Casino Derpy Royale

by Steel Quill

Rating: mature
Tags: Sex, Slice of Life, My Little Pony: Friendship is Magic, Featherweight, Anthro, Romance, Porn, Derpy Hooves
Length: 8734

Featherweight goes to a casino to do a photo job. Derpy gives him the VIP treatment.

As it turns out, trying to build one's photography portfolio takes a little legwork, and a lot of photo work. Featherweight is still trying to get his name out there, and when you're at his level, you take what jobs you can get. In this case, the job is helping create some positive press for the newly opened casino run by the infamous Flim & Flam Brothers. Thankfully, the job seems legitimate this time around and for once, not made as shady as the twin stallions' reputation would seem to be.

But when part of the job goes off the rails due to the planned model for the photoshoot going AWOL, Featherweight has to think fast. He finds his salvation in a familiar face. A familiar, blonde, curvaceous, face. With Derpy on board, maybe things can work out after all.

A comeback story after six months and a sequel! What a humdinger. Cover art designed by Zwitterkitsune! Pre-read by Greymane Shadow!
Featured 6-23-23! Thank you very much!

Tags/kinks: MxF, Anthro, Older Female x Younger Male (18+ years of age), Casino shenanigans, Bunnygirl outfits, Thicc MILF, Stripping, lap dance, huge tits, big butt, fingering, breast/tit worship, sweat, oral worship, dirty talk, cowgirl, creampies, passionate sex, happy ending.

Published 2023-06-22 18:30:03 UTC
Last updated 2023-06-22 18:30:03 UTC

Casino Derpy Royale

You can certainly say Ponyville has had its fair share of curveballs over the years. Surprise visits, unexpected events, the occasional world ending catastrophe. Fortunately, after the world finally found a way to settle in the aftermath of the final conflict between the Elements of Harmony and the combined forces of Tirek, Chrysalis, and Cozy Glow, things seemed to be far less chaotic. Discord would’ve protested against such an idea, but he had Fluttershy to occupy such attention far more effectively these days.

However, the opening of the Flim and Flam Grand Hoof Casino was a fair contender to gain his approval.

The sudden appearance of such a creation, from two stallions of a reputation most considered tarnished at best and deviously wicked at worst, evoked a surge of replies from the community. The elders were wary of having such a place that encouraged wasteful behaviors bringing harm upon their community. The youths were excited for it, as any new creation or event in the farming town was seen as something to look forward to. The bickering went back and forth for a time, until finally a voice of reason came forward. It was by Applejack’s own words that The Grand Hoof Casino was allowed to settle in.

“I trust these two ponies about as far as I can kick ‘em, and I can kick pretty darn far. And so they’ll know what happens if they try to swindle this here town. Right boys?”

Flim and Flam were happy to get the Element of Honesty herself in on helping make their project happen. Of course, Applejack’s business sense stayed atop the twins’ ambitions like the metal turnstile of a water hose. Any time they started to get a little messy or out of control, it was AJ who’d put things in order. The delicate balance of exciting gambling and honest policy-making was a curious blend for such an enterprise. But the benefits to the community showed themselves aplenty. New jobs, a flow of traffic in tourism and curious patrons, and wealth that supported the town via the glorious method of proper taxation.

Featherweight’s involvement, however, had nothing to do with any of such things. His position in the grand scheme of life was far simpler.

“Good thing I don’t have that much money to spend, or I’d be all over this place.” He muttered to himself as the pegasus walked in through the front doors of the casino. The main hall sat tall, reaching three floors high and spreading out far enough either way to make for a healthy walk in every direction. Here and there and almost everywhere, the whole building spoke of lavish wealth and fortune. Red velvet lined furniture dotted the lobby, giving plenty of spots for individuals to rest their weary feet after trying their luck in every fashion.

The floor of the casino was carefully tiled work of black and white that formed various patterns along the floor, an obscure artistic take on things like a river or perhaps a sunrise. The pillars that reached all the way up to the ceiling were a maroon color with gold seemingly woven around each in a flowery fashion. Featherweight took a shot of the lobby before approaching the front counter, his steps light as his tennis shoes gave the occasional squeak. The receptionist desk was where you could get yourself all kinds of things: spare tokens to play, keys to one of the VIP rooms, and perhaps good customer service. The smaller pegasus ran a hand through his brown hair to try and settle it in a more nicer fashion before stopping at the counter.

“Excuse me, miss?” He greeted the uniformed mare, who looked down from her clipboard she was writing on to view him over a pair of glasses. Her own cinnamon brown mane was pulled back into a professional ponytail, and she gave a polite if slightly forced smile at him. “My name is Featherweight. I was called here to do some photo work for Mr. Flim and Flam, to help promote the casino?”

“Ah, Mr. Feather. Just a moment.” She replied, setting it down and retrieving another clipboard from under the desk. “Do you have some form of ID to verify yourself?”

“Uh, yeah. One sec.” He dug into his pockets and fished out his wallet, parting aside old receipts and change to dig out the ID card he’d had made for moments like this. The mare took it up, inspecting it for a moment before squinting down at him. He managed a polite smile at her. “It’s Featherweight also. Just one word.”

“So you are indeed. A little young for this kind of business, aren’t you?” She questioned.

“I like to think my youthful good looks help me in a lot of ways. But photography is all about things both young and old, you know. The real trick is finding the beauty in both things.”

“How poetic. But, everything does seem to be in order.” Featherweight spotted her nametag as she handed back his ID, identifying herself as ‘Cocoa’, while also giving him a badge to hang around his neck with a black cord. “Misters Flim and Flam have granted you a full pass to the facility, equivalent to being a VIP assigned in our care. You are free to move about the area, and have access to most services and places save for our most secure spots.”

“Right. No flash photography if I see the big vault with the giant money bags, huh?”

A smile flitted over the mare’s muzzle. “It would be appreciated. I imagine your photos will be of the people and the building itself?”

“That’s the plan.” He told her. Filing a request to try and bolster his own repertoire had been daunting enough, but having the good word of Applebloom and thus AJ by extension did a lot to help propel him up to such a spot. His lack of connections to any of Flim and Flam’s past activities in other cities also likely helped so they wouldn’t think he was a potentially bad agent. His photos from the New Year he took just a few months ago had done very well amidst the local populace, but he wanted to expand to show others beyond Ponyville what he could do. “Out of politeness, Ms. Cocoa, would you like me to avoid photos here of the front desk area?”

“Why, we are more than happy to show our smiling selves to the world, Mr. Featherweight.”

“I know. And I know long hours on jobs in a uniform. So instead of feeling like I’m another stallion to make sure you’re absolutely perfect in front of, maybe I could treat you like a regular person like myself, and give you a break? At least for my behalf.”

Cocoa’s expression relaxed, and a genuine smile showed on her lips as her stare eased. “Well, when you put it like that. We really don’t mind, but your consideration is really appreciated.”

“No worries.” He straightened and gave a bow of his head. “I’ll go on in, then. You have a good day, Ms. Cocoa.”

“And you as well, Mr. Featherweight.”

Once Featherweight had gotten past security, who had checked his camera over thoroughly before handing it back to him as well as his camera bag, he was allowed a moment to just enjoy the sights of the casino proper. The main room was gonna be his focus, and Celestia, did he have a lot to work with. From wall to wall, there were places where ponies were flowing by, congregating in huddled bunches or occupying a full array of seats for a table to play at. Slot machines lined a large section of the room in wide rows, allowing for room to walk between and around each line. The endless metallic clinking and clunking of randomized chance was a part of the humming energy of the room, energetic music playing over the loudspeakers.

The photographer took his time just to soak in the sights, making a mental note to come back to the entryway for a full view of the hall. He weaved his way in and out of the path of many a pony, some looking like they were visiting from Canterlot from the aura of smug success and rich pockets they bore. They had dresses and suits worth enough to cost Featherweight five new cameras, he was sure, let alone any jewelry they wore to show off with. In that same vein, though, some familiar faces did happen by once in awhile. He could’ve sworn he saw Lyra being dragged off a machine at one point by her partner and wife, Bon-bon, the latter ignoring the former’s pleas for more money to “finally break the bank”.

The sudden collision of what felt like soft cloth against his face made those thoughts come to a stop though, as well as the sheer plush of the body beneath that satin pushing against him. But being someone used to being bumped around, Feather wasn’t sent sprawling to the floor this time. Instead, he merely rolled to the right, getting out of the individual’s way and looking up at them. His eyes widened in sheer surprise at the face he recognized, her criss-crossed eyes looking distressed as she regained her footing and managed to keep her tray from falling to the floor.

“D-Derpy?”

“Oh! Feather!”

The bubbly mare’s exclamation of his name had his heart pounding as much as the sudden rush of appreciation for the attire she had on. Gone was the motherly mare’s casual attire and somewhat muffled clothing; in its stead, a much more tantalizing reveal played out for Featherweight’s eyes. Her long legs were bare to the world, no fishnets or stockings to cover the gray fur or the bubble cutie mark even at her hips. The bunny girl attire did it’s job to keep her decency covered, but Derpy’s figure was putting a fair effort in still showing off her exemplary curves. The bodice of the suit was struggling to fully contain her ample bosom, each movement she made making them shift in pleasant ways. Combining this with her blonde hair and the touches of black lipstick and eyeshadow, she was a walking treat for all.

She made her way over to him and was beaming as she beheld his awed look. “Fancy running into you here, handsome!” She giggled out before leaning down to better whisper to him. “I’ve been practicing my floor girl talk. How do I sound?”

“Derpy, you’re…wow. Uh.” Featherweight needed a minute to get the first hormonal response, followed by an equally urgent second, out of the way so he could talk properly. “You look amazing. The line’s a nice touch. But what’re you doing here? I never thought you’d take up this kind of thing.”

“Well, it’s not my usual kind of thing. But, a good paying side job is nice to have! I just gotta walk the floor, make sure people get drinks and snacks, entertain the occasional high roller,” she listed off, tilting her head at the last one, “though they sometimes pick other girls. But I like to think I’m lucky sometimes!”

“I mean, I could definitely say I was lucky before…” he trailed off, looking aside as his cheeks warmed. It was hard to forget that he had given his first time to Derpy, while they were celebrating New Years just a few months ago. Ever since then, there was an almost unspoken affection between them when they would see each other in public. A passing touch here, a look in the eyes there; now here she was, looking as tempting a view as she did back then. “...b-but anyway.”

“Oh? Maybe you’d like to sweeten your luck with a pretty bunny girl?” She teased him, grinning as his cheeks darkened. “I wouldn’t let any other guy touch me here, but for you, well…maybe I could make an exception.”

She laughed as Featherweight fumbled with his camera for a moment, making the older mare wave a hand. “I’m just teasing, sweetie! Don’t wind yourself up so much,” she told him as he exhaled and pouted at her, hands on his hips, “how else are you gonna take such good shots of the casino? That’s what you’re here for, right?”

“Right. Yeah, not just to stare at the beautiful bunny lady in front of me.” He said, the offhand compliment making Derpy grin wider. “They wanted a proper show of the casino and things in action. And a few shots of the ladies, because let’s face it, pretty faces sell better for gambling than just basic machines and nice carpeting. I was told to meet a…uh, hang on, I wrote her name down,” he paused to fish into his pockets before pulling out a notepad he’d brought with him and opening it, “somepony named Golden Glaze?”

Derpy’s brow furrowed before she huffed. “Of course she gets to have time with you and I don’t.”

“You know her?”

“I do. She’s…well,” Derpy’s eyes both shifted to the right a little, one more than the other, “she’s not exactly a pretty pony beneath the pretty face. Sure, she looks really beautiful. Like, magazine cover beautiful.”

“Yeah?”

“But…well. I’ve seen her get a bit mean to other girls here. We’ve never really gotten to interact, but that might be because she doesn’t want me marring her looks.” Derpy’s grin weakened a little. “Lotta folks seem to think looking in two spots is a little bit off.”

“Well, they don’t know you like I do.” Feather asserted. “They might’ve put me with her, but I’m the guy in charge of photographs here. So I’m not gonna -”

“Oh, yoo-hoo! Mr. Photographer!”

The overly sweet voice made the hairs on the back of Featherweight’s neck stand up, and he turned around. The woman approaching was certainly hard to miss even in a flashy place like this. While Derpy was wearing a regular black colored bunny suit, the mare approaching had a white one instead. The suit itself was struggling against her figure some, her overly perky chest wobbling just a bit too much. An hourglass figure framed with a long blonde mane, and a smile that promised pleasure in plush red lips. To any other man, she’d be a walking wet dream. To Feather, with Derpy behind him, she just looked a little too…fake.

“That’d be me. Golden Glaze, I take it?” He asked.

“Well, aren’t you a sharp little fella?” Her southern drawl hung in the air as she came to a stop in front of him. She was taller than Derpy by a couple inches, though that might have stemmed from her heels. She leaned over to look down at him, inadvertently making her cleavage bounce a little before settling. The sheer heft she bore was enough to almost make her pop out of her top already. “I can’t wait to see what you can do. The boys upstairs figure you must be one clever pony to get picked for this job. Think you’re a big enough man?”

Feather tried not to bristle at the remarks on his height, remaining professional and simply holding a hand out. “I like to believe it’s my camera that does the talking for me. I’ll certainly do my best to showcase you and the casino plenty, Ms. Golden.”

“Heh. You know, I appreciate professional gentlemen. It’s when you’re alone that the real magic happens.” Golden’s white teeth gleamed as she grinned down at him, shaking his hand with hers. “Maybe I should come find you afterwards and see just what you’re made of.”

Feather felt the offer was like standing before a viper pit, but he had a helpful assist as Derpy rested a hand on his shoulder. “You know, Golden, he is a pretty busy guy. He might have more gigs after this one to do too.” she said. “Maybe we can show him around to where he’s needing to get some quality shots?”

“Oh, Ditzy, honey-”

“It’s Derpy.”

“-I am sure I can take very good care of Mr. Featherweight here. In fact, I bet by the time I’m done with him, he’ll want to come back to this here casino to see little ol’ me as soon as he can!” She declared proudly. “Why, I’m the best looking attraction in the whole building!”

“GOLDEN GLAAZE!”

The furious bellow of a stallion’s voice echoing across the casino’s loudspeakers made Feather and Derpy jump, while Golden just seemed to sigh in disappointment. “Well. That was fun while it lasted.” The country accent was completely gone from her tone, now replaced with a more refined Canterlot-esque tone. “A shame we didn’t get to have any fun. Perhaps next time, Mr. Featherweight.” She gave him a nod of her head before glancing at Derpy. “Dingy, do make sure to not damage too much of the place. I was fond of my job.”

“It’s still Derpy.”

If she did hear the correction, she didn’t bother to acknowledge it as she turned tail and booked it for the exit. It was a surprising feat, given she was in heels and still managing to outrun two burly security guards coming after her once they spotted her bouncing, fleeing figure. It was an amusing spectacle for some, while others had their cameras out to snap a shot of the escaping mare.

“Well. That’s a change of pace.” Feather commented. “Any idea why she’d suddenly take off like that?”

Derpy folded her arms over her hefty chest. “To be honest, I don’t know. The last time I saw anypony get chased out, it was a couple of troublemakers trying to rob one of the slot machine sets by rigging them. But they got busted.”

“Maybe she owed the casino money?”

“Oh, she owes us money alright,” came a more familiar southern accent from behind them. Both Derpy and Feather turned to find Applejack herself coming over to them, one hand on a cocked hip when she came to a stop. She was dressed in an honest to Luna business suit, but even business attire couldn’t make her get rid of her tanned brown hat. “Thought I recognized your name when I read over the paperwork for today, Feather. I’m awful sorry you almost got tangled up with that thief.”

“It’s ok, AJ. Feather hadn’t even gotten started yet.” Derpy replied for him with the stallion nodding in agreement. “What did she take?”

“She didn’t run off with no bank bag, that’s for sure. Apparently, Flim and Flam got a Celestia-danged golden moustache in their office made of actual solid gold. Worth it’s pounds in a year’s paycheck, I’d say. Somehow, that gal managed to get in, stuff it in her suit, and was gonna try to slip it out under our noses while playing at being lil miss southern belle.” AJ told them. “Now I’m sure we’ll find out where it is, because ain’t nopony gonna not see somethin’ as ridiculous as that. But now I’m out an employee, and I’m out a photography shoot.”

“Who said we’re out?” Feather replied, grinning as an idea came to him. AJ cocked an eyebrow at him before he looked to Derpy. AJ’s look followed suit, causing the cross-eyed mare to blink and look at both in the only fashion she could.

“Huh? What is it? Is there something on my face?”

Featherweight’s work had been cut out for him earlier, trying to think of how to work with the now criminalized Golden Glaze. Of course, that was something he knew he’d have to be ready for in his line of work; not every client or subject he’d be taking photos of would be jolly or happy or easy to work with. Some of them would probably be downright difficult, demanding. For a place like a casino, he expected some of the latter since anywhere that ran with a lot of money was usually followed by clouds of high ego.

Luckily for him, Derpy was much more of a happier participant.

“That’s great, Derpy, you’re doing wonderful!” Feather told her as the grey-coated mare beamed under his praise. They’d borrowed one of the reserved rooms for card playing, usually saved for private parties or even movie filming sets. Derpy, still in her bunny girl attire, was posed on top of the table with poker chips and a couple card decks scattered about. The mare herself was positioned on her knees, leaning back onto her heels with a carefully arranged royal flush between her legs on the table. It put emphasis on her legs, showing off her curves almost as much as the suit showed off her cleavage at the same time.

“Thank you, Feather! Oh, this one makes my legs tingle a bit!” She giggled out before sitting up a little, one arm placed deliberately under her chest to lift her impressive heft some while the other rested on the table for support. “Good thing I’m flexible!”

Feather tried to not think too hard about a flexible, almost naked Derpy atop him in such a similar pose. It really was an appealing thought that he was sure would stick around later when he would sorely need alone time. “And let’s try something with the poker chips next. How’s about…I have an idea, but we’ll have to have you hold very still. Ok Derpy?”

“Sure!”

A few moments later, Featherweight was snapping a couple of final shots. The pose in question had Derpy sitting more comfortably on the edge of the table, one leg crossed over the other. However, Featherweight’s camera was centered on her upper torso. With a careful balance that surprised even him, he and Derpy had constructed a small pyramid of betting bits placed over her cleavage, keeping Derpy’s face out of the shot save for her grinning expression. It impressed even him and would make for a creative pinup advertisement for the casino’s gambling crowd. Truth be told, he envied those chips just a little right then.

“Ok, Derpy, that should probably do for now. Whew!” He exhaled as he lowered the camera. The blonde pegasus plucked the chips off of her chest and laid them on the table. “That should be plenty of material for them to work with. And you looked absolutely stunning!”

“Awww, you big sweetheart. You’re just saying that!” Derpy replied, turning her head aside. “You tell all the bunny girls they look stunning.”

“I mean, a lot of them are pretty. But the only one that’s stunning is the one in front of me.”

Derpy blushed and smiled at him. “Do you flatter all the girls you photograph like this?”

Feather smiled back, albeit bashfully. “Would you believe me you’re the only woman of late who would let me photograph her?”

Derpy got up from the table. “No way! You’re kidding?”

“Nope. Turns out a lot of folks in Ponyville are either camera shy, too busy, or don’t think I’m legit. I guess I still have a ways to go.” Feather fidgeted with his camera a little, running a thumb over the top of the grip. “But, that’s why I’m here. Gotta show folks I’m a grown pony who means business.”

“I think you mean business. Or that you’re a good, nice business?” Derpy offered, getting closer to him, hands behind her back. “You’re definitely a grown pony. I think I would know.” He felt his face warm at her wink. “In fact…I got an idea!” She took his hand suddenly, making him jump a little before following her as she pulled him from the room out into the hallway. Glancing left and right, she tugged him along with her down the hallway before taking a right, then another left down a smaller hallway that had a dead end decorated with a simple, plastic looking green plant in a pot. Derpy checked the door before pulling him in.

“Derpy, what-” Feather started to say before the door closed behind him. A click of a lock assured him that the door wouldn’t be opened from the outside, leaving him and Derpy in a room he hadn’t expected to see. Three large, plush looking sofas encircled an elevated platform, where the lighting shone upwards towards the metal pole in the center and the ceiling past it. There was a refrigerator off to the side, no doubt for drinks for patrons. Two loudspeakers were perched in the far corners of the room, momentarily quiet.

“...I didn’t think they had something like this here.” He murmured. “Does AJ know?”

“Probably. One of those dirtier secrets she probably doesn’t mention at the family dinner table. I don’t tell Dinky I dress up as a rabbit girl in a casino; I just tell her I’m doing extra mail outside of Ponyville.” Derpy said softly from behind him. Featherweight paused as he felt her chest against the back of his head, while her arms encircled around his front. He stayed still as Derpy whispered in his ear. “...I’ve missed you, Feather.”

He brought one hand up and rested it on her forearm, his grip on her gentle. “I-I did too. I um…I didn’t do anything in public because I didn’t want to…you know, bother you. O-or make trouble.”

“It’s ok. It was smart to do that; some ponies here are still too conservative to imagine a young stud like you going for an older mare like me.”

“You’re not old!” He insisted, making her giggle before she moved down to kiss him on the cheek.

“I know I’m not. But seeing you focus on me so much earlier, all those photographs. I…I want you to keep looking at me. I want you to see me.” She told him. He looked up enough to see her watching him, one eye on him while the other was almost on him. “Sometimes, we get asked for some private fun. Golden Glaze did a lot of these, but I rarely ever get approached. Why don’t you take a seat over there, and I’ll show you the stuff a ‘grown pony’ can enjoy?”

He hardly needed a second to consider the invitation, settling onto one of the sofas closest to him while Derpy ascended onto the platform with ease using her wings. She looked over her shoulder to him, her back turned to him before she arched a leg around the pole and lifted herself up, swiveling with ease and turning about the pole before coming down to squat in front of Feather’s position. “Never thought the neighborhood mom could be a stripper, huh?”

“When did you learn how to pole dance?”

“There’s a lot of things a woman will do to keep food on the table. Some we talk about; some we keep quiet about.” Derpy told him as she dragged her fingers over her middle before toying with one of the suit flaps that kept her breasts decent. “I think I can put something like this to good use for you, Feather.”

With that, the mare tugged on her attire just enough to expose her chest, allowing her mounds to bounce freely as she twirled again. The grace she expressed up there was enthralling as it was erotic, Derpy moving fluidly from one position to the next as she spun about the pole. He never once took his eyes off of her, drinking up the sight of her as she held onto the pole to bend backwards, looking at him upside down before grinning and rising back up. The entire dance was impressive, a silent expression of eroticism that left the youth speechless by the time she came to a stop and kneeled on the stage in front of him.

“I meant it when I said I missed you, Feather,” Derpy declared as one of her hands came up to grope at her bare breast, an index finger gently toying with her nipple while the other hand held onto the pole for balance, “At first I thought I could keep it under control. I’d see you once in awhile, and it would bring back nice memories of that night. But then it kept coming back to me…and I wanted more.”

Featherweight only nodded silently, unwilling to speak and break her spell she had on him. He felt his hardened member pulse against his leg, but resisted the urge to adjust it just yet.

“I’d go home and find myself wanting you alone with me again…touching me…feeling me…pleasuring me…” She whispered to him, lowering her hand towards her groin. Only then did Featherweight realize there was a small zipper there, one her fingers were inching towards. “Do you have any idea how wet I’d get, thinking of having you fill-”

Whatever remained of her monologue was unfortunately cut off as a sudden crack from the stage, as well as a metal clinking of the pole, interrupted her. Derpy and Feather both had only a couple seconds before both immediately moved away from the stage, and just in time as a portion of the stage cracked and broke off, causing the stripper’s pole to come loose from it’s holdings and fall to the floor with a heavy clatter. Fortunately for them both, no further furniture took any damage, although it certainly left them quiet side by side until Derpy finally spoke.

“Celestia dammit!” She exclaimed, making Feather almost jump as the blonde mare stomped her foot against the floor. “So not fair!”

“It’s ok, Derpy, honestly. I’m just glad you aren’t hurt!”

“I know, just, I practiced that for the past few days, and not once did that stage give me any trouble! It was so perfect! And I would get to look cool and sexy, and…and then it just fell over!”

Featherweight took a moment to think of what to say, before wrapping an arm around the still semi-nude MILF’s waist. “Well, for one, I thought you looked very beautiful up there. And still are. If the opinion of a young, hormonal stallion counts for anything.”

Derpy pouted at the stage before looking at Featherweight. “Of course it does! I wanted to do this for you. And be Miss Sexy, and Cool. And Balanced.”

“Secondly, uh, well…I’m not as smooth as you, but…” Feather cleared his throat before glancing down at her naked bosom, “maybe we just need a different pole to dance on?”

“We could…try another room?”

Featherweight shook his head. “This pole is still clothed. And finds you very attractive. And has zero objection to you dancing clothed or naked on it.”

Derpy blinked one eye, then both eyes before comprehension dawned on her. “Oh. Oh! Oh you little smartass.” She laughed with a snort, making Featherweight smile as she relaxed a little. “You don’t have to be nice just for my sake.”

“I’m…actually being completely serious.” Feather said, his cheeks glowing as Derpy looked at him. “Genuinely.”

It took a moment for it to sink in for the older mare, but as her eyes narrowed and her lips cocked upwards into a grin, he felt himself twitch in his pants.

“You really liked my dancing that much?”

“It’s more I just like you, all that much. Anything involving you. And naked you is very very likable.”

Derpy giggled before using a hand to push on his chest and guiding him towards one of the plush loveseats nearby. “You suggested a different pole to dance on. But if I’m gonna do that, I’ll need a good warmup first.” She said. When Feather’s rump hit the cushion of the chair, Derpy was on him in an instant, placing herself in his lap to claim him for herself. Straddling him with ease, she had little trouble getting him to lean his head up as she kissed him, the contact igniting a hunger in both of them as she wrapped her arms around him to pull him closer.

For Featherweight, it was a fresh reminder of the bliss from New Years Eve, only now without the tinge of alcoholic courage to push him forward. She was welcome to his efforts as he embraced her around the middle, fingers brushing along the fur of her side before coming up near the slope of her breast. Derpy’s hands were hardly idle themselves, one toying with his hair to keep him close to her as their tongues danced together, the other resting on his chest.

She pulled back, panting a little for air as he did the same. Derpy only smiled at his lustful stare up at her form, having no objection to the way he admired all of her he could see so far. “They’re meant for more than just looking, you know.” She told him, giving a small shake of her chest that made her tits wobble before his eyes. The stallion hardly needed another invitation before he was upon them, pulling her closer towards him and latching onto a hardening nipple with his lips. She hissed in delight while grinding her front against his groin, squealing when he groped at the other breast to keep it occupied. “Oh yes, momma likes that. Keep playing with my tits, Feather.”

He obeyed, suckling harder at her nipple and toying with it using his teeth while she continued to playfully grind against him, careful to never pull away out of his reach. The smell of her perfume wafted up to his nose, fresh and intoxicating alongside the unique scent that was the MILF’s own. He was throbbing in his boxers now, begging to be let out for more pleasure but he couldn’t bring himself to let go of her. She was irresistible with the sounds she was making while he savored her breasts, swapping sides to give the other its fair share of love.

When he felt one of her hands reach for his at her waist, he slowed his efforts to look as she brought it around to her front. “Feather…I want you to feel me. Touch me.” She asked him, her fingers quick to tug her bunny suit to the side enough to expose herself fully behind it. His eyes widened; she had gone commando the whole time, as flushed darkened lips greeted his sight and made him come off of her breasts for a moment. His fingers brushed against her mound, cupping it with his palm as she guided him, the blonde mare biting her lip when she felt him rub ever so slowly against her. “P-please.”

“Well…only since you said please.” He teased. Before she could remark, he plunged an index finger right into her, making her words slur into a trembling moan as he stroked against her inner depths. “Wow. I’ve…never gotten to do this. You feel so wet. So warm inside.” He mumbled against her breast as he continued to work his finger back and forth.”

“Oh goddess. Keep doing that. Keep touching me. Y-you can use another-yyeeeesss!” She squealed as his middle finger joined the first, plunging into her and working together to rile her up. The wet sound of his digits moving in and out of her canal were overshadowed by her leaning closer and moaning in his ear, whimpering before whispering. “Finger me, Feather. Finger momma’s pussy. Oh, please, please, please!”

He obeyed without hesitation, goaded onwards by the lustful sounds she made as she seemed to clench around his fingers when he’d thrust in. With her holding onto him now and still straddling his lap, he was free to use his other hand to toy with her breasts again, tugging on her saliva-soaked nipple for further pleasure. It did the job as she cocked her head back in surprise before groaning deeply. The next thing he knew, she was burying her tongue into his mouth and kissing him heavily, humping into his fingers and trying to get him deeper into her.

From there, Featherweight found himself relishing testing this new means of pleasuring Derpy. Sometimes he’d wiggle his fingers inside of her, and she’d shiver in response. Then he’d spread his fingers apart, and worked them back and forth in short motions that had her gasping. Then he’d close them and push deep, being rewarded with a wetness that continued to coat his fingers and spread over his hand as she worked herself into a frenzy. By the time a third finger was added, she was completely incoherent and drenching his lap. He felt a tinge of pride in him to make her feel so good.

“Feather. Feather, ohfuck, ohfuck, do it. Faster. I’m close honey!” She pleaded. He did his best to work his three fingers in and out of her, keeping up the fast pace she begged for. His hand twitched suddenly, the labor catching up with him in the moment and making him adjust his hand to press against her more firmly. The poke of something back against his palm almost made him stop as Derpy’s breath hitched. “Ohfuckme!” She cried out.

He rubbed against it, as best he could in the circumstance. He’d use his thumb, but his dexterity wasn’t good enough to quite manipulate all his fingers in such a fashion. But it seemed to be just enough as after a few more strokes, Derpy’s body locked up and clung to him tightly, his face pressing into her chest as she trembled against his smaller frame. A fresh splurge of wet mare juice splashed against his hand and over it, leaving him to envision the mare’s pussy squirting from his actions.

Derpy had to take several deep breaths to get herself back under control again, and even then, her features remained flushed as she finally gazed down at him. There was something loving in her stare, needful. He didn’t speak as she brought his hand he’d used to pleasure her up and licked each digit clean of her juices, dutifully licking at each one until only her saliva remained. “Feather?”

“Yeah, Derpy?”

“Get that wonderful cock out. You’ve got me all stirred up. I can’t…I can’t wait anymore.” Derpy got off of him and stood up, wobbling a little as she worked to tug the rest of her costume down and off her body. The almost entirely naked mare, save for the fake bunny ears and her heels, watched with anticipation as he fumbled for his fly and undid it, tugging his pants down enough to let his cock finally be free. It leapt upwards once no more cloth contained it, coming down to his stomach with a firm slap as it twitched in anticipation.

“Oh yes…I’d love to suck him off. I really would,” Derpy whispered as she climbed into his lap, aligning him with her entrance and letting the tip rest against her soaked folds, “but I need it. I need it really bad, Feather.”

“I’m not gonna stop you. Whatever makes you happy, I’m down for.”

“Good boy. What would make momma Derpy happy is, oh,” she sighed as she started to sink down on his shaft, his tip penetrating her with ease, “is this cock, oh! Filling me…fuck!” She gasped out as she hilted him inside her, making Featherweight grab for both hand rests to try and keep himself still. The grey pegasus mare came to a stop for a moment, her hair falling about her eyes as she ducked her head before bringing her hands up to rest on his shoulders. “It’s right where it belongs, Feather. Do you know where that is?”

“I-Inside you?” He grunted out, feeling her spasm around him as he twitched.

“Inside this wet pussy. This cock is…ung! So perfect!” She exhaled out and rose up, pulling herself up to leave only a couple inches of his length inside her before coming back down. The slap of her butt against his lap was audible through her moaning, Derpy setting the pace of her riding him for the time being. Featherweight was so worked up from pleasuring Derpy and the entire experience so far that it was taking a great deal of work to not cum already. Her soaked marehood was an embrace around his cock no other experience could match, save for actions by Derpy herself.

“Fuck, Derpy.” He growled out as she continued to ride him, taking slow and steady strokes that made her chest bounce before his eyes. The blonde MILF merely replied by letting go of his shoulders, hooking her hands together behind her head and making her prominent chest bounce more provocatively for his viewing. Feather soaked up the view and relished the way she could be both absolutely intimate with him and undeniably raunchy.

“That’s the idea, big guy.” She replied, giggling before moaning as his hands came up to play with her tits once more. “You really like my big girls?”

“I love them. I…you’re the sexiest thing in my life, Derpy.” Feather had enough sense to mind his words; he didn’t want to overstep a line neither might be ready for yet, despite how much hormonal passion he felt right then. “There’s no woman like you.”

“Feather…” She whispered before bouncing faster, riding him harder and beginning to really work her hips up and down. The faster pace hammered away at his resistance, especially as he couldn’t get himself to look away from her face. Her whole focus was on him; one eye staring back while the other glanced at his cheek. Flushed in her cheeks and lips parted for lustful gasps of air to keep herself going as she took him again and again. It was too much to try and hold back for.

“Derpy!” Feather growled out, letting go of her chest to grab for her hips instead and buck upwards into her. The change caught the pegasus mare off guard, making her throw her head back and moan aloud as he took advantage of her shock. He needed it too bad, to get his release. It could only last for a few more thrusts, Derpy bouncing again to match in tandem, before he gave in and released his load. Feeling his seed suddenly splashing into her depths, the mare slammed herself down and stayed put, taking every throbbing pulse of his cock inside of her as more of his seed flooded out. He hadn’t tried to do anything for himself in at least a week, and the utter relief was as intoxicating as the mare before him.

By the time some sense came back to him, he realized that Derpy was pulling off of him. The cool air met his now semi-hard cock and shocked a bit of awareness back in him. “I-I lost control of myself. Oh shit, Derpy, I should’ve-”

He was cut off as Derpy held a finger to his lips, making him pause his apology while the blonde mare only smiled at him. “I wanted it. I still want it. And I’m gonna keep wanting it, Feather.” she told him, leaning in and kissing him tenderly. He returned it, watching her as she pulled back while bringing a hand down to caress his cock gently. “Do you know why?”

“Why?”

“I like feeling wanted. Feeling desired. Not as a hayburger on display, or how some men just see a nice body with messed up eyes. But wanted in a way that makes me feel like a real woman. Like…your woman.” She declared, looking up at him. His whole face burned from the affection that seemed to radiate off of her. The photographer was at a loss for words while Derpy sank down to her knees between his legs, taking his member and letting it rest against her cleavage before it was engulfed in it as she leaned forward.

“I know it might seem silly. But with you…I feel so much more like myself than I do alone.”

The bold declaration was punctuated by her working her tits up and down his length, massaging it gently and coaxing some leftover seed from it to spill onto her bosom as she titfucked him. Feather could only lay back and relish her efforts as she worked him up, soon having his cock poking out of her cleavage enough to let her lean down and lavish it with her tongue, making him moan as his still sensitive member throbbed from her efforts.

“Does it feel good between my tits, Feather?” She asked when she came up, grinning as her cross-eyed stare looked back at him. Derpy continued to pump his cock with her breasts, their grey mass enveloping him in warmth and reviving him with every passing second.

“It does. It…oh shit,” he cursed as she leaned back down to suck on his tip again, “I could never get tired of this. You’re too sexy for me, Derpy. Out of my league.”

“Even though you scored a home run already?” She teased, coming back up and licking her lips clean of his essence. Traces of black lipstick smudged at the corners of her lips and against his pinkish colored tip as evidence of where her lips had been. He was sure a little of it had to be smudged on his own lips by now too. Marked by her; the thought was invigorating to his spirit.

“I can always go for another swing.”

Derpy’s eyes gleamed with mischief as she stopped stroking his member and got up. Feather looked on as she approached the part of the stage that was still intact. Resting her hands on said stage, she cast a look over her shoulder at him before giving her round butt a shake. “Step up to the plate then, big guy.”

Feather moved quicker than any other pegasus he knew could’ve even thought to move, slapping his cock against her ass and letting it rest there for a moment as he took in the sight of Derpy’s rear pressing up around him. From this angle, he could better appreciate the plush softness she was packing, his hands latching onto each cheek and sinking into them with ease. She cooed from the grip he had and gave a little bounce with her rump, toying with his member with eager anticipation.

“Give it to me good, Feather. Give me all of it,” she taunted as he reared back and aligned himself with her again. It was an easy target to find, splashed with the white remnants of his cum still dripping down to her thigh from her waiting marehood. He didn’t spare another second, shoving himself straight in and evoking a cry from the pegasus mare as he held onto her to brace himself as well.

The different angle for them both brought a bevy of new sensations, especially for Featherweight as he was just tall enough to be even with Derpy. Pushing all the way in, he savored her lustful cries before her rump smacked against his groin, her tail batting left and right with eager energy. Feeling it brush against his middle, Feather took hold of her tail in his grip with one hand while the other stayed locked onto her rump. Her trembling cry gave away her enjoyment as much as feeling her tighten around him.

No words were needed for him to know she wanted more. He reared back, groaning as her tight and wet walls clung to every inch he had, before he slammed back in and smacked up against her rear. He tugged at her tail, and she cried out again before trying to work her hips back against him to get him to thrust again. Again he withdrew, and again he pushed in with a hunger that was entirely the blonde mare’s doing.

It took a few tries for him to figure out how to work his hips, aided by Derpy’s own movements. Before too long, he was rutting her with a lust that would’ve surprised him in a more clear mental state. But right here and now, it was only him and the woman he’d come to realize he yearned for. His sweat poured down his back as he bucked into her, plunging his cock again and again into her willing depths. The sticky and wet schlurp sounds of him churning his cum inside her marehood wove itself between her cries and the smack of their bodies meeting.

“Yes…yes! Oh, Feather! Oh my goddess!” Derpy cried out as she took everything he had to give. She seemed to be relishing his roughness as much as he was, the occasional yank of her tail only making her tighten up all the more around him. The endless display of her rear jiggling against his lap each time he thrust was a sight he dedicated to memory, something he could never have imagined seeing before this moment.

“Derpy…fuck!” He hissed as he felt her tighten around him much more than before, forcing him to slow his thrusting from sheer grip that she had around him. Only as he felt wetness splash against his groin and thighs did he realize he’d made her climax again, her pussy trying to milk him for his cum again. He pushed through it, evoking a babble of cries from Derpy as he pushed his body to the brink. His inexperience was catching up with him now, his stamina quickly starting to run dry.

“Feather! Cum in momma! Cum in me!” She begged him. He throbbed at the sound of her wish.

“A-are you…fuck, sure?”

“Yes! Please! I need it! I need it!”

Passion overtook logical worry, and Feather gave up on the rhythm they’d been using to hammer away at her marehood. His cock became like a blur, his balls bouncing against her rump in quick slaps of groin to ass while Derpy moaned all the while. He released her tail and took hold of her other ass cheek, before hilting a final time and draping himself over her back. He could feel every pulse of his cock as it fired off another salvo of seed into her depths, filling it once more with his cum. It seemed to echo throughout Derpy’s body, her curvaceous form giving a tremble every time he moved even only a little while still finishing inside her.

He rested his head against her back, nuzzling his cheek against the smooth muscle there as his climax tapered off before he withdrew finally. Without his member there to plug her, his seed began to fall out in small globs that stained the red carpet with dots of white. The bliss of orgasm was joined by the weariness his body felt from his efforts, leading him to turn and sit with his back against the stage beside Derpy. He closed his eyes, gasping for air as silence permeated the room beyond their breathing.

“Derpy…I-oof!” he gave out a gasp as the mare settled herself in his lap again, catching him off guard. He half worried she was going to try for a third round, something he believed he wasn’t ready at all for without a good break. Instead, he only found affection waiting as she kissed him deeply, getting a response from him to return it before she broke off to nuzzle the top of his head.

“You’re amazing, Feather. If you’re not careful, you’re gonna make this mare fall for you.”

“Yeah?”

“Yeah. And I’m a mare prone to breaking whole buildings when I fall, you know.” She joked through deep breaths before sighing in bliss.

“...well, there’s never a bad time for new renovations?”

She laughed, and he chuckled as well as they cuddled together there, basking in the afterglow of a moment spent as happy lovers. When he opened his eyes again, and surveyed the room, a thought occurred to him.

“You know…we’re gonna have to explain how a stage got broken while we were uh…’working’.” He noted.

“Oh, that’s easy. AJ had a backup disaster fund when she set up my contract. My reputation precedes me.”

Featherweight’s eyebrows raised. “Did she really?”

Derpy smiled. “I’ve kept costs low, as best one can. Breaking something here is covered.” She nodded at the stage and broken pole behind them. “Now, breaking my bed, that won’t be quite insured. But I think the benefit outweighs the cost.”

Feather’s cheeks glowed as Derpy wiggled her eyebrows at him before laughing again.

Author's Note