Dean Will Never Bet Again
(1.1 Crossdressing)
AN: I had a Worm fanfiction Bingo Card sitting on my computer for a while so I decided to start using it.
"Fuck you guys," Dean groaned turning to the pile on his bed that Amy had brought over. He stood there in the middle of his bedroom dressed in only his briefs for a moment, wondering if faking an illness would get him out of going to the halloween party later that night. Probably not since Amy was just down stairs waiting for him as she dressed in her own costume.
He glared down into the large clear plastic bag sitting on his bed at the baby blue full length medieval ball gown with included corset, white silk slip and a heap of pretty white petticoats. Next to the garment bag sat a white carboard box with a packaged long black-haired wig, silver and blue costume jewelry, and a matching baby blue hat with a multitude of blue and white feathers; something that very much looked like it came straight out of a history book. There was also, to his vague amusement and slight irritation, a delicate mascarade mask in the same blue, white and silver as the rest of the costume.
After another minute of half-hearted glaring Dean's shoulders slowly slumped and with a sigh he reached down for the slip and the petticoats. A sheet of paper fluttered to the floor when he pulled the gown out to set aside. He picked it up to look over and sighed.
"Well at least they included instructions on how to put this thing on," Dean muttered as he slowly started to read the list. His eyes widened when he read over one line near the top of the page. Grimacing, he reached over under the petticoats and dug around before finding what he was looking for. The padded bra he pulled out was apparently first then the slip. He finally put the page down and pulled the slip closer before trying to figure out the bra.
But slowly, layer by layer, Dean managed to dress in the costume gown. He was surprised to only seriously need help once. His deeply amused mother came up to give him a hand to tighten the corset, allowing the dress to drape properly, then chuckled as she left. He sighed, slipped on the wig and called Amy into the room.
"Ready?" the mousey girl asked, then giggled when she saw him. He enviously noted that Amy had dressed up fairly convincingly as a zombie in tattered and ripped clothes, fake blood splattered across them. "Your wig is a little crooked, here."
Amy helped him to quickly adjust the wig and pin it in place. She also reached over to pull a bag into view that he hadn't noticed before dumping the contents across the bed, revealing more cosmetics than he'd ever seen outside of a store.
"This is Vicky's make up bag." Amy chuckled, she was more amused than he had seen her in months while Dean just blinked. He was a bit stunned as Amy pushed him down into his computer chair and set about quickly applying different cosmetics to his face.
"Was this bit your idea or Dennis'?" Dean asked after Amy finished coating his lips with a dark red lipstick.
"Mine," Amy said cheerfully. "It just completes the costume so well. Besides Dennis wants to see how many guys will flirt with you at the party. I'm thinking Chris will hit on you first, but Dennis thinks it'll be Carlos. Sister dearest just wants pictures since she's grounded and can't go to the party."
Dean grimaced, "I'm never betting with you guys again."