Interspecies Intercourse

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.