Interspecies Intercourse

Once they were both acclimatized to the feeling of how exquisitely their flesh connected, Jack tightened his grip on her and started grunting as he delivered swift, powerful and very deliberate thrusts into Lyra, who was yelping in tandem and breathing heavily through her nose. Immediately below the action was Bon Bon, who smiled at her unique perspective, she found the view of her girlfriend's fuck hole being split open by Jack's very masculine dong insanely arousing and the mesmerizing sight of Jack's heavy nut sacks swinging back and forth as he fucked her was borderline hypnotic, the sexual energy was high. After a minute of Jack fucking Lyra at a decently steady pace, Bon Bon decided that he needed to step up his game and simply said "Faster"

Never one to disappoint a lady, Jack increased his speed, breathing heavily while Lyra devolved into sustaining one continuous moan of ecstasy, the bed creaked as it rocked back and forth in tandem with the constant clapping of Jack's hips against Lyra's firm pillowy buttocks. Jack watched Lyra's plot jiggle and went "Yeah, take it you slut..." before swinging his hand down and giving a hard slap to her ass, making her yelp in shock and the interestingly pleasurable pain until going back to focusing on the thick man meat claiming her marehood.

Inspired by Jack's dirty talk, Bon Bon decided to give some encouraging words of her own that, if things went her way, would get them both to their climaxes much sooner than anticipated. Lyra and Jack had felt their orgasms building the second they became intimately familiar with the feeling of each other's flesh, Bon Bon's sex talk was the final straw.

"You gonna cum? Do it, fill her, breed Lyra like the dirty mare she is!" Jack gritted his teeth and scrunched his eyes closed as he started pounding away at Lyra's clenching cunt like a wild animal, Lyra's eyes crossed as drool fell from her lips, they were close to the edge...

Bon Bon continued "That's it! Cum inside her!"

Jack let out a guttural cry as his arms shot forward, both of his hands grasping onto Lyra's horn, tugging her head backwards as he rammed himself as deep into her sopping wet cunny as he could and firing thick ropes of hot spunk that went crashing against her cervix. Lyra gave a her own muffled moans of elation as she creamed on the hot throbbing inches of human cock filling her nethers, her eyes rolling in their sockets while she felt the warmth of his baby batter coating her walls. Bon Bon was smirking as she took note of the smaller details, like the quivering lips of her girlfriend's cunt and the way Jack's balls seemed to shrink the second he had finished nutting inside her, it was perfect.

Jack let out a breath he didn't know he was holding as he let go of Lyra's horn and pulled out, leaving her to collapse on her side in exhaustion. Bon Bon chuckled before looking at Jack and asking him "So, what do you think big guy? Was she good?"

As Bon Bon got to her hooves and turned to face him, Jack nodded and replied "Yeah, she was very good... not to brag but it kinda looks like I really did a number on her, so I don't think she's really in any kind of state to say how good she thought I was huh?" Bon Bon looked at Lyra who was still shivering in the aftershocks of her orgasm as cum leaked from her folds, she was obviously too tired and too sensitive to be doing anything other than resting so it was clear that Jack had delivered well.

Bon Bon smirked and said "Yeah, she's usually like that after sex but trust me, you performed splendidly and I should know, I was watching! Now that Lyra's out for the count though, I guess it falls to me to make sure you leave this place looking and feeling your best! So, how about I clean your impressive equipment with my mouth? Sound good to you?"

Jack smiled and went "Well... such a kind offer, who am I to say no?" Bon Bon took a moment to admire Jack's semi-erect cock, shining in the light from the slick and slippery coating of cum and mare juices he had acquired from fucking her girlfriend into a stupor, though Bon Bon decided to start with the equally soaked cum tanks that had almost fully emptied themselves deep inside some tight pony pussy seconds ago. Bon Bon pressed her nose up against Jack's nut sack, his throbbing member resting against her face as she inhaled and shuddered in arousal as she breathed in the masculine scent of his package, the intoxicating smell of sex was thick and heavy around his human junk.

Bon Bon planted a couple of gentle kisses to Jack's spunk factories before dragging her tongue across them in a long lick, salivating at the addictive and slightly salty flavor that graced her taste buds, compelling her to take yet another lick and then opening her mouth as wide as she could to take both balls past her lips and into her warm and wet gullet. Jack grunted in approval as Bon Bon tenderly sucked on his crown jewels, exploring the texture of his skin with her tongue and treating them with some delicate dedication, these were the things had so lovingly packed her girlfriends pussy with jizz, they deserved to be worshiped and respected for delivering such a generous payload!

After Bon Bon was satisfied that Jack's fuck sacks were suitably "clean" she moved onto the main point of interest, his thick cock. Again she started off small, applying soft kisses to the base of his rod and gradually kissing her way up his shaft until planting one big kiss right on his tip as well as giving the head of his fuck stick a tentative, experimental, very quick and small lick almost as if she were testing his taste in case his cum cannon wasn't quite as nice as his fat nuts. Seemingly content that his dick was just as good if not better than his churning balls that were slowly swelling with another load, Bon Bon slipped his helmet into her mouth and then... did something unexpected.

What Jack had expected was that Bon Bon would start sucking and begin gradually taking more and more of his length into her mouth, then would bob her head back and forth, standard blow job stuff... what she did instead was take a deep breath in through her nose and then completely fucking engulf every single inch of him down her throat like it was nothing in the space of no more than one second, deep-throating him instantly, making it seem almost as simple and easy as breathing. Jack, understandably, groaned loudly as he grabbed onto Bon Bon's head with both hands and practically growled "HOLY FUCKING SHIT!"

The moist cavern of her mouth sucking with gusto, the soft tongue caressing his skin, the tight throat squeezing his boner... there was no way Bon Bon was this naturally talented, she'd sucked dick before, a lot. Bon Bon ignored Jack's outburst and carried on, mercilessly pleasuring him in her maw and not once gagging her having her muzzle anywhere other than pressed into his crotch, the skill was legendary and relentless and eager desire to milk the cum from Jack's balls was unmatched, why had Jack not started fucking ponies sooner than this?

Jack decided to make up for lost time and started hammering away at Bon Bon's mouth, her only response was to look up at him like an innocent little filly and bat her eyes while he continued to defile her, her muzzle being repeatedly mashed up against his groin while his swinging saliva-coated balls wetly slapped her chin.

With Jack still being so sensitive from fucking Lyra and his cock being so perfectly stimulated from Bon Bon's expert throating abilities, it wasn't too long before his climax began to approach extremely rapidly. Jack hilted himself in Bon Bon's face and made aggressive moaning sounds as he sent every last milliliter of his baby batter down into Bon Bon's waiting stomach, Bon Bon herself allowed Jack to hold her there, the feeling of a pulsating cock in her throat making her sore and aching pussy lips even wetter than they were before, winking with desperation. She'd have to wake Lyra up and get herself licked out when Jack left.

Once Jack was spent, he lazily moved Bon Bon's head back and forth, grunting as he made sure he was thoroughly drained and had gotten all the pleasure he could from Bon Bon's mouth before releasing his grip on her mane and allowing her to move back. Bon Bon moved away, still sucking as she moved back until Jack's exhausted bitch breaker fell from her lips before she went "Mmm... there you go, nice and clean!"

Jack chuckled and said "A very dirty way of getting clean! I don't know about you but I'm gonna have to tap out here, if you want me to make you cum then it's gonna have to be fingers or tongue, I'm not sure I've got another load in me even if the promise of more pussy could wake my dick from its slumber. You alright with that Bon Bon?"

Bon Bon smiled and replied "That's very sweet but don't you worry, I'll be sure to wake up my lazy girlfriend here and put her to work between my legs, I'll be more than fine. Thanks for indulging us in this little threesome though, you go rest up and rebuild your energy!"

Jack nodded and put his clothes back on, though as he was about to leave he turned back and asked "Wait, before I go Bon Bon... I just gotta know something... how did you come to be so good at deep-throating?"

Bon Bon rolled her eyes in a "of-course-he'd-want-to-know-that" way and explained "Lyra has, on special occasions, used her magic to give herself her own male endowment that she tends to make larger than average, so I've had some practice, It's mainly blow jobs I give her, though if I'm feeling particularly generous I let her give my pussy a go and if I'm feeling REALLY amorous and she asks nicely, I'll even let her take my ass. When we're ready we're gonna ask Twilight if she can give Lyra the same equipment but with working sperm instead of just shooting blanks so that we can have children, anyway I'm getting sidetracked. Long story short, I've sucked Lyra's magic cock, a lot"

Well, that answered that question! Jack left feeling refreshed, rejuvenated and ready to eat lots of food to regain his energy and build up some fluids for any future sexual escapades he might have in town. Despite learning that interspecies relationships were legal, had actually had the guts to have sex with a pony and knew that there were plenty of ponies who would be interested in a relationship, Jack still hadn't gathered up the courage to ask Fluttershy out on a date even though there had been numerous opportunities to do so. Then there was Fluttershy who, as expected, was equally too nervous to ask Jack out on a date either, they were both too afraid of what it might mean for the friendship if things went south or just the prospect of being rejected by the one they were so enamored with, the time just wasn't quite right yet.

• one month later -

It had been almost four weeks and despite Jack's best efforts, he still couldn't bring himself to ask Fluttershy out on a date, her friends were giving him plenty of advise but none of it seemed to work and they had all kept their promise not to spill the beans about his feelings, something that they were handling very well in comparison to Pinkie Pie who was going insane at the prospect of not being able to say anything. One piece of advise that was helpful however was that he should consult the cutie mark crusaders, he knew the three fillies decently enough through their big sisters and word on the street was that if you had a problem then be you griffon, hippogriff, pony or otherwise, then they could help you with a problem. Jack was skeptical at first, surely they were too young to know about confidence and relationships, right?

Jack figured he didn't really have anything to lose by talking to them and decided he may as well visit the club house at sweet apple acres and give it a shot, who knows? He might grow a pair and ask out Fluttershy.

If only Jack had known that Fluttershy felt the same way, the unfortunate thing was that although Fluttershy had been brave enough to confide in her friends that she felt the way she did about Jack, she had also sworn them to secrecy, which only drove Pinkie Pie more around the twist while the rest of them accepted that if Jack and Fluttershy ever got together then it would have to happen on its own on their own terms. If they left it alone then perhaps nature would take its course and the powers of fate, destiny, love and romance would prevail. Jack found his way to the clubhouse and after carefully crouching down and hoping the flimsy wooden planks would hold his weight, he knocked on the door and, after a few seconds, was face to face with the crusaders themselves, Sweetie Belle, Applebloom and Scootaloo.

Applebloom, as self-appointed leader of the trio, gasped as she went "Well howdy there Jack! What are y'all doin' around these here parts?"

Jack said "Hi you three, assuming that I can fit inside your little club house, think you can help with a problem I've been having recently?"

Sweetie Belle looked Jack up and down before checking what room they had in the club house, then turned back and, in a nervous tone, said "Well Jack, considering that not even Bulk Biceps could fit in our club house properly... it's probably safe to say that you can't either..."

Scootaloo quickly cut in, afraid that they'd disappoint him, exclaiming "Doesn't mean we can't help you though! How about you just sit down on the grass and tell us your problem, then we'll figure a way to help you! How does that sound?"

Jack nodded, climbing his way back down to ground level and sitting on the grass with all three crusaders following soon afterwards and standing side by side in front of him, ready to help in any way possible. Applebloom asked "So what seems to be the problem?"

Jack said "Well... it's kind of a grown up thing but since you've got your cutie marks I figured you'd still know how to deal with it, have you girls ever had to help someone before with like... relationship stuff?"

The three of them blushed in embarrassment as they remembered the last couple of times they tried to play matchmaker, both of which were with Big Mac and although they had succeeded the second time around, they soon realized that matters of the heart was not exactly the strongest point when it came to their talent of being helpful. Applebloom replied "Aw shucks Jack... we don't really know how to play cupid..."

Jack shook his head and clarified "Oh no no no no no, I don't want you to try and set me up with someone, I just need help in asking Fluttershy out on a date, that's all!"

Sweetie Belle perked up and went "Really? That's great! Fluttershy used to be our foalsitter! What is it that you're so worried about other than her just saying "No" or something?"

Jack thought for a second and said "I don't know really... I guess maybe I'm worried that I'll ruin the friendship?"

Scootaloo went "Pfft! That's silly! Trust us, Fluttershy is such a nervous pony that making friends with her is difficult enough so you're basically half way there! If you're good enough to be her friend then asking her out won't do anything to spoil it and, bonus points, you already know what kind of stuff she likes and can cater to her emotions easy peasy!"

Oddly enough, having that information said out loud was quite reassuring, much better than the "confidence tips" of their older sisters. So the emotional connection was there, maybe Fluttershy felt the same way? Though that left a slightly more awkward question.........

Jack cleared his throat and said "Um... what about... physical stuff?"

Applebloom deadpanned and said "We know what sex is dummy, just say "sex" you hear? Anyway, we don't know what kind of sex Fluttershy likes, you'd think she'd probably prefer gentle love-makin' the way she acts but for all we know she could be a total freak in the sheets. Besides, if you ask her out then you'll be able to find that out for yourself! You worried you don't measure up or something?"

Jack shrugged and went "I dunno... maybe?"

The crusaders all exchanged looks before huddling together and speaking in hushed whispers. Jack sat patiently as they all talked about whatever it was they were talking about, he felt slightly odd to be consulting children about this kind of thing but he didn't know what else he could do at this point, he knew he was perfectly within his rights to date Fluttershy so why was he being so apprehensive about it? While he was working through that, the crusaders turned back to him when Scootaloo asked "Have you had sex with anyone yet Jack?"

Jack, never having been one to kiss and tell, lied "Nope, no sex yet"

Sweetie Belle suddenly went "Mmhmm, as I thought. There's your problem Jack, you're subconsciously worried that you won't be able to satisfy Fluttershy. Luckily for you, we have the solution!"

Jack, intrigued, said "Oh?"

Applebloom nodded "Uh-huh, you need some practice girls to tell you if you can properly satisfy a mare! You'll start off with Scootaloo, she'll be your practice girl for vaginal, I'll be handlin' the oral side of things, which just leaves Sweetie Belle who'll be takin' you in her butt!"

Jack's eyes flew open wide in shock, they thought that the best way to help was to have sex?! Jack decided to break his "don't kiss and tell" policy, not because he was uncomfortable with it but because he didn't want to feel as though he was taking advantage of them, he confirmed "Whoa whoa whoa wait girls, wait, I lied. I've had sex with Lyra"

Applebloom chuckled and said "Yeah, nice try Jack! Come on, you've got nothin' to worry about, we're happy to help you get rid of your subconscious phobia of not bein' able to perform for Fluttershy and we ain't takin' no for an answer! Us three have had sex before but relax, you don't have to try and impress us, we know we're gonna enjoy this and we're just goin' the extra mile by provin' it to you! Don't go thinkin' that we're gonna fake our enjoyment for your benefit, you can trust us Jack, we're the cutie mark crusaders!"

Jack could tell from Applebloom's determination that he probably wasn't going to be able to get out of this, Jack didn't have a problem with being sexually promiscuous but if Fluttershy had a problem with it then she might not be too keen on going out with a guy who had already slept with two mares and three fillies, three fillies who just so happened to be the little sisters of some of her closest friends...... it seemed that the cutie mark crusaders had convinced him that, after having sex with them, he should probably ask Fluttershy out sooner rather than later.

As Jack unbuckled his belt as he went "Alright, if you really think this will help me then sure, why not? Though I'll tell you right now that with my species, we can cum twice in a row but that's it, after that we need a bare minimum of ten minutes before we go for a third ejaculation, OK?" Jack shuffled his pants and underwear halfway down his legs, his slowly engorging member proudly on show for the barely legal trio.

Applebloom, seemingly unphased, replied "No problem, I'll just use my mouth to get you ready, that way you can pump your first load into Scootaloo's pussy and then bust a nut in Sweetie's butt!" Applebloom crawled in between Jack's legs and started off with small affectionate kisses up and down his shaft with the occasional little lick, gently coaxing his cock into becoming fully erect so that she could engage in the proper fellatio that she had promised.

While Applebloom was getting Jack harder, Sweetie turned to Scootaloo and asked "Hey Scoots, since Jack is gonna be going in my butt, would you mind getting me ready? Don't exactly have any lube around here"

Scootaloo nodded and said "Sure, I need to prepare myself a little anyway, so getting you ready will help rile me up at the same time!" With that, Sweetie Belle turned away and leaned her front half down on the grass, sticking out her cute filly butt and suppressed her gasps of pleasure as Scootaloo got to work, slavering her salivating tongue around Sweetie's pucker both inside and out while she reached between her own hind legs to rub a hoof against her steadily lubricating pussy.

The sight of Scootaloo masturbating while she eagerly went to town on Sweetie's ass hole with her tongue was only accelerating Applebloom's efforts to give Jack a stiff rod, it was maybe only one minute before he had a raging hard-on for Applebloom to suck, a fact she pointed out when she smirked and said "Mmmmm...... Fluttershy is lucky to have a human like you that wants to fuck her if this is the heat you're packin'! So, now that you have a nice big boner for me to blow, just kick back and relax so that we can prepare this big bad boy for some fuckin'!"

Being that Applebloom was young and inexperienced, she didn't see the value in slowly building up to a blow job the way that Bon Bon did and went for the direct yet effective approach of cramming as much dick in her mouth as she could and sucking vigorously while bobbing her head up and down. Jack groaned and clenched his fists at his sides, while it didn't build up the anticipation of feeling the bliss of a girl being generous enough to take a cock in their mouth, that wasn't to say that it was any less enjoyable when they did. Applebloom may not have been subtle, she may not have used her tongue on his member as much as she should've and she didn't pay any attention whatsoever to his balls but her mouth was warm, wet and she knew the basics of a good blow job, she knew all the things that she needed to know for the moment.

Partway through the blow job however, Applebloom attempted to push herself further down in an effort to squeeze Jack's fuck stick into her throat, though her small gags and failure to actually perform said action made it clear to Jack that she was struggling to do something that, to be honest, she was not obligated to do, especially considering that she wasn't intending to make him cum. Applebloom persisted nevertheless but acknowledged that she, quite literally, needed a helping hand and tapped a hoof against Jack's right insistently, trying to communicate what she was asking for. The hoof movements she was making apparently weren't clear enough because Jack wasn't getting the message, making her temporarily pull off of him to boldly proclaim "Land sakes Jack! A girl wants her man to take charge every now and then! Use your big human hand thingies and push my head down!"

Applebloom stuffed Jack's man meat back in her mouth and this time when she tried to take him down her throat, he placed a hand on her head, started pushing and after a few seconds, his thick cock was gradually forced down into the depths of Applebloom's gullet. Applebloom took it surprisingly well considering she wasn't a deep throat maverick like Bon Bon and had managed to stay relatively calm when her nose finally made contact with Jack's crotch, it was then that she let her throat muscles do the work while she just held herself there. To Applebloom's credit, although she did hack and cough on account of never having had her gag reflex put to the test, she did have the will and determination to keep her lips firmly pressed to Jack's groin, never letting a single millimeter of his shaft leave her mouth no matter how desperately her body screamed at her to back off and catch her breath.

Jack hummed in appreciation, the strength of Applebloom's ability to ignore her involuntary attempts to clear her airways and expel the inches of cock currently lodged in her esophagus was impressive, he was already hard enough before she did it and they both knew it, she didn't deep throat him to make him hard... she did it because she wanted to. Only when her eyes started to roll and she became light-headed from lack of oxygen did she tap Jack's hips to signal that he could let go so that she could finally launch her head backwards and take in deep gulps of air, the irritation at the back of her throat making her cough. Applebloom gave a little giggle once she recovered, proud of her work at giving Jack one of the hardest erections he had ever experienced.

Applebloom went "Woo nelly! That sure was somethin'! Sorry if I gave you a scare there, I don't want you worryin' none about me. I like gettin' out of breath! My big sister Applejack says I have a kink, I think she called it as-fix-a-shun or somethin'? Anyhow, I'm fine, I like not breathin' for a while! It's fun and it feels really really good afterwards!" That did put one worry of Jack's to rest, though he hoped that Applejack had at least told her little sister that she should be careful when indulging in the ways of asphyxiation play when it came to sex, though not nearly as much as he wondered how Applebloom discovered that being choked until almost passing out was her kink, by accident?