Chapters Jack found it interesting that the ponies around wanted to know his sexuality, they insisted that they weren't coming onto him and were just interested to know about him and this other world he supposedly came from, Twilight had suggested that he may have come through the mirror portal but based on her description of the humans there he came to the conclusion that he was definitely from a different human world and that the one she visited must have just been a different dimension entirely.
After a couple of months of settling in and accepting that there was not really any way to return to his own reality, he started looking for a job so he could earn some bits and maybe buy a house in town. Finding a job was surprisingly easy because back home he was a door-to-door salesman and it just so happened that the "quills and sofa" shop had an opening for a customer assistant, which payed decently well considering they only sold two things, though the pay rise he got for suggesting that they start selling beds as well certainly helped.
He found settling in easier than he thought, Equestria seemed to work basically the same as the human world but just so happened to be populated by cheerful multi-colored equines. Jack decided that staying here would be better than trying his luck in the mirror portal's version of the human world because although he had just appeared out of nowhere from another dimension, he didn't want to go hopping into different dimensions and messing with their affairs unless he was forced to by the mysterious force that had brought him to Equestria in the first place, might as well stay in on place and stick to it, especially after working so hard to merge into pony society!
He had made plenty of friends in town too, Pinkie Pie was the one most eager to be friends with him and he didn't mind spending time with her, though she was a friend best enjoyed in small doses during her parties. He had a decent friendship with a few other ponies around town, including the rest of the team who embodied some kind of set of magical relics called "the elements of harmony" or something like that, Jack couldn't quite wrap his head around it, though what he did understand was the close friendship he shared with Fluttershy, he'd always been an animal guy and she'd been all too happy to show off the wonderful creatures she looked after at her quaint little cottage home.
It wasn't too long before he was able to afford a small home, it wasn't anything fancy and it needed a little bit of renovation but once it was spruced up and had some furniture in it then it would be perfect! There was only one problem left, now that he was part of the community... what were the chances of getting into a relationship with some one? Jack was trepidatious about this, thanks to Twilight he knew about some of the species that lived in Equestria and beyond but he had no idea if interspecies relationships were allowed, not to mention that he had grown up with a legal system that was very clear on that subject.
Jack figured he might as well ask Twilight about it, she seemed very intelligent and he was sure that she'd be able to explain the law in a way he could understand, the way things were run in Equestria were almost identical to his original home, he just hoped that the law was slightly different considering he was the only human... plus he noticed that he was starting to really crush on Fluttershy, they had a lot in common.
Jack made his way to Twilight's house and knocked on the door, a few seconds went by and Spike opened the door, as per usual his cheeks went red like he was feeling bashful yet acted completely normal as he said "Oh hey Jack! I'm guessing you're here for Twilight huh? She's sat at her desk reading a book, no surprises there. Come on in big guy!" Jack smiled and walked in with Spike closing the door behind him.
Jack walked into the study and just like Spike had said, Twilight was sat at her desk reading a book that she had probably already read a few dozen times. Jack cleared his throat to get her attention, Twilight tore her eyes away from the page for a split second to see where the noise came from before her eyes then lit up as she went "Jack! It's a pleasure to see you! Excuse me a second while I just put this book away!" Twilight closed the book and levitated it back onto the shelf, Jack still found it strange that there were actually ponies here who could use magic, fly or were extraordinarily gifted farmers. Twilight turned to Jack and asked "So Jack, what brings you here on this fine day?"
Jack, forcing himself to remain calm, said "Well Twilight, I was actually hoping to learn about the law here? Regarding... y'know, relationships?"
Twilight, confused, replied "Relationships? Well you already know that your sexuality isn't an issue, what could you possibly need to know?"
Jack explained "Well, I'm the only human in Equestria sooo......"
Twilight caught on and gasped before going "Of course! You're wondering if companionship and intimacy between two different species is acceptable! How could I have overlooked this? Jack, you'll be pleased to hear that interspecies relationships are most certainly acceptable, it's not exactly common but it definitely happens! I think Rainbow Dash even hooked up with a griffon once, the sex was very rough apparently"
Jack sighed in relief and went "Whew! Thank goodness, it's nice to know I can go out with a pony or a dragon or whatever without it being a crime! The law in my world certainly wouldn't have been OK with it... actually with that in mind, I don't suppose you could give me quick summary of the legal side of sex in the country could you?"
Twilight grinned like a teacher who'd been given a fair wage and exclaimed "Certainly! I can't think of much that isn't legal so it shouldn't be too much of a challenge, let me just grab my law book and bullet point it for you! Shouldn't be difficult, now let me see, where is it?" Twilight scanned her eyes along the shelves before pulling out a book and saying "Aha! Here we go! The governing laws of Equestria by royal decree, all I need to do now is skip to the... uh... let's call it the "sex section" for want of a better phrase!" Twilight set the book down on the desk and flipped through the pages before settling on one particular chapter and did a bit of speed reading.
After a minute she said "Uh-huh, OK I think I can sum all of that up decently well enough. First things first, as discussed, interspecies relationships are completely fine but genetics dictates that children are impossible, next we have incest which is nothing unusual, then-"
Jack interrupted and went "Whoa whoa whoa, hang on, did you say that incest was legal? Like, seriously having sex with family members?"
Twilight, somewhat baffled, confirmed "Um.... yeah, incest is perfectly fine so long as it's consensual, was it not legal back in your world? Geez, what's the deal with your species? They sound like total prudes! In Equestria you can even marry a family member if you like! I'm not ashamed to say that I'm married to my brother, he's just lucky that I'm willing to share him with his second wife who happened to look after me when I was a foal. If something as common as some casual incest was considered wrong where you're from then this may be a bit of a bumpy ride, Equestria is very liberal when it comes to the legality of sex"
Jack allowed the information to soak in before Twilight continued "Moving on, we have sex with children, rare but perfectly fine-"
Jack had to interject again and said "Really?! Sex with children?!"
Twilight came back with "Calm down! There are limits to it of course! You can't have sex with a child unless they have a cutie mark and like I said, it's extremely rare that any pony wants to have sex with a child... though it's rumored that Princess Luna has a little group of colts and fillies that she plays with before she enters the dream realm at night"
Jack's eyes went wide, the night princess herself? Licking out little fillies and asking colts to stick their dicks in her ass? Whether the rumor was true or not, Jack had to admit that the visual imagery of the scene in his head wasn't completely unwelcome if his arousal was anything to go by... though one little detail did catch his attention and he was quick to say "Hang on, you didn't mention consent that time..."
Twilight blushed and, somewhat embarrassed, she went "Ah... s-sorry! It's just that this kind of stuff is common knowledge so it didn't enter my mind! Don't worry though, all forms of sex need consent, you can't just pin some pony down in the middle of the street and fuck them whenever you're in the mood, you gotta wine'em, dine'em, then you can rock their world! Shall we continue?" Jack nodded and allowed Twilight to proceed, the rules of sex her were very interesting. Twilight carried on "OK... so rape is illegal obviously and so is necrophilia... "
Twilight's face dropped somewhat, she wasn't sad or disgusted in any sense she just seemed slightly irritated as she closed the book and finished "Yeah, bestiality is fine too I guess. If that's what floats your boat then sure, knock yourself out even if it's..... well, whatever"
Jack raised an eyebrow, rather than being shocked at the revelation that bestiality was perfectly legal, he was more confused by Twilight's reaction and asked "What's with the attitude? Not a fan of animal stuff?"
Twilight sighed and said "No it's not that it's just... well it's complicated, I don't engage in the activity of course and the main reason is that... yes it's technically legal but it's not exactly the "done thing" y'know? It's generally frowned upon in pony society which may seem odd considering our stance on interspecies relationships but any pony who feels lust towards animals... they have to kind of keep it a secret if they want to enjoy it and not be shunned and treated like dirt. Clear?"
Jack absorbed and processed the information in his mind before simply nodding, satisfied that he now knew the rules regarding sex and relationships, even if they were almost completely opposite from the ones he had known in his previous life. As Jack was about to leave, he heard a small voice behind him go "Hey Jack... so, you and Twilight were talking about sex huh?"
Jck turned around to see Spike, who was looking more bashful than ever, as he went "Were you talking to her about it because you wanna bang her or are you seeing someone at the moment?"
Jack had always suspected that the reason Spike went red in the face every time he visited Twilight was because he was gay, still in the closet, promiscuous and also had a slight crush on him. Jack chuckled and said "Neither, why do you ask Spike? You interested?"
Spike went so red that he was beginning to resemble an apple, sweat coated his face as he tried desperately to speak, only for his voice to die in his throat. Jack smiled as he decided to stop teasing the poor young drake by going "Spike, I can't remember the last time someone helped me get some... physical relief, you wanna go up to the bed room so you can help me out? I'm not exactly looking for a boyfriend... but I'd be lying if I said I don't want you to suck my cock... you game?"
Spike just nodded and went "Uh-huh" shortly before following Jack up the stairs, so eager to finally get his first taste of Jack's dick that he figured that everything he had wanted to say and more would be said best by simply demonstrating his oral skills to this handsome human. Jack was feeling very pent up due to not having the balls to ask Twilight about things sooner, he had seen plenty of attractive mares and stallions that he wouldn't have minded having a roll in the hay with, though Fluttershy was the only one he felt like he could pursue a relationship with, the only one where he felt like he could make love to her in an emotional, spiritual and sensual connection of flesh rather than just a casual hook up, if only he knew that Fluttershy felt the same way... but they were both too nervous to find out if their love was reciprocated or unrequited... for now at least.
As soon as Jack reached the bed he sat down and began unbuckling his belt, his excited boner aching to be released and tended to, his full and heavy nuts ready to be emptied as soon as possible. Spike wasn't what Jack considered to be handsome, he wasn't unattractive at all, it's just that his boyish demeanor and slender frame made him seem more like a cute femboy rather than just a young dragon who preferred the company of a stallion... however, Spike was the only dragon around so for all Jack knew about dragons, Spike might be butch for his species. Spike walked in and salivated, he knew it would look different but it was no less enticing, Jack was sat there with his pants and underwear around his ankles with a throbbing hard-on just waiting to be serviced.
Despite how much Spike wanted this and how much Jack was willing to indulge in his fantasy, they both knew that this wouldn't become a friends with benefits situation, this definitely felt like the kind of thing that would happen once just for the experience, after this was over they'd both go back to ponies and try their luck with them instead. Spike approached and dropped to his knees, licking his lips and slowly bringing himself closer to the object of his desires, he tried not to overthink it but his trepidation made him cautious, he'd sucked off a couple of stallions in the past but didn't know if Jack would enjoy the same kind of treatment considering he was the one and only human.
Jack simply waited patiently, looking at Spike in admiration and wondering what a dragon dick looked like until he felt the young drake take hold of his boner, stroking up and down until he finally found the courage to lean in and start sucking on Jack's nut sack. Jack sighed in satisfaction and went "Paying attention to the balls first huh? Something tells me you're not exactly a rookie Spike"
Spike smiled as much as he was able and carried on, making sure to lavish every single crease and crevice of Jack's cum factory before seamlessly moving on to give the same treatment to the other one, subtly pumping his boner a little bit faster to keep things interesting. Pre began to leak steadily from the tip of Jack's member, it dawned on him that in his slight desperation to finally get some action he hadn't factored in just how fucking weird the situation was and what the ramifications were, his first sexual experience in Equestria and it was as simple as letting an effeminate gay dragon go down on him... oh well, any port in a storm! Jack knew he was stuck in Equestria so rather than be surprised at everything, just go with the flow and see what happens!
Jack continued to make small moans of enjoyment as Spike cupped his heavy human fuck sacks and started dragging his long tongue up his shaft until reaching the tip, instantly taking the head between his lips and swirling his tongue around while applying some gentle suction. Jack groaned and exclaimed "Damn Spike, how many cocks have you been sucking in secret to get this good? I'm willing to bet stallions don't last very long whenever you treat them to your magnificent mouth right?"
It was a rhetorical question, so Spike remained silent and concentrated all his efforts on pleasing Jack, showing off that he knew how to make a guy blow his load, he wanted Jack to cum as hard as possible and so he decided to kick things up a gear. Jack was getting closer and closer to the edge, he knew that he'd end up busting a nut pretty soon and that was made certain when Spike effortlessly slid half of Jack's stiff prick into his mouth and began bobbing his head up and down, softly squeezing his churning cum tanks as he did so. Jack gasped before he grunted "Ooh fuck..." as he placed his hand on Spike's head on reflex, Spike leaned into his touch and responded by going further and sinking Jack's dong deeper into his gullet, still being sure to keep sucking and thrashing his tongue around, he could tell Jack was close.
Jack breathed heavily as he said "Spike...I'm like, ten seconds way from cumming, I'm not gonna be able to hold back much longer at this rate..."
Spike decided to pull out all the stops to make sure Jack had a powerful orgasm, on top of cupping his balls, Spike reached past them to tease Jack's ring but more importantly, he effortlessly slipped the rest of Jack's member into his mouth, his lips pressed right up against his crotch. Jack just grasped onto Spike's head and shouted "Oohh SHIT!"
Spike emptied his nuts onto the floor below as Jack climaxed, sending thick heavy ropes of jizz flying from his tip and directly into Spike's stomach, Spike stayed still until Jack had been fully drained. Once Jack's cock fell from Spike's lips, Spike smiled and said "You like?"
Jack, still catching his breath after such an exhausting ordeal, went "Whew, I liked very much! How much mischief have you been getting up to and still not coming out of the closet to everyone?"
Spike pondered for a second before shrugging and going "I dunno, I've lost count at this point. I will come out when I'm ready but now is not that time, you should probably go before Twilight gets curious... though if ever you wanna find out how nice it feels to fuck my ass, you know where to find me, right stud?"
Jack chuckled and asked "More of a receiver than a giver huh?"
Spike rolled his eyes and said "It's all the same to me, sex is sex dude!" Jack laughed and pulled his pants and underwear back up, buckling his belt and promptly left feeling refreshed, rejuvenated and ready to bang a pony if he felt like it, confident in the knowledge that it was perfectly acceptable and legal for him to do so despite being a human being.
It had been a while since Jack's encounter with Spike and he didn't know whether it was Spike or Twilight but news had spread throughout the town that Jack was single and was now ready to mingle now that he knew and was comfortable with the fact that he could have a girlfriend or boyfriend without feeling like he was committing some kind of crime against nature, not to mention the fact that there were plenty of ponies who were curious about what kind of tool was lurking between his legs.
There was a lot of hushed whispering in town about who among them would have the guts to actually approach Jack and get to know him more intimately, not necessarily in a relationship sense but at the very least in a... hanky panky sort of sense. Most of the mares were intimidated because he was the sum total of a species that didn't exist anywhere else and their fear of the unknown cancelled out their intrigue, homosexual stallions steered clear because they were either still in the closet or weren't as fascinated by him as some other ponies were. However... there did come a day when one pony finally mustered up the strength to talk to him and offer a naughty little proposition, it was Lyra.
Jack was already well acquainted with Lyra and her girlfriend, Bon Bon, due to the fact that the three of them shared some common ground in their sexuality. Jack, Lyra and Bon Bon were the three most well-known bisexuals in Ponyville and that gave them something to talk about when Jack had first been settling in and getting used to the pony way of life. Jack was walking down the street when Lyra practically galloped over and excitedly said "Hi Jack! How's to going? It's been a while since Bon Bon and I have seen you around town"
Jack smiled and replied "Oh hey Lyra, not much going on with me at the moment, the newly refurbished "Sofas, Quills and Beds" shop has had such a big boost in business recently that I'm not needed as much so I've got more free time to actually spend the money I've saved up. How about you and Bon Bon? You two got anything going on recently?"
Lyra blushed and looked away awkwardly, rubbing the back of her neck with a hoof as she went "Well... a-actually that's part of the r-reason I came over here to t-talk to you Jack! You see Bon Bon and I were... were thinking of s-spicing up our... our s-s-sex life a little and... we were just wondering, y'know... if you're like... interested, since you're now available to be intimate with ponies... that you might... y'know?" Lyra was beating about the bush a little but Jack got the basic gist of what she was trying to say, he was being asked to be in a threesome!
Jack, very surprised, asked "Really? You and Bon Bon... and me?"
Lyra, clearly still too embarrassed to speak, just nodded. Jack mulled it over in his head, a threesome involving two girls was your classic fantasy scenario and it's not like he would be doing it with complete strangers, not to mention the fact that he wasn't really getting a lot of action and still didn't have the balls to stop being such a pussy and just ask Fluttershy out on a date, was there a downside to this? Lyra was left stood there sweating bullets for about two minutes before Jack went "Yeah, alright then. Want me to come over right now?"
Lyra just gasped loud enough to rival even Pinkie Pie's gasps of surprise, grabbed Jack by the hand and started dragging him to where she and Bon Bon lived going "Yes! Come on Jack! We're almost there!" Upon arriving at the house, she threw open the door and shouted out "Bon Bon! Bon Bon! Look! Jack says he's willing to get freaky with us!"
Bon Bon was stood in the hallway smirking as she went "Oh, so he is? Well then..." Bon Bon pointed at a door across the room and continued "Bed room is that way, won't you join my girlfriend and I for some fun?"
Jack just nodded, his cock already semi-erect from the very suggestion of sex as he followed Bon Bon and Lyra into their bed room. Jack started to get undressed, it had been a while since he'd been able to take his clothes off in preparation for sex instead of a shower, though what caught his attention was when Lyra levitated a red ball gag into her own mouth and fastened it tightly around her head so that she wouldn't be able to expel it, looks like there was going to be a little more kink factor to this threesome than Jack had originally realized.
Clothes had been an issue when he first arrived in Equestria, he had explained why nudity was viewed differently where he came from but ponies still didn't understand what was quite so taboo about it and had repeatedly stated that every creature walked around naked and only wore clothes for specific occasions and that he should do the same. Jack had, obviously, refused and kept to the "human way" of being constantly dressed unless bathing or, in this instance, fucking.
Bon Bon lied on her back on the bed and went "Hope you don't mind Jack but for now I'm just gonna watch you fuck my girlfriend and I want a good view!" Lyra got on the bed and stood over Bon Bon before spreading her hind legs and lifting her tail, silently waiting for Jack to approach her from behind and quickly penetrate her perfect pony pussy. Bon Bon carried on enticing Jack as she said "My girlfriend's pussy looks real good doesn't it?"
As if Jack wasn't hard enough, Bon Bon leaned up and applied a long slow lick to Lyra's folds, causing the mint mare to whimper before Bon Bon pulled away and licked her lips saying "Mmm... sure tastes good, though I think you'd be the best judge of how great her pussy feels!" Jack instantly made his way over, getting on his knees and gripping onto Lyra's fat flanks in preparation to accept the extremely seductive invitation to claim her cunny that Bon Bon was extending out to him. Lyra shuddered as she felt Jack's strong hands grip onto her bottom, small moans emanated from the back of her throat which were only more muffled by the ball gag in her mouth, Bon Bon waited anxiously to see Jack finally stick his fat human dick into her girlfriend's moist cunt.
Jack shuffled forward and made sure he didn't accidentally kneel on one of Bon Bon's legs or her face, slowly bringing his tip to Lyra's hot entrance before pressing forward and, without any difficulty, eased his entire erection into her soft and silky love tunnel. As Jack hissed through his teeth upon his hips pressing up against Lyra's buttocks, he took a few seconds to really immerse himself in the feeling of her body, the fit was surprisingly... comfortable was the best word for it, like it was made to fit and yet, the way her walls gripped his member and squeezed it hard added a certain element of tightness as well. Lyra was in much the same situation, never had her marehood felt so completely and deliciously full before, her experience with stallion cocks was that some were too big, or long but lacking in girth or any other myriad of combinations that never truly satisfied her... but this human? Fuck yeah.
One dragon, two ponies, three...
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.
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?
That was a question to be answered another day because Applebloom had moved out of the way, prompting Scootaloo to stop eating out Sweetie Belle's ass and stop playing with herself so she could get Jack's slicked up dick into her equally slicked up filly folds. Scootaloo stepped forward and asked "So Jack, you're the lucky guy I'm gonna ride once I sink you into my fuck hole but I like to think I'm a nice and accommodating kind of gal! So what way shall I face? Away or towards?"
Jack thought for a few seconds, Scootaloo seemed like the domineering type and, in his experience at least, having the girl facing him seemed to heighten the domination feel for both him and his partner. Looked like Scootaloo would be riding cowgirl, which was quite ironic considering she was friends with Applebloom, though Applebloom was more of a southern belle, which was also ironic considering she was friends with Sweetie Belle! Realizing that he was getting sidetracked in his own mind, Jack returned his attention to the filly who was patiently waiting to enjoy some human dick. Mind made up, Jack simply replied "towards"
Scootaloo clambered onto Jack's lap and lowered her hips, carefully making sure that his prick would be aimed straight at her pony pussy. Jack held his cock still so that it wouldn't accidentally slip away from its intended target of a moist barely legal cunt, Scootaloo biting her mouth lips when the head made contact with her excited pussy lips, for the next few moments, this big and masculine human was hers to please... for the purpose of helping him, obviously, she wasn't being a horny slut who found Jack sexually attractive! She was just helping him! It was just a coincidence that assisting him would involve draining his nuts dry! The tip of Jack's cock popped in and Scootaloo began to descend, lightly gasping "Whew... you're pretty big huh? Very big indeed..."
Jack grunted as more and more of his member was claimed by Scootaloo's quivering love tunnel, he was two thirds of the way in when suddenly he hit a barrier that halted Scootaloo's progress, her cervix. Jack wasn't surprised, their size difference pretty much guaranteed that he could only get so far inside her before reaching that point, what did surprise him however was that instead of immediately accepting it and making the most of what she could do on top of him, Scootaloo took in a deep breath and kept at it, mashing her cooch on his length to see if she could coax her cervix into opening up enough to let him penetrate just so that she could take the whole thing inside her.
Jack, concerned that she might injure herself or cause some kind of discomfort, insisted "Scootaloo, you don't have to do this, it's OK if y-"
Scootaloo interrupted "No! I'm doing this! If a teenage stallion can get his over-sized wang inside my snatch then I can damn well fit a grown up human! I'm not giving up until I'm fully sat on your lap! I can take it!"
While Scootaloo continued ramming herself down on Jack's dong, Sweetie Belle, who was still in position from where Scootaloo had been rimming her, called out to Applebloom "Hey Applebloom! You mind picking up where Scoots left off? Gotta make sure my booty is ready!" Applebloom smirked and took her place behind Sweetie Belle before continuing the oral assault on Sweetie's pucker that Scootaloo started. Scootaloo's cervix eventually conceded defeat as it was forcibly stretched open, finally wide enough for Jack's cock to push its way in and experience its first time feeling pleasure beyond the pussy.
Jack's muscles tensed as his dick was gripped feircely by an opening that was only ever meant to open to push out a baby, he opened his scrunched eyes and saw that Scootaloo had a similar expression on her own face, gritted teeth and what looked like very extreme displeasure. Jack went "Holy shit... Scootaloo, are you alright? Doesn't that hurt?"
Scootaloo replied "Aah... yeah, it does a little... but don't worry! I'm fine I swear! In fact... well, I know this might sound kind of weird and confusing but... I actually kinda like sex more when it's... painful, Rainbow Dash tried to explain it to me but I don't really get it, all I know is that if something aches or stings or whatever... it feels way better!" Incredible, Jack never would have guessed that Scootaloo had a pain kink, she must have found that out thanks to the "over-sized wangs" of those teenage stallions she had mentioned earlier, that was his theory. Jack's thoughts of how Scootaloo had developed a penchant for enjoying the kind of sex that would hurt her were suddenly cast aside as he felt Scootaloo continue her downward descent and, as promised, she only stopped when she was settled down on his lap with his cock completely hidden from view inside her frail little body... time for a ride.
Jack considered it lucky that he couldn't breed a pony because the second that Scootaloo started bouncing up and down, her cute gasps of elation, the moist warm grip of her walls milking him for his load, the feeling of being balls deep inside a filly for the first time, all of it combined made Jack feel like he could easily bust a nut if he didn't hold back and with how he was literally inside Scootaloo's baby chamber, he could have easily delivered a full and fertile payload into her foal factory. Needless to say, penetrating her cervix was interesting, he didn't know if she'd had her cervix penetrated before but it was certainly a new experience for him and strangely enough, he found that although the cervix was tighter and warmer to fuck, it didn't increase the pleasure all that much. It was slightly better for sure but it was nearly insignificant.
For Scootaloo however, it was very significant indeed. Having a human cock batter its way through an opening that was not all built for sex was an electrifying experience, true that the butt wasn't exactly designed for sexy times and neither was the mouth but at least those were openings where, with a curious mind and some practice, could easily become a regular favorite between two fuck buddies. The actual cervix however? That was like claiming a second pussy within an already existing pussy and it wasn't just the perversion of the idea that turned Scootaloo on, it was the uncomfortable fullness she felt that really got her going.
Both Jack and Scootaloo were made a myriad of noises, humming, grunting, gasping, all while the pace of the sex remained steady and consistent, neither of them were willing to rush the experience. Minutes passed and they were both getting very hot and sweaty, Jack's orgasm was coming but Scootaloo was getting impatient and so she decided that if she was ever gonna earn Jack's seed, she needed to up the ante. Scootaloo went from bouncing up and down to smoothly rolling her hips as fluidly as she could manage, going around in circles so that she could stimulate Jack's tool from every angle instead of just pumping. What was so wonderful about Scootaloo's new movement technique is that it also forced her to feel Jack's rock hard bitch breaker to rub against every single nook and cranny of her sensitive insides as well.
Jack groaned at the new sensations he was being subjected to, his climax was approaching faster than ever, though the thing that really brought him to the edge was when Scootaloo looked him dead in the eyes and simply whispered "You gonna cum? Do it inside big boy..." Scootaloo knew he couldn't impregnate her but a girl can dream.
Jack let out a guttural cry as he grasped Scootaloo's hips, holding her still as his nuts tightened before he sent thick heavy ropes of jizz directly into her womb, an action that triggered Scootaloo's own orgasm, her cunt twitching and convulsing around Jack's pulsating manhood as he continued to ejaculate, flooding Scootaloo's uterus with fresh hot spunk. Eventually their climaxes ended and they were left wheezing from just how intensely they had brought about their finishes. Once Scootaloo had regained her energy she lifted herself off of Jack's dick... or at the very least she attempted to.
Scootaloo was barely halfway up Jack's erection when the same obstacle that had stopped her sinking herself down was now in the way of her lifting herself up, her cervix. It seemed that her cervix was just as unwilling to let go of Jack as it was to let him enter in the first place, not to mention that the ridge of his mushroom-shaped tip made pulling out more of a challenge as it kept him locked in place like a cork in a bottle. Obviously, neither of them were too keen on being stuck together for too long, especially Jack who still had one last filly to fuck silly before he went to try and court the mare of his dreams, Fluttershy. Scootaloo continued to try and wrench herself off of Jack with not much success despite how hard she was tugging, she just wasn't strong enough and so Jack had to intervene lest he remain trapped in Scootaloo's cunt.
Jack's first step was to roll them over so that he was on top, that way he would have more momentum when trying to pull out, his second step was to hold Scootaloo down so she wouldn't move or end up just being dragged along the ground when he tried to pull out, time to try it out. Jack heaved his hips backwards and when he reached the point when Scootaloo's cervix wouldn't allow him to pull out any further, he kept going, gradually increasing the strength with which he pulled while Scootaloo splayed her legs wide open in the hope that would make the whole process easier. Unfortunately, Applebloom and Sweetie Belle were too caught up in their own activity to notice any kind of problem.
It was when Jack felt he couldn't possibly pull any harder that the battle was won, Scootaloo's cervix opened up just enough that he could remove himself and he soon found himself launching backwards and roughly removing his still hard dong from Scootaloo's cunny. They both breathed a sigh of relief, with Scootaloo taking a well deserved rest while Jack got back into position ready to take on Sweetie Belle.
Scootaloo humphed and went "Hey guys, in case you didn't notice while you were busy not helping Jack rip his fat human schlong out of my nethers, he's ready for round three already! Pay attention!"
Applebloom pulled away from Sweetie's ass crack, having heard Scootaloo's words and blushing slightly at having gotten so lost in lubricating her friend's bottom, with Sweetie also smiling apologetically at having been so distracted when her back door was being tended to. At this point, Jack was almost certain that this method of making him confident enough to approach Fluttershy may have been a lie and that they had an ulterior motive of just having some hanky panky, though that wasn't to say he was complaining and he did feel like he should probably man up and ask Fluttershy out on a date, so it kinda worked!
Applebloom and Scootaloo stood aside while Sweetie Belle sauntered seductively over to Jack with lidded eyes as she giggled and said "Applebloom had trouble getting you down her throat and Scootaloo had trouble getting you in her pussy huh stud? Well I'm not like those two, I haven't yet come across a guy of any length or girth who had a difficult time sliding their hard, pulsating erections into my sexy rump. Also, I'm not as inconsiderate as my friends either, I'm gonna take my time with you, keep things nice and slow so I can get you off with my hind quarters gradually to make you cum really really fucking hard"
Damn, either Sweetie Belle was good at dirty talk or she'd had enough anal sex that she could feel this cocky about it, even if her friends clearly weren't too impressed that she considered herself so superior when it came to sex. Sweetie Belle continued "You're probably wondering what my kink is huh? Sorry to say that I don't really have a kink, at least not in the same way my friends do, does butt stuff count? Anyway, I think I've made you wait long enough Jack, don't want you losing your boner after all do we? Just stay put and I'll take real good care of you, make you feel good with my ass so you can cum... daddy"
Holy shit, Sweetie Belle was really making Jack feel hot under the collar and she wasn't even doing anything yet, she was just talking! Even Applebloom and Scootaloo were visibly hot and bothered by the way Sweetie Belle was talking, though it seemed they were both too tired to play around with each other, sex did take a surprising amount of energy. Sweetie Belle turned away and started backing up, slowly moving her cute little butt closer and closer to Jack's face before parking herself down on his chest before going "Alright big guy, first things first, if you wanna earn the right to stick your fat dick up my rear then you gotta show it the respect it deserves! I'm not asking for much, just some light worship m'kay? If you do a good enough job I promise not to tease you for too much longer, so get started and treat my backside real nice!"
Sweetie Belle shook her ass a bit right in front of Jack's face, then patiently waited for him to do what he thought would be adequate praise for the generous gift of allowing him the joy of some sensual anal sex. Jack grasped onto her soft buttocks and very gently squeezed and massaged the tender flesh, making sure that he paused every few seconds to plant a kiss against the smooth skin. Sweetie Belle hummed in adoration and said "Oohh yeah... now that's what I'm talking about..." as she lit up her horn and began to magically and tenderly fondle Jack's nuts, she paused periodically to give his balls the slightest of squeezes.
A minute or so of mutual groping went by before Sweetie Belle went "OK, you're off to a good start but now it's time to get a bit more intense and actually pay attention to the hole you'll be cramming yourself into, I suggest you up the ante if you wanna truly cherish my caboose and prove that you deserve to pound me, to stretch out and gape my ponut with your thick, hard, pulsing and positively enormous human cock..."
Applebloom and Scootaloo acknowledged that despite how tired they were, they couldn't ignore the burning in their loins from hearing their friend talk so dirty and decided to start making out with each other while using a hoof to rub away at their own moist filly cunts.
Jack ceased his actions on Sweetie's cheeks so that he could spread them open and get a good look at her pucker, wondering how best to approach showing Sweetie Belle that he was truly grateful and felt very lucky that she was allowing him to do this, not that he was under any delusion that she'd deny him the opportunity if he messed up of course. Jack figured that if he was holding onto Sweetie's glutes, then his only real option was to tend to her ring with his mouth and so, without hesitation, he leaned forward and gave a somewhat passionate kiss.
Initially Sweetie's ass muscles tensed, her body recoiling on reflex at the unexpected sensation of something touching her in such a private area, though as Jack continued to apply more and more sexual kisses, her body began to relax and eventually register the odd feeling as pleasure, small shudders and gasps escaping Sweetie Belle each time. Once she was acclimatised to the feeling, she moved her magic away from his pendulous cum tanks and onto his cock, squeezing his stiff meat from the base of his shaft the tip of his head but not yet stroking it, Jack would have to do more than kissing if he wanted her to actually jerk him off with her magic instead of just massage his raging erection.
Jack grunted at feeling every inch of his length being so mercilessly teased, Sweetie Belle was really playing the long game here and she was certainly gonna make Jack work for the right to plumb her depths, well if she wanted him to put some effort it then he'd gladly do his best. Jack decided to stop kissing the entrance to her bottom and instead do what she had asked her friends to do, pressing his warm and wet tongue against her plot hole and licking it firmly, occasionally swirling his tongue around in circles to thoroughly moisten her tush.
Sweetie Belle let out a moan, going "Ooohhh fuck yeeaaah..." as she pushed back on Jack's face and increased the intensity at which she was caressing Jack's member but still refusing to pump his dick despite the pre-cum he was producing, clearly showcasing his need for more direct stimulation that Sweetie Belle carelessly continued to ignore. Jack didn't mind taking things slowly to create excitement but this was getting ridiculous, after being polite and gracious enough to continue licking for another minute, Jack pushed his tongue inside her rear and started thrusting it in and out in the hope that Sweetie Belle would return the favor in kind by whacking him off with her magic.
Sweetie Belle bit her lip to hold back what would have been very depraved, whorish and slutty unfeminine grunts of pleasure and finally added some movement to her handling of Jack's cock... very small and subtle up and down movements that barely made a difference other than prolonging the torture, not quite the magic hand job... hoof job? Whatever... either way, it wasn't quite what Jack had hoped for, he wanted Sweetie Belle to do it properly! He knew that anal sex was the end goal but why edge him like this? It was just too cruel! Sweetie began to grind back roughly on Jack's face, though she was robbed of that ability when Jack pulled his face back and brought two fingers to her back door, time to really put her to the test and kick it up a gear.
Sweetie Belle yelped in surprise as she felt Jack plunge his digits into her bottom and start to savagely ram them in and out. Once the surprise faded away and turned to pleasure, Sweetie Belle smirked and finally started using her magic to stroke the entire length of his dick like there was no tomorrow, milking his man meat like a cum hungry machine. Scootaloo and Applebloom had moved on from simple self pleasure at this point, they were still kissing but they were now lying on the ground and rubbing their pussies against one another like it was a casual thing. Both Jack and Sweetie Belle could feel the familiar ache of a building climax, something which they somewhat wanted to avoid considering that they wanted to save their respective orgasms for the main event.
Sweetie shuffled forward, making Jack retract his fingers which in turn made Sweetie cease magically pumping his cock. With a hot, sweaty and slightly frazzled look, Sweetie turned to look at Jack and went "Alright... we played a little rough there huh? Naughty boy, so pent up that you had to force little ol' me to hurry things along? You're such an impatient dirty boy... tell you what, if you're good and hold on just a little bit longer, then I'll forgive you and finally give you the treat that you so desperately want from me...... do you think you can do that for mommy? Just behave and I promise you won't regret it!"
Whoa, Sweetie had turned up the horny dial to eleven, had Rarity taught all of this dirty talk and seductiveness? If not then talks had to be had. Nevertheless, Jack just dumbly nodded and gave Sweetie the go ahead to do what, hopefully, would be the final bit of prep before the real fun. Sweetie kept her magic hold on Jack's angrily throbbing rod and made her way down his body until she was stood over his lap with his painfully erect fuck pole stood proud directly behind her plump ass. Sweetie Belle looked back over her shoulder with a sultry expression on her face and then used her magic to make Jack's love log pat her thick cheeks, the light slapping noise and view of her butt jiggling making Jack all the more eager to sink himself into the young filly's bottom.
Sweetie Belle quickly moved on and held Jack's long member steady as she backed up and wedged it into her crack, shaking her hips from side to side a little before gyrating her rear end up and down at her best attempt at delivering a very satisfying butt job, she didn't disappoint. Jack was fighting the urge to pin this bitch down and rail her, Sweetie Belle could see Jack struggling and said "OK big guy, calm down and cool your jets there! I've had my fun and plenty of it but I think it's about time we get to the bit that we've both been waiting for... the anal sex"
At last, Sweetie had done a stellar job at making him riled up and keeping his boner hard, now all that was left was some awesome kinky butt sex followed by more awesome kinky butt sex until they both came. Scootaloo and Applebloom were lying nearby, unable to pay attention to what was about to transpire as they breathed heavily, panting as they tried to relax after having made each other squirt in orgasm.
As Sweetie Belle got into position, Jack briefly felt a slight wave of regret at not having taken the time to slap Sweetie's fat flanks, if she was really into butt stuff then a firm spanking would've easily made her more wet than she already was... then again, it had taken them long enough to get to this point so he wasn't about to suggest it now, maybe he could do it afterwards as punishment for teasing him so much. Sweetie slowly moved downwards, using her magic to guide Jack's dick to her pucker, she didn't show it but she was looking forward to banging her first human as much as Jack was looking forward to banging his first pony posterior, the build up had been slow but it would be worth it.
Jack also reflected on how thus far, his only experience with his own gender was a blow job from Spike, he hadn't had sex with any guys yet! He never considered himself as someone who could really have a real relationship with a guy beyond being an occasional fuck buddy but somehow he hadn't attracted the attention of any stallions. Jack realized he was getting lost in thought and was only brought back to his senses when he felt the head of his cock press against Sweetie's juicy ass hole. Sweetie went "Mmmm... we have contact, hope you're ready for me..."
Jack had been ready for her ever since he'd placed a kiss on the ponut he was about to penetrate and Sweetie knew it, luckily she decided that the time for dragging things out even longer was gone and kept going, steadily applying more and more pressure to get Jack into her backside. It was maybe only two seconds at most before the tip of Jack's cock almost effortlessly slipped inside Sweetie Belle's ring, both of them letting out a sigh of satisfaction as they finally crossed the threshold. Sweetie hummed before going "Now, normally I would have you pull out and push back in a few times just to make sure that you can glide in as comfortably as possible... though considering that we are obviously both rearing to go... shall I just ease myself down on your prick?"
Jack grunted and replied "Yeah... I want to feel that ass wrapped around my tool as soon as I can, so you just sit right down on it... you bitch..."
Sweetie Belle chuckled and cut off her magic, confident that now Jack was actually in she could do the rest without holding him in place. Sweetie pushed herself down, breathing deeply as she felt the first inch of Jack's perfect erection sink into her tight little filly butt, stopping to allow her body time to relax and get used to such a phallic intruder. Jack similarly groaned in the back of his throat, he was only one inch in and he could already tell that, once hilted, it was going to be a snug fit. After a few seconds, Sweetie took a deep breath in and let it out as she descended further until stopping when just a little over half of Jack's meat was packed into her rump, again having to stop and let her body acclimatize to the feeling of being filled so suddenly with human cock.
Both of them were still making only the faintest noises of pleasure as they both held themselves back until the actual fucking really started, it was at this point that Applebloom and Scootaloo had recovered from their fun and were watching the spectacle play out with mild interest to see if Sweetie's butt was as great at taking dick as she had first claimed. Another few seconds and Sweetie repeated the process until both she and Jack let out a mixture of satisfied sighs and moans as he was finally balls deep inside Sweetie's rear, she was fully sat down on his lap with her cheeks pressed against him and his fuck pole nestled firmly in the warm walls of her insides, hugging his bottomed out boner perfectly.
Sweetie Belle rose until just the tip of Jack's member was left inside her, then slammed herself back down all the way to the base, Jack grunted while she let out a small gasp. Sweetie rose again, this time she left half of Jack's member still inside before slamming back down to the hilt. It was then and only then, that Sweeite Belle finally began to bounce up and down, riding Jack like there was no tomorrow, at last they were having the anal sex that she had promised and the ecstasy was insane. The pleasure that rippled through their bodies was immeasurable, so much so that they failed to make any noise, there were no lewd or sexual wails of two bodies connecting there were just the same tiny gasps, grunts and groans that they had been making all along.
Despite the pleasure however, it seemed that their orgasms weren't arriving as quickly as before, Jack was building up slowly due to having already cum inside Scootaloo and then the travesty of having been edged by Sweetie Belle up until that point and Sweetie Belle had also been edging herself throughout so her orgasm was climbing just as slowly as Jack's was... meaning the anal sex would last longer. Applebloom and Scootaloo watched and they jealously had to admit to themselves that Sweetie Belle's bragging about the ease of anal was well founded, there was no troublesome barrier like in Scootaloo's pussy and there wasn't any need for additional assistance like Applebloom's deepthroat attempt, it was just simple butt fucking.
Jack had initially enjoyed the way Sweetie Belle built the anticipation, then about halfway through he got impatient and her constant habit of prolonging things even more became irritating... though now that he could feel just what Sweetie Belle had managed to accomplish by playing hard to get, he was glad that she had kept it going for as long as she did because this was possibly the best anal sex he had ever had in his life, so enduring Sweetie Belle's sexual torture was well worth it.
Sweetie Belle was in very much the same boat, most colts were constantly horny and didn't have the courtesy to be patient and let Sweetie Belle have her fun with them, often becoming so annoyed that Sweetie Belle had no choice but to cut things short and bend over so that they could mount her, with Jack however? Either grown-ups were more patient or it was a human thing but either way, she was able to properly enjoy herself thanks to Jack letting her do her thing first.
Scootaloo and Applebloom, still very much tuckered out, were content to watch and didn't really have the energy to even become aroused, let alone enjoy even more sex just between the two of them... not that all of this was for the sake of enjoyment, they were helping Jack build up the confidence to date Fluttershy! They weren't just being sluts, obviously. Sweetie Belle had talked dirty plenty throughout the process and yet, apart from some sex noises, she remained completely silent for the actual sex itself and just focused on bouncing her fat little bottom up and down on Jack's cock as it continued to throb aggressively in her ass.
Jack grit his teeth, scrunched his eyes and dug his fingers into the grass, he was reaching his peak and the ache of orgasm told him that he was about to have a very draining and almost painfully strong ejaculation. Never before had he been so wound up, now the coiled spring of climax inside him was about to break and his nuts were about to bust, if this filly wanted a filling then she was about to get it big time. Try as he might, Jack could no longer stave off his inevitable finish, he threw his head back and practically screamed as his balls tightened, sending a tsunami of spunk to flood Sweetie Belle's hot insides.
Sweetie Belle shuddered as she felt the pervading warmth of Jack's jizz filling her booty but kept riding him through every thick and heavy rope of his cream that was pumped into her rear end, making sure that she milked every last drop that his fuck sacks had to offer with her ass hole. It was only when Jack had given all he could give that Sweetie Belle planted herself down firmly on his lap and gave nothing more than an adorable squeak as fluids gushed from her cunt, shivering as the rippling walls of her ass subtly reminded her that there were still several inches of semi-erect human cock up her butt. With one final burst of filly cum, Sweetie Belle gave a big sigh as she went full aheago face, heart shapes in her crossed eyes, blushing rosy face cheeks, a dopey grin and a lolling tongue, she had fucked herself silly on Jack's cock.
Both of them were panting, sweaty and exhausted. Sweetie Belle however, determined to always do her best, stayed in place and did some gentle grinding until Jack was so soft that she could barley feel him in her derriere anymore, at which point she got up and released him, his flaccid and fully sated member slipping elegantly from her ponut so that he could pull his underwear and pants back up. Before Sweetie Belle moved away, Jack smirked and kept the promise he had made to himself earlier and gave her a swift slap across the ass.
Sweetie Belle jumped with a yelp and went "Hey!"
Jack just chuckled and said "Sorry, couldn't resist!"
Sweetie rolled her eyes and went "Well, I suppose a girl deserves a little punishment for being so dirty and taking it up the butt.. anyway, it's all over now! What do you think? Did it help?"
Jack, having forgotten the whole idea, asked "Help? Help what?"
Applebloom tutted and went "Askin' Fluttershy out remember? Feel confident enough that you can satisfy her?"
A light bulb went off in Jack's head and he went "Oh! Oh yes definitely, I might go and ask her out right now! You guys were awesome!"
Scootaloo smugly proclaimed "Yeah, it's kind of our thing!"
As Jack walked off in the direction of Fluttershy's cottage, Applebloom turned to her fellow crusaders and said "Do y'all think we should tell him what we saw Fluttershy doin' the last time she was our foalsitter?"
Scootaloo pondered for a moment and replied "Nah, let it be a surprise! Besides, I'm sure Fluttershy doesn't want too many creatures knowing about it. What are your plans for today Sweetie Belle?"
Sweetie Belle went "Well I don't know about you but you guys got to cum a couple of times after you were done with Jack. Yeah, don't think I didn't notice you two lezzing up together! I'm gonna go into Ponyville and show myself off a little, see if any stallions or mares are interested, I'm one horny little filly and I'm ready for some hot pony action!"
Jack had decided to go into town and have a meal at sugar cube corner first before deciding to talk to Fluttershy, he was low on energy and needed something to keep him going for the rest of the day, especially if he ended up having sex with Fluttershy later that night despite the fact that he was pretty certain that she wouldn't even kiss on a first date. After feeling rested and rejuvenated, he started walking towards Fluttershy's cottage, enjoying the warmth of Celestia's sun and the cool breeze, taking in big breaths of clean fresh air. Equestria was way better than his previous world, it was practically a paradise if you ignored all the occasional evil villains that needed defeating or the constant pranks that were played by Pinkie, Rainbow Dash or Discord.
Upon reaching Fluttershy's home, Jack noticed something odd, her front door was already open and just slightly ajar, not a common occurrence for someone as paranoid as Fluttershy. Then there were two noises coming from inside the house, one was clearly some kind of large animals doing a series of growls and the other one was Fluttershy herself... she sounded distressed, was she being attacked somehow?! Without thinking, Jack pushed open the door to see if Fluttershy needed help... though the sight he was greeted with just flabbergasted him. There was an animal, a bear to be exact, and Fluttershy was indeed making some noise herself, though it was hardly surprising that she'd be making so much noise when a bear was absolutely railing her.
Jack stood there shell-shocked, he wasn't sure if he should be aroused or not, he could have been witnessing a rape here after all, though that theory crashed and burned when Fluttershy, having not noticed Jack's presence, shouted "Oh yes Harry! Breed me! You're such a big dirty bear aren't you? Yes you are! You like using my frail little pony body to relieve yourself don't you? Well do it! I want you to cum inside me!" Harry gave one final thrust and a large bear growl as he defiled Fluttershy's pussy with his baby batter shortly before pulling out and lumbering away, presumably to enjoy some food and water outside. Fluttershy sighed in relaxation, though her face turned bright crimson and her eyes went so wide that they looked like they'd pop right out of her skull when she turned around and saw Jack standing there.
There was a long moment of silence before Jack went "Uh......... hi?" Fluttershy squealed, flew towards Jack, pushed him out of the cottage and slammed the door in his face. Jack figured that he probably should have expected that kind of response at being caught in such a compromising position, he figured he should leave her alone for a bit and come back later when she was ready to face him. Fluttershy meanwhile was inside going into full panic attack mode, the human that she had a massive crush on had just seen her having sex with a bear! The embarrassment of it all, the shame, he probably thought she was a freak! She didn't stand a chance of being with him now that he had seen that! How could she ever face him again?! What if he told her friends?! Fluttershy scampered off to her bedroom to bury herself under the covers and just pretend that the outside world didn't exist for a while while she coped with her extreme anxiety at having been caught.
Weeks passed and every time Jack knocked on Fluttershy's door there had been no answer, he knew she was still in town because he'd caught glimpses of her when he was walking around but as soon as she noticed he was there, she'd turn tail and run away, giving no time for Jack to catch up with her literally or figuratively. For Jack, it was torture, he wanted to explain to Fluttershy how he felt about it, apologize for barging in, talk about it, ask her questions, have a real conversation from one friend to another and resolve the issue, maybe even get back on track with asking her out on a date... though he couldn't do that if Fluttershy wasn't ready to interact with him yet, she needed more time and so Jack did the respectful and responsible thing of just waiting.
Another week and a half went by before Jack's seemingly futile efforts to talk to Fluttershy bore fruit, he was once again knocking on the door of her cottage and surprisingly, it finally opened. Fluttershy seemed to have gotten over the initial shock of being caught enjoying bestiality by the human she was pining for and seemed calm in an almost scary way. Jack went "Hey Fluttershy... can I come in?"
Fluttershy nodded and said "Of course, forgive me for avoiding you recently but I imagine you can understand why, I wouldn't want you thinking I no longer consider you a friend.... I imagine you might want to talk about it though and I can't ignore it forever, so please come on in and I'll make us some tea and a couple of sandwiches to break the ice"
Well, that was as good a start as any, Jack walked in and made himself at home like he had always done during previous visits. Fluttershy fussed about in the kitchen before joining him with a plate of sandwiches and some tea, Fluttershy, being unusually serious went "OK Jack, let's not beat about the bush, this is a conversation we probably need to have. So you start and we'll... see how we feel, deal?"
Jack nodded and went "Deal...... so, I guess the first thing I should do is say sorry, I didn't mean to barge into your home like I did, the only reason I did was because when I heard animalistic growls and the sounds of you mewling as if in pain, I was concerned that you were in danger somehow rather than being intimate with... with a bear..."
Fluttershy returned the nod and replied "Understandable, though you shouldn't feel so sorry, a mare should make sure she locks her doors properly when she intends to indulge in the pleasures of the flesh, especially if she is sharing such carnal urges with a bear, carry on"
OK, this seemed to be progressing quite well, Jack continued by saying "I know that bestiality is legal and I'm completely alright with it, I don't think any less of you but I know that most ponies are ostracized if they are found out enjoying the activity... so I haven't told anyone about it"
Fluttershy took a sip of her tea before going "Thank you, I appreciate that you decided to keep what you saw a secret, anything else?"
Jack asked "Well.... I suppose my main question is, what's the appeal?"
Fluttershy calmly responded "Well, for me at least it's a... hmm, it's just... I've never really found ponies attractive... I don't even know what sexuality I would identify as even if I did find ponies attractive. I guess being around animals all my life made me develop... alternative romantic fixations... when it comes to animals I'm strictly heterosexual, though I'd be lying if I said I didn't experiment with some of the females I've had in my care. I have exotic tastes, I have no interest in pony relationships"
Jack felt hope swelling in his chest, she had no interest in ponies... he wasn't an animal but he wasn't a pony either, maybe he would be the perfect middle ground that Fluttershy could consider boyfriend material! Jack cleared his throat and confidently said "In that case I have only one thing left to ask! Fluttershy... would you like to go on a date with me?"
Fluttershy choked a little on the sandwich she was eating, then once she swallowed she looked at Jack completely puzzled and went "Huh?"
Jack repeated the question "Fluttershy, will you go on a date with me?" Jack was asking her out on a date? Even after what he'd seen?! If this was a dream then Luna was playing a very very cruel game with her, she had been crushing on Jack for ages but had never had the guts to confess her feelings and yet here he was basically saying that he felt the same way! She had to remain calm, play it cool, act like she was very collected and level-headed about the prospect on going on a date.
Once Jack got his breath back from being hugged by Fluttershy for several minutes and having the word "Yes" echoing in his ears, they were officially dating and for obvious reasons, their topics of conversation stayed away from Fluttershy's lustful interests unless they happened to be alone. Fluttershy being Fluttershy did what Jack expected and had not initiated anything beyond hugging, it wasn't until about a month later on the third date that she felt confident giving Jack a kiss... however their fourth time would throw Jack a major curve ball. Jack was making a visit to Fluttershy's home, it was a nice warm day and they had both agreed that the weather was perfect for them to have a private picnic together, just the two of them enjoying a meal.
Things had started out normal, they were laying out the blanket and picnic baskets in Fluttershy's garden where many of her animal friends, including Harry the bear were mainly hanging around and respecting their space. Jack still considered amazing how intelligent some of these creatures were and that Fluttershy could actually talk to them, he remembered how she'd awkwardly had to explain that when she went more in depth with how her animal sex activities began, she made it clear that any animal she had sex with actually wanted to have sex with her and that consent was her number one priority when it came to sex.
As the two of them sat down ready to feast, Fluttershy suddenly said "Jack... there's something I... something I want you to do... f-for me..." out of the blue before they'd even started.
Jack, intrigued, went "Sure Flutters, anything"
Fluttershy, feeling bashful but trying not to whisper, went "I know you said you were OK with it but... my whole bestiality fetish thing... I... I don't think I'll ever feel comfortable being with you if I can't be sure you won't regret this relationship and... that's what has been holding me back from becoming... becoming physical with you... in like, you know, the kind of bedroom sense... I've been putting it off a little because..."
Jack could see Fluttershy becomng flustered and said "Hey Fluttershy, relax... just say what you need to say, whatever it is you need me to do to make this work I'm willing to do it, so don't be worried, I've seen you have sex with a bear so I'm pretty sure I can handle anything you say!"
Fluttershy calmed herself, she knew what she wanted to say but she was scared to say it... though if Jack was really so confident that it wouldn't matter then she could face it, which is why she just blurted out "Will you try out bestiality?"
Jack froze, that was the last thing he had expected Fluttershy to say, Fluttershy noticed and stated "You did say anything so............"
Jack shook himself out of his stupor and went "Well yeah it's just... well I wasn't expecting it, do you really think me having sex with one of your animals will you make feel better about this?" Fluttershy simply nodded. Looks like she vehemently believed that this would strengthen the relationship and while Jack wasn't exactly too keen on the prospect, he at least respected that Fluttershy wanted him to try it and that if he didn't like it, he'd probably only have to do it just this once... though if he did like it well, that was something to ponder about in the future. Jack said "Alright, show me all of your girls and let's see what happens"
Fluttershy smiled and the two of them went looking through all the female animals that Fluttershy just so happened to be taking care of in the hopes that one of them might be horny and, more importantly, able to handle a human cock in their pussy, nothing smaller than a chicken. Jack was surprised that amongst all of the typical farm animals and woodland animals there was actually a fully grown lioness in the mix, it didn't seem to be interested in eating any of the other animals but that begged the question... what kind of meat was Fluttershy feeding it? Fluttershy saw Jack looking at the lioness and asked "What do you think of her? Her name is Lana, she's staying here while Afriquestria is looking for a suitable pride that they can introduce her to"
Jack wasn't sure he could exactly judge the beauty of a lioness but he had to admit there was something strangely familiar about her that made him realize that actually, yes, as strange as it sounded this lioness was incredibly attractive. She had a sandy beige kind of tone to her fur and very striking blue eyes, she looked soft to the touch and she seemed fairly docile for a lioness, Lana was a cute name too. It was at this point that the lioness in question noticed that she was being looked at and started wandering her way over to Jack, inquisitive and curious about this strange creature that was giving her so much attention. Jack stayed still, trying not to seem frightened as Lana sniffed at his body curiously, then something odd happened.
It might have been his imagination but Jack could have sworn that he'd just seen Lana give him lidded bedroom eyes that just screamed the words "DO ME" right before she purred loudly and rubbed her body over his crotch, then walked away with what appeared to be a teasing tail flick, it seemed like Jack had read the signals correctly because Fluttershy reacted by giggling and saying "She likes you very much"
Jack turned to Fluttershy and asked "Really? Like... in a sexual way?"
Fluttershy nodded "Uh-huh, poor girl doesn't have much company and my tongue can only do so much for her, she obviously misses the kind of raw, strong, powerful, primal rough love that only a male can provide. Why don't you show her what you have to offer down there?"
Jack could hardly believe what was happening, he was far past being opposed to this, not that he had been particularly against it in the first place, it was just a very bizarre set of circumstances he had found himself in. First he was in a pony threesome, then he'd claimed the holes of three fillies and now that he'd got together with his dream girl... dream mare? Whatever, now he was trying to woo and seduce a lion!Jack unbuckled his belt and pulled down his pants and underwear, casting them aside and allowing his quarter chub to be on full display.
Lana caught the scent she had liked before, only this time it was stronger. Lana turned to see Jack's genitals and made her way back over to inspect them, she noted that he was slightly hard which demonstrated his interest in copulation, perhaps if she more explicitly showed that she felt the same way then he would become fully erect enough to proceed with the breeding process and penetrate her cunt. Lana was blissfully unaware that Jack was incapable of fathering cubs. Nevertheless, Lana was determined to confirm that she deemed Jack a suitable mate, which she did by licking his hardening prick in appreciation of his equipment, finding that the taste wasn't too bad.
Jack shuddered as Lana's sand paper tongue was dragged across his length, despite the rough scratchy texture of Lana's tongue, it was just as stimulating as the smoother more tender tongues that ponies and at least one dragon possessed. Jack had a stiff and turgid member within minutes, Lana was satisfied that he was ready and so she turned around as she lifted her tail, unashamedly presenting herself to be truly bred. Fluttershy, other than being incredibly wet, did nothing but stand by and watched as her boyfriend indulged in her rather naughty and taboo kink. Jack took his place behind Lana, gripping onto her hips as he aimed himself at her lioness love lips, he got in position as he said to himself "Holy shit... I'm fucking a lion" before sliding himself into Lana's pussy.
Jack had expected Lana's fur to be very coarse and wiry, though upon gripping onto her hips he found that the fur was in fact quite the opposite, it was soft, smooth and felt very pleasant on his skin... although those words could be used just as easily to describe her cunt. As Jack began to methodically thrust in and out of Lana's fuck hole, he found her walls to be exceedingly moist and silky, his cock practically glided in and out of her love tunnel and the warmth... no, the HEAT of the thing, it was almost as if her insides reflected the hot temperatures of her homeland, the Afriquestrian grass plains of the great Serengeti.
Although she was unable to communicate it, Lana was enjoying herself just as much as Jack was. The lion cocks she was accustomed to from her old pride were what was expected from any big cat, big sharp barbs from base to tip that only served two functions, scooping out the cum of other lions and scraping the walls of the lioness in question to induce pain, which supposedly triggered ovulation. Impregnation wasn't fun. With Jack and his exquisitely smooth human cock however, it was a completely different story. It was like his tool was crafted specifically for pleasure rather than pain, it was long, girthy and the creature it was attached to lasted longer than one minute. Lana could get used to this!
Fluttershy, despite her intention to just watch and appreciate what Jack was doing for her, couldn't resist the temptation to press a hoof to her aching cunny and start rubbing away at her folds, breathing heavily as she watched her beloved boyfriend pounding an Afriquestrian lioness. Jack was finding this more pleasurable than he had imagined, enough that the fetishistic nature of the act was all but forgotten, he was panting, sweaty and ramping up the speed of his thrusts with every passing second, desperate to fuck Lana with all his might despite his tired muscles and waning energy. Jacks hips collided with Lana's plush behind at an alarming rate, the only thing that made Jack hesitate was a few minutes into the sex, Lana suddenly let out a very small roar.
Jack was concerned that either he had hurt the poor lion or that she had suddenly turned aggressive, he soon discovered that he was wrong when he felt everything from his groin to his knees suddenly drenched in an unspeakable amount of female fuck fluids, the heat concentrated around his dick only intensified while Lana's walls milked him for his seed. Exhausted by the whole ordeal, Jack caved in, gave in to his desires and let out his own roar as he forced himself as far inside Lana's caverns as he could go and blew his biggest load yet, his pent up cum factories emptying themselves more than ever before to a point where his nuts almost seemed to shrink after being drained of so much fluid.
Once Jack came down from the euphoria of finishing inside Lana, he slowly pulled out only to hear a squeak from behind him as Fluttershy had her own quiet orgasm, so quiet it was almost completely silent. Lana, seemingly tired, lied down and purred, a very satisfied lioness. Jack sat down next to Fluttershy to catch his breath, the silence was only broken a minute later when Fluttershy whispered softly in his ear "Thank you Jack, I promise that I feel confident that this relationship... even if it doesn't last forever, it's going to be perfectly splendid... and to show you how much I appreciate what you did for me, considering it was new and unfamiliar territory, I'll do more than just kisses and cuddles tonight... I... I w-want to give you a hoof job... is that OK?"
Jack held back and laugh and smiled as he replied "That is more than fine, random dragons, ponies and even wild animals I'm happy to just whip it out and get to work... but you're special, we'll take our intimate and private moments at your own pace... because I care about you..."
Fluttershy shed a tear and nuzzled into Jack's side.
It was a mystery, truly it was, even to himself. Jack was the one and only human living in Equestria and not a single creature knew how he had arrived, when he had arrived, why he was the only human, no one knew anything about Jack except for what he told them, which was very little.
There were plenty of theories about Jack which had very flimsy and weak evidence or were just completely ridiculous but the facts of the matter were clear, his name was Jack, he was nineteen years old, he was bisexual, he was male and despite having all of his memories intact he himself had no idea how he had gotten to Equestria, there was just a blank space in between his last memory from his home town in America up until his first memory of finding himself stood in the middle of the Everfree forest.
Settling into Ponyville had been tricky to say the least, especially with Twilight always poking and prodding him, running an endless series of tests and bombarding him with questions that he didn't always have the answers to. The residents of the town were nice enough and after getting over the whole "sentient colorful horses" thing, he had a friendly rapport going with most of them.
Although Fluttershy had mentioned the possibility that their relationship might not last forever, the fact of the matter was that it did last a very very long time with almost no hurdles. Eventually Fluttershy did muster up the courage to do more and more sexual things with Jack in her own time, she'd even gone as far as buying a costume and trying out a little role play. Of course, bestiality was still a big part of Fluttershy's sex life, she had made it very clear that she didn't want to give that up and Jack had agreed on the condition that he be allowed to have sex with other Ponyville residents now that Lana had been carted off back to Afriquestria.
One big hurdle that did come up many years down the line was the idea of marriage, Twilight Sparkle had said that interspecies relationships were fine but that marriage was a bit more ambiguous and kind of a gray area when it came to the law, so it was very touch and go for a while. Needless to say, the relationship persisted despite both of them engaging in some casual sex with others when they weren't having fun witch each other, one thing that annoyed them was that ponies were constantly asking if they were gonna adopt some kids, to which both of them said a very definite "No". Fluttershy wasn't maternal in any sense and didn't consider herself the mothering type, while Jack just thought it would be awkward for foals to have a human dad, especially since he was the only human in existence, the bullying didn't bear thinking about.
In any case, Jack and Fluttershy were happy.
The End
Author's Note
Thank You UndeadMan for this story idea! I hope you enjoyed it :)
