Guys! I won the scholarship from my church that I mentioned last week, and I didn't add a picture this time because I couldn't find any pictures of Dean crossdressing that I liked.
Suggested by: princess_lolita99
Dean couldn't help but smile to himself as he got dressed. He was pulling on a pair of satin feeling ladies underwear that just barely covered his plump bum. Then he put on a pair of well fitted jeans that just barely gave away his shapely thighs. Then came on a women's fit t-shirt to show off his muscular arms, yet thin shape. Over the shirt, he put on one of his well known flannel shirts. He just wasn't ready. Wearing women's clothing was Dean's secret to himself. It gave him a lot of confidence, but he just wasn't ready to share his secret to the world. Hell, he wasn't even ready to show Sam or Cass. He did notice, however, that when he did dress the way he liked, Sam and Cass seemed to notice him more. Maybe it was all in his head, though. Perhaps his crushes on both boys were beginning to get out of hand, and he was projecting his feelings onto Sam and Cass in hopes that someday he would finally get to be with both of them.
Just as he was buttoning the last couple buttons of his flannel, Sam and Castiel came into the motel room, laughing about some inside joke.
"Morning, Dean!" Sam said happily, "I got breakfast." Sam sat two take out bags on the table.
"Hi, Sammy," Dean said, slightly nervously. He cut it really close this time. Usually when he decided to wear women's clothes, he allowed for plenty of time so that he wouldn't be caught.
"Hello, Dean," Cass said in his deep voice.
"Cass," Dean replied, unable to hide the smile that appeared on his face. The angel's voice never failed to make him melt.
Sam and Dean sat down at the table to devour the breakfast sandwiches that Sam brought home. Cass, since he didn't eat, sat with them and watched them eat. They quickly finished to get on to the next case, which was two states over. They quickly packed a couple last minute things. Dean leaned over to make sure nothing had fallen beneath the bed when Sam asked.
"Uh, Dean, why are you wearing pink underwear?"
Dean quickly stood up, pulling down his shirt to hide the waistband of his underwear.
"What are you talking about, Sammy, I don't have any pink underwear."
"Dean, don't lie to me. I know what I saw. You're wearing a pair of pink satin underwear."
Why was he even looking there? He doesn't like me in that way, Dean thought, blushing.
"I saw it, too, Dean. You don't have to hide anything from me or Sam," Cass said.
Dean thought for a second, his face getting redder. He didn't know how to get out of his one. His mind went blank on what to say. How could he? He'd been caught red handed, and there was no getting out this time. He'd have to come clean.
