Author's Note

At the request of 99goosebumps, I have added a bonus chapter to this story where Fluttershy pegs Chester, enjoy!

Bonus Chapter: Flutter Fucker

The sun was setting and casting an orange glow against the sky as clouds sailed silently by, a gentle breeze swept across the landscape, gently whispering as it glided through the grass. The evening slowly slipped away to make way for a calm night, the mood was perfect and Fluttershy decided that now was the time to wear a massive horse cock and peg Chester. Chester was a handsome horse and Fluttershy had seen with her own eyes that he could show a girl a good time, though she could tell that underneath all that pride of being able to wreck human pussy, there was a horse that was waiting for a human girl to tease his ass hole before wielding a huge cock to pound him. Fluttershy wanted to be that girl tonight. Fluttershy walked into the barn where Chester stay, completely naked except for socks and shoes as she carried a big duffle bag on her shoulder. She saw Chester in his usual spot chewing down some hay before lapping up some water, jut seeing Chester made Fluttershy shudder, he was a large powerful beast with a dick to match, not to mention two fat heavy nuts filled with hot delicious horse spunk. It was so lucky that Chester had a penchant for human girls rather than mares.

As Chester took notice of Fluttershy's presence, she smile as she dropped the duffle bag onto the floor and said "Hey big guy... how you feeling this evening?" Chester didn't answer, nor did Fluttershy expect him to, it just made her feel more comfortable to talk to him before diving straight in with the whole "relax and let me fuck you" stuff. Fluttershy walked up to him and started stroking his back, slowly moving nearer and nearer his rear as she planted kisses along his side, so enough she saw the parts of Chester she was most interested in, his big cum-filled balls and his pronounced pucker. She smiled as she eyed up his ass with desire, ever since she had laid eyes on Chester's back door she had wanted to stretch it out with a big strap-on and now she was finally doing it. As she flt herself getting wet "Oh Chester... fuck you for being so hot... damn I can't wait to make you my temporary bitch... but first, let's get you nice and prepped shall we? Gotta make sure your ready for me, not to mention your cock is still in its sheathe and we can't have that now can we? So let me tease you a little, make you nice and hard, then we can move on to the part where I ram your fucking ass hole..."

Fluttershy stood directly behind Chester, staring at his rear entrance with sexual hunger, she moved forward and gave his ring a passionate kiss, before moaning as she caved in to her desires and began dragging her tongue along his pucker, eagerly coating it in her saliva. Chester's reaction was instant as he made small grunting noises while cock plopped out of his sheathe and began to steadily harden, pulsing with every beat of his heart. Fluttershy pulled herself away from her sloppy make-out session and grinned to see that Chester was already semi-erect before she was satisfied she had tongued his rear enough and was ready to move on, as she took note of how soaked her pussy she was she said "Fuck... Chester, ordinarily I'd happily let you cram your huge slab of fuck meat into my holes but tonight is different... it's your turn to have your hole penetrated and I'm not gonna let your huge virile fuck stick distract me!"

Fluttershy grabbed a nearby crate and pushed it until it was behind Chester, she stood on it and, satisfied that she was at a good enough height, went and unzipped the duffle bag to retrieve a bottle of lube and a big light pink strap-on horse cock, the same shade as her hair. The strap-on was a bit smaller than Chester's dick in terms of length and girth, though that wouldn't matter too much considering what Fluttershy was planning to do with it. Fluttershy poured some lube onto the strap-on and spread it around with her hands, making sure there was a good thick layer covering every single inch of it, if she was gonna fuck Chester then she needed to make the initial penetration as easy and comfortable as possible, which is why she also applied a good amount of the cold substance to Chester's back door, being sure to test out it's effectiveness by pushing a couple of fingers into his rump. Fluttershy slid the strap-on up her legs, fastening it around her waist, stood on the crate and finally everything was ready, Chester's hole was slicked up and slippery just like the strap-on horse cock that Fluttershy was perfectly poised to push into his tight rear entrance.

Fluttershy shuffled forward and pressed the tip of her horse cock against Chester's pucker, she gauged Chester's reaction and was relieved to see that he was perfectly calm and had moved back a bit himself, as if giving permission or outright encouraging her to proceed. Fluttershy smiled and after some pushing, head of her strap-on popped into Chester's hole, his rear readily accepting the phallic intruder, Fluttershy sighed in contentment and said "Ah... there you go Chester, like how I feel inside you boy? It's only gonna get better so I hope you're ready for a good fucking you equine sex machine!" Fluttershy grasped onto Chester's hips and pushed forward, sinking inch after glorious inch of strap-on horse cock into Chester's bottom until she reached a barrier that stopped her from driving herself in to the hilt, the medial ring. Fluttershy adored that there existed a company that cared about accuracy when it came to sculpting a wearable horse dong but she think they could have at least considered the drawbacks of making it hard to plunge balls deep inside.

Fluttershy held onto Chester's hips a little tighter and started pushing forward with all her might, using as much force as she could in an attempt to squeeze the medial ring into Chester's rump and finally clap her hips up against his buttocks before pounding him like their lives depended on it until they both came, she wasn't going to stop until it happened. After a minute or so of gritting her teeth, scrunching her eyes and ignoring the sweat rolling down her forehead, the medial ring slid inside Chester's tight ass, allowing Fluttershy to relax briefly before finally pushing the rest of the way in, her pelvic finally making contact with Chester's butt, ready to ram him as hard as possible with all of the effort that Fluttershy's little body could muster. Fluttershy giggled slightly maniacally as she said "Alright big guy, your ass is long overdue for a pounding! If you wanna fuck us human girls then us human girls have the right to fuck you right back you sexy stud!"

Fluttershy pulled back slightly, emptying Chester's ass of a few inches of cock, then immediately thrust back in to refill that space. As Fluttershy began humping away, Chester made small noises of approval, his still semi-erect cock swinging around and his balls churning with a hot thick load that, with any luck, would soon be fired onto the barn floor if Fluttershy had the stamina to fuck him to completion. Anyone who knew Fluttershy would have said that she had the energy. Fluttershy breathed deeply as she began to pump her horse strap-on in and out of Chester's stretched back door, calmly and confidently thrusting her hips back and forth, ignoring the slight ache that came with using muscles that usually weren't needed except for the very specific scenario of having to fuck something or someone with a strap-on cock. Minutes passed with Fluttershy slowly increasing the pace of her fucking, just going that little bit harder, that little bit faster, making sure Chester got as much enjoyment out of it as she did, had she been wearing panties they would have been soaked, as her juices flowed freely from her cunt down along her thighs. Fluttershy saw that despite how much Chester was enjoying himself, his cock wouldn't be getting much harder than his rather respectable semi, with that in mind, she decided that she might as well rush the both to the finish line and began hammering away at his ass.

Fluttershy was panting and sweating, the only other sounds being Chester's surprised yet pleasured quiet neighing and the constant plapping of hips repeatedly colliding with cheeks. Fluttershy went "Come on Chester, your owners secret nickname for you is nut buster, so live up to it! Fucking cum before I do! Your hole is twitching, your cock is hard and your balls are full, fucking empty yourself for me please! I can't keep this up much longer before I fucking cream myself!" Fluttershy heard Chester's cock slap against his belly before he let out a loud whinny that echoed throughout the barn and blew a tidal wave of spunk onto floor beneath him, three thrusts later and Fluttershy squealed as her pussy gushed, her walls trying to milk a dick that wasn't there as she held herself deep inside Chester. Once the last few drops of jizz had fallen from the tip of Chester's cock and Fluttershy had regained her strength, she yanked the strap-on out of his hole and sat on the crate, just watching his cock retreat back into it's sheathe. Fluttershy chuckled and said "Boy, you're dreaming if you think that before I go to bed that I'm not gonna coax that monster of yours back out again for a midnight blow job"

The End