Chapter One (Non Clop): The Setup
When it came to Equestria’s geography, it was doubtful that any pony or creature could deny how varied and unique the nation really was. From the frozen tundras surrounding the Crystal Empire, to the boggy swamp-like terrain nearby the Smoky Mountains, and to the near-uninhabitable deserts that littered the southern landscapes near its borders; it seemed that Equestria had a region suited for every type of pony and their lifestyle. Whether it was for comfort, or to challenge their fortitude, it was hard to find any spot in Equestria where there wasn’t some township.
One of those towns was Apploosa, a somehow thriving community that managed to build a successful apple orchard and cider brewery in the middle of the desert. Despite some earlier scuffles with the pre-existing Buffalo Tribe, the town was now a booming spot for high-paying jobs and more “off the grid” living. And due to its peace treaties with the buffalo, most of the ponies in town didn’t bat an eye whenever different species came around town.
Of course, there were still a few curious glances towards a particular dragon thatcame to Apploosa with his Element friends.
For some reason, Twilight and the other five Elements were summoned by the Friendship Map to the desert community to help solve a friendship problem. Even though Spike wasn’t summoned himself, he was brought along just in case the others got into any danger. The ex-drake didn’t want to think he was needed, but being reminded of the Elements’ first interaction with Starlight Glimmer kept him from speaking up on the matter. So instead of arguing, the newly winged assistant just let the girls be while he explored the quaint township by himself.
Fortunately, the dragon wasn’t completely alone as he walked down the main street with a confident smile. Despite wanting to use his recently molted wings as often as possible to build up their strength, he was fine with walking to be more even with the Earth pony beside him. A familiar Apploosan stallion with a golden coat and blonde mane trotted next to him, and was more than eager to try and swap tales with Spike. The dragon remembered that the last time he and the others visited Apploosa, he didn’t think too much about Applejack’s cousin Braeburn; although, an accidental kidnapping and a massive pie fight would probably keep a lot of guys from doing much social interaction. But this time, Spike felt much more comfortable with the pony after learning how much the two had in common.
Most notably, their very similar mindsets which were causing so many ponies to sneak glances over at them while they walked together.
“So,” chirped Braeburn as he smiled giddily down at the dragon, “do you usually come with AJ and the others when it comes to those ‘Friendship Missions’?”
“Honestly, no,” replied Spike with a meager shrug, “Buuuuuuuuttttt… the last time all six of them were summoned somewhere for a serious mission, they almost lost their cutie marks forever because of some cult. They kinda figured having me within easy contact might be a good precaution this time.”
Even though he could understand Spike’s point, Braeburn couldn’t help scoffing a little with his muzzle pointed elsewhere. “Heh~ Well, hopefully all you’ll have to do is enjoy the sights of Apploosa while you’re here.”
“Are you sure about that?” asked the former drake as he perked his brows and looked up towards him with a cheeky-looking grin. “Because judging by how happy you look, I have a feeling you’d like to do a little more than just give me a tour~”
Braeburn’s cheeks began to blush a little, and he giggled nervously while trying to avoid Spike’s sultry gaze. “W-Well, ummm… C-Can you really blame me? I mean… You know…”
After a quick sigh, Spike rolled his eyes and replied happily, “Yeah, I know exactly what you mean. Applejack already told me about your rep around here, and I’m willing to bet that Big Mac gave you some juicy stories about me~”
That made Braeburn giggle even more, and the turn of his head away from Spike made him realize just how many guys at the nearby saloon were eyeing them from the window. He didn’t want to veer off his chat with Spike when they were still getting acquainted, but he still gave a cheeky wave of his hoof towards them as they walked past the building. After a quick exhale, Braeburn replied with a more sheepish-sounding, “Well, I… I ain’t gonna lie, I definitely heard a lot about your, errr… exploits~”
Spike chuckled with a devilish grin while shrugging in acceptance to that wording. Ever since that fateful trip to the Dragon Lands during migration season years ago, the little drake was able to make a name for himself as a rather… unconventional assistant around Equestria. Much like Apploosa itself, Spike was able to overcome the odds when it came to being successful at his controversial craft. Despite how young he may have looked physically, his confidence (as well as his legal and mental maturity) helped turn the tides in his favor when it came to being recognized and respected in the same profession Braeburn was known for.
Of course, Spike proved to be a bit more blunt about his lifestyle than the Apploosan as he replied, “Well, I certainly hope so~ Given how many cocks I’ve serviced over the years, I was hoping you’d hear a story or two to get inspired~”
Braeburn had to cover his mouth and muffle his reaction while his face grew a beet-red. Fortunately, a quick look around showed that no ponies were nearby them to overhear Spike’s statement. Nevertheless, the stallion still looked back at his open-minded friend and whispered, “S-Spike! We’re in public, remember?!”
“Right, I’m sorry…” Spike lifted his claw and gave an apologetic wave towards Braeburn, and looked around as well to confirm no ponies overheard him. “Heh~ Yeah, sometimes I forget that not all towns are as used to someone like me as Ponyville.”
“Well, at least you’re not the only one like that here,” noted Braeburn with an understanding nod of his head. As his blush began to decrease, the stallion added with his shoulders shrugged, “I mean, when it came to me being an Escort, it was mostly because everything lined up in my favor. It was scary enough just coming out as gay at first, since I didn’t wanna end up homeless or a statistic or whatever. But to my surprise, being in a town with such a low number of mares made most of the stallions miiiiighty open to a guy like me walkin’ around. Instead of gettin’ picked on or harassed, I was being offered good amounts of cash to get some first-hoof experience from guys who needed some... company. And since bills had to be paid, I figured, ‘Why the heck not?’ And before ya know it, here we are~”
Spike nodded with a respectful smile up at Braeburn, clearly understanding the means a fellow “Escort” would get themselves into such a taboo trade. Of course, the stallion was quick to huff and scratch the back of his his head the instant he finished talking. “Oh, shoot! Here I go again talkin’ my muzzle off. I’m sorry if I’m sayin’ too much.”
“Hey, it’s perfectly fine,” stated the dragon with a sincere tone of voice. “Honestly, it’s kinda nice hearing from another slut’s--Umm, I mean Escort’s experience.” After that little slip-up, Spike looked around again while giggling to himself. “Sorry, I’m not that used to using that term to describe myself. Only Twilight calls me that, and that’s mostly for her own comfort.”
“Well, at least she respects you enough as an adult to keep from judgin’ ya,” retorted Braeburn back at him. “Seriously, you wouldn’t believe how awkward Apple Family reunions used to be for me! The only reason they respect me now is because they found out how much I regularly donate to the orphanage the next town over. It’s kiiiiinda hard to hate a sex-worker when they single-hoofedly saved a bunch of orphans’ Hearth’s Warming.”
“Yeah, Applejack told me about that!” chirped Spike with an impressed smile up at him. “And I gotta say, that’s really noble of you! If I charged for my services, I’d probably do the same thing.”
“Well, thank ya kindly,” the pony said with a grateful tip of his Stetson. However, his face grew a little more blushed after hearing that last detail from the promiscuous dragon. “Although I gotta ask somethin’. Is the whole... ‘sex for free’ thing just because you don’t want your Dragon Greed rilin’ up again?”
“Weeeeellllll… I also don’t want guys to feel like they have to give something to receive a little relief, you know? Sometimes a good gesture is all you need to brighten up someone’s day~” Spike shot his buddy a wink after that answer, but then added with a more hesitant shrug, “But, uuhhh… yeah, I’d rather not have my Dragon Greed rile up a second time. Especially now that I have wings. I mean, could you imagine if I grew into a monster the size of the building that could fly and was horny?”
“Heh~ Alright, I’ll give you that,” Braeburn said with a shake of his head and a hearty chuckle. “I will say though, there are probably a loooooot of guys who’d love to have fun with a bigger version of ya~”
Spike knew that Braeburn was likely right, but he still huffed with a scoff and said defensively, “Yeah, maybe if they wanted to bottom~”
That caused the two guys to stop in their tracks and start laughing, not seeming to mind if anypony was nearby to overhear the dragon’s little quip. Since they had walked through most of the main road that went down Apploosa during their conversation, not many townsponies were nearby the outskirts to make Braeburn look too worried about any unneeded intervention. However, neither of them seemed to notice a particular stallion who was perched just around the corner of the Post Office, who was leaned over to get a look at both of them. And given how massive the brute looked, it was almost a shock that neither of them saw the guy until he lumbered out into full view.
“Whoa!” Spike jolted the instant he saw the brown and white stallion emerge seemingly out of nowhere. The dragon’s wings sprung out by instinct, and he ended up hovering a good ten feet in the air with a distinct leathery flapping. Even though his face showed a notable expression of fear or surprise, the heavy blush on his cheeks indicated that Spike wasn’t completely against seeing somepony that huge. Of course, the draft horse-sized pony retreated back several steps upon seeing that response, and tried to disappear behind the corner again.
“Wait, wait, wait, wait!” Braeburn quickly stood on his hind-legs as he held both forelegs out, with each hoof pointed at one of the two guys. His focus first turned towards Spike as he said assuredly, “Hey, it’s alright! It’s alright, he’s a local ‘round here. He’s actually one of the rodeo clowns as of recently!” He then turned back around while Spike was still hovering mid-air, and shot a friendly wave to the bashful stallion. “Heya there, Troubleshoes! Wanna come and meet Spike here?~”
The draft horse quickly disappeared behind the corner once more, almost as if a nervous colt was taking the reins instead of the stallion himself. Spike managed to land back on the ground, but his cheeks were still visibly reddened while he bit his bottom lip. As he blinked a couple times towards Troubleshoes’ direction, Braeburn huffed with a disappointed glance before saying back to the dragon, “Uhhh… don’t worry none ‘bout that, Spike. He might be a big fella, but he’s also as skittish as your yellow friend, errr… Fluffershy?”
“Fluttershy,” the dragon corrected briefly, but his sights were still set towards that building as his head began to tilt to the side. While his emerald eyes narrowed with a look bordering between curiosity and wariness, he had to take a quick breath before asking, “So… how well do you, like… know him?”
Braeburn shrugged rather casually and replied, “Honestly, it ain’t until recently that ponies ‘round Apploosa are willin’ to give him a chance. He was kinda considered a criminal for the longest time, but we were able to see he was just clumsy and not some ‘mastermind vandal’.” He chuckled a little after that part, and readjusted his Stetson while shaking his head in disbelief.
After a sharp exhale, the yellow stallion added with a raised brow on Spike, “I will say, though... if you’re meanin’ whether or not I know him like that, I can’t say I’ve ever had the privilege. Around these parts, it’s not really smart to go ‘round solicitin’ stallions left and right, you know? There might be a lot of willin’ guys in town, but that don’t mean an unwillin’ one won’t punch ya in the mouth for askin’ upfront. I usually just let ‘em come to me, and Troubleshoes ain’t never done that as of yet.”
“R-Right…” Spike nodded pertly, but he still tried to lean his body over to get a better angle around that corner. Even though he could understand Braeburn’s perspective on not asking out guys around this region, it was clear that the dragon saw an opportunity he wasn’t too keen on letting slip away. Not to mention, being a flying dragon with claws and fire-breath was probably a big reason he felt braver about seeking that Troubleshoes fellow out. So after unbiting his lip, Spike huffed before deciding to speak up. “Ummmm… Mister Troubleshoes? Are you still there?”
Neither of them could hear any confirmation that a pony was still around that corner. However, the faintest hint of a shadow could be seen peering from the ground where Spike and Braeburn could see it. That could’ve easily been a different pony (or even just some random object), but the drake was determined enough to smile and add optimistically, “J-Just so you know, I’m sorry for jumping like that! I mean… you’re literally bigger than Celestia, so I hope you can understand it from my perspective. But, ummm… if you’re the same Troubleshoes that Apple Bloom and her friends helped out, then I’d really like to know you!”
Another awkward bout of silence followed after that genuine response. While the two waited to see what Troubleshoes might do (if he was still there), Braeburn blinked a couple times before looking back at the dragon. He wanted to ask how Spike knew of Troubleshoes’ story from his cousin’s perspective, but that first statement got him curious enough to ask, “Wait, is he really bigger than Princess Celestia?”
“I think so,” answered Spike with an honest shrug. He turned back to Braeburn and added hesitantly, “I mean, I’m not a hundred percent sure since he was kinda far away, but it seemed like it. Although, if I were to count Celestia’s horn, then I think she might be a little taller th--”
The sound of a couple heavy hoofsteps interrupted Spike’s words, and the two looked back to see Troubleshoes’ head peeking from behind the building once more. Instead of flinching a second time, Spike carried a much friendlier smile as he waved a claw towards him. “Hi there! You wanna come over and chat with us a little?~”
Despite the small suggestive perk the dragon instinctively made with his brows, he kept his expression fairly innocent-looking as a whole for Troubleshoes’ sake. While Braeburn carried a warm smile and kept himself rarely silent, Troubleshoes slowly walked out from the corner with a timid-looking stance. The stallion’s white muzzle was visibly wrinkled, making it clear that he was still more than a little apprehensive. If this was any other pony, Spike would’ve likely went right up to them and make his intentions crystal-clear; but due to his experience with more sensitive friends like Fluttershy, the dragon kept himself in place as he smiled kindly towards Troubleshoes. “If you want, we could easily talk with you at a different time if it makes you more comfortable.”
Troubleshoes seemed a little less nervous after hearing that option, and gave a meager-looking smile and a blush back at the dragon. However, the stallion then looked away from the two to point his muzzle down to the ground. He looked like he was taking a couple breaths, and trying to get himself ready to act appropriately. Meanwhile, Braeburn gave a light nudge to Spike’s side before whispering with an impressed smile, “Man, you really are good at bein’ social, ain’cha?~”
“Well, I’m not just a slut, you know,” Spike replied back with a cheeky smirk. “I am a Royal Assistant too.”
“Right, right…”
After nodding in understanding, Braeburn looked back at Troubleshoes alongside his scaled friend. Fortunately, it seemed that their quick back and forth was just long enough for the larger stallion to huff in determination. Troubleshoes pursed his lips tightly shut as he looked back at Spike, and breathed in through his nostrils before walking forward. The dragon didn’t say anything to spook him, but he smiled a little wider in anticipation of the burly stud coming towards them. Braeburn, upon seeing that Troubleshoes looked to be focused on Spike, politely stepped away so the two could have some more room.
As soon as Troubleshoes came up to the dragon with a heavy blush and tensed-up expression, Spike put out his claw to introduce himself properly. “Hey! My name is Spike. I’m here in Apploosa with my friends, and I was curiou--”
“Can you come to my place tonight?”
Troubleshoes’ sudden, deeply-toned statement was abrupt enough to freeze Spike’s greeting for a split-second. Braeburn had to do a double-take after hearing that reply, and blinked a couple times while his brows were raised. Meanwhile, the dragon himself was able to recompose himself after a second or two. “Ummm… a-absolutely!” he chirped with a surprised and grateful smile, certainly not wanting to look a gift-horse in the mouth. He didn’t want to make any hasty assumptions, but Spike was hopeful enough to ask with a blushed shiver, “Do… you want me to bring anything?”
Troubleshoes’ blush grew even heavier, and his eyes darted back and forth with a growing look of hesitance. However, despite Braeburn standing nearby within earshot, the burly stallion was able to look back at Spike and nod his head. “Ummm… B-Bring some lube.”
Braeburn’s jaw dropped, looking downright offended that Troubleshoes just asked the dragon upfront. As for Spike, his face lit up like it was on fire as he nodded excitedly. “You got it!~”
After exhaling shakily with a confirming nod of agreement, Troubleshoes ran off without saying another word. Braeburn just stood in utter shock while gawking at Spike, who looked like he was trying his hardest to keep from dancing giddily. Upon seeing the dragon’s bubbly, giggling reaction to that proposition, it took everything in the Apploosan to not scowl in bitter jealousy.
“Hehehehehe… Oh my gosh, that was one of my quickest offers ever!~” beamed Spike as his wings spring out and buzzed in anticipation. Of course, his excitement wasn’t enough to keep him from saying towards Braeburn, “Ummm… you wanna come along with me, Brae?~”
“No, no… He clearly wanted you…” Despite how strongly Spike’s expression slumped after his offer was rejected, Braeburn could only sigh and walk away with a dejected look of his own. Before his friend could say anything else, the stallion raised a hoof and said, “Y’all have fun tonight. I’ll be at the saloon if you need me…”
While the dragon remained by himself with a saddened look, Brae waited until he was out of earshot to mutter to himself, “Dammit! I’ve wanted Troubleshoes to fuck me for months…”
Fortunately for Spike, as well as Equestria as a whole, Twilight and the others were back at the Apploosa Hotel by nightfall without any problems. Even though none of them were able to find the specific friendship problems just yet, the fact that none of them got injured, imprisoned, or altered in any way was enough to make the dragon feel content with himself. After making sure that none of the six needed anything from him, Spike was quick to leave the town to make his way towards Troubleshoes’ place.
Since his now-debunked “criminal history” has been forgotten and forgiven by townsponies, Troubleshoes’ mobile home was considerably closer to the township than its previous spot several miles elsewhere. The modest wagon was still parked in a rather secluded region of the desert away from most Apploosans, but Spike saw that as a welcome addition to their more… private activities. Not to mention, the lack of foliage around the area meant that the moonlight was all he needed for illumination as he flew soundlessly across the night’s skies. Despite the fact that dragons weren’t really affected by the desert’s scorching heat in the daytime, Spike appreciated the cool summer breeze that wafted across his scales during his solo flight.
As soon as the wagon came up upon the horizon, Spike sighed with an excited smile as he made his careful landing. Due to his recently molted appendages, the dragon could no longer use his trusty backpack to carry all his supplies when it came to his craft. While he was grateful that Rarity made him a sturdy fanny-pack that didn’t affect his flying abilities, he couldn’t help but feel like a dork when he wore it around the front of his waist. But alas, given who he was visiting, the dragon was much more excited for what he had inside of that pack for Mister Troubleshoes.
Spike carried an antsy smile on his face as he came up to the front door of the stallion’s wagon, and gave a couple firm knocks with his claw. He could hear some banging and rustling from inside, most likely from Troubleshoes shuffling inside the cramped space to answer the door. Spike noticed that the door’s latches were visible from the outside, which prompted him to step back a little so he wouldn’t get whacked by it. Luckily for him, that attention to detail proved to be very necessary as soon as Troubleshoes opened the door. The old hunk of wood missed Spike by less than half a foot as it swung out powerfully, and whacked hard against the outside of the wagon.
Even though Spike wasn’t hit by the door, Troubleshoes sucked some air through his teeth while wincing from that awkward appearance. Despite seeing that the dragon was alright, the stallion breathed out worriedly and asked, “Ummm… Are you okay, Spike?”
“Yeah, I’m fine,” Spike answered with a reassuring smile and a shrug. “Trust me, even if that door did hit me, it wouldn’t have been the worst thing I’ve dealt with.”
Troubleshoes could see that Spike meant that statement genuinely, but he didn’t want to ask for any examples to ease his mind. Instead, the draft horse nodded his head briefly before trying to step back from the doorway. Even though his backside ended up pressing against the opposite wall of his wagon, Troubleshoes was able to give Spike some room as he invited him inside. “Would you like to come in, please?”
“Certainly~” the dragon chirped with a wide smile as he nodded back to Troubleshoes, and maneuvered his way around the stallion’s bulking build to enter the wagon. The interior of the space was fairly messy, with a lot of discarded wrappers and papers littered around the limited floorspace. There were also a large number of items hanging from the ceiling at various spots, most likely as a means of adding impromptu storage to such a cramped living space. Even with his tiny frame, Spike couldn’t help feeling a little confined while Troubleshoes went to close the door.
Note to self, thought the dragon as he went to unzip his fanny-pack preemptively. After this, I should give Troubleshoes some space-saving tips from what I’ve seen in Trixie’s wagon.
Troubleshoes tried to turn himself around to face Spike, and ended up grunting uncomfortably as he struggled to maneuver himself within the tiny space. His lumbering weight made the floorboards beneath him creak dangerously loud, and he groaned when he accidentally whacked his head on an assortment of pots hanging over the woodstove. Spike cringed a little upon seeing that, but didn’t say anything out of politeness. Instead, the dragon stayed patient as he waited for Troubleshoes to face him.
“So, ummm…” Despite looking like a blunt and direct stallion, Troubleshoes had to briefly pause as he scratched the back of his thick neck and looked away from Spike bashfully. “Did you, uhhh… get what I asked for?”
“I sure did!~” Spike pulled out the vintage-looking mason jar he was carrying in his pack, and placed it on the nearby table on top of a stack of papers. Troubleshoes blinked a couple times as he leaned in to inspect the unmarked item. It didn’t look like it was any brand of lube that could be bought at a store, and it was three-quarters of the way full with what looked to be a yellowish translucent substance. “Just so you know,” said Spike as he put up a claw and clarified, “That really is lube, okay? I buy it from a zebra apothecary near my place named Zecora. And I can assure you that I’ve never used anything as good as THAT stuff~”
Troubleshoes nodded his head in understanding, and exhaled shakily with a look of apprehension on his face. Nevertheless, he was able to look back at Spike with a notable blush as he asked, “So, uhhh… is there anything I need to do first?”
“Well, that’s all up to you~” Spike shrugged casually after replying with that, and tried to keep his smile friendly as he explained the details to him. “I offer my services to make guys like you feel better, without the worry of any obligations or payment. As long as you feel good, I’ll feel good too. If you wanna talk some more and feel more comfortable, that’s totally fine with me. Or, if you wanna just get to the fun stuff, just tell me where to go so we can get started~”
Spike beamed excitedly after that last sentence, and tried to keep himself still to avoid looking too antsy for someone as sensitive as Troubleshoes. Fortunately for the dragon, it didn’t seem like his fidgety stance was enough to spook the stallion as he looked between Spike and that jar of lubricant. After thinking over Spike’s words with enough time to properly process them, Troubleshoes huffed with a more determined nod back towards him. He lifted one of his hooves to point behind Spike and say, “Well, umm… let me get to my bed back there and we can get started, I guess.”
“Awesome!” exclaimed the dragon as he nodded eagerly, and quickly went to maneuver around the bulking stud. Even though he didn’t feel comfortable unfurling his wings to fly over Troubleshoes, Spike was light and agile enough to stay on the ground, and step over some of the cluttered furniture and allow him to pass. Unfortunately, the dragon’s size and agility proved to do very little to keep Troubleshoes from bumbling across the wagon towards his bed. Like a literal bull in a china shop, the draft horse was clanging and brushing up against every surface nearby before falling onto his mattress, which was stuffed into a cubby that was almost half his size.
While Troubleshoes shuffled into the space with his hind-legs still braced against the floor, Spike’s wings flapped uncontrollably in anticipation. He shivered in delight upon seeing the stallion’s unbelievably thick, toned rear fidgeting in front of him, along with a hefty pair of baseball-sized, low-hanging balls that could be seen peeking from between his legs. Spike’s mouth started to water, clearly envisioning just how those nuts would taste while slathering every inch with his reptilian tongue. Of course, despite his own ideas trying to take focus in his dirty mind, the dragon was able to take a breath and ask while grabbing the jar of lube, “Alright then! So, are you ready for me, big guy?~”
Troubleshoes glanced back at Spike while half-laid into the cubby, and blushed hard when he saw Spike begin to uncap the jar. Despite how much he bit his lip, the draft horse nodded with a light huff. “Y-Yeah, I… I think I am...”
The stallion then braced himself into position, and lifted up his rear to face the dragon. Spike paused briefly while blinking a couple times, looking downright surprised as he realized what position Troubleshoes was getting into. Part of him wanted to assume it was for something else, but the pony’s intentions were quickly confirmed the instant he lifted up his thick, stumpy tail. His massive, meaty tailhole puckered a little upon being exposed, and laid out in the open while Spike stood dumbfounded.
Troubleshoes didn’t seem to notice Spike’s surprised expression, and faced his head back forward while waiting for the dragon to mount him. “A-Alright, ummm… I’m ready for the lube…”
Spike stood in silence for several seconds, and blinked a few more times as he processed what the draft horse was wanting from him. Even though he was still turned-on greatly, it was obvious he didn’t expect someone as big as Troubleshoes to want him to top. After taking a moment to re-evaluate his state of mind, the dragon shook his head clear before shrugging to himself. “Ummm… o-okay then, Mister Troubleshoes,” he said in a slightly less confident nod.
Maybe it was the notable change in the dragon’s tone of voice, or more the long pause that came before it, but something prompted Troubleshoes to look back at Spike with a worried glance. “Is somethin’ wrong?”
“N-No! No, not at all!” Spike blurted with his claws raised in insistence, not wanting the stallion to worry. Even though he was rightfully surprised, the dragon couldn’t say he was necessarily against being the top. However, due to his own preferences (as well as the significant size-difference between himself and Troubleshoes), Spike couldn’t help huffing with a bemused smirk as he added in an honest tone, “I just, uhhh… I was kinda hoping you’d want me to bottom, that’s all.”
Upon hearing that, Troubleshoes sighed with a deeply disappointed look as he looked away from him. His rear lowered a little, and his tail slowly started to pull down to cover that tailhole. Spike was quick to see that response, and added without hesitation, “But it’s not a problem at all, I swear! Believe me, I have no problem with topping if you want that.”
Despite that remark, Troubleshoes still lowered his tail completely. From the way the stallion’s sigh came out in such a disheartened tone, Spike was worried he was going to just make him leave his wagon. Part of him wanted to stay insistent with his assurance, just so the stallion wouldn’t think he was reluctant about giving as opposed to receiving. However, the dragon could also tell that Troubleshoes was likely too sensitive to accept any further statements as being genuine. So instead of doubling down, Spike sighed briefly to himself while rubbing his arm with a claw, and took a moment before deciding a different route.
“Ummm… If you don’t mind me asking, Troubleshoes, have you… have you ever been a bottom before?”
The dragon made sure to ask that question with a notably curious and informative tone, not wanting the stallion to think he was being mocked. Several seconds passed before Troubleshoes exhaled with a lingering huff, and answered solemnly. “No. I… I never got the courage to ask anyone before you…”
That response made Spike wince with a bit lip, feeling legitimately bad that he likely hurt the pony’s feelings with that earlier assumption. Before anything else could be said, the dragon quickly replied, “Hey, I… I’m really sorry if I upset you, alright? I promise I’m not judging you. I’ve topped a lot of guys before.”
“I’m sure you have, but…” Troubleshoes paused after that brief response, and took another couple seconds to sigh with his eyes closed. After that, he meagerly looked back at Spike and said with an uneasy shrug, “Well, I… It’s not really easy for me to just ask guys around here, ya know? I mean… I’d ask Braeburn, but I don’t want ponies knowing I like that from him.”
“Well, why not?” asked Spike with a genuinely curious tone, not sounding apprehensive towards Troubleshoes at all. “Like, wouldn’t it be easier for you to find somepony to top you if it was known?”
Troubleshoes breathed out sharply and said in a more hoarse tone, “Cause it’s already awkward enough living’ in a town where everypony used to hate me. It’s hard for me to make friends with my past, and… And I don’t want the fact that I’m a bottom comin’ out and givin’ everypony an excuse to make fun of me outside the rodeo.”
Spike didn’t want Troubleshoes to feel like he had to hide his preferences, but he kept that opinion to himself as he shrugged his shoulders in understanding. Instead of giving any reassurances, the dragon responded with, “Well… Okay, I won’t try to say anything against that. If you don’t want any locals to know you like bottoming, I won’t tell a soul. I promise.”
Troubleshoes could tell that the dragon truly meant that, which helped him to grow a faint smile for Spike to see. Happy to see that kind of response, Spike then walked up to the still-presented stallion and hugged one of his thick legs. “And I really am sorry if I made you think I wasn’t up for that, alright? I can assure you that I am.”
Despite that point being made crystal clear, Spike couldn’t help pulling away and adding with a slightly hesitant shrug, “I just kinda… expected you wanting someone bigger than me to fulfill that task. Heh heh...”
Spike hoped that his additional chuckle was enough to make Troubleshoes know that point wasn’t too significant on the matter. Fortunately, the stallion huffed with a small nod of his head, and said in a more casual tone, “Well, yeah I guess. I just wanted someone with experience who wasn’t a local, and you fit the bill for that. Plus, I… I didn’t want anyone too big for my first time…”
Troubleshoes blushed bashfully as he looked away from the dragon after that last part. Spike wanted to giggle to seeing such a thing, but was lucky to keep his mouth shut and nod with a smile. “Hey, that’s perfectly fine. I just wanted to make things clear in case the size difference between us is a little… too much. You get what I mean?”
“Yeah, I do,” replied Troubleshoes with another nod. He then looked back at the dragon with a more comfortable smile, and added genuinely. “As long as I can feel it, I’ll be happy.”
“Will do~” assured Spike with a mock-salute motion of his claw, and a quick ‘whoosh’ as his wings erected from his back. Troubleshoes’ wagon may have been cramped, but the little dragon had enough room to hover in the air with his wings flapping easily. As he got himself to a more even level to the burly draft horse, Spike held the open jar of lube with his claws and asked him, “So, Mister Troubleshoes… Are you ready to say you got yourself some dragon cock?~”
Troubleshoes chuckled nervously, and blushed as he looked up towards Spike’s flying stance. His muzzle pursed shut upon looking down to the dragon’s crotch, which was completely uncovered to reveal that petite cock sticking out proudly. It wasn’t big by any means, but the sight of it was still enough to make Troubleshoes gulp before nodding his head. “Y-Yeah, ummm… I mean, I won’t be sayin’ it in town, but… I do want to experience it.”
“Yeah, that was what I meant,” Spike clarified with a roll of his eyes and a carefree smirk. “Sorry for the wording there. But anyway, let’s get to it!~”
Troubleshoes smiled with a nod back at him, and was quick to get back into his ready stance. The stallion bent back downward with his thick rump hanging in the air, and his stumpy tail flagged up and ready. Troubleshoes still appeared nervous, but his shaky stance could be seen by Spike as more anticipation than any sort of hesitance. Because of that, the dragon carried a sly and curious grin as he hovered behind that massive butt, and pulled his lube-coated claw from out of the jar.
“Alright, big guy~” Spike put down the jar and hovered in closer towards Troubleshoes, which elicited a small shiver from the stallion when he heard those leathery wings fluttering so close to his backside. He then gasped lightly the instant he felt the dragon’s dry claw rest against one of his firm cheeks, holding himself still for leverage. Spike waited a second before doing anything, and shivered as he caught that strong scent of musk from just beneath the dock of the stallion’s tail. Even though he was planning to just slather the lube over that tailhole and go in, the dragon couldn’t deny how tempting that tailhole looked when he was so close to it. The circumference of that wrinkly, puckering entrance looked to be as big as one of Spike’s claws itself, and it was obvious that Troubleshoes had prepped himself prior to ensure it was clean for him. However, even with that lingering scent of soap being notable in the pony’s brown fur, it was that overlaying scent of sweaty musk that was making Spike’s mouth water.
“Mmmmm… You know what?~” said the promiscuous dragon as he leaned in closer, and got a quick whiff of Troubleshoes’ scent before any response could be said. The stallion could hear Spike shudder audibly the instant he got a good hit of that rich, heady aroma, but was unable to know what to say. Fortunately, Spike spoke up before Troubleshoes could even open his muzzle. “How about I give you something a little extra before the main event, hmm?~”
“Hmm?” Troubleshoes may have not been a dumb stallion, but he wasn’t completely aware what the slut was planning as he tried to look back at him. He wasn’t able to see Spike’s blushed, hungry-looking grin as he asked, “What do you mean byyyYYYOOOOHHHH!!!~”
Troubleshoes had no time to properly ask his question, and was quickly thrown into a spine-tingling frenzy the instant he felt Spike dive face-first against his massive ass. The slutty dragon pressed his face in directly against the draft horse’s musky hole, and took a deep breath before moaning shakily. Given how large and eye-drawing Troubleshoes’ backside really was, Spike couldn’t control himself as he opened his mouth wide, and dragged his thin tongue up that wrinkly pucker without warning. Troubleshoes yelped out even stronger in response to that reptilian muscle gracing his sensitive flesh, but his body refused to pull away from it as his hind-legs convulsed beneath his weight.
“Nnnnnghhhh…~” Spike closed his eyes as he groaned in deep pleasure, and took his time while tending to Troubleshoes’ hole with his diligent licks. With every strong, enthusiastic lap of his tongue against that plump ring of flesh, Spike’s wings flapped even harder as he tried to stay afloat in arousal. Fortunately, both of his claws were gripping Troubleshoes’ cheeks as he kept himself in place, not pulling away from that twitching rump for a second while getting more thorough. By the time the draft horse began squirming especially hard while belting out strained moans, the dragon’s slutty mouth was already trying to wrap around his pucker so he could put his tongue to proper use. All the while, Spike’s lustful groans could be felt by Troubleshoes as he endured each reverberation that echoed throughout his unprepared body.
“AAAHHH!!~” Troubleshoes may have only asked for a good fucking, but it was clear he wasn’t against the dragon’s tongue sliding inside of him as opposed to that cute little cock. The sudden, hungry flicks of that tenacious muscle inside of him caused his back to arch inward strongly, and his moans grew deeper with each second Spike spent eating him out. The dragon grew more primal as the strong taste of that musk flooded his senses, and his groans turned hungrier as he alternated between rimming Troubleshoes and breathing that scent in. Due to his nose being right against the top of that tailhole and underneath the dock, it was clear that the slut was in a content spot as he spent a good two minutes riling his stallion right up.
“NNNNGHHH!! Aaaahhhhh… O-Oh, FUCK!!~” The draft horse’s legs were starting to shake as he stayed in place for that unexpected devouring, but his deepening blush and growing cock made it clear he was more than alright with Spike’s idea of foreplay. With each heavy breath he took between his moans, Troubleshoes’ stallionhood twitched and throbbed beneath his barrel as it slowly grew to life. Much like the rest of his body, the stallion’s cock was absolutely monstrous the moment it slipped out of his sheathe, and extended to well over a foot in length. And given how floored Spike was by those plump balls, he probably would’ve fainted if he knew just how generously-endowed the pony was all-over.
Nevertheless, by the time Spike finally pulled his mouth away with an elated groan (as well as his face coated in his saliva and the stallion’s sweat), it was obvious that he was already pent-up enough to focus on Troubleshoes’ hole for the time being. While the stallion continued to moan and shudder beneath the ever-hovering dragon, Spike moved his mouth upward to try and wrap his lips around that meaty tail-dock. His light, tentative suckles could be heard as he gave some much-needed attention to such an under-appreciated part of the pony anatomy. However, those sweet-sounding slurps weren’t as notable as the lumbering moans that were still coming out of Troubleshoes’ mouth. Especially when he felt Spike’s lubed claw press up against his hole and start to apply that viscous fluid all over his sensitive flesh.
“Mmmmmm~” As he diligently got the draft-horse prepped and ready for the finale, Spike continued to slide his tongue around the dock of Troubleshoes’ tail to keep him enticed. The dragon’s cute, petite cock was twitching readily between his legs, and already dribbling a little precum that was hanging across the underside of his shaft. While he may have been worried about his performance earlier, he would’ve been crazy if he didn’t try to give this moaning hunk a good rutting now. And given how dangerously huge the draft horse’s cock would’ve been compared to Spike’s size, it was probably for the best that the dragon wanted to give instead of take.
As soon as his face pulled away from Troubleshoes’ rump, Spike hovered atop the presented stallion while his claws held onto that stumped tail. The draft horse shivered as he gripped the edges of his mattress tightly, not needing to look back to know the dragon was in waiting position to plow him. While that plump, glistening tailhole puckered relentlessly, and Spike’s twitching cock hovered just a few inches from it, the dragon closed his eyes as he shuddered antsily. “Mnnnnnghhhh… I really hope you’re ready, Troubleshoes~ Because I wanna see just how much a big guy like you can moan~”
Troubleshoes bit his lips tightly shut as he exhaled through his nostrils, and struggled not to groan impatiently. He may have had no idea how well Spike would perform, but he was more than eager to find out as he replied with a needy shiver, “Aaaaahhhh… S-Spike, you… You better…”
Troubleshoes needed to take another breath, but closed his eyes in contentment as he said in a more determined tone of voice, “You… you better not try to hold back~”
Spike grinned wickedly wide to such a request, and nodded firmly before saying, “For you, I wouldn’t dare consider such a thing~”
That was when Spike decided to go for it, and slammed his hips against Troubleshoes’ backside to make him squeal in his confined wagon. Even though the dragon knew better than to just shove his cock into a tailhole so suddenly (especially a virgin hole), the fact that Troubleshoes’ entrance was so huge prompted him to make an exception. Not to mention, the earlier lubrication and teasing with his tongue managed to open that meaty pucker surprisingly well, and allowed enough room for Spike to ram his efficient length inside without much resistance. Troubleshoes still proved to be remarkably tight, but his reaction to the dragon’s thrust was overwhelmingly positive after that first strained cry he let out.
“GAAAAAHHHH!!!~” The draft horse didn’t expect Spike to just plow into him full-length at the first thrust, but the first bout of stinging pain lasted quite minimally to his surprise. Since the dragon’s cock was significantly smaller than most stallions, it was able to slip inside of that tight ring of flesh with just one hard push. By the time Spike’s hips collided with Troubleshoes’ firm cheeks, the stallion was squirming with gritted teeth while processing that first moment of penetration. “Nnnnnghhhh… Ho… Holy fuck~”
“A-Are you alright?” asked Spike with a brief look of worry while buried inside of the stallion, and still holding tightly onto his tail. Even though he felt like that first push was relatively easy, the last thing he wanted to do was hurt the big guy. Luckily for the dragon, Troubleshoes was able to glance back at him with a tremendously heavy blush on his face, which almost concealed the faint smile on his white muzzle. Instead of berating Spike for such a hasty introduction, the draft horse gave a small nod of his head.
“Y-Yeah, uhhh… I think so,” he said with a genuine, albeit flustered-sounding tone. After a brief exhale, Troubleshoes pulled his head back forward and closed his eyes tightly in anticipation. “Okay, I’m good. Keep at it!”
Spike beamed when he heard the stallion’s chipper response, and nodded enthusiastically while still imbedded inside of him. “Yes, Sir!~”
Happy that Troubleshoes was still raring to go, Spike didn’t hesitate as he pulled his cock back out from the draft horse’s tight hole. With his claws still gripping Troubleshoes’ tail, the dragon had a readied stance with his fluttering wings to plow into the stallion just as hard as the first time. Spike may have not been the most hung guy in Equestria, but his energetic pounding was more than enough to make Troubleshoes moan out full-heartedly again. The feeling of being penetrated by such an energetically lustful creature, combined with the realization that he actually was being fucked for the first time, set the stallion’s heart ablaze with elation. His hooves gripped the bedding for dear life, and his cock throbbed immensely with each rhythmic thrust that was being delivered at a steady pace.
“Nnnnghhh!!~” Spike gritted his teeth as he got himself into the motions, feeling surprisingly content with his abilities when he heard how much Troubleshoes was enjoying each thrust. The dragon couldn’t stop grunting in exuberance and arousal, but he was barely heard over the sounds of his scaled flesh slapping repeatedly against Troubleshoes’ tight rear. Of course, the stallion’s hungry and lumbering moans overpowered both of those other noises due to his already deep voice. Nevertheless, Spike couldn’t help trying to speak up while (somehow) successfully plowing Troubleshoes. “Aaaaahhhh!!~ You… You like that, big guy?~ You like… g-getting topped by a real dragon?~”
“NNNNGHHH!!! Ohhhhh FUCK YEAH!!~” bellowed out the draft horse at a volume heavy enough to make the walls of his cabin shake a little. Fortunately, Spike didn’t seem to mind as he kept thrusting into that gorgeous ass, and panted heavily from the sheer physical strain. The dragon may have been fit, but it was obvious he wasn’t used to being on top as he started to sweat from his efforts. But regardless of his back starting to ache, Spike kept going at it as he felt himself getting close to release, and growing closer with each moan he heard Troubleshoes make. “Aaaaahhhhh!! G… G-Give it to me HARD!! MMMMPHHH!!~”
Spike wasn’t sure if he could thrust into him any harder than he already was. However, he did make sure to pull one of his claws away from Troubleshoes’ tail, and strike it down against that firm cheek to elicit a strained yelp from the stallion. “Aaaahhh!! Y-You like that?!~” He moaned out after that first smack to his ass, before going in and giving it another swat. Troubleshoes moaned out even louder, and didn’t seem to realize he was tearing up his sheets by gripping them so hard. Meanwhile, Spike kept pounding that tailhole mercilessly, and gave a couple more hard spanks to drive himself closer to climax. “You like that dragon cock?!~”
“OHHHHH!!~ MNNNGHHHH… FUCK YEAH I DO!!~” Troubleshoes’ head was reeled back with his muzzle hung open in bliss as he moaned out so heartily to the dragon’s efforts. With the way his rump and hole were burning hotly in depraved pleasure, it shouldn’t have been a surprise that the stallion was growing close to orgasm as well. His massive cock was throbbing continuously while slapping against his barrel, and spurting out hefty strings of precum that were landing across his chest and the mattress underneath him. He wasn’t sure how close Spike was, but he groaned out in dire need between his heavy breaths as he tried to speak pleadingly. “AAAHHH!!~ SP… SPIKE, I… I NEED YOU TO CUM IN ME, PLEASE!!~”
“I… I’M ON IT!!~” Spike stopped smacking Troubleshoes’ now sore right cheek, and went back to grabbing that tail with both claws to really fuck that ass relentlessly. His hips slapped against Troubleshoes’ body with the level of speed and ferocity only a winged creature could deliver, as he bore several thrusts per second to that tailhole to leave him moaning continuously. Meanwhile, Spike’s muscles were aching enough to make him yell out in a strained cry during his motions. But despite the exhaustion he felt pulsating through his body, his cock was throbbing immensely hard as it kept driving in and out of that pucker like a jackhammer. Just as he felt his wings straining while struggling to keep him afloat, Spike clenched his eyes shut and screamed during his final barrage of thrusts into Troubleshoes. “AAAAAAAHHHHHH!!! I…I’M COMIIIIIIINNNNGGGGGG!!!~”
“GGGGNNNNAAAAAHHHHHH!!!”
Despite how huge Troubleshoes was in comparison to the dragon, neither of them sure who yelled out the loudest by the time Spike reached his climax inside of the draft horse. In fact, Spike almost felt like a legitimate, fully-sized dragon when he finally reached his peak, and drove himself as deeply as he could inside of the screaming stallion. His little cock erupted powerfully, and shot a hefty load of dragon cum strongly enough for Troubleshoes to feel spurting into his deepest depths. But even as that climax washed over Spike like a tidal wave, and made his scales tingle near-endlessly from that nirvanic release, his heart skipped a beat when he heard how deeply the draft horse belted out his own cry of orgasm in response.
The instant he felt those strong spurts of Spike’s cum shooting into him, Troubleshoes’ entire body convulsed wildly as he succumbed to his own finale without any complaint. His monstrous cock twitched hard without needing to be touched, and unloaded an unholy volley that nearly exploded out of him like a broken faucet. His stallionhood continuously thobbed and spasmed as almost a liter of cum spurted out without stopping, completely coating his mattress and the underside of his torso with his thick and sticky load. Meanwhile for the rest of Troubleshoes’ body, his shaky legs finally gave out as he buckled over from the Earth-shattering orgasm that left him near-paralyzed, and he had no choice but to slump forward into his cum-puddle with a deeply satisfied shiver.
“AaaaaaAAAAAAaaaaaaahhhhhhhhh…~” With a look of pure contentment and peace glowing across his blushed face, Troubleshoes couldn’t have looked happier as he laid in his ruined bed and panted heavily. Spike, who was still inside of the stallion while clinging to his back like a housecat, was wheezing like he just finished a marathon wearing cinderblock shoes. But alas, even though his muscles were throbbing and numb at the same time, the dragon still had a pleased smirk on his sweating face for a job well-done.
Neither of them said anything for a good ten minutes, with both of them needing to collect themselves from such a strenuous and invigorating experience. By the time Spike’s cock was flaccid enough to easily slip out of the stallion’s hole, he had just enough strength in him to rest square atop Troubleshoes’ back. As for the draft horse himself, Troubleshoes could only sigh blissfully with a newfound peace of mind while his limbs still twitched from that orgasm. “Mmmmmm… Spike, you… you’re really somethin’ else~”
Spike chuckled as he heard that brief reply, and took a second before saying back to him in a cheeky tone, “Well, you’re not the first guy to tell me that~”
“Heh~ I guess that shouldn’t be a surprise…” Another moment passed between them as they laid together in mutual satisfaction and respect for one another. Given the situation, it seemed that both of them were pleasantly surprised that such a session ended so well. For Spike, he was able to experience a newfound confidence in his ability to top even the largest of stallions. And as for Troubleshoes, he could safely say he felt better about himself after experiencing something he desired for so long. After a while, the stallion took a breath and asked timidly, “So… are you plannin’ to stay in Apploosa for long?~”
“Welllllll… technically, I think I’m only supposed to be here until my friends solve that Friendship Problem thing,” answered the dragon in an honest, albeit slightly disappointed tone. However, he was still able to grow a sly grin and ask in response, “Why were you asking, big guy? Were you wanting another round before I leave?~”
“I think I’m good for tonight, honestly,” the stallion said with a tired shrug. “Buuuuuttttt… If you’re still available tomorrow, I… wouldn’t mind seein’ ya again~”
Spike smiled contently upon hearing that, and nodded his head while still perched on his back. “You know what? I would love to do this a second time with you, Mister Troubleshoes~”
Troubleshoes may have been thoroughly spent, but he still craned his head around to give the dragon a warm and genuine smile. Spike did the same back at him, and waited a couple seconds before tilting his head curiously. “Ummm… can I ask you for something regarding that, though?”
“Sure thing,” he answered with a polite nod of his head. “After all that, I think I’m a little open to whatever you were thinkin’~”
“Great!” chirped the dragon with a pleased smile, before breathing out to get himself back to a more serious tone. “S-So, ummm… if you don’t mind, would you… possibly be open to me inviting Braeburn next time?~”
Troubleshoes’ widened rather quickly, clearly worried about such a request. Spike immediately put a claw up to stop whatever the stallion might have to say, and added insistently, “I’m only asking because I know he wants to have sex with you. A-And… And ummmm…”
The dragon’s face started to blush quite a bit, and his expression turned bashful before saying with a meek-looking smile on his face. “If I brought him along, I… I promise he won’t tell anypony about you. And… and I’m absolutely certain we can both make you feel amazing, Troubleshoes~”
A long, pregnant bout of silence passed between them after that statement was made. Spike was hopeful that he made a good case, but he knew how sensitive Troubleshoes was about locals knowing what he enjoyed in bed. However, the draft horse stayed silent for a while as he processed that request, clearly thinking it over as his blush grew heavier. While Spike kept his lip bit in anticipation, Troubleshoes waited until taking a deep breath to say with an apprehensive sigh.
“Well, umm… Alright, he can join in next time.”
With the way Spike’s face lit up in an instant, Troubleshoes wasn’t sure whether to be really happy, or really worried about what might come next. But regardless of the outcome, the draft horse was hopeful that he made the right decision as he smiled back nervously.
