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pickledpascal · 4 months

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Long Story Short, It Was a Bad Time

Pairing: Dean Winchester x Castiel

Warnings: transphobia, homophobia, horrible parent john winchester, homophobic language, implied past prostitution, based on 14x13, angst with a happy-ish ending

A/N: in this, dean is trans and visually looks similar to another of jensen's characters, beau arlen.

Word Count: 4.8k

Jensen Ackles Masterlist

Dean Winchester had known he was a boy since he could talk. Hell, before he could talk.

He wasn't aware he wasn't a boy until after his mother died and every single teacher in every single town they went to called him a girl and separated him into the girls' lines instead of the boys. It got increasingly mind-numbing as he entered his pre-teen years. His first period came around and his dad wasn't sure what to do. Pads were one of the most expensive supplies he had to buy and he never failed to make Dean feel bad about it at every turn.

“Suck it up, Deanna.”

“Don't go tellin’ anyone I don't do anything for you, Deanna.”

“You better clean the garbage out when I get home, Deanna. I don't wanna see that.”

The name itched him like a bad rash. Made him want to scream. But all he could do was cry. After John was gone and Sammy was asleep.

His boobs were growing in and everything about his body felt wrong. He was glad he was naturally tall and that he was able to gain more muscle the more John let him go on hunts but it wasn't the same. His shoulders weren't as broad as the other guys in his class, his hips jutted out too much for his liking, and he hated his long hair.

Dean cut it on his sixteenth birthday and told his father it was under the guise of wanting to be safe. Unpullable hair meant one less thing he had to worry about when it came to monsters. John looked at him suspiciously. He must have known. But he didn't blow up like Dean expected him to. That made the wrenching feeling in his gut twist more. There had to be a catch.

He came out two weeks after that.

“Thank God.” Dean blinked at the reaction. “I thought I was gonna have a dyke of a daughter. Now, I have another son. You going by another name?”

Dean wanted to throw up. Somehow, that made everything worse. His father would rather have a son than a lesbian daughter? He didn't want to think about the fact that he still liked boys just not as much as girls.

He had a few mishaps, he'd look at a few guys as he passed them with John at his side. Dean didn't think too much of it since nothing came of it. Why would John punish him for something as simple as a glance?

Then his seventeenth birthday came.

Dean's first hunt by himself, specifically curated by his father. He watched the fire in the hole he dug earlier with his hands pushed into the pockets of his jacket. The two bodies were as intertwined as they could be for rotting skeletons.

The heat was nice. But bittersweet. He was close enough that it could burn him. Dean would've loved to burn to a crisp as well but he had a brother to protect.

Dean swallowed thickly and gathered up his supplies.

Message heard loud and clear, Dad.

Dean's top surgery was one of the things he remembered the most about his more medical transition. He couldn't get testosterone as much as he wanted to with forged signatures and documents but Bobby offered something else.

So Dean was laid down on a steel examination table asleep on some anesthetic Bobby was able to get off the black market. Bobby didn't have much experience being a surgeon so it wasn't the best but it was as sterile and safe as it could be. But Dean couldn't have been happier. His chest was flat. That's what he cared about. Even if he had to be at Bobby's for weeks. He was just glad Sam was there too instead of having to leave him alone with John.

Time passed. Dean leaned hard into his masculinity after John died. A little too hard.

“You are way out of my brother’s league.”

“Guess how many of these cheerleaders are legal.”

“She's a bitch.”

“Fucking bitch!”

“Bitch!”

Part of it was his frustration with nearly being killed every day of his life, not even by monsters, the other part was the things John beat into him at a young age. If Dean wanted to be a man, he had to be one at John's discretion. He had to like girls but not enough to actually settle down with one. He had to look out for Sam even if that meant he would die.

So he did.

Made a deal. Went to hell.

Except he didn't expect to come back.

That gas station would forever stay in his mind. He walked for hours to find it. His whole body felt a little different. Jumbled around but he could tell his body was still his. He immediately went for the water bottles and broke the seal, downing it in one go.

Dean caught a glimpse of a mirror out of the corner of his eye. He walked up to it and licked at his bottom lip, staring at himself. He noticed his sharper jaw decorated with stubble, his hair seemed to be less chopped, his shoulders more broad, and… he had bowlegs? He looked down and then back up.

Intrigued, he lifted his shirt. His lips dropped open. The scars under his pecs were still there but they were different, no longer botched and scary-looking, but smooth. And his chest. It wasn't completely flat like it was before. His pecs looked more natural, protruding a bit. Like a “real” man. Dean let his shirt drop as he breathed. The handprint on his arm was there too and, for a moment, he knew something cosmic had to be the reason for this, but something inside him felt so happy. Giddy.

He snuck a peak under his jeans. And, yeah, no he still didn't have a dick but he didn't particularly care about that anyway. One of the only things about his body that didn't matter as much. Well, at least now he felt comfortable in himself even if it came at a price.

Over and over again. He was reminded of what he “really” was.

“Daddy's blunt little instrument.”

“Daddy's little girl.”

Hell, half of it came from himself. As a joke. Not one he particularly wanted to be true.

“I've been re-hymenated.”

“Ever since I was a little girl.”

“You got anything that’s real?” “My boobs.”

As Dean grew older, he started to shed those kinds of ideals. Not only did it get too heavy to bear but he started not to care anymore. John was dead. Mary was dead. Who did he have to impress? So he didn't mind talking about the fact he didn't have a dick and indulging himself on some things that may be seen as feminine. Like a few satin panties tucked into the bottom of his drawer or the few times he painted his nails—it never lasted long when he went on a hunt.

Although Dean still thought of his body as a tool, something he could use against their adversaries, it was a little easier to live in when he was in control of what he could do to it. When it was the kind of body he always wanted. So he got more tattoos to cover his body—they were mostly covered by his layers of denim and flannel except for one that creeped onto the side of his neck—his nipples got pierced and he nearly forgot he actually had nerve endings there when it happened, he grew out his hair a bit—not nearly as long as Sam’s but enough that he could style it better—he started wearing earrings and rings again. Not many and usually not during hunts because he had a feeling any monster, or human for that matter, would take advantage of it and tear his ear in half.

Sam and Castiel didn't mention it. Ever. And Dean wasn't sure if he should be grateful for it or not.

“Why did you…” Dean breathed, glancing up at Castiel. He didn't want to finish the rest of his question. It was right after Mary came back and she had locked herself in some random room in the bunker to process something.

Dean was no longer her beautiful, young four-year-old daughter Deanna. He was a grown man with shorter hair, a sharp jaw, and stubble. He knew it would be a shock for anyone, especially someone dead for so long but he didn't expect it to reopen a wound he thought had healed years ago. People had only ever thought of Dean as Dean. A man.

Even the very few women he got with after transitioning still thought of him as a man afterward.

Castiel’s eyes softened at Dean. He could sense the turmoil inside his head. “I was given liberty to rebuild you in the way I thought would prepare you for Micheal,” He admitted softly. He could see Dean was holding in a breath. “I decided to give you the body you wanted. The one you deserved. I had never seen a soul shine as bright as yours as you looked at my handiwork in that gas station. I knew then, I made the right decision.”

Dean's cheeks flared with blush, averting his gaze to look at anywhere but Castiel. He never quite thought about him being there, watching him admire himself. He knew that was Cas, of course, he did, but to Dean, it wasn't Cas just yet. The Cas he knew was so different from that grinding, high-pitched noise he remembered hearing.

The Cas he knew was safe. His best friend. The closest thing to family he had beside Sam. He was able to be open with Cas in a different way than Sam.

More and more shit came and went. More and more apocalypses. But Castiel was a constant. Even if he died a few times. Even if he left a few times. He usually came back. Dean wanted him to stay. For good. But even if he was more open with being a transgender guy and liking girls and guys, he still wasn't that open about his feelings. His more complicated feelings.

“Sam? Deanna?”

That fucking pearl.

The sight of his father. That's not what Dean wanted. That wasn't his deepest desire. Hell, he didn't even know what his deepest desire was. And that name. He hadn't heard that name in years. Mary caught on quickly that Dean was Dean and that was it. But, of course, his father wouldn't. Even if he liked having Dean as a son more than a daughter.

That fucking pearl was supposed to get Micheal the fuck out of his head and kill him for good measure. Instead, it brought him the one thing Dean hated more than anything in his life.

On autopilot, Dean locked himself in his room. He nearly fell to his knees but he braced himself on the wall and had half a mind to punch a hole in it. He winced as that banging in his mind got louder. Micheal screamed. Dean slid down the wall and pushed his hands into his hair. His breathing was harbored and he felt suffocated as if something was weighing down his chest.i

Why did that pearl do that? Dean was happy without him. As happy as he could be with an archangel in his head and tonnes of baggage.

A soft knock brought Dean back to reality. Cas. He pushed himself off the ground and opened the door.

“Sam told me about your father,” His tone was deathly serious. Dean hadn't heard Castiel sound like that in a while. He was grateful for it. “Would you like me to smite him?”

Dean swallowed. The offer was tempting. “Jesus, Cas, no. I—” Want him gone. Dead. Obliterated. Erased from his memories. Back in Hell. Gone from Heaven. Tortured to be forgotten. “I need you. Here. With me.” His shoulders slumped after the admission.

“Of course, Dean. Whatever you need.” Castiel's voice softened as his eyes did as well. It was so truthful, said with such fondness Dean nearly cried.

Dean sat at the end of his bed and motioned for Castiel to do the same. The angel obliged. He knew there was this thing between them. Obvious enough Sam started to call him out on it, never in front of Cas to save him from the embarrassment, but it was always on his mind when they were alone together. He wasn't sure what to do with it. All his feelings. Everything was so complex. Yet simple. It was a strange dichotomy. One he wasn't sure he wanted to admit out loud.

But the fact that Castiel had only ever seen Dean as a man helped. Drove it into his thick skull what this thing was. Love. Castiel spoke to him so reverently. Spoke his name like a prayer. One Dean desperately wanted to hear over and over again.

“Hello, Dean.”

“Of course, Dean.”

“Good things do happen, Dean.”

“This is a good thing, Dean.”

“He called me Deanna,” Dean admitted softly, eyes focused on his boots. He was naturally tall, even before resurrected by Cas, but the boots gave him an extra inch or so to not look as small next to Sam. He could feel how tense Castiel was after his words. “It's… funny,” He let out a dry laugh, “For years, I've been fine. Been good in that area. But that's just—” Dean took a sharp breath. “People see me as a guy now. At least, they do until they get in my pants. But Dad—John, I fucking look like this,” He gestured to himself, “And he calls me Deanna? Fuck me.” He scoffed.

For a second, he had a feeling John only humored him when he was younger. Called him Dean, got him a binder before his surgery, just because it was easier. If Dean became a man then he wouldn't look as much like Mary anymore and then maybe he wouldn't see her in his eyes or his face.

But John still did. This was proof of that.

“Your father, for lack of a better term, is a bitch.” Castiel said shamelessly. “You are so much more than a man born in the wrong body. It's a shame your father is too blind to see that.”

Dean's breath caught in his throat. And then he laughed. Hard. Hard enough his lungs started hurting and he had to gasp for air. Hard enough that tears started to form at the edges of his eyes and a few even rolled down his cheeks. He didn't register his hand on Castiel's thigh until he set his hand on top of it.

Dean pulled it away. Or tried. Castiel held it in place. “Your soul…” He murmured. “It shines so bright when you laugh.”

His voice. So soft and reassuring. Dean screwed his eyes shut. He couldn't help the fluttering in his chest. For the first time in a while, Micheal was silent. It was just him and Cas in the middle of his bed. Safe. Outside his room might be different.

Dean's eyes lifted to meet Castiel's. They were a brilliant shade of blue he couldn't quite place. Nothing matched it. Sure, he could compare them to the ocean or perhaps the sky but even those didn't come close. Without thinking too hard, Dean let himself go.

His free hand pulled Castiel close as he brought their lips together. The surprised noise the angel made was cute and Dean could feel him melting into the kiss. Castiel's lips were chapped, Dean chalked it up to him not caring for his vessel much, but everything felt so right. Their fingers intertwined while Cas threaded his free hand through Dean's hair.

A cough. And suddenly Dean and Cas jumped away from each other. It was Sam. Dean took a breath, thankful that it was Sam and not John. Sam smirked as his eyes flickered between the two men but it was quickly wiped off his face. “Mom and Dad… they want to have dinner together.” He explained, focusing on Dean.

There was still a lot Dean didn't tell Mary about John. About their life before the Men of Letters bunker. What Dean did to survive, to make sure Sam could live as comfortably as possible, to put food on the table and get a bed to sleep on, even while John was still alive. Bathrooms in gas stations on his knees, in the back of bars, dingy motel rooms.

John never asked where the money came from, he took it anyway.

If Mary knew, Dean knew she would look at John in a different light. A part of him didn't want to tarnish that for her. Even though it took some adjusting, she had accepted Dean wholeheartedly. Hell, she only messed up on his pronouns a few times, that was a lot better than when Sam first found out.

“Dean, do you want…?” Sam didn't finish his sentence. He didn't know the full extent of what John did to him but he knew Dean intentionally took the brunt of the abuse for Sam. And he could never take that back. “He's asking about you. Saying you—you finally look like a man. Wondered what kind of work you had done. Thinks you're…” Sam wasn't trying to guilt trip Dean, quite the opposite. “Thinks you get a lot of girls. Asked if you had a wife or something. Asked if you,” He coughed, “Got a dick yet.”

Dean’s fist clenched as his face contorted into disgust. Out of the corner of his eye, he could feel Castiel getting frustrated as well.

Screwing his eyes shut, Michael crept up in his mind again. The screams. The banging. It came back tenfold. “What does he even want? For us to be fucking normal?” Dean huffed.

“Yeah,” Sam said simply. “Dad… he's from 2003. That's what he does best. Act normal when nothing is.” He smiled sadly.

Dean stood up from the bed and rolled up the sleeves to his flannel shirt. He wouldn't—couldn’t—let his father undo everything he had ever built in the last fourteen years of his life. The small little family he made. Sam, him, Mary, Cas, Jack, and Claire. That was his family. Not John.

Castiel looked at Dean, concerned. “Are you sure, Dean?” He could see that little boy inside him, still scared of what his father could do to him. But he could also see the grown man he came to be, unafraid of his father because he could likely overpower him now.

Before he could think about it too hard, Dean nodded. “C'mon, sunshine. I'm not letting him fuck with my head again.” His leg bounced slightly. Not from nerves.

Dean, Sam, and Cas made their way into the war room where John and Mary sat at the map table. John’s head lifted to look at Dean. Fully look at him. Take in his new appearance. When he appeared, Dean didn't stay long enough for John to get a good look at what he had become. The last time he'd seen Dean, he was twenty-five, wore too big clothes, had a skinner frame, and his hair was short and was never styled. This Dean… was not that.

He grew into his height, broad shoulders, visible muscles under his flannel—John would have never guessed Dean was born a girl. That he was his daughter.

“Deanna.” John breathed.

“Dean.” The man corrected. “You're… here.” He wished he wasn't.

John’s eyes narrowed momentarily. Normally, he would've slapped him for something like that but he wasn't stupid. This Dean had a few pounds on him. “I am. Sam and your mom caught me up on everything that went down,” His eyes shifted to land on Castiel. “That the angel that pulled you out of Hell?”

“Hello, John.” Castiel greeted, void of any emotion. Dean glanced at him. He knew the angel inside and out and he knew Castiel was getting increasingly annoyed simply being in John's presence.

Mary sensed the tension between them and coughed. “I was thinking we could have Winchester Surprise?” She suggested softly—ever the peacemaker.

Dean cocked an eyebrow at his mother. He knew Mary was desperate to have John, they didn't have much time together and she was still very much in love, but no one else wanted him there. Dean didn't and neither did Sam and Castiel was so close to stomping John into a curb.

“I'm not sure that's a good idea, Mom.” Dean finally said. As much as he wanted to protect her from the real John, the one who was hiding behind a loving façade, he had to break the news to her. There must always come a time when the veil gets taken away from someone’s eyes, showing them the truth.

John tilted his head and Dean couldn't help but feel it was condescending. “Why not? We're all family here. We can be normal for a night,” He stared at Dean a little too hard. “As normal as we can be.”

“We were never normal,” Dean ground out. It took all his self-control not to just yell at him. Mary looked at Dean worriedly. She'd seen Dean mad, specifically at her, but nothing like this. His shoulders were tense and his nose was drawn into a snarl.

“You–You don't get it. Never will. You suck for a father. I had to raise Sam myself. You'd fuck off to who knows where drunk half the time and make me, a four-year-old watch over a fucking baby. And you liked me better as a son than a girl who liked girls? What the fuck?” Yeah. Fuck that self-control. Dean’s jaw set in place. “Guess fucking what dad? I like girls and boys. And I could care fucking less what you think of—”

Dean's jaw throbbed. Surprise shivered down his spine. John flexed his hand as he stared down at Dean as he cupped his face.

“John!” Mary yelled.

Castiel nearly jumped John before Dean did. With a single right hook, John was out cold on the floor. He flapped his hand afterward, feeling the soreness immediately. It had been a while since Dean had to punch someone, usually, he had a gun or knife when fighting, he was a little surprised at how effective it was.

“Dean!” Mary huffed as she went to John's side.

Dean bit the inside of his cheek. He decided he might as well come out with it. “Fuck him, Mom. He was never my father. He never tried to be. I was the only person who watched over Sam. A tool in his life while he was dead-set on revenge. We could have been normal. If he never went on a rampage.” He looked down at the pitiful heap that was his father with disgust. He glanced at Castiel over his shoulder.

Mary shook her head, trying to reason with Dean. “We're a family. We don't give up on family.” She whispered.

“Sometimes you do,” Dean huffed softly. As much as he and Sam fought, as many times as they took turns dying, it never got so bad that Dean thought he hated him. At least, not for more than a day or so. “I'm good with who I am. Dad isn't. I don't want him in my life. I don't think I ever had but… this is my life now. I get to live it. Meaning I get to choose who's in it,” He swallowed thickly, knowing what he was about to admit. “In ten years time, it's not with him. Never was.”

“Dean, you don't mean that.” Mary sighed. Pleading. She wanted to keep John, make up for lost time.

Sam took a step forward. “Mom, you don't get it either. The shit John put Dean through—put both of us through—no kid should have to go through that.”

Mary huffed, “Then tell me. You can't just expect me to know.”

Castiel stared at her. “Your sons don't have to say anything they are uncomfortable admitting.” He said it as if he was stating the weather forecast.

Dean pursed his lips. Hurt. He knew Mary wouldn't understand but he didn't quite expect this. He turned on his heels and made his way back into his room.

Eventually, everything was as it was. John was sent back after Sam destroyed the pearl and Dean could breathe a little more comfortably afterward. Mary shut herself off from them but he had a feeling that would get resolved as much as the gut-wrenching feeling in his stomach told him it wouldn't. He never wanted to see or think about John ever again. Hadn't wanted to for years after the shit he's gone through.

Dean heard a knock on his door after he got ready for bed. Hell, he was halfway underneath the covers when it happened. He grumbled under his breath, not thinking to put on a shirt or a pair of pants as he opened the door.

“Hello, Dean,” Castiel said softly. As soft as each time before. Dean was suddenly very aware of how bare he was. “Do not be alarmed, it's nothing I haven't seen before.” The angel stepped inside his room, closing the door behind him.

Castiel's words did nothing to ease Dean's beating heart. It felt like a hammer against his chest, wanting to tear itself out of him.

Castiel’s eyes never wavered from his face, studying it as if it were a work of art. He lifted a hand to Dean's cheek. Dean felt as if the air was punched out of him. “I want to know if you're okay, Dean.” Those blue eyes—they never looked at him in pity, never. They looked at him with wonder and understanding.

Dean didn't register the single tear that rolled down his cheek until Castiel's thumb wiped it away. “Not really, Cas.” He breathed. Admitting it didn't feel as bad as he thought it would.

“Why—” Castiel took a breath, saddened by how destroyed Dean's eyes looked. “Why do you think the pearl… gave you John?” He asked softly as he and Dean sat on his bed.

Dean glanced at the corner of his room, lip trembling with a mix of rage and sadness. “Maybe the pearl thought I wanted a Dad. Someone who could love me unconditionally. But I—” He paused sharply, eyes finding Castiel's all over again. He wanted to memorize his eyes as if it were the first time he saw them. Or the last. “I have you.” He breathed. For the first time, Dean hadn't been compelled to add Sam at the end of his sentence.

“You do,” Castiel smiled. And, god, Dean's heart wrenched at the sight. Cas didn't smile, not often. “You always have.”

Dean let out a shaky breath, leaning into Castiel's hand as it caressed his cheek. He sniffled slightly. “Cas, please…. Please promise me you'll stay. Even—Even if I push you away. You,” He was full-on crying now and Castiel was looking at him as if he was the most beautiful thing in the world. “You'll stay. No matter what.”

“I will.” Castiel whispered light as a feather. Two simple words but it was a promise that meant so much to Dean.

It was a promise Castiel never intended to break. Why would he? Especially when Dean seemed so desperate. So distraught. He could never leave Dean. Not again.

“Kiss me.” Dean whispered. Pleaded. He wanted to memorize everything about Cas. The strange body heat he gave off, the tilt of his head, how his lips pressed into a thin line when he was only minorly frustrated by Dean, the roughness of his stubble. Everything.

For the first time, Dean saw a smirk grace Castiel's lips. “Whatever you want, Dean.” He brought their lips together with a sigh.

They kissed for a while, pausing for breath in between kisses but they didn't go past that, ending up with Castiel in bed with Dean after he shed his trenchcoat, shoes, and tie. Dean dozed off, peaceful enough to fall asleep in Castiel's arms.

Even with a fading grace, Castiel didn't sleep much. His body ran well enough on it that sleep wasn't needed. So he stayed up, playing with the hairs on Dean's neck as he watched over him, soothing him as much as possible when he sensed a nightmare coming on.

“You think you're cursed sometimes Dean,” Castiel cooed on deaf ears but he didn't mind. He had to get it out. “That hate is the only thing that drives you. That you're not built for love. But you are. I think, sometimes—no, I know—that’s all you're made up of. And I–I promise we will find a better way,” Cas lifted his hand to Dean's shoulder, positioning it right above his scar. The scar he burned on his skin. “I love you, Dean.” He whispered into his ear.

For the rest of that night, Dean didn't have nightmares. For the rest of that night, he burrowed himself closer to Castiel. For the rest of that night, Michael was quiet.

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