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Cruel Yet Agreeable Punishment (Closed with michime)

"Y-Yeah...!" Steve was in no mood to argue. His ass was quivering at Will's touch and teasing: this old man brought out the bottom in him like no other. And to think it was all an act. He really was hot for his landlord...but at least there was a payoff!

He felt the fingers slowly ease their way past his ring. "AH...! S-Sir!" The pain was laughable compared to the sweltering heat in his brain. He wanted those fingers - he wanted Will's cock - to test his limits and make him feel amazing. The chat didn't even occur to him anymore. He moaned without restraint. Will could do whatever he wanted to him now.
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Will slowly moved his fingers back and forth twisted and turned making sure he gave Steve pleasure while helping the guy's bank account. "Look at you, just begging for more," he chuckled before he curled his fingers upward. "You're getting hard pet. Start stroking yourself."
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Without a word, Steve obeyed. He maneuvered his hand around his stomach and found his weeping shaft, making it just as clear as his words how badly he wanted all this. He gripped it and gasped. Even the normal friction of pumping his fist up and down was intensified with Will teasing his fat ass. He did it slowly, trying to stave off any money shot that would leave fans either confused or disappointed or expecting too much to come afterward. But the more he struggled to keep his fans in mind, the harder it became to surface above the way his head swam in suspended disbelief.

"Sir...Sir!" He trembled every time his 'sugar daddy' dramatically moved his fingers. He tried to think of more dirty talk. It was tempting to just moan and whine the whole time...what was happening to him? "Look at what you've done to me, Sir. This is what I am...and I fucking love it. Thank you so much, Sir..."
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Will let Steve stroke himself for several minutes as he played with the man's ass. He carefully glanced at the timer in the upper right corner of the screen. They had a little less than 10 minutes to go before the show ending then Steve could rest for a bit.

"You have such smooth skin now," he used his other hand rub circles over Steve's broad back. "You were hot before but now you're perfect. All fat like a blimp. Makes me wish I could ride over the ocean."
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Steve probably would have wondered how the hell Will was hiding this filthy mouth all these months. But the things Will were saying left him whining and begging wordlessly for more of his attention.

"I'm your big, bloated blimp, Sir. I'll be as big and round and cock-hungry as you want. I love being your pet...!" Steve squirmed and clenched around the fingers, trying to have them stretch him out even more for all the world to see. He was absolutely delirious now. Any way that Will teased and/or pleased him made him want more and more.
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"My greedy little pet always wanting more," Will teased with a quick glance at the timer. He slapped Steve's ass again before he used his fingers to fuck the other man. His thrust were a bit stronger now that the muscles loosened up. "Do you need a third, pet?"
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"MNNNGH!" Steve struggled to make sense of the sounds coming from him, but he was torn between senselessness and exhibitionism. He had to decide...and this was all for money, even as much as he enjoyed it. "Yes...! Please, Sir, I need more!"
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Will gently added a third finger and played with Steve's ass a bit more. He had to admit, it was a very nice ass, round and perfect for slapping. Will was an ass man himself and Steve's was something.

"My pet has such a great ass. I can play with it so much." He petted Steve's hair for good measure.
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Steve would let Will do anything. That was exactly how he felt right now. So much attention and affection, saying his fat ass was sex appeal rather than a turn off, those fingers, those suspiciously talented fingers...! He suspected that Will would actually be his sugar daddy if given enough leeway, in his own sex-addled mind.

"It's yours, Sir! I'm getting it nice and fat, just for you! I want it to be perfect." He nearly swooned at Will patting his head. He wasn't sure if he meant what he was about to say, but it felt right to just say it. "I'm so happy you found me, Sir. This is who I'm meant to be."
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Will leaned over a bit and kissed the back of Steve's neck. "See, how he reacts to me? He's such a good pet. Knows what he needs to be. He's such a good pet. Ass open and responsive. He's so warm and inviting sucking up my fingers."

He wiggled his fingers up and down as he moved his hand back and forth. "Do you need more my pet?"
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Steve gave up on trying to process anything anymore. He wanted to be completely present with his 'sugar daddy'.

"Yes...! Yes, please, Sir, I need more of you! Please touch me more, Sir...My whole body's on fire just from you touching me. It...it wouldn't matter if I died from anything you did to me, because I would already be in heaven, Sir!" He felt the whole of his lower body tremble in anticipation of having even more of Will teasing him so tenderly.
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Will made sure the camera caught the perfect angle so the viewers saw a fourth finger enter Steve's ass. He turned his hand so his palm was face up then curled his fingers.

"How do you like being scratched this way?" He asked as he stretched Steve's hole. "How does my pet like having himself stretched and scratched?" He pushed his hand in passed the knuckles. "You need me so bad, pet. Just tell them how much you need me. What I do to you. How big you got for me. How you want to get a nice set of titties that I can milk?"
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"Sir...! Sir, I'm hopeless without you! If you left me, I couldn't go on, I just couldn't! You showed me what it's like to get big and round, and I'm addicted...Sir, it's fucking amazing. I started eating and eating and eating...everything you gave me and made for me, I ate it without a second fucking thought. I want to be HUGE. And you want me to be, too..."

"I'll be so happy when I have the kind of chest you love, Sir." He pinched his own nipples and felt genuinely disappointed in how small his chest was. Some distant part of him may have broken out of the illusion with enough scrutiny, but he was too far gone with Will doting on him. "Fat and full of milk. Like I'm a goddamn preggo that lactates. I dream of you sucking on them and drinking from me. That kind of feeling...! And it's the least I could do for how well you take care of me, Sir." He clenched around all four fingers. "Everything you do for me makes me feel incredible, Sir!"
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Will worked Steve's ass open until the last second of the show. He got Steve so close to climax after the moment the feed died, Steve clenched around Will's fingers.

"You did so good," he admitted as he leaned over and kissed Steve's neck. "You really had me going there." He didn't pull his fingers out yet letting Steve come down. He made sure not to move too much but he didn't stay still either. "Can you move?"
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Steve blinked several times. It was over. And he was still here with Will: he hadn't woken up or anything. That was quite the show, but...

"Y-Yeah, I can move." He didn't try, though. Will hadn't removed his fingers yet. God knew why, but he wasn't about to let this moment end before it had to. "Thanks for pulling that off, Will. Where'd you learn to play to the camera like that, damn!" Stalling. He had to ask, but he was scared to actually say it. Will's fingers felt genuinely good...

"Hey, uh...I feel so weird asking this, but...could you do me a favor? Just a favor between men. Could you, erm...help me finish? I know the show's over, but I got left hanging so close. Y-You don't have to; I'm sure it's just my dick talking here. But I'd appreciate it."
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"You want to finish over your computer?" Will asked before he looked around. "That's not going to be comfortable. I don't mind moving if you need it." He still had his hand in Steve's ass and he could just give a few strokes and be done but that didn't feel right. Plus Steve liked his computer area neat. He could reach what he needed for the show.

"I'll let you in a secret part of my life, Steve. Back in the day, I worked for a very small movie but highly specialized video company. I learned a lot of tricks." He smiled as he wiggled his fingers then let his thumb move over the rim. "It's been a very long time since I did this. I didn't think I would miss it when I quit but this makes me nostalgic."
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Steve felt a little dizzy with confusion and pleasure as he reappraised Will, still showing off this hidden expertise of his by teasing his rim. So the old man was basically admitting to being a porn director. Then why did he need help learning how to talk dirt--

A thought struck him. Will was a very clever man, and evidently very sneaky. But was it possible that Steve just missed signs from him that he was just as interested as Steve was? Maybe...maybe this was a sign to be a little more assertive.

"Oh. Yeah, I'm sorry, I just got lost in the moment." He reached over to start eating the milkshake Will brought over. He felt bad that it sat there getting warm. Wait...he felt bad? Or was it more like a wasted opportunity? "We can go over to the bed or something." He didn't mention how Will would move his hands as they moved. It was better to let Will decide that for himself, Steve decided.
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"Why don't we go to my bedroom?" Will offered as he picked up the pace of his movements. "I have a King sized bed that you can stretch out in instead of your little mattress. You'll be more comfortable."

He glanced down at his hand shoved up Steve's ass then grinned. "Have you ever been fisted?"
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What was even happening? Steve was living with an old freak this whole time, and Steve was worried about offending his 'sensibilities'. Any control he had over the situation was ebbing away even faster than before. "S-Sure, we can use your bed."

But...after months of keeping his secret hidden, maybe that wasn't such a bad thing. Maybe it was okay to let Will take the lead today, if nothing else.

"I, ah...not really," answered Steve honestly. "I'll give it a shot. I thought about it before, but I never got curious enough to try it. And I'm usually a top anyway." He felt Will's fingers shamelessly stroking his insides and quickly went back to full tumescence. "Usually."
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Will gave a small smirk before he used his free hand to turn off the computer. He didn't stop playing with Steve and even pushed his fingers deeper into the man.

"I learned this trick when I worked," he explained as he fanned out his fingers. "It's a great way to control someone with pleasure." He curled his fingers upward pressing against the sensitive skin.

"You move your fingers a certain way and boom, you can make a person do whatever you want." He teased before he slowly moved Steve to an upright position. "I'm not going to take my hand away but we are going to my bed. I'll finish you off there. Sound good?"
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