Yeah, I'm a little late, and this is a little short; I'm sorry. This picture kinda hit me hard though, I was just thinking the same thing a few days ago.
Suggested by: princess_lolita99
Dean sighed, "Guys, there's something I need to tell you."
Cass and Sam waited expectantly.
"I like to wear women's clothes sometimes."
"Do you have more on?" Sam asked with a smile, causing Castiel to smack his should and say,
"Don't be mean!"
"I'm also wearing a t-shirt," Dean admitted.
"Take off your flannel," Sam said. Dean complied. He couldn't help but notice that both Castiel and Sam stared at him for a couple seconds.
"Well, it is a lot less boxy than men's shirts, so it shows off your muscles and shape better," Sam observed. Both Dean and Cass looked at Sam in shock.
"What?" Sam asked, "I'm just being supportive."
Dean tried not to let any disappointment cross his face. He didn't want to accidentally admit that he always found Sam and Castiel attractive.
"So you guys don't think I'm weird? Or that this is all weird?"
"You're my friend and Sam's brother; we love you, Dean, and we'll always accept you," Cass said with a smile.
Sam nodded in agreement, "You can dress however you like around us."
Dean was relieved to know that he could finally be himself around Cass and Sam. He decided he no longer was going to be careful of what he wore when he was with him.
A few days later Sam and Cass came back from another food run to see Dean dressed in a pair of short denim shorts, a tighter tank top, and of course, the pink satin underwear that started everything. When Sam and Cass walked through the door, they seemed to take a second to regain their thoughts.
"Is that new?" Sam asked. Dean swore he saw his brother checking him out as he said it.
"Not really. I've had these pieces for a while, and I'd always thought they'd look good together, but I was always too afraid to wear it."
"Well, you look good," Cass said. Then he looked at Sam, "You're not the only one who can be supportive." They seemed to share a look that was missed by Dean.
A couple weeks went by with the same routine, until finally Sam and Cass decided it was time to tell Dean a secret of their own.
"Dean," Sam said. He bit his lip as Dean turned to face him and Castiel.
"Is something wrong?" Dean asked, sensing the tension in the room.
"No, we just have something we need to tell you," Sam continued, glancing at Cass. Cass gave him a small nodded.
Sam sighed, "Well, ya see, Cass and I..." Sam trailed off, not knowing how to tell Dean. His face reddened as he dragged the sentence on.
"We want to come clean about a crush we both have, on you," Cass interrupted.
Dean was shocked, unable to talk. He was never actually sure if Sam and Cass felt the same about him as he felt about them. Now the moment he'd been waiting for was actually happening, and his brain was shutting down, unsure how to react or what to say.
