Poker Night at Diamond Tiara's

by Not A Pony

Rating: mature
Tags: Rumble, Sex, Diamond Tiara, Slice of Life, My Little Pony: Friendship is Magic, Cutie Mark Crusaders, Pipsqueak
Length: 5870

Diamond Tiara holds a poker night every other week, where things inevitably take a more than mildly adult twist.

Every other week, after Ponyville Community College classes are over, Diamond Tiara gathers a few friends at her appartment for poker night.

Inevitably, after a few drinks, things turn risqué. When the ante inevitably cranks up into betting more than just bits, stuff gets outright explicit.

A story of friendship, pleasure, and exploring one's boundaries.

Unapologetic cheap clop, aged up. All fictional sapient ponies involved are of legal age for drinking and appearing in erotic fanfiction.

Specific gender pairings and fetishes will be outlined in chapter headers. Should remain relatively vanilla. Straight, gay, and bisexual acts may be involved.

(My first attempt at clop to actually pan out. Updates will be highly irregular, if at all present. I'll do my best.)

Published 2017-06-11 17:50:10 UTC
Last updated 2017-06-11 17:50:10 UTC

Pipsqueak's All-In

Author's Note

M/F, some F/F, implied M/M.

Male on female anal OR female on male pegging.

Pip does Diamond Tiara in the butt.

Pipsqueak's All-In

Pipsqueak swallowed nervously as he knocked on Diamond Tiara’s appartment door.

He wasn’t exactly a virgin, having shared a bed with a mare or two. He’d also had a little experimentation with fellow stallions, thought had had mostly been limited to shared hoofjobs and one regrettable attempt at blowing Rumble. But if what the pegasus had told him was true, Diamond’s poker nights were something else entirely.

Still, it was nice to see the old crew again, even if not all of them had been able to make it.

He had to admit, looking at the brightly lit hallway, this was a very nice place for a first appartment. Diamond’s part-time job running the jewelry counter at Barnyard Bargains likely wasn’t her only source of income.

”Pip! You made it!” Sweetie Belle was the one to open the door and invite him in. Even though he’d grown some over the last few years, she still dwarfed him. Judging by the sight of Scootaloo and Rumble reclining on a couch across the room, he was still the proverbial runt of the bunch.

”Hey Sweetie! Hey everyone!” Pip greeted as he walked in, taking in the sight of Diamond’s appartment. He spotted the hostess in her kitchen, popping open the cap of a wine cooler. ”Nice place, Diamond!”

The entrance led into a large open room; at one end, the kitchen where Diamond Tiara stood, all of chrome and marble. An open-floored dining room and living room stretched out from there, capped at the far end by a broad picture window whose curtains were drawn conspicuously closed. The place was nigh immaculate, aside from a hoofful of empty bottles on the counter.

Diamond’s elaborate bedroom, complete with her queen-sized bed, and the only somewhat more modest guest room opened out into the dining room while the jacuzzi-equipped bathroom stood nearer the entrance, its door ajar.

The walls displayed proud tones of wine red and rich chocolate, and a few expensive-looking landscape paintings gave the room some life. The fireplace crackled peacefully in a corner, its mantle adorned with a lavish portrait of Pip’s prideful hostess.

“Well, well, well,” Diamond Tiara smirked as she approached. “The guest of honor is here.”

Before Pip could react, she’d draped herself over his back. “Don’t be shy. I won’t bite. Unless you’re into that; then we’ll have to see.”

She smelled of lavender perfume, and a little bit of strawberry wine cooler. Quite the pleasant edge, all things considered.

“Blimey, Di!” Pipsqueak laughed nervously at the attention. “Rumble told me we were supposed to play poker and the shagging would happen from there. You could at least give me a chance to close the door.”

“Yeah, Diamond, we're all here for the same thing; don't hog him all to yourself.” Scootaloo laughed as she hopped off the velvet sofa and dashed over to help Pip get Diamond out of his personal space.

“Fine, fine.” Diamond pouted unconvincingly. “What can I get you, Pip?”

“Got any gin?” He asked.

“Ha!” Rumble laughed. “Called it!”

Before long, the five of them sat around the kitchen table, cards in their hooves and drinks all around. Pip took a sip of his gin and tonic, and eyed the board. Appleloosa Hold ‘Em rules dictated five cards be laid in the middle over progressive rounds of betting, while each player held two private cards of their own. The strongest hoof of five cards took the round and the bets. Typically, the deck ran from two to ten, capped out by the Noble, the Prince, the Princess, and the Ace.

Here, Pipsqueak wasn’t holding much. With two fours, a five, a seven, and a Prince sitting in the middle, his own Noble and Princess weren’t particularly inspiring. He opted to abandon his bits and fold out of the round.

In the end Sweetie Belle took the pot, bringing herself up to sixty seven bits. Each of the players had initially brought fifty bits to the table.

A few rounds went on, and Pip thankfully managed to regain his lead after a lucky flush.

A few glasses went on, beer, wine cooler, and then increasingly stronger stuff, though still nothing beyond a pleasant buzz for everyone involved.

Perhaps through luck, perhaps through skill, bits were slowly but surely migrating to Diamond’s side.

Then, after Pip folded out of another round, bidding goodbye to six of his coins, Rumble and Scootaloo stood face to face, the only two remaining in the active round.

Three fives, an eight, and a Princess were aligned at the middle of the table while the two pegasi looked eachother in the eye.

Rumble smiled. “Twenty bits.” This wasn’t an uncomfortable bet for him, who still had a respectable forty-four bits to his name.

Scootaloo eyed her measly twenty six, the result of a few reckless bets. She smirked playfully. “... how about I up the ante?”

“Oh?” Rumble asked, his ears perking up. Pipsqueak looked at Scootaloo in confusion, and noted he seemed to be the only one at the table unclear on this strange turn of events.

“Ten bits. And a wingjob.”

Pipsqueak blushed at the thought as his eyes widened. So THAT was how that worked. That kind of fun would take some getting used to, but the tingling in his crotch assured him he wasn’t entirely opposed to this.

“Make it a blowjob, and you’ve got a bet,” Rumble smirked.

... were they going to do that right here in the open?

Pip caught Diamond Tiara looking at him. “It’s not too late to chicken out if you’re not up to the challenge, Pip. I get it if you’re not comfortable watching your friends fuck.” Diamond Tiara allowed the last word to flow off her lower lip like a lost drop of wine.

“Ooooooor... Maybe you’re just worried your ‘little Pip’ won’t measure up?”

Pip blushed furiously at the insinuation. Did he want to chicken out now? Nah. He just needed... some time to get used to this.

“Don’t listen to her,” Scootaloo said. “She’s just trying to get in your head.” Then, she turned her attention back to Rumble. “Fine, you’re on.”

With a smirk, Rumble tossed his two cards onto the table, revealing two Princesses, enough to bring him up to a triple.

“You wanna do this now, or after the game?” he laughed. If Pip knew Rumble as well as he did, the pegasus was probably already peeking out of his sheath under the table. His full wingspan on display certainly gave it away.

“Aw, nuts!” Scoots cursed. “All I’ve got is this seven.”

With all eyes on her, her expression turned. “Oh, yeah, and this seven. Four of a kind, Rumble. Read ‘em and weep!”

Rumble’s jaw dropped, and with it, his erection. “Oh, you tease! I’ll have your rump for that one!”

“You’ll have to win it first!” Scootaloo mocked, unashamed of her wings standing at full mast. “Or maybe I should let Pip here have a go, for a change.”

What did I bloody get myself into!?

The next round was dealt while Pipsqueak fetched himself a beer from the fridge.

He came back to Sweetie Belle triumphantly raking in her bits.

“Aw man!” Scootaloo exclaimed. “I thought for sure I had you!”

“Don’t be a sore loser, Scoots!” Rumble teased. “She got you fair and square.”

“Yeah! And I’ve been waiting for release all night, too.” Sweetie smirked, as she rose from her cushion. “Now be a good friend and pay up, would you?” She took a few steps towards the living room, and playfully wiggled her butt, before slowly and tantalizingly lifting her tail up, baring it all to the assembled crowd.

Rumble whistled an enthusiastic catcall. Pipsqueak couldn't help but stare incredulously.

“Fiiiiiiiine,” Scootaloo groaned, standing up in turn and following Sweetie to the living room.

“... just what exactly did I miss?” Pipsqueak asked Diamond Tiara, nodding in the direction of the two teenage fillies headed for the sofa.

“Sweetie got Scoots with an ace kicker. The pot was thirty bits and the loser getting the winner off orally.”

“... blimey.” Pipsqueak nodded. This was the real deal. Should he watch? Could he watch?

... Rumble was certainly watching as Sweetie, spread eagle, beckoned Scootaloo over. The pegasus tried to appear annoyed, but her own flagging tail and proudly presented nethers made that a frivolous effort at best.

“Eyes on the prize, boys,” Diamond Tiara called out, eyeing the two colts with a predatory smile. “We’re not stopping just for them.”

The game moved on without the two fillies, with the betting sometimes interrupted by a particularly enthusiastic groan or whinny from Sweetie.

It was a miracle, Pip noted, that he wasn’t completely hard yet. The evening was full of surprises.

Still, the game was drawing to an end. Diamond held seventy bits. Rumble held twenty two. Pipsqueak, less experienced, was down to nineteen.

Pip peeked at his two private cards. The others did the same.

Three cards were distributed onto the table. A Noble, a ten, and a four.

Diamond immediately spoke up. “All in.”

She pushed all of her bits into the middle of the table. If Pip hoped to win anything, he’d have to risk it all.

“Nope,” Rumble shrugged.

Pip peeked at his cards again, hesitantly.

“If you want to win, Pip, you’re not going to catch up with just the bits you have,” Diamond Tiara said, pointing at Pip’s diminutive stack of coins. “... if you know what I mean, and I think you do. What do you say we make this... interesting?”

Rumble laughed. “Here it comes, Pip. We’ve all been there.”

Diamond Tiara got up from the table and left for her room. “Wait here.”

She returned a moment later holding a most peculiar object in her mouth.

“Is that...?” Pipsqueak took the sight in with great confusion. He’d heard of strap-ons before, and this one looked to be some kind of luxury model. This was no humble cock; it would have been more than respectable on a colt Rumble’s size, nevermind Pip’s own smaller stature. The thick straps for it were marked on one side with a series of five peculiar notches, with a single heart on the far end of the row. “... Two questions, Di: What are you planning to do with this, and what’s with the notches?”

“Why, my dear little Trottinghammer,” Diamond answered sweetly, “See how there’s five notches here?” Diamond Tiara waited for Pip to nod, then pointed at Rumble. “One.”

Pip looked at Rumble, who shrugged. “... you win some, you lose some.”

Next, she pointed across the room at Sweetie Belle, who had her hind legs clamped around Scootaloo’s head and moaned frantically. “Two.”

Her hoof traveled down to point at Scootaloo’s exposed rear end. “Three.”

“Four and five aren’t here, but Apple Bloom took it like a boss, and you better believe I had my way with Featherweight.”

Then, with a smirk, she gazed back at Pipsqueak. “... and when you lose, that’ll make six.”

Pipsqueak gulped audibly. “... and the heart?”

“Silver Spoon’s special.” Diamond Tiara smiled. Of course.

Pipsqueak paused for a moment, his mind overloaded by Sweetie Belle’s orgasm exploding in the background and the overwhelming thought of what exactly Diamond was planning to do. “Bollocks... So... What are you proposing exactly?”

“Simple. If you lose, my little Pip, I get to lay you on my bed and rut you like a filly.”

“... and if I win?” Pipsqueak questioned.

Diamond Tiara scoffed. “... what, seventy bits isn’t enough of a bet? Are you scared for your little spotted butt?”

Pipsqueak was getting more than incensed. “All I’m saying, Diamond, is that if I’m going to put my tush on the line, I’m expecting you to put up a little more risk. Look at this place,” Pipsqueak waved around the room. "This is piddly money to you, and I know it."

Diamond’s eyes widened at his outburst, but she recovered gracefully into another one of her so-irritating smirks.

Fine. You want to play like that, Pipsy, then you’re on. At his size, I’ll be lucky if I feel whatever he’s packing.

“Very well, then.” Diamond Tiara shrugged. “I’ll play. If you win, you get to rut me...” She paused for dramatic effect. “In the ass.”

Rumble nearly choked on his beer. “Diamond, I don’t think you want to do this. You don’t know-”

“Oh, hush up and go join Squeaks and the chicken over there. I’m sure they could use some cock right about now. Let me have my fun here!” Diamond snapped.

Pipsqueak eyed one then the other, still in shock from Diamond's stakes. His ass against Diamond’s... was that a risk he wanted to take? That’d sure be a conquest for his little black book, but on the other end...

Rumble stammered for a moment. “... I’m serious, Diamond, you don't know what you're-”

Diamond slammed her hoof on the table. “Quiet.”

“Suit yourself.” Rumble shrugged. He stepped over to Pipsqueak and whispered to the colt: “Think carefully about what you want to do. If you go for it, have fun either way. She knows how to handle that thing.”

Rumble placed his hoof on the deck, ready to deal, and looked at Pipsqueak. “So, what’ll it be, Pip?”

Pipsqueak gulped one more time, and studied the cards again. Noble, ten, four. Two more cards to deal, but there was no turning back after he agreed

Well, he reasoned. He’d come to try things out. This was his chance.

“You’re on. I’m all-in.”

“... you have no idea how all-in you are,” Diamond boasted, slamming down her cards. Two tens, making three with the table cards.

“... blimey.” Pip sighed, revealing a pair of aces.

“Alright, Rumble,” Diamond Tiara grinned, pulling the toy closer to herself. “Deal his fate in.”

Out came a two.

Pipsqueak slumped. Maybe this wouldn’t be so bad. He’d been idly wondering out that would feel. Might as well find out with a bombshell like Diamond.

Diamond Tiara stood up from her cushion, and began to step into the straps. “Help me get into this thing, would you, Rumble?”

“Still one card to go, Diamond.” Rumble chided.

“Fine. Deal it and then go make sure Scootaloo doesn’t walk home straight. I’ve got a new boy to break in.”

All watched with trepidation as Rumble slowly peeled a card off of the deck and turned it over.

Ace.

Pipsqueak hit jackpot.

Diamond’s jaw hit the floor.

Silence flowed over the room; Sweetie and Scootaloo were basking in the afterglow of their fun, Pipsqueak and Diamond Tiara were speechless for entirely different reason, and Rumble simply savored the moment.

“HA!” Rumble erupted. “Scoots! Sweets! You gotta see this!”

Scoots all but flew over, her chin not entirely clear of Sweetie’s juices. Sweetie stumbled over on wobbly legs.

“Pip BEAT Diamond?!” they both questioned, in disbelief.

“... he did.” Diamond sulked.

“... what did he win?” Sweetie Belle whispered to Rumble, having noted the strap-on.

“... Di’s ass.” Rumble nodded.

“... well holy shit.” Scootaloo couldn’t help but say.

Pipsqueak sat motionless, helpless to process exactly what had just transpired. He’d already grieved his anal virginity, but here he was: the winner due to collect his spoils.

Diamond Tiara collected herself much like a tearful museum curator collected the fragments of a century-old urn.

“Ah, well. It’s not like a colt your size has anything particularly big, right?” Diamond shrugged, seeking refuge in her old hostility. “C’mon, stand up for and let’s see your Little Pip.”

This time, Rumble was the one who grinned, playfully jabbing Pipsqueak on the shoulder. “... alright, bro. Show her.”

Pipsqueak shook off his daze. All eyes were on him. He was still a little uneasy on letting everyone see what he was packing, but at this point, what was the harm? He’d just seen more than he’d ever thought he would of Sweetie Belle and Scootaloo, and Rumble’s respectable if average erection was on full display.

Pipsqueak stood from the cushion, and allowed his member to fly free.

Diamond Tiara’s jaw hit the floor a second time. Her eyes grew to the size of dinner plates.

“... Luna’s full moon, Pip!” Sweetie Belle exclaimed.

“... how in Tartarus were you hiding that monster?” Scootaloo stammered. “Hubba hubba!”

Pipsqueak, as he’d known all along, was huge. His member would have been impressive on a stallion of Rumble’s size, but on his own, smaller, body, it looked almost unbelievably large.

Diamond stared incredulously, still agape. Finally, she snapped and lunged at Rumble, planting a hoof on his chest as she apostrophed him. “You! Why didn’t you warn me? You have to had seen him hard at some point, right? You share a locker room in college! You guys have been friends for years! I know for a FACT he’s tried to blow you before!”

“Hey, whoa, don’t talk to me like that, Di." Rumble stepped back with perfect composure. "I tried to warn you and you cut me off. Twice.”

“C’mon, Diamond,” Sweetie Belle cut in, putting herself between Diamond and Rumble. “Fair game is fair game, you did make the bet.”

“It’s alright,” Pipsqueak said as he approached Diamond, winching as she flinched away from him. “You don’t have to do it if you don’t want to. I’m sorry I didn’t warn you ahead of time, I was kind of shy about it all.”

“Oh heck no!” Diamond fired back. “Look, I’ll admit it. I took the bet because I thought you’d be super tiny in the sheath, and that even if I lost, I’d barely feel anything. That was pretty selfish of me.” Once more, she stepped into Pipsqueak’s personal space and defiantly draped herself over his back. This time, the contact was far more welcome.

“I know I can be a bit selfish, and that I’m not always the most graceful loser, but if there is one thing Diamond Tiara is not, it’s a quitter!”

Finding Pip too stunned to move, Diamond ran her muzzle through his mane and pecked his cheek. “The others will tell you: I love that strap-on, and I love to make colts squirm when I fuck them in the ass with it. Featherweight will never admit it, but at this point I think he throws bets on purpose just to get the business end of that thing. I also love to get other fillies to service me, and I get a thrill out of seeing bets like Sweetie’s earlier pay off.”

“What you provide, though, is something new. Something I’ve been looking for: You’re a challenge.” Diamond Tiara hopped off of his back and laid on the sitting cushion she’d been occupying, ignoring the wet stain of her arousal that had been gradually accumulating as they played. Stomach down, ass up, tail high. Diamond Tiara beckoned Pip over. “C’mon, Pip. Show me what you've got. Let’s see if I can take it all.”

Pip approached, and gave Diamond’s rump a playful smack. “I’m rightly chuffed you’re up to it, Di, but I think we’re going to need a bit of prep if you really wanna try. I hope you have some lube around here.”

“On it.” Sweetie said. “I really wanna see this.”

Rumble laid on another one of the cushions, treating himself to an eyeful of Diamond’s nethers. “I sure hope you know how lucky you are, Pips. I’ve been trying to get at her ass for weeks.”

Scootaloo unceremoniously laid herself on top of him, laying her head on his shoulder. “What? I’m not good enough for you now?” she teased.

“Here, Pip.” Sweetie called out as she trotted back out of Diamond’s bathroom, tossing him a tube of clear gel.

“Thanks, luv,” Pip caught it and smiled back before turning his attention back to Diamond. He squirted some of the lubricant onto his hoof and, with both pegasi and the unicorn watching attentively, began applying it to her’s hole with perhaps a bit more pressure that was necessary.

“Oh, jeez. That’s cold!” Diamond shivered at the touch, burying her face in the cushion. “Keep rubbing like that and I’ll come all over before you even mount me!”

“That true, luv?” Pip smirked. “And if I do... this?”

Pip leaned forward and planted a series of kisses from her right buttock down to her nethers, flicking his tongue against her clit for good measure.

Diamond’s defiant demeanor melted away as Pip got to work on her with far more skill than she’d expected. The others watched, enraptured, as she groaned and thrashed about with his face buried in her crotch.

Scootaloo, who was now working Rumble’s cock with her hooves, whistled appreciatively. “Well, that’s a new one.”

“Nh... Yep. Not that often you see her like that,” the pegasus colt acknowledged.

“I want in on this.” Sweetie grinned and playfully smacked the Pip’s rump. “Lay on your back for me, would you?”

With only the barest pause in his ministrations, Pipsqueak rolled over, continuing his work on Diamond’s nethers from beneath.

Eager to get Pip to full mast, Sweetie cradled his erection between her hooves and gave him a few slow strokes. The colt tensed up at her touch, but kept his attention on Diamond.

“Sheesh, Pipsqueak,” Sweetie said as she watched him harden fully before her eyes. “I’ve heard of boys being growers, but who would’ve thought you were packing a monster like this?”

“Stop talking! Start sucking!” Scootaloo jeered playfully.

Rumble shot her a look of defiance. “I’d tell you the same thing, but you’d punch me, wouldn’t you?”

“Actually, I’ve got something else in mind for you...” Scootaloo said, coaxing her way under him with a playful whip of her tail to his chest.

Sweetie Belle rolled her eyes and bent down to plant a kiss on Pipsqueak’s length, right against his medial ring, before giving his shaft a long lick up to its flared head.

Pip groaned into Diamond’s crotch, in turn causing Diamond to stiffen at the change in sensations. She greedily pressed his head into her nethers, running her forehooves through his short mane and moaning without reserve. “Keep going! Yes! Earn that ass!”

Sweetie tried to take the head into her mouth; this took more than a little effort, but she was rewarded with a few drops of Pip’s tasty precum. Holding herself up with a foreleg on each side of Pip, Sweetie Belle swirled her tongue around his tip and worked her way down best she could, bobbing her head up and down his member. This was definitely the biggest cock she’d ever seen, let alone had in her mouth; she’d be impressed if Diamond Tiara could take it down to to the ring, nevermind all the way.

Pipsqueak threw his head back against the cushion and away from Diamond. “Sweetie! I can’t take much more of this...” he whimpered.

“Oh heck no!” Diamond exclaimed, having replaced Pip’s mouth with an eager hoof. “I’ve got dibs on that load!”

“Fine, fine,” Sweetie Belle pouted, retreating to Rumble and Scootaloo’s side and finding the two in a compromising position. Rumble was mounted on top of Scootaloo. She could still see his member outside, but judging by the heavy grinding going on between the two, that wouldn’t last for long.

Summoning all the willpower he had not to gush right then and there, Pip made his way over Diamond. He rested one hoof against her prone back, and the other against the cushion, next to her shoulder. His cock smacked against the crack of her ass, and slowly rubbed its way backwards down her cracks and across her sex as he leaned down to murmur in her ear. “You’re absolutely sure you want to do this, luv? It’s almost definitely going to hurt.”

“Shut up and do me.” Diamond grumbled between two labored breaths. “I never back down from a bet.”

Pip nodded and considered her rear end attentively, bringing his forehoof to his member to guide it to its target. Thankfully, between the lube and Sweetie’s saliva, they'd be fine on that side.

With her face almost buried in the cushion, Diamond still had some peripheral vision. She saw the other three watching with rapt attention. Rumble’s cock was almost certainly inside Scootaloo by now, but their eyes were on her back end nonetheless. Sweetie was no different. Judging by her little groans, she was most likely working her frustrations against her hoof.

Diamond’s world went into sensation overload when she felt it pressing against her entrance. Her teeth clenched, and her muscles tensed up.

“You gotta relax, Di.” Pipsqueak murmured. “I’m not gonna force my way in if you’re all scrunched up like that.”

He began massaging her hip right across her cutie mark, keeping the pressure even. “Can you relax for me? Take a deep breath?”

“I... I’ll try.” Diamond winced. “I’ve only done this twice before, and neither of them were close to as well hung as you are.”

Finally, after another excruciating few seconds of even pressure, Diamond gave in, and her warm tightness engulfed the head of Pip’s cock.

Diamond slammed a forehoof against the cushion and gave a surprised squeal. “Craaaap! It feels even bigger than I thought! Ah! It hurts...”

Feeling her frantic squirming, Pipsqueak moved to pull out. Before he could do anything, Diamond snapped. “Don’t you DARE take it out now!”

In her uncontrolled flailing, Diamond had forced herself backwards, taking a solid two inches of his member. Pip pressed his chest against her back to keep her from any further extreme movements. “Okay, okay. Let me know when you’re ready for more.”

Diamond Tiara winced and turned her head aside to try and look at the smaller stallion on top of her. “Nnh...at least I’ve taken the whole thing now, right?”

Between the feeling of her tailhole squeezing his cock like a vice, the intense effort of suppressing the desire to push further, and the knowledge that his medial ring was nowhere near her buttocks, it was all Pipsqueak could do to whimper noncommitally.

“Hah!” Rumble exploded, “Try again, Di! He’s barely in!” He looked down and found Scootaloo glaring at him. His cock had slipped out while he was distracted, and she looked just about ready to murder him.

"Sorry, Scoots," he nervously apologized, meekly pushing his length back into her and picking up the rhythm.

“Mmmmhh... better,” Scootaloo moaned as she slumped back down onto the cushion, resting her head atop Sweetie’s outstretched leg. “Be quiet, fuck me, and enjoy the show, would you?”

Sweetie, meanwhile, had grown bored of her hoof and levitated the strap-on off the table and to herself; there was no denying she was enjoying seeing Diamond on the submissive end for a change.

“More!” Diamond snarled.

Pip instinctively obeyed, slowly pushing in inch after inch.

“FUCK!” she shouted at a particularly sudden push. “How in Tartarus are you so big!”

“S-so-tight!” Pipsqueak moaned as Diamond’s struggling worked her warm insides around his sensitive member. “It’s like you’re a virgin back there!”

“I AM!” Diamond finally blurted out, before slamming her mouth shut with a hoof. “I lied to make myself sound cooler! Nnh!” Diamond bit the cushion to keep herself from screaming as Pip’s medial ring came to rest against her ass. “I always freaking do!”

“Oh, luv...” Pip cajoled, placing a gentle kiss at the nape of her neck. “You don’t have to lie to us, Diamond. We all know you’re the best. Most fillies I’ve bedded nearly run the first time they see my knob, but here you are with half of it up your tush on a lost bet.”

“Nngh! You really think so?” Diamond whimpered. Her eyes twitched close as she felt herself stretched wide again. It wasn’t hurting so much anymore. Letting the truth out like that, allowing all that stress to spill out, felt better than any fuck. Now, in her ass, and all over, she felt pure intensity, just a thrum of nameless feeling.

“You’ve certainly gone further than any other mare I’ve known.” He acquiesced, pausing again to allow her some rest.

“Damn straight!” Scootaloo called out between two moans. “You’d have to tie me down for him to get that thing anywhere near MY ass!”

“Gotta agree with my cock-sock here,” Rumble nodded without interrupting his thrusts, earning himself a whip of Scootaloo’s tail. “I wouldn’t want to take a chance with that thing either. Sweets?”

Sweetie, worn out from her second orgasm of the night, merely nodded, her half-lidded gaze not leaving the point where Pip’s cock ended and Diamond’s butt begain as he kept slowly pushing in.

“You know what the best part is?” Pipsqueak gently whispered into Diamond’s ear?

Diamond groaned again and pushed back against his face, enjoying the feeling of his chin in the nape of her neck. “Ngh. What’s that?”

Pipsqueak’s hips pressed against her buttocks. Diamond’s eyes widened like never before. Even with everything she’d gotten up to during these special poker nights she’d been holding for a few months now, she’d never felt so full.

“You’ve actually taken me to the hilt.” He chuckled, giving her a shallow thrust which pushed her rear end even deeper into the cushion and pushed his balls against her clitoris.

Diamond wearily smiled. “... I told you you had no idea how all in you were.”

Pip chuckled, and turned to their audience when he heard Scootaloo’s moans intensify. The pegasus mare was unceremoniously sprawled out with her chest against the sitting cushion and her read end up in the air. Rumble, pressed against her back, was giving her what looked to be an intense pounding. Motivated by competition, perhaps? In any case, they clearly weren’t paying attention to him and Diamond.

Sweetie, meanwhile, had her forehooves propped up on the kitchen table for leverage. Her horn was glowing, and judging by the second source of green light beneath her tail, she’d likely gotten curious and turned the strap-on toy to her own ass.

“Well, luv, looks like they’re not paying attention anymore, and I’m just about ready to blow a load up your arse. What do you say we get to the good part?” Pipsqueak crooned, before giving her ear a nibble.

“Mmm...” Diamond moaned. This was stimulating parts of her body she hadn’t even realized existed. “Show me what you got, stud.”

Pipsqueak braced himself and slowly pulled out inch by inch, desperately willing himself not to paint her insides there and then. He savored every moan and whinny this elected from the mare beneath him.

It was all Diamond could do not to scream right there; she could feel every ridge and bump, especially when his medial ring popped out. She brought a foreleg down beneath herself; working her clitoris only enhanced the feeling further. "Aaah! More!"

Pip didn't need to be begged to continue. He pressed back forward. Diamond was still incredibly tight, but taking things slow at first had thankfully loosened her up enough that he could penetrate her smoothly. Diamond moaned into the cushion as he bottomed out again, giving a few shallow thrusts to work her up further.

"Harder!" Diamond demanded. "Give it to me like you mean it! What's the point of betting if you're going to make it so easy!"

"You asked for it, luv." He smirked, before pulling out and almost entirely. This time, he took no time to slam his cock back in, smacking his hips against her and shifting the cushion forward. Diamond's precarious balance lost, and she found herself unceremoniously sprawled out as Pip began working into a rhythm.

"Aaah! Yes! Yes! So good! Hurts so freaking good!" She moaned. This was the ass pounding she'd been hoping for; this was the thrill of a risky loss finally catching up to her.

"All this trash talk," Pip said between two grunts of effort, "but in the end, you're just as happy losing, aren't you? "

"Yes! Oh Celestia, a thousand times yes!" Diamond kept moaning, half-muffled by the increasingly crumpled cushion she was getting driven into by the colt's all-out thrusting.

"Nngh! You're just as happy getting knocked off your hooves and having your tush rammed in by some scrawny runt, aren't you, luv?" If Pipsqueak had been shy before, he wasn't showing it anymore. "I hope you're ready for it, luv, because here it comes..."

The colt gave one final push, pressing his body against Diamond's as hard as he could, his chin coming to rest just over her shoulder. His cock penetrated her one last time, even deeper than before, and he spilled shot after shot of warm cum inside her, filling her with his seed until there was nowhere for it to go except leaking around his shaft.

Diamond gave an uncontrollable whinny of pleasure, ecstatically rubbing her head back against his. Her nethers gushed with her own fluids, coating her crotch and the cushion she'd been squeezing between her thighs.

The two of them laid there for what felt like forever, out of breath and riding the afterglow of their orgasms.

"That... was amazing." Somepony spoke up. Scootaloo, Pipsqueak determined. The pegasus, held between Rumble's forelegs and nestled into the fur of his chest, was smiling at them. "I never thought I'd see Diamond letting herself go like that." Rumble looked a bit too tired to move, but he nodded in agreement.

Sweetie raised a moderate uproar of her own as she reached her third and final orgasm of the evening and allowed herself to crash down onto her cushion panting. The lube-coated toy unceremoniously clattered to the ceramic floor. "You guys were soooo hot."

"Thanks for coming, everypony," Diamond smiled, enjoying Pip's warmth against her back and the feeling of his softening member still inside her. "And thanks for showing me a good time, Pip. What do you say we all just... crash here for a while?" Diamond yawned. "We can take care of the cleanup and the money tomorrow."

Pip flopped onto his side, pulling her with him. "... sounds good to me. Want me to...?" He mustered some effort to pull out of her, but Diamond scooched back against him.

"Nope." Diamond curled up for comfort, happy to have him draped over her back. "You be the big spoon for a while. I'm happy like this."

Rumble dragged Scootaloo and himself over to them, sliding his sitting cushion up against Diamond's. His head came to rest on Pip's back, while Scootaloo nestled between the two of them. Sweetie wearily pressed herself against Rumble's other side, and the pegasus instinctively draped his wings over the mares on either side of him.

Just like that, on a messy pile of cum-stained sitting cushions, the fivesome drifted away peacefully, satisfied with their escapades. With a little luck, their hangovers wouldn't be too bad in the morning, and Diamond's ass would only be sore for a few days.