Requests 2

Fancypants glanced once more at his pocket-watch. His date was by no means late yet, but he had to admit he’d expected Rarity to arrive earlier. Perhaps she was simply taking her time chatting with the other couple. He could easily imagine that. Rarity could certainly become talkative when the mood struck her. It was one of the qualities he found he admired in the oddly high-class Ponyvillian.

Fancy had initially been curious of the mare’s insistence on making this a double date at first, but that was before he had remembered her penchant for social activity. In fact, he had to admit he felt foolish for thinking a dullard like himself would have been able to entertain her alone.

No sooner had he finished this thought then the object of his affection entered his view. Accompanying the alabaster mare was a pair of stallions; one large and red, the other feminine with a caramel color. Fancy smiled quietly to himself. The generous mare must’ve offered to join a young couple of colts too nervous to come out on their own. He couldn’t blame them. It was no surprise that a small town like this might not take kindly to a pair like them.

He waved the group to his table shortly after Rarity had begun talking with the host. The host then made sure to escort them hastily to his table along with a few menus. Nopony paid the host any attention though of course. Rarity was far too busy introducing them all.

“Hello Fancy darling,” the mare said as she took a seat beside him and gave him a playful peck on the cheek, “I’d like you to meet our company for the evening. This little one over here is Caramel,” she pointed a hoof to the smaller, more mare-like of the pair.

“Pleased to meet you,” the tan pony said cheerfully as he took his own seat.

“And this stud over here,” Rarity continued with only the slightest pause to point her hoof at their other guest, “Is Big Macintosh.” Big Macintosh responded with a nervous smile and a nod. Fancy quickly struck upon him as the reason Rarity had insisted on doubling up. He was clearly quite shy. “I’m sure you’ll get along fabulously,” the mare finished.

Fancy nodded and extended a hoof towards the couple. Both of them shook it quite gingerly, although Big Macintosh did so with a decidedly firmer grip. “Pleasure to meet you both,” the unicorn said once he’d withdrawn his hoof.

What proceeded from there was what Fancy could only describe as a surprisingly boring evening. Caramel was certainly a talkative colt. So talkative in fact that he had managed to leave little room for anypony else to speak. Rarity was the only pony he ever made pause for. Perhaps it was out of courtesy to the only mare at the table; regardless, the only solace Fancy found in the meal was the food itself.

Eventually he managed to give up attempting to insert himself into Caramel and Rarity’s conversation and decided to begin talking with other abandoned stallion at the table. “So, Big Macintosh was it?” The red stallion nodded before turning downward to take a quick drink from a cider bottle. Right,” Fancy continued, “What is it you do for a living?”

Big Macintosh paused to savor his drink for a moment before responding. “Ah’m a farmer,” was all he said once he’d finished. Fancy noted that the poor fellow was still averting his eyes though.

“You must be Applejack’s brother then,” Fancy said, still desperate for some form of conversation.

“Eeyup.”

Fancy waited a few seconds for more, before it became apparent that no more was coming. Perhaps he’d best approach this from another direction. “You seem nervous,” was all he said, but hopefully it would be enough to get the stallion talking.

Big Macintosh nodded and finally turned his gaze to the unicorn. “Sorry,” he said, “This is my first date in a while.” He spoke quite calmly and clearly, but Fancy could see him blushing even through the red coat.

“Shame it’s not going very well,” Fancy said with an aside glance at the talkative colt sitting next to Big Macintosh.

“Sorry ‘bout that. Caramel sure can talk up a storm.” The stallion’s stoic face actually gave way to a nervous smile while he spoke. It looked good on him. “Still ah’m glad he’s here. It’s nice to have a friend along.”

Fancy paused for a moment before nodding. “Yes I suppose it is,” he said as he slowly turned his gaze to the mare beside him. The mare in question had taken a momentary pause to return the smile he was shooting her, and urge him to continue talking with what was evidently his date.

Fancy merely nodded in response to her and turned back to Big Macintosh. This was going to be a long dinner.

*****

Fancy managed to make good conversation with Big Macintosh throughout the night. Truth be told, he did find him somewhat charming, but he still had to find some way to let the poor colt down gently.

Eventually he settled on the truth as the best option. Big Macintosh struck him as somepony with a tough hide. Besides, making excuses would probably do little more than hurt him in the end.

In order to avoid a scene, Fancy decided to wait until the two of them were alone before explaining the rather awkward situation. The chance came easily enough of course. Rarity was nothing if not eager to see a successful coupling, and, at her insistence, Fancy found himself walking Big Macintosh back to his home on the far side of ponyville.

Big Macintosh took it surprisingly well. He simply kept walking in silence while Fancy explained the misunderstanding with Rarity. It was only once the unicorn had finished that he deigned to speak.

“Just one question,” he said, stopping momentarily to face Fancypants, “If ya’ had a marefriend back in Canterlot, why did Rarity think ya’ liked stallions?”

Fancy laughed in spite of himself. “Well you know how the tabloids are. One coltfriend and you’re gay for life. After I left Fleur she used that as the excuse, and the press ate it up. Apparently bisexuality is something that only exists in myths.”

“So ya’ do like stallions.” Big Macintosh shot Fancy a smile and resumed walking. Fancy was thrown briefly, but did his best to conceal it behind his usual grin as he continued trotting beside the red stallion.

“Does that mean you’re still pursuing this?” Fancy asked.

Big Macintosh responded with a nod, but didn’t turn to face his companion. “Ah’ don’t see you walkin’ away.”

“I promised my friend that I would see you home,” Fancy retorted jokingly. The stallion trotting beside him nodded, but didn’t speak. In fact no more words were uttered at all until they had reached Big Macintosh’s home. It had something of a downhome charm to it, the unicorn had to admit.

Big Macintosh nodded and opened the door. “Coffee?” he asked, without the slightest deviation from his usual tone.

*****

Fancy wasn’t quite sure what it was that finally got him into the stallion’s bedroom. Perhaps it was the assurances that it was a one-time thing, or maybe it was Big Macintosh’s promise that he wouldn’t mention it to the papers. Truth be told, it was probably just because he hadn’t had it in a while. Although that was hardly something he’d admit to.

Regardless of the reason, Fancypants now found himself sitting on the Big Macintosh’s bed. His suit had been neatly folded and laid on a bedside table while he awaited the stallion’s return. Big Macintosh had told the unicorn to settle in while he got ready. Admittedly Fancy was curious about what he was doing in preparation. He had originally suspected he might be gathering some simple basic supplies, but he was curious about why the stallion had to leave the room to do so.

The reasoning became clear once Big Macintosh reentered his room. The large red stallion had been taking his time getting dressed it seemed. The stallion in front of the door was wearing a quartet of long green socks and a set of green undergarments. In addition, the stallion was also wearing a distinct blush. “H-how do ah’ look?” he asked nervously.

Fancy’s thoughts were rather easy to read in this particular situation, but he responded nonetheless. “You look quite nice,” was all he could manage to say while retaining a degree of eloquence. This only caused the stallion’s blushing to grow even brighter.

“H-how b-bout from this angle?” Big Mac asked again. This time he turned to display the undergarments a bit more. A single red apple was adorned on them, and they were doing remarkably little to conceal the stallion’s features. In fact, Fancy could see quite a bit of Big Macintosh’s shaft sticking out of the front end.

Fancy failed to think of a response. The pressure in his groin was growing more intense by the second as he watched the stallion in front of him display himself. “Where do you keep the lube,” was all he could manage to say.

Big Mac blushed and turned to nod to a nightstand on the other side of the bed. Without taking his eyes off the pony in front of him Fancy moved back to the stand and pulled open the drawer. Inside was stored a single bottle of lubricant, a black stallion dildo, and a set of pink stockings. Fancy chose to ignore the toy, but he had to admit that the stockings did catch his eye. In the end, he chose to take them out along with the bottle.

Fancy made a show of donning the stockings of course, with a not so subtle lifting of his legs to display both his stallionhood and his asshole as he turned on the bed. Big Macintosh actually began to drool as he watched the unicorn magically pull his extra stockings over his hooves.

With the stallion distracted by this display, Fancy also decided to take this chance to float the bottle, unnoticed, over to Big Mac’s rear. The stallion gasped, primarily in surprise, as he felt the lubricant container maneuver it’s way around his panties and lightly probe his hole. The liquid inside filled Big Mac with warmth as it oozed into him.

Fancy pulled the bottle out with a pop as he finished dressing and stood over the stallion. He was going to ask if his partner was ready, but Big Mac responded with an affirmative nod before he could even ask the question. Fancy nodded back in response and eased his way into the stallion.

Fancy didn’t bother to remove the thong before he made his move. Just as he did with the bottle, he merely inched the underwear aside with his tip and began to stretch Big Mac’s ring. The crimson stallion remained completely silent as Fancy forced himself in. Fancy on the other hoof began to moan quite loudly the second after he felt the Big Mac constrict around his member.

Big Mac pushed back powerfully with each of Fancy’s thrusts, and the unicorn was surprised to find that he had already reached his deepest by the fourth movement. It was once Fancy finally reached his deepest that his partner paused and started grunting. In consideration for Big Macintosh, Fancy paused momentarily himself to lean down and wrap his hooves around the stallion.

“Do you want me to continue?” Fancy asked seductively. The prompted another grunt and an eager nod from the stallion below him. Fancy smiled to himself and pulled away from Big Macintosh. Within a moment he had his hooves on the stallion’s back and had resumed his thrusting at a steady pace. Big Mac responded very positively to these motions. Before long the big red stallion had fallen forward, not due to the pressure that Fancy was placing on his back, but out of a desire to lean further into the unicorn.

Fancy couldn’t contain himself for very long after Big Mac had reached his lowest point. The combined feeling of the stallion and the silk thong as they rubbed against his shaft was simply too much. Fancy let out a particularly loud moan as he fell forward and wrapped his hooves around Big Mac once more. Big Mac let out a loud grunt of his own as he pushed himself slightly harder against the unicorn.

The pair remained locked together, panting, for some time after that before Fancy pulled away. After this moment passed Fancy carefully removed himself from Big Mac and took a seat back on the stallion’s bed. Fancy had to admit a bit of satisfaction as he watched the cloth of Big Macintosh’s thong darken. “That really is a good look on you,” he commented.

Big Macintosh turned back and smiled. “You look pretty fine yourself,” he said with a blush. Fancy glanced down at his legs. He figured that Big Macintosh was probably referring to the lingerie he was now wearing. It didn’t take long for Big Mac’s head to suddenly break into his vision. “Mind if ah’ get a better look?” he asked.

Fancy nodded and laid back on the bed while lifting his legs. From there Big Mac moved quickly from there. Fancy cringed away momentarily as he felt the stallion’s tongue slide across his rear. Noticing this Big Macintosh lifted his head and shot Fancy a concerned look. The unicorn nodded him along. “It’s just been a while,” he said.

Big Mac responded with a nod and continued with his work; more slowly this time. Fancy still cringed but he didn’t pull away. The feeling was wonderful, and it became even more wonderful when Big Mac finally eased the organ inside of him. The stallion made sure to make this last too. It was just about when Fancy began to feel himself hardening again that he finally stopped the caress.

Fancy caught his breath and looked back to the stallion. Big Mac was getting to a stand now. After his head was lifted back to a more standard height, he moved to join Fancy on the bed. The unicorn actually gulped once Big Mac had positioned himself. The stallion looked quite intimidating from this angle.

Big Mac started to say something, but Fancy nodded before he could get the words out. This prompted another brief blush from the red stallion, but Fancy paid it no attention. His mind was focused on the rather large instrument now casually hovering around his rear. It certainly felt a lot bigger than it had looked in the panties.

Once given the go ahead Big Mac once more moved quickly and with purpose. Fancy let loose a loud yelp at the moment of penetration, and for a moment he felt the stallion shy backwards. He fixed this problem quickly however by inching back towards the stallion and spreading his legs just a touch wider. “Don’t stop just yet,” he said. Big Mac smiled quietly and moved into his second thrust.

Fancy did his best to stifle the noises that Big Mac’s thrusts urged him to make, but in the end he failed quite spectacularly. The moans grew louder with each deeper push that the stallion made, and it eventually culminated in a raucous fit of yelling while Big Mac pounded his rear.

Fancy wasn’t sure exactly how long it lasted. He measured time as best as he could by catching the occasional glance at Big Mac’s face whenever he could manage to open his eyes on the pullback before a particularly powerful thrust. At first the stallion seemed concerned, but that passed quickly. The stallion remained in a fit of pleasure for a good portion of time after that, and after that he moved into a holding back sort of cringe. Throughout the activity though, Big Mac kept up a steady and strong pace.

Fancy could feel his own second climax while he watched Big Mac struggle to hold back his first. All it would take was a little push from his magic and he would be able to reach it, but he had to admit that he was curious to see if the large stallion could push him the remaining distance. It took him by surprise when Big Mac not only did so, but went above and beyond this call.

Big Mac’s last few thrusts were his most powerful yet. The stallion backed out completely with each one, and each pound produced another yell from Fancy, though it only took the first one to push him over the edge. This climax wasn’t quite as powerful as the last had been, but it was every bit as satisfying; Big Mac’s continued thrusting made sure of that.

Big Macdidn’t last much longer either though. It was, by the unicorn’s count only five more thrusts before he finished; six if you counted the finale. And Big Mac made sure to make a display of that finale. His final thrust was less powerful and more skilled. With a careful movement made to press down just right, the stallion glided smoothly across Fancy’s own length just in time for his finish. Afterwards he was more than happy to help the unicorn clean the warm fluid off of his chest.

Fancy gently stroked Big Macintosh’s mane as he felt the tongue glide across his coat. “I must say,” he said after taking a minute to catch his breath, “That went better than I had expected.” Big Mac didn’t respond; he was too absorbed in his cleaning to. Still, Fancy doubted that he’d disagree.

*****

Fancypants left the following morning before Big Macintosh woke up. As much fun as it had been, he still had a reputation to keep up, and damage control would already be bad enough as it was thanks to his momentary lapse in judgment. He did make sure to leave his companion a souvenir before departing though. In the same drawer that he returned the lingerie, Fancy dropped his bowtie before departing to speak to Rarity.