The late spring air was heavy over Sweet Apple Acres, and so were the pheromones that rutting season promised. Normally, the Apple family were able to get through mating season with nothing more than a little discreet masturbation, but things were getting to be a bit much for Big Macintosh, who found himself wanting something more...Intimate. The stallion had faked a sprained ankle that morning, and he sat by the window as he watched his sister go out into the orchard to finish the last of the apple bucking.
With Apple Bloom visiting family in Manehattan, and Granny Smith asleep by the radio, this would be his one chance to get things out of his system before Applejack would be hanging around the house again and he wouldn’t have any privacy. With a smirk, he slipped out of his chair and climbed the stairs while taking care to not make a sound.
Mac quietly pushed open the door to Applejack’s room and drew the shades, before looking around at her private space. Surprisingly, the rough-and-tumble cowmare had gone through the effort of keeping her room mostly clean, and so it wasn’t hard for him to begin going through her dresser until he found his prize: her underwear drawer. His sister had a bit of a feminine side somewhere deep inside her, and the bundles of silk and lace before him attested to that. He pulled one out at random, a tiny blue number, and with a quick glance out the window to make sure she wasn’t watching, he stepped into her panties and began working them up his tough, muscled legs.
It wasn’t easy, and he nearly tore her intimates in half getting them past his thighs, but after a few minutes the horny colt slipped his sister’s underwear completely on and tucked his balls into the front. His entire cock wouldn’t fit even when limp, and it certainly wasn’t anywhere near that, so it stuck out proudly for him to begin rubbing. However, that wasn’t enough for him yet, and he began rooting through her clothes until he found the nylon stockings he wanted. Five more minutes, and they were clipped to his panties and squeezing his legs in delicious female smoothness. Now he could masturbate properly.
Of course, that assumed a certain chromatically-inclined pegasus didn’t choose just then to kick open the window and see everything.
Which she did.
Oh shit.
“Hey AJ, are you-” Rainbow Dash stopped mid sentence and midair as she surveyed the scene before her. “Oh. Oh sweet Celestia.” She almost immediately broke out laughing as the large stallion blushed and tried cover himself up.
“It’s...Eeyup.” Dash wiped her tears clean as she rolled back over and watched him, before nodding and smirking at the poor colt.
“Yeah, it’s exactly what it looks like, isn’t it? Does your sister know you like looking pretty in her clothes?” Big Mac’s eyes went wide in terror, and Dash simply laughed.
“You know, you look pretty good like that, so I’ll cut you a deal. AJ never has to hear a word about this, but in exchange you have to come back to my place and do absolutely anything I say for the rest of the day. Sound good, or you want me to go find lil’ sis?” Big Mac blushed and averted his eyes, knowing there was only one option if he didn’t want to catch all hell from his sister.
“Eeyup. Can’t fly, though.”
“Twilight cut me together a few scrolls last time I wanted to bring a few friends to a competition. Just read one of those and you can walk on clouds all day! No excuse now!” The stallion nodded and began undressing, feeling Dash’s eyes on him the entire time. He made sure to put everything back exactly as he’d found it; doing this would be bad, but having his sister figure it out anyway would be much, much worse.
“Sweet. Give me five minutes and I’ll make sure AJ won’t know why you’re gone. You get your flank over to my house and I’ll meet you there.” He stepped out of his sister’s room as the pegasus took off, and after the five minutes she’d mentioned he left out the back door, pretending a limp in case Applejack was watching. This was going to be a very long day.
* * * * *
Half an hour later, the earth pony was getting mighty tired of waiting. On the other hoof, leaving would probably invalidate his deal, and so he continued watching the skies until he saw Rainbow coming toward him with several bags in her forehooves and a gently-glowing scroll in her mouth, which she tossed to him.
“You made it, good. You wouldn’t BELIEVE how excited Rarity was when I told her I was getting in touch with my feminine side, I thought she was going to give me the entire boutique!” She grinned devilishly. “She gave me more than enough to have fun with you all day and all night, though.” She dumped everything through a window and began forming a cloud staircase while Big Mac read the scroll. They both finished at the same time, and he began trudging up to his doom.
“Let’s get started. Put this on.” Dash pulled one of her bags out of the pile and tossed it to him once he was out of view inside her home, and he opened it with two parts shame and one part aroused curiosity. Naturally, Rarity had gone all-out with Dash’s ‘feminine side’ and everything inside it was bright pink with lace trim and hearts embroidered on any flat surface. Mac pulled out a pair of panties and held them up to examine, before sliding them onto his legs with the same attention he had given to his sister’s intimates. Dash wolf-whistled at him as he got them on and walked around him, giving everything a thorough examination before casually slapping his ass with a wing. The stallion jumped and blushed a deep red, before Dash held a light pink corset up for him.
“Everything in the bag. I want you to be a sexy little filly.” He glared at her and reached out for her to slide it under him and lace it, but he wasn’t expecting her to pull it so TIGHT. He wasn’t entirely sure his lungs were still working by the time she was done, but he did have a much more tight figure and that seemed to please his mistress. Not needing to be told again, he reached into the bag and brought out the first thing his hoof met, which was a pair of equally-pink socks. These, he could handle and he slid them on without much effort. That only left the dress.
Dash pulled the last garment out of the bag and held it up to him, admiring her friend’s handiwork. It was like she either knew Dash was going to be toying with sex-slavery or she thought the pegasus had taken up prostitution on the side. The dress was fairly minimalistic, with the skirt just a bit too short to be proper in high society and a zipper sewn into the back for easy access. It had wing-holes, of course, but Dash had no idea what Rarity had been thinking when she’d made it. It was perfect.
“C’mon over, big sexy! Momma wants to put this on you herself.” She unzipped it and slid it over his head, pulling it taut and making sure the fabric fit around his large frame. Seeing how it fit the larger pony perfectly, all of Dash’s doubt was dispelled; Rarity knew what was going on. Of course, seeing as the other option was actually thinking Dash had a feminine side, the pegasus didn’t see it as anything strange. If anything, it meant she could get more for him later.
Much to Rainbow’s delight and Big Macintosh’s dismay, clothes weren’t the only things Rarity had provided her with. She rooted through the remaining bags until she found a small box, and she motioned for the stallion to sit down on the couch. he did, and she carefully straddled him as she opened the makeup kit and reached out to his face.
“Y’know, I think this is going to be the first time I’ve done anything with makeup and actually liked it! You should feel honored.” Honored was one of the few feelings Mac hadn’t gotten to know over the past several minutes, and it still wasn’t doing much as she began touching him up. Rather than covering him in enough to actually make him look like a mare, she was just giving him as much as normal mares used.
She wasn’t used to doing it to anyone, let alone a colt, and so what should’ve taken a few minutes stretched out to over half an hour, which meant the continually aroused colt was staring into her eyes that entire time. The urge to lean forward and kiss her was overwhelming, but he held onto what was left of his masculine pride and kept patient. Celestia knew what would happen if he did something like that without her permission.
“There. All done. Wanna see what a pretty filly you are?” Mac blushed and nodded as Rainbow picked up a small mirror and turned it so he could see. He almost couldn’t believe it was him. Rainbow had managed to make him look like an actual (albeit masculine) mare. He turned his face to the side as he examined his new look.
“Mmm, not bad, if I do say so myself. And this is coming from the lesbian in the room.” She rubbed up against his side and ran her feathers along his back. “You did know I’ve been banging your sister, right?” The stallion stared at her incredulously before shaking his head in surprise.
“Nope.”
“Well, you do now. Now it’s your turn, big sexy.” She turned his head toward her and kissed him bluntly on the lips, immediately shoving her tongue into his mouth. That was all it took to break the colt’s resolve, and he immediately rolled, pinning her underneath him and raping her mouth with his tongue.
“Hey, hey! Slow down there, I’m your mistress! I call the shots, you do as I say and absolutely. Nothing. More. Clear?” He lay on her for a moment more, before she raised an eyebrow and reminded him what the stakes were in all this. “Or I can tell your sister and we never do this again. You want to do this again, don’t you?” He shook his head violently, but she brought a hoof up and slapped him. “Don’t lie, you like being my little filly. Be a good girl and you can come back and do this again, no chance of AJ finding out.”
“Mrr...A’right. You’re the boss.” She smiled as he rolled off of her, before lifting his skirt. She looked at his silk-clad ass with a smile and pulled his panties down just underneath his ass. The colt had a decent sense of hygene and kept it clean, which meant she wouldn’t get anything dirty.
“You need to be put in your place, don’t you? You like dressing like a filly, let’s see if you can take it like a filly.” She held up a dildo she normally kept for herself and climbed onto his back, sitting on him backwards as she worked the horsecock into his ass with both hooves. She started slow, easily able to tell he was a virgin, but he wasn’t going to be for much longer. For his part, he whinnied in surprise and pain, but aside from a bit of hoof-stamping he stayed put and let her do as she wanted. The first inch was the hardest, but as the flat, plastic head pushed past the ring of muscle she managed to slide much of the rest into him, until she gave one final shove and fit the entire dildo into the stallion’s rectum.
For Mac’s part, he was going through a dozen horrifying emotions. First was pain, and a lot of it, but strangely it felt really good. He hadn’t expected to like having a cock in him, but once it was there he was surprisingly content. It seemed like it almost completed him, and he was having fewer and fewer reservations about making this a regular thing until Dash chose to speak up.
“Um...Yeah, shouldn’t have done this with hooves. How mad would you be if I can’t get it outta there?”
“...What.”
Dash continued pawing uselessly at the base of the dildo, and rather than get a grip on it managed to just shove the entire thing past his sphincter and irretrievably into his ass. He stood stock-still, waiting for her to get it out before slowly realizing that wasn’t going to be happening anytime soon. He cautiously took a step and immediately wished he hadn’t as pain shot through his haunches. Dash climbed off with a shrug and forced smile, hoping he wouldn’t kill her for this.
“Dunno what I’m gonna tell you, we need to get a unicorn up here to pull that thing out.” Mac groaned as she made her decision, but trying to push it out himself wasn’t working. If anything, it felt like she’d gotten it caught on something.
“Fine, get someone to see what you did...How are you going to explain things?” She thought for a moment before smiling and nodding.
“ I won a bet and you have to be my slave for the day, simple enough. Sound good?”
“Eeyup.” She took off out the window, and Mac managed to hobble over to the couch and lie down until Dash made it back with the help. if nothing else, there didn’t seem to be any way for this to get worse...
* * * * *
“Daarling, please tell me this isn’t going to scar me forever.”
“No promises. It just needs to be done.”
“This is going to make my magic feel dirty for weeks! I can’t believe you asked me to do this.”
“Rare, I’ve seen your toybox. Your magic is filthy already.”
“That’s just for me! How do you even know about that?!”
Big Macintosh’s ears perked up at the sound of the two bickering mares as they came toward the house, and he carefully rolled over toward the door as they came up. Seemed his suffering would be over soon. Rarity came in and stared at him for a few seconds, before closing her eyes and sighing. She blindly reached forward with her magic, feeling the plastic and pulling it carefully out of the colt. He had gotten so used to having it there, the feeling of getting it out made him moan in pleasure, and her eyebrows shot up on reflex.
“I had figured you for many things, my dear, but a homosexual wasn’t one of them. Am I done here?” Without waiting for an answer, she turned and walked out the door, and Mac got himself back to his hooves just in time to see her bolt back toward town, presumably to find some ice cream and a radio show that could wipe all of this from her memory.
“Heh, while I was out, I got you another one~” He turned back to Dash and reared back when he saw the silicone dick hanging between her legs, before realizing it was a toy. Of course, if it was hooked on, it wouldn’t get stuck again, so...
He didn’t have much of a choice in the matter, because within seconds Dash had mounted him again and began fucking him properly, slowly at first before picking up speed. The stallion nearly buckled but held fast, leaning against the couch as Dash railed him as hard as she could. She continued pounding him for what felt like an eternity, the pain and pleasure building, until he finally gave in and shot his load through her cloud couch and onto the ground below.
“Ugh...Fuck...” He leaned forward on the cloud, glancing back to see a drop of blood roll down his cock and drip off the tip, and he didn’t need to feel to know Dash had done permanent damage. If nothing else, he’d never be able to forget that feeling. He lay down as Dash pulled his panties back up and she curled up next to him, her comparatively tiny frame snuggling up against his underbelly and her rump touching his cock through his dress.
“Ooh, still hard? Maybe it’s your turn to give it to me. After all, I get all the sexy fillies~” He ground his hips against Dash lightly as she rubbed back against him. “Easy there, little filly. You’re still mine, remember?” She sat up and turned him on his back before slipping the dildo off and straddling his hips. It was everything Mac could do to keep from shucking his panties and plowing into her right there, but he held on. Within seconds, his patience was rewarded when she gripped his cock and leaned forward, her face resting against his and his sizable erection up against her lips. She smiled and licked his mouth, before sliding backwards agonizingly slowly, letting his gigantic hunk of meat split her open.
“Damn, bigger than any dildo I’ve ever found...Fuck!” She leaned back, pressing as much of his meat into her as she could. Even at the end of her passage, she could barely fit half his length, but that was enough as she began to slowly fuck him. He felt her cunt grip his shaft as it tried to refuse to let go of its prize, until she slowed and pushed herself back on. She fit another half-inch, and he leaned forward to run a hoof through her wings, ruffling her feathers and making the pegasus jolt in surprise. She continued fucking him, picking up speed as she did, until both ponies had a deathgrip on each other and were lost in the throes of ecstasy.
Big Mac let out a low moan as he felt his cock swelling almost to burst, and he could tell Dash could feel it too as she began to buck on instinct, before her mind reasserted itself as she almost tore herself off of him. His seed splattered on her ass and tail, finally exhausting him as she lay on top of him.
“Sorry, big boy, no colt gets to mess up this hole, particularly not during rutting season. Still, keep this up and maybe I’ll start thinking of you as a mare~” She winked at him as she rolled off of him, looking out at the setting sun. “So, I guess you held up your end of the deal. AJ will never know what happened. Still...Come back sometime, yeah?” He chuckled and began stripping, looking forward to getting back to life on the farm.
“Jus’ keep dreaming, Rainbow. Maybe I will, who knows?” He walked out the door with a final smirk, looking back at the mare fondly and trying to figure out why he’d lied to her.
Of course he was going to come back.