Monday Evening, 9:36 PM

"So, I'm sure you guys have all been waiting for this, I mean, I'm sure my personal life can't be that interesting. I'm gonna go ahead and set a goal, can't wait to get this fucking started!" Kendall said, pumping an arm up in the air. As the guy began typing away at his computer, James could only sit in excitement. He was anxious to see just how dirty this guy could get, and when a little sound when off, he practically got whiplash from turning his head up so fast.

"Tip Goal Created! At 125 tokens, I take off my shorts! Flash every 50 tokens :)"

A very reasonable goal, James thought. It was a good starting point, and the price was very reasonable, too. 125 tokens was equivalent to about $12.50, an extremely cheap price compared to what other guys would charge for lesser things.

"There you guys go, let's get this show on the road! Have fun, now, don't get too excited, haha. In the meantime, let me put on some music and we can keep on chatting." Kendall said, currently scrolling through his phone, looking for something catchy to play. He decided to put on some of that indie shit James had never heard of before, but it did sound cool. The blonde continued to look through his phone, typing away at something before his head popped up at the alert.

"20 tokens! Woah, thank you so much… CoolGuy92!" Kendall said, pausing a bit to read who it was that had sent him the tip. "Man, I wasn't expecting to be getting tokens this soon. Thanks again! 30 more tokens left for a flash!"

James way beyond anxious to see what Kendall was packing. He never really felt himself get this way before, he would usually just kick back and watch as whatever guy was performing would speed through the goals. Kendall, however, had him on the edge of his seat. No doubt was he the absolute hottest guy to grace this website.

They various guys all went back to chatting, Kendall making small talk and answering whatever questions came him way. Some annoying user, named "HelmetHottie" or something, came in and repeatedly asked Kendall to do weird shit, like feet play and other stuff like that. Kendall was very nice about it, politely declining. But the user eventually got banned from the chat room after spamming his requests without any sort of tipping.

Things went back to normal, the pace a bit too slow for James's taste, until Kendall got another tip.

"Oh hey, 30 tokens! Thank you so much "MichiganMike", glad to see one of my regulars back. Can't wait to see what's new with you. But yeah, I think you guys would all like a flash now, huh? Or maybe not, I mean, I don't really have to…" Kendall said, giggling at all of the incoming messages begging him to show something, how they couldn't wait to see that "nice dick of his". "Haha, okay guys, you know I'm not that much of a tease."

Standing up, the blonde adjusted his webcam camera in order to give a better view of his full body. Biting his lips as he tried to stifle back a smile, his dimples giving it away, he hooked his thumbs into the waistband of his cargo shorts. Slowly dragging the material down as he made the "unst unst" sound, his hips gyrating in a figure 8, the shorts only got lower, and lower, and lower. They slightly pulled down on his underwear, giving the viewers a peek at his happy trail that leaded down to his pubic hair. With his shorts around his ankles, he leaned over on the desk, his face in front of the camera.

"Get ready guys, this is gonna be reaaal hot." Kendall said, smiling as he backed up to his original position. As he pulled down the briefs, his movements painfully slow and making James practically moan out in lust, the base of his cock became easily visible. Not even seconds later, his whole dick was in view, springing up as the briefs now reached the middle of his thighs. Taking it in his hand, Kendall began to pump it, the semi-erect shaft quickly growing harder.

"Oh shit, that feels so good. You guys like it? I bet you all do, you probably want all of it, huh?" Kendall said, his hand massaging his package, fingers wrapped around it and moving in circles, eliciting a moan from the blonde.

James was completely hard. Palming himself through his silk pajama shorts, he was finding the show to be the most erotic thing he had ever seen. Typing up a quick response, a bit hard to write one-handed, James rapidly hit the enter key, wanting to see more and more as soon as he could.

"oh shit, love how big that cock of yours is. fucking love your body and everything about it oh god" James typed, letting his kinky side get the better of him. Was his sentence completely coherent? Probably not. But it sounded hot as shit.

Kendall, on the other hand, was just eating it up. "Oh yeah, you like it DiamondBoi? Bet you wanna grasp it in your hands, huh? Feel how hard I am as you rail me, right, daddy?" Kendall moaned, slowly stroking his cock until he began to smirk, pulling up his underwear slowly and teasingly. "Maybe we can get to that later." Kendall said, slightly turning to the camera, revealing that his briefs did not in fact have a backside, giving a perfect side view of his supple ass.

Fuuuuck, James thought, a jockstrap? This guy was killing him. As he began to type out another message about how much he was loving this, an alert suddenly went off.

"MichiganMike, hook it up! Thanks for the hundred man, that puts us way over our tip goal. Looks like I'm gonna have to ditch these shorts now, but first, I gotta create a new tip goal that I'm sure you're all gonna enjoy!" Kendall said, his grin wide as he was once again typing away at his keyboard. "As much as I love your contribution, Mikey, let's try and get some new tippers tonight! I know all of you want to see more of this."

"This bitch…", James thought as he watched the smug bravado of that Milwaukee whatever user, currently gloating about being the highest tipper. Two can play at that game.

"Tip Goal Created! Jack off at 200! Let's see fast we can do this! ^_^"

Shit, this was exactly what James needed. As he made his way to the "Purchase Tokens" page, he sped completely through it. Selecting the highest package available, not even paying attention to the price, he quickly entered in his debit card info, messing up the first few times as he rapidly entered in the information. Finished, he was met with yet another congratulations message, stating that his account had been awarded the selected amount, and that the transaction would be processed shortly. Perfect.

"Beerdad824! Thanks for the tip dude, that's 50 tokens down! And another 50 from Mike! Holy shit guys, it's only been like 5 minutes and we're already halfways through. Nice to see the regulars back, what's up? Must wanna see me naked pretty bad, huh?" Kendall said, chuckling as he and the two regular users had a bit of back and forth banter, must to James's dismay.

Seeing that he had 2000 tokens to spend, he decided to just finish up the goal. Sending a tip of 100 tokens, showing no doubt as the computer asked to confirm his contribution, he leaned back in his chair, smiling smugly as the alert went off.

"100 tokens… from DiamondBoi! Thanks so much man, a first timer and you're already making a pretty good name for yourself. I definitely hope you become a repeat visitor, I'd love to get to know you a bit more. But now, I guess it's time for me to jack off a bit, huh?" Kendall responded, his voice getting huskier as the sentence progressed. "Gonna get rock hard, show my cock for all of you, and I'm not gonna hold back. Gonna be awesome, guys…"

Leaning back in his desk chair, the blonde lifted up his legs, pulling off the colorful jockstrap in one swift motion. It happened quick, so James's didn't get too good of a look at the blonde, but he did manage to catch a peek at Kendall's ass, causing the tanned male to stifle a groan. He continued the palm his dick through the material, the heat from the close by laptop feeling good against his covered flesh. He would have started fondling himself, his precum leaking as he watched the blonde in front of him completely let loose of any inhibitions. But he would control himself, making sure to wait until the show got really good.

Once the webcam position was readjusted, the blonde leaned back, his dick in his hand as he bit his lip.

"Oh shit, I couldn't wait for this goal. Fuck it feels so good, feels like I'm gonna blow my load all over myself faster than I'd like, heh. Don't worry though, I have so much more planned for tonight…"

And he did, with James nearly busting a blood vessel when the new tip goal popped up.

"Tip Goal Created! At 200 tokens it's time for some assplay! ;)"

The blonde continued to stroke himself, his thumb rubbing against the head of his dick, his other hand playing a bit with his balls. Closing his eyes, humming, he looked like he was in complete pleasure. He must have been a good seven inches, James thought, a good size for when you want to get the job done. He wasn't too thick, his advantage more in length than anything, and James was certain that he had the best dick he had ever laid eyes upon.

The scene continued on for the next 15 minutes, a couple of 5 token tips here and there, along with a few considerable gifts from the two regular users.

"Yeah, is this good, guys? Fuck, I hope you all love it. Can't stop thinking about filling my ass up, any one wanna do it to me? Wanna feel my length in the palm of your hand as you go to town on me, stretching me out and making me scream your name, huh daddy?"

Kendall was just naming off a an extremely detailed list of sexual things he wanted done to him, his eyes closed the entire time, probably not even realizing what exactly he was saying. As wild as it was, James thought it was so fucking hot, his dick practically burning a hole in his pajamas as the blonde just continued with the crazy dirty talk. Biting his lip, James couldn't hold it anymore. Entering in another 100 token tip, he knew he had to get to the good stuff as soon as possible before his cock just completely exploded.

The blonde perked up at the alert sound, his eyes dilated, his body sweaty, and he let out another huge grin. "Diamond! Holy shit dude, 100 tokens again? I definitely hope you become a regular, I love you!" Kendall said, jokingly blowing a kiss at the computer screen. "Damn, I'm pretty sure this may be one of the fastest shows I've ever done, you guys must really wanna see my push my limits, huh? Well, you demand and I'll supply, baby."

Setting another tip goal, the blonde bit his lip as he did a sexy little jig, completely off rhythm to the background music, but James didn't mind at all. James sent another flirty smiley to Kendall, the guy playfully growling at the message.

"Tip Goal Created! Watch me play with my ass, cumshow at 250 tokens!"

Turning his back to the camera, he turned to look over his shoulder, giving a sexy little smirk. As he pulled down the jock strap down over his ass, his cheeks clenching as he shimmied out of the garment around his ankles, he let off a rough smack to his ass, causing James's cock to throb. Kendall then picked up his laptop, bringing it over the bed in the background, setting himself down on the blue comforter with his laptop directly in front of him.

"Ass play time, god it's gonna be so hot, I hope you all love it!" Kendall moaned, positioning the pillows behind him in order to give support to his lower back. Taking a few minutes to get everything settled, fixing the wires around him and adjusting the camera position, he smiled big, panting from the exertion of having to move all around for the past few moments.

Lifting his legs up a bit, he stopped once his knees were pressed to his chest. "Oh yeah, I forgot to mention. I had a little surprise going on the entire show, surprised nobody noticed it. Hopefully you all don't have heart attacks or something, haha." The blonde beamed. Lifting his legs a little bit higher, spreading them out in order to give a better view of his ass, James nearly did have a heart attack at this moment.

Apparently Kendall had had a decent sized blue butt plug in his ass for the past hour and a half. James drew in a sharp intake of breath, ripping off his shorts and taking his cock in his hand. This was so fucking hot, so fucking dirty, and James was practically in love.

With his legs in the air, Kendall began to rub circles around his hole, the close view practically causing every viewer to bust a nut at that exact moment. Kendall moaned out as his massaged his ass, his fingers gripping the end of the toy as he slowly pulled it out, his hole clenching against the rubber object. It had done a pretty good job in stretching him out, with the blonde cupping each cheek as he spread himself, James jacking himself off at what seemed like an impossible speed.

"You guys like it? Wanna see me finger myself, moaning how much I want my daddy to make me cum. Then I'm just gonna shoot my load all over myself, see how good it is. Fuck I'm so horny, wanna be your fucking whore, ngh…" Kendall moaned out, sending chills down James's spine.

He was true to his word. Having already been loosened up a bit by the previous toy, Kendall began to thrust two fingers in and out of his hairy ass. Moaning as his hole contracted from the sensation, his two digits quickly scissoring and massaging his inner walls, James could just imagine himself doing it to the blonde, completely working over his ass, getting him prepped for all of James's eight and a half inches, the thickness stretching Kendall's ass to the brim.

Adding in a third digit, Kendall threw his head back. His body was completely drenched in sweat, his skin red and flushed from the heat, his legs practically behind his head, and his hole loosening up from the motion. He threw a hand to his forehead, making it's way down south as he bit down on his clenched fist, trying to stifle out the moans and the "oh fuck, yes daddy"'s that were currently coming out. James spit in his hand, going back to pumping his dick, holding back from coming just yet.

As if on cue, the two highest tippers both submitted a 50 token tip goal each, almost as if they were conversing outside of the chatroom, discussing how they could fuck James over and bring all the attention to themselves.

"Ohhhh fuck, thank you so much guys. Ngh, I still feel so empty, gonna add a fourth finger in, fuck, gonna fill my hole up so nice, holy shit…. just 150 more tokens left, ngh, ohfuckyeah, let's see how fast we can hit the cumshow goal…" Kendall practically spat out, the sudden quick pace of the chatroom flustering him a bit.

True to his word, he added in a fourth finger, his hole stretching out even more as he rapidly thrusted them in and out, his ass getting put to work. Screaming at this point, the blonde's backwards cap having shifted, now covering his eyes, it was the hottest thing James had ever bared witness to.

"Oh god, love feeling my ass getting wrecked, fuck, probably gonna shove my whole fucking fist in next time. Oh god, fuck me daddy, make me your dirty little whore. Want you to choke me, and, nghh, make me feel so gooood…" Kendall gasped out, spitting out the last words, his breathe getting very heavy and his moans more drawn out. Clenching his ass against the four digits, the burn of the stretch making him feel like he was heaven, he barely managed to choke out what he wanted to say.

"Gonna blow my load soooo soon, oh god, somebody please get us to goal, don't know howmuchmoreicantake…"

This was all James needed to hear. Feeling his own orgasm coming very, very close, he quickly entered in his tip amount, his vision hazy as he could feel the knot in his stomach. Tapping the confirmation bubble, James was met with an unfamiliar sound he hadn't heard yet during this show, the sound of coins falling and a little virtual "Woo Hoo!" calling out!

The blonde's eyes widened at the view, although they quickly closed again as he arched his back, rapidly thrusting his fingers in and out of his ass, moaning as he came all over himself, the cum sticking to all of the hairs on his stomach. Moaning out James's name, well, DiamondBoi's name, he panted heavily, his eyes glossy and his smile stretched from ear to ear. James was right there with him, his load shooting out all over himself, some hitting his happy trail and some hitting his grey tank top that had been pulled up to the middle of his chest. Taking deep breaths, James let out a lazy smile, not sure exactly what had happened, but the sound of Kendall moaning his name as he came was all that mattered. Collecting the cum on his stomach and rubbing his hand on the tank top that would definitely need to be washed, James felt like the man.

"Ohhhhhh my fucking godddd, holy shit! DiamondBoi! 1,500 tokens! Fucking A man!" Kendall yelled out, his face a mixture of disbelief and surprise, letting out a hearty chuckle as he just witnessed what happened during his show. "Dude! I fucking love you so much, nobody's ever tipped me that much!" Kendall said, his hands on his head as he struggled to find the words to say at this exciting moment.

James, on the other hand, felt his face drop. 1,500 tokens? One thousand and fucking five hundred tokens? Holy shit, what had he just done? He must not have noticed the extra zero he attached to the end of his tip note. He wanted to scream, he had just tipped the equivalent to that of $150 fucking dollars, seeing that he only had 300 more tokens left on his account. Rubbing his other hand through his hair, he didn't know what to say, barely able to type out a half-hearted "you deserved it stud", which the blonde practically screamed and giggled at.

So he just became Kendall's most favorite user ever, but at what cost? With the money troubles he was currently facing, the last thing he needed was to tip close to $200 to some random fucking guy on the internet. He was fucked.

"God damn, guys, let's give a round of applause to our highest tipper, DiamondBoi! Fuck my head is still spinning, I can't believe this!" Kendall beamed, his smile not giving the same usual effect to the guy on the other side of the computer screen. As every single user in the room congratulated James on his awesome tip, Kendall was still feeling so giddy. As he dragged his fingers through the coarse hairs on his torso, trying to collect as much of the cum as he could, he brought his finger up to his mouth, his tongue gliding all around the cum-coated digits.

"Fuck, that tastes so good, but I wish it was yours, Diamond. I'm pretty much forever indebted to ya, huh?" Kendall moaned out, his fingers licked completely clean, despite the few drops of cum that had gathered on his thick facial hair. Licking his lips, he smiled at the camera with half-lidded eyes, eternally thankful for what James had just given him.

James just wished he could have enjoyed this moment a bit more.

"I knew it, I fucking knew that snake of manger that Zevon kid has would make this so goddamn difficult. Agree to his shitty terms? Does he know who James fucking Diamond is? I make the rules, it's gone this way for every negotiation I've done and he wants to sit here and completely dictate this business deal. Fuck him." James sighed, pinching the bridge of his nose as he tried to wrap his mind around the contract Dak's management tried to spring on him. He was beyond pissed at this moment, he didn't have the time to be dealing with these ridiculous demands.

"Listen James, it's not that bad. Dak Zevon is only asking for another few million, we can deal with it. The percentage of revenue he wants from the product line is crazy, I know, but we can work something out. Don't stress out, just take a breather and we can go from here." Kelly said, sitting at her desk as she sorted through the various forms that would need to be filed in order to progress with the sponsorship deal. The sound of her voice already calming the company heir to calm down a bit, she looked behind her shoulder, giving James a reassuring smile.

"Sigh… yeah, I know. It just pisses me off that Hawke is trying to make it seem like we desperately need his client. Granted, we do, but what kind of example are we making of this company if we'll just sit there and buckle under to his demands? Shit, this is so frustrating." James said, giving a half-hearted smile to Kelly to show that he truly was thankful for her help.

"Believe me, I get where you're coming from. Don't worry that pretty little head of yours, sweetie, I'm gonna head over to Gustavo's and show him everything, see if he can make any sense of it. If there's anybody who knows a thing or two about unfair contracts, it's him." Packing everything up, she checked her phone, shooting a quick reply to whatever potential contact Diamond Cosmetics had. "It's already going to be three, I'm gonna take a late lunch and then work something out with him for the rest of the day. I'll call you if we make any progress today, okay?" Kelly said, her arms full with her heavy workload, yet her face showing no signs of stress or fatigue.

"Awesome, thank you so much Kelly. I'll probably be here until seven, if anything comes up after that just shoot me a text. Good luck." James waved her off, breathing a sigh of relief once he realized that his business partner had everything under control. As the door closed, he was left alone to his own thoughts, something he was hoping he could put off until later.

It was already night time, and James was still beyond stressed out. After a brutal business meeting in which Hawke had completely grilled him, getting him to promise things he wasn't sure he could fulfill, he was just on edge the entire time, becoming more and more annoyed at each smirk Hawke gave him every time he rolled his eyes at his demands.

It also didn't help that he went into the negotiation with a clouded mind. After waking up to a pretty significant bank statement, setting him back $200 which he just didn't have, James would have murdered himself if he could. He was a fucking idiot for wasting so much money on some random guy who jacked off online for a living. He wasn't even that good looking, he was hairy and scruffy and kind of greasy, but James knew he couldn't deny that he liked it.

However, a part of James had really liked spending all that money on the blonde, finding it hot that his contributions lead to whatever sexual act it was that Kendall would perform. There was something so stimulating about it, the level of power he had over him, something that really got James off.

He didn't think it was a sort of sugar daddy complex he was going through, spending big bucks on his little plaything to make him happy. No, it was something about the control it granted him. He would make Kendall do whatever it is when he wanted, the blonde eager to follow through with it.

It was arousing for James, and he hated himself for it.

As he got ready to end his work shift, he still hadn't received a call from Kelly, no doubt the contract causing some trouble for her and Gustavo. Deciding to call it a day, he couldn't wait to get home and finally put his feet up.

He also knew that he couldn't and wouldn't have a repeat performance of the previous night. Despite how much he wanted to.