I actually updated the cover art for this, what do you think? I got a request for a 4 part cross dressing one shot, which gave me this cross dressing idea, and I wanted to try out a cross dressing fic before doing the request. There's smut and bottom Dean. (I love bottom Dean)
Dean looked at himself in the mirror. He felt ashamed and dirty, but at the same time, he felt free and sexy. It was confusing. The hem of his black skirt just barely touched the top of the thigh high fishnets he was trying out. He pulled a black cropped tank top on over his head. The end of the tank top left a strip of skin showing before the skirt began. He again studied himself. He thought he looked like a stripper, but he liked the look.
Sam's footsteps could be heard coming back to the bedroom he was in. He quickly went to the bed and climbed in, pulling the covers over his shoulders to cover up what he was wearing. Sam opened the door. He immediately saw Dean and gave him a weird face.
"Are you cold?" Sam asked.
"Yeah, aren't you?"
Sam came around to the opposite side of the bed Dean was in. Dean watched calmly as Sam stripped down to his boxers. Inside he was freaking out.
"What are you doing?" Dean asked nervously.
"I was going to cuddle with you to warm you up."
"No, no, it's okay. I'm fine."
Sam gave Dean another weird look, "Are you sure you're okay? You're acting off."
"I'm fine, Sammy."
Sam pulled up the bedcovers and crawled into bed next to Dean. Dean made sure to hold the cover down on his side so Sam wouldn't see what he had on. I guess I'm sleeping in his now, Dean thought.
Somehow, Sam manage to slip his arms around Dean. He could feel Dean's skin, and two pieces of material.
"Dean? What the hell are you wearing?" Sam asked in amusement.
"Promise you don't judge me," Dean said.
"I love you, Dean. I wouldn't judge you for anything."
Dean took a deep breath before removing the bed clothes, allowing Sam to see his outfit.
"Dean," Sam said breathily as he took in his older brother. Slowly, he ran his fingers up the fishnet thigh highs, as if making sure Dean was really there.
"You said you wouldn't judge," Dean said.
Sam was breathless, "How could I judge you for this?"
"Because it's weird and shameful."
"Dean, you look gorgeous, and you can't let anyone tell you different."
Sam leaned down to kiss Dean's lips. Dean pressed against him, wrapping his arms around Sam's neck. He could feel Sam slide his hands up Dean's leg until he reached the hem of the skirt Dean was wearing. Suddenly, Sam broke the kiss.
"I couldn't help but notice that the skirt you're wearing is way too short to have your normal boxers on," Sam asked with a smirk.
"Sammy, are you asking what underwear I'm wearing?" Dean asked in a sensual voice. "Why don't you feel for yourself?" He took Sam's hand and guided it underneath his skirt. He failed to hold back a moan as Sam touched him.
"Are you wearing a thong?" Sam asked in surprise.
"Do you want to see it?" Dean smirked.
Sam slowly removed Dean's skirt to reveal the lacy black man thong Dean had on. He watched as lust filled Sam's eyes. Without saying anything, he leaned down and began to kiss Dean again. This time, the kiss was more rough and passionate. Sam wrapped his arms around Dean and pulled him up with him as he sat up on the bed. Dean wrapped his legs around Sam and pressed his body against his brother's. Sam broke the kiss once again; this time to rummage in the bedside drawer to find a bottle of lube. Once he found it, he turned back toward Dean and removed the older Winchester's crop top and thong, and his own boxers.
"Ready?" Sam asked.
"Always," Dean smiled.
Sam kneeled in front of Dean, his brother's legs on either side of him. He slowly slid one lubed finger into Dean. Dean grimaced for a second, but quickly began to squirm pleasurably under his brother's touch. He gasped as Sam leaned down to kiss Dean's inner thighs. Dean let out a loud moan as Sam suddenly put his mouth on Dean's dick and shoved another finger into him without warning. Sam slowly took more of Dean into his mouth as he pressed his fingers in and out of Dean's entrance repeatedly.
"I'm ready, I'm ready," Dean said breathlessly.
"Are you sure?" Sam asked, uncertain.
"Just fuck me already, Sammy," Dean begged.
Sam sighed, but complied with Dean's request. He removed his fingers, picked up the bottle of lube and rubbed some of the substance onto his own cock. He wiped his hands on his discarded boxers. Then he lined himself up with Dean's entrance and slowly pushed himself in, allowing Dean to tighten his legs around Sam. Dean moaned as Sam entered him. Sam watched as Dean tried to hide a pained face. I knew he wasn't quite ready, Sam thought to himself as he let Sam adjust.
"Move! C'mon, Sammy," Dean pleaded.
Sam began to slowly thrust into Dean. He moaned as he felt his brother around him. Dean reached up and pulled Sam down to kiss him. He ran his fingers through Sam's ever growing hair, loving the feeling of the strands between his fingers. He didn't notice that Sam was moving so that he was able to pump Dean's member in time with his thrusts, which were picking up speed. Suddenly, a rush of pleasure ran through Dean. He arched his back and moaned as it hit him. Sam knew, by Dean's reaction, that he'd finally found Dean's prostate. He angled himself and began rushing at the same spot over and over again, until Dean couldn't take any more. He finally came into Sam's hand and onto both of their stomachs. Sam followed mere moments later.
Once they both rode out their orgasms, Sam pulled out of Dean and collapsed next to him. He was breathing heavily, unable to catch his breath. Dean wiped both of their stomachs and Sam's hand off with a tissue. Sam wrapped his arms around Dean.
"I'll always love you, no matter what you wear," Sam whispered, but Dean was already half asleep and didn't answer. I'll tell him in the morning, Sam thought tiredly as he joined his brother in sleep.