The Lost Lovers

"You sure you're gonna be alright while I'm gone sugar cube?" Applejack was going into town to pick up some cupcakes from Pinkie Pie but was leaving the club in the middle of the day to do so, so she wanted to make sure Fluttershy was up to the task of keeping things running and tending to the needs of the club members all on her own. It wasn't that she necessarily doubted Fluttershy's ability to handle it, she just wanted to make sure she wasn't overwhelmed, the club was surprisingly popular after all.

Fluttershy rolled her eyes and said "Relax darling, I'll be just fine! I can handle it, you just go and do what you gotta do and I'll hold down the fort here OK? You deserve a break"

Applejack smiled and said "Thanks sweetie, I'll be back as soon as I can OK?"

Fluttershy nodded and Applejack left the building just as Rarity walked in, Fluttershy smiled and said "Hi Rarity! Here to suck off Chester again?"

Rarity chuckled and said "You know me so well dear, say, where was Applejack headed off to?"

Fluttershy said "Oh, she's just heading to Sugar Cube Corner to pick up some cupcakes from Pinkie Pie"

Rarity thought for a moment before grinning deviously and saying "Bet you $10.00 that they'll end up fucking"

Fluttershy mused on that for a moment, it was a risky bet for Rarity because Pinkie only ever had sex with a customer if they happened to be the 100th customer that day, the odds were in Fluttershy's favor. Considering and confirming that simple fact, Fluttershy gave an equally wicked smile and said "You're on, $10.00 to you if they fuck, $10.00 to me if they don't".

Applejack approached the doors of Sugar Cube Corner, just before she walked in a boy walked out who she knew as Featherweight, with an extremely satisfied look on his face. Applejack breathed out a sigh of relief, from the looks of things it seemed he had been the lucky one to be Pinkie Pie's 100th customer that day, this meant she didn't have to be away from the club for too long and wouldn't be roped in to some casual sex, ordinarily she wouldn't have minded a bit of kinky fun with Pinkie Pie but she was eager to get back to the club so that Fluttershy didn't spend too much time having to go it alone at the front desk. Applejack walked in and immediately Pinkie gave a huge gasp then started jumping up and down shrieking "Yay! Applejack! You're my 100th customer today! Yipee!"

Applejack went slack-jawed and buggy-eyed, how was she the 100th customer?! Applejack just went "How... but what...then... hold up hold up! What about Featherweight?! Wasn't HE just your 100th customer?!?!"

Pinkie gave Applejack a quizzical look and went "No, what gave you that idea?"

Applejack just said "Well he looked all relaxed and with a big goofy grin on his face, he looked like a guy who had just had his nuts drained! You tellin' me lies or was he really not your 100th customer?"

Pinkie giggled and said "Oh my sweet little Applejack, Featherweight looked like that because he had just had a really tasty refreshing chocolate milkshake on a really hot day ya big silly!"

Applejack face-palmed in her mind, her dirty mind had, in an effort to avoid having to have sex with Pinkie Pie, actually tricked her... into having to have sex with Pinkie Pie. What made it even more of a bitch was that ever since Applejack and Pinkie Pie had found out they were distantly related and had also both lost their virginity via incest, Fluttershy had been eagerly looking for a window where she could schedule a time when all three of them were available so that she could watch Applejack and Pinkie Pie go at it and simply enjoy watching it. When Applejack remembered that particular fact, she came to an epiphany, if she was really going to have to have sex with Pinkie Pie then she could at least do something for Fluttershy as a little "sorry" for making her wait so long. Applejack smiled and said "OK Pinkie... but on one condition..."

Pinkie Pie rolled her eyes and said "Yea yea, I know, you need the cupcakes, right?"

Applejack paused for a moment then groaned and went "Alright fine, TWO conditions! One is I need the cupcakes obviously, the second is... let me film us doin' it".

Pinkie Pie gave a wide grin "Oh of course! Heck, if you didn't suggest it then I might have suggested it myself! Come on! Let's go!" Pinkie started walking upstairs to her bedroom with Applejack following close behind. Speaking of behind, while she wasn't initially thrilled about fucking Pinkie Pie, what never seemed to escape her attention was just how wonderfully massive Pinkie Pie's ass was, it was especially noticeable now as both cheeks jiggled like jello with every step she took. Applejack became slightly wet, she knew Pinkie Pie loved anal sex so much to a point that she'd had to begin an exercise regime to keep her pucker sufficiently tight, Applejack licked her lips... she couldn't wait to get her hands on that big bouncing ass. In fact so hypnotized was she by Pinkie Pie's round and rotund buttocks that she couldn't resist giving Pinkie a quick spank just before they entered her bedroom, Pinkie let out a small yelp on impact and went "Ooh, Applejack, so eager!" Applejack just chuckled as they entered the bedroom, getting her phone out and pressing "record" before positioning it appropriately for the best view of the ensuing fuck session on a nearby shelf.

Applejack let out a breath and said "So Pinkie, what you got a hankerin' for?" Applejack had a feeling she already knew but didn't want to jump to conclusions, she had only just learnt that lesson by mistaking Featherweight's "That was a tasty refreshing drink" face for a "I just received the best blow job ever" face.

Though it seemed Pinkie, astonishingly enough, was predictable when it came to sex as she retrieved a strap-on and a bottle of lube from her bedside drawer and said "I don't suppose you'd mind putting this on and fucking my ass with it would you?"

Applejack chuckled, taking the strap-on and lube from Pinkie's hand and saying "I think I can manage that".

"Yipee!" said Pinkie as she leapt onto her bed and immediately got on all fours, revealing that not only did her skirt not even come close to covering up her wide expanse of ass but also that she wasn't wearing any panties. Applejack had to wonder, why was this girl always going commando? Then it occurred to her that if Pinkie Pie had a policy of letting every 100th customer fuck her, not to mention the fucking she did in her spare time, having to constantly change panties would become a chore. Then there was also the fact that with how often she had sex with people, panties had essentially just become obsolete for her, she'd be pulling them down more often than up, so why bother wearing them at all? Applejack decided to remain clothed for this sex session, she was horny and a little damp sure, though not really enough for her to get naked and clap flesh. She slid the strap-on up her legs and tightened the straps around her waist, she looked at the lube for a second... obviously she was going to use it, however if she was doing a video for Fluttershy, she figured she might as well have a little bit of fun first before getting down to the main event.

Applejack walked around Pinkie's bed until she was directly in front of her, Pinkie looked at her with a confused look and said "Um... Applejack, not sure if you noticed, but my butt would be on the other end".

Applejack gave a wry smile and said "Oh no no, I noticed. In fact with an ass as fat as yours it'd be hard not to notice, I just thought that before I lube up that you might be hungry".

Pinkie still hadn't caught on and went "What do you me-ughfk!" Pinkie was interrupted when Applejack suddenly rammed the strap-on down her throat and started thrusting away at her face, ordinarily Pinkie was excellent at controlling her gag reflex when she was giving a blow job but Applejack had taken her completely by surprise, leaving her no time to properly prepare for it and consequently making her constantly cough, gag and heave at the rough treatment she was receiving.

Applejack was enjoying fucking Pinkie's face, the noises of discomfort she made only made it better, she grabbed hold of Pinkie's head and said "Yeah, you like sucking my dick, bitch?" Applejack gave one final deep thrust and held herself there, Pinkie going red in the face as she struggled for air, Applejack only finally pulled out when Pinkie started trying to push her away. Pinkie gasped loudly and panted, strings of saliva dripping from her lips, Applejack just smiled and rubbed the strap-on all over Pinkie's face, tapping her cheeks with it here and there. When Pinkie finally had enough air in her lungs to talk she said "Geez... fucking hell Applejack, a little warning would have been nice!"

Applejack stood back, then promptly slapped Pinkie in the face and just said stoically "Fuck you", it seemed Applejack's sadistic streak was making a small appearance.

Pinkie Pie rubbed her face and said "That's what I've been waiting for you to do! Fuck me! Oh and also, ouch and ow! No need for the slap! Now come on, my butt is waiting!" Pinkie shook her hips from side to side and Applejack returned Pinkie's behind. However, Applejack still wasn't ready to fuck Pinkie, so when Applejack spread Pinkie's massive butt cheeks, rather than feeling a thick stiff strap-on cock stuff in her ass, Pinkie instead felt Applejack thrust her face in her crack to start hungrily licking at her asshole. Pinkie moaned in pleasure this time as she said "Mmm... it's not quite anal sex but it's a start!" Applejack started with small quick licks at Pinkie's twitching pucker just to get her back door decently coated in saliva, after that she focused more on the pleasure side of things by applying long drawn out licks to her rear, Applejack was almost impressed that Pinkie's fat ass was so big that it almost enveloped her head, she grabbed onto the cheeks and gave them a wobble before giving each of them a smack, this was truly an ass that deserved some worship.

Just as Pinkie's moaning reached a certain pitch with her pussy beginning to clench more and more frequently, Applejack stopped her tonguing instantly and removed herself from Pinkie's butt, she didn't want to make Pinkie cum just yet. Pinkie was already sweaty and panting and the sex hadn't even really started yet, though that wouldn't last long, Applejack gave a couple of kisses to Pinkie's fat rear before finally opening up the bottle of lube and smearing it all over the strap-on, ready to penetrate Pinkie's posterior... though she couldn't resist pumping Pinkie's asshole with a couple of fingers as she applied some lube to her back entrance. Applejack held onto Pinkie's hips, to which Pinkie said "Whew... you finally gonna hump my juicy hindquarters? Give me a real good pounding?"

Applejack grinned and said "Girl, by the time I'm done with you you'll be wishin' I hadn't come 'round today, I'm gonna fuck you so hard that you'll have to redefine your own concept of a what a real poundin' is!"

Pinkie looked back at Applejack with her game face on and said "Bring it".