It started when Clint manhandled him into the shower; he got far more familiar than Tony thought was probably necessary, making very sure he was thoroughly clean- inside and out. Clint looked almost apologetic about it, except for the part where he kept forgetting not to grin.
As Clint roughly toweled him off, the bathroom door slid open. "Is he ready?" Phil asked.
"All clean, sir," Clint told him.
"We don't have to do this," Tony said, stumbling as Clint pushed him forward.
"You don't decide that, whore," Phil said. "I own your ass, and you're going to go make my money."
Tony licked his lips; he didn't want to get out of it, didn't even really want to pretend it wasn't as hot as it was, but a scene was a scene. There was no screwing up, not when he wanted it this much. "If it's money you want, I can get you money."
"Yes, you can," Phil said. "You can get on your back and take it. Even you should be able to figure that one out."
"That's not what I meant," Tony said. "We can work this out."
"Slick him up," Phil ordered, ignoring him.
"Wait," Tony protested, as Clint forced him to the floor, his face against the cold tile. "Wait, I don't-"
"Shut up," Phil snapped. He tossed the lube to Clint. "Make it quick."
Tony hissed as Clint pushed his fingers inside; Clint was generous with the lube and Tony wanted it, but that didn't mean it didn't hurt when somebody just shoved three fingers up your ass all of a sudden.
The dildo was big, and Phil set it down right in Tony's line of sight, sticking it to the floor with the attached suction cup. "I don't know what you're going for here," Tony said. "But I don't think it's a good idea."
"I'm doing you a favor," Phil told him. "Or do you want me to send you out tight and dry to somebody who might not bother to give you any lubrication?"
"You're not protecting your investment," Tony pointed out, trying not to moan as Clint worked his fingers faster, curling them to brush his prostate. "You don't know what they're going to do to me if they think they're not the first, if that's what they paid for."
"That sounds like a personal problem," Phil said. "That's enough. Let him up." Clint let him go, and Tony tried to bolt, just to make Clint catch him again, feel his strength. Clint got him in a chokehold, and Phil slapped him across the face. "Calm down. This only has to hurt as much as you want it to, but you're not going to waste my time."
Clint dragged him over to the dildo, and Tony got to his knees, letting Clint position it at his entrance. Before he was ready for it, Clint pushed him down, making him take it in. "Wait," Phil said, taking something off the counter and handing it to Clint. Tony groaned in frustration as Clint put the cock ring on him. It was a mixed blessing, because who knew what they were going to do to him if he came this soon- Tony only knew they weren't going to stop. "Now ride it."
Tony pushed down farther, rocking his hips slowly as he took more. "I don't have all day, slut," Phil said.
"Give a guy a break, Jesus," Tony muttered. Phil raised his hand again, and Tony moved faster. "I'm going, I'm going."
He dropped down on it as far as he could before coming back up; it felt damn good, too long since he'd taken something this big. He let it open him up, stretch him out, fuck him just right. He could come just from this, just from the thought of everything else that was going to happen, the whole situation. Phil knew exactly how to be the right kind of threatening, completely unyielding, uninterested in what Tony wanted at all.
At this rate Tony was going to need another shower, because he was starting to sweat again. He shut his eyes, but it was too hard to resist peeking when he heard the sound of a zipper. Phil was leaning back against the counter; he'd pushed Clint to his knees, and now he was feeding him his cock. His hand gripped the back of Clint's head, and Clint moaned around him, his usual oral fixation coming to the fore.
Phil wasn't paying attention to Clint, though, his eyes fixed on Tony as he moved. Tony was momentarily wrapped up in it, his hips stuttering. Phil's gaze didn't wander for an instant, his scrutiny heavy and unwavering. Now Tony really had to shut his eyes, because under that focus he wasn't going to last another five seconds.
"That's enough," Phil said, after what was probably forever, long enough that Tony's thighs were starting to hurt, to say nothing about his poor constricted cock. Tony opened his eyes again, in time to see Phil push Clint's head away and tuck himself back into his pants. Tony wasn't quite sure who he was talking to, but he gratefully stopped. "Clean him up and do the rest of it."
Clint wiped his mouth and stood up; Phil grabbed him before he could go, kissing him hard and slapping his ass before walking out of the bathroom. Clint did as he said, leading Tony over to a chair by the vanity. This was, strangely enough, the part that Tony was the most skeptical of. Having Clint style his hair, that was nothing, though he did end up looking- appropriately enough- a little like that guy from Gigolos, but the makeup was something different.
Clint was apparently very good at it, a skill that Tony couldn't even imagine where he'd picked up and didn't know if he wanted to know. The other times that Tony had worn anything but concealer and stage makeup had been fairly sloppy, mostly drunk, and extremely inadvisable, but Clint did it expertly, swiping and blending and powdering and doing the things that were honestly kind of mystifying.
It was a strange sensation as he put on the eyeshadow, almost pleasant, but Tony made the mistake of opening his eyes in time to see Clint come at him with the eyeliner. He flinched back as Clint got close, and Clint caught his chin, pulling him roughly back into place. "If you move, I'm gonna poke you in the eye, and I'm not gonna feel bad about it," he told him.
Tony held still after that, because he honestly didn't know if Clint was kidding or not. Clint delicately applied the eyeliner and mascara before he let Tony go, surveying his work. Satisfied. he turned Tony around, letting him look at himself in the mirror. He didn't really look like a whore, but it was maybe worse this way; if Clint had just slapped on some hooker blue eyeshadow and bright red blush, Tony would look like a clown, like this was a game. Instead it looked like he'd planned for this, taken the time and consideration to look good, like he wanted this to happen.
Clint didn't give him much time to think about it, pulling him out of the chair and thrusting his clothes into his hands. It was a little embarrassing that the majority of them came from his own closet. In fairness to him, the too-tight shirt was Pepper's, but the rest were souvenirs of a different time in his life. Honestly, he could do, and had done, a lot worse than black patent-leather pants and a black-and-silver thong with studs that made it pleasingly industrial-looking. The sandals were a little embarrassing, mostly because Tony hadn't willingly worn flats since he was about twenty. They did look appropriately trashy though, so he let it slide- as if he had a choice.
Clint gave him a once over, pushing his pants down his hips a little, showing a flash of his midriff and quite possibly his thong. "Knock 'em dead," he said, giving Tony a kiss on the cheek that was clearly designed to miss the important parts of his makeup.
"I think they probably have to pay extra for that," Tony said.
"Boy," Phil snapped from the other room. "You're cutting into my client's time. If that slut's not ready, I'm taking it out on your ass."
"Ready, sir," Clint said, shepherding Tony out.
Phil didn't offer an approval or disapproval as Tony entered, just looked at him impassively- not new. "Here," he said, and Tony reluctantly went. He held up a collar, putting it around Tony's neck and buckling it. He clipped a leash to the drop ring on the front, tugging Tony close by it and examining him. "Good job," he told Clint.
"Thank you, sir," Clint said.
"I'll be back," Phil said. "If you want your reward, you'd better be naked and on your knees."
"Yes, sir," Clint said, and Tony could hear him already undressing; smart man.
Phil wrapped the leash around his hand, walking away with another word, and Tony quickly followed, not particularly wanting to get choked out.
They had to walk all the way across the floor to reach the bedroom, which was not exactly a short distance on this particular floor. It was on lockdown, but Tony still glanced at the elevator; it wasn't really like anyone would be particularly surprised seeing Tony dressed up like this, but the collar and leash was probably a little much. Phil yanked at the leash. "Pay attention," he said.
Tony didn't respond, just let himself be led. Now he was feeling kind of nervous, despite himself. It was increasingly easier to feel like he was being forced into this, like he didn't have a choice in the matter at all; something about the collar made it so much more real.
Phil stopped in front of the bedroom door. He pulled hard on the leash, making Tony look him straight in the eye. "Make it good," he said. "You won't like it if you embarrass me."
"Why are you doing this to me?" he asked, feeling real fear quicken his breath.
"Because I can," Phil told him. Still staring Tony down, he knocked on the door.
A few moments later, it opened. "Phil," the woman who answered said, reaching out to shake his hand. "Nice to see you again."
"Always a pleasure," he said.
"This is the new boy?" she said, looking Tony over- okay, no, ogling, she was ogling him is what she was doing.
"I thought you'd appreciate his first time," he said.
"I'm flattered," she said.
He smiled. "Only the best for my best client."
"I bet you say that to all your clients," she said, grinning.
"I wouldn't be very good at my job if I didn't," he said, holding out the leash. "Enjoy."
Pepper took it, pulling Tony into the bedroom. "I'll take good care of him," she promised. "Night, Phil," she said, and the door shut behind them.