Sam and Dean had both done it when they were younger. John would never have made his sons pretend to be his daughters, but every now and then it was necessary for getting the right kind of intel on a hunt or, even more common, when the authorities caught up with John. No matter how many fake IDs or sudden moves the Winchesters took, there was usually a trail of dead bodies and of truancy problems regarding the boys. So every now and then, John rolled into town with his daughters Samantha and Deanna until the coast was clear. Dean did as he was told as always, but he hated it – always had, always would. He'd been teased mercilessly prior to adolescence for being pretty. He didn't need a fucking dress to make it worse.
Sam, on the other hand, complained very little, a rarity for Sam when John issued any order. Dean teased him about it and Sam would pretend to get pissed off, pouting in the backseat of the Impala, but by the time both he and Dean were adults, Dean knew all too well just how much Sam had enjoyed it.
“Dad's gone. Aren't you gonna change?” Dean asked with a smirk. It was Saturday, which meant no school for Sam, and John had left on a hunt hours ago. It had been a long time since Sam sat around the motel room wearing baggy jeans and a hoodie when John wasn't around.
Sam just shrugged, turning the page in his math book that he seemed very intent on re-reading. Dean had told Sam he should have dropped out once he was sixteen. Sam could have gotten his GED with no trouble (unlike Dean who had to take it three times) and be done with the whole thing, but Sam refused. He liked school. Dean knew he wanted to go to college, but he hoped it wouldn't come up even though Sam was eighteen now with less than a month left of school.
“Great,” Dean mumbled. “So you're just gonna sit there and pout all day? That'll be a blast.”
“Dean...” Sam rolled his eyes.
“Dad hasn't left us alone in like a month,” Dean said sidling up beside Sam on the bed. He ran his hand along Sam's abdomen, unbuttoning his pants and slipping his hand inside. “I had plans.”
Dean thought maybe Sam had outgrown his enjoyment of playing dress-up. It wasn't unheard of, but it seemed unlikely as Dean's fingers brushed over a pair of silky panties trimmed with lace. Sam didn't push Dean away. He closed his eyes, letting the book fall onto his chest
“P-plans?” Sam forced out as Dean teased his cock.
“Wanted to take you out, dinner, a movie, but if you're not in the mood,” Dean pulled his hand away and stood up, moving to the other bed. Sam let out a frustrated sigh and threw his book aside.
“You wanna take me on a date?” Sam said a little surprised. Sam had never even left the room dressed like a girl outside of those times it had been for a case. Certainly not since it had taken on a sexual component with Dean.
“Wanna take Samantha on a date,” Dean corrected. It wasn't that he didn't love Sam as he was, but Samantha was something that belonged just to them now. “Please, Sammy, don't sit here sulking like an emo bitch for whatever reason.”
“I can't, Dean,” Sam frowned again.
“We'll go to the next town over,” Dean pressed the matter. “No one 'll see you, if that's what you're worried about.”
“I don't care about that,” Sam could easily kick any little prick's ass at school that saw him in a dress and made fun of him. Dean wouldn't stand around and let Sammy get picked on, either. They'd move on soon enough anyway. “The clothes we bought in Indiana. They don't fit anymore.”
That was over a year ago. Sam had been still been under six feet then. The last two growth spurts the boy had were massive. He'd caught up to Dean and the kept going. There weren't a whole lot of girls 6' 4”. Sam had browsed around a J.C. Penney while Dean and John were off on a hunt, but there wasn't a damn thing that was going to fit him without looking ridiculous. He was still thin, toned, but not overly muscular despite John's insistence that he weight train harder.
Dean slid over on the other bed making room for Sam and motioning for his younger brother to join him. Sam curled around Dean's side, head resting on his chest.
Dean/Sam, crossdressing + attention (PDAs), Hard R, 1/3
Sam, on the other hand, complained very little, a rarity for Sam when John issued any order. Dean teased him about it and Sam would pretend to get pissed off, pouting in the backseat of the Impala, but by the time both he and Dean were adults, Dean knew all too well just how much Sam had enjoyed it.
“Dad's gone. Aren't you gonna change?” Dean asked with a smirk. It was Saturday, which meant no school for Sam, and John had left on a hunt hours ago. It had been a long time since Sam sat around the motel room wearing baggy jeans and a hoodie when John wasn't around.
Sam just shrugged, turning the page in his math book that he seemed very intent on re-reading. Dean had told Sam he should have dropped out once he was sixteen. Sam could have gotten his GED with no trouble (unlike Dean who had to take it three times) and be done with the whole thing, but Sam refused. He liked school. Dean knew he wanted to go to college, but he hoped it wouldn't come up even though Sam was eighteen now with less than a month left of school.
“Great,” Dean mumbled. “So you're just gonna sit there and pout all day? That'll be a blast.”
“Dean...” Sam rolled his eyes.
“Dad hasn't left us alone in like a month,” Dean said sidling up beside Sam on the bed. He ran his hand along Sam's abdomen, unbuttoning his pants and slipping his hand inside. “I had plans.”
Dean thought maybe Sam had outgrown his enjoyment of playing dress-up. It wasn't unheard of, but it seemed unlikely as Dean's fingers brushed over a pair of silky panties trimmed with lace. Sam didn't push Dean away. He closed his eyes, letting the book fall onto his chest
“P-plans?” Sam forced out as Dean teased his cock.
“Wanted to take you out, dinner, a movie, but if you're not in the mood,” Dean pulled his hand away and stood up, moving to the other bed. Sam let out a frustrated sigh and threw his book aside.
“You wanna take me on a date?” Sam said a little surprised. Sam had never even left the room dressed like a girl outside of those times it had been for a case. Certainly not since it had taken on a sexual component with Dean.
“Wanna take Samantha on a date,” Dean corrected. It wasn't that he didn't love Sam as he was, but Samantha was something that belonged just to them now. “Please, Sammy, don't sit here sulking like an emo bitch for whatever reason.”
“I can't, Dean,” Sam frowned again.
“We'll go to the next town over,” Dean pressed the matter. “No one 'll see you, if that's what you're worried about.”
“I don't care about that,” Sam could easily kick any little prick's ass at school that saw him in a dress and made fun of him. Dean wouldn't stand around and let Sammy get picked on, either. They'd move on soon enough anyway. “The clothes we bought in Indiana. They don't fit anymore.”
That was over a year ago. Sam had been still been under six feet then. The last two growth spurts the boy had were massive. He'd caught up to Dean and the kept going. There weren't a whole lot of girls 6' 4”. Sam had browsed around a J.C. Penney while Dean and John were off on a hunt, but there wasn't a damn thing that was going to fit him without looking ridiculous. He was still thin, toned, but not overly muscular despite John's insistence that he weight train harder.
Dean slid over on the other bed making room for Sam and motioning for his younger brother to join him. Sam curled around Dean's side, head resting on his chest.
“Sorry, Dean,” Sam mumbled. “Woulda been nice.”