D is for Drag, so I warn you, this is the drag that involves men in women's clothing. I was challenged by a friend of mine, who didn't believe I could get Dean into a dress and make it canon. I countered by reminding her that when Sam's the one coercing him, Dean will do... just about anything. Oh, and this :D


Walk A Mile In Someone Else's Shoes

"You are enjoying this way too much," Dean griped, casting Sam what would be a withering scowl under normal circumstances. Which these were far from, so it only caused Sam to smile more as he continued his work.

"Hush, you'll make me mess up and you'll look ridiculous."

If Dean's eyes rolled any harder they'd become permanently lodged in the back of his head. "Oh, God forbid that should happen."

"There," Sam said after a few more dabs, "all done." He stepped back to admire his work and Dean watched as his eyes grew so big they looked fit to pop out of his head. Then, without warning, he collapsed into an uncontrollable gale of laughter. "I… always said you were… pretty enough to be… a girl," he choked out between bouts of laughter.

Furious, Dean turned towards the mirror. 'This… is not real. There is no way in hell my life has come to this,' he thought as he surveyed the damage Sam had inflicted. Glossy lipstick and peach rouge applied to smoothly shaven cheeks coupled with tweezed eyebrows and eyes rimmed in smoky purple and thick black mascara, all put to shame by the wig Sam had tacked on him (rather too well actually, when Dean thought about it). He blew at a few of the deep mahogany-tinted strands that had come loose from the tousled curls Sam had affixed (once again a little too well) and fell across his eye.

"The hell kind of spirit haunts a drag club anyway?" he groused, cursing whatever higher power there may be for his horrendously bad luck.

"One that really likes me," Sam answered, finally able to regain some control. His smile was still wide enough to hurt though. "C'mon, we gotta go, show starts soon and we've gotta be behind stage before the curtain goes up if we wanna kill this thing tonight."

"Yeah, well, hurry up and put on your dress Francine, don't wanna be late to prom," Dean sniped, feeling a little better knowing he wouldn't be the only one using makeup remover after this case was over.

"Oh I'm not getting into drag," Sam answered, smile threatening to split his face in two as he fished for something in his pocket.

"Yeah, right," he scoffed. "Then how do you plan on getting past Kong and Gigantor, smartass?" he quipped, using his rather apt nicknames for the two well-armed seven-foot-something bouncers that guarded the club with an alarming joy of hospitalizing anyone they felt didn't belong.

"Real simple," Sam answered, hand finally emerging with his cell phone clutched tightly, "as a patron."

It took several seconds for his words to process. Then, "Wh- WHAT?" Dean choked, staring down at the clingy dress and heels Sam had wedged him into. "Then all this was…"

"Purely for my entertainment and blackmail for the rest of your life." Sam snapped a photo with his phone and bolted out the door before the after-images even cleared from Dean's eyes.

Dean reached up blindly to pull off the wig, planning on chasing Sam to the ends of the earth if he had to, just as soon as he looked himself again. Only there seemed to be a problem; Sam had apparently glued the wig on…. He ran for the door, his heel catching in the motel's tacky shag carpet, "SAM! GET YOUR ASS BACK HERE AND GET THIS SHIT OFF ME!"