Interspecies Intercourse

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!"

• later -

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.