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saccharinesunsetretired · 5 months

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Wilbur Soot’s Guide to Side Hustles | camboy!Simpbur x camgirl!reader | Part One

My first ever series on this blog yayayayay! Also first time writing Simpbur. No fucking clue when the next chapter will be up though. Could be next week. Could be a month. Life contains many mysteries.

Summary: Wilbur has had a long line of obsessions in his time. In a desperate attempt to get the attention he craves, he starts making content online. When he encounters you at a party full of other creators...well, he's never been good at staying away from things that draw him in, and you may very well be his undoing.

Warnings/Tags: sub!Simpbur, dom!reader. Unrealistic sex/depictions of sex work (although I did try), smut, pegging, general simpbur creepiness, discussions of virignity/consent, low self-esteem and insecurity problems, unhealthy attitudes toward sex. Reader is AFAB and a woman

Word Count: 11.3k

MINORS DNI - BLOGS WITHOUT AN AGE INDICATOR GET BLOCKED, NO EXCEPTIONS

“Hey, creep.”

Wilbur blinked and looked up from his math textbook. Standing right in front of him was a girl from his English course, a girl he’d had a crush on for years. They had never actually spoken. Instead, he’d done what he did best—watched from afar and stayed out of it. For a moment, despite her harshness, he just stared, basking in her attention.

She laughed, and her friends laughed from a few desks away as they looked on. “Do you know how to speak?” she asked.

“Y-yeah,” he said. He could feel his cheeks burning. “What’s, um…what’s up?”

“‘What’s up’?” The girl laughed again. “I’ve seen you hovering near my locker, you fucking pervert.”

Wilbur froze. “I-I wasn’t—“

“Oh, you weren’t?” She leaned against a nearby desk. “Who’s been leaving me notes, then?”

Wilbur wanted nothing more than to curl up in a hole. He had been leaving notes. And admittedly, yes, some of them were creepier than others. The notes ranged from Good luck on midterms :) to You looked so hot in class today. And despite Wilbur’s general lack of self-awareness, he recognized how this looked. “I’m sorry,” he mumbled, avoiding eye contact. “I’ll stop.”

“If you don’t, I’m reporting you,” she replied. “Stay the fuck away from me.”

“Got it.” Wilbur had never felt more embarrassed. The other students began to whisper. He could feel a million eyes on him—well, what felt like a million, at least. “I’m so, so sorry.” He stared at his desk as his eyes stung.

“Good.” The girl stood there for another few moments. “It’s a waste,” she said. “You could almost be cute, if you weren’t such a freak.”

Present Day

You could almost be cute if you weren’t such a freak.

Wilbur remembered that, because of course he did. It was the closest he ever got to someone returning his affections. Yes, he knew it was pathetic, but that shred of affirmation went a long way.

He started bettering himself. It started with better hygiene, not wearing clothes multiple days in a row, properly washing his hair. His parents had been bothering him to do that for ages, anyway. He dressed better, tried to socialize. That last point didn’t go too well. He got bullied to the point that he ended up switching schools and had to deal with the fact that at least a bit of it was warranted.

He never saw that crush of his ever again. He developed new ones, new fixations. He didn’t leave notes, though, or stalk anyone or do anything to arouse suspicion. He promised himself that he could be normal, that he would be normal.

Well, perhaps he’d intentionally switched classes a few times to “keep an eye on” some of the people he became fixated on. But was that such a big deal?

And then university came. Loans, what felt like a million dollars in debt. One night, the result of a drunken decision, he filmed himself getting off. On an even more questionable drunken decision, he posted it online to some internet forum he had only heard of in passing. The second he remembered it the next day (after recovering physically a bit from his previous drinking binge), he was absolutely mortified. And yet, to his immense surprise, people liked it. It wasn’t any sort of viral sensation, of course, but he had a decent number of comments when he woke up in the morning. At first, he was put off by the vulgarity of it, but then, he realized that this was how he could get the high that he’d always craved—attention.

He started working on it. Filming videos, uploading photos. Pretty soon, he had an OnlyFans account going. His content was mostly solo stuff, webcam livestreams and private chats with his more dedicated followers. To his surprise, he started making decent money. It was nice to have something to help relieve some of the university debt. Plus, the validation was nice, even if it was only in praise of his body.

Besides, he had long given up the idea of anybody loving him for anything other than that.

Online, his persona was more submissive. It was easier for him, not having to fake confidence that he didn’t have. Instead, he could let himself moan as loud as he wanted, let the microphone pick up every small gasp and whine as he got himself off either with his hands or one of the million toys that he’d purchased since starting the job. The needier he looked, the better.

Then, he found the confidence to do his first collaboration. The benefits of moving to a larger area for university were plenty, but one of the biggest benefits turned out to be the fact that he was far from the only sex worker in the city. He lost his virginity to a girl on a livestream, although she didn’t know it was his first time. At least, she pretended not to know. Wilbur got the feeling that she could tell. Either way, it had made good content. In fact, it had been so profitable that she had invited him to a small gathering of some other creators—sex workers of all types.

And that was how he ended up holding a can of cheap beer in the corner of a party. It was at someone’s apartment, someone he didn’t know and didn’t care to know. The music was far too loud, the conversation too overwhelming. For a moment, Wilbur was sixteen again, sitting at his desk and wanting to disappear.

At least, until you walked in. You, dressed to the nines for a simple house party. For a moment, he locked eyes with you, and he nearly forgot how to breathe. He looked away first, too intimidated, too afraid. However, he watched out of the corner of his eye as you walked into the kitchen to greet the host of the party and grab a drink.

When you reentered the living room, Wilbur’s eyes immediately went back to you. Suddenly, it was as if nobody else was there. He could feel it creeping up on him again, the beginning of an obsession.

Be normal, he reminded himself. Don’t be a creep.

He watched as you greeted almost everyone at the party, flawlessly interacting with the guests. Clearly, you knew your way around. Eventually, you made your way over to Wilbur. He took a sip of his beer to try and appear casual, only to choke slightly.

“Shit, didn’t mean to startle you,” you said, chuckling. “You alright?” You leaned against the wall right beside him, so close that he could smell your shampoo. Or maybe it was perfume. He couldn’t tell, and honestly didn’t care to discern the difference.

“Fine,” Wilbur replied. He laughed awkwardly, rubbing the back of his neck. “Sorry. You caught me mid-sip.”

“My bad, stranger.” You offered your hand. “I’m Y/N. And you’re Wilbur, right? Allison told me about you.”

Wilbur hesitantly shook your hand before pulling his own hand away suspiciously quick. “Right, yeah,” Wilbur replied. “We did a livestream earlier.”

“I heard. Apparently it was a hit.” You briefly glanced at your phone before tucking it back in your pocket. “And you’re new on the scene…?”

“Yeah, pretty new.” Wilbur shrugged, trying to play it cool and relax his nerves. “That was my first non-solo livestream.” And my first time having sex ever his mind reminded him. Because people only want you if they can profit.

He shook the thought away as you spoke again. “Damn. Pretty good for your first time, then.” You grinned at him. “Most people don’t get this kind of attention so quickly.”

“It’s…definitely been a surprise to me,” Wilbur agreed. A tense silence passed between you and Wilbur. “So…you also do the whole…camgirl thing?” He thought that he’d heard of you in passing, but before, he’d had no reason to look you up.

“Yeah! Two years and going. Still doing mostly solo stuff, but trying to branch out a little,” you replied. “It can be difficult to know who to trust in this industry, who genuinely has your best interests at heart and who is taking advantage.”

“I bet.” Wilbur set his beer aside. It wasn’t that good, anyway. “Do you like it?”

You shrugged. “Sometimes yes. Other times no. Depends on how creepy people are that day.”

Wilbur laughed, nodding in agreement. He watched you as you took a sip of your own drink, some sort of cocktail. “But you make good money?” he asked. His frenzied mind attempted to come up with some flirtatious lines, but nothing else left his mouth. Considering how cringy all the lines were, it was for the better.

“Decent money,” you replied. “And you?”

“Decent money.”

“Cool.” Wilbur felt slightly uneasy as you eyed him up and down. “Hand me your phone,” you said after a moment.

Wilbur blinked. “Why?” he asked. Despite his questioning, he unlocked his phone and handed it over without complaint.

“So I can give you my number,” you replied. You began entering your contact information. “Not to be too forward, but the main reason I came to this party was just to network. Like I said, I’m branching out, and it seems that you’re doing the same.” You handed his phone back. “Maybe we could collab.”

Wilbur felt his heart hammering in his chest. The room felt like it was spinning, and considering he’d only had half a beer, he definitely couldn’t blame it on alcohol. “Oh. Um…you sure?”

You smirked. “You seem harmless enough, Wil. Besides, we can talk a bit beforehand, get to know each other a little. I’d rather not fuck someone without knowing a bit about them.”

“Fair.” Wilbur very shakily tucked his phone back in the pocket of his jeans. He noticed you starting to leave. “We’ll be in touch, then?” he asked.

You winked. “You can count on it.” Only a moment later, you disappeared into the crowd.

Wilbur left the party immediately after. He saw no point in staying if he couldn’t talk with you more. Even after that sliver of conversation, everyone else at the party seemed even more dull than before. He got into the back of a taxi, trying (and failing) to make his brain go quiet.

All he could think about was your skin under the multicolored lights at the party, the sound of your laugh, the brightness of your smile. He checked his phone, and all he could think about was the fact that your hands had touched it less than fifteen minutes prior. And maybe, just maybe, if he played his cards right he would get to touch you for real.

He imagined your hands on him, fingers curled around his cock. Nobody had ever given him a handjob before, but he (for better or worse) had always had a vivid imagination. He closed his eyes and rested his forehead against the window of the cab as he imagined it, your fingers on him. He tried to imagine every detail, the texture of your fingertips, the tone of voice you would use as you praised him.

By the time the taxi dropped him off outside his apartment building, he was achingly hard. He made it to his studio apartment, took off his coat and shoes, and immediately sat on his bed. He opened his laptop and searched for your name.

Sure enough, he found your OnlyFans, as well as the few free teaser clips that you’d uploaded elsewhere. There you were, a vibrator on your clit in one clip, your fingers teasing your own nipples as you moaned for the camera.

He slammed the laptop shut. No, he told himself. No more obsessions. If you manage to make this work, all she’ll be to you is a colleague, a coworker.

Don’t be a creep.

He got out of bed and made it to the bathroom, where he stripped, tossed his clothes in the hamper, and turned on the shower. A cold shower would do the trick, he figured. Admittedly, he’d never actually tried the method, but it was the best he could think of. He could scrub away all thoughts of you, get rid of his hard-on, and call it a night.

He shivered as the cold water hit him. It felt fucking awful, cold water on his skin when all he wanted was warmth, but he toughed it out, waiting for his “problem” to resolve itself.

But it was no use. All he could think about was the sound of you moaning in that video, gorgeous lips parted, legs spread. He couldn’t help but wish he could hear you moan for real, not the fake sort of moans that are exaggerated for the camera.

He gave up after a while and got out, wrapping his lower body in a towel as he did a walk of shame back to his bed. He sat on the towel and reopened his laptop.

He found your OnlyFans page, and without thinking, he subscribed. He wasn’t sure if you could see his username if he used his official account, so he made another guest account. You were worth the inconvenience. He started to scroll. He saw a clip of you and Allison, you grinding against her thigh. Another clip showed you edging yourself into oblivion, cheeks flushed, eyes watering. That was the clip he finally settled on.

He edged himself along with the video, stopping whenever you stopped. If your hand stopped moving, so would his. In his mind, it felt almost like mutual masturbation, like you were really there doing this with him. He imagined you watching him, murmuring praise to him.

It wasn’t often that he got off without toys, not because he couldn’t, but because he was almost always filming his orgasms, and thus toys were usually involved. Despite not having any added vibration or stimulation, he came harder simply from touching himself while watching your videos than he had in months.

He laid there afterward, his own cum on his stomach. He squeezed his eyes shut. You’re absolutely hopeless, he told himself.

And yet, he couldn’t stop now. Not when you were so close.

It took Wilbur three days to work up the courage to text you, and from then on, conversation flowed naturally. At first, it was small talk about the industry—which people did you know, how many parties had you been to, what sort of content were you interested in making, and on and on and on. Wilbur was honest, admitting his lack of experience in the world of sex work, although he didn’t admit his lack of sexual experience in general. If he did, he might scare you off or make you hesitant, and he didn’t want that.

Conversation then turned to more personal matters. Still surface level, yes, but less detached than talks of industry and networking. He learned that you were a camgirl on the side, using the funds to add to the money you made from waitressing as you saved up. He also learned your favorite restaurant in the city (which he offered to take you to sometime, delighted when you accepted the offer) as well as your favorite bands, books, movies…all the surface-level questions he could hope to get answers for.

To his dismay, two weeks of texts went by without you mentioning possibly meeting up to film together. Just when he thought that was off the table and this would only amount to friendship, his phone buzzed as he was working on an essay. He picked it up, assuming it would be either one of his parents or a spam call, and grinned when he saw your name. You were requesting a FaceTime call, so he quickly smoothed his hair before answering.

“Hey!” you said cheerfully. Wilbur was so relieved to see your face, not just on your OnlyFans, but you, you choosing for him to see you. You looked like you were fresh out of the shower, and he realized quickly that you weren’t wearing a shirt. He couldn’t see anything below your shoulders, but the realization still had him speechless for a moment before he regained his composure.

“Hi!” he said back with equal cheerfulness. “How’re you?” He flicked on another light in his apartment so that you could see him better.

“Good,” you replied. A moment of silence passed. “Listen, are you free Saturday?”

“Yeah, why?” The truth was, Wilbur wasn’t free Saturday. He was in a study group for an upcoming exam, but at that moment, he decided that he didn’t give a shit. He would happily flunk an exam if it meant getting to spend more time with you. He had only seen you in person once, and only for a tiny moment in time, and all he had thought about since then was getting more.

“I have a business idea,” you said. Wilbur watched as you sat down on a couch at what must be your apartment. He caught a glimpse of the top of a towel wrapped around your torso, and although this thought made him slightly disgusted with himself, he couldn’t help but be disappointed. Still, his disappointment only lasted a second once your words sunk in.

“A business idea?” He immediately perked up. “What is it?” His mind went wild with possibilities. A livestream? Some short clips? A whole homemade porn film?

“So…your online persona is more on the submissive side, right?” you asked.

Wilbur’s brows furrowed. “How did you know?” Although the two of you had talked about the industry, bonded over creeps on the internet and the like, the details of your content had gone mostly undiscussed.

He noticed the rather sheepish expression on your face. “I may have done some research,” you admitted. “Is that weird?”

His heart skipped a beat, and he had to fight to keep himself calm. You had done research on him? That meant you had definitely seen some of his content, and not only that, but seeing his content made you more interested. Usually, he wouldn’t have cared. If it were anybody else, he wouldn’t have cared, but you? You, the subject of his obsession (he’d finally admitted to himself that’s what it was), the person he thought of every night before going to bed, thought he was desirable? Maybe not desirable, but at least worthy of seeing, worthy of working with. That was enough.

“It’s not weird!” he reassured you. “I…I may have done the same.” He did not tell you that he had a whole folder on his laptop that was only clips of you, that he’d labeled each video, that he’d gotten himself off to every single one. He definitely didn’t tell you that while filming himself the day prior, he’d been thinking of you the entire time. No, that was too much. That was creepy, that was obsession…but based on your admission, he figured a bit of the truth couldn’t hurt.

Thankfully, you reacted positively. “Thank god,” you said, laughing softly. “I thought you’d think I was a pervert.”

“No! No, of course not,” he said quickly. “I would never.” He settled his back against the headboard of his bed. “So, anyway, what was the idea?”

“Well, as I was saying,” you continued, “your persona is more on the submissive side. I portray myself as more dominant. Very convenient for us, no?” Wilbur nodded along as you spoke. “I was wondering…” You trailed off. “I can be forward with you, yeah?”

“Honestly, I’d prefer it that way.”

“Great! How do you feel about getting pegged?” A moment of silence passed as Wilbur’s brain completely short-circuited. He didn’t realize how long he’d been quiet until you spoke again. “Okay, uh…maybe I was too blunt.” He heard your awkward laugh through the phone.

“No! No, not too blunt at all. I’m fine with it,” he replied. “Yeah, no, that sounds great.” He tried to hide the nervous undertone to his voice. Using toys on himself is one thing; being on the receiving end of someone else’s movements is another. “I’d be down for that.”

“Are you sure?” you asked. “You were quiet for a moment, there.”

“Yeah! Yes, I’m completely sure,” Wilbur replied. “You want to, um, livestream that? Or are we just filming…?”

“Just filming,” you replied. “Having sex live is way more complicated. This way, we can try a couple different angles to see what looks best on camera.”

“Right.” Wilbur took a deep breath. “That sounds good. You said Saturday?”

“Saturday, yeah,” you responded. “And I was thinking we do it at my place. No offense, I’m sure your setup is nice, but I’ve been in the game a bit longer. I’ve probably got nicer gear.”

“That’s great. Sounds good.” Wilbur’s nerves kicked up a few more notches. He was going to embarrass himself, he just knew it. He was going to walk in, immediately get hard just looking at your setup (which was already somewhat familiar to him) and look like a loser. He tried to shove that thought away.

Thankfully, it seemed that you sensed his discomfort. “Listen, uh…I know that you’ve only done something like this once,” you said. “If you ever change your mind, you can leave. I won’t judge you for that, even if we’re in the middle of filming. Consent rules don’t magically go away when there are cameras rolling.”

Wilbur’s heart thumped in his chest. You were smiling warmly at him over FaceTime, and he wanted nothing more than to be there with you. His thoughts weren’t sexual, at least not in the moment.

His mind wandered. When was the last time he’d been held by somebody? He’d never once been held by somebody who liked him romantically. He wasn’t sure that anyone outside his family had ever so much as hugged him. The thought made him dizzy. “Thank you,” he managed to say.

“Don’t thank me. It’s basic decency.” You continued smiling at him. “Oh, we don’t have a time set. Does one work?”

“One is fine,” Wilbur replied. “I’m totally cool with one.”

“Sounds good. Saturday at one, then,” you said. “Be ready to film.”

“I’ll be ready,” Wilbur promised. He just hoped that it was a promise he could keep.

He spent the rest of the week panicking. He shoved himself into schoolwork, studying, finishing up the essay that you had distracted him from. On Saturday morning, he woke up, shaved, took a shower, blow-dried his hair and got dressed. He knew that the clothes would be coming off, but he tried to dress somewhat nice anyway. He figured that even his nicest jeans and a button-up would be fine. He kept reminding himself that a business encounter was all this interaction would be.

Around noon, he got a text from you:

Hey ;) ready to film?

He quickly replied.

Born ready. Send your address?

The next message contained your address. He took a deep breath, brushed his teeth (for the third time that day) and set off. He left his apartment, got into his car, and started driving.

He put on a playlist on the way there, one he had made containing music from your favorite bands. He kept constantly checking himself in the mirror to the point where he realized he would hit something if he didn’t stop. He was an absolute wreck of nerves.

He pulled into the apartment parking lot and got out of his car. He walked into the building, took the elevator…

And there was your door. He stepped toward it and hesitantly knocked three times. The wait was agonizing. He stood outside the door for a minute before you opened it.

“Sorry!” you said. “I was in the middle of getting the lighting set up. Come in!”

“No worries.” He followed you inside. Your apartment was immaculately clean, with enough decorations to add character without being overwhelming. He followed you down the short hallway to your bedroom.

Sure enough, it took a lot to keep himself calm the second he stepped through the door. The whole place smelled like you, and it was enough to make him lightheaded. He looked at the setup, and it was honestly impressive. You had a professional-level camera setup, multiple lights, and cameras at various angles. “This is…wow,” he said. “You know your shit.”

“I’m a professional.” You winked at him as you adjusted the angle on one of the cameras. “Okay, so…a bit unconventional, but we’re going to do a test of sorts to make sure that the angles on the cameras are correct. Is that alright?”

Wilbur shrugged. “As you said, you’re the professional. I’ll let you call the shots.” He had no idea what a “test” would entail, but he wasn’t about to question it. He stood off to the side, watching you as you worked. Your white tank top left absolutely nothing to the imagination.

“Great.” You adjusted one of the lights, lowering it slightly. “What do you think? Too bright in here?”

Come to think of it, it was a little blinding. “Maybe a bit softer,” Wilbur suggested.

“Good idea.” You nodded in agreement and dimmed the lights. “Better?”

“Better.” Wilbur took a few deep breaths. “We good to go?”

“Good to go.” You sat on the bed, examining the angles from your sitting point, clearly trying to decide if they were any good. “Yeah, definitely good to go.”

“Okay, then.” Wilbur stood there awkwardly. “What, um, what do I do?”

“Like I said, I want to test the angles before we start actually filming.” Wilbur watched as you pressed record on all the cameras. “I figure we just experiment with a few positions, see how the camera captures it. You can stay dressed if you want—-like I said, this is just a test.”

“Alright,” Wilbur murmured. He sat on the bed and nearly froze when you cupped his cheek. His face was so close to yours that he could barely breathe.

“You still okay with this?” you asked, searching him for any sign of hesitation. He nodded. This was terrifying, but the thought of walking away was even scarier. “Good.” Mere seconds later, you pressed your lips to his.

It took him a second to kiss back, but once he started, he never wanted to stop. Your lips were soft against his, just testing the waters at first. He had no idea where to put his hands, but he didn’t have to think about it for long, as you quickly pushed him onto his back. He made a small noise as you got on top of him and continued kissing him.

Wilbur didn’t consider himself a good kisser. It wasn’t like he had much experience. The kisses became rushed and sloppy, and just as he started to settle into the rhythm, you were getting off of him and checking the camera footage. He sat there, dazed, as you made your way around the edge of the bed, checking what the cameras picked up. You were explaining something about the process, something about lighting and shadow and…whatever else, Wilbur wasn’t listening. He could still taste you, still feel your lips against his.

He only snapped back to reality when you approached the side of the bed again. “You still okay with the pegging thing?” you asked.

“Yes,” he breathed out. He could feel how hard he was, the slight friction against his jeans, but he didn’t have it in him to be embarrassed anymore. Who cared if this was just for work, just for content? He was about to have you, and having you in any capacity was better than not having you at all.

“Alright, then.” He watched as you opened a nearby dresser. “I have a couple things that you can choose from…” You pulled out a box and set it on the edge of the bed. He scooted closer as you opened it, his throat catching at the array of items. “These are all the toys I have that are compatible with the harness,” you explained. “I’d rather us not start filming until the main event, so to speak. We can get you all prepped before that.”

He nodded, breath catching in his throat. “Sounds good,” he choked out. He glanced over the collection of toys. Some of them were definitely too big for him, so he avoided them. His eyes finally landed on a pink dildo, just slightly bigger than the one he’d used in a recent clip. “That one, maybe?” He pointed.

“Good choice,” you said. “Just got this one.” You picked it out of the box and laid it on the bed. Wilbur’s eyes stayed on you as he watched you gather more stuff—-the strap-on harness, some lube, a buttplug. You went about it with the precision of a doctor gathering medical supplies. It was both hot and slightly unnerving.

“Do we have everything?” Wilbur asked. He shifted slightly, both to get comfortable and because it was difficult to sit still when he was so close to you.

“Yep! We’re set.” You sat back down on the bed close to him. He shuddered as you rested your hand on his thigh. “Still okay?”

“Still okay,” Wilbur confirmed. He closed his eyes as you leaned in to kiss him. He kissed you back, less sloppy this time, less desperate. He wanted to be able to contain himself, at least a little. He didn’t know what you’d think of him if he appeared too needy.

Your gentle hands pushed him backward, and he laid down on your soft mattress, eyes unfocused as he looked up at you. He pulled you in for another kiss, and whined as your tongue found his. The sound was pathetic in his mind, but it seemed to spur you on further. He gasped as you grinded against him. Even though it was only the tiniest bit of friction, it was one of the best things he’d ever felt. His hands wandered to your waist, sliding under your tank top. It was the boldest thing Wilbur had done so far, and he was more than pleased when you leaned further into his touch.

A moment later, your lips left his. He frowned for only a split second before realizing why. When he opened his eyes, your hands were brushing against his as you took off your tank top, leaving absolutely nothing underneath.

He stared. He couldn’t help it. He wanted so badly to touch all of it—-your stomach, your bare waist, your chest. It was almost too much. His cheeks went red as he heard you laugh softly. “Enjoying the view?” you teased.

“Oh! Um…sorry,” he said sheepishly. He forced his eyes upward, and when he did, he locked eyes with you. To his surprise, there was no sign of disgust or embarrassment on your face, only amusement. “You’re just gorgeous. Couldn’t help it.”

“Of course I am. How else would I have gotten this job?” You smirked down at him, and he managed to laugh despite his nerves. “In all seriousness,” you said, “thank you. You’re pretty good-looking yourself.”

It was one of the more tame comments he’d gotten in recent times, but it was by far the best. “Thank you,” he replied, his voice coming out as a squeak. Before he could apologize for that, you were kissing him again. Your hands found the buttons of his shirt, and he helped you take it off without hesitation. His mind went blank as your hands wandered his skin, tracing the lines of his abdomen and chest. He returned the favor, letting his hands wander a little. He held back, not squeezing or grasping, just lightly touching.

You slid out of your shorts, and Wilbur fumbled with the button of his jeans. Once he undid that, you got his zipper for him. You lifted yourself up for a moment so that Wilbur could remove his jeans. He shivered as his bare skin met the cool air of your room, then frowned as you got off of him. “We should get you ready,” you said. He nodded, finally removing his boxers.

He let them fall to the side of the bed, leaving him completely exposed. He could feel how hot his cheeks were, but you didn’t seem to be judging him for it. In fact, you were focused instead on putting lube on your fingers, occasionally glancing at Wilbur. He shivered, parted his legs without you asking. He laid there for a moment, staring at your ceiling, trying to calm himself. He only had a moment before you were back, settled down beside him. “You ready?” he heard you ask. He could only nod in response.

He felt a finger press inside of him, and he sighed. His eyes closed, his lips parted, and he let himself revel in the feeling. For once, he had someone else’s fingers, someone else’s touch. Of course, only one finger wasn’t nearly enough, but it was a perfect start. He moaned quietly as you moved your finger in and out, slowly, almost teasingly. He spread his legs further for you, and you scooted closer. At one point, your finger curled just enough that it brushed against his prostate, and the moan that he let out was downright desperate. He clasped his hand over his mouth, only for you to move it away. “Where’s the fun in that?” you murmured. He couldn’t even process your words before you brushed his prostate again, and he nearly moaned even louder.

“More?” he questioned. “Please?”

“Since you asked so nicely…” You slid in another finger and he whined. It was then that a thought occurred to him.

When he used his own fingers or his own toys, he never properly prepped himself. Not ever. It always hurt a little bit, since for him, he was always doing it just for the camera. It made him realize how much he neglected himself when it came to his job, never truly considering his own boundaries or what felt good to him. And yet, here you were, and it didn’t hurt with you at all. Even though this was just for work, just for content, you were being more considerate and gentle with him than he was with himself. He made a mental note to thank you later.

In the meantime, your fingers curled against his prostate, and he let himself moan and whine, gripping at the sheets and breathing heavily. He let his mind go empty, let himself fully relax, let himself be yours even if only for a moment in time. He felt it as you switched between brushing against his prostate and prepping his hole, gently stretching your fingers to spread him a little wider each time. “This feel okay?” you asked.

Wilbur nodded, unable to speak properly. You continued your movements, and Wilbur continued his moans. Your fingers were gone all too soon. Wilbur gasped a few times and forced his hazy vision to focus. “All good?” he asked, a little concerned. He watched as you wiped your hand off with a wet wipe before tossing the wipe in a bedside trash can.

“All good,” you replied. “You feeling ready? I grabbed a plug just in case you wanted to use that for more prep, but if you’re feeling good, I say we go for it.”

“I’m good to just go for it,” Wilbur said. To his surprise, his voice was a lot more steady than it had been. Something about your presence was calming, even in a situation like this that Wilbur had no experience with. He watched as you got the harness ready and strapped it on. Okay, maybe the dildo was a little bigger than he’d originally thought, but he would be fine. He hoped. “Thank you for, um, helping me get ready.”

“Why wouldn’t I help? I don’t want you to be uncomfortable,” you said. You finished putting on the harness before coating the strap in more lube than was probably necessary, just for good measure. “The nice thing about not working for some big porn company is that we get to do things in our own time. We’re not rushing to fit some director’s schedule.”

Wilbur nodded. “Right.” He’d heard varying things about being in professional pornos from various people in the industry. Experiences ranged from incredibly negative to incredibly positive, depending on the company, the director and any number of other factors. Wilbur was grateful to be making enough money on his own to make this venture worth his while. It was nice not having to risk mistreatment. “Still. Thanks.”

“You’re welcome.” He watched as you pressed “record” on each of the cameras. You turned back to him, your expression focused, methodical. “Ready?”

Wilbur nodded. “Ready. Um…safeword?” He definitely didn’t plan on using it, but it was always better to be safe.

“Is the stoplight system good with you?” Wilbur nodded. He’d never used it, but he knew what it was. “Perfect,” you replied. “Let’s get this show on the road, then.” You smirked, and Wilbur grinned back. All the nerves were gone, replaced with excitement and focus. The cameras were rolling. Time to put on a show.

Wilbur wiggled his hips slightly, getting comfortable as well as a bit closer to you. He glanced at one of the cameras and shifted a little so that it would catch his facial expressions better. His eyes quickly went back to you. He felt your hands on his thighs. “You gonna be good for me?” you asked, your voice a little louder than it had been earlier. He figured it was just for the cameras.

“Y-yes,” Wilbur said, slightly exaggerating the tremble in his voice. From the look in your eyes, you approved. “I-I’ll be good for you. I’ll be a good boy, I promise.”

“Yeah?” Your hands ran up and down his thighs, causing him to tremble and shiver. “Then be a good boy, and tell me what you want.”

“I want…I want you to fuck me,” he said. He realized then that he was being too quiet for the cameras to pick up, but thankfully, you saved the scene.

“A little louder, sweetheart. I couldn’t hear you.”

“Fuck me,” Wilbur said, a little louder. “Please.” Despite the fact that it was just an act, he knew that the way you called him sweetheart would be playing on repeat in his head for weeks to come, if not months. His obsession was certainly deep enough for that.

“Good boy.” He felt the tip of the strap press into him, and he gasped. “Aw, already too much?” You asked teasingly.

He shook his head frantically. “No. Not—-not enough. Need more. Please…” He tried to scoot closer to you, to get more, but you shook your head.

“You only get what I give you. Understood?” He nodded. “Good boy.” You continued pressing the strap into him, painfully slow, giving him a chance to adjust to the size of it.

He whined, trying not to arch his back or move too much. Instead, his hands gripped at the sheets. He tilted his head to the side a little bit, right in the view of the camera to show off his face contorted with pleasure. His viewers always liked that; he figured that yours might as well. “Fuck,” he gasped out. “You’re so…so big…”

“Too much for you? Or are you gonna be good and take it?” You pushed the rest of the way in, and despite feeling fuller than he’d ever felt, not an ounce of pain came with it. Wilbur was grateful for that.

“I can be good,” Wilbur promised. “I can take it. I swear I can be good and take it.” He whined as you shifted your hips a little, and his hands went to grasp at your back. “Please. Please start moving. I need—-I need you.” Not even Wilbur could tell at this point where the genuinity ended and the act began.

You grinned. “You’ve been good so far. I feel like you’ve earned a reward.” You started shifting your hips, slow but deep thrusts that had him reeling. You weren’t quite getting his prostate, and he suspected that it was on purpose, you wanting to draw this out longer for the cameras.

Wilbur tilted his head back slightly. His eyes fell half-closed, and he peeked out at you from beneath his lashes. He let his lips remain parted. He suppressed his moans, opting instead for gasps and grunts. It would make better content, he figured, if he could start small and build up to it. It was taking a lot of effort to hold back.

“More?” he asked meekly, trying to make his voice loud enough for the cameras, yet quiet enough to keep up the submissive appearance. Although, he supposed it was more than an appearance. With some time, practice and confidence, maybe he’d be able to play a different role. For now, this is what it was. His body trembled slightly with the nerves and the sensations.

“Hm? What was that?” Your movements slowed down a little, much to Wilbur’s dismay. “Did you just ask something of me without saying please?” You leaned down, your face hovering inches from his. “You remember when I told you that you only get what I give you, right?”

“Y-yes,” Wilbur said. “I’m sorry. I’ll be good.” He sighed as you ruffled his hair, his brown eyes wide and gazing up at you full of desperation. “I promise.”

“Then say please,” you replied. “You can say please, can’t you, baby?”

Wilbur nods, a sharp, jerky movement. “C-can I please have more?” he asks.

“More what?” you asked innocently. Your hips continued rocking back and forth, so languidly that it was frustrating. “What do you want, sweetheart? Use your words.”

“I-I want it harder,” Wilbur replied. “F-faster. Please? Please, I need it.” With every passing moment, Wilbur became less and less aware of the cameras picking up his every move. If he focused hard enough, he could pretend that this wasn’t all an act. It was a dangerous game, pretending that way, but as time passed, he cared less and less.

“I guess I can give you what you want,” you said nonchalantly. “If you promise to be good.” Your movements picked up speed, hips thrusting slightly faster but just as shallowly. You weren’t thrusting all the way to the hilt, but Wilbur did his best to be patient despite wanting it desperately.

“I promise,” he panted out. “Please. I’ll be good.”

“Good boy,” you cooed. Wilbur felt a shiver go down his spine, and his shivers immediately turned to gasps as your thrusts got harder, faster, more forceful. He tried to tilt his hips a little, make you brush against his prostate, but you refused to comply, still avoiding the spot entirely. He let out a whine, high-pitched and needy. It was almost embarrassing, but based on the way you only smirked wider and picked up the pace, it was clear that you weren’t about to judge him for it.

Wilbur let himself get a little louder. He was tempted to cup your face, to run his fingers gently along your sides. He almost did before remembering that this wasn’t real. You didn’t love him. This was just sex. His second time ever, with someone he’d been crushing on obsessively, and none of it was even real. Despite how good he felt physically, he started to feel like shit mentally. The thoughts combined with your movements caused him to tear up a little bit, much to his embarrassment. He felt his eyes burn a little, and he glanced away from your face, trying to hide it.

It was no use. You saw. “Color?” you asked softly, too quiet for the cameras to pick up properly. Your eyes held a somewhat concerned expression. Immediately, Wilbur felt bad for upsetting you.

“Green,” he replied easily. “I’m okay. Promise.” He even managed a small smile.

You nodded, the worry slowly melting from your face. He moaned as your movements picked up speed again, and then whined as you finally, finally, hit his prostate. His moans got increasingly loud as you continued hitting that spot with every thrust of your hips, burying yourself inside of him to the hilt of your strap. He looked down between his legs as best he could, watching you move in and out of him. He could only look for a moment before having to tilt his head back and whine once again.

“Look at you,” you cooed. “So desperate for my cock, huh?”

“Y-yes.” Wilbur gripped the sheets with one hand and your shoulder with the other. “Please, please, please don’t stop.” His voice came out sounding whiny and pathetic, wobbling with every word.

“You’re doing so good,” you replied. “Taking me so well.” Wilbur moaned once more as you gripped his hips, using the hold as leverage to help you thrust harder.

He could feel himself getting close. He noticed how much pre-cum he was leaking, small drops of it dripping down his cock. “S-so close,” he whined. His hand subconsciously went to his length, but you quickly pulled his hand away.

“Not without my permission,” you chided him. He gasped as you continued your movements.

“Please,” he said desperately. “Please, I need…fuck, I need you to touch me. Please.”

You grinned and wrapped a hand around his cock, slowly pumping him up and down. He let out an embarrassingly loud moan. After just a few movements of your hand, his hips were twitching. He let out a series of swears and pleas, his words nearly incoherent as he finished, cum coating your hand and his stomach. You murmured soft words of praise, but he could barely register them.

His vision was hazy as you stopped moving. He gasped for air, panting. He felt numb and overstimulated all at once. His hand that was gripping the sheets slowly loosened its grip, and he let his hand fall from your side. “Thank you,” he murmured. His throat felt scratchy and dry.

“You were such a good boy,” you said, running a hand down his hip to his thigh. You pulled out, and he gasped at the feeling. You leaned in close to him, your faces inches apart. “We’ll have to do this again sometime, yeah?” He nodded eagerly before you pulled away.

He watched as you turned off the cameras, and he finally let himself relax, laying down fully on the bed. His gaze went from you to the ceiling before he closed his eyes. He needed a break, a few moments to collect himself, to come back to reality. His eyes still burned, and he let a few tears escape down his cheeks. How could something so pleasurable also be so painful?

He laid there for a few moments, taking deep breaths and trying to calm himself. He closed his eyes, trying to will the tears away. He couldn’t get over the thought that this wasn’t enough, that he needed more of you, and he needed it to be real. It was as if all his years of loneliness were catching up to him at once. Every night that he wished someone would hold him, every day that he’d spent pining after people who would never love him back…not to mention the constant self-loathing that came from the small amount of self awareness that he had, the awareness that he was a creep who nobody could ever love.

Wilbur heard you as you took off the harness before walking over to his side. “You alright?” you asked. Your voice was soft, concerned. “Was I too rough with you? Do you want some water, or maybe something to eat?”

Wilbur opened his eyes and sat up a bit. “Um…water would be good. And no, you weren’t too rough with me.” He wiped his tears off his cheeks and managed a smile. “You were a lot less rough with me than I am with myself, honestly.”

You grinned back at him. “Okay, I’ll get you some water. If you want to clean yourself up, the bathroom is to the right of the entrance to my room. There are washcloths in the drawer under the sink.”

“Thanks,” he said. Some warm water to help wipe the sweat off him sounded almost magical. “I’ll go do that.” He slowly got off the bed, feeling a little shaky. Your kindness and the sweet sound of your voice had taken away some of his pain, but the loneliness lingered in his mind like an ever-present itch that he couldn’t reach the source of.

“I’ll be here when you get back,” you called after him. He went into the bathroom and closed the door.

He used the bathroom, cleaned himself up, and was about to head back to your room when something caught his eye. You had a laundry hamper in the bathroom, and on top of the pile of laundry, nearly blended in with the surrounding fabric, was a pair of black underwear.

He immediately beat himself up for even thinking about taking it…but god, it was tempting. He would have something of you always, something you’d touched. More than just touched. He could keep it in his room, with his things, a little souvenir.

The only other souvenir he’d ever kept was from the girl he was obsessed with in high school. She had once torn out a page of notes and dropped them in the trash can, and he had fished it out and kept it. Of course, he’d thrown it out after she’d called him out for being a creep.

Never had he had something like this. But he quickly realized that, even if he wanted to, he couldn’t take it. He was naked, so it wasn’t like there was a pocket to hide it in.

He pushed away the disappointment and left the bathroom. It was better this way, better that he not have the opportunity to do what he wanted. Despite knowing that it was for the best, he couldn’t help but feel upset by it.

He re-entered your room, where you were sitting on the bed. You’d changed out the duvet, and there was a glass of water on the nightstand for him. You were dressed again in sweatpants and a t-shirt, and he felt more exposed than ever. You turned when you heard him enter, and immediately, he was given a smile. “Feeling better?”

Wilbur nodded and smiled back. “Much better, thanks.” He glanced around and saw his clothing on the floor. “I’m just gonna…”

Your eyes flitted to the pile of his clothes. “Right. Good idea.” You then glanced at the dresser in the corner of your room. “Hold on, I have something you can wear instead of that uncomfortable button-up you were wearing.”

Wilbur was about to protest and say that the button-up was fine (despite the fact that it was cheap and a little itchy in reality), but he quickly shut his mouth and worked on getting his jeans and boxers on. If you had something for him to wear, something that was yours, that would be a dream come true. He watched you as you shuffled through a drawer.

“Here it is,” you murmured, more to yourself than to him. He saw as you picked up a t-shirt, one that was definitely too big for you. “I have this extra shirt. I accidentally ordered a few sizes too big, so you can have it if you want.” You tossed it over to Wilbur, and he caught it.

It was a band t-shirt. Wilbur recognized the band as one of your favorites. “Are you sure?” he asked. The material was soft in his hands, and Wilbur swore that it smelled like you.

“Yeah, I’m never going to wear it. It’s yours.”

Wilbur held it like it was precious. He examined it before sliding it on. It fit him well, not too loose but not too tight. He looked over at you and immediately noticed that you were looking right back at him. “It fits really well,” Wilbur said. “Thank you. This is much better than my other shirt.”

“No kidding,” you replied. “That thing felt like it was awful to wear.” You paused. “Plus, you look good in it.”

Wilbur could hardly believe it. You had complimented his appearance twice. In one day. “Thanks,” he said, his voice slightly shaky. “I, um, appreciate it.” He reached for the glass of water on the bedside table and sat down in order to steady himself. He took a sip, immediately feeling refreshed. He hadn’t realized how dry his throat felt.

“Anytime.” You sat beside him on the bed. “Can I…ask you something serious?”

Wilbur put down the glass and turned his full attention to you. He saw the slight concern in your expression, and his small smile quickly faded. “Sure. What’s up?”

You tilted your head slightly as you looked at him. “Are you okay? I know that you said you were alright, but you seem a little shaken up still. I’m just a bit worried.”

He sighed, trying to figure out what to say. On the one hand, he could be honest. At least, a little bit honest. You didn’t need to know the full truth. On the other hand, he could insist that he was fine. He worked through the options in his mind, and settled on a half-truth.

“I, uh, have never been pegged before,” he said. “This was my first time. I think I just got a little overwhelmed is all.” He paused, and when he saw your expression grow more concerned, quickly added, “But I’m fine! Really, you were great. You didn’t do anything wrong, and it was a good first time. A great first time.” He could feel his cheeks get slightly hot, but he did his best to stay relaxed.

You looked surprised, your eyes slightly wide. “You…you got pegged for the first time, just now, on camera?” You shook your head, a barely noticeable movement. “That’s…brave. I’ve never done something for the first time on camera.”

“Yeah…yeah, I probably should’ve prepared beforehand,” Wilbur said. “But I just figured…it’s not like I’ve never done anything anal on my own. I figured it would be fine, and it was.”

“But you looked upset,” you said.

“Just overwhelmed,” Wilbur replied. “I promise it’s okay.” The last thing he wanted to do was deter you by making you feel bad. Besides, it really wasn’t your fault.

“Wilbur…” You looked away, pausing as if considering what to say. “Allison showed me a short clip the other day of that video you two filmed, and…and I don’t know if it was just an act, but I got the feeling that you were very new to what you were doing.” You looked back at him, and he felt the intense desire to disappear, to change the subject, because how could he admit how little experience he had without being intensely embarrassed? “Was that…did you ever have sex before that?”

Once again, Wilbur had the choice between honesty or a lie. Somewhere in his mind, he knew that he wanted to try for more with you—more than just friendship, and definitely more than business partners. The terrifying thing was this: if he wanted that, truly wanted that, then he would have to be honest with you at some point.

“...No,” Wilbur said, barely audible. He avoided eye contact. “I was, um, too nervous to tell her that it was my first time. I wanted to do a collab, so I just didn’t say anything.” He fidgeted with his fingers, trying to distract himself. “I…maybe I was wrong to do that. I don’t know. I wasn’t trying to hurt anyone, I just didn’t want to wait around for things to happen for real, because I need the money now, not later, and…and it didn’t seem like anything was going to happen anytime soon, so…” He shrugged, hoping that the explanation was enough.

“And…and was it good?” you asked. “Like, was it a good first time for you? Did you enjoy it?”

Wilbur thought back to it. Allison was nice, sure. She was amenable, very understanding when it came to the fact that Wilbur was new in the industry. And yeah, Wilbur had finished that first time with her, but when he really thought about it, he couldn’t say it was enjoyable. It wasn’t enjoyable, being with somebody he had no connection with. It wasn’t enjoyable knowing that this incredibly vulnerable moment of his life was being livestreamed in real time, and it definitely wasn’t enjoyable that his first time was done for profit rather than for the experience, for the fun.

“I mean, does anyone enjoy their first times?” Wilbur managed to dodge the question, but his eyes still didn’t meet yours.

“Yeah! Well…I don’t know. They’re generally not good in the sense of being physically pleasurable, but they don’t have to be awful,” you said. “I just…I can’t imagine doing that in front of a camera, streamed live like that. And it sounds to me like you did it because you didn’t feel like you had any other choice.”

Wilbur finally looked up at you, scared of a reprimand, scared of your judgment. But all he saw in your expression was worry and kindness. “I…I’ve just never really had the opportunity,” he said quietly. “I’ve never been in a proper relationship. I kissed a girl, like, once in high school, but that was it. And then not again until Allison. I just wanted to get it over with, to feel…I don’t know. Normal, I guess. Desirable. Like…like someone wanted me.”

The second the words came out, Wilbur was mortified. He’d never told anyone any of this, and the fact that he’d told you of all people, the second time he’d ever spoken to you in person, made him wish he could turn back time and erase this entire conversation.

He felt you gently take his hand. “I’m sorry,” you said, “that things didn’t turn out the way you would have liked.”

Wilbur looked down at his hand, gently wrapped in yours, and he gave it a small squeeze. “It’s okay,” he said. “It wasn’t awful.”

“Still,” you said. “It sucks.”

“It does suck.” He watched as you let go of his hand, hiding his disappointment. “Anyway, um…I’m sorry to unload all that on you,” he said, his self awareness returning to him.

“It’s fine, Wil. We’re friends, and I wouldn't have said what I said if I wasn’t prepared for a response,” you said. “Really, it’s okay.”

He could hear the softness in your voice, the hint of concern. It nearly made him cry again, just knowing that somebody cared about him at all. “Thank you,” he said. “I…I really appreciate it.” The words felt so tame in comparison to what he wanted to say, but all the words he could think of seemed too much. He couldn’t believe that you’d referred to him as a friend, that you wanted to continue associating with him. It seemed too good to be true.

One thing was certain: it would take a lot of willpower to make this obsession go away, and Wilbur wasn’t sure he had it in him to let you go.

To Wilbur’s absolute delight, his time with you didn’t end there. After filming, he stayed for dinner. He ate pizza with you on your couch, watching a cheesy 80s movie and making fun of the special effects. Admittedly, he watched you far more than he watched the film, and he felt shivers every time you looked his way.

Over the course of the next week, he messaged you every day. Sometimes, it was because he messaged first, and other times, you were the one to reach out. He forced himself to exercise some restraint, to not be too eager. You made it difficult. Many of the texts were about the video, you giving Wilbur updates on the editing progress. At the end of the week, it went live. Wilbur was notified by your message:

Done! Let’s see how this goes

Wilbur grinned, swallowing back all the anxiety that he felt. What if it was bad? What if people didn’t like it? What if his inexperience showed on camera?

He shoved it all down and sent a reply.

Sweet

After a moment, he was struck both by how boring his last message was and how great of an opportunity this presented him with.

Want to celebrate tonight? Drinks on me?

He waited anxiously for a reply. Five, ten, fifteen minutes passed with no response, until finally, your name appeared on his screen.

How about that bar a block from my place? You know the one?

Wilbur did, in fact, know the one. He’d passed it on the drive to your apartment.

I know it. Send the address and I’ll be there

Eight?

He smiled.

Eight sounds perfect :)

Once again, he couldn’t believe his luck. He took a shower, brushed his teeth, combed his hair. He left early to make sure that he was there in time and that you wouldn’t be stuck waiting for him. The cab ride to the bar felt like it took a million years, and when he got there, you were sitting at the bar waiting for him.

The bar was packed. There was music blasting over the speakers, some pop song that Wilbur couldn’t place, though he’d heard it over the radio a million times. He sat beside you at the bar. “Hey!” he said, perhaps a little too enthusiastically.

You greeted him with equal enthusiasm. “You made it!”

“Of course I made it,” he said, grinning. He could already feel his cheeks get warm, although whether it was from the crowded bar or his proximity to you, he couldn’t tell. “I hope you weren’t waiting long.”

“Only about five minutes,” you replied. “But I got here early. Still waiting for the bartender.”

“Perfect.” Wilbur glanced at his surroundings. The scene reminded him of when he’d first met you. It was hard to believe that it had been less than a month. “Is the video doing well?” It was too early to draw many conclusions, of course, but he was curious.

“Holy shit, you have no idea,” you said, grinning. “People love the video. Already, I’m getting messages asking for more of it.” You seemed proud of yourself, and Wilbur couldn’t blame you. You’d done most of the work, after all.

He could feel his heart pounding. People loved it, which meant that you would probably want to do it again. More time spent with you, more excuses to see you…it all sounded perfect. “So when is part two?” Wilbur asks. “If people love it, I mean…we should probably get to filming more material, right?”

Your smile faltered, and his heart immediately sank. Of course. Of course it was all too good to be true, too perfect to be real. He should have known better. When you finally spoke, Wilbur was already bracing himself for rejection. “I don’t think it’s a good idea,” you said. Before Wilbur could say anything, you continued. “Not because I don’t like you, okay? I…I won’t lie, it was fun. I’m just…”

“You can be honest,” Wilbur said, so quietly that he could barely be heard over the sounds of chatter and music. “If you don’t like me and don’t want to do it again, that’s okay. I get it.” He knew that he sounded pathetic and self-deprecating, but he had no clue what else to say.

“Wil, I just said that it wasn’t because I don’t like you,” you said. “Please take my word for it.” Wilbur nodded, slightly embarrassed. “The reason I don’t want to film more is because I’m a little worried about you.”

Oh. In a way, that was a relief to hear. It meant that you didn’t dislike him. On the other hand, he was terrified. Did you see him as pathetic? He wouldn’t blame you, but it was still a blow to his ego. “...Why?” he finally asked.

“I just…” You sighed. “You were literally crying, Wil. It was concerning. And I’m not saying that you did anything wrong, because you didn’t, I just think that…” You laughed, a short, nervous sound. “Fuck, I don’t know how to phrase this without sounding insensitive.”

Wilbur froze. You were going to call him a creep, pathetic, a loser. He just knew it. “Just say it,” he said, his voice trembling.

“You have some things to sort out,” you said finally. “This type of job can ruin you if you don’t have the self-esteem to handle it. I’ve seen it before. People go into it feeling like shit about themselves, and then all the validation they get is purely sexual, and it fucks with them when they don’t get that validation anymore. It can be hard to separate your sense of self from your sex appeal, you know? But you have to.”

Wilbur took a deep breath. That was somehow worse than anything he’d anticipated you saying. He wasn’t a creep in your eyes, maybe, but he was broken. He had low self-esteem. You saw him as something to be pitied, and that was a hard pill to swallow. He kept opening his mouth to speak, only to close it again. He finally gave up. “Okay,” he said finally. “Yeah. That’s fine.”

You went quiet. It was only until the bartender showed up that you spoke again, ordering some drink that Wilbur couldn’t make out the name of due to being lost in his own thoughts. When you asked him what he wanted, he replied with water. He didn’t feel like drinking anymore.

After the bartender left, Wilbur felt your eyes on him. “Yeah?” he questioned. “What?”

“Did you actually listen to what I said?”

“What? Yeah, of course I did.”

“Wilbur…”

“I get it,” Wilbur said quickly. “I know that I’m…that I’ve based my whole life around this, and I know that it’s concerning, and I get it. But what else am I supposed to do?”

“Take a break,” you suggested.

“I need the money.”

“Okay, well, go back to solo content for a bit. Because I think you need a moment to think things through.”

It didn’t sound so bad, actually, going back to doing things alone for a while. As long as he still had you in some capacity, maybe it would turn out okay. “Alright,” he said. “I could do that.”

“Good.” You thanked the bartender as he handed you your drink before turning back to Wilbur. “I think it would be good for you.”

“Probably,” he admitted. He sipped his water, trying to enjoy your presence despite the war of emotions he had going on. It took him a moment for him to ask the question that he wanted to ask. “...Do you think there’s something wrong with me?”

“No,” you replied immediately. “I just think you need some time off.”

He accepted the answer, but there was one more thing he needed to ask. “I’m sorry if this is…weird,” he said carefully. “But I was wondering if you wanted to go on a date sometime. Like, a proper date, not…”

“An amateur porn filming session?”

“Right. That.” Wilbur felt his hands trembling. “Um…we could go out to dinner sometime. Wherever you want.” He felt dizzy, his breathing shallow and his heart pounding way too fast. “If you want to.”

You took an agonizingly slow sip of your drink. “I’d like that,” you said finally. You smiled at him, and it was like everything falling into place. Wilbur could breathe. You hadn’t rejected him.

And soon enough, he would have you, one way or another.

#wilbur soot x reader #wilbur soot x you #wilbur x reader #wilbur soot smut #wilbur soot x reader smut #simpbur #saccharine writes

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