Chapters Pinkie Pie, Escort Extraordinaire!
Not even twenty minutes later, there was a knock on the door. Jake padded to the door and opened it, his jaw going a little slack at the vision that greeted him.
“Hi!” the pink mare gushed as their eyes made contact. Blue eyes, clear as crystal. Bright, bubbly and smiling as easy as breathing. “I’m Pinkie Pie! I hear you’re in need of some fun?”
Jake’s head snapped back to reality, realizing that the mare was still in the hallway; she’d spoken in a louder-than-normal voice, alerting the entire floor (it not the whole hotel) to his request. The man grabbed the mare’s wrist and gently pulled her into the room, shutting the door behind him.
“Haha~,” Jake laughed, trying to keep his cool. “Hi… hi, Pinkie! Pie! Miss Pie? I’m Jake Kollar, but please just call me Jake!”
The whole time Jake spoke those cheerful eyes watched him, flicking up and down his body. Did they linger?
“Nice to meetcha, Jake!,” Pinkie exclaimed, shaking the hand that had pulled her in with vigor. “I hope you’re ready for a night full of fun, fun fun!”
Jake nodded, a flush coming to his face as he took in more of the mare he’d hired for the night. She was only a little shorter than him, and curvy. But not fat - just broad-boned. Her hips were wide and her bust was ample. She wore a frilly dress not unlike a tutu and a spaghetti-string halter top, with no bra visible. Across her shoulders - the strap sunk deep into the valley of her cleavage - was a shoulder-bag with a prominent three balloon symbol. In the hand that did not hold his own was a heavy amber bottle with three bright red apples stamped across. The fur that covered her was a light bubblebum pink, her hair a deeper shade of the same color. It was fluffy and curly, and would have looked a tangled mess, but the mare made it work. She looked… good. And smelled good, too.
Jake could smell her - all ponies had a distinct scent to them. She smelled like confectioner’s sugar and sweetgrass. The aroma wafted up from her, and seemed to fill the small space between them. They stood in the short hallway between the room’s door and the rest of the space.
“I am,” Jake said, giving his head a shake to once again clear his thoughts. “Sorry… this is, uh. This is m-my first time with an Equestrian.”
Pinkie’s face seemed to light up a few shades brighter than it already was, but then clicked down a few notches. Her smile remained, but the exuberance she’d oozed was corralled.
“Ahh, I see,” she said, her voice down to a more conversational volume. “Well, in that case we can take things a little slower than normal. You’re in luck - most mares from my company would be aaaall business. They’d be sweet about it, but they’d still go into the whole ‘what do you want to do’ schtick. Me? I’m all about making people feel happy! So relax, Jake - we’ll take all the time we need, okay?”
Her voice was as sweet as her scent, and Jake felt himself relax at her words. He hadn’t realized just how tense the prospect of the night’s activities made him. She’d picked up on his body language very quickly.
“Yes,” Jake said, a more relaxed smile replacing the tight-lipped one he’d been wearing. “Thank you, Pinkie Pie.”
“You can call me Pinkie,” the mare said, taking a few steps into the room. She placed the bottle on the chest-of-drawers and sat on the bed, patting the comforter next to her. “C’mon, sit down and we can chat for a bit.”
Jake did as she instructed, sitting a comfortable distance from her.
“My name is Pinkie Pie,” the mare started, pulling a knee up to her chest. Jake’s eyes flicked down to the shadows of her ruffled skirt, catching the barest glimpse of cloth between her thighs. Pinkie giggled; she’d seen his curiosity. “I’m an earth pony, and I’m from Ponyville. I love making people smile, and I usually do that by throwing parties.”
The mare shifted on the bed, giving Jake a fractionally longer flash of her panties.
“But on occasion I like to throw a party for two,” she said with a grin. Her eyes were lidded, and had a bit of smoulder to them. “A mare’s got needs - why not make someone else happy at the same time?”
“That makes sense,” Jake said, unable to stop his own goofy grin. He turned and grabbed the bottle, popping the cork with his thumbnail. “What say we have a drink? I’ve heard Equestrian cider is amazing!”
Pinkie grabbed the bottle and threw her head back, taking three long, full gulps. The elegant sweep of her neck, the trace of muscle and tendon from shoulder to breast, was hypnotic. Jake felt his loins stir. With a gurgle, Pinkie shoved the bottle into Jake’s hands. The human took a swig.
Apples. A sunny summer day. Grass and dirt, the smell of trees heavy with fruit. The clean smell of hay. Crisp, juicy, fresh apples.
“Wow,” Jake said, licking his lips. “This… this stuff is amazing.”
“Mmhmm,” Pinkie replied as she took another hit from the bottle. “This comes from my good friend’s farm. Her name’s Applejack; she’s an earth pony, like me. Best cider in all of Equestria, bar none!”
They passed the bottle back and forth until it was empty. The liquor was sweet and syrupy, hardly tasting of alcohol in the slightest. But the tang was there, a breathy ethanol bite that called to mind Everclear and gin. But none of the aftermath of those Earth liquors - only a strong heat that settled in the belly and set the cheeks aflame with rosy heat. It was delicious, and gave the right amount of buzz to both participants. Not sloshed, like Earth moonshine, but rather a satisfying sway to the world and a feeling of comfortable confidence.
“I’m getting a little warm, Jake,” Pinkie said, pulling aside one of the straps to her halter and fanning herself. “Do you mind if I get a little more… comfortable?”
Jake nodded, giving a little hiccup to underscore his agreement.
Pinkie Pie, Escort Extraordinaire!
Pinkie stood and pulled her halter from her body with one quick motion, revealing her bare torso. Her breasts were heavy teardrops, easily an E-cup, with just the barest bit of sag to them. They were capped with proud nipples the same dark pink as the mare’s mane, and they were already hard.
“AJ’s cider is soooo yummy,” she said, one hand coming up to press into her chest, just below the junction of her tits. “It helps make Zecora’s potions go down a little easier.”
Jake cocked his eyebrows, but Pinkie put a warm finger to his lips.
“Just watch, Jake,” Pinkie said, pushing the human just enough to flop him back on the bed. She straddled him, her knees on the edge of the bed to either side of his hips. “And take off your shirt.”
Jake complied as Pinkie fished out three small glass bottles from her shoulder bag. She popped two of them open and downed each in a loud gulp, flinging the thick glass vials back into her bag, which joined her halter on the floor across the room.
“The first one’s to make sure you and I don’t make any foals.,” Pinkie said, her hands coming down to Jake’s fly. She deftly unfastened his pants and tugged down, prompting the human to arch his hips to ease her work. In seconds he was naked.
Pinkie fell to her knees, her hands tracing and caressing the muscles of Jake’s chest, belly, and flanks. She raked her nails across his hips, curling her fingertips into the thick, curly hair at his crotch. Her muzzle found his groin, kissing down from his navel into the thick nest of curls just above his cock.
“And the other,” she said, each word interrupted by a series of kisses that ringed the base of his member. “Makes me nice and clean, so we can do aaaaaaall the fun stuff I love .”
“Pinkie,” Jake said, propping himself up on his elbows. She squatted between his thighs, her cherubic face beneath his cock. Her lips lingered on his sex, giving little pecking kisses across his lightly-furred balls. “Oh, god, Pinkie, please… you’re driving me crazy.”
She grinned, nuzzling up into Jake’s sex, closing her eyes and purring. “You humans smell so different… but in a good way. You smell… you. And you taste even better.”
With that, the pink mare gulped down Jake’s entire cock. He was decently-endowed, with enough length and girth to satisfy all of his previous lovers. Some had struggled to give him head, others had been rather good… but none of them held a candle to Pinkie Pie. She was a pro - her nostrils were sunk into Jake’s pubic hair, little huffs of hot air the only indication she could breathe. Her throat flexed around the head of Jake’s cock as she swallowed around it, massaging it more skillfully than any lover Jake had had. Her throat was hot, wet, and welcoming. With a slurpy gasp, Pinkie released Jake’s cock and caught her breath.
“Ghmmhmm,” she giggled, palpating Jake’s sack with her hands. “Good, mister human?”
“Ffffffuck yes,” Jake growled. “Do that again!”
Pinkie all but swallowed his cock. The heat of her throat seeped into Jake’s member, making him swell and thicken even more than usual. Her fingers found his ass, sinking into the thick, strong muscles there. She gently pulled him into her, and Jake responded by rocking his hips. Soon, they had a rhythm going.
Jake was sitting up, now, slowly fucking Pinkie’s throat. She tilted her head, her eyes almost entirely closed in bliss as she swallowed Jake’s cock, bathing his member in hot, thick saliva. Each thrust sent Jake’s cockhead deeper into Pinkie’s throat, finding even warmer, softer depths than before. On each out-stroke, Pinkie breathed, ensuring she could do this for as long as necessary.
A time or two Jake felt himself start to climax, but Pinkie’s hands were wrapped around his scrotum. When the mare felt the tell-tale twitch she slowed down, squeezing his nuts together and pulling down with just enough force to delay his impending orgasm. She gave him a wink and went back to work - she didn’t want this to end just yet. She gave his backside a playful swat, and Jake took the hint, standing up with the mare’s muzzle still wrapped around his cock.
Jake took the lead, now, thrusting faster and harder with each passing second. His hands found the back of her head, tangled in her curly pink mane. For each thrust, Jake would pull the mare’s head into his crotch, further increasing the depths of his throat-fucking.
“Fuck,” Jake said, one of many exertions of passion he’d muttered since the start. “Fuck, I’m going to cum. Please, I need to cum in your fucking throat!”
Pinkie gave a gurgle, her hands switching positions. Instead of pulling down, her hands instead jostled and massaged Jake’s nuts, helping him climax. It didn’t take long, thanks to the savage, full-strength thrusts of Jake’s hips and Pinkie’s talented throat and hands before Jake hit the edge.
The human came up on tip-toe as he came, burying his cock as far down Pinkie’s throat as he could manage. The mare continued to swallow, her muscles massaging and milking Jake’s cock for the precious gift it was about to give. Jake’s orgasm hit him like a truck, shooting a hot, heavy load down Pinkie’s throat. Each rope was eagerly gulped down, making room for the next one. Pinkie’s fingers danced along Jake’s sack, prolonging and strengthening his orgasm to maximize his output. After what felt like minutes, though, Jake’s climax finally fizzled.
The human collapsed back onto the bed, panting like he’d just finished a triathlon.
“Holy… huh… crap,” Jake gasped.
Pinkie Pie, Escort Extraordinaire!
Pinkie’s response was a giggle, followed by the lewd sounds of her licking her lips noisily. She crawled onto the bed beside Jake and snuggled up to the human, tracing her damp fingers along his chest as it rose and fell. He tried to speak, but the mare shushed him.
“Just breathe, sweetie,” she whispered. “Catch your breath; we’ve got all night to play.”
Long minutes ticked by, punctuated by Pinkie showering Jake’s neck, shoulder, and chest with little kisses. Her hand found his sex and cupped it, but the gesture wasn’t overtly sexual… just intimate. Jake finally drew a deep breath and lifted himself up to give the pony a peck on her fuzzy pink cheek.
“All better,” Jake said, his voice only a little ragged. “Now how ‘bout I return the favor? No sense in you having to do all the work.”
“Oh?” Pinkie said with a mischievous grin. “What did you have in mind, mister?”
Jake looked down at the frilly skirt that Pinkie still wore, and then back up to its wearer.
“How about you let me see what you’ve got under there… up close and personal?” the human growled. Before Pinkie could respond Jake’s hands were on her. He flipped around on the bed until she was above him, his head between her thighs. His hands were on her hips and he tugged down, gently. Pinkie giggled and blushed, but obediently shuffled forward until she was squatting over his face.
In the shadow of Pinkie’s ruffle-skirt, Jake saw the treasure the pink mare had teased him with before. A pair of blue-and-white striped cotton panties, with a telltale damp spot that had spread considerably.
Jake pulled down, lowering Pinkie’s sex onto his face, his nose and lips trapped by her warm, slick labia; only a thin layer of cotton separating their two bodies. He inhaled deeply, his nose once again filled with a complex bouquet of aromas. She smelled sweet - like sugar and syrup and cotton candy. And a wonderfully earthy, feminine aroma; the unmistakable smell of a woman in need of intimacy. His deep whiffs made the mare giggle and laugh, but she cooed as he nuzzled her thick, warm lips all the same.
“Does Jakey-wakey likey-wikey?” she asked in a sing-song voice.
Jake nodded, his hands slipping up to tug aside Pinkie’s panties. With one long, lazy lick he lapped all the way from clitoris to taint. She tasted even sweeter than she smelled; her thick juices were like honey on his tongue. At the end of his initial exploration, an inch from the dark cleft of the mare’s ass, he paused. She whimpered and wiggled above him.
“K-keep going,” she said. “I really really like it when ponies play with me there.”
Jake needed no further instruction; anal was one of his favorite meta-activities, and finding this amazing lover was into it, as well, relit the fires of lust in the human’s belly. He kissed the tight ring of muscle between Pinkie’s lightly furred cheeks, feeling their thickness and heat. The potion she’d drunk earlier had, indeed, cleaned her thoroughly - all Jake detected was the taste of Pinkie’s skin.
His tongue slipped out, circling the fleshy ring of her asshole, savoring its warmth and softness. She wickered above him, a stuttering horsey giggle of pleasure and joy. The sound was like music to Jake’s ears, who took it as a sign to continue. The tip of his tongue pushed against Pinkie’s pucker, which was deliciously resistant. But with a little grunt from his partner, Jake soon found his tongue pushing inside of her. Instantly it was warmed by the intense heat of Pinkie’s body. The mare gave a deep groan and pushed down, sitting hard on Jake’s face and helping the human’s tongue push deeper inside of her.
Her fingers came to her vulva and began tickling her clit, swirling her thick juices in circles and spirals around her hot, throbbing button. Jake could feel the pressure and motion of it all against his chin - he could see nothing save barely-pink darkness. All he could taste was her ass. His world was suffused with this mare and her sex. Her desire, her lust, was everything.
It wasn’t long before Pinkie’s fingers and Jake’s tongue did the trick, and the mare bore down with a gushing orgasm, soaking the human’s face with a sticky spray of female ejaculate. Her knees went rubbery, causing Pinkie to collapse on the bed, panting and giggling, her eyes half-lidded and out of focus.
Jake padded to the bathroom to towel off, and returned to find Pinkie tugging off the last of her garments. She was naked, now, knees still wobbly and drawn together. It made her look even sexier, seeing the aftershocks of their mutual efforts rippling through her. Jake’s half-hard member throbbed to full erection, however, when Pinkie rolled onto her hands and knees and lifted her tail. She popped the cork on another potion bottle and dribbled the thick, silvery contents down the dark pink cleft of her ass.
“Fuck me, Jake,” she whispered. “Please, please fuck my ass.”
Jake hopped on the bed, using his fingers to scoop up the magical lube and ensure both her asshole and his cock were well-greased. Pinkie was babbling and whimpering, rocking back and forth on her knees, obviously in dire need of having her ass filled. She gave a squeal of delight when Jake brought his slick cockhead to her pucker.
Despite the fun they’d just had, Pinkie’s asshole was vice-tight. At first, Jake wasn’t sure he was going to fit, but then the lube worked its magic and he slipped inside of her. It was slow going; Jake was well-versed with anal sex, and carefully metered his penetration to give the mare all the time she needed to accommodate him. Even taking it slow, though, Pinkie’s walls gripped him tight. The warmth Jake had felt with his tongue intensified the deeper his cock sank; by the time he hilted within her it felt like velvety lava gripped him. It was intense, but far from unpleasant.
“Ohhhh, Celestia I love that fullness beneath my tail,” Pinkie moaned. Her voice was deeper, huskier. Jake’s hands explored her beautiful back, stroking and scratching and gripping her strong muscles beneath her pink fur. They lay there for a long moment, the magical lube sinking into Jake’s skin and ensuring he stayed rock-hard, until Pinkie gave a little wiggle. “Okay… let’s try some thrusting, Jakey.”
The human nodded, pulling back gently. The sensation was exquisite, a silky-smooth glide from the tight, hot confines of Pinkie’s ass back into the relatively cool air of the hotel room. Jake reversed course, and pushed back into Pinkie. Human and pony moaned at the feeling, and both began to speed up.
Their hips rocked and rolled, helping one another find the right rhythm, angle, and depth. Jake knew he shouldn’t be this hard this soon after the interstellar blowjob Pinkie had given him earlier. And he definitely knew he shouldn’t be lasting this long. He didn’t have any problems with stamina, but a quick glance at the clock beside his bed showed he’d been butt-fucking his pink pony partner for the better part of half an hour.
They were pistoning together faster than Jake could believe. At this point he should have been feeling the burn; he should be exhausted. But he felt fine - he felt incredibly horny and had enough energy, it seemed, to fuck all night. Pinkie showed no signs of slowing, either, meeting each thrust with equal force and gusto. The lube needed no replenishing; each thrust was a buttery-smooth as the first one had been. Each thrust forward sent Jake’s heavy sack slapping into Pinkie’s slick labia, sending spatters of honey splashing across their thighs and lightning flickering down the mare’s spine.
“Oh, Jakey! Jakey!” Pinkie yelped, her voice crescendoing. “G-gonna c-cum!”
Jake felt her orgasm; a sudden flood of warmth around his cock, combined with extreme tightness, triggered his own. With a positively inhuman roar Jake let loose, emptying his balls deep within Pinkie’s ass. This was even longer than his first orgasm of the night, as rope after rope of hot spunk shot from his cock and splashed into the mare’s depths. Pinkie’s walls fluttered and squeezed around Jake, milking him as he came. Her hands came to her belly, feeling the warmth spread up into her with every spurt of cum. The two lovers howled as they came, and then collapsed in a tangled heap of limbs, but still connected beneath the mare’s tail.
Pinkie Pie, Escort Extraordinaire!
Jake could only pant, crouched as he was over Pinkie Pie. She was on her belly beneath him, her flanks soaked in sweat and heaving with each breath. Jake, too, was covered in sweat, cool beads of the stuff dripping from his nose and tickling his back as it fell from his hair. The bed was utterly ruined, soaked as it was in Pinkie’s cum and their combined perspiration, not to mention how utterly tangled and tousled the sheets were. He could hardly believe the damn thing hadn’t cracked beneath them, thanks to the speed and strength of their rutting.
Pinkie gave a weak wiggle, which Jake took as a signal to try and get off of her. He managed to do so, laying back on quivering thighs. She pulled herself off of his cock with a rude, wet plop, carefully angling herself so only a little of his cum gushed from her gaping asshole. With her hips on the bed, and her hands and knees on the ground, the pony drew her bag to her from where she’d thrown it on the floor earlier. After rummaging around inside of it for a few seconds she triumphantly brought out a stout metal plug, which she promptly shoved between her fuzzy pink buttcheeks. The buttplug was bigger than a starter model, but not so large as to be outrageous. Jake watched it sink between Pinkie’s cheeks and settle against her skin, a blood-red jewel set in the silvery metal catching the dim light of the hotel room.
“So none of your yummy cum gets all over this nice room, Jakey,” Pinkie giggled. Her stamina amazed him - not even five minutes after getting ass-fucked to heaven and back, and she was up and moving. Jake could hardly lift a finger; he’d flopped back down onto the damp bed as soon as Pinkie had gotten out from under him. His cock was still half-hard, though, lolling to one side like a curious but distracted python. Thick gobs of his cum still clung to it, along with the super-lube Pinkie had slathered her asshole with.
Pinkie gave his cock a hungry stare, licking her lips as she squatted on the ground, testing the plug’s seal. She seemed satisfied, and crawled back up onto the bed. But rather than snuggle up with her lover, she instead pushed his thighs apart, resting her ample breasts on the human’s legs just below their junction.
“P-pinkie,” Jake rasped. “What are you doing? I… I don’t know…”
“Hush, Jakey,” Pinkie said with a conspiratorial wink. “It shouldn’t come to any surprise to you that a mare who loves having her tailhole filled would love to taste herself after a romp like that. Mmm… just look at all those yummy juices… I can’t help myself!”
Pinkie opened her stubby muzzle wide and sensuously began licking every last drop of goo from Jake’s cock. Despite his exhaustion, Jake felt the last dregs of the magic lube soak into the sensitive flesh of his shaft. Combined with Pinkie’s renewed enthusiasm - and the taboo of ass-to-mouth to boot - Jake found himself returning to maximum hardness in seconds. His nuts gave an almost-painful twinge, but Pinkie’s skilled hands found them, massaging and kneading them into production once more.
Jake’s world disappeared. There was nothing but his body and Pinkie’s. The bed ceased to be, the room melted. His cock became the focus of his every thought, until even those fizzled away. Pinkie’s affection was complete - Jake had never experienced such a devoted partner in all his years of activity. It was obvious she was enjoying herself - giving pleasure seemed to be the primary mechanism for her to receive pleasure - but the lion’s share of her energies were utterly focused on bringing Jake to a third mind-blowing orgasm in as many hours.
No nook, no cranny, of Jake’s sex was left unexplored. Every drop, every strand, of their mingled juices disappeared down Pinkie’s warm, welcome throat. Her tongue explored Jake’s foreskin, each bubble of cum eliciting a squeal and a purr of appreciation. Her fingers felt the tissues and structures within his scrotum, exploring him and learning exactly what kinds of pressure and rhythm felt the best for the human. Jake should have been dry - he should have been in rather considerable pain - but Pinkie’s enthusiasm and skill had Jake not only hard, but willing and able to give the mare exactly what she needed.
Once Jake’s cock was sucked clean, Pinkie hefted her warm, pillowy breasts up Jake’s thighs until they wrapped around his saliva-slicked cock. With the last dregs of the magical lube, Pinkie coated Jake’s cock, and by contact her own cleavage, with the slippery stuff. What had been a pleasantly warm, soft space became as slick and tight as Pinkie’s mouth and ass. The mare squeezed her tits together, trapping Jake’s cock in the too-narrow tunnel between her boobs. It should have been too tight; it should have been uncomfortable… but it wasn’t. It was heaven.
Jake felt Pinkie’s heart throbbing through the fleshy jugs that trapped his sex. He felt his own cock respond, pulsing in time with his own heartbeat, synchronizing with hers. Jake had heard of heart connections and other such nonsense when he was back on Earth, but the palpable bond he felt forming between himself and his lover was overpowering. This wasn’t love, or even lust - it was something deeper. A primal connection that was only describable with a single word: magic.
After an agonizingly long titjob, Pinkie brought Jake once again to the very brink of orgasm. The whole time she’d been whispering to him, encouraging him and complimenting him on his stamina, how beautiful and big his cock was, how good it felt to touch him this way. Jake didn’t want it to end - this bliss was almost too much. But Pinkie was a generous lover, and made sure to bring about her partner’s climax at just the right time, lest the pleasure turn to pain.
With a final hug of Pinkie’s strong arms, Jake felt his cock embraced by the mare’s fuzzy, warm titflesh. Even his balls were pressed between them - safe and warm, squeezed with just the right amount of pressure. It was as friendly as a hug and as intimate as sex. It felt… right. Jake had no way of speaking, no way to warn Pinkie, but he finally understood it didn’t matter; this was what she wanted. All he had to do was let go.
Jake’s final orgasm unfolded within him, a rising tide of pleasure that expanded from somewhere behind his belly button out to the tips of his fingers and toes. In Jake’s mind, he saw a warm, golden light fill his body. And it began pouring from him, into the safe, dark space where Pinkie’s heartbeat was steady and strong. That pounding was like a beacon or a magnet, drawing the light/orgasm from Jake’s body into Pinkie’s, centered in the secret space between Pinkie’s breasts.
Jake breathed, in and out, spilling the absolute last of himself into Pinkie’s short, soft fur. She moaned and purred, a wordless thank-you of appreciation and joy, as the human’s cum came in heavy, hot ropes. From the confines of it’s fleshy prison, Jake’s cum spurted up and out of Pinkie’s cleavage, splashing her neck and chin, only to fan out and fall across the tops of her breasts. At long, long last, Jake’s cock stopped spurting, and the mare released him. A thick strand of cum connected their bodies, which Pinkie regarded with a smile as she gently massaged the rest of Jake’s cum into her fur.
Pinkie Pie, Escort Extraordinaire!
The two lovers lay together for a long time, catching their breath and riding the wave of their pleasure. After an hour or so Jake had recovered enough to pull Pinkie into the shower with him. The two lovers took their time bathing one another. Jake took the opportunity to explore his lover’s sex more thoroughly, as it had been woefully neglected over the course of the evening’s activities.
On his knees, Jake craned his head back, his tongue slithering deep into Pinkie’s pussy. Her thick, warm labia were a dark, dusty pink; they spread wide, kissing his face as he tasted her syrupy juices. The human was no slouch when it came to oral - and though he didn’t have Pinkie’s supernatural ability to bestow pleasure, the sounds she made clearly communicated just how much she was enjoying his attention.
Jake watched through half-lidded eyes as his lover’s body undulated above him, involuntarily rippling as he drank not one, but two orgasms from her flower. She gushed into his waiting mouth, spurting her juices all over his face and making quite the mess. Neither minded, given they were in the shower; Pinkie’s appreciative tongue and the hot water soon made quick work of the mare’s cum.
The two lovers exited the shower and began drying. Jake checked the clock on the nightstand - miraculously not knocked over, despite the marathon love-making that had happened earlier - the sun was still a few hours from coming up.
“As much fun as I’m sure it would be to go another round,” Jake said as he toweled off. “Could I suggest something ridiculous and just fall asleep next to you?”
“Of course!” Pinkie said from the bathroom. “Zecora’s potions are amazing, but they can really take a toll after you’ve had a lot of play-time.”
Enough time had passed to dry the bedsheets of their previous dampness. Wrapped only in a towel, Pinkie hastily constructed a crude blanket fort. Casting her garment aside, the pink mare darted inside, all but dragging Jake behind her. There, in the dark, the lovers cuddled and kissed, using touch alone to feel one another’s bodies. Exhaustion loomed, however, cutting their impromptu make out session short as they fell asleep in one another’s arms.
In the morning, Jake awoke to find himself alone. The bright sunshine filled the room with golden fire, tinging the furniture, walls and floors in a thousand shades of dawn. Bleary-eyed, the man pulled himself from the nest Pinkie had pulled together the night before, hobbling naked over to the parted curtains.
Like all mornings in Equestria, this one was busy and bustling. There were cries and shouts of commerce - farmers bringing their crops to town for market, craftsponies hawking their wares. Business. The reason Jake had come to this place. But that had a different light, here. Business wasn’t the same in this world as it was back home. There was something almost innocent about the way people lived and worked here; a simple joy in doing things Jake hadn’t really ever felt.
Jake had wanted to buy sex last night; a simple exchange, one he’d done plenty of times back on Earth. Pleasurable company. Sex as a service - one provided by a skilled worker for a generous amount of compensation. But that wasn’t what Jake experienced the night before. That was something far more real… far more true than he’d ever felt. There was a joy in Pinkie’s attention, a pride in the pleasure she helped manifest. A joy that Jake wanted to keep forever in his heart so that it would forever color his life in a positive way.
It was then Jake noticed the note. It was folded up on the nightstand, next to the clock and the crystal. It was sealed with a puffy sticker of three balloons, two blue, one yellow. He opened it.
Dear Jake , it read.
I wanted to thank you for last night. It was super-fun! I’ll be honest - I’ve never been with a human before. Would you believe I was actually nervous? Isn’t that the funniest thing you’ve ever heard? Especially considering the most important lesson my Grannie Pie ever taught me about being afraid… but that’s another story entirely.
Actually, that reminds me of a good friend of mine. Her name is Twilight Sparkle, and she’s super-smart. But when I first met her she was only super-smart. She didn’t let anything else fun or good in. That’s why she came to us, actually, was to learn about all the good things other ponies… other people… can bring into your life.
When I was with you last night - when we were playing - it was like I could see inside of you. Lots of ponies have a good sense about others; mine’s especially fine-tuned, ‘cause I have to learn about people so I can make them happy. And I saw that you weren’t happy. Well, sort of. You were happy, but you weren’t? Like you were missing something. I wanted to fill that hole, a little… even though you were the one filling mine! Sorry, that was too funny to pass up.
Take care, Jake. Enjoy Equestria - I think it’ll do you a lot of good.
--Pinkie Pie
PS - No charge!
Jake stared at the letter for a long moment, and then began to laugh. Humans experience many sorts of laughter; pained, wry, bitter, ribald. But this come from somewhere deep, somewhere Jake hadn’t realized he’d forgotten. Somewhere Pinkie helped him find. Jake laughed and laughed and laughed, happy for the first time in what felt like forever.
It was, without a doubt, the best one night stand he’d ever had.
Pinkie Pie, Escort Extraordinaire!
Most people wouldn’t think a magical world filled with laughter and sunlight would classify as a business opportunity. In Jake Kollar’s eyes, those people were hilariously wrong. It hadn’t even been a year since the portal opened to Equestria, but in those few months Jake and others like him had landed huge contracts with the denizens of the alien world. Earth and Equestria were two very different places; raw materials alone were vastly dissimilar. Human science and pony magic were tentatively compatible, and there were opportunities abound for a bright young businessman to make a tremendous amount of money.
Jake had originally come through to offer the ponies of Appleoosa a deal on building-grade steel, and had managed to button up the contract in a little less than a week. He decided to stay another week to take in the sights and see what collectibles he could pick up. Rich humans were buying artifacts and curios from the world of the horse-people as fast as they hit the market, often at 1000% markup, minimum.
Jake was one of several humans in Appleoosa, but he rarely saw his compatriots. It was better that way - less interference for business deals. He’d spent much of the day wandering around town, conversing with the locals and buying about a dozen knick-knacks from the little burg’s shops.
Today had also been the first day he’d really allowed himself to relax. Contract negotiations with the horse-people here required no small amount of concentration thanks to the numerous distractions this world regularly produced. Keeping everyone involved and concentrating on the wording of a clause versus, say, an impromptu tea party or a sudden invasion of dangerous desert wildlife that required a literal song-and-dance routine to disperse was a challenge.
Today had also been the first day Jake had paid attention to the occupants themselves. At first they were a riot of colors and images - each pony was a different color. That fact alone gave humans headaches when they first came through. Jake had taken the time to make the adjustment, but today he’d actually been able to tell them apart. In doing so, Jake realized something.
Most of them were female. And attractive.
Young, healthy, and athletic described a sizable portion of the populace of Appleoosa, and Jake had no reason to suspect this was a unique locale. The initial reports sent back through the portal by scouts and diplomats were full of praise for the hospitality and openness of the pony-folk, as well as their general attractiveness. Jake had yet to see a member of the three races that wasn’t physically attractive.
As a result of this simultaneous scrutiny and relaxation, Jake was horny as hell. Surrounded by a mostly female populace of physically active women had worked Jake’s desires into a hearty flame. He was far from a virgin - there were plenty of human women he’d slept with - but he’d yet to have any sort of intimate contact with a pony. They were very into physical contact, too. They were constantly hugging, holding hands, or throwing an arm around someone’s shoulder. It was just the thing to do. Humans were nowhere near as touchy-feely as ponies… at least, no human Jake had ever grown up with or worked alongside.
Memories of firm, yet yielding flesh pressed against his own in friendly hugs, or the soft touch of a hand on his, danced in his head as he got out of the shower. His room was a modest space in Appleoosa’s only inn. During the day, the small building was filled with the sound of saws and hammers (no power tools here just yet) as work crews of strong-backed ponies labored to expand the inn. As one of two towns nearest the portal, Appleoosa was going to become a new boomtown, and the community knew it.
Jake sat on his bed in a towel, his erection proud and stiff between his thighs. There was no TV or computer - there just wasn’t the infrastructure for that yet. Masturbation was certainly an option, and Jake considered his imagination to be more than adequate, but that was when he got an idea.
“They couldn’t,” he muttered to himself. “Would somewhere as wholesome and good as this place really have prostitutes?”
Jake eyed the crystal on his nightstand that connected to the front desk. In lieu of electricity and its wonders, the folk of Equestria relied on equal parts unicorn magic and clever, yet simple, machines for convenience. He waved his hand across the facets of the thing and watched a warm green radiance blossom within it.
“Front desk,” answered a female voice with a strong Western accent. Just a hint of a rasp to it. Jake wondered what she’d sound like when she orgasmed, and then shook his head, shocked at the sudden intrusiveness of the thought.
“Uh, hi,” he said after clearing his throat. “This is Jake Kollar in room 207. I was… er… wondering something.”
There was silence on the other side for a few seconds.
“Yesss?” the concierge answered, confusion creeping into her voice.
“Sorry… this is, er, kind of awkward,” Jake stammered. He gave a sharp laugh, amused at his own bashfulness. He’d done this sort of thing before, but on Earth. With humans. “This may sound odd, but do you know what an… escort service is?”
“Of course, sir,” the woman answered.
“Oh, thank god,” Jake said with a sigh. “I was worried the concept didn’t exist and… yeah.”
The woman on the other end of the line gave an indescribably adorable giggle.
“No, sir, I promise you stallions have need of pleasurable company as much as human men,” she laughed. “There’s a service we use that can send somepony up to your room shortly. Stallion, mare, or both?”
The forwardness of the question - and the fact that his own gender didn’t factor into her question in the slightest - made Jake smile. This place was so much different from Earth - so much more tolerant.
“A mare, please,” he said, hardly believing the words coming out of his mouth. “How… should I pay her?”
“Any charges she incurs will be added to your bill, to be resolved at the end of your stay, Mr. Kollar,” the concierge said, professional as always. But a hint of warmth had creeped into her voice; the smile through which she spoke was easily heard. “Will there be anything else? A bottle of cider, perhaps?”
“Yes,” Jake said after a moment’s contemplation. “Could you send it up with her?”
“Of course,” the mare answered. “Enjoy your evening.”
Jake flopped back down onto the bed, staring up at the thick wooden beams of the ceiling.
“I am going to have sex with an alien horse-woman,” Jake said aloud to himself. “This… is not what I was expecting to happen today.”
Pulling himself to his feet, the human finished towelling off and put on a fresh set of clothes - boxer-briefs, a pair of elastic-banded shorts, and a solid color t-shirt. Nothing fancy, but enough to be comfortable. He sat, and waited, trying his best to keep his heartrate down as he contemplated the night that was to come.