My Little Sissy: Coltfriends Are Open-Minded

by SwiperTheFox

Rating: mature
Tags: Sex, Comedy, Big Macintosh, Slice of Life, My Little Pony: Friendship is Magic, Rarity, Romance
Length: 3046

Big Mac's steamy relationship with Rarity leads him into fetishes that he's not happy about.

Big Mac's steamy relationship with Rarity leads him into fetishes that he's not happy about. At the same time, he loves her with all with all of his heart and tries to be open-minded. Still, Rarity's plans for this upcoming evening seem to be a bridge too far, even for him. This is a prequel to my fanfic "My Little WereRarity". Please note that there's frank sensuality that involves crossdressing as per the title. Thanks for reading and please comment.

=> I am so freaking totally not prepared for finals.

Published 2012-05-04 06:34:01 UTC
Last updated 2012-05-04 06:34:01 UTC

The Whole Thing

Big Mac knocked on the door, glancing back up at the huge full moon. He frowned, knowing that it meant Rarity had 'special plans' for that evening. He looked back down at the side wall of Rarity's boutique and saw his frowning reflection in a window.

Of course, she had 'special plans' every other night. Mac loved that so much about that beautiful mare. She represented an escape-- a full blast of life outside the farm and all the messiness, toil, hot afternoons coupled with cold nights, and everything else that he enjoyed but often got bored of-- as well as just being the most beautiful mare that he had ever seen outside of royalty. She took to the stylish, courtesan-like personality to a T, always asking him to 'join me for some special plans' rather than just remarking 'come by for some hot fun later' as Rainbow Dash or Cheerilee would. He loved that so much.

His ears flickered as he heard Rarity slinking around inside the boutique. He felt the full moon shining on him, causing a thick lump at the pit of his stomach. It seemed to be the oddest thing. Day in and day out, Rarity always put up that prim and proper front. She really had the same streak on the inside, yet the nights where she could walk around outside with the sunny moon flicked some inner switch inside of her. She became naughty. A red-blooded stallion such as himself loved seeing a masculine sort of naughtiness from a mare, but Rarity's use of the term 'special plans' had a whole other meaning on these fully lit nights.

The door creaked open, snapping Mac out of his inner monologue. I suppose I'll just see what she wants to do this time. He took a deep breath, wondering what on earth Rarity would be wearing.

"Why, so wonderful for you to join me here tonight, darling," she said. Oddly enough, she wore nothing at all. Mac shrugged every so slightly as he walked inside.

"Great to see you again, Rarity," he replied. He didn't need to force himself to talk romantically. It came naturally for whatever reason, even though being with such a 'perfect ten' should have made him nervous.

"Great, indeed," Rarity cryptically commented. Mac nodded as she made his way to the side of the main showroom, seeing a plate of those Twilight-made magical iced teas that he loved so much.

*Slam!*

He spun around and saw Rarity leaning up against the slammed door, starting to pant. Her mane curled up around her shoulders as she nudged her bottom hooves wide. She held her mouth slightly open, with a 'cracked' kind of expression coming over her face.

"Is everything... okay..." Mac muttered, still leaning up against the end table.

"Okay? Okay?" Rarity replied, getting down on all fours and putting her body right against the ground. "Okay? Ok-ah-ah-hey-kay-y! Okay! Okay!" She scurried along the ground like some kind of insect.

"Rarity," Mac said, trying to put on a very caring and compassionate tone, "is there something you need me to--"

"Oh, need has nothing to do with this!" Rarity called out, hopping straight up in the air just like Pinkie would. She landed atop the table right in front of Mac, her frizzy tail and mane wiggling in the air. "It's a matter of wants, dear. Don't we have them? Both of us, darling?" She rubbed her front hooves together while her eyes pulsed.

"Eeeeeeeeyup," he replied. He slanted backwards a few inches. The tingly feeling between his legs reminded him of the fact that he had consummated his love with Rarity once every two days, or every day, for months. Then, this past week began, and the hangover after being love drunk hurt. It hurt a lot.

"Now, are you sure that you don't want to have a little taste of the potion?" she asked, panting harder. She magically lifted over an open burlap bag of injections behind her. "Myself, I've just had a quarter dose today. And the effects are exhilarating." She let out a loud, feminine whine.

"Eeeeeeenope," Mac replied. He didn't care if Twilight's serums had perfect science behind them. He didn't care that they were completely reversible. He didn't care that they amped up pony lust in small doses and, in full doses, would transmogrify them into a werewolf-sort of creature with the sexual talents that even Princess Celestia would find impressive. "Ah ain't pokin' no needles into me. No way. No way." It was a particular sore spot in their relationship, something that bugged him deeply.

"Suit, ugh, yourself, darling," Rarity groaned, still rubbing her hooves together.

Mac simply nodded. He watched as Rarity guzzled down on the iced teas, magically tossed the glass out of an open window, and leaped off of the table. She sped to the corner of the botique, grinning deviously. He didn't like the look of that much, but she seemed less animal-like compared to their last night together, at least.

"Tonight is a fabulous night," she said, magically swirling clothes in the air above her head, "For some--" She giggled. "Roleplaying."

Big Mac groaned. He immediately regretted not just saying 'no.' A groan meant 'yes'. He knew it. She knew it too, and she hopped around from side to side, hooves treating gravity like nothing.

"Guess who's the devious and horrible monster that's consumed by mindless masculine lust," Rarity called out, pretending to look scared as she magically lifted over a dirty, shady-looking brown coat with tattered grey pants and a ragged dark grey cap, "and he stamps through the alleyways of Ponyville like the true, hardened sexual offender that he is-- hunting for another victim to ravish as the full moon shines upon him?"

"Me?"

"Me, darling!" Rarity yelled, squealing with pure happiness as she bounced in front of mirror. She bucked up on her hind legs and threw a slimy, dirty dark brown shirt on. She smiled as the shady-looking coat and cap went on. She magically tucked her mane and tail close, hopping to the side as she slipped the pants on.

"Charming," Mac muttered.

"Don't I like absolutely filthy and evil, my love?" Rarity asked, throwing musty make-up on and curling her face. She turned over and glared at Mac, doing her best impression of a angry thug from a noir detective comic book.

Mac nodded while letting out a resigned sigh.

"And, my amazing and open-minded coltfriend, I have another question," she said, stepping over to Mac's table. He watched as she splattered more make-up along her face and body, making her look more and more like a grimy stallion. "Guess who's the sweet and innocent young filly that's just walking home from a late night of studying at a friend's house, her virgin flanks wiggling in the air, that finds her soft, kind-hearted view of the world smashed into a thousand pieces as the monster jumps upon her and prepares to pop her succulent cherry?" She licked her lips at that last word.

Mac simply closed his eyes, barely able to force out the word. "It's... it's..." He felt himself being magically slid over with new make-up getting slathered across his face. "It's me."

"Excellent!" Rarity hollered. Mac coughed as he found himself magically flipped into a chair. He figured he couldn't say 'no'. To be honest, he didn't really want to in the first place.

He opened his eyes up again. He saw himself before a mirror as a large schoolfilly's outfit hovered over his head. He stared at the bright pink dress complete with red and light pink striped suspenders and a tight fitting white button shirt as well as the large backpack, which just so happened to be shaped like a giant bunny. Ruby red lipstick, creamy make-up, fake eyelashes, minty perfume, and numerous other girly accessories were all laid out in front of his hooves.

He scrunched his face, feeling his heart beating like a drum. "Do I..." He sniffed. "Do I... have to..."

Rarity leaned over close, whispering into his ear. "I'll go ahead and be blunt, darling." She moved her plot over against the mirror, her pants rubbing against the glass for a second. "If you want nookie--" She span around and held up the schoolfilly outfit. "Then, you wear the bunny."

Mac let out a loud, feminine whine, his hooves tapping against the ground.

"Now, that's the spirit!" Rarity squeaked, smiling widely. She put the clothes on top of Mac's chest. "I've been so looking forward to your makeover, Mackie-wackie."

Mac watched with eyes wide open as long, heart-covered stockings and fancy heels floated underneath him.

"Oh, and by the way. Call my role-played-male-self 'Purity'. And you're role-played-female-self is called 'Mackie'," she commented, whistling a moment afterwards as she pulled the stockings over his hooves.

Mac fainted.

Several minutes later, in a dark alley in a part of Ponyville few tread...

"Ugh, how in Celestia's name do girls walk in these dreadful things," Mackie grumbled, bracing his side against the cold brick wall. He forced himself to step forwards a few more times, shaking. He made a short sigh, and he moved on down the alleyway.

He heard a small splash and some scampering noises from the second floor of the building to his right. He blinked, feeling his heavy fake eyelashes rubbing against his face. Still stalking me... just as obvious as before... but get on with it already!

"Oh, my goodness, it's so dark here," Mackie said in terrible fake acting, moving down besides a set of dumpsters.

"Ahem!" Purity yelled out.

"Okay, fine," Mackie moaned. He took a gulp. "Oh, dear gosfh!" He put on an exagerrated foal's lisp, like Twist eating peanut butter. "I'm so alone. I shouldn't have stafth at my friends' apartfhmensh. I'm so vunerable, here, by myself in this alley."

Several feet above, Purity poised herself over Mackie's body. She slid around from rooftop to rooftop, stepping very quietly down atop the dumpsters.

Mackie put a hoof to his head, letting out a high-pitched feminine moan in his melodramatic acting. "I hope thastf thersf no bad stfallions in this alley. I haven't even had my first thsime yetsh!" He stopped in front of a dead end in the alley. "Oh, where's the way out? If only I had somepony here to give me the way?"

"I'll show you something," Purity growled. He leaned back atop the dumpster, eyeing the crossdressing stallion.

Mackie turned, mouth opening wide. He quivered with sheer mock fear, his bunny backpack falling off of his shoulders between his frilly dress.

"I'll make--" Purity moaned, leaping out into the air. "A mare out of you!"

"Aaaaaaaaaaaaaaaaah. I'm so weak and helpless. I'm so small. Please, stop," Mackie rattled on, leaning up on his back. Purity poised herself over his body, her legs rubbing up against his pantyhose. "I'm just a little filly. I haven't even had my first kiss yet. Let alone my first sex!"

"Your cherry is mine!" Purity hollered, leaning down. She panted big wet kisses along Mackie's neck, make-up smearing all over. She panted all over him.

"No, please, don't," he replied, still mock acting. "You big, strong, masculine evil creature of the night. You nefarious agent of perversity imposing your will upon Ponyville's youth." He chuckled a bit at his own stupid lines. "You must cease your horrible sexual attack post haste."

"Never!" Purity yelled. She leaned down and ran her hooves along Mac's chest and belly, making little circles into his fur.

Mackie moaned, not acting one bit. He felt a tent pitching inside his skirt, and he moved his legs up against Purity's hooves.

"Oh, you like that, you girly little whore!" Purity groaned, leaning over and smothering kisses upon Mackie's neck, shoulders, and cheeks. She dug her hooves under his pink suspenders, pulling them down. Her legs rubbed up against his pantyhose, also tugging it down.

"Yes, I'm a whore," he moaned.

"You dirty little girl. You need to get your marehood filled up." Purity bit into Mackie's shirt, tearing out the buttons. He rubbed his hooves over her shoulders as she went on down. She dug her hooves into his skirt, tugging the ends so that Mackie's throbbing boner stuck out. "Warm, sticky cream dripping all through your marehood."

"Yes, yes! Ravish me! Take me! Use your filthy, horrible masculine hoofs and your awful, strong stallion body!" Mackie shifted upwards, kicking off his heels. He started to pant as well as she stuck her head under his skirt. She bit against the ends of his pantyhose, ripping downwards.

As they scattered into shreds below him, Purity stood up above Mackie's body. She narrowed her eyes, making a huge, devious grin. He watched, panting even faster, as she pulled down her pants. Soaking wet between her legs, Purity arched her back to the side and lined up right atop Mackie's stomach.

"You see it?" she asked, smacking her hooves hard against Mackie's shoulders. "You see my throbbing rod? You see how hungry it is?"

"I see how hungry it is," Mackie repeated, teeth grinding. He felt so much anticipation that he wanted to scream.

"And I see how hungry you are," Purity said, leaning her body backwards. Her plot rubbed up against his rock-hard colthood, pre-cum already dripping into his skirt.

"I see... I... I see..." Mackie moaned, feeling Purity tease him. She wiggled her plot from left to right, nudging his huge member just so delicately. She leaned a hoof up to her mouth, licking it, and Mackie's eyes bulged. He took a big gulp, totally abandoning his mock feminine voice.

Purity dug his hooves into his backpack, swinging it up around her own back. She giggled. "Little fillies like you shouldn't--"

"OH, FOR CELESTIA'S SAKE, JUST SCREW ME ALREADY!"

She opened her mouth up wide. She put her hooves up and grabbed her cap, throwing it over against the wall. She put on a determined face, taking deep breaths. He leaned his hooves down and thrust his skirt up, exposing his colthood completely. He groaned. They locked eyes, and they knew that the roleplaying foreplay had to end.

Rarity slanted herself downward, hips just inches atop of his rod. She held her hooves against his chest, and she leaned backward. He touched the tip of her soaking wet slit. Ripples of pleasure coursed through his body, his head shivering.

"Oh, Big Mac," she moaned. She leaned forward and kissed him. As the lips locked, their heads moved side to side. She immediately ran her tongue into his mouth, knowing exactly what to do and how to do it, and passionate kiss flowed into passionate kiss.

She broke the kiss, holding her head just a few inches above his, and she closed her eyes. He felt his thing rubbing up against her thighs, and he groaned. Their hooves locked, she positioned her slit right above his colthood perfectly, and they both made a happy sigh.

*Thrust!*

Mac screamed. Sheer, unbelievable pleasure slammed his senses. Rarity curled her body back, taking him in all the way to his sack, and he shivered. Tears of joy streamed down his face. She pumped up and down a little, making girly moans, and he barely kept himself from creaming right then and there.

Rarity ground her body left and right, tapping her hooves against his. The bursts of pleasure going through his body drove him mad. He panted hard as his body pumped upwards, trying to take as much of her in as she could.

She felt absolutely perfect. Every glorious inch of her soaking wet marehood fit him so snugly and so tightly, better than any mare that he had ever been with. She somehow managed to push him in even deeper, her body quivering with the movement, and he bit his lip.

"Well there, you naughty little filly," she murmured, hips sliding up and down on his rod, "looks like you're on a hair trigger." She chuckled, feeling thousands of explosions of joy going off behind her eyes.

"Eeeeeeeeyup!" Mac thrust himself in and out with total abandonment. Mountains of pleasure after pleasure built up inside his body, barely keeping control.

"Looks like you want me to take my colthood and shoot it all inside," Rarity muttered, curling over and playing with Mac's shirt.

"Eeeeeeeeeeyup!" Mac pounded Rarity's flanks, his sack slapping up against her pants. The torrents of sheer bliss coursing inside him brought him right up to the edge, ready to simply release himself.

"You, naughty, naughty girl!"

"I'm such a naughty giiiiiiiiiirrrrrrrrrrllllllllllll!"

Rarity clenched herself. Her plot enveloped Mac's pulsing colthood, giving him what felt like millions of slobbering kisses. He kicked his hooves against her pants as she pulled up his skirt, ripping it against his belly. A pure surge of pleasure cut straight into Mac's insides, heading right through every inch of his body. He groaned. She groaned twice as loud.

And he emptied himself. He felt his thing wiggling around inside of her, spurting every last drop he possibly could. He felt her tears of pure happiness dripping onto his neck, and he could barely breathe. His mind, filled with powerful bliss, seemed to rocket right out of his head and fly over past the moon.

Rarity slid herself upward, keeling over on the cold, wet alley ground besides him. He simply panted, hardly able to think. As the amazing pleasures faded, he leaned over and looked at his wonderful marefriend. Their makeup had smeared all across her face, hooves, chest, neck, and shoulders, looking so silly. His flamboyant lipstick dotted across her fur as well. She smiled. He smiled wider.

She let out a deep breath, leaning totally back against the ground and looking up at the stars. His eyes moved down to the area between her legs. Thick, creamy film oozed out all over her fur. He took a gulp, knowing that he'd never emptied that much into her in all their weeks and weeks together.

"That was... amazing..." she finally murmured.

"Next time," Mac replied, shifting himself up and resting his head upon her chest. "You're the girl."

She smiled.

"Eeeeeeeeeyup," she replied.

The End