As a teenager, Dean had some pretty cringe-worthy fantasies. Stuff based on smutty magazines, snippets of movies he knew he wasn’t supposed to see, and the good old power of imagination. Basically anything involving cheerleaders, too.
But the worst of it, the most absolutely embarrassing of it all?
It wasn’t the filthy stuff.
It wasn’t even the pervy stuff.
It was the little practiced bits of handwriting around the margins of his notebooks, drawn over or torn out or erased in the furtive, teenage anxiety to keep the full extent of his sexuality secret.
Castiel Winchester, Dean would idly write, back in those days before he had even heard the idea of gay marriage, let alone considered the personal possibility. It was the most ridiculous kind of daydream, impossible on so many levels, but Dean did love the way the letters looked together, looping in cursive. The t’s and e’s. The loop of Cas’ L and the loop in the Winchester H.
Castiel Novak-Winchester, sometimes. Cas Winchester.
The scribbles came out the most during study hall, Dean spending the time as a library aid. Christ, but Cas was an adorable little shit, his hair dark and floppy, his voice increasingly deep but stammering. Fuck, that boy could blush.
Dean’s favorite fantasy—and maybe his most selfish—revolved around the bullshit he’d had to do on occasion, kicking other kids out of the library on the basis of Causing A Disruption. He’d listed the incident descriptions as Excessive noise on the forms he had to leave for the actual librarian, but a more accurate account would point towards bullying. It’s such a fucking juvenile term for such obnoxious bullshit, but there they were.
Not that anyone actually knew if Cas was gay. He was just shy and kept mostly to himself, even more so since they became seniors and Cas’ best friend and never girlfriend Meg Masters had graduated. The rumormongers of Dean’s year had pointed to Meg, pointed to Cas, and come to the conclusion that if Cas hadn’t slept with a slut like Meg, there was no way Cas wasn’t gay.
Personally, Dean thought it might just mean Cas had actual taste in girls.
In any case, Dean’s fantasy was a simple one:
Some of the assholes in their year would be making barbed comments in Cas’ direction, hassling the guy across the tables while Cas was busy trying to bury himself into the science fiction section, and Dean would have reasonable cause to kick them out. He’d have some really good biting lines, too, optimal sarcasm and perfect timing. He’d chew them all out at the library door, maybe make a little speech but nothing too corny, maybe shove it in a few faces that Cas was actually a pretty cool guy if anyone had cared to notice…
And then Cas would be standing behind him, floored and touched.
Dean would close the doors, and then it would be just the two of them, Cas stammering his way through some sort of variation on “You didn’t need to do that” while looking at Dean with unmistakable gratitude.
From there, the fantasy varied a bit, but often led to a quick meander over to the copier in its little nook off in the back, Cas trailing along as Dean went about library business. And there, with the copier running and the printer’s noise covering his words, Dean would tell Cas that any of the bullshit people spouted about Cas kinda applied to Dean too.
Cas would typically say something like “R-really? But you’re so…” and gesture at Dean in a varying method of praise. There’d be just a little bit more of talk before Dean went in for the kill, backing Cas up against the side of the printer, standing close as Cas blushed and went quiet, staring up at Dean with too-blue eyes and parted pink lips.
In some fantasies, Cas had stubble. In others, he was as smooth-cheeked as he’d been at fourteen, at twelve, at the time they’d met.
In some, Cas wrapped his arms around Dean’s shoulders. In a few, he’d tentatively held to the parted sides of Dean’s plaid shirt.
In every fantasy, Cas had absolutely kissed back.
Naturally, Dean had graduated without ever so much as hitting on the guy. Too chickenshit, he guesses on the nights he looks back. It’s all worth a sigh, but not much more than a sigh.
He’s moved away, moved around. He’s come out. He’s done a lot of shit, some it better than the rest, but he’s always kept his taste for brunettes (and brunets). Sometimes, when he’s browsing through the scifi section of his local library, his mind wanders, and he thinks about Cas. It’s a thought that goes nowhere, especially not after their five year reunion: Cas hadn’t showed, not that Dean had expected him to.
Dean’s never gonna see Cas again. It’s a weird piece of reality to hit a guy in the head while he’s weighing whether he can speed read a brand new title in fourteen days.
Betting to himself that he can, Dean takes home just the one book on his way back from work, and promptly doesn’t read it that night. Instead, he turns in early after dinner, giving himself time to release some tension instead.
He gets his laptop and headphones. He puts out the lube and checks the level inside his tissue box. After a moment of further consideration, he puts down a towel and pulls out his top two dildos, just in case.
He likes keeping his options open, sue him.
Clicking around his favorite sites, he pings around by general categories instead of any specific search terms. He stares into that fridge of porn and still can’t figure out what he’s hungry for, not until a preview pic of an alleged “18yo shoolgrl slut” in a cheerleader uniform catches his eye.
Cheerleader, he types into the search bar. He opens a couple videos, closes most of them, only idly touching his dick now and again. He’s got all night to take his time.
And then he finds it. Naughty cheerleader getting horny in a library.
The cheerleader in question is probably around Dean’s age, more of a college cheerleader than the high schooler they’re clearly aiming for her to be. She leans up against a sparsely laden bookshelf while looking around furtively, a book of something censored out in her hand, presumably dirty. As she reads, she touches herself, making faces like the contents of the book are absolutely salacious.
Dean starts jerking it too, keeping slow, keeping loose. No rush.
The camera angle cuts back and forth between framing the cheerleader between the shelves, looking at her from the side, and going to close-ups looking at her directly. She plays with her tits, her cleavage spilling out of her uniform, and she leaves them hanging out as she reaches down, still one-handed, to pull up her skirt.
A new camera angle now: a behind-the-butt shot from the next shelf over, some guy in tight jeans and a tighter ass evidently spying the cheerleader.
Cut back to the cheerleader, going to town downstairs, theatrically fanning herself with the dirty book. She convulses against her own hand, choking down equally fake and pretty disappointing orgasm noises. She slides down to the floor, and as Dean sighs, ready to close the tab, there’s a loud unzipping sound.
In a sprawling sort of kneel, the cheerleader looks over her shoulder. The shelf that’s now at her head height barely has any books on it at all, but it certainly contains an erect dick. It’s a nice one, too, pretty sizable for a white dude.
The cheerleader definitely thinks so too, as she starts sucking on it with no further prompting, the bookshelf serving as a gloryhole. The man behind the dick groans, and fuck if that isn’t a nice noise.
Rather than closing the tab, Dean settles down. He’s here to stay, especially when the cheerleader pulls off with a giggle to playfully shush the guy and the guy responds by wagging his dick back and forth with a chuckle. She keeps moaning, keeps blowing him, and the guy’s vocal acting is way, way better than hers. It’s not that weird grunting guys sometimes do, and it’s not the empty reciting of dirty words and phrases Dean expected from the production quality.
No, these are breathy but confident sighs of fuck and suck me harder.
The deep voice does something to Dean. It hits him low and hot in a way that’s not fair. He clenches his ass against the towel, glances away from the screen to his dildos. One’s more of an additional bit of zest to jerking it, and the other is the full getting fucked in the ass experience. Dean licks his lips, considering his options.
“Oh, baby, you gotta fuck me,” the cheerleader moans. She pulls off completely, and the guy comes around the shelf at a prowl, a big letterman jacket hanging off his broad shoulders. Seen from behind, he goes right up to her, right into her, kissing her with a hard passion better suited to HBO than a daytime soap, hot damn. He grinds her back up against that bookshelf, his mouth pressed against her neck while she holds on tight, hands buried in his thick hair.
Down go his pants. Up goes her skirt. Neither of them are wearing underwear and Hallelujah for that. Still kissing at her neck, he hoists her up onto his dick. She squeals. Tugs on his dark hair. Tugs his head back.
Dean’s hand freezes on his dick, but the orgasm punches him low and dirty anyway.
What the fuck, his brain shouts. What the fuck.
He comes hard and unexpected, fighting his eyes back open as his dick takes over. The video plays on all the while, and Dean’s eyes keep seeing the same thing, the same face. Dean’s brain keeps shouting.
Sitting stunned and increasingly sticky, Dean watches Cas Novak rail a girl on streaming video. The whole rest of the video, Dean watches, and the guy never stops being Cas.
Holy, holy shit.
There’s a money shot, but it focuses on Cas’ dick, not his face. The girl’s face, definitely, but not Cas.
The video ends before Dean can gather his wits. He cleans his mess with quick tissue swipes, and then he immediately clicks back through the video until he gets a better view of the guy’s face. Because that can’t be Cas. Can’t possibly.
But it is. Even if the camera never shows Cas that up close and personal, even if it keeps way more to his co-star, the camera still doesn’t lie.
...And there’s another video featuring him off on the sidebar.
Dean quietly freaks out. Because, okay: Cas. But also, technically, a sex tape of a guy he knows. Knew. Is he meant to watch? Or… is knowing Cas reason enough that Dean shouldn’t? Because, like.
It’s porn, right? Produced and filmed and everything. So clearly, people are meant to watch. And Dean is people.
Dean clicks the next video. It’s a sequel. A milf of a librarian comes over to shut the pair of them up, and decides this is best done by riding Cas’ face, really pressing down against his tongue. Smothered and clearly loving it—pretending he loves it, acting like he loves it—Cas gives her what’s gotta be a ride worth taking.
The cheerleader girlfriend helps peel Cas out of his letterman jacket and blue polo shirt beneath, before they all fuck on the floor. The girlfriend gets Cas’ dick from behind, and she eats out the librarian while getting railed. Cas is glorious naked, his shoulders sporting a wide tattoo, the outline of feathered wings.
Dean doesn’t come again while watching, but fuck, he will soon.
The video ends, and very unhelpfully, only the actresses have been tagged in the video’s description. The name of the porn studio does show up at the beginning and end, though, so that’s a lead.
Dean spends just a bit too much time searching around the site for any other videos with Cas. On the basis of, uh. Seeing how he’s been. ‘Cause he’s looking good. Confident, toned. Really stupidly, drop-dead gorgeous.
That’s worth a bit of a search, right? Just a little one.
It takes some doing, but Dean finally finds a video with the name “Jimmy Angel” attached, and when he googles the name and turns off the safety filter, hell yeah, pay dirt.
Dean knows how he’s spending the next few evenings, that’s for sure.
He feels different about it in the morning. Shittier. Like maybe he’s invaded Cas’ privacy or something.
The day crawls by at work, Dean distracted by that circling thought. Fortunately, it’s Friday, so when a bunch of them meet up at the bar, Dean starts a hypothetical game of “Would You If.” They start off tame, like “Would you get front row tickets you knew would impress your date if the seats weren’t next to each other?”
The game nearly ends before Dean brings up the issue. “I got another one, I got one. Would you watch porn of someone just your type if you actually knew them in real life.”
“Yeah,” Benny says, no hesitation.
“What kind of porn?” Charlie asks. “No revenge porn or leaked nudes.”
“Like, professionally made porn,” Dean says.
Charlie mulls that one over while Jo asks, “Do I have to look him in the face the next day?”
“Up to you,” Dean says.
Jo bobs her head side to side. “If I only knew him in passing, maybe. And it would have to be actually good porn.”
“I’d buy their stuff,” Charlie decides.
“What?” Dean asks.
“If she was someone I knew and wanted to support, I’d buy her DVDs,” Charlie says. “The actors probably don’t get a cut, but letting the company know she’s in demand couldn’t hurt.”
“Huh,” Dean says.
“Would you date a porn star?” Benny asks, probably thinking he’s moving the game along.
“Would having sex feel like work for him?” Jo wonders aloud. “Y’know, like the stripper joke. Get home from work, take off their clothes and sigh, ‘cause it’s just more work.”
“Huh,” Dean says again.
“But the sex would be good,” Benny counters.
“Porn’s about looking good, not feeling good,” Charlie says. “Trust me. Do you have any idea how hard it is to find girl-on-girl videos that actually look like fun?”
“Not hard?” Benny and Dean respond in unison.
Charlie glares at them in turn.
“She’s right,” Jo points out. When everyone blinks at the supposed token straight person of the group, Jo clarifies, “About it looking good, not feeling good. Some of the positions they put the women in? No thank you.”
The conversation sticks around porn until their drinks run dry, and the topic changes with the next round. By the time Dean goes home, he’s feeling well enough to pull up his laptop for another night of indulgence.
Not knowing how much footage there’s available, Dean makes himself stop from skipping forward in the video. Jimmy Angel and nurse, it’s a good combo. An even better combo once “Jimmy” enters in tight scrubs and a white lab coat. The blonde nurse shows Cas the brunette patient, both women scantily clad for a doctor’s office.
The patient explains she’s been having trouble orgasming. Cas assures her that they’ll be able to help. Could she demonstrate what she usually does? The nurse hops up on the examination table too, leading by example. Both women masturbate, the nurse with more obvious pleasure. She manages to come, leaving the patient frustrated beside her.
“Sometimes, additional stimulus is required,” Cas reassures her, moving around to the back of the table. “If I may assist...”
“Ooh, so nice to have a doctor with warm hands,” the patient purrs as Cas slides her excuse of a top down and fondles her breasts, massive even in his large hands. As she leans back against him, Cas kisses her ear, her neck. He tells her how to touch herself. He tells the nurse how to touch the patient too. When he pinches her nipples tight and orders her to come, Dean completely believes she’s orgasming. Totally sold.
Sadly, the video doesn’t linger on Cas disrobing. He gets down to shirtless, sits on the examination table with his pants unzipped, and the nurse demonstrates how best to ride a cock. The patient gets her turn too, and once both women are slumped on the table in bliss, Cas jizzes on both of their chests while they moan and giggle. It’s a POV shot for that final bit, completely robbing Dean of seeing more than Cas’ dick and hand.
He watches it and rewatches it anyway, fucking himself with a dildo while the women ride Cas’ cock. After, when he settles down to sleep, he reminds himself that his feelings aren’t mixed. He’ll look into actual DVDs or whatever once he’s run out of online content.
And if he’s feeling a little bummed, well. He’d kind of been counting on Cas actually being gay. That’s a lot of teenage fantasies down the drain.
He’ll get over it. This is one hell of a consolation prize.
The next night, searching “Jimmy Angel doctor” brings up last night’s video, plus a surprising number involving spandex. The evil Doctor Hypnogasm, versus any number of knock-off, copyright-avoiding superheroines.
It should be hilarious, Cas in tight pants, shirtless under a lab coat, and wearing goggles on his head.
It should be ridiculous, Cas “hypnotizing” women by waving his dick back and forth until they sink to their knees and suck him uncontrollably.
It should be a lot of things, Cas authoritatively commanding his partner to obey and serve the forces of evil while he’s getting blown, but the thing it mostly is? Is hot .
Dean does his best to pace out the Doctor Hypnogasm videos, and he’s delighted to find that some of them stack. Doctor Hypnogasm amasses a harem, culminating in one giant fuckpile. Best of all, Cas finally gets all the way naked, showing off a couple tattoos up the sides of his thighs, a matching pair of flowering vines. There’s a Deathly Hallows symbol on one shoulder, a ring on the other. The angel wings on his back are more fleshed out, the line work far more detailed than in the library videos.
The night after Dean watches the harem fuckpile, he watches the library videos again. Yep, definitely only the outline of the wings in this one, and only the ring tattoo on one shoulder, no sign of Harry Potter. Paying attention this time, Dean pauses, and, oh, cool: Lord of the Rings.
He finds a couple more videos from the earlier batch, Cas in the letterman jacket as a tutor to an alleged teen. Another: Cas in detention, betting his fellow delinquent that he could fuck their milf of a teacher. Both boys eventually fuck her, but Cas makes first contact.
It’s not the best quality, that stuff. Clearly, Cas had gotten promoted into the Doctor Hypnogasm series. The after-school specials are definitely sub par, but Dean watches the detention video avidly, repeating the bits where he was absolutely certain it was about to turn into a true threesome, instead of two guys sharing a woman.
He switches around to all of his usual websites, making sure he’s catching all of the Jimmy Angel stuff. He keeps finding new little bits, or stuff cut from other videos he’s already seen.
The night after he returns his latest library book, nearly overdue and entirely unread, he has an epiphany.
Because there, at the top of the website, is the category bar.
Preference set to Straight.
Biting his lip, Dean clicks over to Gay.
Jimmy Angel, he types. Crossing the fingers of one hand, he hits enter with the other.
Holy shit, yes.
Doctor Hypnogasm takes down Arachno Man and Superb Man. There’s an entire series of “Str8 Dudes Tricked at Gloryhole” with Cas on his knees on one side of a split screen, blowing a dude while a girl makes noises behind Cas.
Dean fucking delights in all of them, especially the ones where the tricked guys get “mad” and fuck Cas in punishment. It’s so much better than how it would have gone in reality (although Dean’s painfully aware how low that bar is). The look on Cas’ face when they pound him. The fucking rapture. His half-closed eyes, his half-open mouth. The way his cock bobs as they hammer into him, Cas just as hard as the fucking.
There’s a video Dean’s pretty sure got tagged wrong, Cas and a stunning female bartender hitting it off, but Dean’s fine sitting back and watching “Ebony cock surprise” for a palate cleanser.
Except, no, she’s trans, and she fucks Cas’ mouth so lovingly, Dean comes before the halfway point of the video.
So, yeah. Mislabeled on the gay part, totally accurate on the title.
Dean finishes up that one the next night, or rather, it finishes him up. There’s just something about Cas getting fucked in the ass to the sound of sweet endearments. There’s one bit Dean watches over and over, a ten second span of absolute greatness where Cas lets out a startled laugh and his dick twitches up off his stomach. Dean wants that burned into the back of his eyelids.
He watches everything he can find, from the “unsuspecting” Mormon missionary one where Cas plays a teen walking into an orgy, to a “demon sacrifice” one with Cas tied up as a succubus feeds on his dick and ass.
There’s so much good shit, right up until Dean runs out of it. He’s back to the land of repeats for a good while, but as those grow stale, the addiction breaks. Dean’s porn habits go back to usual, and he searches for new Jimmy Angel stuff maybe only once or twice a month. It fades into the background, just a piece of his new normal.
With the one-two combo of Christmas and then Dean’s birthday coming up, Sam makes the same phone call he makes every year.
“What do you want, Dean?” Sam asks. “And don’t say porn.”
For the first time in a long time, it occurs to Dean that asking for porn wouldn’t actually be a joke.
“Uh,” he says instead. “Gift card?”
The Doctor Hypnogasm stuff is easy to find. The rest takes some doing.
And then it takes even more doing.
After a certain point, it moves from whim, to obsession, and back down to basic stubbornness. Dean prowls the underbelly of the internet and finds a Jimmy Angel fan club. He finds the full film biography, all that’s available on DVD, and he prints out a checklist.
As it turns out, there’s stuff even older than the library videos. Casa Erotica videos, about half a dozen years old and now obscure as shit.
Which means, when the following year rolls around, Dean braces for a weird conversation.
“And don’t say porn,” Sam says, as always, this year in person.
“What if I want porn,” Dean answers, pointing his beer at Sam.
“You can buy your own Busty Asian Beauty mags,” Sam tells him flatly, unamused.
“Yeah, that’s not what I mean.” Dean leans forward.
Sam’s eyes widen. “...You’re actually serious.”
“So… You still know Gabriel, right?” Dean asks.
Sam switches from disbelief to glaring.
“I’m not joking,” Dean swears. “He still works with Casa Erotica, right?”
“Dude, he owns the place now,” Sam says, absolutely betraying that they’re still in touch.
“Awesome,” Dean says. “‘Cause there’s a kinda rarer one I need.”
Sam pushes back from the table, hands raised. “I don’t want to hear about your needs. Really don’t.”
“If I tell you the actor’s name, can you get the goods?”
Sam pulls a face. “...Maybe. But you owe me the best Christmas presents of my life, and you’re not opening your gifts in front of anyone.”
“Deal,” Dean agrees.
When Dean emails over the info, asking for Jimmy Angel or Castiel Novak, Sam emails back, asking, Why do I know the name Castiel Novak?
...Right, the obvious downside to this plan.
Dean counters with I don’t know, why does anyone know a porn star’s name?
The next day, in triumphant capslock, Sam emails, THAT WAS THE NAME ON ALL YOUR NOTEBOOKS! DID YOU GO TO HIGH SCHOOL WITH ONE OF GABE’S PORN GUYS???
Dean doesn’t email back. In fact, he absolutely refuses to answer unless Sam watches him unwrap his lovely new DVDs.
Sam doesn’t call the bluff, because he knows it isn’t one.
All told, by the time their tenth reunion is rearing its head, Dean has Cas’ entire pornography collection on his shelf, hidden tastefully behind his box sets of Battlestar Galactica and Buffy. (Years of being a library aid may have left Dean with a tendency to alphabetize.) It’s a weird way for a fantasy to come true, but then, how many people get to see the naked body of the One That Got Away? Let alone see that person come time and time again.
While the porn performances are all well and good, there’s a little corner of Dean’s heart that has fondly gone against alphabetizing the DVDs. He’s stacked them chronologically instead, working off the growing swaths of art and color across Cas’ body.
By now, the angel wings are amazing, black and dazzling, the light tan of his skin serving as the feather shafts in a beautiful display of negative space. He’s decked out in nerd references all across his body, some hidden away inside more organic designs, and that’s where Dean feels like he still knows the guy.
Yeah, that shy nerd he’d crushed on and fantasized about protecting, that skinny guy may have filled out and become a porn star, but Cas is still an absolute dork when it comes to science fiction and fantasy. He doesn’t stammer at all in the behind the scenes interviews, doesn’t blush or look away from the camera or interviewer.
In the blooper reels, he laughs a lot. In some of them, he dryly goes off-script, making his co-stars break character and burst out laughing. Dean watches those without even jerking off, but it’s still wholly satisfying. Whoever Cas is now, he’s an awesome guy.
Maybe Dean really won’t ever see him again, but when the invitation to their tenth year anniversary lands in his mailbox, what the hell.
He takes the chance.