Author's Note

Contains: casual sex, public sex, groupsex in the background, gloryhole, anal, spitroast, loss of virginity, culture shock. Now with fixed import weirdness.

The Observations of an Equestrian Non-Native on Equestrian Societal Norms (casual sex, first time)

Equestria is a different place.

When Ke'eliene had boarded the train, frantically waving goodbye to his entire village, he was not prepared for just how different it really was.

Growing up in a moderately sized village in the heart of Zebrica, Ke'eliene had lived a fairly standard life. He’d gone to school, helped around the village, gotten a mentor, the usual for a village Zebra like himself. He’d visited the nearby city a few times and had even seen a few denizens of the neighboring nation of Equestria. How they were all so colorful, he didn’t know. A couple of the brightly colored ponies had even visited the village, though they never stayed for more than a couple of weeks.

After graduating the twelfth grade, Ke'eliene was approached by one of the village elders with a pamphlet they’d received in the mail. Apparently, Equestria had an outreach program where they took fifty students from each nation and gave them a full-ride scholarship to an Equestrian university of their choosing. Figuring he might as well, he applied for the Manehattan University.

He never expected his application to go through.

Only a month later, he found himself holding back tears as he bid everyone he’d ever known goodbye, the conductor shouting a last call through the smokey haze. Scrambling onboard before the train left him, he found the closest window and continued waving until he couldn’t see them anymore. Sitting down, he prepared for what was to be a multi-day journey to Manehattan University, and a new life beyond that.

Ke'eliene blearily opened his eyes as the train rolled into the station, sitting up a little straighter in his seat. He’d watched excitedly out the window as they passed a colorful sign that proudly proclaimed, “Welcome to Equestria!” in a font easily legible in the predawn light. That had been hours ago though, and now the poor sleep he’d gotten on the moving train was catching up to him. Blearily glancing around the half empty train car, he watched as an elderly Zebra stood up, hobbling out the doors as soon as they had opened. With curious eyes, he watched as a group of six ponies about his age walked into the train car, excitedly talking amongst themselves as they sat down in the booth in the corner. The group, primarily Earth Ponies with a single Unicorn, was made up of four mares and two stallions, all of them casually brushing against each other in a way that made Ke'eliene blush. He’d heard that Equestrians were more open in their affections, but this was about as blatant as it got. He didn’t understand which ones were the couples though, they all seemed to brush against each other equally. Trying not to stare, he looked back at the single book he’d brought, though he’d finished it yesterday.

His eyes were drawn back up as the conductor entered the car. “We’re filling water, so we’re gonna be at the station for another ten minutes. If any of you need to use the facilities, now is the time.”

Eyes widening, Ke'eliene jumped up, quickly trotting out onto the platform, glancing around until he spotted the restroom sign in the corner of the station. Entering the restroom, he frowned slightly. It was the second one he'd seen that was what he was starting to dub ‘Equestrian style’. Instead of small cubicles with floor to ceiling walls, there were instead a series of urinals sunk into the floor with small dividers between them. Standing over one of the urinals, he dropped out of his sheath and began to do his business, though he regretted it almost immediately as the door was suddenly flung open, the clattering of hooves sounding on the hard tile. Biting his lip, he clenched his eyes shut as the hoofsteps slowed to a stop behind him.

“Damn, dude! You got quite the pair!”

Never before had he regretted his choice to cut his tail traditionally short, his sudden hyper-awareness informing him of the gentle breeze across his fuzzy, rounded orbs as they dangled in plain view. Unconsciously, he clenched, causing the black orbs to jump in his sack.

The pony behind him whistled at the sight before trotting off to the stall at the end.

Cleaning up as quickly as he could, Ke'eliene bolted out of the restroom before trotting back to his seat on the train, trying to hide his embarrassment. A few minutes later, one final pony boarded just before the doors closed, the train lurching back into motion moments afterword. Seconds later, a shuffling noise in the corner of the cabin drew his attention back to the group he’d completely forgotten about.

What he saw froze him solid. Two of the mares had gotten up and turned around, presenting their hindquarters to the stallions, and by extension, the rest of the car. With gusto, the stallions leaned in, each lapping eagerly at a different hole, the one licking the Unicorn mare’s tailhole shoving his tongue in far enough to wrap his lips around her wrinkled ponut. A slight groan brought his attention to the carpeted floor where the final two mares were busy licking at each other’s hind ends, tongues dancing from clit to dock and back again.

Finally broken from his stupor, he glanced around the train car to see the looks of shock and embarrassment only to find none. The stallion in the booth next to his was reading the newspaper, two older mares had pulled out knitting needles and had gotten to work, and to Ke'eliene’s surprise, there was another couple going at it in another booth, the mare’s head bobbing at the stallions crotch.

He glanced back at the group just in time to watch one of the mare’s back onto the stallion’s rock-hard shaft, sinking down to the base in one go before bringing her hips back up for another thrust. The Unicorn shuddered in bliss as the stallion rimming her out hit a particularly sensitive spot.

Unbidden, Ke'eliene’s shaft spilled out of his sheath, hardening in seconds at the brazen display.

“You’re staring.”

Ke'eliene jumped, tearing his eyes from the erotic display to look at the stallion as he set down his newspaper. “You’re from Zebrica, right?”

Ke'eliene could only nod mutely, still rosy cheeked and diamond hard.

“Things are a bit different here in Equestria, as you may have noticed.”

And so Ke'eliene spent the next hour and a half getting a crash course in Equestrian culture from the stallion, who he learned was a businesspony that negotiated shipping arrangements between industrial firms. The Zebra’s erection never did go down, the constant buffet of sights and sounds from the corner of the car keeping him near painfully stiff, the group constantly switching positions and holes and partners, the two stallions even taking turns at each other on occasion.

What he managed to learn from the stallion despite the distraction both caused his mind to erupt in fantasy and his heart to fall.

Apparently, what was happening in the corner was normal.

In Equestria, sex was a casual affair, though it was generally kept between close friends, or at least good acquaintances. It was considered a bit rude to block traffic or to leave a mess, but those were pretty much the only stipulations. In the corner of a coffee shop? Sure. In a dark back alley? Go ahead. In the reference section of the library? Just as long as you stay quiet and don’t make a mess. The group of ponies currently shoving their tongues up each other’s plot holes were maybe being a bit loud, but they were still well within the bounds of socially polite.

As for Ke'eliene himself, watching was fine, though you tried not to stare. Even his raging hard-on was okay, it was considered a complement in most circles, though some would view it as a lack of restraint and others might even interpret it as asking to join. Randomly popping a stiffy in a truly public place was something you tried to avoid but was regarded as a fact of life.

As a personal note based on… observations, pony stallions didn’t last very long, but they also didn’t seem to have much of a refractory period, maybe a minute at most. Also, from his experiences in the bathrooms back home, he knew that he… produced a bit more than they seemed to.

Hours later, Ke'eliene practically exploded out of the train car at the Manehattan station, though he instantly regretted it as his rock hard, and slightly painful at this point, erection audibly slapped against his belly. Spotting the bathrooms across the busy station, he nimbly dodged and weaved through the crowd, trying to ignore the not quite stares he drew as his striped coat did a terrible job blending into the rainbow of colors surrounding him. Normally he would be the one gawking, but he was on a mission.

Slipping through the door, he almost let out a sigh of relief until he saw the two ponies in front of him.

The two stallions looked up at him as the one pounded into the other, this bathroom lacking even the privacy dividers between urinals that the last bathroom had. Ke'eliene simply stared as the bottom stallion groaned, his mottled cock flaring as he fired his load into the urinal beneath him. The top stallion looked up at him questioningly, “Oh. Is the Eastern Line in already?”

Ke'eliene only nodded mutely, trying to ignore the sight of the top stallion’s balls bouncing gently as he unloaded into the bottom stallion’s trembling backside.

Trying to trot smoothly so as not to make his rock hard and trembling length smack too loudly against his stomach, he sought the closest thing to privacy the room had to offer, slipping into one of the sit-down stalls. Closing the door behind him, he glanced down at his crotch, finally realizing how close to orgasm he really was, his flared length bobbing in the cold air with every heartbeat. Ear flicking, he heard an unmistakable popping sound followed by two grunts. Having heard that pop several times on the train, his overstimulated mind gave in and he came without ever having touched himself.

Rope after rope of thick cum splattered into the bowl of the toilet, only his quick thinking preventing it from simply arcing across the stall and into the wall beyond. Even as his aching balls bounced and jiggled behind him, he could only stand paralyzed at the deafening noise of each shot from his wide urethra impacting the porcelain beneath him. With a dribble, his orgasm finally subsided, allowing his aching length to finally retreat. Turning around to sit, he listened as the faucet ran for a minute before two sets of hoofsteps retreated, the bathroom door swinging open and then thumping closed.

Relaxing for the first time in what felt like hours, he glanced around the stall. Oddly, on the wall was a small chalkboard with some chalk and an eraser in a plastic tray next to it. The board was blank at the moment, though it looked heavily used. A small way down, he saw a hole in the wall, about twice the size of his hoof. The hole looked purposeful though, being lined with the same shiny steel trim as the rest of the stall. Glancing at the opposite wall, he saw an identical hole, though this one didn’t have a chalkboard next to it. Instead, it had what looked like a soap dispenser mounted nearby.

Try as he might, he couldn’t puzzle out what the holes were for, so he turned his attention to the rest of the stall. Eyes alighting on the door latch, he noticed that it had more than just two positions labeled.

Open, Occupied, Giving, Taking

In his haste, he had set the latch to Giving, though he had no idea what that meant in the context of a bathroom stall. He wasn’t given any time to ponder it though as the door squeaked open, a single set of hoofsteps walking towards the line of stalls. Stopping in front of his stall, a mare’s voice let out a quiet cry of triumph before she trotted into the stall next to his.

“My ass, please. I wanna feel you fill me up.”

With a start, Ke'eliene watched as the hole to his left had a pair of purple cheeks press against it, the mare’s tailhole perfectly centered in the silver ring. Though it hadn’t been more than five minutes since he’d cum, his length knew what it wanted, extending from it’s sheath and hardening in short order.

“Don’t worry about foreplay, though do remember to lube yourself. Though if you wanted to give it some love first, I wouldn’t mind. My train doesn’t leave for another forty minutes.”

Ke'eliene glanced at the dispenser on the wall that he figured held the lube in question. Glancing back at the mare’s plot pressed against the stall wall, tailhole winking in excitement for what was to come, he made his choice. The village he had grown up in might not understand, but this wasn’t rural Zebrica. This was Equestria, and though he was still new here, he was starting to understand.

He was a consenting adult. She was a consenting adult. He had something he could give her. She had something she could give him. What else was there to understand?

Squirting a small dollop of lube into his hoof, he brought it up to her waiting tailhole, though he paused just before contact. Was he really going to lose his virginity in a train station bathroom to a mare he hadn’t even seen? Looking hard at the soft ring of flesh lewdly winking at him, wrinkled flesh contracting every couple of seconds, he thought about the mare it was attached to. She had come into the bathroom looking for some quick pleasure before the train arrived, hoping to find a warm dick waiting for a ready hole. What she had found was a foreigner with no idea what he was doing, door latch accidentally set to Giving. Was he really ready to give that part of him?

Ke'eliene had always been the shy sort, having never even thought about the possibility of ever even going on a date, let alone having any kind of relationship. One of his fears had always been that he would underperform in some way, alienating the poor mare with his lack of conversational skills or forgetfulness. And yes, he was worried that he would underperform in the bedroom.

This was different though. This mare had never seen him, knew nothing about him, and was about to leave on a train in forty minutes. He wouldn’t have to hold a conversation. He wouldn’t have to remember anything about the mare once she had left. He wouldn’t need to be an attentive partner in a long-term relationship. The only thing he had to worry about would be his ability to pleasure her, and if he failed, the worst that would happen would be the mare leaving the bathroom unsatisfied only to find another bathroom later to get somepony else to take care of her itch.

“Hello?”

Mind made up; his hoof made contact.

The mare gasped as the cold goo made contact with her sensitive flesh, tailhole clenching tightly for a moment. Ke'eliene gently rubbed the protruding ring of muscle, marveling at how soft and stretchy it was. While it wasn’t the first time he had seen under a mare’s tail, it was certainly the first time he had touched it. He had never imagined touching a mare’s tailhole until now though. What little he had learned in his village pointed towards the vagina and nothing else, though the few hours he had been in Equestria had more than proved that the tailhole was not only capable of taking his length, it looked like it was rather pleasurable too.

A soft moan on the other side of the wall as he used the tip of his hoof to stretch the presented hole slightly only proved that point. Deciding that he had gotten her tailhole as prepared as he knew how, he squirted out a second, larger dollop of lube and hastily, though thoroughly, lubed his black length.

Bracing himself against the wall as best he could, Ke'eliene awkwardly tried to line up his turgid shaft, poking against her dock a couple of times before he shifted his hind legs slightly. Finally pressing against his target, the first thing he noticed was the incredible heat. Pressing gently so as not to hurt the mare, her incredibly hot ring slowly opened to admit the flat head of his shaft.

If the feeling of warmth from her muscled ring was incredible, the burning heat of her insides blew that all away.

As the first few inches of his shaft sank into the tight confines of the mare’s ass, Ke'eliene was in bliss. He’d stroked himself off before, more times than he’d like to admit, but it was nothing compared to the heavenly grip surrounding his tip, rhythmically squeezing and massaging him as if it wanted him to press deeper, to envelope more of his shaft in her depths. The long, drawn out groan of pleasure from the other side only heightened the amazing feeling washing over him.

Pausing to shift his balance, he heard an appreciative murmur from the mare. Hoping he was doing the right thing, he continued pressing forward, slowly sinking into her until his medial ring bumped into her straining tailhole.

Adjusting his stance once again, he heard the mare mutter “Ohh... Don’t worry about being too rough. Give it to me.”

Emboldened, he pushed his medial ring into her.

“OH! That wasn’t your sheath? You’re huge!”

Concerned, he paused again. He’d known that he was a little longer than the stallions on the train, but he thought that maybe they were just on the smaller side. Maybe he should pull back out a little so he wouldn’t hurt her?

As if reading his thoughts, the mare clenched down on him. “Don’t you dare pull out now! I want that entire thing buried deep in me.”

Biting his lip, Ke'eliene resumed burying his apparently formidable length into the hot confines of her quivering ass. Her moans of approval only grew louder with every inch he sank into her. A couple of inches before he bottomed out, the texture of her insides changed, his tip pressing into a tighter, slicker area deep within her. He feared once again that he had hurt her as she let out a deep groan. He was about to pull out when she moaned, “Oh Celestia yes! Soooo deeep!”

Biting his lip, he once again pressed forward, finally sheathing his entire length in the incredible heat of the mare’s clenching tunnel. The mare let out a gurgling moan as he began to pull out, her breath hitching as his medial ring tugged her tailhole along with it for a moment before it popped out. Pulling out till the back of his slightly flared tip rested just inside her clenching ring, he paused for a second, readjusting his stance again.

“Please. I need it.”

Ke'eliene complied eagerly, sinking to his sheath in one smooth stroke, though he jerked out a little faster than he intended as his balls brushed against the shockingly cold stall wall. The mare didn’t seem to mind though, her tunnel gripping against his length as he pulled back, exposing just the slightest hint of pink against his pitch-black length.

Not pausing this time, Ke'eliene thrust forwards, burying his length once more into the confines of the strange mare’s tailhole, drawing a lusty moan from her. It didn’t take long for Ke'eliene to find a rhythm, long smooth strokes slowly becoming faster and shorter, the mare’s breath hitching every time his turgid length went extra deep, the skin of his sheath pressing against her tight ponut.

With a squeak, the bathroom door opened again, though Ke'eliene was too focused on the sight of his shaft disappearing into the muscled ring of a mare he’d never met and the sounds he could get her to make by shifting the angle of his thrusts to notice. He did notice when those beautiful moans were suddenly muffled, replaced by sloppy grunts. His thrusting slowed in bafflement as he tried to figure out what was going on before he remembered what those noises reminded him of. The mares -and stallions- on the train had made those exact sounds when they had a dick in their mouth.

Figuring that some stallion had come in and was using the hole in the other wall of the mare’s stall, he decided that it didn’t matter. He wouldn’t be able to make the mare make the same sounds as before, but he’d already figured out most of the angles that caused them, so he went back to humping away.

To his great surprise, as soon as he had buried his length to the hilt once more, the mare’s tight tunnel suddenly got significantly tighter, locking him in place as the muscled interior of her rectum milked his length in a rippling motion, accompanied by a set of loud grunts.

A goofy grin slowly spread across Ke'eliene’s muzzle. He’d just given a mare an orgasm, from her butt no less!

A few moments after her orgasmic clenching had passed, she wiggled her butt a little, giving Ke'eliene the go ahead to start thrusting again.

Ke'eliene had other ideas though. Pulling fully out with a loud pop, he dropped back onto four hooves to get a better look at what he’d done.

The sight before him burned into his young mind, forever altering his sexual preferences in a single moment. The quivering ring of purple flesh was the most beautiful thing he’d ever seen. The harsh bathroom lights reflected off the shiny wrinkles of her muscled ring, perfectly framing the pink insides of her gaping ponut. He had done that. Ke'eliene had reduced the mare’s tailhole to a quivering mess, gaped open as deep as the eye could see in the act of bringing her to the heights of pleasure. As he stared at his conquest, his stallionhood achingly hard, he acted on impulse. Bringing his lips to the presented ponut, he ran his tongue around the ring of flesh, each wrinkle in the soft, pliable skin committed to memory.

The mare groaned in slight confusion, not expecting the stallion that had been happily pumping away deep into her ass to stop, let alone start eating her out, though she found she didn’t mind as his thick tongue pressed into her, the bumpy texture stimulating her oversensitive ring just right in the aftermath of her orgasm.

Ke'eliene was in bliss, his eyes rolling back as he explored every inch of her clenching tunnel that his tongue could reach. His new favorite part of a mare was before him, and he could do anything he wanted to it. He was free to explore its depths, tongue wiggling into every nook and cranny. The hint of peach flavoring from the lube only heightened the experience. He had a mare in front of him that would happily take his entire length into the tight confines of her taboo hole, and she seemed just as happy with letting him play with it. Pulling his tongue back out, he focused on licking off every drop of the peach flavored lube he could find, dragging his wide tongue from her perineum up to her dock, savoring the flavor for a moment before diving back in. Homing in on the clefts between her protruding ring and the cheeks surrounding it, he swapped back and forth between the two, noting how her ponut would draw tight with each enthusiastic lick before relaxing back to its slightly gaped state. After giving some attention to her wiggling dock, he couldn’t resist anymore, his tongue piercing her winking hole with no warning.

Pausing to let his tongue rest for a moment deep within her rectum, he heard the stallion on the other side of the mare for the first time, the wet slurping sounds stopping as he let out a muffled groan. For a moment, a vision of the stallion’s spunk erupting from the mare’s tailhole flashed across Ke'eliene’s mind, though his rational mind reminded him of the impossibility of the idea. With a wet slorp, the mare’s moans were suddenly unmuffled again.

“Mmm. You’ve been eating your pineapple, haven’t you?”

The stallion didn’t seem to respond, the sound of the toilet paper dispenser and a flush echoing around the tiled walls as a clattering of hooves and the squeak of the door announced his sudden departure.

“Huh. Must’ve been late for something. Now, I appreciate you taking it easy on me while I was sensitive, but I know you didn’t cum yet, and I want your seed painted so deep inside of me that I can taste it. With how long your tool is, you might just be able to pull it off too, so get back to it.”

Almost reluctantly, Ke'eliene withdrew his tongue from her ass.

“Lube me back up, stud. You’ve gone and licked all the old lube off, though I don’t blame you. Manehattan gets the good stuff.”

Sheepishly squirting another dollop onto his hoof, he carefully rubbed it into her waiting hole, making sure to get plenty of it inside. Lining up his still hard shaft with his new favorite hole, he sank back into her velvet depths. Quickly returning to his previous rhythm, he went back to seeing what angles got her to make the loudest groans, though with her mouth unoccupied, she was more vocal with her feedback.

It was only a few minutes before her breath began to hitch again, her muscled depths milking his length as her second orgasm neared. “I’m about to cum again. Oh! Oh yeah. That’s the spot. You gonna cum with me? I want you to cum with me.”

The tingling in the base of his shaft told Ke'eliene that he was close enough that he just might. Switching up his rhythm, he started hammering into her experienced rear with a series of short thrusts that just barely pulled his medial ring from her tailhole before plunging back in up to his sheath. At the new pace, his rapidly approaching orgasm teetered on the edge of release, his flat tip flaring out to the width of one of his hooves. That proved the tipping point for the mare, her muscled ponut once again gripping against the base of his shaft tight enough to stop him in his tracks. The mare’s rectum clenching against him in rolling waves mixed with the feeling of her spasming ring trembling against his sheath was the final straw, the most powerful orgasm of his life ripping through him, his balls clenching tight as they pumped their load past the constricting ring of her tailhole to paint her insides white. And he just kept cumming, the wide flare at the end of his rod effectively sealing against the walls of her colon, his seed having no option but to flood deeper into her depths.

“Oh Celestia! It’s so much! I can actually feel it going into me.”

As his orgasm tapered off, stars still filling Ke'eliene’s vision, the mare pulled forwards, unceremoniously pulling off of his length with a plop as the last couple of feeble shots dribbled from his tip. Ke'eliene jumped as a different feeling enveloped his rod, the experienced mare effortlessly swallowed his length in one go. Looking down, he watched as her muzzle poked through the hole in the stall, her tongue rolling out of her mouth to lap at his fuzzy sack. With an incredible pulling sensation, she sucked the last of his cum from him, rolling his hefty balls with her tongue as she did so. Pulling her tongue back, she formed a tight seal with her lips and withdrew, leaving his length nearly spotless as she popped off his tip. With one last kiss to his slightly protruding urethra, she audibly swallowed.

“Ahh, that’s the stuff. Tangy. Well, that was a lot of fun! You did great for your first time! I actually came twice, so you did better than I was hoping for. You’ll make some lucky mare very happy with that someday.”

And without another word, the mare trotted out of the bathroom, the squeak of the door hinge followed by it slamming shut again.

Ke'eliene silently pulled his softening length through the steel ringed hole, wiping off the last remnants of lube and cum with some toilet paper.

The words of the mare rang through his head. She had called him really good, but had his inexperience really been that obvious? Flushing, he exited the stall and wandered over to the sink. Looking into the mirror, he looked at the reflection of a stallion that had just made a mare cum from her butt twice and decided that it didn’t matter. He’d enjoyed the experience, and she’d pretty obviously enjoyed it. Sure, he’d been a bit hesitant and fumbly at the beginning, but he’d started to figure some things out towards the end, and he was sure that he’d get better with experience.

With a grin, he realized that Equestria and its odd customs would be the perfect place to get that experience too. Exiting the bathroom, he looked around at the land of opportunity he found himself in. Grinning to himself, he trotted confidently through the crowd, excited for the future that awaited him in this land of lustful wonder.