Chapter Text
Wilbur sighed, popping his knuckles against his fingers. Streaming had gotten rough. Twitch had tightened their pockets severely, but at least they’d loosened the rules a little. Mostly just to profit more over people being horny for girls, completely edging out most male streamers without a good dedicated following. Even Wilbur and other minecraft streamers had been affected, and so came the conceit of this stream. He rolled his shoulders and clicked Launch Stream. Letting it load, and people come in while he went to get some water. Returning, and drinking some, setting it on his desk, he switched it from starting soon, to his face, curly brown hair as always messily unkempt.
“Hey there! So yeah Twitch has gone down the shitter but, you know, can’t exactly fill a resume with Minecraft Streamer.” he shrugs “So, I’ll be doing a subathon, mixed with the interactivity of that Jerma guy.” he gestured below him, where on stream the title read out, “You Vote I Do.” “The way this will work is, people can pay to make suggestions, of things I should do, or questions I should answer. The three highest paid ones every 5 minutes will be picked out, and you can vote on which one for me to answer/do. If yours is not picked, it will roll over, so you can pay more for it to show up, or you can pay to submit a different one.” he explains. “And, the price of subs will be able to be put towards a request. Now, are we ready to begin?”
As chat gave a small chorus of affirmatives he began to run the script, this first one quickly up. The question that won out was, “How are you with the way twitch is going down the shitter?”
“Well, not great?” he raised a brow, playing it off with a brow, “Really wouldn’t be doing a stream like this if I was you know? I do like entertaining you all and having fun but, well, this is pretty desperate.” he lounged back, wringing his fingers. “But, best not to dwell on that! We’re meant to have fun here!” He says
The next request ran up the pipe, “Why don’t you play something you’ve been working on for us?”
Wilbur nodded eagerly, that was something he could do. He grabbed his guitar and began to play, watching as chat cheered him on, slowly filling up, some more subs dropping in and adding suggestions. He smiled as he sang and plucked out the notes. It was nice to know he still had people supporting him. More requests came, simple things, but then an alert came, Someone named Simper4Soot dropping a hundred gift subs, and rocketing their request to the top. “Since twitch has loosened stuff, why don’t you tell us, are you loose back there?”
Wilbur blushed, “Really mates? Fine fine, yeah? I’m not gay or anything, haven’t messed around back there, uh.” He shrugged trying to move on, “Any song requests?” He chuckled, and began to play again to move on. But it seemed that message had lit a spark under the chat, and they began to coordinate. While Will looked away, the next three requests came up, and with massive effort, chat tied all three. When the time was up, he looked up to see which had won and found himself faced with essentially the three same ones.
“Can you take off your shirt/pants/underwear,” was scrawled out in white on his monitor. Each having 33.33% of the vote. Will looked mortified, just staring for a long while. He frantically reached over to expand the vote and sighed, shirt having that extra hundredth of a percent. “Sorry but, no ties can happen, which is why I picked three as a number.” He said, sighing with relief. He picked up his guitar to take off the strap, and set it aside, hoping that warning would tone down chat. Once that was done, his long fingers got to work. He gingerly undid the buttons, inch by inch showing more pale skin. He had some curls of chest hair in the middle, going down to his stomach, but surprisingly no treasure trail. He shrugged the shirt off, curly- haired arms resting back onto his chair. “There, how’s that?” he raised a brow, looking to chat.
He could almost feel their eyes on him, and he swallowed thickly, hand crossing his chest to hide his nipples, as if that would do anything. Well it did, chat noticing and laughing at the embarrassment. That only made the streamer all the more bashful, but before he could say anything more the next poll came up. Pants and underwear still on there, along with showing off his hole. Quickly, chat decided to go in order, and pants won. Wilbur put his head in his hands, thinking. Should he just call this off? But, no they’d already paid for it it would be bad to just go back on it and betray his community. So he pulled on a smile and stood. Undoing his belt buckle, and then the button holding up his trousers. Pulling down his pants. The first thing revealed was his bulge, in black briefs, and then thin hairy legs. The clothing bunched around his feet, and he bent down to pull it away, unintentionally giving the camera a great shot of his pert ass. Chat was going wild, and as he straightened up, folding the clothing to put away, he realized what he had done. Will hastily sat down, to stop showing it off, hoping to blend the black fabric in with the dark chair. “Alright alright chat let’s do something more wholesome.”
His viewers, of course, interpreted that a different way. The next request was quickly pushed up and voted through. “Holesomely take off your underwear and show us your hole.” The white letters said, glowing as if carved into the monitor, Will’s heart hammering. At least for this he could face away from the screen. He stood up and turned. Fingers catching the hem, pausing there. He screwed his eyes shut and pulled them down, bending over. The whole stream could see his tight, hairy ass and that small, unused pink hole hidden between the cheeks. Wilbur’s cock and balls were hanging between his legs, soft and tight as well. He felt humiliation building up in his core. He turned around, “Alright I think this was a bad idea, let’s just.”
There was a donation. Two hundred dollars from Simper4Soot. “Finger yourself. If you do it, you’ll get 1000 dollars. Double if you stick two in and scissor.”
Wilbur distracted himself, not answering yet. His fingers typed into his phone to find out what scissoring meant anally. Eyes glancing over diagrams, and porn in equal measure. 2000 dollars, for just two fingers. That would handle a good chunk of his expenses. He nodded, caught himself, and then, dug his nails into the palm of his hand. He had to do this.
“Alright, I’ll do it just, let me get set up.” Wilbur moved the camera to the bed, and laid down, almost happy to just, press his face into the sheets and hide it. His fingers reached around behind him, and slowly, felt they way in. Nearly trimmed nails running over the pink rim before a single one pushed it’s way in. Wilbur bit the wite fabric, as he ever so slowly forced the digit deeper. The stream seeing his hole clench and throb around the intruding finger. He worked it deeper and deeper, until his hole was flush with the hand. It felt, weird. Having part of him inside himself, feeling his own guts, muscular rectal ring squeezing. His dick, trapped under him, gave a little start as he accidentally rubbed it against the sheets, adjusting to bring his hand closer, to work in a second finger. He closed his eyes, bracing himself and sucking in a breath. Then, his fingers separated, and his legs went weak, splaying. Pleasure, shooting like a bullet though him. Eyes going immediately wide, pupils dilating, and a muffled “mmmgh” of ecstasy escaping his mouth. He immediately pulled them out, not wanting to even think about what that meant for him. He just grabbed the camera, scurried up and back to his computer, and said, “Alright! Did that! Scissored, whatever, good?” he asked almost pleadingly.
Then the donation came in. Two thousand dollars, directly to him. He went to check that it was deposited, once again not wanting to face himself and how he was doing anything for the money the chat was bringing him. Surely, that had to be the end of it. But already the next poll was up, Wilbur forgetting to stop it for the donation, and the votes were climbing. Chat was wanting him to fuck himself on something. Donations piling up, pushing for it. All Will needed to do was debase himself further. As the vote closed, it was settled.
“Guys I don't have any dildos or anything to do that with, so I don’t think I can…” He warned.
Their response was simple, and showed how much they wanted this, “Just use something random then, whatever you have around.”
Wilbur looked around for anything that would work. His eyes fell on the half empty water bottle on his desk. It was tapered, so it’d be fine right? He knew fisting was a thing from one or two of Tubbo’s jokes, so surely a tapered water bottle was alright. “Alright uh, let me go, fill this up with warm water, don’t really want cold in me, but then yes.” He rose up, cheekily flashing his ass to chat to keep them donating. He really was desperate…but they had paid for it. He walked out with the bottle, emptying it in the sink, and slowly watching it fill up. It gave him time to think. Would he really do this, go through with, taking his own anal virginity. Well, more of it? He didn’t really know how it worked too well but, fingering himself kinda felt like it was part of that. At least it would have prepped him. He couldn't also bear disappointing his fans, either emotionally, or financially. He swallowed thickly, and took that warm water bottle back. Smile plastered back on, as his digits slid across the container.
Chat was eager to see him back, viewership increasing twofold. His eyes widened, and he knew the pressure was on. “Ah well you uh, did donate for this so, let’s do it!” He ventured over to the computer, to pause the request process, feeling like this would take much more than just five minutes. It was also to bring the camera back over to his bed. He settled it, fiddling a bit nervously, forestalling but then it was time. He got onto the bed, choosing how he'd do it. Facing the camera would be best, and he was decently flexible with his lanky body. His hairy ass faced the camera, his legs held up, ankles near his ears, as he stared into the black lense with that little red dot constantly reminding him of what he was doing. Showing off for so many. His fingers led back down, tracing over that chest, over the red nipples, and down to the hips. Then further, around his cock, and spreading his cheeks wide, presenting his hole. He began to work himself open again, biting his lip as his face burned. If he was going to do this he needed to make sure it was the best, no one unsatisfied.
He took the bottle, pressing the cap against his hole, and then, pushed in. It was smaller than both his fingers, but his breath caught in his throat at the solidity. Unlike his squirming digits, it was unbendable, and filling. He had to hold it there for a moment, hole winking around the green cap before pushing onward. The pink muscle spread obscenely around the slowly thickening neck of the plastic intruder. His hips rolled as it sank deeper, the clear plastic and liquid inside giving an extremely lewd inside look. Anal cavity wide as a pained whimper escaped Wilbur’s throat. It had hurt, more then he was expecting, but, he had to handle it. So much was on the line and, the way it rubbed inside his inner walls. Small curls of pleasure dulling the pain. He just had to adapt. Halfway down the bottle he paused, chest rising and falling, head thrown back. The makeshift dildo had hit something inside him that had sent a mind-breaking wave of pure sensation up through him.
Instinctually, he began to work. Pulling it out then ramming it back in, working his poor pink hole over the bottle again and again, chasing the pleasure. Toes curling, biting his lips, more exhaustive cries of enjoyment flooding out of him. His cock hardened between his legs throbbing. And chat was loving it. The desperate streamer now fully lost in masturbatory motion. Slamming the false shaft in and out in a truly sexy sight. The flat bottle head pounded the prostate until he hilted the whole thing inside him, only the flared feet of the bottle out. His stomach bulged out lightly with it, and then, he released it. The noticeable protrusion being painted white, and pleasured noises pouring out, his brain not even able to form words at this point. His legs and arms fall limp, as hit after hit of pleasure rubs against his brain.
Wilbur panted, wrecked. Eyes fluttering and breath labored. Sitting like that for a while, before eventually returning to consciousness. He slowly pulled the water bottle out of his ass, the pink rim, which, less than an hour ago was tight and virginal now just felt empty. Not even closing fully, gaped. The cum had settled on him, as he had recovered from that orgasm. He picked himself up, brushed his hair out of his eyes, and moved back to his computer. Something in his demeanor shifted, melding together that pleasure high, and performing such pornagraphic acts. Faltering fingers, only from orgasmic weakness typed out, “Wilbur Soot, Gay 4 Pay.” and he smiled to the camera, slightly dopey. Riding the high of his pleasure, he said “So…what do you all want next?”