Friendship is Magic...With Benefits

“Mind if Ah’ ask why ya called me fer this?!” Applejack groaned and took a seat in the middle of the boutique while Elusive walked off to grab his measuring tape. “Not that Ah’d usually mind doin’ ya a favor, but Ah’ve really got a lot of work ta’ do back on the farm. “

“This should only take a few minutes, Applejack. I’m sure you’ll have plenty of time to get everything you need done.” Elusive trotted back to the middle of the boutique with his tape in hoof and his glasses on. “Now, stand up dear. I’m going to get your barrel first.”

Applejack stood up and shook his head as Elusive wrapped the tape around him. “’S just with Berry on me all week Ah’ve hardly gotten any work done as is,” Applejack said as Elusive pulled away and started writing down the measurements. Applejack turned to his friend and they shared a smile.

“That pony is insatiable,” Elusive chuckled and went back to work, now taking measurements of Applejack’s forelegs. Once he had those written down as well he spoke up again. “I do hope he hasn’t tired you out. I believe Dusk still has you scheduled for later this week.”

Applejack beamed with pride as he stared at Elusive. Though the unicorn pretended to be absorbed in his work, it was abundantly obvious that he saw the smile. “Ah’ll have you know that Ah’ can take every inch he can give.” A snicker from Elusive gave Applejack pause for a moment, and after that moment he shot the unicorn a glare before continuing. “Ya’ know what Ah’ mean! Ah’ve got more ‘an enough stamina fer the both of ‘em.”

“I’ll take your word for it, Applejack.” Elusive snickered again and grabbed Applejack’s chin, facing him forward and floating the hat off his head. “Now keep still. I need the head next.”

Elusive was easily able to guide the cowpony to the right position. They had been through this routine several times before after all, and Applejack knew how to behave properly for the most part. He did have one habit that Elusive hadn’t been able to train out of him as of yet, however.

“All this talk ‘bout Berry reminds me of another thing Ah’ need to ask ya’, Elusive.” Applejack would’ve turned to shoot the tailor an accusatory eyebrow, but a gentle hoof reminded him that he was still being measured just as the tape pressed against his forehead. So, instead he made sure to keep his tone as accusatory as possible instead. “What’ve you and ‘Scotch been up to that’s kept you from takin’ him off mah hooves all week?”

“Staying still includes the mouth in this case, Applejack. No talking.” Elusive finished his measurement of the forehead quickly, and moved the tape under Applejack’s chin; where it was forced to hover for a few more seconds.

“That ain’t an answer,” Applejack complained.

Elusive sighed. “You wanted this over with quickly didn’t you,” Elusive said as he pushed the tape against Applejack’s chin, gently forcing the cowpony’s mouth to shut. Though the measure did move slightly once more while the tailor wrapped it the rest of the way around Applejack’s head, there was no more talking for the moment.

The moment the tape fell away however…

The second he was free to move, Applejack gave Elusive the suspect look he’d intended to give him a minute ago. “So, ya’ gonna answer mah question or not?”

After shaking his head dismissively and trotting towards Applejack’s rear, Elusive responded with an unsurprisingly seductive tone. “Well I suppose there’s no harm in telling you. There aren’t many secrets between us at this point right?” He paused to snicker again, and pressed a hoof against Applejack’s flank for good measure. “Did you want all the dirty little details, or perhaps you’d prefer just a quick summary?”

Applejack was distracted a moment longer before answering. While he intended to turn to Elusive and answer him, confidently asking for details of course, his attention was instead drawn to the tail sliding with clear intentions under his chin, and, falling for its ploy, he ended up looking down at his friend’s rear instead of his face.

“Uh… Ah’ think a summ’ry will be fine.” Applejack quickly faced forward again, trying and failing to maintain his confidence as he spoke.

“Are you sure?” Elusive chuckled and slid his hoof gently down Applejack’s flank before removing it. “My you should have heard him whimper it was so hot.” He chuckled again, and the measuring tape slid up Applejack’s hind leg. It was then that Applejack began to rather loudly measure his breathing.
In spite of his attempts to keep himself calm, however, Applejack was soon fidgeting quite a bit as he tried to contain his arousal. It would be easier if he was working, but just standing there with another stallion running his hooves over his hips…

“Hold on a sec!”

Applejack jerked his head around and glared at Elusive, who was now slowly wrapping the measuring tape around Applejack’s flank with his hooves rather than his magic. “You really should stop fidgeting Applejack,” he said softly. His eyes were on the flank, and he appeared oblivious to Applejack’s staring; a fact that annoyed the cowpony. Though, after a hoof ran across his groin he was having a bit of trouble maintaining an angry expression. “It was just a spot of tea between friends after all.”

“If Ah’ didn’t know better, Ah’d think the only reason you called me in today was ta’ have yer way with me.” Applejack moved to stamp a hoof in order to gain Elusive’s attention, but a skillful caress of his balls caused him to stiffen and set the hoof down before he could raise it enough for a decently loud impact. Continued caressing of his rapidly hardening stallionhood kept him from bothering with the idea again.

The measuring tape tightened around Applejack’s waist before Elusive responded. “I assure you, Applejack, I just needed to double check your measurements for a new outfit.” As he spoke he continued to slowly stroke Applejack’s growing shaft. “Though I suppose I can’t exactly leave you unsatisfied now can I?”

Elusive gave the tape a rough tug with his magic and Applejack reflexively faced forward as he steadied himself. He turned to look back again shortly after, when he felt a sudden weight on his lower back. He saw Elusive now laying himself down on top of him. One of the unicorn’s hooves gently stroked Applejack’s back while the other continued its work on his cock with increasing vigor. The tape continued to pull Applejack thanks to Elusive’s magic.

“Ya’ ain’t exactly making a great case fer yourself.” Applejack faced forward again and took a step back. Going along with the pull of the tape, he also raised his hindquarters. When he did, he soon felt a familiar feeling as Elusive adjusted and ended up with his shaft resting squarely between Applejack’s flanks. “Ah’ s’pose Ah’ don’t mind though. Just don’t take too long okay?”

“Really Applejack? So eager for somepony with so much work to do.” Elusive leaned forward and gave Applejack a kiss on the neck. Just as Applejack flinched away and jerked his hips forward, the tape pulled again forcing his rear to press back against Elusive’s cock and his own cock to slide across Elusive’s waiting hoof.

Applejack decided against dignifying Elusive’s remark with a response; even making sure to once again steady his breathing in order to make sure no moans or gasps slipped through. He did allow the rest of his body to betray him though. Even though the tape was no longer tugging with any real force, the cowpony continued to push his hind legs up against his friend, sliding his ass along Elusive’s length.

Elusive responded by continually leaning forward; primarily so he could remain near Applejack’s ear. “Well I hardly think you’re capable of taking what I can give you with no preparation,” Elusive snickered and pulled his hips back, letting the tip of his cock linger right at Applejack’s entrance for just a moment before pulling it away. “But if you prefer this be quick than very well. I’ll make sure you’re ready to go post-haste.”

After that the unicorn pulled his hoof away from Applejack’s shaft, and the cowpony suddenly felt the weight on his lower back intensify as Elusive placed both of his hooves and most of his weight on top of him. Applejack braced himself, but didn’t protest. A part of him wanted to. Even with Elusive’s magic the idea of his partner going in dry was pretty off-putting, but he figured it was too close in coming to pull away now. Besides, it had been awhile since he’d played catcher, and he couldn’t help but find the idea tantalizing. Admittedly though, he did find his willingness to just go along with this a bit surprising.

The tape went limp and Applejack felt his hole begin to stretch. His eyes slammed shut as abruptly as the tape stopped pulling, and he grunted as he flinched away from Elusive. “That’s certainly not a confidence booster,” Elusive said, leaning forward again as he slid a hoof up Applejack’s spine. “Are you sure you want me to move in so quickly? It seems you can barely handle a little prodding.”

The probing didn’t stop of course. In fact, Elusive pushed a little deeper even as he spoke to mock his partner. However, Applejack was able to get his composure back quickly enough. His feet were planted more firmly, and his breathing was steady enough to allow him to speak. “Ah’ can take anythin’ you’ve got,” he said. With a very deliberate movement, the cowpony then lowered his head to the ground and pushed his rear even higher in the air. “Now hurry up, pardner.”

Elusive slid down Applejack when he lifted his rear, slamming his cock against a cheek and planting his head right behind Applejack’s. The movement was every bit as deliberate as Applejack’s had been of course, but it moved so fluidly it was hard to tell. “Whatever you say, dear. I’ll speed things up then.” At the last word, the magic instantly widened its girth, spreading Applejack nearly as wide as Elusive’s stallionhood would have. The cowpony was only thankful that the magic didn’t go nearly as deep, or he may have entirely lost his cool.

As it was, Applejack only lost a touch of his cool. He shut his eyes again and his breathing became heavy, but he kept his footing and no gasp, moan, or grunt escaped him. Elusive didn’t spread him any farther after that, which gave him time to compose himself the rest of the way. The wait though, did last slightly longer than he would’ve liked. By the time he was breathing steady enough to talk again, all Elusive had done since was move his shaft from the cheek back to Applejack’s hole.

“What the hay’s takin’ ya’,” Applejack complained.

A hoof slid around Applejack’s cock once more and Elusive planted a kiss on the back of his head. Then, suddenly Elusive thrust forward.

Applejack didn’t think to wonder about how Elusive managed to hit his target with such perfect aim and force, but that was mostly because he was concerned with the overwhelming burst of feelings as a cock pushed halfway up his ass in one thrust. There was pain of course, and plenty of it. That was what probably broke his cool, causing him to shout, “Buck!” more than once in the span of a few seconds.

There was also something else though; the feeling that kept him from pulling away. It was painful in itself, feeling so full. Yet it had him squeezing down of his friend’s cock in hopes of feeling it more. That pressure on his insides was irritatingly intoxicating.

Elusive kept true to his word and didn’t waste any time worrying about Applejack’s comfort; at least at first. Applejack kept his breathing steady and his hooves planted in an attempt to not show any outward signs of pain. One however, did manage to slip through. Elusive didn’t comment on it until he had gotten balls-deep, but he had noticed it almost immediately.

“Perhaps now would be a good time to take a moment,” Elusive whispered as he ran his hoof along Applejack’s half-flaccid member. It was beginning to harden nicely again after almost completely going soft upon penetration, but Elusive considered it best to not push his luck.

Applejack, however, seemed to disagree. “Don’t-hah-stop on mah account,” he said. He tried his best to relax himself as he spoke, but he couldn’t stop clenching no matter how he tried; only delaying it for a moment before clamping his ass down on Elusive’s cock again. His stallionhood hardened with every squeeze, helped along by a slow stroking from his partner.

“I hardly doubt I could move much anyway,” Elusive whispered. He made it clear how false this was by shifting as he spoke. He only removed the shaft slightly before moving back in, but he made a point of shifting it quite a bit while still inside of Applejack. To his delight, Applejack responded this time. His cock flared to life becoming fully rigid again as he squeezed even tighter than before, and his head dropped as he no doubt tried to stop himself from making too much noise. “It really has been a long time for you hasn’t it Applejack. I swear you’re squeezing me harder than Butterscotch.” He shifted again. “And you’re so tight that I don’t think I can move a single inch.”

Whether it was the mention of Butterscotch or the shifting hitting just the right spot Applejack wasn’t sure, but something triggered in him. He lowered himself even more, going so far as to rest his chin against the ground as he rubbed his rear against Elusive’s crotch. His hind legs almost extended entirely, stopping just short of actually lifting Elusive off the ground when he started to feel the extra weight. His squeezing meanwhile became more constant then before, not letting up for more than a split second for every five full ones. The unicorn took this as a signal to squeeze back, wrapping his hoof tightly around Applejack’s cock and running it across the shaft even faster.

“Buckin’-“ Applejack grunted and raised his head. His neck pressed into Elusive’s muzzle, and the unicorn took advantage of the opportunity presented to him by giving Applejack a nice hard bite. At that same moment the tape became rigid again, pulling the cowpony’s stomach upwards. Applejack gasped for just a moment as a sensory overload hit him from all sides. His mouth clamped down just short of him shout, causing the word, “Elusive,” to come out as a frustrated grunt. Then, a rather loud splash on the floor below him, and the most powerful clench yet, announced his orgasm.

“Applejack,” his lover responded with a whisper. He tried to pull away from Applejack as a hefty sigh announced his own peak. However, the clenching actually did seem to be stopping him now, and every tug away only seemed to cause Applejack to cum and clench more. After the third tug, Elusive put all force he could into it and abruptly force his shaft out of Applejack’s rear cumming as he pulled with another more stifled whisper of his lover’s name.

The tape went limp, and Applejack lowered his head to the floor again. The combination of pain and relief as Elusive pulled out caused him to let out one last extra powerful blast of semen. Elusive joined him in splattering the ground with seed after only leaving a few strings to mark Applejack’s rear and balls. A simultaneous whisper of each other’s names a few seconds later marked the moment that both had finished.

It was less than a minute later that panting gave way to a steady, and only somewhat labored, breathing from Applejack. “Elusive,” he whispered, “Get offa me.”

Elusive was still panting atop the cowpony by the time Applejack spoke up, though in Applejack’s opinion it sounded more like a continuous sigh than actual breathing. He chose to ignore the pony underneath him for a moment, closing his eyes and letting the sigh continue. Applejack allowed him to out of a belief that he actually had not heard him combined with a desire not to speak up again. It was a minute later when the steady breathing was no longer labored by anything but Elusive’s weight that he complained again.

After the second complaint Elusive did get off, though he did so as slowly as possible. He even took an extra moment after taking a seat beside Applejack before opening his eyes and glancing up at the clock. Applejack didn’t mind of course, as it gave him a second to stand up and get into a more presentable stance. “I suppose you do have work to get to,” Elusive sighed as he stared up at the clock, “Very well. Get too it then.” He waved to the puddle on the ground and trotted off to his work bench without another word. Applejack didn’t complain and went to find Elusive’s towels; preferably the expensive ones he kept tucked away in the drawers.

When he returned a minute later and got to work on the floor with the monogrammed cloth, Elusive was already busy sewing something together. Realizing he still didn’t realize what he’d been brought in for, apart from the sex obviously, Applejack took a look at Elusive’s work. Sadly, he was unable to determine what it was at the moment, as all he could see was some silvery cloth running under the machine.

“You can show yourself out when you’re finished,” Elusive said, “I would see you out, but I’m afraid I really must get to work on this. I have wasted so very much time already.”

Rather than complain about the hypocrisy, Applejack just set the towels down and nodded before turning to leave, stopping at the door. “Ah right!” he said, “Before Ah’ go. Would yah mind tellin’ me somethin’, Elusive?”

“Ah yes! I suppose I do owe you that much don’t I?” Elusive turned away from his work for a moment and shot Applejack a smug smile. “It was Darjeeling. That’s his favorite.” With that he gave Applejack a wink and returned to his work.

Applejack’s temper rose abruptly as a sudden realization and a flurry of chaste images assaulted his mind. As a result, he decided not to stay and clarify his question. He just shook his head and trotted out the door, nearly slamming it on the way out. He stopped himself just short of that though, instead closing it gently so as not to upset his friends work. After that, he shook his head again and smiled smugly to himself as he headed back to the farm and the work he’d been putting off.