Chapter Text
Dean checked himself in the full-length mirror. Everything seemed in order; smooth, freckled skin gleaming with moisturizer, the small nipple rings shiny and catching the low light in the room. He pulled on tight electric blue boxers, covering them with black slacks. They were from his day job, but no one needed to know that. He finished the look with a white shirt, sleeves rolled, and a shitty grey tie that had definitely seen better days, but it was only a prop so no worries.
His room was set up just-so, though it had been a pain to shift his desk around so there was a plain wall behind him. He’d hit the jackpot with a single room, but the trade-off had definitely been space: it was barely larger than the janitor’s closet. He should know, that was his other day job.
When Sammy had announced he got into Stanford – on a full ride, no less – Dean had been ecstatic. His own scholarship was tuition and accommodation only, and he’d managed to cover the rest of their costs with his jobs as a barista and janitor for the college, so he insisted his brainbox of a little brother focus on his education only, and didn’t take on any other work. Of course, Sam had ignored him, but as he’d managed to get a summer job in a prestigious law firm, Dean couldn’t really argue.
But then, Sam had the chance to study abroad for a year, at Oxford. Costs which weren’t covered by his scholarship. He’d saved enough that he could afford half the cost himself, and was intending to get a loan for the rest, but what kind of shitty big brother would Dean be if he allowed that? So, he might have told a white lie, and told Sam he’d saved enough to cover it. But, he was only just scraping even, and he couldn’t ask Bobby, who’d basically brought them up, as Moose had been eating him out of house and home for a decade (and, okay, Dean could put away a fair bit in burgers and pie himself). As it was, Dean had fully intended to save up to pay Bobby back some way, as soon as he was free from college and earning real money. That was part of the reason he was so insistent about not getting into debt now.
So, with only six months before Sammy would be needing that influx of cash, Dean had to think real hard. The answer had come by accident, more than anything. Charlie, his best friend (outside of Sam, anyway), had made a passing comment about gay men being thirsty fuckers. It hadn’t been entirely unfair – they’d been in a gay bar at the time and, well, that spoke for itself – but it had got Dean thinking. It was his opinion that gay men did not hold the medal for being thirsty, but they might hold some medals in other areas, like, say, being willing to pay pretty boys to fool around on camera.
Dean, being a very pretty boy (he had no illusions about the effect his thick lashes and pouting lips had on men), had researched and chosen a reputable streaming service for cam shows before the evening was over, with Charlie’s help. The two best things were that you could save videos, so see a revenue from subscriber views, and there was no fee, rather the company took thirty percent of income instead.
It had been slower to pick up than he hoped – a lot of the popular boys did it as a real job, so were happy to tout for business on social media – but after two months he had a good selection of regulars and a steady income stream. If it kept going at the same rate, at the end of the six months he’d be comfortably able to send Sammy all the money for his trip, and be able to retire his webcam forever.
It had become apparent that all the nice men like a gimmick, and Dean’s was role play. It had happened by accident, when he’d almost missed his start time due to a basketball practice that had run late, and he’d started his show in his generic red and white jersey and shorts. His usually fairly quiet messages had lit up, with praise (that, frankly, Dean couldn’t get enough of) and with suggestions. Suggestions of the ‘is the coach going to punish you?’ and ‘show us what happens when you get to the locker room’ variety. Dean went with it, and after that, he started to take requests, and even offer prizes to high rollers for personalized shows. Sure, sometimes the kinks pushed his boundaries a little – and there’d been a few he’d had to block – but his income literally doubled at that point.
The show he was dressed for was a personal request from his favorite fan; codename: ThursdayKnight. He’d won the choice in a war of ever-increasing tips that was going to pay close to a week’s accommodation for Sam in Oxford, so Dean was more than happy to acquiesce to the request for some office-based roleplay. It wasn’t only because Thursday won the wars more than most that he was Dean’s favorite. Even though he’d never heard his voice, Dean knew him as witty, and clever, and caring. Almost ever since turning up in Dean’s chat a few weeks ago, he seemed to be interested in Dean’s wellbeing more than anything else, and, for that, he was unique.
Dean checked his phone for the time, and slipped his wire-framed glasses on to finish the look, logging into his account. There were already a few people in, and he flashed a grin at the screen. The old laptop Charlie had given him was just enough in shot, loaded up with the cam page and hiding the spare keyboard she’d also given him, that was hooked up to his actual laptop. It meant he could type messages while ‘in character’ and see the reactions from his guests and regulars. They liked it when he spoke off screen like there was someone else there, so he just kept a side eye on the messages scrolling up his feed, looking for any suggestions of what people wanted, dropping the odd welcome comment to his regulars, and ignoring the ones berating him for taking too long. That was par for the course, but no one was getting anything until the ticker went up high enough, as his regulars knew full well.
He was actually waiting for one message in particular, but ThursdayKnight was sitting silent, even if he’d been one of the first there. Dean decided to try to prompt something, clicking away on the old laptop, biting his lower lip and furrowing his brow as if the figures were just too much for his pretty little brain to deal with. His audience seemed to love it when he played dumb and innocent. He leaned back in his chair, running a hand through his slightly mussed hair and huffing in pretend frustration. He arched his neck back, knowing the camera was catching his profile just right, and it worked. When he glanced down he saw a message from ThursdayKnight.
ThursdayKnight: Be careful, your boss won’t like it if you get too distracted.
He used the prompt, his gaze flicking past the camera, as if someone had walked in.
“Oh, sorry, Sir. Yes, just struggling a bit with this spreadsheet.” He cast his eyes down, as if he were being reprimanded, making sure he kept his head tilted so the low light emphasized his long lashes. The ticker was getting higher, but not high enough yet. A lot of them only tipped to get something happening, and they’d go broke as soon as he gave them something, so he couldn’t peak too soon, although his regulars wouldn’t do him down like that, so he mentally calculated how long he’d have to keep them intrigued at this rate. Another ten minutes should do it, but he’d have to tease the end game.
“Oh yes, I’m sorry, Sir, I’ll try much harder. You won’t need to punish me.” A good flutter of the lashes, and he heard the ticker chime repeatedly as several tips came in. He ‘watched’ his fictional boss leave, and leaned back again with a groan. “God, he’s so hot. What I wouldn’t give to have him treat me real good instead of telling me off all the time.”
Obviously he could never reveal such a thing to his audience, but he had a very particular face in mind as he said that. He’d had a professor his first semester; Econ 101. Basic stuff, just a mandatory course. The guy was beautiful, there was no other way to think of him, and Dean brought his hand up, rolling a piercing through his flimsy shirt, thinking of the guy’s deep blue eyes and scruffy black bed-hair, his warm tanned skin and wide, white smile.
The guy had given Dean mental-fodder for having to do this stuff on screen more times than he could think of, even if, these days, he only got the vaguest glimpses when he was rushing to classes at the Business Faculty, but the distraction was perfect as, when he opened his eyes, having loosened his tie and unfastened several buttons, the ticker had climbed to a level that he deemed acceptable to move onto the next stage.
He had to do this right, because he was hoping ThursdayKnight, for preference, would want to stick around for a private show after, and really make this evening worthwhile.
He was still playing with his nipples when one of his other regulars, SnakeCharmer69, chimed in.
SnakeCharmer69: Ur boss is gonna be mad if he catches u playing boy gonna mess ur tight little hole
That was one of the reasons he liked ThursdayKnight so much, ironically. Oh, he was as kinky as the rest of them, but he was strangely (sexily?) formal in his messages, and somehow, despite what they were all there for, he managed to never make Dean feel like nothing more than a hot piece of meat.
Guest 248: Come on slut give us what we paid for stop teasing whore
That message was from a guest account, who hadn’t tipped a penny, so Dean felt nothing as he booted the profile.
ChatBot: Guest 248 was evicted from the chat scrolled up, which got some excitement going in the chat with people wondering why, some of them clearly pissed at Dean for kicking him.
ThursdayKnight: You did the right thing, Impala67. There was no need for him to speak to you that way.
Impala67: Well, not if he isn’t going to pay for the privilege, that’s for sure
Dean winked at the camera, but it was time to get this show on the road anyway, so he looked up again, as if his boss had returned, and put a wobble in his voice that he knew would have half his regulars creaming at how naïve it made him sound.
“I’m so sorry, Sir. I just can’t get the figures to balance. I tried everything…I know, but please don’t fire me, I’ll do anything. Anything, Sir. Please.” He pouted his lips, widened his eyes, and tilted his head. He knew it was adorable, because his spank-bank professor did exactly the same move when he was confused, and Dean had wanted to eat the guy alive the first time he’d seen it. “Oh…but I’ve never done that before, Sir. I’ve never sucked anyone’s cock.”
Dean fluttered his lashes again as he brought out the piece de resistance: a very realistic cock dildo, with veins and a fat head and the softest, synthetic skin. It would have been perfect anyway, but tonight it was a special treat for ThursdayKnight, as he’d purchased it for Dean from his wishlist.
ThursdayKnight: I recognize that 😉.
Dean didn’t reply because he didn’t want to break the mood, but he flashed the quickest grin before going straight back to character.
“I’ll do my best Sir, for you.”
Dean proceeded to give the dildo the best blow job it had ever had, lathing the fat pink head until it was slick and shiny, flicking his tongue around the length, and tilting his head back so he could show his audience it slipping into his throat, until his own cock was trying its darndest to break free from his tight boxers and he’d almost forgotten the show. He came to with a start as the quiet notes of his tip jar rang, noting that the comments had blown up again with encouragement and appreciation. Worth it, but this could come to an end now, particularly as he’d just secured Sammy food for a week.
He pushed his chair back, unbuttoning his shirt all the way, and his dress pants, one-handed while he kept mouthing at the dildo, fishing his cock out, playing with it a bit – all part of the show – before working it with intention – ignoring the calls to fuck himself with the fake cock, for now. It took a couple minutes, but soon he was painting his own flat stomach with his thick release, running his fingers through it sensuously as he thanked his audience.
SnakeCharmer69: U gonna let me into a private chat so I can watch you fucking yourself with that thing? A private chat request window popped up, but it wasn’t SnakeCharmer69.
“Sorry, Snake, got an appointment to fulfill. See you guys next time.”
“Hi Thursday,” he purred into the camera when he’d accessed the private chat. “Was it worth the bidding last session?”
ThursdayKnight: Always. Do you like your new toy then?
“Very much. Do you wanna know why I put this one on my wishlist?”
ThursdayKnight: Yes.
“Because it looks like a real cock. I’ve always wondered…” His fluttering eyelashes were a little for show, but his flushed cheeks were real.
Dean wasn’t even sure why he was being so honest with this virtual stranger, outside the connection he wasn’t sure if he was fabricating. He’d known he was gay for a while – a long time – but it wasn’t until he arrived at college, and met Charlie, who was so out-and-proud she was a one-woman gay pride march, that he felt brave enough to actually be it. But even though he was comfortable with who he was – even more so when Sam had accepted the announcement with a smile and a thumbs up over their skype call, saying all he wanted was Dean to be happy – he hadn’t really had time to do much more than focus on keeping his, and then Sam’s, head above water. On the rare occasion he went out, he was more interested in being with his friends than losing it through some meaningless one-night stand.
But what he had with Thursday, even if it was actually nothing more than his imagination, delved into the realms of friendship. Sure, Dean did sexual stuff in front of a camera in the hope of getting money for Sam’s trip, but when they were in private chat, it felt like there was more to it. Dean didn’t think the way he felt was helped by knowing Thursday lived in the same city as him, because he'd given it away more than once when they’d talked about what they did with their downtime. It made Dean wonder whether they’d ever walked past each other in the street.
ThursdayKnight: Impala? You’ve gone very quiet. Are you okay?
“Sorry, bud. Got distracted. Can I ask? Do you think, if we hadn’t met this way, that you’d want to speak to me?”
ThursdayKnight: You’re extremely beautiful. I’ve no doubt I’d want to, but I might not be brave enough to approach you.
“Nah, not that. I mean, say we had mutual friends, or something, and we spoke to each other…”
ThursdayKnight: Like friends? Definitely. I find you very good company.
Dean flushed, as he so often did at Thursday’s direct way of speaking. “Okay, that’s good. I think we would have made good friends.”
ThursdayKnight: You seem strangely maudlin this evening. Can I ask if something is bothering you?
“Sorry,” Dean huffed out a weak laugh, “I’m not giving you your money’s worth tonight.”
ThursdayKnight: I’d rather you didn’t even think on that. Besides, you’ve done more than enough to respond to my fantasies tonight. Is there something bothering you?
“It’s dumb. It’s just, doing this, just tryna get the money together for my brother’s school, it doesn’t leave much time for other stuff. Is it totally stupid that I put that dildo on my wishlist because I thought it would be like a real one? And it’s not. Well, I don’t think so, though I only have my own to compare it to.”
ThursdayKnight: You haven’t touched another? Ever? But you do this.
“I know. I’m a total slut.”
ThursdayKnight: Absolutely not what I said. I’m just surprised. You come across as extremely sexually precocious.
Dean actually colored, belying his next words.
“Well, I aint no blushing virgin, not really. Can’t claim that when I use as many toys as I do in my shows."
ThursdayKnight: I certainly can claim that.
Dean wasn’t sure if Thursday was unsettled by his admission. That’s the thing about text. He wished he could hear Thursday’s voice, wondered if his real speech would be as precise. Wondered if he’d sound shocked, or if he’d be turned on right now.
ThursdayKnight: Would you care to hear why I chose that particular model from your wishlist?
Dean nodded rapidly, sucking his lower lip between his teeth.
ThursdayKnight: Because it is very similar in length and girth to my own penis. I must express that I felt the opportunity to watch you with it was too great to pass up.
Dean let out a coughing exhalation.
“Oh, okay.”
ThursdayKnight: I’m sorry. Is that too much?
“No. No, really. It’s all good.” Was it too much? Dean wasn’t really sure, despite his assurance. But he was already having so many illicit thoughts with a shadowy representation of this man, and now he had one solid anchor point he had a feeling the fantasies were about to get a lot more x-rated.
“Um…would you like to see me fuck myself on it?” He was suddenly feeling uncharacteristically shy and almost had to actively remind himself what he was here for – what Thursday was literally paying for.
ThursdayKnight: Only if you are comfortable to. I am aware you already ejaculated once this evening. There’s no need to make yourself overstimulated.
“Fuck, Thursday, you’re killing me here. I want to. Promise. For you.”
He moved back, so the camera could catch him squeezing lube directly onto his taint, allowing it to roll thickly until his crack was coated, adding in a few over-exaggerated moans and shudders. His audience loved that stuff, though, funnily, Thursday didn’t ever seem overly-invested in that side of it, and Dean wasn’t sure if he should be freaked out how easily he saw past it, and instead praised him on the flush of his skin, or how blown his eyes were – the involuntary things he wasn’t hamming up.
ThursdayKnight: Such a sweet boy, working yourself open for that big toy.
Dean snorted. “Way to compliment yourself.”
ThursdayKnight: Well if it’s a compliment that’s deserved, why not? I do wish it was my fingers twisting inside that hot, dark hole, though.
“Thursday.” Dean’s voice came out even huskier than he’d been going for and, not for the first time, he really wished he had an actual name to call out. And an actual voice to replay in his fantasies. “Wish I could hear you.”
ThursdayKnight: You do?
“Yeah, bet you sound sexy as fuck.” It was a gamble. Dean knew it was even chance that Thursday would have a high-pitched whine of a voice instead of the kind of tones that would help him reach orgasm, but it was a risk he was willing to take.
He still jumped when he heard it, though, whispered through the speakers.
“How’s this?”
“Fuck, Thursday, warn a guy.” But then he threw his head back, adding another finger. “Worth it, man. You have one sexy voice.” He did, even whispered: gravelly with arousal, and Dean could almost imagine it murmuring appreciation right into his ear.
“You look so beautiful, stretching yourself like that, that sheen of perspiration across your chest showing just how hard you’re working yourself.”
“I like you watching me,” Dean admitted, though he wouldn’t go so far as to admit it was solely Thursday he liked watching; he was the only one Dean actually got off on. He refused to get flustered though, dribbled lube on the head of the rubber cock instead, giving Thursday a bit extra, stroking it with a twist, looking into the camera and biting the tip of his tongue in concentration.
“Those eyes. I don’t think you even realize how beautiful you are.”
Dean shrugged. He knew he was hot. Pretty. Sexy. Horny. Available. All those buzzwords his followers liked to spit.
As if he could read Dean’s mind, Thursday chuckled. “No. Purely beautiful. Sweet and charming. Hiding behind something.” Dean flushed, swallowed heavily.
“Do you want me to keep going with the role play?”
“Not this time. I- this time don’t add any accoutrements. I just want to see you feeling pleasure.”
Dean had no idea why, but that almost made him want to cry. He cleared his throat, winked down the lens.
“Sure thing, boss.” He put the head of the dildo against himself, twisting it a little, applying firm pressure until it popped through the relaxed muscle. He started to work it, taking his time pushing each inch inside, not bothering with the fake noises, but letting out a few breathy moans anyway just at how perfectly it filled him. Thursday was silent too, only little gasps of arousal that suggested to Dean he was doing something in the way of pleasure on his side, too.
Dean was stroking his cock with his free hand, having to repeatedly slow down – he needed to give Thursday value for money.
“Please, don’t stop.” Thursday sounded almost desperate, and Dean almost teased, but instead he found his hands speeding up, applying more pressure, deciding that finishing at the same time was somehow significant. “Will you come for me, Dean?”
“Yes.” It was more a whimper than anything, and Dean arched off the chair, splashing himself as his muscles threatened to expel the toy of their own accord. He heard Thursday finish at the same time with a desperate groan, and Dean felt a ridiculous sense of pride.
ThursdayKnight: Thank you, that was incredible, as ever.
“Hey, why radio silent now?”
ThursdayKnight: I won’t be able to come to your shows again. I’m sorry. For some reason Dean felt a sense of betrayal, almost as if he’d thought they’d experienced something real together and Thursday was blowing him off, metaphorically grabbing his clothes and sneaking out the door.
“Sure. Fine. Can I ask why? Did I do something you didn’t like? Was it because I told you I haven’t been with a man?” He tried not to sound like a whiny teen, but he knew he only had limited success. At least he wasn’t fucking crying at the rejection.
There was a long pause while Dean tried to breath calmly.
ThursdayKnight: No. Jesus no. You were perfect. Just like always. I just can’t do this anymore. Was there something there, that Dean could latch to?
“Why not? Please, you can at least give me a reason.” He didn’t say because he deserved that much, because that was definitely taking what they had too far.
ThursdayKnight: I am in a very awkward position, ethically. I have already taken this much farther than I should have.
“I don’t care. Does that count for anything?”
ThursdayKnight: If you knew just how morally bereft I have been you would not be saying that, I can assure you.
ChatBot: ThursdayKnight has left the chat.
Dean still refused to cry, but he was numb as he cleaned up the mess from his evening’s work.
It wasn’t until he was laying in bed, uncomfortably far from being able to sleep, that he realized ThursdayKnight had used his real name.