Author's Note: I've been wanting to write trans!Dean since I saw my first episode of Supernatural, and an idea similar to this one popped into my head weeks ago. The original story was a bit more pornographic than this. But I ended up wanting to be a bit more introspective. Maybe later I'll write the porn. Deanna 'Dean' Winchester was FAAB and is a transman with no surgery. (Like me) He prefers masculine pronouns and is referred to as he, him, and himself. I hope you enjoy reading this as much as I enjoyed writing it.

Clothes Don't Make the Man

Dean Winchester was not posturing. The car, the classic rock, the leather jacket, the greasy food, the booze, the girls. Well maybe with the girls. The other things were all real though. Deanna 'Dean' Winchester did enjoy Pink Floyd, and Styx, and Kansas. He could make the motor of the impala run like a dream, and could drive for hours. Besides hiding errant curves, layers and layers of flannel and leather were warm and comforting. Even the girls were okay most the time. The girls who knew, and the guys too. (Just because you are a man, doesn't mean you have to be a hetero one) It was sometimes hard to explain how you were a man when the evidence of your partner's eyes and hands were telling them otherwise. Being drunk made it easier. But Dean didn't want to change much about this body. It was a good body, a strong body. And whatever it looked like would not make Dean any less of a son, a brother, or a man. No, there were few things he wished to change. But breasts were something he did.

He considered ordering a binder, but that was hard when they had no permanent address. Instead he found a tutorial online and bought a bit of canvas cloth. He made his own binder. It was heavy and made him sweat and he had to wash it every night, but it worked. There was a small swell were his bosom was, but with adjustment it looked like pecs instead of breasts. Dean gave thanks every day to God or whoever was responsible that puberty had been kind. Dean was tall, not the way Sammy was tall, but nearly six feet, and a bit over that wearing boots with a walking heel. He was also slight with barely there hips and a small bust. He had thought and rethought surgery a thousand times and decided against it. Something about the permanence, the scars, the hormones, the fact that it could only bring you so far was unappealing. Dean was a man and always had been. He would have been happier being born in a male body, but this one would do just fine.

So no, the clothes were not just an act. The comfortable flowing male clothes with their soft double napped cotton, tailored to make his waist look narrowed and masculine, and rows of buttons on the right side weren't a costume. Nothing was as comfortable as sleeping in boxers and socks, way better than women's underwear always mashing all the bits together and stuck in your ass crack all the time. Dirty boots to dirty jeans to short dirty fingernails, and at least three layers and a jacket. And the hair. The hair was the best part. Long natural hair everywhere but his head. One of the greatest feeling in the world was having a pretty lady with her first in your hair taking the clippers to the back of your head until its short and prickly and your neck is cool. He knows he is lucky to pass so easily. His jaw just square enough, chin slightly cleft, his hair immaculately styled. He had to be careful or his big green doe eyes, thick dark lashes, and pursed lips would give him away. Sam sometimes called it his 'male model look'. Dean had to admit it was pretty funny and knew he could make his brother laugh just by pulling a quick face.

Sam seemed to understand, and never had a problem calling Dean his brother even when everyone else was still calling him Deanna and stuffing him into ugly itchy dresses. Everything had been well and good until Sam was born. John Winchester let Dean run wild and do all the things boys did. Taught him to fish and play catch and win in a fight. Then Sammy came along and John had a real son to teach things to and Dean was left to learn how to become a lady. The word felt almost like poison. Lady was the opposite of all Dean's favorite things. Ladies didn't belch, or play stick-ball, or sit with their legs spread like a boy. They demurely crossed their legs at the ankle. After Mary died it was even more important to John that Dean be feminine, as if he were hanging on to Mary that way. That lasted until Dean was eight and took a pair of scissors and cut off the braid that had previously been down to his ass, and a constant heavy reminder of his imposed femininity. John found it curled up in the hotel bathroom trash bin in the morning like a dead snake. Deanna: 1 John Winchester: 0

Things went a little better after that. Dean dressed himself in what ever clothes he wanted, wore his hair short, and was chided less for being unladylike. Deanna had been daddy's little princess, had been beautiful and good and all the things girls should be. Dean was not those things, and he pushed them off on her, on the person Dean had never been. That was obvious from his answer to the question adults always asked children. What do you want to be when you grow up? Dean's answer had always been the same. I want to be a boy. Eventually John let him. Dean thought uncle Bobby may have had something to do with it. Convinced him that it wasn't hurting anyone, Deanna was just being a kid. Only John was surprised when he didn't grow out of it. Not to say Dean and John Winchester butted heads often. Dean did whatever John asked, protected his brother, learned to hunt, gave up everything for this life. Eventually John was gone, from then on he was just Dean Winchester.

Then there was Castiel. Castiel, who told Dean in no uncertain terms that he knew Dean's body as well as anyone could know a body. Who had known it intimately when the angel put it back together after hell. When he stitched it back together using a thread of grace. Angels don't have a gender, angels disregard sexual orientation. Vessels were gendered, but they didn't see much action. Cas made it easy to stop thinking about being a gendered body, and instead just think as a mind. Shone a holy light on all the bad things that hide there in the dark. Had caught Dean more than once without the binder, without Sam, without any other piece of protection. Had told him in his odd angel way that he loved him, body and mind. He was the one who gripped him tight, and for awhile Dean bore his sign burned into his arm. Castiel had covered every inch with hands and teeth and tongue. And in his own way Dean was in love with Cas too. In love with this ethereal being who knows him so well. So Dean was a man, a brother, and in love with an angel. Dean Winchester was not posturing...

Well, maybe with the girls.