Trouble Rain

by Mister Coffee

Rating: mature
Tags: My Little Pony: Friendship is Magic, Other, Porn, Sex, Troubleshoes, Crossover
Length: 4322

Troubleshoes knows that everymare loves a big stallion . . . but he's unlucky, he's TOO big. Maybe a Saddle Arabian mare would be interested, or maybe for once in his life he'll get lucky.

Troubleshoes is a big stallions, and mares love big stallions. Troubleshoes is an unlucky pony, and he's too big for mares.

In the back of his mind, a Saddle Arabian is an option, but he can't afford boat fare. So he goes on with his life, unlucky and unfulfilled until a freak accident and a chance meeting suddenly change everything.

An entry for the Furry Foray Festival.

Published 2023-01-03 04:00:00 UTC
Last updated 2023-01-03 04:00:00 UTC

Before

Trouble Rain
Badmiral Biscuit

Amongst the earth ponies, nearly every mare wanted a big, strong stallion. That was a fact, that was something he’d been told since he was a colt; that was something that he’d overheard young mares whispering about. That was something his father told him as he got bigger and bigger

And bigger

Until he was his present size.

Deep down, he knew that he was clumsy and awkward and rather unlucky (which might have been caused by the first two problems), and the truth was if he had a marefriend and if he kept her long enough to actually get down to the sex part of a relationship, he’d probably screw that up. Stick it in the wrong hole, or miss entirely.

The closest he’d come to sex—not counting the crook of a forehoof—was the time in Appleoosa when he had a few bits to his name and tried his luck with a prostitute.

She eyed him up and down, then told him to drop his little stallion.

His not-so-little stallion.

“Sweet Luna’s teats, there’s no way that’s gonna fit in my cooch.” She reached out a hoof and reverently prodded it. “That is the biggest cock I’ve ever seen. You should be proud.”

“Ain’t much use to me,” he muttered. “Since nopony wants it in them.” Admittedly, he didn’t know that as an actual fact, having never gotten that far with a mare before. “You could suck it maybe?” Everystallion said a blowjob felt almost as good as actual sex.

“I’m not a snake,” she told him. “I can’t unhinge my jaw to swallow that monster.”

Troubleshoes sighed, accepted a refund of his bits, and wandered back to his cabin, completely unsatisfied.

•••

Equestria was a big land, and he’d heard rumors of ponies nearly his size in Saddle Arabia, elegant mares who wore lacy veils and bridles. He’d seen pictures in magazines, and if he kept working as a rodeo clown long enough, he might be able to afford boat fare to Saddle Arabie in another dozen moons.

He thought about it sometimes. He’d managed to save a clipping from an exotic foreign magazine, a glossy full-page photo of Haakim. Her slender muzzle and chestnut fur—so like his own—her long legs and thin barrel, barely concealed under the decorative saddle blanket she wore. He could only imagine what it would be like to be with her. She was almost as tall as the Princess!

He could save his bits, buy passage on a steamer, and if his bad luck stayed in abeyance long enough for the ship to arrive in Saddle Arabia, he’d have spent all those non-refundable bits to get rejected by every Saddle Arabian mare he encountered, he just knew it.

Or, if he got lucky enough (ha!) the rodeo might decide to have an exhibition show in Saddle Arabia, and then his ticket would be paid for.

•••

As luck would have it, the next exhibition rodeo was to be abroad, but Wrangler wouldn’t say where. Whenever anypony asked, she’d just stick out her tongue and say ‘it’s a secret, and if I told somepony it wouldn’t be a secret anymore.’

Troubleshoes knew, because he’d asked.

Several times.

And he was as surprised as anypony else when Wrangler finally did make the announcement—they were going to Yakyakistan.

Well, yaks were big; maybe he’d get lucky.

•••

There were a few stars in the rodeo, and they got their own rooms on the train. They didn’t have to pack up all the gear and load it onto the train, and they wouldn’t have to unload it when the train arrived in the next town—or Yakyakistan.

Troubleshoes wasn’t a star. He did get his own room, but only because he was so big.

He was settled onto his couch/bed, head resting on the windowsill as the train climbed up the mountains leading to Yakyakistan, getting one last view of the land before he settled in for the night.

He’d been paying attention as they’d crossed over the prairies—sometimes he felt like he didn’t belong with the other ponies, but out in the grasslands, living free.

They’d passed a herd of ponies living off the land a few minutes ago. Plain-colored like him. A couple had stuck their noses up as the train chugged by, while the rest had continued eating the fresh, free prairie grass, completely unconcerned.

He sighed and settled back on his couch, rested his head on the pillow and tried to drift off to sleep, his mind as always returning to Haakim and Saddle Arabia.

At first, he didn’t notice the unusual banging coming from just behind him. It was a subtle pulsation, not quite rhythmic, and it didn’t stand out from the normal train motions.

Then it got worse, and came with a creaking noise, and then it got louder and harder to ignore.

Nopony else seemed to have noticed, and he thought about ignoring it himself, but he instead pushed the covers off and opened his door. The car was deserted—tomorrow would be an early day, and everypony on the train was safe in their cabin for the night.

When he opened the door on the vestibule, he could really hear it, and his ears focused down to the coupler. The knuckle was partway open, and as he watched it creaked just a little more open with a puff of rust dust.

I should tell somepony. There was a brakemare in the caboose; she’d know what to do.

They weren’t supposed to visit the caboose; a pony had to jump across and it was dangerous for somepony untrained. Troubleshoes had a broad gait, and he could just step across—

It was just his luck that the coupler failed with an explosive crack as he was mid-step, and he just managed to grab onto the end railing of the caboose as it parted ways with the rest of the train.

His first thought was that he was going to be blamed for breaking the train. His second thought was that he was about to die—first the caboose tried to drag him under as it bled off its forward momentum, then it started to roll back down the grade, bouncing his hind legs off the ties.

Troubleshoes struggled forward, finally managing to pull his body up onto the end platform. He scraped his belly on the rough wooden edges, managed to bang both his sheath and balls against the cut lever, and lost a shoe to one of the railroad ties.

All told, he got off lucky.

The caboose door was locked, which he only realized after he’d broken the latch off.

He’d never been in a caboose before, and he had a moment to appreciate how nice it was. There were several beds, a seat with a desk, a stove, and a couple more seats in the cupola.

The only signs of life in the caboose were a collection of stallion pinups tacked on the walls. None of them were as well-endowed as he was, he noted with some satisfaction.

“Miss?” He’d seen the brakemare before, and he’d expected that she’d stay in the caboose when the train was in motion. Where else would she go?

Did she jump? He hadn’t seen her jump.

Then he caught a glimpse of windblown mane through one of the rear windows and remembered that the caboose had porches on both ends.

He also remembered that there was a brake wheel on one of the porches.

Troubleshoes stumbled on his hooves as the caboose jerked to the side, rocking and tilting like a ship at sea, then it straightened out and continued to rocket down the mountain. He could feel a shimmy under his hooves and a whistling noise he didn’t like as the wind whipped past the car.

He trotted through the car and to the end platform, where the brakemare was frantically trying to spin the heavy steel brakewheel.

“Uh, we came off the train,” he said, mentally face-hoofing the moment he said it—of course she’d know that.

“I know! Help me turn this moon-cursed wheel before we go in the ditch!”

Troubleshoes nodded and grabbed hold.

Even for him, it was stiff—she wouldn’t have had a chance.

He leaned in and pushed and the wheel didn’t budge. “Stubborn thing,” he muttered, and set his hind hooves as best he could on the rocking porch.

Up ahead, another curve. He gave up his attempt and held on for dear life as the caboose rocketed around the turn, tilting enough to shear off pine fronds before it settled back on its suspension and roared onto a trestle.

Troubleshoes braced and jerked his back and the wheel protested but started to turn.

•••

The caboose finally rolled to a stop in the foothills, its brake shoes smoking. Both ponies breathed a sigh of relief.

“I thought I was a goner,” the brakemare admitted. “I was gonna join the birds, but by the time I got down from the cupola we were on a trestle, and when we got off, we were going too bad. I thought I’d be in the ditch for sure.” She nuzzled him. “Good thing you . . . where did you come from, anyway? You’re one of the rodeo ponies.”

“I was gonna warn you about the coupler, but just my luck, I was too late.”

“You were just in time.” She looked around. “Okay, they’ll figure out we’re gone sooner or later. I’m glad you’re here, that’ll save me some wear on my shoes. I need you to take a couple torpedos and the shiner down that way to protect our caboose, in case another train comes along. I’ll head up the mountain to meet up with the rest of the train, or if they’re still going, I’ll send a message at the next telegraph shack.”

“Torpedoes? Shiner?”

The brakemare nodded, and started pulling equipment out of a cabinet. The lantern, he recognized, but the flat discs with straps were a new thing. “These are torpedoes,” she explained. “Walk a mile or two back and clip them over the rails; if another train comes along it’ll set them off and they’ll know to stop. If you don’t have the torpedoes down, wave the lantern. You think you can do that?”

Troubleshoes nodded.

“Once you have the torpedoes in place, you can come back here and wait until the train comes back.”

“Okay.”

•••

Trouble Shoes was a clumsy, unlucky pony, but he wasn't a stupid pony. It might have been easier to walk on the tracks, but a train could come along and squish him, so he walked in the grass alongside.

He had no idea he was being watched.

Author's Note

(Haakim was also a stallion, but Troubleshoes didn’t know that.)

During

Rain didn’t lift her muzzle for trains anymore, they were common enough. Sometimes when they were close enough, she could smell the stink from the locomotive and the faint scent of the ponies on board. They were no threat, they stayed on their tracks and followed them, undeviating.

Some of the younger horses in the herd didn’t know that, and would watch or stomp their hooves or gallop off in fear and she watched them in contempt.

A stallion walking along the tracks was worthy of her attention. Ponies stayed on trains, they were small and soft and she didn’t like them very much. This one was big, nearly horse-sized.

She watched as he scrabbled up the loose gravel embankment to get to the rails. That was dangerous, trains were big and moved fast and were best only seen from a distance. Tracks should be crossed quickly, and yet he had his head down by the rails—fearless!

He didn’t notice them until after he’d done his business on the tracks, and then he took his lantern in his mouth and slid his way back down to the grasses. Rain’s ears flattened as he set the lantern down. Fire was dangerous; fire didn’t want to be kept or contained. Fire would rush across the grasslands and char their food and anyhorse beguiled by it.

She snorted, a danger signal, and more heads rose, all watching the strange pony.

Rain flared her nostrils, trying to catch a scent of him, wondering if she should whinny or not. Caution won out, at least for the moment.

He had his head down in the sweet grass, and she watched him eat, then she watched as he picked his lantern up and walk back the way he’d come.

The stallion was leaving, the herd was safe, she should have felt happy but he intrigued her and she decided to follow him and see where he was going.

•••

The rest of her herd hadn’t been happy, but she was the boss mare and she got to make the choice.

Sometimes she missed the chase, missed working with Little Creek. He saw things in a different way than she did. Those days were gone; he was worlds away.

Was her quarry nose-blind or was he bold? He hadn’t turned back, didn’t know she was trotting along his trail, the rise of the railroad to her right, the mountains ahead rising to the clouds, and him, silhouetted by his lantern.

Rain kept up an easy lope—she was gaining on him, and there was no rush. Whiffs of scent drifted back and they intrigued her; he wasn’t like anypony or anyhorse she’d smelled before. Strange and exotic . . . she felt the first tremble in her loins and quickened her pace.

They kept their distance from the mountains, usually. The ground was uneven, unsure underhoof; the grass was sparse, and rocks and trees blocked view. She wasn’t scared of mountains—and neither was he, apparently.

His scent was getting stronger, clear even over the stink of kerosene. Why did he need the lantern? Was he night-blind?

Rain snorted, and saw one of his ears swivel back, then turn forward again.

I’m out here chasing the world’s most oblivious stallion. She sighed. Stallions were like that. What next? Let him get away? Follow him into the mountains? Cut him off?

He stopped and turned, his face suddenly highlighted by the orange light of the lantern. His ears swiveled and then focused in her direction.

“Is anypony out there?” He lifted the lantern and shone it around, stepping back as she stepped into its arc. “Um, hello.”

She didn’t reply, and continued to move forward, her eyes locked on his. Would he back down or would he challenge her?

He backed down, taking an uneasy step before he straightened, his eyes going wide as he got a good look at her.

The two circled, studying each other. At some point, Troubleshoes set the lantern down so he could sniff her. She pushed him away and whuffed out a warning, cocking a hind leg. Rain felt the familiar longing in her loins, but she wasn’t sold on this pony just yet. Especially not if he wanted to try and lead her up into the mountains. She wasn’t scared of mountains but she preferred to keep her hooves on level ground.

He’s interesting but is he worthy? Her tail was already damp with arousal, and she turned and whipped it across his face. If you want me come and get me.

Her hooves dug into the familiar soil, and a moment later he followed, leaving his lantern behind. She focused on her pace, that momentary feeling of flying as all four hooves were off the ground, the grass skimming against her belly. The beat of her gait, her mane and tail whipping in the self-generated wind.

And he followed, his pace clumsy at first and then falling into rhythm as he found his gait, almost keeping up with her. He was strong and bulky and his hooves made a satisfying thump on the ground as they landed and she unconsciously started to match her pace with his.

The pair ran for miles, far away from the mountains and the railroad tracks and anything that the ponies had built or explored; the pair of them ran through the grass and the moonlight. They ran along the edge of a river valley, cut through the foothills and Rain knew where it widened and flattened on the plains proper.

She kept her tail flagged and he doggedly followed until they got to a copse of trees, a spot she knew well.

There was a pond there and she splashed into the water, letting it cool her, let it wash off the sweat and grit; she went down and rolled as he waded in and then the two of them shook off and stood on the bank and looked up at the stars and the moon until she could wait no more.

This time she let him get close, let him nibble at her withers and run his muzzle down her back. She flicked him with her tail as he leaned in and sniffed her. Rain watched his dick slowly slither out of its sheath and swell and stiffen and when he was hard she turned and shoulder-checked him.

It took a moment before he realized he should be on his back, a few prods with her head before he got into position.

Rain didn’t move in right away. Instead, she studied his cock, standing proud in the moonlight. As thick and almost as long as her foreleg, ever so slightly curved along its length with a wide, flat head: just what she needed.

“Are you—” he began, and whatever he was about to say was lost as she ran her tongue along his shaft, starting at his glans and ending at his balls, then she kissed her way back to his tip.

Satisfied with her initial exploration, she took him between her lips, taking a moment to reflect that this was the biggest cock she’d ever sucked.

•••

At first, Troubleshoes couldn’t believe this was actually happening to him of all ponies. She scared him, tempted him, and then made him chase her and now—

He’d fantasized plenty, but it turned out that his imagination had nothing on reality. Being on his back was weird and vulnerable, and hot as hell. He’d always fantasized he’d be on top but so far being on the bottom was so much better. Not only the sensation of her lips and throat wrapped around his cock, the gentle tease of her teeth, or her tongue slathering his shaft; not only the heady scent of her arousal filling his nostrils, but he had a front-row view as she bobbed his knob, his pre-cum and her saliva intermingled in the moonlight.

Every time she deepthroated him, he felt her hot breath on his balls, yet another sensation he was entirely unprepared for.

Troubleshoes was normally an unlucky pony, and if he’d prematurely ejaculated, rolled over, and then fallen asleep, it would have surprised nopony. This time, the pure impulsiveness of it tilted the scales in his favor, and he just laid back and enjoyed the sensations, at least until it occurred to him that he ought to do something for her. Here he was just lying here, but a proper gentlestallion would be thinking of her pleasure.

Not that he had much idea what mares liked. The one porn film he’d guiltily watched really hadn’t covered that at all.

Once again, fate smiled upon him. Rain stepped over him, straddling him, and he impulsively stretched his head up, his nose brushing against her vulva.

Both of them shuddered as his muzzle touched her secret flesh. It was unbelievably warm and wet and as she involuntarily winked Troubleshoes completely forgot about the fact that she was slurping his salami and instead locked his focus on the horsepussy right in front of his face.

He traced his tongue along her folds, pausing as the taste first registered—strange, metallic, grassy, unlike anything he’d ever tasted and yet he knew with certainty that this ambrosial nectar was better than the finest wine.

She quivered again as his tongue found her clit, first by accident and then on purpose. He was a stallion on a mission, even if he wasn’t entirely certain what that mission was.

Rain was on top, Rain got to set the pace. He knew that a mare could climax and he figured she’d step off when she was satisfied.

•••

Rain hadn’t been convinced that she’d made the right choice as she started blowing Troubleshoes; she’d anticipated getting him lubed up and then he’d get back to his hooves and mount her like every other stallion she’d met so far. But he hadn’t; she’d shifted her hindquarters to get a better angle on his cock and he’d stuck his nose under her tail and gone to town.

It wasn’t the first time she’d been eaten out and it wasn’t the best head she’d gotten, but damned if he wasn’t doggedly determined. She felt him twitch and spasm in her mouth and took him all in as he came and expected him to quit as she let his softening dick flop against his barrel, but he didn’t. If anything, he doubled down and darted over her most sensitive spots.

Drool and cum cooled and dried in her fur as his tongue worked, diving into her pussy and then gliding over her clit, teasing and deliberate. His hoof had discovered her teats and teased them, building pressure as the pleasure center of her brain scrambled. She was on top, she was supposed to be in charge, and yet she could do nothing as his tongue pressed up against her g-spot and then darted away to tease her before returning anew.

She felt his dick stirring under his chin, ready for another round, but she wasn’t. The world shrunk to pinpoints of pleasure and she had enough presence of mind to give him encouraging strokes before he pushed her to the edge and she just pressed her rump against his face, demanding release.

After, the two of them lay panting in the moonlight.

After

At first, the actual sex was anticlimactic. Almost obligatory.

Despite the fact that Rain had nearly sucked his soul out of his cock, despite the fact that she’d nearly drowned him in marecum, Troubleshoes had a new erection. His mind was scrambled and unable to process what had transpired, but his little head still had a goal in mind.

As the two of them lay there in the moonlight, gilded in moonshadow, glistening with sweat and sex, they held each other. His forehoof across her shoulder, his muzzle buried in her mane, and her tail lazily flicked across his hard-on, calling his little stallion to action.

Whether by accident or design, it slid across her rump, bumped into the soft, slick flesh, and she moaned.

Troubleshoes shifted his body, settling his dick against the edge of her inviting lips and her throbbing clit, just touching her udders and for an undetermined time the two of them were happy with this arrangement, then Rain grunted and shifted her rump, letting his head brush hard against her clit.

His first thrust was tentative, exploratory, and didn’t really go anywhere, then she moved again and let him press up tight against her marehood and push through, dampening his head.

For a few minutes, this was enough; the two of them remained cuddled together, and then she moved again, lining him up.

Troubleshoes thought that her mouth was the best thing ever.

He was wrong a lot.

Rain was warm and wet and inviting and he’d thought that her mouth was amazing and while he wasn’t wrong, at the time he’d thought that he didn’t have the full picture. He didn’t understand how different this would be, how it could be even better.

Before, the two of them had been competing and they’d both won. Now the two were working to a common goal, now there was pressure on neither. They’d both gotten the immediate out, they’d both learned about each other’s bodies and each other’s pleasure, now it was huffs and soft moans as he buried his dick in her, his balls banging against her clit at each thrust.

He tossuled her mane and nibbled her ears and bit her withers and as she got close she started trotting in place then froze as she was on the cusp of climax. Troubleshoes almost pulled back to ask her if she was okay and the two of them came almost simultaneously.

•••

Rain shuddered as she felt him cum, her muscles instinctively pulling him in against her cervix, and he was big enough to lightly touch it, giving her the strangest pleasure-pain that was as quickly forgotten as she orgasmed again, then another time after he’d gone soft—still inside her—and withdrawn with a wet splat.

He nuzzled and whuffed and let out a long, pleasured sigh and she let her focus broaden as his breathing slowed. She let herself take in the warm body pressed up against hers, the feel of grass and earth on her barrel, the harsh moonlight, softened only by the trees. She allowed a few aftershocks of pleasure from the memory of his touch and the final dribble of cum that was drying on her hindquarters.

Maybe in the morning they’d have sex again, or maybe they wouldn’t. Maybe she’d feel the need to go back to her herd; maybe he’d feel the need to go back to the mountains.

He started snoring, and she pressed up against him, safe and secure. The morning would bring what it brought; for now, there was nothing to concern herself with but the present.

Author's Note

An entry for the Furry Foray Festival.

No notes; if you've got questions, ask your parental unit.