A Fair Game

by Michael Hudson

Rating: mature
Tags: My Little Pony: Friendship is Magic, Anthro, Romance, Applejack, Flim and Flam, Sex
Length: 2962

It might be fair, but Applejack still plans to make sure she wins.

Everyone knows how to play strip poker, right? You dress in as much as you can, play the cards, strip down, have a good time as you all wait to actually get to some skin. That's how you're supposed to play.

Someone needs to tell Applejack that.

Artist is Emperpep

Come support me with either my original works or by joining my fairly new streaming channel!

Published 2019-06-14 19:00:02 UTC
Last updated 2019-06-14 19:00:02 UTC

On a Special Night

Author's Note

Author’s Note: I actually had a little bit of silliness here. While I didn’t deal the actual cards, I chose who won each round by roll of the dice and let that help guide the story. I’ll even include everyone’s rolls in a spoilers here.

Applejack 4 4 18 3 6 11 3 12 2

Flim 3 6 4 4 5 1 10 10 20

On a Special Night

Flim swallowed nervously as he walked into the barn. It had been a… trying few years as he worked on finally getting to this sort of point with Applejack. The resort had been the first step, an honest to goodness business that wasn’t just a scam that she could be proud of and that could help fund other ventures. Then after a pretty minor setback honestly, Flam had finally been convinced to put the schemes mostly behind them and let them get on the right track, especially for his brother’s heart.

So, over the next few years they had come to work on more and more legitimate businesses. They weren’t perfect, mind you, sometimes not even without them realizing it. After all, he thought styrofoam was a perfectly solid storage material! Good thing Celestia could send it to the sun instead of it staying in the landfill forever. That wasn’t the point though. The point was that a year ago they had done so well that when Applejack magically stumbled upon their business again, all she’d had to say was good job.

That was his chance. That was his chance to ask the mare of his dreams out. To finally tell the kind, honest, strong mare of his dreams what he had always wanted. After all, he was somewhat pragmatic. He knew you needed a product that at least appeared to be worth something, even if her critical gaze had often made him feel worthless and thus in need of change, so he had waited. Kept his feelings hidden. Bided his time.

And, somehow, she still said yes. Even after what felt like a decade of failures and screw ups in front of her, she actually gave him a chance, just as she was tonight. Though, to be fair, tonight was her plan. Her very weird, awkward plan it felt like to him, but her plan anyways. He smiled at her, giving her a small, nervous wave before throwing a deck of cards into the air. They threatened to fall into a boring game of Fifty Two Pick Up, but instead stayed in a floating array above him as he made his way forward. “I brought us a deck, and to prove I won’t shuffle it wrong, or it’s not loaded, I thought we’d just pick our cards from the deck.”

Applejack didn’t even glance to double check that the cards were in fact all facedown as she giggled a little. Once Flim had stopped being a cheat, she had come to find his little bits of showmanship endearing. It was something she’d never been good at but just a year of advice from him and Sweet Apple had seen an almost thirty percent increase in sales. It was… breathtaking honestly. Watching him at advertising and the sort of passion he had, even if he needed a reminder of morality for the customer’s sake, was what had always caused a fuzziness in her. Now if only he wasn’t ten years older than herself and so a little more stuck in his ways, but they were working on that together now.

What she did do with the deck of cards was casually point at one, which brought the one there to gently swing its way down towards her. “What, not gonna shoot it straight down? Or make it explode into sparkles and appear out of nowhere?”

Flim put a hand on his chest, pretending to pale at the accusation. “How dare you? I’m on a s-simple date night with my marefriend and you would threaten me that I would try to fancy it up some-” before he smirked and the four cards around that first one did indeed shoot down towards her, sparkles leaving a trail of lights behind them as the slowed down just in time to gently reveal themselves to her.

Applejack smiled more as she put her cards on the table before stretching back and letting Flim take in everything she was wearing. Everything that… wasn’t enough to make the older businessman calm down. After all, he knew the plan tonight. Knew how Applejack wanted to see their first time together be. To make a game out of it, a game she didn’t look prepared to win since, from where he sat, well…

She wore next to nothing! It was normally something he thought absolutely amazing, but tonight was terrifying. She wore a button up short that was instead tied off just under her large, heaving bosom which let him take in the cute freckles that dotted the sides of her chest as they jostled and jiggled in their jail. Her ass was covered by a pair of shorts that left her cutie mark in full view, let alone her large, farm grown thighs that could, and had in the past, crush his head between them. Tonight was the first time he thought that might happen pleasantly though, something that scared him in a whole new way. She surely had to be wearing undergarments under them though. After all, she was still a respectable, old fashioned mare and not some radical like her friend Rainbow Dash… right?

He on the other hand kept his perfectly toned, lanky body covered in a button up shirt, tie, long pants, shoes… Was she wearing- She had to be. He just forgot to check. The big point was that he was fully dressed. He even wore a vest over his shirt just to make sure he had another layer, though he also thought it made him look better. At least it meant he was more likely to win? Oh, that didn’t feel good.

Applejack extended a hand towards him, gripping one of his gently from across the small table they were sitting at as she whispered, “It’s okay. I like that you’re so nervous, and if this ever gets to be too much, just let me know. Okay?”

Flim smiled nervously back as he laced his fingers back into hers and squeezed hard. “If you’re… If you’re certain you want to do this, then that’s what I want to try too. Now, w-what are the rules?”

Applejack nodded before tapping on her cards in front of her. “Five card stud, and everytime you lose, I get to see more of my stud. Everytime I lose though, well,” She smirked and pulled at her top, threatening to break the loose knot that already strained against her bust and… and was that her areola? No, no it couldn’t have been. She. Was. Dressed. She had to be.

And so the first hand was dealt. Both absolute garbage, but Applejack’s seven beat his three. So, off came Flim’s hat. The next round was… absolutely just as exciting, but just in reverse. At least Flim got an ace high so that was something but he turned his attention back to Applejack as he sweated nervously. What would she take off? Would shoes count as one, or two? What was she wearing that he couldn’t see?

Much to his relief… That felt wrong while his marefriend, in her full beauty, sat here waiting to strip for him. She took off her shoes first, though she paused and held one up for a moment as she said, “These count as one,” and then chucked them to the side. He nodded in agreement, even if he could have really used them counting as two. Not for his sake but… Well, he didn’t need to dwell on it anymore.

The next hand felt like a waste as a high six got beat by a fullhouse. Still, it meant Flim’s tie came off next, something he was all too happy to do as he’d slowly been tightening it more and more as the night had continued on. Now it wouldn’t threaten to choke him when she lost next. It was just in time too as a literal swap of their first hands came down next. Applejack blinked a few times as she took in the fact that their highs were the same as then before asking, “Are you sure you shuffled these properly?”

Flim swallowed hard as he shrugged. “Honestly, maybe too well? The magic is supposed to just hold them up there, I swear.”

“Oh, I believe you. I just thought that this would come with at least a pair like they are.” Before she nonchalantly pulled on the knot over her chest and let the two sides fall away as it broke. It was… breathtaking for Flim who felt himself immediately stiffen under the table as he bit into his cheek. They were so large, ripe, firm, and perfect. The dark brown areolas in the middle were stiff from the cool, evening breeze and teased him as they swayed a little with Applejack’s movements. The fabric didn’t help as it in fact stayed on her body, falling gently against the sides of her chest as she continued to smile at him, doing nothing more to accentuate them, which somehow was exactly the right call. At least, to Flim as some of the cards above them fell back to the table.

“Um, uh, sorry about that.” He began collecting them back up, trying to keep his eyes down as he brought all of the cards back into the deck, just to start with a fresh, clean slate. Now his own method of dealing though bit him in rump as he had to look back up to see where she pointed to. Not only that, but now Applejack wasn’t shy about making sure to bring his attention back up to… them as the two fingers she used to point then dragged themselves along one of her nipples as she brought the arm back to her side. They dragged on the small nub, pulling at the nub before letting it go to bounce and jostle as it tried to get back to a natural resting position.

Flim’s head was on fire by now and he thanked Celestia when he saw the cards and realized that he had indeed lost again. It was close, as it had been for most of the game, and at least slightly better with twin face cards, but Applejack’s ten after her queen meant that she still took the win, which let him casually take off his vest.

To which she leaned in to take it in. He didn’t even consider the fact that he should take the fact that she took even his awkward, failure of a strip show as something to enjoy, but instead thought it might be more of her attempt to light him on fire through sheer embarrassment and nerves.

That wasn’t true though as his next hand having a high of six while she had a pair really brought the pain as she raised her arms in triumph to one of them getting just a regular pair. This sent both of her breasts, and he would swear on purpose, bouncing up for him to take in. That wasn’t the best part though, even as her nipples tried to point to the sky from how hard she had smacked them. No, that came when they came down and the fat, firm flesh finally gave to the force of gravity, jiggling and flattening slightly as they hit her ribs, before they finally came back up, bouncing like a pair of heavy balls for another moment or two as Flim’s head short circuited for the moment.

To which Applejack only smiled, even as she raised a hand to nurse one of her breasts from how hard she had hit the poor mound, and teased, “Going to take something off now?”

He nodded absentmindedly, throwing his shoes away now as he cleared his throat and tried to calm down. This was what he was here for though, right?

The next set of cards came down and this time it was his chance to get a pair while she got junk, something she seemed all too happy about as she stood up. Now she allowed her shirt to fall from her shoulders casually, the red, checkered cloth lazily falling to the ground with a mere shrug of her shoulders. Flim thought she might have, thankfully, cheated, but she didn’t have any intention to do so. Not as her thumbs hooked into the sides of her shorts now.

She turned away, keeping an eye on him for another moment as she began to pull down. Her large, muscular rump dragged against the fabric, resisting it as Applejack herself had to grunt in order to get it to come away at all, forcing her to abandon her sultry look for more leverage and bending over. Not that that did anything to harm the sex appeal of the movement. It just helped Flim not think about how close he was to being where those shorts were in another few moments. This fact became all the more clear as her pussy, ripe and wet, came into view for him to stare at until finally the shorts got past the middle of her thigh and Applejack came crashing down from the force of her own pulls. “Applejack!”

“I’m okay! I just don’t,unf,” she kicked the rogue shorts away, mad at their betrayal as they smacked against a wall, “wear those very often so I forgot how stupidly hard they were to take off.”

And for a moment, Flim felt like things were right. Felt like this was what he wanted out of the night, a feeling that died when Applejack sat back up, her breasts right back into view as she tried to give him a sultry look over her cards. “Well, are you going to deal the next set?”

Flim mumbled an agreement under his breath, slowly forming what could possibly be a plan, but it was almost as scary as what Applejack had in mind for tonight. What if she didn’t like it? What if she needed more? He wasn’t exactly telling her no, but… He was thankful to see the cards come up against him so he could take off his over shirt, if not just to breathe better.

But then the final hand came down. Absolute junk versus a four of a kind of kings. A four of a kind of kings for Flim…

Applejack crawled, crawled over the table to him, smiling as she said, “You should know the hat stays on, honey, so tell me, how are we doing this?”

Flim looked up at her. His cock cried out for something. Literally anything. To let this continue where it wanted and to tell anything else to just fuck off. Looking into those beautiful, perfect, green eyes though… He raised a hand, cupping her cheek and whispered, “After dinner, in a nice room, with you wearing whatever you want instead of,” he paused to nod his head towards where the pair of shorts had fallen, “that.”

Applejack blinked a few times before whispering back, tears at the edges of her eyes as she asked, “Did I do something wrong? I wanted to make sure you were in the mood, but…”

Flim bit into his cheek as he considered the salesman’s way to put it. How to make a good spin on a bad trait but… No. He wasn’t about to be that dumb. He needed to be honest here, and honest was what he was going to be. “I’m in the mood. I would be in the mood if I was being attacked by Timberwolves and you shook your butt just a little. This though,” he said as he knocked on the table, “Isn’t me. Isn’t… us. At least not what I think of when I think of us and with how long it has been since I last… Okay, maybe that’s too honest.”

Applejack slipped her arms around his shoulders, climbing off of the table as her chest pressed against his almost as eagerly as her own lips did against his dry pair. The two gently fell to the ground in the embrace, but Flim wouldn’t reach any lower than the small of her back. Wouldn’t tempt himself further to go back on his word. On his decision on all of this.

Applejack pulled away, using one arm to wipe at her eyes as she mumbled, “I shouldn’ta listened to Rarity ‘bout this.” She then took a deep breath in and smiled at him. “I… I like your idea. I like it more than this. I just… I guess I’m used to listening to my friends talk about how after a month they are slipping into bed and… And I was afraid I was doing something wrong.”

Flim squeezed her tight, smiling as he whispered into her ear, “Applejack, there’s almost nothing you could do to make me go away. This I can promise you.”

“Careful, colt, that sounds almost like a proposal.”

And Flim could only smile as their next date night went exactly as he had pitched it, except that he finally brought the small box he had bought a year ago out of his luggage and felt his heart skip a beat when he said yes. It had been a long game, but it was all too worth it playing by her rules if it meant getting the princess at the end.