Stiles hadn’t meant for it to become a thing. He’d just been interested in helping out his fellow man. Ever since he’d realised that perhaps he found the ocean to be a little larger than the pond he’d been swimming around with Lydia in, he’d decided to do some ‘research’ into gay porn.
Stiles was thorough, what can he say? Google-fu and all that. There was little outside the reach of his fingertips, especially after how hardcore of a research nerd he’d become in the wake of his best-friends moonlit problem.
It’d taken while, to learn himself more fully, or as fully as one could in the domain of theoretical sex. He’d found his preferred sites, learned his preferred kinks, and settled in nicely, trolling the web in his spare time (what little there was, now that he actually had an active social life - though really, could it be called a social life when the most conversation he got out of the Derek and his merry gang were growls and threats to his life?).
As one might expect, Stiles largely engaged with porn passively, but as time passed, and he grew more bold, he began to notice in the live chat feeds that littered the sites just how often people lamented there not being enough twinks with nice fucking legs around.
Stiles couldn’t help but think;. Legs? I have legs. Good legs, I mean. Pretty good legs, totally. I could pass as a...twink. Sure. Yeah? Yeah!
Seriously, the boy could pull off skinny jeans like a hipster god.
So... he’d... experimented. He started off by buying vats of nair, and when his dad noticed he’d complained that all his friends had hairless upper bodies, so why not him? His dad, typically, had given him the “you look handsome despite all things” talk, which - really dad? Anyway.
Stiles liked it. A lot. Having smooth skin made him feel like a different person - and it was secretive. Not something that anyone would notice, not like dressing in drag or wearing makeup; but it made him feel like a girl. Aaaaaand apparently he had a thing for feminization; so sue him.
This thing had sort of just devolved from there. He’d finally gotten the courage to post some of the amateur videos he’d taken of himself to the site he most frequented, and it had been crazy popular.
And for the first time in his life, he, Stiles motherfucking Stilinski, was in the spotlight. For being hot. He realised just how inherently narcissistic it was to feel that way, but hells yeah, power tripping.
It was completely insane. People were offering to pay him money. And Stiles didn’t exactly have the time for a part time job, not with the crazy hours he was pulling fighting supernatural crime, so he thought; why the fuck not?
So he became an amateur porn star, featuring his body from the neck down, or covering most of his features with a hood (seriously, he was paranoid, and for good reason) running his shit through so many IP bouncing systems that no one short of the FBI could find him (or possibly Danny)
At first he started off vanilla; straight edge by comparison to most of the shit on the web, except for his signature piece of equipment; a shiny red ball gag, which served the purpose of effectively keeping his stupid ass comments from ever being heard, or worse; recorded for posterity on the internet, in case he dropped some sort of bomb. He went by the name LittleRed, and as part of his super secret disguise, often wore a red hood that covered the top part of his face; a little piece that he’d taken out of a woman’s ‘Slutty Red Riding Hood’ Halloween costume.
Yes, he thought he was hilarious. It was that or call himself Red Hood, and he didn’t think Jason Todd would appreciate this kind of publicity.
The more popular he got, the more he started looking into requests, which banked more. Panties, stockings, cockrings, nipple clamps, painted nails, buttplugs. And it turns out people were willing to shell out the cash for him to pay for them. And then came the day that someone requested this dildo from an online store - one of a kind. A werewolf dick, complete with a knot. Stiles didn’t want to admit how much he’d fucking fantasied at this point, but seriously, some chick on online was offering to buy this thing for him (which he mayormaynothavealreadyconsideredbuyingbecausehewasasicksonofabitch). So, one week later with express shipping, and he could official add the hashtag for knotting into his profile. Stiles was insanely popular, and raking in the cash.
Everything was going smoothly. He made it clear that no wolves were to interrupt him during certain times, claiming he had a designated “Stiles Time,” during which he did his homework, or his gaming. This seemed to go down well with everyone, but he wasn’t an idiot. He always made sure to draw the blinds and put up an ash barrier.
But then people (see; Derek) started getting suspicious of how much cash he had when he started showing them cool new magic books that were like 500 years old, and the awesome new herbs he’d special ordered from across the globe. Stiles assures them they can fuck off about his money, he just has some shit going on on the internet. He doesn’t try to lie about it, since that would be obviously be an effort in vain.
Derek, inevitably, being the stupid alpha asshole he is, senses the slightest hint of a lie where none of the betas could tell.
“I can hear your heartbeat, Stiles. What the fuck are you doing.” Predictably, it’s not a question. And predictably again, Derek has his alpha pants on and his glaring at him with those stupid eyebrows all like ‘what the fuck, Stiles.’
And Stiles, because he knows a losing battle when he sees one, turns it around on him. “Look, I’m not going to tell you the truth, so I won’t bother coming up with lies. This money is helping me become an awesome sparkly magical girl like from an anime, and these archaic tomes of arcane knowledge don’t exactly run cheap. Plus, I’m planning on making a mystical garden of questionable herbs in my backyard, and questionable herbs ain’t cheap either.”
So Stiles continues his thing (is there an appropriate name for this?), enjoying the attention at some basic psychological level, considering how ignored he’s been in favour of all the stupidly beautiful wolves in his life. So what if he’s underaged and committing felonies out the ass. At least he’s getting paid to do it.
And then one night it all goes to shit.
Or at least he thinks it does.
He’s worked himself up into a lather with the giant black knotted dildo tucked up so neatly inside him, on his hands and his knees with his head purposefully out of shot, and he does a quick check on the live chat he has running through a feed on his phone in front of him so that he can see what requests he’s getting for the big finale when he sees a new entrant into the livestream.
He literally pauses. Just tenses up, fight or flight reflex kicking in as the name registers. He’s immediately spammed by the others in the chat, telling him to hurry up and fuck urself on dat nice big cock and he can’t fucking breathe. It’s like a panic attack but a million times worse because he’s on camera with a giant dildo stuck in his ass.
Then logic reasserts himself, because Sourwolf88 cannot be Derek, because Derek doesn’t know what the internet is, and definitely does not watch porn. Let alone twink porn you have to pay for. With knotting.
Holy fucking shit.
Stiles tries to get over himself, finishes himself off the best he can, tries to coach himself, trying desperately to regain his swagger, and types a quick apology for the slight issue before shutting it all the fuck down.
As the laptop slams shut where it was sitting on his desk, recording him on the bed, he feels numb.
There’s no way.
I mean, come on. Of course people are going to have wolf related names, looking at some kinky knotting video. This isn’t the first lupine pun he’s read; some of them are even more cringe-worthy. But jesus.
Stiles tries to put it out of his head, and continues for another couple of weeks with his Wednesday showcase (it’s statistically proven that little to no supernatural shit goes down on Wednesday, so he feels fine taking this as a holiday from shenanigans.)
It’s going swimmingly enough; he still has his street cred on his site, and is in the middle of a provocative strip tease when he hears the chime of another person having entered the chat.
Stiles is rocking in a pair of cute frilly-laced red panties that cup him just right, pulled taut across his sharp hipbones. A pair of matching stockings cling to the smooth skin of his thighs, held up by a garter belt that draws attention to just how long his pretty legs really are. He’s just shimmied seductively out of the waytooshort schoolgirl skirt when he looks up at the screen, eyes shadowed by the low hanging red hood that is the source of his moniker.
His face spasms when he sees the daunting Sourwolf88 pop up, but he immediately hardens his resolve. That isn’t Derek. He will keep on keeping on and do his shit, because he has been blessed by the twink gods and the world loves him. (well, more like 40-odd weirdo pseudo-pedophiles love him, but hey, he’ll take what he can get). So Stiles continues with his little strip tease, leaving the garter on but slipping off only the panties, so that his cock brushes against it, smearing precum over the soft red lace.
He leans over the keyboard and asks for some requests, letting them get a good look at his chest.
Among the typical lewd responses like ‘give me ur address, i promise ill rim u real gud’ and 'I wud spank u til dat ass is red’ which Stiles ignores, there are a couple of actual propositions.
Put on your nipple clamps. Good grammar, proper spelling and punctuation, if a little bossy. A man after his own heart. Of course, it has to be Sourwolf88. Stiles huffs a bit, and bends down to retrieve them off his bedspread, and teasingly puts them on, allowing a little smirk to pull at the slim visibility of his lips where they stretch obscenely around his red ball gag.
Now take out your gag and show me if your mouth is even useful. I want to see you take that werewolf cock you’re so fond of.
Stiles’ heart flutters. He’s never done this on camera before, mainly because he’s too afraid of people seeing his face. But he’s practiced. Oh fuck has he ever. He has an oral fixation and he’s not going to deny it. And of course it would be Sourwolf88 again who suggests it. With shaking fingers he reaches behind his head and starts undoing the clasp for the gag, and the chat is flashing manically. People offering their own cocks, telling him to choke on it, that they want to fuck that pretty little mouth.
Do it. I know you want to.
Stiles is achingly hard and he hasn’t even touched himself yet. He turns to grab the specified dildo and angles the camera of his macbook so that he can sit in the computer chair comfortably without worrying about the angle showing too much. He presses the fake cock to his lips, teasing it with the tip of his tongue. He’s already breathing heavily.
There’s a reason you like keeping your mouth full.
Stiles whimpers, and moves to mouth down the cock, almost slipping up before catching a glimpse of himself on the screen. He angles away, and works the tip into his mouth. His eyes flash to the chat on the side of the screen. He ignores everyone, waiting for that familiar handle to come up again.
It’s terse, sharp and commanding and Stiles can’t help but think about Derek, about his Alpha telling him what to do. He’d always liked to rebel, but secretly he’d always wanted to submit to the older man. Fuck. He takes more into his mouth, gradually, because jesus this is thick. He usually practiced on the smaller dildos he had. He’s barely halfway when another message pings up.
You think I’d let you take your time? I’d shove my cock down your throat and make you take it. You can do better than that.
Stiles moans. Fuck, if this isn’t Derek. He feels his cheeks flare with heat, want, and embarrassment for thinking of his alpha like that, but part of him just wants to please, wants to do what he’s told, so he pushes his mouth down until his lips brush the knot. He can’t stop the fluttering in his throat as he works against his gag reflex, can’t stop the saliva that’s slipping out around the cock, sliding down his chin. He feels obscene. He trails a hand down to touch himself, because he’s not sure how much longer he’s going to last.
Did I say you could touch yourself?
Stiles whimpers, stilling sharply before drawing his hand away.
Now fuck your mouth with it.
Shuddering, Stiles complies, pushing and pulling the cock and watching his distended lips drag up and down the terrifying length of it. He can’t believe he’s managed to fit it inside of him; can’t believe he can take it in his mouth.
Would you let me knot your mouth? Would you let me cum down your throat and make you choke on it?
Stiles is whining constantly now, his hands twitching with the need to touch himself, but he won’t.
I bet you’d love it. You’d take it all and ask for more like the good little bitch you are. I’d cover you with my cum, force you to swallow it, and then I’d fuck into your ass and breed you until you couldn’t possibly take anymore.
Stiles feels his heart stutter to a halt in his chest, his throat tightens with want, and, beyond all belief, he can feel his balls draw up and his cock twitch, the pooling heat in his belly like an inferno as he stops breathing and just loses his mind. He’s coming, uncontrollably. It fucking rips out of him and he’s ruined.
His whole body is shaking, and he barely manages to pull the dildo out of his mouth with a sloppy pop, throwing it heedlessly on the desk. He feels destroyed, and only barely passes a cursory glance back at the chat out of a fatalistic need.
I don’t think I told you that you could cum. But then, you’ve never been very good at listening, have you?
Stiles feels cold, even as his body flushes, and his cock gives a twitch that humiliates him. He sucks his bottom lip into his mouth to stop anything embarrassing from coming out.
But you’re going to listen now, aren’t you.
It’s not a question. Stiles nods without thinking, eyes fixed on the chat, ignoring the constant stream of the other viewers clamouring for his attention.
You’re going to shut your computer down. You’re going to break the barrier. And then you’re going to get onto your hands and knees on your bed and wait for me to come and punish you. And if you’re lucky, you’ll get to cum. But you’re going to have to beg for it.
I’ll be there in 5.
“Oh, my God.”