Eye Opening Escort

by Some Leech

First published

High Gear is summoned to entertain a rather high-ranking official and finds herself getting a two-for-one deal...

Running the shop isn't bad work, but having a side hustle never hurts with raking in additional funds. It's not exactly like High Gear whores herself out just for kicks, but being a hulking dickmare does make finding potential clients a rather easy affair. Allowed to cherry-pick her customers, usually the cuter and more effeminate ones, there is one client she'll always make house-calls for...

Kinks Include: Futa on Male, Oral, Rimming, Anal, Cock Worship, Size Difference, Peeping, Cumflation (Cum Inflation), R63 Princesses, Femboys, Seduction, Domination, Submission, and Training...

Artwork by Tatemill
High Gear belongs to Unerro11

If you want to help support me, I have a Tip-Jar/Patreon HERE

A Peeping Penalty

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Unstraddling her bike, High Gear swung the kickstand down and leaned the machine over. Removing her helmet, setting it on one handlebar, she peered up at the Canterlot castle. It wasn’t often that she was specially requested to the capital, and even less common for her to be summoned by royalty, but she knew exactly who had put in the call. Walking to the gate, waving a silent hello to the guards, she strolled beneath the portcullis.

The sentries let the towering mare pass, offering her a curt nod. Since Prince Artemis’ proclivities were one of the worst kept secrets in the castle, and with both of the armor clad sentinels having been alerted to Gear’s arrival, they gave no resistance. Over the past months, she’d made no fewer than a dozen trips to visit the palace, all in the dead of night, so she was quickly making a name for herself as one of the diarch’s courtesans.

Shooting the duo a salute, Gear wandered into the courtyard. Looking up, gazing at the twinkling stars above, she directed her attention to one of the castle’s turrets. There, standing in an all too familiar window, stood a lone silhouette. She watched, as the figure retreated out of view, leaving a grin to creep across her face.

Into the palace, up several flights of stairs, and through the winding corridors, she marched to her destination. Though it took her a few minutes, after passing a number of soldiers and staff, she found herself before a singular doorway. Pitch black, covered in silver filigree and tracings, she gently rapt upon the ornate wooden surface.

“You may enter,” a lilting voice called out from within, beckoning Gear to proceed.

Letting herself inside, shutting the door behind herself, Gear automatically fell to one knee and bowed her head. “My liege,” she murmured, keeping her eyes on the floor.

Must you? There’s no need for such formalities. Please, stand,” the voice groaned, as it drew nearer.

Gear’s smile broadened, as she got to her feet. A lithe, somewhat effeminate stallion stood before her, though he was far from ordinary. Shorter than she, his coat was a midnight blue, while his mane and tail were a shimmering, almost ethereal azure. A singular horn sprouted from his crown, and a pair of wings lie folded on his back, marking him as the one, true Prince of the night.

As if finding one’s self before such a rare, powerful creature wasn’t captivating enough, the stallion’s outfit did nothing but emphasize how beautiful the alicorn was. Bedecked in naught but a sheer white bedlah, glittering with silver accents, the details of his figure were plain to see. His dark nipples were visible through the thin fabric of his top, as was his flaccid equipment beneath the skirt-like garment.

“And I thought you were the more customary ruler,” Gear chuckled, placing her hands on her hips.

“Twas I the more traditional noble,” Artemis purred, stepping forward and brazenly fondling the mare’s groin, “I would hardly have invited thee.”

“In that case...” Gear growled. Hooking a finger under the Prince’s chin, turning his face upwards, she leaned in and locked lips with him. Without pause, she reached around the alicorn’s back and pulled him to her chest. She’d serviced him enough to know just what he liked, so once the pleasantries were discarded, she set herself to task.

Gently kneading the package in his grip, being held firmly by the hulking mare, Artemis swooned. He’d always had a bit of a curiosity about dickmare’s before, but Gear had opened his eyes to the miraculous creatures; an enchanting combination of male and female traits, they were, for all intents and purposes, nothing more than imposing women, were it not for their typically large stallionhoods.

Months prior, having worked up the courage to contact an escort service, he’d met High Gear for the first time. Tall, powerfully built, and strikingly beautiful, the mare had arrived at his chamber in the wee hours of the morning. She’d allowed him to undress her and explore her body, a nicety on her part, though he’d had no way of knowing how much heat she’d been packing.

Having undone her pants, dragging the garment to the floor, Artemis had found himself facing the biggest cock he’d ever laid eyes upon. Easily as thick as his wrist, and nearly as long as his forearm, it swung between the mare’s legs. The sight had filled him with anxiety. Initially, he’d doubted he could handle such a mammoth log of flesh, but Gear had been beyond gentle.

By the end of that first encounter, he was a whimpering, euphoric mess. Needless to say, it wasn’t their last time meeting one another. One night turned into two, then three, and before he knew it, he’d called upon Gear’s services a roughly a dozen times. Slowly but surely, he’d developed a salacious taste for the woman, often times pleasuring himself while thinking of her…

Pulling away, retracting her tongue from the Prince’s mouth, Gear gazed down at Artemis’ heavily lidded eyes. Honestly, she hadn’t been expecting to work the night, having just laid down for bed, but who was she to deny the request of royalty - especially when it was a stallion as alluring and svelte as her host.

“Well, if your majesty wishes, I don’t see why we can’t begin,” she muttered. Pecking his snout, she released him from her grasp.

Blushing uncontrollably, nodding like an exuberant filly, Artemis scampered to his bed. Crawling upon the mattress, rolling onto his back, he expectantly peered down his chest at her. While he hadn’t initially been such a cock-hungry stallion, Gear had shown him the light. Never in all his centuries on Equestria had he experienced carnal delights like hers.

“So,” Gear began, leisurely strutting towards him, “what’s up with the getup?” In times past, she’d always found the Prince wearing stately attire, though his current outfit was far from the case; in contrast, it was positively naughty, although she certainly didn’t mind.

Caught off guard by the question, Artemis’ cheeks darkened. “I...I thought you would f...find it fetching,” he stammered, avoiding eye contact with the approaching mare.

He had, in fact, selected the garment in the hopes of pleasing her, yet that wasn’t all. Prior to calling for her services, finding his treasure trove of sex toys wanting, he’d thoroughly cleaned and lubed himself in preparation for her arrival. Paltry dildos were a pale comparison to being railed out by a hot, throbbing cock.

“Oh, it’s quite becoming,” Gear noted, easing herself onto the bed.

Resting one hand on the Prince’s knee, her other glided up his thigh, over the imprint of his package, and across his chest. His garb left nothing to the imagination, whereas her t-shirt and jeans concealed practically every feature she had - well, almost every feature. The substantial bulge at her loin was pretty obvious, a testament to her endowment and growing arousal.

“Would you like me to…” she trailed off, grabbing the hem of her shirt.

Artemis nodded, waving for his escort to undress. Standing, the dickmare hauled her shirt over her head. Deftly unclasping her bra, allowing her heavy bosoms to sway in the cool air, she unzipped her pants. Hooking her thumbs over the waistband of her trousers and boxers, she pulled the garments down her legs.

Artemis stared in open awe, drinking in the details of her pendulous dick and weighty nuts. Subconsciously, he drifted towards them, as if drawn by their siren’s call. So bewitching was the sight, that he didn’t see her reaching for his face. As she pressed a finger to his snout, abruptly halting him, he peered up at her.

“My Prince, please,” she whispered, gently pressing him backward, “allow me.”

The alicorn yielded no resistance, as he was delicately pushed to the mattress. Reclining on his back, he resigned himself to being her plaything. Penchant for well hung mares aside, he did love basking in attention. Spreading his legs, while his guest lie down beside him, his eyes locked on her hardening tool.

Gear’s breasts rested next to the Prince’s face, what with their difference in size, while her hips rested next to his waist. Walking two fingers down his chest, she tenderly squeezed his stiffening shaft. Delicately giving his length a lazy stroke, watching him fidget, her hand wandered lower. Over his coin purse she moved, until one digit circled his supple pucker. The unmistakable moist sensation she felt meant one of two things - either he’d been using a dong on himself, or he’d made himself ready for the occasion.

“Has my prince been naughty,” she murmured, sinking her finger into his rump.

“M...mayhaps…” Artemis sputtered, as a second digit joined the first.

Squirming, cocking one leg to give her easier access, he shifted in place. Closing his eyes, savoring the prostate massage, he sighed contentedly. Few things in life compared to the sinful delights of a skilled partner, and Gear was one of the best. Sliding to the side, resting his head on her tit, something warm brushed against his arm.

Peeking out, spying the blunt tip of her stallionhood, his mouth began to water. Positioned as he was, it wouldn’t take much effort to contort himself slightly and reach the thing. Licking his lips, he leaned in and craned his neck towards the vascular appendage. Kissing her glans, he ran his tongue around its ridged head.

Good boy,” Gear breathed, driving a third finger into his ass. Considering she’d soon be plowing him like a field in spring, the warmup was a fitting appetizer.

Wrapping his lips around the tip of Gear’s tool, Artemis bucked up into her hand. Humming around her length, relishing the first salty taste of her pre-cum, his pulse quickened. Forcing his head forward, he worked the first few inches of her member into his maw, making sure to scrub the delicate underside of her prick with his tongue.

Mmmph,” Gear grunted, inadvertently flexing her hips. The move drove her into the Prince’s muzzle, causing him to gag slightly. The impertinent act, intended or not, caused her to immediately withdraw. Removing her hand from his backside, she pulled his head away. “Sorry about that,” she grumbled, genuinely apologetic.

“It - Cough - it’s quite alright,” Artemis croaked, wiping his mouth. Truth be told, he’d yet to hone his skills at fellatio, although he wasn’t upset with her. “Perhaps, since you seem a bit enthusiastic, you could sate yourself with something a bit more accommodating,” he cooed, shuffling to the side. Reaching down, grasping his thighs, he pulled his legs apart and upward.

Gazing at the presentation, Gear’s stallionhood twitched. Pushing herself up, sliding off the mattress, she stood. Prince or not, the invitation was undeniably seductive and practically demanded action. The limber alicorn, legs spread, had made a request she was more than happy to oblige. Grabbing his waist, she pulled him to the side of the mattress.

Once she’d repositioned the relatively small stallion, she clutched the base of her member and leveled it at his rear. With her off hand, she guided one of his ankles to her shoulder, where she rested the limb. There was hardly a need to ask him to beg - no, his pleading eyes and enticing pose did that for him; instead, she simply pressed herself to his entrance and awaited his signal.

Artemis drew a breath, steeled his resolve, and nodded for her to continue. Relaxing himself as much as possible, he screwed his eyes closed. The pressure on his backdoor gradually mounted, causing him to wince. Despite his practice with toys, and numerous times with the mare, the initial penetration was always intense.

Harder and harder she pushed, until her battering ram-like head popped into his behind. He shuddered, as his hole embraced her thick shaft. With the most difficult part over, Gear gave him a moment to adjust to the intrusion. Wriggling in place, Artemis idly toyed with one nipple and affixed her with his best ‘come hither’ stare.

Taking his cue, Gear slowly started thrusting into her mate. Incrementally, taking her time, she plunged deeper and deeper. Enjoying the warm, snug embrace of his tush, she drove into him. Even in comparison to a great many mares she’d bedded, she had to admit, the Prince had acclimated to her size with startling speed. Before she knew it, her girthy medial ring was bumping against his taut pucker.

As his insides contorted around the immense insertion, virtually impaled by the stallionhood in within him, Artemis writhed atop the bed. The abject feeling of fullness, of being positively stuffed, sent shivers up his spine. Lying with a woman, while pleasant, couldn’t hold a candle to the sensation of being rutted by a well equipped dickmare.

Holding the alicorn’s hip, bucking with steadily growing force, Gear watched Artemis’ rigid prick flop around freely. Though it was substantially smaller than her own tool, she’d be remiss for not giving it some attention. Sliding her hand down his leg, wrapping her fingers around his shaft, she cranked his length.

The additional stimulation caused Artemis to groan, as his partner’s thumb kneaded the sensitive underside of his glans. Arching his back, feeling the girthly ring of her base taunt him, he pined for her to fill him completely. While it would be unbecoming to beg, he wasn’t fully opposed to voicing his burning need.

Noting his nonverbal plea, Gear shuffled forward. She’d bred enough ponies to recognize when a bitch, whether it be a stallion or mare, wanted to be bred. With a mighty thrust, she sent the remaining few inches of her shaft into the Prince’s backside, causing him to squeal in delight. Peeking downward, continuing to drill into him, she admired the sight.

With each backstroke, his pucker was dragged out, almost as if it fought her retreat. With every plunge, it was stuffed inward, as his body accepted everything she had to give. As entrancing as the view was, the pleasure he afforded was divine. Jacking him off, delving his depths, she succumbed to her baser urges.

As the moments passed, the dickmare’s speed and power increased. Artemis quickly found himself completely under her spell, jostling on the blankets with the impetus of her pounding hips. Her plump, ripe balls, each capable of producing untold billions of sperm, slapped against his cushiony rump. Under the combined assault of her hand on his stallionhood and the cock pistoning his ass, he moaned whorishly.

Peering down his chest, his eyes settled upon her heaving rack, but a subtle movement drew his attention away. Looking lower, towards his own abdomen, he saw an imprint rhythmically appearing and disappearing at his belly. By the stars above, had she always caused his gut to distend with her mighty cock, or had he simply never noticed? Regardless, the spectacle only elevated his arousal, driving his lust to ever greater heights.

Drilling Artemis, sensing him throb in her hand, Gear realized the Prince had to be close. Pulling back slightly, she adjusted the angle of her plunges; the subtle shift of position allowed her to more directly accost the alicorn’s prostate. As the trunk-like root of her member ground against the sensitive organ, she was rewarded by a gout of his pre-cum.

Tightening her grip, Gear pumped her hand. Knowing he wasn’t going to last for long, she decided to finish things with a bang. If he was going to cum, she was going to make damn sure it would be on her terms. Her long, steady strokes quickly shifted into machine gun jackhammering. The Prince mewled, pushed to the brink, as she brought herself to climax.

Helpless, utterly at Gear’s mercy, Artemis could sense her flaring within him. The additional pressure, threatening to break his crumbling resolve, was nearly too much to bear. A smug chuckle caused him to look to the giantess’ face. She flashed him a cocky grin, just as a sublime heat welled within his guts.

Hammering into him as she came, Gear’s movements didn’t slow - at least, not initially. Her first deluge of seed, painting his interior with her essence, was but a prelude to the impending tsunami. Hamming herself as deeply as possible, as her flare locked her into place, the dam broke. Liters of spunk coursed through her shaft, causing it to pulse with each shot, while she filled him.

The massive influx of seed demolished what little willpower Artemis had left. Screaming out, braying like a claimed mare, he came. Ropes of his jizz spattered over his chest and abdomen, with a few strands spackled on his face; though his load was pitiful in contract to the torrent being pumped into him.

The seemingly endless tide of cream surging into the alicorn had a dramatic effect. His belly progressively ballooned outward, as his body fought to contain it all. Gouts of cum erupted from his stuffed hole, slinging to the blankets and floor below. His climax rode tandem to Gear's, lasting until the the flood within him subsided.

Peering down, wiping sweat from her brow, Gear inspected the stallion. Swollen with seed, his glazed over eyes wandered aimlessly over the room. It wasn’t uncommon for their encounters to end in such a way, with Artemis drunk with cum, so she wasn’t concerned. Pleased with a job well done, she shook her head and went to move away; but something stopped her.

The faint, nearly inaudible sound of a heavy sigh caught her ear. Looking over her shoulder, towards the shuttered door of a closet, she listened intently. As quietly as possible, she hauled her softening cock from the Prince’s backside. Stealthily moving towards the wardrobe, her muscles tensed.

The prospect of an intruder meant one of two things - either it was someone who was there to do harm towards the alicorn, or potentially someone trying to get dirt on one of the two rulers. Either way, she wasn’t about to let somebody crash the party. Sneaking over, throwing the doors open, she found an athletic, snow white alicorn cowering before her.

In the blink of an eye, Gear dropped to her knees and bowed her head. The wings, an ivory horn, the magenta eyes; there was no mistaking it, she’d stumbled across Artemis’ older brother. Pressing a fist to the floor, she gulped. The last thing she’d expected was to encounter the second diarch of Equestria, given the circumstances.

“Prince Solaris, my pardon, if I had…” she trailed off, as she drank in several small details.

Near his feet, sat a bottle of lube, as well as a very slick dildo. As her eyes roamed up his body, she noticed his twitching erection and slippery inner thighs. Given the observations, there was only one reason the elder Prince would have been watching such a lust-filled event. It didn’t take a genius to put the pieces together; he’d been getting off to the display.

Meeting his eyes, noting the frightened look he had, Gear was stricken with an idea. It was clear that he’d been watching them to get some relief himself, so she was compelled to offer him aid. Without waiting for him to speak, hoping he would forgive her impudence, she leaned in, opened her mouth, and fellated him.

Solaris yelped, as the colossal mare unabashedly sucked upon his stallionhood. With the entirety of his shaft buried in her muzzle, she maintained eye contact with him. His heart thundered in his chest, his hips bucked fitfully, and his toes curled. He was putty in her hands, and he’d only just met her - well, met her in person.

Just a month prior, he’d seen the colossal mare entering his brother’s room. Curious, wondering what Artemis was doing with such a late visitor, he’d decided to do a bit of spying. Surreptitiously flying to his brother’s window, he discovered quite the shocking scene. His sibling, bent over a dresser, was being railed out by the large woman. Astonished, unable to look away, he watched the scene unfold.

Since that night, no matter how hard he tried, he couldn’t get the image from his mind. He hadn’t been angry or put off in the slightest - instead, he was unquestionably jealous. Surely a Prince shouldn’t give in to their urges, yet Artemis had done just that. From that night forward, he’d dreamt of being subjected to the same scandalous treatment, often while fucking himself silly with an oversized dildo, sometimes while watching his brother get serviced whenever Gear paid a visit.

Retracting her head, licking the glistening pre-cum from the Prince’s head, Gear got to her feet. She’d met a few reluctant stallions before, which led her to an assumption. Considering Solaris had been acting as a bit of a voyeur, while plowing himself with a rather sizeable dong, she was led to believe he wouldn’t mind getting some attention himself. The fact that he hadn’t protested was the icing on the cake, leading her to take the next step.

Rubbing his chest, taking a moment to pinch his nipple, her smile broadened. Looming over him, she casually spun in place and faced away. In her experience, it didn’t take much to break a pony like him, and that’s exactly what she planned to do.

“Mattress, now,” she chided, with her back to him.

Woefully unprepared for the order, his mind reeling, Solaris thoughtlessly complied. Meekly strolling out, doing his best to cover his boner, he moved towards the huge mattress. Gazing at his brother’s bloated and cum-streaked form, his heart fluttered. There was no way that Gear would use him like that - would she?

Confused, anxious, and turned on beyond belief, he halted next to the bed. He watched, as Gear gingerly plucked Artemis from the mattress. Gently setting the smaller alicorn to the floor, leaving the bed empty, she glowered over at him. His blood ran cold, pre leaked from his aching stallionhood, and his mouth felt as though it was full of sand, as she leveled a finger at him.

“Hands and knees…” Gear barked, a cold edge in her tone.

Obediently, Solaris did as he was told. Crawling onto the bed, leaving his backside exposed, he peered back at the dickmare. As she moved closer, hungrily eyeing his derriere, he swallowed hard. He’d seen the devastation her tool could administer, so the idea of having something that big inside of him forced him to speak.

“P...please, be g...gentle,” he stuttered, his pucker winking involuntarily.

“Oh, don’t worry, Prince. Your brother loves being my mare,” Gear snickered, walking over to him.

Squatting down, she brought her face to his alabaster behind. Sinking her fingers into his hips, pressing her snout to his rear, she dug her tongue into his backdoor. Humming into him, further lubricating his hole, he fidgeted in her grasp. His barely restrained groan of pleasure was music to her ears, spurring her to continue.

Clenching the blanket in his fingers, Solaris rocked back into Gear’s face. Lowering his torso, he balanced himself on one arm. Given he’d likely be needing one, since he’d rather not fill the air with blissful screams or marish whimpers, he reached for a pillow. Snatching a cushion and pulling it to himself, he rested his chest to the bed. Slowly, having gotten comfortable, his hand drifted towards his groin.

Sensing movement, Gear pulled her head back enough to notice what Solaris was reaching for. Slapping his ass, after wiping her face on her forearm, she pushed herself up. If the Prince wanted the full treatment, that meant he’d have to abide by a few rules - amongst which being he wasn’t allowed to touch himself during. Seizing the pillowy globes of his backside, she prized his cheeks apart and stepped forward.

“Deep breath,” she purred, sinking the first few inches of her shaft into his tush.

Remarkably, the Prince’s hole yielded surprisingly little resistance, leaving Gear to drive herself deeper. Solaris was either very experienced with toys or he’d had a fair number of flings in the past; either way, she didn’t stop until her medial ring was firmly lodged within him. Moving one hand from his derriere to the dock of his tail, using it as a handle, she began pounding him from behind.

Solaris’ eyes fluttered to the back of his head, at the abrupt manhandling. The warmth and velvety skin of Gear’s shaft was insane, better than anything he’d ever used to pleasure himself. Even if he could find a toy that matched her dimensions exactly, he knew it wouldn’t be the same. Muffling a delighted cry, he sunk his teeth into the pillow.

“Look at you,” Gear grunted, unslowing, “already moaning like a bitch.” She wanted to hear him, and if that pressing his buttons, so be it. Draping herself over him, pressing her tits against his back, she brought her face towards his ear. “Took even less time than it did with Artemis,” she whispered, licking his neck.

Her words struck Solaris like a wrecking ball, fracturing his self control. Turning his head to the side, he glanced back at her. “B...breed me,” he breathed, his voice barely a whisper.

“If you want it, you’ll have to say it louder,” Gear laughed, her motions slowing a hair.

“I said breed me!” Solaris insisted, desperation tinging his voice.

“Of course, princess…” With that, Gear began hammering into the Prince with reckless abandon. Since he’d taken her with so little effort, she saw no reason not to give him all she had to offer.

Bolts of pleasure shot through Solaris, while his body shuddered under her amorous onslaught. Lurching forward with her thrusts, his head was driven into the pillow. Grunting with every impact, drool crept over his lips and chin onto the cushion. He felt as though he was melting, like the world was slipping away; it was beyond thrilling, as well as a little frightening, but the promise of untold rapture left him begging for more.

As she had with Artemis, Gear repositioned herself a touch to batter the alicorn’s prostate. The thrill of conquest surged through her, pushing her body and mind to the limit. The head of her cock started to swell outward, for the second time that evening, as her body prepared itself to deposit another load.

Unlike with the younger Prince, whom she’d bedded multiple times, she wondered if she was the first to claim Solaris. The thought sent her into overdrive, pushing her into a rut-crazed frenzy. Screwing him for all she was worth, latching to the notion that she was his first, her nuts pulled to her groin.

An exquisite heat and pressure detonated within Solaris, as the dickmare peaked. Like an angelic geyser, her seed flowed into him, marking him as her mate. Howling, quivering from head to toe, his body bent to her will. Her uncontested might demanded that he cum, so cum he did. Without even touching himself, his prick jerked and trembled, adding his spunk to Artemis’ on the blankets.

Gear roared, hilting herself within the stallion. Though she’d climaxed not half an hour earlier, her second orgasm was just as productive as the first. Moving her hands to Solaris’ stomach, feeling it sag under the weight of her spunk, she smirked. Given how much he seemed to enjoy her time, she wouldn’t be surprised if he started calling her for servicing in the future.

Slowing to a halt, savoring the post-coitus euphoria, Gear allowed herself to relax. There weren’t many, if any, who could claim they’d laid not one but two Princess in one night, which she considered a priceless accomplishment. Still, dominating a pair of stallions was no easy task, and she’d stayed up well past her normal sleeping hour, so a fatigue settled upon her.

Pulling her semi-rigid length from the elder alicorn’s abused ass, she admired her handiwork. His hole drooled cum, gaping at the void she’d left, though she had a solution for that. Giving him a firm slap on the rear, his pucker tensed and closed, trapping the bulk of her seed within him. He was only partially conscious, at best, groaning back at her parting gesture.

“Well boys, unless you two have anything else you’ll be needing, I think I’ll hit the road,” Gear tiredly noted, stifling a yawn. Leaning over the bed, she gave Solaris a kiss, before standing and retrieving her discarded clothing.

Getting dressed, she spied a sack of bits on the nightstand nearby, but ignored it. She had a policy she’d developed over the years, one which had never let her down. The first time was always free, and something told her she’d be seeing the siblings before long. Making her leave, she couldn’t help but smile to herself. Maybe next time, she could enjoy them both at the same time…