Author's Note

It's amazing how one little screenshot can inspire you to waste so much time on nothing of value like this.

Crossdressing

“Mac, what the hell?”

Caramel had stood there for quite some time trying to think of anything to say when he saw the sight of the… pony before him. He knew very well that it was a stallion, yet the way this stallion was dressed made him stare uncontrollably. His big, broad muscles covered but still bulging from his dress and skirt and large hard hooves concealed in heels seemed to do nothing but scream in his mind “Stallion stallion stallion!” again and again while he stood there in silence, twisting his mouth. His outburst when the stallion went by almost came out without warning, as if he hadn’t planned it by the way even he bit at his lip when he realized just how loud he had snapped.

Caramel looked to either of his sides nervously and saw several ponies on either side of him each staring at the same sights. Now that he had gotten the attention of the red workhorse, who was now moving closer to him with every step all eyes began to draw to him as well. He stood paralyzed, unable to push away the sudden glances that began to fall on him even when he took a step away from the approaching stallion. Something in his chest clenched, and his breath caught in his throat.

“Why, howdy do, mister cutie pie!” The way Big Macintosh's voice was forcibly raised in octaves scraped the inside of Caramel’s ears in a visible cringe that shook his body. He outstretched his hoof to Caramel and held it before him as if he expected Caramel to grab it and kiss it like he was a mare.

The way his lipstick moved and was applied so… perfectly worried Caramel for just how he had managed to apply all of this without fault. True it didn’t fit his body one tiny bit, but it still wasn’t applied shoddily or even thrown together last minute. What worried Caramel most is that this outfit had to have taken time and effort to construct.

Caramel opened his mouth but it was dry. The eyes of stallions around him pierced deeper into him, and nothing he could say would fix it at this point.

“Mac, what the hell?” He repeated dumbstruck. The stallion before him brought his hoof back and covered his mouth, widening his eyes in shock. He covered his face with his hoof in defeat and lowered his head. Mac’s wig looked incredibly fake, so scratchy and almost like hay. “Why are there bows on your shoes? T-That doesn't even go with... anything you're wearing!"

“Why such choice language from a stallion such as yourself!” Big Macintosh reached out his heel covered hoof and bopped Caramel lightly on his nose. Caramel flinched as if he had just gotten hit and his stomach twisted. Ponies kept staring. “Shame on you, darling! And I have to say referring to me as such a brutish stallion is just flat out rude! Mac’s back at the farm getting some rest! Oh I’m positive he’s mentioned me before! I’m Orchard Blossom! Why me and Mac used to play together all the time as kids!”

“Mac can you please just give me an inkling of sanity right now,” Caramel swallowed a lump in his throat. “W-We’ve talked about cross-dressing before, right? Neither of us like doing that, right? I-I know you didn’t lie to me, I can tell when you lie. T-This isn’t even good cross-dressing, that dress doesn’t suit you at all!”

“And why on earth does a stallion like yourself know so much about cross-dressing in the first place?” The… stallion… shook his head and sighed. He gave a smile but the way Caramel instantly glared him down it didn’t reach his eyes and began to look like it ached his face to keep. “I-If I were to guess I’d say you have some very naughty p-private time!”

“Mac!” Caramel snapped. His cheeks were flushing at this point. His outburst had caused even more ponies to look at them. No no no there was just no way he could think rationally right now. “This is just... y-you don't like cross-dressing!” He hissed under his breath and shut his eyes tightly. It didn’t sound completely unreasonable and insane until Caramel had actually said it outloud, but his breathing was getting faster.

“W-Why sugar… darling,” The stallion’s expression only now began to falter. He looked around himself and only now began to notice all the stares he was acclimating. Caramel took another shrinking step away and felt his cheeks continue to flush. “You look more nervous than a… bushel of… thorns… er… Sugarcube?”

Thank Celestia he lowered his voice. He was whispering at this point, but it was still his normal voice.

“Y-Yeah?” Caramel’s voice was growing quieter. He dared to look Mac in the eye for a few moments despite his nerves and felt his mouth go dry again.

“Do Ah really look that bad?” Mac for the first time was frowning and looking at his hooves. He seemed to be examining his heels.

“Why is that what concerns you?” Caramel shook his head and planted his hoof to his face. “L-Look why are you dressed like that? Y-Your makeup is awful... R-Rarity's done work on stallions and they look much better than... t-this..."

“I found the dress in Granny’s room. AJ doesn’t wear too much frilly stuff.” Big Macintosh blinked and Caramel fell to his seat in the grass and covered his face with both hooves. “Granny only wears it on special occasions but Ah thoug-

“I didn’t mean where you got the dress!” Caramel whined. No amount of rubbing his temples would make his headache go away.

“Oh,” Big Macintosh replied.

“Why are you cross-dressing?” Caramel couldn’t help but groan at this point. Normally he was more… collective and accepting, to put it kindly. But the more this conversation lingered the more he worried his heart would burst from his chest.

“Oh,” Big Macintosh repeated. He brought his hoof to his chin as if he had to think about it for a second. “W-Well Ah… Applejack got called away an’ Applebloom was mighty down ‘bout not bein’ able ta compete today. A-Ah thought she would… she would be happy an’...” He kicked his hoof lightly to the ground.

“This… this isn’t about what’s been bugging you lately, is it?” Caramel reached out a hoof hesitantly towards Mac and placed it lightly on part of his cheek which thankfully hadn’t been exposed to makeup. “About Apple Bloom growing up?”

Big Macintosh’s frown deepened visibly. Caramel pulled his hoof away and felt his belly tighten. He bit his lip for a moment when the two remained in silence. Big Macintosh brushed at his skirt a few times which only made Caramel’s chest tighten.

“L-Look… can you just do what you wanna do? I’m not gonna bring it up after this if you don’t wanna. I think ponies here are gonna ask me questions if I stick around, though,” Caramel scratched behind his head. “A-And I don’t know if I wanna watch you do this.”

“Ya don’t think Ah’m pretty?” Big Mac put on a bit of a smile. He was using the voice again.

“Please don’t make me call you ugly,” Caramel giggled and shook his head. “A-And never use that voice again around me.”

“No promises.” Big Macintosh reached into the pocket of his dress and Caramel heard the sound of a few jingling coins. “Hold on just a sec, Sugercube, ya should go get somethin’ ta eat without me.”

“You don’t have t-”

“All contestants please line up in front of the sign up booth to get your number!” An announcer voice boomed throughout the area. Big Mac’s eyes widened and soon he nearly threw the coins into Caramel’s hooves.

“Gotta go, Darling!” Big Macintosh used the voice again and grabbed Caramel’s face on both sides before planting possibly the longest sloppiest kiss he had ever planted on Caramel in his life. When he pulled away Caramel could feel about five layers of lipstick had rubbed off onto him.

“Now I betcha ain’t even been kissed by a mare like that!” Big Ma… Orchard Blossom winked before turning away and brushing his tail against Caramel’s face. Caramel stood dumbfounded for a moment, unable to do anything but wipe at the lipstick now clearly showing on his flushed face.

Ponies were staring at him, but it was a different kind of stare from before. Half of the ponies were looking at him instead of Mac at this point after that stunt.

“I-I need some cider,” Caramel mumbled while looking at the coins in his hoof.