On the second day, Dean found out that Bruiser would take a mouthful of food out of his bowl, spit it out two feet away, eat the pieces one-by-one, and then go back to the bowl to repeat the cycle.

Bruiser wouldn't eat treats that were green Dean found out on the fourth day.

Sam discovered when he came to visit on the fifth day that Bruiser had stolen Dean's used work socks and hid them under the couch. Unfortunately, the way he found out was when he went to retrieve the ball they had been playing with from under said couch and pulled out one of Dean's crusty socks instead. Dean thought Sam's face and screech of despair was hilarious at the time until he discovered the other 9 socks hidden under the couch.

All these quirks were manageable and, frankly, a little cute if Dean were being honest. Sam and Dean had discussed them each at length and they couldn't believe Bruiser was as much trouble as the shelter seemed to think he was. Dean didn't understand how two families had returned Bruiser after less than two weeks in each home.

Until Day 6: Trash Day. Then, Dean understood.

"Dude, you need to come over after work. It's Bruiser. I don't know how to explain it."

"Is he hurt?"

"No, he seems fine now."

"What happened?"

"This is gonna sound crazy."

"Just tell me, Dean."

"He attacks trash cans."

"He attacks trash cans?"

"Yes dude! We were walking on the sidewalk and then out of nowhere he hurls himself at a trash can and knocked it over. Like a full body slam. I pick it up and put it back just thinking that was weird and a one time thing but he did it three more times before I dragged him back home."

When Sam came over three hours later, Dean was waiting onside on his front step absent-mindedly scratching Bruiser's head with one hand and holding his leash with his other. Dean silently handed Sam the leash when he approached and held up 1 finger as a signal to wait. Dean dragged his large green recycle bin from it's location in the garage near the Impala to the middle of the driveway.

"Try to walk past it."

Sam thought his brother had been exaggerating but when Bruiser went to pass the recycle bin by something shifted. Bruiser rushed forward, tugging at the end of his leash, and launched himself at the container in what could only be described as an All-American football tackle. The bin toppled over a few feet from where it sat originally and Bruiser continued on like nothing had happened.

That "quirk" was the reason Bruiser had been turned into the shelter the first time and returned both times the receptionist told Dean when he phoned the following morning. His first owner thought it was hilarious when Bruiser did it as a puppy and encouraged it for a long time. When Bruiser reached 60lbs, it apparently lost its charm and took him the shelter when he wouldn't stop. Both of Bruiser's adopters thought that this quirk was just too much on a list of weird quirks and brought him back after short stays. The shelter receptionist said they didn't know how they were going to get him adopted at this point with his track record.

When the receptionist asked Dean when he would like to return Bruiser, Dean said he wasn’t planning on it. That was the truth. He never planned to return Bruiser to begin with but he had called the shelter looking for answers. After hearing more about Bruiser’s life, Dean knew he couldn’t abandon the poor guy like all the people did before.

Dean enjoyed snuggling on the couch with Bruiser after a long day at the fire station. Bruiser didn't destroy the house or have accidents when he went to work. Bruiser waited by the bathroom door for him every night while Dean showered before stretching out beside him on the bed. Sam adored him and Eileen loved his slobbery kisses. They loved coming over Saturdays to walk him while Dean worked his longest shift of the week. Sue him, he grew attached to the big lug and his quirks.

And wouldn't you know it, the neighborhood grew attached to Bruiser and his quirks too.

Every Wednesday, neighbors would move their trash cans and recycle bins to the curb for trash day. Every Wednesday evening Bruiser would tackle every trash can and recycle bin he would come across on his evening walk. Dean would hastily collect anything that fell out (trash and recyclables were collected in the morning thankfully but sometimes one or two were accidentally skipped) and right the trash can. Well, as much he could anyway. Bruiser would tackle it immediately once it was upright again.

Three weeks after adopting Bruiser, the neighborhood kids would gather to watch Bruiser demolish trash cans. Some would even walk and chat with Dean to witness the destruction up close.

Two months in and it was practically a weekly neighborhood event with Bruiser and an embarassed Dean serving as entertainment. Neighbors would come out to their front steps to watch Dean and Bruiser on their path of destruction. It was unusual but most people seemed to enjoy watching the bulldog in his element.

One of his neighbors even painted a bullseye on the side of his trash can.

Dean did try to avoid the bins at first but both sides of the street were lined with cans and bins. He tried every trick and tip he found online but Bruiser could not be swayed, bribed, or persuaded not to tackle. Dean even tried walking down the middle of the street which caused him to have to pull/drag his slow-moving bulldog out of the way every time a car came and Bruiser would tackle the closest bin anyway.

Only once did Dean not take Bruiser on his evening walk on trash day and it was then that he discovered another one of Bruiser’s “quirks”. When the bulldog had figured out he wasn’t getting a walk that evening, he started screaming bloody murder and did not stop until Dean picked up the leash.

Four months after adopting him, Bruiser found his sworn enemy at a newly purchased house just four doors down from Dean. The flimsy, yellow recycle bin with yellow bees and the quote "Bee Friendly!" painted on the side deserved the wrath of God Bruiser had decided. Bruiser didn't just want to tackle this bin. He sought to destroy it.

The first week, Bruiser tried to drag the recycle bin from the curb after tackling it. Dean fought to extract it from Bruiser's mouth and had to carry Bruiser away much to the delight of everyone watching.

The second week, Bruiser did the same but this time he tried to run away with it and Dean had to trap Bruiser between his legs to free the poor bin.

The third week, Dean walked on the other side of the street but Bruiser still growled as they passed.

The fourth week Bruiser succeeded in his mission. Which is how Dean found himself in his current predicament.

Dean would never let Bruiser destroy someone else’s property on purpose and steered clear of neighbor's trash cans and recycle bins who didn't enjoy Bruiser's antics as much as the rest of the neighborhood. But today had been a practically long day at the station. He had been called in for an emergency hours before his shift was scheduled to start. He is more tired than usual on their evening walk and isn't paying attention as Bruiser plows through the first neighbor’s plastic trash bin with glee. He didn't even change out of his station t-shirt because he had made plans with Sam and didn’t want to miss Bruiser’s evening walk.

It was only after Bruiser launches himself at the yellow bee bin and manages to crush it with a single, well-placed tackle that Dean remembers Bruiser’s hatred for the thing. Bruiser, satisfied his foe had been vanquished, picks up a large piece with his mouth and starts walking away like he had just successfully hunted a gazelle on the Serengeti.

Dean knew that something like this would happen eventually but did it have to be with a neighbor he hadn’t even met yet? He feels his pocket for his wallet and prepares mentally to write a check to replace the bin while apologizing profusely.

Dean checks his watch and realizes that he was going to be late to meet Sam back at the house. Sam had arranged a blind date/double date with Eileen, Dean, and a mysterious stranger. According to Sam, he doesn’t get out and date enough. Spurred by the success of getting Dean to adopt a dog, Sam had decided the next thing he would fix is Dean’s love life. Sam talks a lot so it didn’t take him long to secure him a date. Dean shoots off a quick text telling Sam what happened and promises to be home soon.

He stalls for a few more minutes while he thinks about what he wants to say. It’s probably going to be something along the lines of Please don’t call the cops on my asshole dog. He likes to tackle trash cans because his first owners were idiots. Here’s a check for 100 bucks.

Finally, Dean can’t avoid it anymore. He gathers the remains of the yellow bee recycle bin and walks Bruiser up the pathway of the two-story family home. After knocking on the front door, Dean is greeted by a pair of bright blue eyes and messy hair.

Dean stands there staring at the man in front of him. The man had obviously just gotten home from work because he is wearing a tan trenchcoat and suit. His tie is backwards and pulled down away from his neck. The man glances down at Bruiser and seems to notice what the dog was carrying in his mouth. He then smiles at Dean and Dean feels his brain short circuit.

"Hello, Dean. I take it you’re here because your dog was finally able to destroy my recycle bin?"

Dean is shocked. He has never met his new neighbor so how did he already know his name? Dean would have remembered meeting someone that looked- well like that.

"Yeah," Dean starts, clearing his throat, “Sorry, about that. I-um- well Bruiser- wait no- I’m sorry that my jerk of a dog-”

The man continues to smile as Dean fumbles through his apology. He steps onto the front steps and closes his door behind him with a soft click. He is only a few inches away from Dean as he bends down to say hello to Bruiser.  

For as much as Bruiser hates the man’s yellow bee recycle bin, he sure seems to like this guy. Bruiser sits immediately within the man’s reach and happily leans against his leg to get attention.

“My name’s Castiel by the way but you can call me Cas. It’s nice to finally meet you. I’ve heard a lot about you from Sam.”

“You know Sam?”

“Yes, he and Eileen stop by with Bruiser to chat on Saturdays when I am working in my front garden. I’ve heard all about Bruiser’s escapades including his hatred of my recycle bin.”

Sam never mentioned meeting his new neighbor but then again sometimes Dean didn’t always listen the best after his double shift. Usually, Sam would drone on and on about how great Bruiser is, the boring cases at his law office, and that Dean needed to get out more. Most of the time Dean would try to listen before zoning out and nodding occasionally.

“Cas, I really am sorry about all of this. Please let me pay for the replacement.”

“I have a better idea,” Cas says as he stops petting Bruiser and straightens up. He meets Dean’s eyes with an intense stare before continuing.

“You can buy me dinner tonight instead.”

Yep, Dean’s brain is well and truly fried.

“Yeah sure, I can totally buy you dinner. Wait not tonight. I kinda agreed to this thing with Sam... So raincheck maybe?” That was as smooth as crunchy peanut butter, Dean thinks to himself.

Cas smiles even wider, “Good to know you weren’t going to skip out our date tonight. Sam warned me that you were unsure if you wanted to go at all but now that you owe me dinner, I’m almost positive that you’ll show up.”

“You’re my date tonight?”

“Yes. When I mentioned I was single last weekend, Sam asked if I would be interested in joining him and Eileen on a double date with his ‘single, firefighter brother who has a cute dog.’ You can, of course, back out if you are uninterested now that we’ve met.”

Dean had only recently come out as bisexual but trust his little brother to ally-up right away and secure him a date with the first single, attractive man he stumbled upon. Not that Dean is complaining.

“Cas, I would love to buy you dinner tonight and not just because of Sam- or Bruiser.”

Cas accompanies Dean and Bruiser for the rest of their walk after disposing of the remains of the murdered recycle bin. Bruiser carries his stolen piece of the yellow bee recycle bin with great pride and only knocks the occasional trash can over as they make their way back to Dean’s house. Conversation flows easier the more they talk and they seem to hit it off. Cas laughs as Dean works to straighten up the bulldog’s path of destruction and Dean laughs when Cas recounts Sam’s first loud conservation in his garden.

Dean has always thought that this inner conflict would come to a head in a bar somewhere. A finished case, a bit too much beer, he’d get hit on by some creepy asshole who thinks he’s “pretty” with his “princess lips” and “candy apple eyes” – because apparently even when he’s pushing forty, he’s still pretty enough to get hit on by creeps – and then drama would ensue when he says no. A homophobic slur here, an insinuation about being a girl there, finished with either a nice bar fight or storming off, then Sam’s following attempt at a conversation. According to Charlie years ago, it’s a popular trope in gay fanfiction and usually ends up in hot sex between the two guys, with a lesson about accepting yourself and blah blah whatever.

But no, Dean’s apparently too good for fanfiction tropes, because his moment of epiphany is still dramatic but much less macho manly bar fight. He’s out shopping with Jack one afternoon, since they’re in dire need of food supplies due to being down to a tablespoon of shitty instant coffee, a few slices of mouldy bread, a pack of nearly-expired bacon, and condiments that will probably only make that mouldy bread even worse. Thank god the hunters from the other world are gone now, out inhabiting the other Men of Letters chapter houses around the country so that they’ve got a web across the US. It might be horrible of Dean to feel this way but really, a home invasion was the last thing conducive to recovering from Michael’s possession.

So, anyway. He and Jack have filled the cart with food and are now preparing to brave the clothing department of Walmart, only because Dean had decided that it might be nice for Jack to have more than a few shirts and pairs of jeans for himself. He makes a beeline for the men’s jeans and picks out the first pair he finds in Jack’s size.

“Simple but decent when it comes to hunting,” Dean says, turning to show Jack. “About as tough as you can get for this price – the fuck did you go, kid?”

Jack’s nowhere to be found. Heart starting to race, Dean dumps the jeans and heads off in search of the human naphil, because Cas is going to have his ass for days if he loses their kid. He’s still not adjusted to being with Cas, especially with a kid between them (and between Sam too, but he’s firmly not involved in this Dean and Cas equation), but apparently letting a homicidal archangel possess you while the love of your life pleads for you to not make such a dumbass move is catalyst enough to really get things rolling.

In any case, he knows for sure that he’s going to be in the shithouse if he loses Jack, so he navigates the clothing department with all the grace of a giant tortoise whose shell is made of fraud-funded food. Jack’s nowhere in the men’s department, so Dean checks the kid’s department in case he’s started having a ‘one-year-old in the body of a twenty-year-old’ crisis, but he’s not there either.

“Dean!”

Dean whirls at the sound of Jack’s voice calling his name. He locates Jack in the women’s department, standing next to a rack of discount skirts, and he struggles on over.

“They’re so pretty!” Jack says in awe, running his hand over a white, flowy skirt that looks to be about mid-thigh length.

“Don’t run off on me like that!” Dean snaps, mostly to avoid having to crush the light in Jack’s eyes as he pulls out a long red split skirt to examine it. “Cas would fuckin’ kill me if I lost you. You know how much of a passive aggressive dick he can be.”

The lady at the rack nearby tuts, which Dean assumes is at his foul language. He shoots her a winning smile, but she just tuts again and looks away, so he shrugs and turns back to Jack.

“I’m sorry, Dean,” Jack says, his mouth drooping as he puts the red skirt back. “I didn’t mean to make you worry. I just went looking for stuff I’d like, and I found this section and – Dean, look at how pretty these skirts are!”

“They’re for chicks, Jack,” Dean says, painfully aware that Cas is probably going to kill him for instilling human gender roles in their son who’s pretty much a toddler with adult intelligence.

“But why?” Jack says and runs his hand over the white skirt again. “Why do humans insist on assigning gender to pieces of cloth?”

“Okay, for one, you’re human to everyone else, so you might wanna tone down on that alien talk,” Dean mutters. He shoots a look at the lady out of the corner of his eye, who’s so thoroughly invested in the table of T-shirts that it’s obvious she’s eavesdropping. “It…just is, okay? Guys wore skirts ages ago, now they don’t. Shit changes.”

This coming from the guy who likes to wear pink panties makes it incredibly hypocritical. He knows that. But there’s a difference between a sexy kink and just outright wearing women’s clothing every day, and Jack doesn’t seem to be getting it. Dean’s just going to conveniently ignore how the fact that he likes wearing panties is waving its hands to get his attention, like there’s a ground-breaking revelation to be had if he examines it further.

“I don’t understand,” Jack says. “If it’s comfortable then why not wear it?”

“Because you’re not a chick. You’re a guy.”

Jack just frowns as though these are foreign words. “But how do I know that I’m a guy?” he says. “I met someone when I was off training my powers who told me that when he was born, everyone assumed he was a girl because of his body, but he wasn’t a girl. How do I know that that’s not me?” 

“Do you feel like you’re a girl?” Dean’s too sober right now. And he’s totally not equipped to handle a conversation like this. Cas is better suited, what with his utter disregard for human gender roles.

“I don’t know!” Jack clutches the skirt, no doubt to stave off the distress spreading across his face. “I like things that people call “womanly”. I like cooking with you and caring for other people just like you do. I like feeling pretty sometimes. I don’t like people thinking that I have to be tough and “manly” and not interact with my emotions just because I was born with a certain set of genitals.”

The woman nearby outright winces, so Dean turns to her with a fake smile plastered on his face.

“Is there a problem, ma’am?” he says. She dithers, like she’s torn between speaking her mind and admitting that she was eavesdropping on another person’s conversation.

“No,” she finally says.

“Good.” Dean turns back to Jack. “Look, kid, I can’t help you there.”

“But you like things that society designates as “womanly”,” Jack says. “Yet you’re comfortable in your masculinity.”

Dean sighs and draws Jack away from the nosy woman. Jack brings the white skirt with him, and Dean’s seriously thinking that he’s going to have to buy the damn thing just to shut Jack up.

“I just don’t understand,” Jack insists.

“Look, kid, I don’t either,” Dean says. “And any time I tried anything, my dad kicked my ass for it. I…don’t want that to happen to you.”

“I appreciate your concern, Dean,” Jack says with that soft little smile of his. “But you and Sam have taught me how to take care of myself. I might only be human now, but I’m sure I can handle negative opinions if I’m not hurting anyone. And I know that you wouldn’t “kick my ass for it”.”

For a moment, Dean sees himself in Jack; his younger self, so fresh and idealistic, unaware of just how horrible a place the world was. He’s got one vague memory from before Mary’s death of her painting his nails for him because he’d seen the bottle of blue polish and wanted to “look pretty like Mommy”, only to result in one of the worst fights between John and Mary about “turning their son gay” while Dean huddled in bed crying.

In that moment, he vows that Jack will never know that pain. He’s never going to be that parent that forces a tonne of bullshit on his kid because everyone else thinks he should. He’s already raising the one-year-old grown-up son of Satan in a hunter life with his angel boyfriend, so there’s literally nothing about this that’s normal in any way. No way is he going to squash that light in Jack’s eyes that John had squashed out of his.

“Fine, whatever,” Dean says. “Get the skirt if you want.”

Jack’s face lights up, and he throws his arms around Dean while thanking him over and over again. Dean pats him on the back, praying that the kid doesn’t suffocate him to death, and thankfully he’s given back control of his lungs after just a few more moments.

“Tsk.” It’s so quiet and barely there, but Dean’s trained ears pick up the reproach from the woman who totally hadn’t started inspecting the next table over just to stay within hearing range.

“You know, it’s rude to listen in on conversations you’re not part of,” Dean says with the most passive aggressive smile he can muster.

“And it’s wrong how you’re raising that son of yours,” the woman retorts. “Especially with your…boyfriend.”

Ah, so she’s one of those ones. Dean’s fake smile just widens. “Well, I don’t see it as any of your business, sweetheart.”

“You’re sending your child to Hell by encouraging him to live in sin!” the woman says. “How can you say it’s not any of my business when I’m concerned for the poor thing?”

“Dean and Cas have always taught me that I’ll never go to Hell if I’m a good person,” Jack says straight to the woman’s face. Ah, Dean’s so proud. “And I don’t see how wanting to wear a skirt makes me a bad person.”

“You gay and transgender people are wrong in the eyes of the Lord,” the woman says. Jack frowns.

“God doesn’t care about that.”

“Just back up,” Dean says. “You can’t argue with crazies like her.”

“She’s insulting you and Cas,” Jack says. “And me. I can’t just let her hate other people when she’s wrong!”

“You’ll never be able to prove it to her,” Dean says. “Trust me, kid, you could have God himself pop in and tell her she’s wrong and she’ll still insist that she’s right and he’s just “pandering” or whatever. They don’t actually give a shit about God. They just use that bullshit so they can act like they got a real reason to hate others rather than having to admit that they’re just assholes.”

“You people sicken me,” the woman spits.

“At least we’re here minding our own business and not going around scaring people into believing our fairy tale,” Dean says. He marches over to the skirt rack and, looking the woman straight in the eye, grabs the red skirt that Jack had also been eyeing. “And you know what? My son can have all the skirts he wants. Hell, I’ll even paint his nails for him. ‘Cause I wasn’t allowed to be pretty as a kid, so Jack’s gonna be the prettiest fuckin’ guy around. You capiche?”

The woman looks like Dean had whipped his dick out and started pissing right in front of her, but Jack looks like Dean had personally hung the stars just for him. Dean drapes the skirt in the cart and nudges Jack.

“C’mon, kid. You still need some good, strong clothes for hu – uh, work.” He wheels their cart back to the men’s section, leaving the woman stewing and Jack bounding along beside him, and he feels in his bones that he’s made the right decision as a parent.

***

For the next few weeks, Dean can’t shake off Jack’s words from their shopping trip. Every time he cooks, he finds himself examining his actions under a microscope, dissecting how much he enjoys cooking for his family and exactly how he feels about it. He does the same thing when tidying the bunker, even going so far as to dust the top of the bookshelves and use some new, tropical-scented shit in their laundry that quickly earns Sam’s seal of approval. And fussing over Sam after the guy had been stabbed by a rabid vampire on their hunt has him spaced out for the rest of the night as he reflects on just how much he mother-hens his brother.

It doesn’t take long for Cas to notice. But then, Cas always notices. However, he doesn’t bring it up until about a month after the Shopping Trip, as the incident has now been dubbed.

“What’s wrong, Dean?” Cas’ voice is thick with the sleep he doesn’t need but enjoys when he can cuddle with Dean all night. “You’ve been quiet for weeks now.”

Dean doesn’t say anything at first, instead running his fingers down Cas’ bare chest and stomach and feeling the muscles spasm under his touch. He can’t help but marvel that, for all his holy angelness, Cas is still so incredibly human in many ways, the biggest way being how he chose to willingly tie himself to a human in the way he’s with Dean.

“Is it about Jack’s skirts?” Cas says into the silence. “You’ve been quiet since then. But I think you were fantastic to buy him those skirts. I can’t remember the last time I’ve seen him so happy than when he came to show me how they look on him. The red skirt especially suits him.”

“How do I know that I’m a dude if I like chick things?” The question comes out so softly that human ears would have missed it. But Cas doesn’t have human ears.

“Is it really that important that you know?” Cas says. He sighs and shakes his head. “My apologies. That was insensitive of me to say. I just don’t understand humans and their insistence on assigning themselves boxes and roles based on physical characteristics.”

“Look, I know you can like some chick things and still be a dude,” Dean says. “Just like I know chicks who are into cars and other “guy shit” and they’re still girls. But…I dunno. It feels like I’m missing something when I say that.”

“How so?” Cas says.

“Just…somethin’ Jack said about how you know you’re one or the other.”

“It’s not necessarily that simple, Dean. There’s so much more than just one or the other.”

Okay, that makes Dean blink. He’s had some vague knowledge that this exists – how could he not, when assholes everywhere are raising up a stink about “snowflakes” or whatever -  but to actually have an angel of the Lord tell him that there’s more than just guy and girl makes his head spin.

“This may not be of any help, since I’m an angel,” Cas says, “but I’m not a man. You see me as such, since my body appears that way, and I’m utterly indifferent to what people call me so my pronouns don’t bother me. I’m not a woman either. I don’t even know if I am anything.”

“That’s literally no help at all,” Dean says. “Thanks, you just confused me more.”

“Eat me,” Cas mutters. Dean snorts at that, because he can always count on Cas to unintentionally lighten the mood. “Talk to me, Dean. Walk me through your thoughts. I don’t know exactly what to say right now.”

“My thoughts are a fuckin’ mess,” Dean says. “Mostly ‘cause this is shit I’ve been shutting down since I was a kid ‘cause you know Dad would kick my ass if I tried. I remember when I was four and my mom painted my nails ‘cause I wanted to be pretty and Dad pitched a huge fit.”

“You were a child,” Cas says. “Children have no concept of gender roles until they’re taught, whether directly or through emulation.”

“I like a lot of “chick” stuff,” Dean says, tightening his hold on Cas like the angel can protect him from his inner crisis. “I like cooking. And I get that a lotta famous chefs are guys but…this is different. It feels more...domestic. I like keeping the bunker tidy ‘cause…it’s home, y’know? I’ve never…had a home before Baby. I just…like things to be nice. I like looking after others. I like listening to Taylor Swift and I’m kinda getting into Ariana Grande.”

The words are spilling out of him like an avalanche as he bares his soul for the first time ever to possibly the only person who would never judge him. As much as he loves Sam, his little brother’s also grown up under the reign of John Winchester, and Sam might be a softer and more emotional guy but he’s still got a lot of shit of his own.

“Sometimes I get sick of bein’ tough and strong and manly,” Dean babbles, burying his face in the crook of Cas’ neck as the deep stuff starts to uncontrollably emerge from years of lock and key. His eyes begin to sting and his lungs are working overtime at this point, but the fingers that start to card through his hair provide a point of sensation that successfully helps keep it under control. “Sometimes I…I wanna be pretty. Like Jack does. I don’t wanna wear a skirt or anything but…I wanna be that four-year-old kid who wanted to wear nail polish like his mom and dress up with her and try to wear her heels but trip and fall flat on his face while she laughs. I wanna be that guy who knows how to braid his younger brother’s hair ‘cause he won’t get a fuckin’ haircut. I wanna wear those flower crowns that Jack makes without feeling like I’m a sissy or somethin’.”

Cas hums, still stroking Dean’s hair. “You can still be a man and enjoy those things.”

“That’s the thing,” Dean says rather bitterly. “That doesn’t feel totally right either. Like…I don’t feel like bein’ a guy fits if I do that stuff. Like if I let myself enjoy that stuff then…not that I don’t deserve to be a guy, but more like…” He fumbles for the right words, wishing he could just let out a long groan and have Cas understand from that, because that’s really the best way he can describe himself. “More like calling myself a guy doesn’t fully describe myself ‘cause…I’m kinda not. But I ain’t a chick either and it feels wrong calling myself that too. If that makes sense?”

“It does,” Cas says and kisses the top of Dean’s head. “I think an appropriate allegory in this case would be nationality. You humans have assigned a label to each other based on where you were born, and you act in different ways according to this label that you were forcibly given. And I’ve noticed how if someone moves to another country, they often face derision for not having been born there like everyone else, especially if they don’t look like the majority or their culture drastically differs from the place to which they move.”

That makes sense. How many times has Dean heard jokes about American stereotypes? Or shitty comments about people based purely on ideas that other people have about where they were born and lived?

“Nationality isn’t anything tangible. It’s more of a feeling and a mutual culture based on shared experiences. And there aren’t just two nationalities or two experiences. There are so many more; some are similar to each other and some are totally different.”

“Nice soapbox,” Dean quips to hide how his head is spinning at this wealth of information. Does that mean that he can just…be neither? That he can let himself be pretty when he wants to while also being the cool tough guy he usually is, and…he can still be Dean? He doesn’t have to be a guy or a girl?

“It’s a very individual experience,” Cas says. “Mine is completely different to yours or Jack’s. That’s why it’s difficult for me to really find the right words for you.”

“Blame Jack,” Dean says. “He’s too pure for his own good. He’s corrupted me.”

“Dean,” Cas chastises. “Don’t talk about our son like that or I won’t sleep with you for a week.”

“You won’t last a week without my dick but sure,” Dean retorts. “So, like…do I have to call myself something since I’m not either? Tell the whole world? Start wearing spandex and dye my hair blue or something?” He looks up just in time to catch the biggest eyeroll Cas has ever given him, so he snickers and nips at Cas’ throat. He refrains from marking Cas up, knowing that if he does then Cas’ animalistic side will come out and he’ll get dicked six ways to Sunday. And while he normally wouldn’t ever turn down some good, hot sex with Cas, he’s also in the middle of an important conversation for which he wants a resolution.

Okay, wow, he’s been talking to Sam too much if he’s choosing a conversation about his feelings over hot angel sex. But it’s worth it, considering that he can feel the chains of another layer of John Winchester’s Perfect Son loosening from around him.

“You don’t “have” to do anything,” Cas says. “You’re still the same Dean Winchester I fell in love with.”

“Hey, whoa, whoa, don’t you dare bring that word up,” Dean protests, but he feels about ten times lighter with Cas’ affirmation that he doesn’t have to do anything different and can just keep doing his own thing while knowing this new thing about himself.

“Oh, shut up, Dean.” Cas immediately contradicts his annoyed tone by kissing Dean’s head again, so Dean decides to lean up and catch Cas’ lips in a proper kiss. Cas hums and cups Dean’s face and their kiss is slow and deep, with small nips and tongues swiping across mouths without dipping inside.

“No but seriously, is there a word for it?” Dean says breathlessly when they separate. “That bitch at Walmart said “transgender” but I don’t feel like that’s me. Others like me might but…not me. I’m still cool with this totally hot body and with people thinking I’m a guy just to make shit easier on everyone, ‘cause I at least know I’m…not.” It feels weird as fuck to say that out loud but also oh so freeing.

“Some might call you egotistical,” Cas mumbles. “It would be totally valid of you to call yourself that if you want, but I understand why you feel it doesn’t apply to you. I’ve heard the term non-binary before, when I was at a homeless shelter as a human and I met someone who referred to themselves as such. After I confronted a bigot and said that I’m utterly indifferent to my own gender, the other person confided in me and non-binary was the term they used. You could try that and research further from there.”

“But…I don’t have to if I don’t want to?” Dean says. Don’t get him wrong, having an actual word that encapsulates him is just…wow. Holy shit. He’s real, he’s allowed to exist, and there are others who are not only like him but also open enough about their identities that other people can find this information and realise shit about themselves too. But he’s literally only just started coming to terms with shit he’s locked deep for the past few decades, so he’s not yet sure if he’s ready to start labelling himself and being so open about it until he’s had more time to work through it.

“Of course not,” Cas says. “You don’t have to do anything you don’t want to do. Just because Jack feels comfortable enough to wear skirts doesn’t mean that you ever have to as well. I told you, it’s highly individual.”

“Jack’s non-binary too?” Dean says. “I mean, I ain’t surprised, but…”

“We had a conversation. He told me that you said he should come to me, since you weren’t equipped to talk about it. He also said that he didn’t mind if I told you and Sam, so I won’t ever tell anyone else about you unless you allow me to do so. That would be rude and horrible and downright violent if the wrong person learned that when you didn’t want them to.”

Okay, that’s another weight off Dean’s shoulders. “Like tellin’ others that I’m bi, right? It’s for me to tell.”

“Precisely. And I’m very proud that you felt comfortable enough to tell Sam, Jack, and Mary.”

“I had a crisis back in Purgatory when I was lookin' for you.” Dean kisses Cas’ shoulder and snuggles under his chin. “Then I had years after that to deal with it and work through Dad’s shit. But this is just…new. I think I need a bit more time.”

“You have all the time in the world, Dean.”

They lapse into a comfortable silence, and Dean starts to doze off at the feel of Cas stroking his hair despite having only woken up half an hour ago. But then something occurs to him, and it sets a cold pit of anxiety off in his stomach at the thought of voicing it out loud but…he also kind of wants to say it, if he’s still digging shit up from deep. And Cas won’t judge. This is the same guy who approves of their son wearing skirts.

“Cas?” Dean says. Cas hums in acknowledgement. “I…I just…shit, this is embarrassing.”

“If you don’t want to tell me, you don’t have to,” Cas says.

“No, I do wanna tell you. I just…bear with me, okay?” Dean pushes himself up into a sitting position so that he can look Cas right in the eye, and what he sees there helps loosen his shoulders ever so slightly. He takes a deep breath and blurts out, “Ilikewearingpanties.”

“Pardon?” Cas’ forehead creases.

“I. Like. Wearing Panties. This one chick, Rhonda Hurley…she made me wear them once. And I liked it. But that’s not even…look, it wouldn’t be so bad if it was just a kink, ‘cause loads of dudes – normal dudes – they like wearing women’s underwear too. But only during sex, ‘cause that can be hot.”

“You’re not abnormal for not being a “normal man”,” Cas says. “I know there’s a term to refer to people who aren’t transgender, but I can’t quite recall it.”

“That’s not the point,” Dean says. “I just…nail polish and feeling pretty are one thing, okay? But actually liking pretty, lacy underwear outside of sex, where nearly anything goes…Jesus, Cas, if anything was gonna make me suspect I’m not fully a guy, that’s it. I even…” His voice drops to a whisper as he confesses something to Cas for which John would have probably broken his ribs. “I even like the thought of wearing a bra. Not ‘cause I need it, but ‘cause I wanna see if it’d make me look nice. And not “goddamn Dean you look so sexy and I wanna fuck you in those girly clothes” nice like other guys would think but…y’know, “Dean you look so soft and happy” nice.” His shoulders slump, and he looks down at his fidgeting fingers. “I just wanna be not-tough for once. I just wanna be pretty without feeling ashamed or like I’m a girl when I’m not. Or that I have to be more like a guy when I'm not exactly that either.”

“I’m not sure I see how women’s lingerie is much more of a deal breaker than other feminine things,” Cas says. “And although I understand why you do so, I wish you wouldn’t attach such shame to it.”

“Yeah, why do you think I felt okay telling you?” Dean mutters. Cas’ eyes crinkle and, with a small smile, he sits up so that he can lean in and kiss Dean softly.

“I’m honoured that you trust me enough to confide in me, even if I don’t understand your social taboos.”

“Again, why d’you think I told you? Sam wouldn’t make fun of me but…he’s also human. He also grew up in this shithole society. He wouldn’t get it like you do.”

Cas’ eyes soften even more, and he gives Dean another kiss. “Maybe you could wear some of this clothing in a non-sexual situation with just the two of us,” he says. “No one else. Or if you would feel more comfortable without me, you could do it yourself.”

“Trust me, dude, I’d be a tonne comfier with you there so I don’t end up spiralling and shit,” Dean says with a dark little laugh. “Just ‘cause I realised all this shit now doesn’t mean I’m cool with it or anything.”

“Like I said, you have plenty of time. Use however much of it you need to become more comfortable with yourself. And you’ll always have my support, Dean. And Sam, Jack, and Mary’s, when you feel that you can tell them.”

A wide smile of relief splits Dean’s face and he pushes Cas to lie back down, then drapes himself on top of the angel. “You’re the best, man. You’re a literal angel.”

“I know. I have the halo to prove it,” Cas deadpans. The fact that Cas has finally grasped things like sarcasm after years of fraternising with humans is possibly the funniest thing Dean’s encountered all day, and it takes a humongous effort to just snicker rather than descend into a fit of laughter.

“I’ve changed my mind,” he says, pushing Cas’ chin back to start kissing down his throat. “You’re the biggest asshole around.”

“You –” Cas cuts himself off with a hiss when Dean nips at the skin over his pulse point, sucking to ensure that he leaves a dark bruise behind. “Dean, you know this – that this erodes my self-control –”

Dean gives him a shit-eating grin. “Good.” He bites again, only to blink as the world around him shifts and blurs when Cas grabs him by the hips and bodily throws him back on the bed, then straddles his hips, blue eyes blown black.

“If one thing about you never changes, it’s how infuriating you are,” Cas growls.

“Yeah, but you like me anyway,” Dean says, grin widening. Cas rolls his eyes.

“Sometimes, I wonder why.”

“Hey.” Dean runs his fingers down Cas’s stomach and dips a finger below the waistband of his white boxers. “Less talking, more kissing.”

***

“Dean, you look like you’re gonna puke,” Sam says when Dean corners him after breakfast the next day. “What’s wrong?”

Dean swallows, takes a deep breath, then decides to just go for it. He doesn’t want to have to spend ages hiding something like this from his brother when he can have another person supporting him, especially after everything he and Sam have been through. “I’m not a guy, okay?”

“Uh…what?” Sam frowns. “You’re…uh, wow, that is big. Are you –”

“I’m not a girl either,” Dean rushes to say. “I’m…neither. And kinda both. But mostly just neither. Cas calls it non-binary but I dunno what to call myself yet. If I even wanna call myself anything at all.”

“Huh,” Sam says. “You know, I always knew you were bi, but I never even suspected you weren’t cis.”

“Cis?”

“Not trans.”

“Oh, is that what it’s called? Cas couldn’t remember.” Dean blinks and points at Sam. “Wait, you know about this shit?”

“Of course I do,” Sam says. “The internet exists. And I thought I might not be a cis guy at one point, so I went researching, but I’m pretty sure I am. I did learn a lot, though. I know I don’t really care about gender when I’m into someone, but I have to be close to them to like them like that. That's why I'm so close to everyone I sleep with or get together with. I just never told you because you had your own stuff to deal with.”

“Fuckin’ nerd,” Dean mutters. Sam doesn’t even bitchface him this time, so Dean’s expecting some speech about how happy he is that Dean trusts him enough to confide him and whatever.

“Does that mean you’ll finally braid my hair for me?” Sam says with a smile so innocent that it’s dripping with guilt. Dean rolls his eyes and flips his brother off, then promptly regrets it when the moose turns all touchy-feely and pulls him into a hug.

“Fuck off, bitch,” Dean says into Sam’s plaid shirt.