach against Button’s back. No doubt about it now. Button was about to get bucked.

The stallion spoke up, voice now much closer and clearer. “Are you ready… uh… I never got your name.”

“B-Button. Button Mash. It’s n-nice to meet you…?”

A single laugh. “Silver, and likewise.”

Button felt a slow but definite pressure building up as Silver pushed against the semi-virgin hole (Button had toys, but had never had a proper coltfriend). A spike of fear ran up his spine. What if his first time turned out to be terrible? What if he regretted it not being with somepony he knew? What if—

He took a deep breath. Everything was going to be fine and he was going to have a blast. And if he didn’t he could always just call it quits early. He released the breath, more relaxed than before.

Thanks to the massage, but mostly the lube, the penetration wasn’t all that painful. Button was mostly shocked, suddenly taking in a sharp breath as it popped in, holding it as Silver held his place.

“You good, Button?”

He nodded vigorously, then released the breath in a sigh. “Y-y-yeah, whoo. I’m good. I’m good. Still getting used to things being up there. I haven’t had a real stallion yet. It’s uh, weird feeling your pulse in my butt. Either I’m way more sensitive back there than I thought, or you’re really hard right now.” Button tried to turn around to look at Silver, but the only part he could see was his muzzle, which was plastered with a big grin.

“I am very pent up. It’s been a while since I’ve gotten any actual action besides those fake mounts. As good as they are, they can never really match a real mare.” Silver realized his mistake as soon as the words left his mouth, sitting up straight suddenly and correcting himself. “Stallion! A real stallion!”

Button had thought to forgive Silver for the mix up in wording. It happens to everypony, after all. But his brain stopped formulating thoughts when it registered that Silver sitting up straighter had incidentally pushed another few inches of his stallionhood into Button’s ass.

“Ooooh, Buh… Buck. S-s-sweet C-Celestia,” Button moaned. He shifted around slightly, trying to get used to the pole that had quickly made its way almost fully inside him. “W-wasn’t expecting that.”

“Sorry about that, bud. And sorry for calling you a mare. You don’t look like one. You’re a… very… handsome stallion?”

Button frowned. “You don’t sound very sure about that.”

Silver buried his face in Button’s shoulder and groaned. “Ugh. I’m the worst at this. Listen, I’m not gay, so this is still a little awkward for me. I’ve never called another stallion handsome before. And I definitely haven’t been balls-deep in one either.”

Button took all that in and paused for a moment. Silver was pretty far in, but Button could swear there was at least some more room back there. “You aren’t balls-deep right now, are you?”

Button heard a small huff of air come from Silver. “Not yet.” Then Silver bucked all the way forward until their hips hit each other with a loud Slap!

Button opened his mouth in a silent scream. Whether it was in pain or pleasure, he didn’t know. All he knew was that it had overloaded his senses, and he needed a minute. Or two.

“B… Bucker,” he finally got out. His body had decided that an appropriate response to getting rammed was laughter, so Button found himself alternating between moans and chuckles as he once again tried his best to adjust.

“You like that, huh? Old family recipe, that one. We like to call it “Being an Asshole”.” Despite Silver’s claims, and however much Button agreed, the nice massage he started to receive on his withers and the fact that, besides the rushed penetration, Silver still hadn’t moved at all led him to think otherwise.

Button decided to answer by grinding himself against the stallion, pushing it as deep as it would go and forcing it to scrape his insides. “Oh buck. Your cock is huge. Heh,” Button couldn’t help but laugh. “I bet you get that from mares a lot, huh?”

Silver was quiet for a moment. “I’d really rather not think of mares right now. I know I said I’m not gay, but I’d rather not think about her right now.”

Button was not in the mood for a therapy session. In any other situation, he’d be all for helping this poor guy with his woes. But, at this particular moment, Button only wanted one thing.

“How about this: I won’t mention mares and you have to buck the shit outta me. Deal?” He accentuated his point with another small grind.

“Ha! Alright Button. You’ve got yourself a deal.”

Silver slowly pulled out all the way, giving Button enough time to really savor the feeling of being emptied of the cock he had grown suddenly quite fond of, and then he slammed it in again, making Button shout in both pain and ecstasy, though with every thrust came more of the latter as his prostate started getting hit with both the tip and the medial ring.

The thrusts started slow and strong, pulling all the way out and then all the way back in, but as time went on it all grew faster and faster. Silver pulled out less and less each time, and if the extra pressure in his gut was anything to go by, Button could guess that Silver was probably flared already.

He was so distracted by all this that he didn't notice the pony directly in front of him until they spoke up.

"Button? Is that you?"

Button opened eyes he didn’t realize were shut and looked up to see Star Bolt, a lime pegasus with a bubblegum-colored mane who he remembered from grade school. "H-h-hey, B-Bolt!" he finally got out between gasps. The stallion behind him hilted and held there, and Button could vaguely feel the cock inside him twitching.

"Wow. I gotta say, I never expected you to be in this sort of position. I didn't even know you were gay."

"W-what gave it away?" Button asked slyly.

Bolt looked between Button and the stallion taking a short rest on his back, who was gently nuzzling the nape of his neck. "Just a guess. So I'm gonna be honest, I don't really know where to start here. Should I just mount up like I'd normally do, or should I wait for sleepy over here to be done, or what?"

Button looked behind him and was met with a good look at the stallion’s face. From this close up Button could see every little detail. The lines on his face were hard, the sign of a slightly older, more experienced stallion, though it was contrasted by the dumb smile on his face that made it obvious he was still lost in the bliss of the moment.

He turned back to Bolt. "I could use a bit of a break back there. Feel free to mount up on this end if you want. I can take it. Probably." Button blushed, avoiding eye contact.

Bolt gently placed his hoof on the bottom of Button’s chin, guided it back to him, and then placed a kiss square on his lips. They stayed there for a second, then separated with a desperate gasp for breath, needed more to calm their nerves than for the oxygen.

"Sorry, it just kinda felt right. You alright with this?"

Button shook his head in an attempt to clear his thoughts. "Yeah, no, it's fine. Go ahead. Just, uh, start slow, alright?"

Bolt smiled as he placed his hooves on Button’s shoulders, lifting himself up. "Go slow, got it. Thanks Button."

Star Bolt’s dick was now in plain view, positioned directly in front of his face where he could see it. Funnily enough, it looked like a mini-Star Bolt, as it was mostly green but turned to a mottled pink near the head. Suppressing the urge to laugh (nopony wants someone’s first response to their junk to be laughter), Button reached out with his neck and gave the tip one tentative lick.

It wasn’t anything special, like Button had always imagined his first blowjob would be. It just tasted like skin. It didn’t fill him with tons of hormones and make him extremely horny, nor did he retract in disgust. Not even Bolt had much of a reaction, if any at all. For a moment, Button wondered if he was just doing it wrong.

He pushed any negative thought away as he reached out again, running his tongue up from the medial ring to the tip. Once again, it didn’t do much for him, and it elicited very little reaction from Bolt. A shift in weight from the hooves on Button’s shoulders, but that was about it.

Suddenly, Button had a very different reason for wanting to suck Bolt’s cock. It wasn’t for any sort of lust, but rather to earn a reaction from him. He wasn’t expecting Bolt to be at his hooves begging for another blowjob, but he wanted more than nothing.

So for the last time, he reached out and took the whole head into his mouth, instantly filling so much more space than he thought it would.

From the brief lessons he had learned from marefriends when he had asked them how they had done it, they had said that sucking a dick had less to do with actual suction than one would think. And there was one particular trick to protect against teeth, with the tongue covering the bottom row while the upper lip covering the top.

He followed the instructions in his head, covering his teeth and making sure not to suck. Then he started working his tongue around the shaft, and every once in a while bringing it in to massage the very tip of it. Finally, when playing with the tiny hole at the front, he earned a gasp from Bolt.

“B-buck, that’s awesome.”

Button glowed with pride, almost dismounting himself to thank him for the compliment, but then thinking better of it. He was doing well. Why stop when on a roll?

He pressed himself further and further onto the cock, pushing it deeper into his mouth. Something solid met his lips, and he backed up slightly, trying to get a good look at it. The medial ring. He was only halfway. He leaned into it, pressing his lips against it like some sort of strange kiss (although, he guessed that this whole thing was a rather strange kiss), and took note of just how full his mouth was at the halfway mark. It was hard to tell exactly, but it was definitely near the back of his throat now, making him gag every now and then when he bobbed down just a bit too far, too fast.

Button decided to go for it. If he didn’t he knew he’d regret it. When mares were able to deepthroat him, it always felt amazing. He wanted to give that same feeling to Bolt.

Button opened his jaw as far as it would go and attempted to get past the large bump that was the medial ring. Bolt gasped, undoubtedly feeling the pressure of Button’s untrained maw trying to swallow something so wide. Bolt held still against the onslaught, making sure it was Button who was going forward, and that he wasn’t forcing anything on him.

But Button couldn’t do it. He pulled back until just the tip remained in his mouth, panting around the cock, refusing to let go of all of it but still needing a break. A moment later, he tried again, spearing himself on the length and desperately pushing against that barrier, trying every way he could think of to fit it in his mouth.

Bolt was surprised at his old classmate’s vigor. He held on to Button’s shoulders tighter, fighting against every instinct in his body to force the rest of it in. He didn’t want to hurt Button, nor hurt his relationship with him, but with his tip at the back of his throat and his ring being assaulted by lips and tongue, it increasingly got more difficult to hold back.

Button pulled back excruciatingly slowly, and Bolt thought that he had finally given up, resorting to giving him a blowjob on the lower half like most of his other coltfriends had done. He breathed out a sigh of relief, glad that this would be going on for several more minutes, finally able to relax his limbs and enjoy it again.

But then, without warning, Button shoved his head down again, and Bolt met him with a strong buck.

All at once, the ring made it past Button’s teeth, and Bolt’s now-flaring head had made its way into Button’s throat.

Button could dully feel a bit of pain in his teeth, and in general his entire jaw was tired of being held open all the time, but more pressing of an issue was the cock lodged in his esophagus. He gagged harshly, trying rather unsuccessfully to swallow the head and get rid of it.

Relax, he told himself. Just focus on sucking dick. Try to ignore the fact that you can’t breathe anymore. He was thankful he took a deep breath before diving in. There were enough attendants around that Button felt safe even in this predicament, but he didn’t want this fun to end so quickly.

He didn’t have much room to maneuver backwards, so he was forced to go even deeper. Before long, he had impaled himself entirely on Bolt’s cock.

Bolt let out a long, quiet moan, and started petting Button’s mane. “N-nopony’s ever taken all of me b-before…” It was obvious that he was savoring the moment, especially when his hooves stopped petting and instead held his head in place while he ground his crotch against Button’s muzzle, making sure he got every last bit of himself inside Button as possible.

Silver Wing took this as the perfect opportunity to pull his length free of Button, which made him make a noise somewhere between a yelp and a moan around the cock at the unexpected stimulus from his behind. The weight of the stallion was removed from his back, and Silver stepped away, leaving Button once again open to the elements, and for anypony else to see the evidence of what had taken place there.

“Not my best work,” Silver said, running a hoof over Button’s cutie mark once again. “You were great, though. A tight ass that I had the pleasure of stretching out.”

He walked up so that he was next to Button, watching his face closely as he struggled to focus on both Silver’s words and Bolt’s cock. By now, Bolt was slowly rocking his hips back and forth, wanting to elongate this as much as he could before he came, but also making sure to finish before Button ran out of air.

“You’re pretty cute, Button. I hope to see you around here again.” Silver set a hoof on Button’s mid-back, then turned and left. Button wanted to say goodbye or wish him well but, as he was unable to do so in his current state, returned his focus wholly on trying to give a better blowjob while also trying to ignore the slowly building burning in his lungs.

And with that extra focus, as well as the immense length that had somehow fit inside Button, Bolt was ready to blow his load in no time.

He gave a brief warning to him, “H-hey, Button. I’m gonna cum, ok?” Bolt’s back right leg was shaking slightly, and Button could feel the thrusts becoming both stronger and more erratic. There was nothing he could do with the warning, only prepare himself for the inevitable.

Instead of just waiting, Button went all out, flicking his tongue around the pulsating rod, pushing and pulling on his own, even humming, easily sending Bolt over the edge.

“B-B-Button!” he screamed as he hilted in his muzzle, pressing Button’s nose deep into his fluff and slapping his balls against his chin while Bolt’s dick reached even further down his abused neck. Button felt the tightening of Bolt’s balls first, felt the slight expansion of his dick as the cum shot through it, before finally feeling it pass through and flood into his stomach, hardly even needing to swallow it at all.

Button continued to massage the shaft with his tongue, almost trying to guide the cum along its journey into him, feeling it pulse and twitch.

Pleasure had been building inside Button, and feeling Star’s semen flood into him was just that little bit too much. His vision went blurry and his body became numb as he came for the first time that day, his balls churning and pulling into himself, shooting cum through his throbbing cock, each spurt coating the back of the box in his liquid lust.

Bolt’s orgasm eventually ended, but he stayed hilted while he slowly softened, which somehow felt weirder than anything else Button had experienced that day. He tapped Bolt on his cutie mark, to which he responded with a quick apology and quickly (perhaps too quickly) pulled himself all the way out of Button with a loud and wet Pop!

“Ghah! Bwuh… Huh…” Button was exhausted. He couldn’t quite figure out how to form words just yet, still too used to accommodating for the large cock. He worked his jaw around a few times, but nothing seemed to be helping just yet. He was gonna give it a minute or two. Or three. Or more.

“Oh gosh, I’m so sorry Button! I really should have told you to just stick with the top half earlier. Would have saved us a lot of trouble, and you a bit of pain. I mean, I couldn’t even pull out because of your teeth! I was afraid I’d rip ‘em out with my ring or something. I had thought that I would have knocked a few teeth out going in, but…” Bolt leaned down to Button and moved each of his wings’ primaries into the corners of his mouth, pulling them down and around to check for damage. “It doesn’t seem like we did anything too bad in there, which is good. If you’re gonna keep this sort of stuff up today, you should probably be careful with that sort of thing. Ok, Button?”

“Juh.”

Bolt took that as a yes. Then, while he was still on Button’s level, he kissed him once again. It was far more sloppy than the first one, as both were tired from that ordeal, but it was somehow far more passionate. Bolt noticed something peculiar, and then pulled back.

“Did you not get any cum in your mouth?”

“Nuh… Don’t… think…”

Bolt ruffled his hair. “Don’t tire yourself out, dude. Rest a bit. You’ve earned it, especially after swallowing everything. I mean... just wow. I cum a lot, you know.”

He got a look from Button that, despite everything, clearly said “No shit.”

Bolt rubbed the back of his neck as he got up. “So, uh, I guess you’ve got ponies to do, and I’ve got places to be, so I guess I’ll see you around, eh?” He waited to see if Button would respond.

“See… yuh.”

And with that final goodbye, Star Bolt took off into the sky, flying out of the Manehattan Marketplace, and leaving Button to busy himself with the rest of the city.