#OH MY GOD HOW AM I STILL THIS INSANE ABOUT DESTIEL 2 YEARS LATER

[gaytedlasso]

If you are the sun, then I wanna be the moon

I wanna reflect the light that shines from you.

~

Happy November 5th !

original poem

[the-stories-in-my-head-95]

Butterfly Wings and Guitar Strings- Part Three

Bucky Barnes x Plus Sized!Reader

Summary- The Avengers are the biggest rock band in the world, but you’ve never been a fan. That is until your best friend Helen Cho wins back stage passes to their concert in Vegas. While she’s making heart eyes at the drummer Thor, you’re falling for their lead guitarist Bucky Barnes.

Message- If you want to be tagged send an ASK! Also not my pictures.

Warning- Reader was abandoned as a baby and grew up in foster care, because she was sickly as a baby.

Part One  Part Two

Word Count- 1059

“So where did you disappear to last night?” Helen asks, as she packs her suitcase.

“I got married.” You say.

“What?” Helen gasps.

“I got married.” You say.

“To who?!”

“Bucky Barnes.” You say, smirking.

“Like the Bucky Barnes that’s in The Avengers?” Helen asks.

“I actually think Bucky is a stage name.” You say. “Cause according to our marriage certificate is first name is James.”

“Bucky’s his nickname.” Helen says, crossing her arms. “Where you two at least drunk?”

“Nope.” You say. “We were both stone cold sober.”

“I don’t know if I believe you.” Helen murmurs, glaring at you.

“Give me one minute.” You say, grabbing your phone. You scroll down to Hubby and hit facetime. It rings about 5 times before Bucky picks up.

“Hey, Wifey.” He says, his voice thick with sleep. “What are you doing up so early?”

“Our flight leaves in like 2 hours.” You say, smiling. “Also its 10:00 in the morning, it’s not early.”

“Life of a rock star, Babe.” Bucky chuckles. “Party all night, sleep all day.”

“Holy shit.” Helen murmurs. “You married Bucky Barnes.”

“Say hello to Helen, Darling.” You say, moving your phone so your friend was in view.

“Hello, Helen.” Bucky says. “It’s nice to see you again.”

“Bucky Barnes knows my name.” Helen squeaks. “And he’s married to my best friend.”

“Told you.” You laugh, putting your arm over Helens shoulders.

“Holy shit.” Helen murmurs. “This is insane.”

“Clearly Helen needs some time to process this.” You chuckle. “I’ll call you when I get home, alright?”

“Alright.” Bucky says, smiling. “Bye, Doll! Bye, Helen!”

“Bye, Bucky.” You say, before hanging up.

“You’re married to Bucky Barnes.” Helen murmurs.

“I feel like that’s been established already.” You laugh.

“How is this even going to work?” Helen asks. “You have school!”

“For like another month.” You say, shrugging. “Once I’m done I’ll move to LA.”

“Where you’ll live happily ever after with Bucky freaking Barnes.”

“Exactly.” You say.

**1 week later**

“Are you happy to be home?” You ask, watching as Bucky unpacks his suitcase over skype.

“Yeah.” Bucky sighs. “I love touring, but being home is nice.”

“Show me around the apartment! I wanna see where I’m gonna live!”

“This isn’t where you’re gonna live.” Bucky says.

“What do you mean?” You ask. “I thought I was going to move in with you.”

“You are! But this isn’t where we’re gonna live. I bought us a house!”

“You didn’t have to do that.” You murmur.

“I know!” Bucky says, smiling. “I wanted to.”

“God you’re perfect.” You sigh.

“So are you, Doll.” Bucky says. “How’s school?”

“It’s good, I just submitted my thesis. I should hear back from the committee in about three weeks.”

“Have you gotten your plane ticket yet?” Bucky asks.

“Yep.” You say, nodding. “Can you text me the address of our house? I need to know where to mail all my stuff.”

“Of course.” Bucky says, smiling. “I like hearing you say that.”

“What?”

“Our house.” Bucky murmurs.

“God, you so cheesy! I kinda love it!”

“Glad to hear it.” Bucky chuckles. “Oh, I forgot to tell you, I added you to the list at Shield Records.”

“The list?” You ask.

“It means you’ll have access to the building, and me if I’m recording.” Bucky explains. “This way you can get ahold of me if something happens between now and when you get here.”

“Look at you, thinking of everything.” You say grinning. “Now tell me about your friends, you haven’t said much about them.”

“Alright.” Bucky says. “Stevie- he plays base- and I have known each other since we were kids. We played in a band called the Howling Commandos in college, but then the band broke up. He’s a punk, but also a total softy.”

“When did you guys join The Avengers?” You ask.

“We met Tony and Clint about a week after our old band broke up. Tony is the lead singer and Clint plays keyboard. Two weeks after that we met Thor and the rest is history.”

“Tell me about them, what are they like?”

“They’re-uh-they’re a lot. You’ll see what I mean when you meet them.” Bucky says.

“Okay.” You say, laughing. “Hey, I should probably go to bed, it’s almost 2 in the morning.”

“Alright, Doll. Call me tomorrow?”

“Of course.” You say, smiling. “Bye, Hubby.

“Bye, Wifey.” Bucky says, before ending the skype call.

**2 weeks later**

“Hey, Helen.” You say, sauntering into the lab. “How’s changing the world going?”

“I am not changing the world.” Helen murmurs, not looking up from her tablet.

“Sure, sure.” You say. “You’re just building a machine that will one day save millions of lives.”

“I need to get it to work first.” Helen grumbles. “Did you need something?”

“I’m done!” You say. “My thesis was approved a week early!”

“That’s amazing!” Helen says.

“I know!” You laugh, hugging your friend. “I’m done! I’m officially done with school!”

“Have you told Bucky yet?” Helen asks.

“No.” You say, shaking your head. “I kinda want to surprise him. Go to LA a week early, there’s a flight leaving tonight.”

“Will you be done packing by then?” Helen asks.

“Yeah, I just have to through my clothes into my suit case. But I still have a couple more boxes to ship-.”

“I can do that!” Helen says.

“Really?” You ask.

“Really.” Helen says, nodding. “But you have to promise me that you’ll invite me to come visit during the summer!”

“Of course!” You say. “I was gonna do that anyway.”

“You’re the best, best friend, Y/N!” Helen says.

“So are you!” You say, hugging Helen again.

“Now, go, pack! You have a flight to catch!”

“Thanks again!” You call over your shoulder, as you run out of the lab. But you stop at the door. “If I don’t see you before I leave I just wanted to tell you, that you’ve made these last 2 years amazing and that I’ll miss you.”

“I’ll miss you too.” Helen says. “Call me when you land in LA.”

“I will, promise.”

“Say Hi to your husband for me.” Helen says.

“I will.” You say, before finally leaving the lab. As you walk farther and farther away, the sadness you’re feeling starts to turn to excitement because this time tomorrow you’ll be in LA with Bucky.

@loneliestlittlerainbow​ @jenniegs​ @thedoctorscamanion​ @loveisfriendship ​ @mymourningtea​ @cassiopeia-barrow @marvels-ghost  @fandoms-fandoms-everywhere99​  ​ @loverbug1123 @pleasantdreamqueen​ @pbandj14​ @itsintothegreatbeyondstuff @princessleah129​ ​ @courtneychicken​ @battlebunnyteardropsinthesun​ @that-one-book-girl​ ​ @yipthegoddess​ @brooke-supernatural16​ @ailynalonso15​ @thefangirlliveson​ @conspiracy-teen​  @thegoddessofvampire​ @the-butterfly21​ @theshortegg​ @witchseer25607​ @bee-wrecker​ @precious-cinnamon-roll666​ @destiel-artemis @jackles-jadalecki​ @thisismysecrethappyplace​ @marvelismylifffe​  @kanupps06 @okayputta @geeksareunique @mummy-woves-you @crazy-little-thing-called-buck  @writing-red​  @leticiakael​ @tabziecat​ @ravenclaw-fangirl-7 @huntermichelle​ ​ @learisa​ @cutie1365​ @msmaximoff​ ​ @kitkatgaming​ ​​ @writings-and-stuff​ ​@xxashy999xx​ @sebba-hiddles​ @slashheartlover​ @scarlettsoldier​ @ladysergeantbarnes​ @i-just-wanna-run-hell @tonystarkismyboy @bestillmystuckyheart @musedhufflepuff @dontevenblink-badwolf-tardis @iamwarrenspeace  @supernatural-strangerthings-1980​ @murydedeus03​ @confuzzled-panda​ @ravennightingaleandavatempus​ @ari-maximoff​ @useless-creature-213​ @wolfarrowepz​  @dumblani​ 

[pherryt]

Destiel 28. ‘Stop texting me weird stuff at night.’

This got long. i had this idea but to reach it required so much...i hope you like it.  the rest of it is under the cut

word count 2198

Deangroggily blinked his eyes open and rolled over with a groan. He peered blearilyat his clock and groaned again. His phone – the reason he was awake – chirpedand he sighed, groping at his bedside table for the cursed thing.

Hethumbed it open to find a text from Cas. As usual. Not a night passed that hisbest friend didn’t text Dean at least once – usually about the most inanethings.

Hehadn’t minded so much when they were younger, when his ability to fall backasleep at the drop of a hat was a well-honed godsend that he’d taken forgranted.

Well,not anymore. He would never take it for granted ever again should that skillreturn. He couldn’t remember the last time he’d had a good night’s sleep and itwas driving him insane, he was sure of it. As much as he loved Cas – somethinghe’d been hiding for at least the last 8 years – come one morning, Dean wasgoing to take a hammer to his phone and then it simply wouldn’t be a problemanymore.

Cas 1:23AM: Did you know that when the Trex animatronic for Jurassic Parkmalfunctioned, it looked like it was alive?

Cas 1:23AM: It did that a lot in the rain which, as you know, was highly crucial forthat iconic scene.

Dean: 1:25AM: Normally Id be all 4 random movie trivia but Cas I need sleep

Dean: 1:26AM: Tell me 2morrow

Cas: 1:26AM: Of course, Dean

Thenext night was the same at almost exactly the same time. And the night afterthat, and the night after that, just like it had been for years before.

“Deandid you know – “

“Iread the other day –“

“Isn’tit amazing how –“

Deancursed the invention of cell phones and his need to keep it nearby foremergencies. During the day, Cas’s texts were a welcome thing but at night hewas losing sleep because of them. After a particularly long day – hell, afucking long week, with his alarm set for way too fucking early in the morning– Dean readied himself for bed. He had a crucial meeting in the morning and hewas so damn exhausted.

Hewas asleep before his head hit the pillow.

Ofcourse, Dean didn’t get to stay asleep. His phone chirped once, twice, threetimes before he fumbled for it. Without even checking Cas’s messages, he simplytyped out.

Dean 2:06AM: Stop texting me weird stuff at night, man – I really need to fucking sleep

Dean 2:06AM: And I can’t do that if you won’t leave me alone

Hedropped the phone to the table and rolled over, firmly closing his eyes. Guiltwracked him and kept him awake, however. He hated being so short with Cas buthe needed to sleep. Cas would understand. Right?

Thephone was blessedly quiet, but it was too late.

Nomatter how long he lay there, Dean couldn’t fall asleep.

Hespent his entire day in a foul mood and a sleepy haze. His coffee maker was broken and when he stopped atDunkin’s he didn’t get two sips of it before he spilled it all over himself andthe Impala. The early morning meeting was nearly a disaster. Only quickthinking on Bobby’s part saved the deal. He dropped his tool box on his footand – well, the day didn’t get much better from there.

Thenext day didn’t pass any better. Despite the fact that Cas didn’t text oncethat night, or the next, Dean found he couldn’t sleep. Between 1 and 2 am,Dean woke with a start, convinced he’d forgotten something very important.

After3 more days of this, it dawned on him that he not only had not heardfrom Cas in the wee hours of the morning as Dean had requested (Demanded wasmore like), but not at any other point of the day either. And Dean missed hisbest friend terribly. It contributed to Dean’s increasingly foul mood and his ever-increasingsleepless nights.

Whyhadn’t Cas messaged him?

Thenagain, why hadn’t Dean?

Dean 3:38PM: Hey dude – movie & pizza nite 2nite? My treat

Dean 4:32PM: U in or what?

Dean 5:17PM: Hey buddy, u Ok? Havent heard from u in a while

Hetyped out the words “I miss you” and deleted them before hitting send at thelast minute, then opening a new text, to Cas’s brother.

Dean 5:20 PM: Hey, is Cas ok?

Ashe waited for a response, so many things ran through his head of what couldhave happened to Cas in the few brief days they hadn’t talked. Or that maybeCas was mad at him. What if Dean had ruined their friendship for good?

Thatthought had him hyperventilating and he had to shove it away.

Gabriel 5:21PM: Why don’t you pull your head of your ass and ask him yourself.

Gabriel 5:21PM: I’m not my brother’s keeper. That’s your job.

Gabriel 5:21PM: Now for the love of god, kiss and make up already. I need my sleep.

Deanstared at his phone. “Well, that was uncalled for,” he grumped aloud to theempty room. What had that been all about? Gabriel made itsound like he and Cas had broken up, but if Dean were dating anybody –especially Cas – he sure as hell would have known that. Had Cas really beenthat upset with Dean? Was it really that bad that Dean just wanted a singlenight worth of uninterrupted sleep? Seriously?

Themore he thought about it, the more it bothered him, till he stood up, grabbedhis jacket and his keys, shoved his feet into his boots and left. 20 minuteslater, he was standing in front of Cas’s door with 2 boxes of pizza and a sixpack. He shuffled till he could use his hand to knock and did so.

Therewas silence for a while and Dean knocked again, wondering if this had been agood idea. There wasn’t even any guarantee that Cas was home (He worked fromhome. He had to be home) and he hadn’t answered any of Dean’s texts.

Deanknocked for a third time and finally he heard movement. He breathed a sigh ofrelief that lasted only as long as it took for Cas to open the door.

“Fuck!You look like shit!” he blurted.

“Thankyou. So do you.” Cas’s voice was flat as he opened the door further. He didn’tmove out of the way. “What are you doing here?”

“Look,wanted to apologize for the other night and hey, man, I missed ya! So what doyou say? Pizza? Beers? Netflix?” Dean waggled his eyebrows at Cas and the smallhint of a smile appeared as the man let him in.

Deantoed off his boots and didn’t even bother bringing anything in to the kitchen.He headed straight for the couch and placed the boxes and the beers on the beat-upcoffee table. Netflix was already on, and it looked like Cas had been binge-watching…Deansquinted at the tv…Reality TV? Oh boy, things were worse than he thought.

Hesat on the couch beside Cas who was already curled up in a blanket and a sliceof pizza – sans plates – in his hand. The man looked exhausted, ragged. Deanknew he kept his own hours. Being able to work from home helped with that, butwhat the hell?

“Dude,haven’t you been sleeping?”

“Notreally. What about you?”

“God,I’d kill for a decent night’s sleep. I can’t remember the last time I had one.”

“So…mytexting at odd hours…when I stopped…?”

“Didn’tfucking help. Now I wake up waiting for them. Isn’t that weird? I wake up andstare at the ceiling and I can’t even get back to sleep afterwards. At leastwhen you texted me I could fall back asleep.” Dean admitted with a sigh, grabbing two of thebeers. He used the coffee table to pop the tops off and handed one over to Cas.“It didn’t help a damnbit, so, you can, y’know, if you want…”

“Dean, are you’re sayingyou missed me?” Cas said, his mouth full of pizza as his other hand acceptedthe beer.

“Dude,you must be more tired than I am. I said that when I walked in,” Dean took aswig of his own bottle, stillcold since he’d just picked it up. “Look, I know why I’m tired. What about you?And what was Gabriel talking about? That he needed sleep?”

“You texted my brother?” Cas blinked atDean in surprise. Dean blushed.

“You weren’t answerin’, Cas. I was uh…alittle concerned,” Dean said, not looking at Cas. He took a huge bite of hispizza.

Despite his attempts to not look, Deanstill caught Cas looking at him incredulously out of the corner of his eyes. “Haven’tyou ever wondered why I send you messages at all hours of the day?”

“Um…no? I mean, its what you’ve alwaysdone, so I just…it’s you,” Dean said,his words garbled because of the pizza. He turned to face Cas. “I just came toexpect it. Hell, most of the time, I was really looking forward to it. One ofyour crazy texts can turn a bad day right side up again. I just…I thought that’show it was.” Dean ended the statement slowly, swallowing the lump of cheese,dough and sauce in his throat. “Cas, is something wrong?”

If he’d felt guilty before, Dean feltextra guilty now. The way Cas had asked the question had made Dean reevaluate everythingin a flash. It was odd, now that he thought about it, to be texting or callingat any hour. Even though Dean knew Cas kept his own hours…when did he sleep?

Cas shook his head and smiled. “No,everything’s fine. Just been a rough few days, that’s all.” After that, thematter dropped and the two of them ate their pizza and watched Netflix.

Dean didn’t know what time it was whenhe jerked awake. The room was dark and there was something warm on top of him.He pulled the warmth closer, realizing as it shifted that it wasn’t his blanket,but Cas. They were both so fucking tired, they’d fallen asleep on the couch. Hestifled a laugh. He wasn’t sure what to do. He felt awkward basically cuddlinga man that didn’t know Dean had a crush on him. But on the other hand, he didn’twant to wake cas up. It was obvious that he needed his sleep as much as Deandid. As he debated the idea, Dean’s heavy eyelids drifted shut, his bodytabling the dilemma for now.

A jerking motion had him waking upagain, much later, according to the clock, about 1am. Dean’s grip on Cas tightenedand then he heard it – Cas was breathing hard, small whimpers pulling from histhroat.

“Cas?” Dean’s voice was still sleepy,but concerned. Rolling carefully, Dean tried to peer into his face. “Cas, areyou all right?” Dean reached a hand up to touch Cas’s face and his friends eyesflew open on a gasp. He jerked back and would have fallen off the narrow couchsave for Dean’s quick reflexes. He rolled to his back, bringing Cas with him,helping him settle face own on top of Dean. Cas groaned and let his head thunkon Dean’s chest.

After a moment, he tilted it to peer atDean apologetically. “I’m sorry, Dean. I didn’t mean to wake you. I know you’retired – “

“Dude…I saw the clock – do you wake upat this time every night like this?”

“Not…always…” Cas’s eyes slid away. “SometimesI’m already awake. Or…”

“Or?” Dean prodded.

“It uh…happens a lot. Sometimes a fewtimes a night.” Cas admitted slowly. Dean wondered if he would have, if he’dbeen rested.

“Shit, no wonder you look exhausted! Howlong - ?”

“Since I was a child. And no, going tothe doctor didn’t help. Taking sleeping pills doesn’t help either. It’s just…baddreams, old memories,” Cas said tiredly, sadly. Without even realizing it, Dean’shand started stroking Cas’s back and he watched those sleepy eyes start to droop.

“Does anything help?”

“Mhmm,” Cas said.

“What do you need?”

“Fss,” Cas said.

“What?” Dean blinked and strained hisears. That was certainly not English, he was sure of it.

“Jus’ you,” Cas mumbled a littleclearer. “’s always been you.”

Dean’s heart skipped a beat and hisnext breath was shaky. “Wait, is that why you always—”

“Mhmm,” Cas curled into Dean a littlecloser, completely unaware of how he’d taken the mans breath away by that one,simple sound. He continued to run a soothing hand along Cas’s spine and stareddown at the man quickly falling back asleep in his arms. “Don’ leave me…”

The last words came out slow and softand Dean almost missed them. His heart ached and he swallowed thickly. “Never,Cas. I promise.”

[awed-frog]

Hi! I realized something the other day (I'm really slow wth) My parents have the same age as Dean, lit (I know weird but wathever) and my mum is homophobic (I'm bi, sad story lol) and she watches the show with me. The thing is that I annoy her with Destiel and she gets really angry (at some point she started disliking Cas, imagine that) and she looks for back up in my aunt for example, peolple her age. But me? My friends know that I'm bi, one confessed she thought she was too 1/2

2/2 and one of my bf ships Destiel really hard too. And it made realize of just how difficult it must be for Dean to “came out of the closet” if he is bi (I’m sure he is but till it becomes canon…) I mean, it’s not easy for me, it’s not easy right now for a lot of people but I’m positive that it’s better than before. Dean and people his age had it worse I think and it opened my mind to how much he must have struggled, how possible it was that Jhon could have hit him for that, oh too long 2/3

3/3 Bc before realizing this? I was like “Jhon beating hip up for this? no way. Maybe if he caught Dean while drunk and half out of his mind, but sober and knowing exactly what he’s doing?” And i must sound really stupid sorry, bc now it happens this too but it’s just WOW poor Dean, I wanna hug him. Also Charlie is a champion, and those married hunter couple 😢 Why do people do this (Also, if you have more idea of how it used to be, could u tell me? Correct me if I’m wrong?) bye ❤

Hey there! Sorry you’re having some trouble with your mom, here’s to hoping she’ll grown more accepting with time!

(But even if she doesn’t, remember that has nothing to do with you - she can choose whether to be tolerant and kind, while you can’t choose whether to be bi or not, so the ball is in her camp.)

As for Dean - yeah, he’s more or less my age, but he moves in a background that’s vastly different from mine - I’m sure other people (maybe @bert-and-ernie-are-gay or @mittensmorgul or @thejabberwock?) could tell you what it was like to grow up in the States around that time, and how queer people were perceived. All I can tell you is that in my corner of the world, being gay was something people expected you to keep quiet about - in my school, only one kid was out, and five other had that kind of ‘we all know but they never said anything so we pretend we don’t know and maybe we’re wrong’ status, and I know life had its ups and downs for them. Some people were really antagonistic (it was mostly boy on boy banter that was the problem, and I know that the worst time for gay kids was P.E., because here everyone is expected to shower together, so a vague ‘Tom looks sorta gay, haha’ can quickly turn into a ‘Hey why is that f*ggot staring at me now I’m naked’ and then all bets are off), and most people didn’t really care one way or the other, but still - the trouble is, you grow up in a culture where you don’t really have positive representation of any kind - gay people were either men dressing up and wearing feathers in funny movies or hospital patients dying of AIDS in sad movies - even for someone like me, who grew up in a weird household and read all kind of books, it was difficult to imagine a gay person being - a normal person, you know what I mean? Someone who’d have a relationship one day, and a house and a whatever job and would fight over whose turn it was to wash the dishes. And for kids with conservative parents, things were often much harsher, as I wrote here. Plus, even in the 1990s, AIDS was a big concern for most of us, gay or straight, so that was a problem as well - the illness was no longer perceived as a ‘gay’ illness (which it never was, by the way), but the fact we were bombarded with messages about the importance of condoms and safe sex, even as kids, played a role in our general understanding of sexuality (our own and other people’s).

For me, personally, the consequence of this climate of silence and diffidence in how we approached the matter meant that I considered my crushes on girls to be ‘just a phase’, or something like ‘I want to be like her’ rather than ‘I want to be with her’; whether this prevented me from seeking out romantic connections with women, we’ll never know, but since I’m insanely happy with the relationship I have now and am deeply in love with the man who shares my life, it’s not really a problem for me. That said, yeah, it doesn’t really surprise me to see that the more openly we discuss the subject and the more we respect what we feel, the fewer people identify as straight - in the UK, 49% of young people are not straight, and to me that’s a figure that makes perfect sense. We generally fall in love with souls, not bodies, so the more open-minded we are about such things, the more our potential to form relationships with anyone broadens. And, of course, as we’re heading into an age where AI will be a thing, it’s likely our understanding of what a suitable partner is will change a lot over the next few decades.

As for Dean Winchester - as I said, I’m not an expert, but this is a guy who grew up in a very different - and often hostile - environment. Unfortunately, the US is still a country where members of the LGBT community face significant risks - risks teen!Dean would be very familiar with, since half his job as a hunter-in-training was going through the newspapers looking for cases. For instance, in 1993, when Dean was fourteen, there was the murder of Brandon Teena, and the year before, Allen Schindler was killed - since he was a soldier on duty, it’s likely John would have discussed that sooner or later, and the wider ‘Don’t ask, don’t tell’ issue. And, I don’t know - I don’t see John as homophobic, exactly, but still - he would have considered his kids’ legitimate wish to form a relationship with someone an annoyance at best (I wonder if Sam or Dean ever sulked when they had to move because they’d lose touch with a crush or a girlfriend, for instance - they must have, right?) and an irrational luxury at worst (a partner can distract you or get targeted by enemies, as John knew from experience), and as for Dean being bi - objectively, men are more dangerous than women, and there is a significant risk a predator will pretend to be gay to trap you and hurt you, so I’m thinking this is the reason John would have objected to Dean’s choices, if nothing else. Furthermore, we’ve seen how conservative the hunter community is (or used to be) - I think John would have agreed with the adults I met growing up - would have said that okay, whatever - if Dean wanted to have fun with a man, who could stop him, right, but he’d better be careful and he’d better be private about it and ‘Jesus, let’s hope the kid doesn’t like it up the ass’ because, whatever, people have been having trouble with this particular thing for the past three thousand years and that’s not likely to change any time soon. So, yeah - I think there’s a good chance Dean took a long time to even understand he was attracted to men as well, and there’s a possibility that his acceptance and understanding of himself was muddled by the fact he was abused at some point, and turned tricks later in life - personally, my headcanon is that his experimenting years happened during the Stanford era, when he was mostly alone, and since then he’s not really thought about the whole thing a whole lot - partly because he’s always with Sam (and Sam can be very judgemental), and mostly because Dean’s got zero time for any of that stuff, and a lifespan to match - we know he thinks he shouldn’t have any relationships at all, for a bunch of reasons, and that honestly breaks my heart. 

Poor guy. I really, really hope he’ll get his happy ending - God knows he deserves it.