In all her years in his employ Pepper has seen him naked a number of times. She was seeing him nude on an almost daily basis at one point and barely batted an eyelid any more. She'd caught him in quite a few different sexual positions around the house, with quite a few different women and that did make her blush bright red for days afterwards, made her stutter and run off. She had caught him masturbating in most of the main rooms of his house and a whole lot of hotel rooms and that always had a strange effect on her. Blushing but no stuttering, and an odd melancholy mood that he didn't really understand but intrigued him.
Tony had seen Pepper naked once.
He had a habit of invading her space but she'd defined a single boundary early on in their working relationship. He wasn't allowed to let himself into her apartment or she'd quit. He was allowed to be invited in, and had been frequently, but he couldn't let himself in. And he really didn't want her to quit so he stayed out.
He had noble intentions, it was the first time he'd been unable to get hold of Pepper since she'd started working for him, and he'd panicked. He'd called her at all hours and had gotten a response in the past, woken her up in the night, in the middle of meetings, gotten her out of the shower, called her on planes, even on a boat once. In every country he'd took her to but the one time he tired to call her when he knew she was in her apartment, taking her first sick day, he'd gotten no answer.
For four hours.
So he'd gone over, taken Happy with him, used his key to let himself in, the burly bodyguard standing in the hallway, ready to dial an ambulance on his order.
He should've left when he heard to shower. That had been his first mistake. Or second, depending on what counted as mistakes.
He wasn't even supposed to have a key, he'd had one made without her knowledge when they were out of the country once. Just in case, he'd told Jarvis, and himself and when he walked into her place, the sound of the shower was clear. And he should've left, he knew that, but he was afraid she'd fallen.
He definitely should've called out for her first.
He kept going through the apartment, following the sound of running water until he came to her bathroom. The door was open a little, steam escaping and he forgot the panic the moment the water was shut off. He also forgot to turn around and leave, safe in the knowledge that she was alive and well enough to shower. He was about to push the door open when Pepper opened it herself, naked and dripping wet, a large towel in her hand and covering nothing.
Two more new things occurred.
He heard Pepper scream for the first time, moments before slamming the bathroom door shut and yelling at him. He had quick eyes, a good memory, and he'd taken everything in in the moments before she'd disappeared from his view.
And, for the first time, he yelped. Like a startled dog. Even though deep down he knew what he was doing, what the chances were, he was still surprised. He yelped because imagining and seeing were very different, and the reality of it was a little more than his brain could really take.
His apology was sincere but stuttering, an entire conversation through the thick wooden door as he tired to explain himself, and she told him she'd been asleep, sick with fever, not in danger, every word laced with hysteria.
He apologised in one way or another for months afterwards, after she didn't resign and he gave her the key to her apartment back. And the spares. And after she changed the locks.
He still apologised on occasion, years later, to appease his own guilt rather than really needing too, and without making it too obvious to Pepper what he was apologising for.
Usually for masturbating while thinking about her, with very clear images of her body in his mind. He only ever thought about her when masturbating, not when he was with another woman. He couldn't risk ending up in the tabloids for calling out his PA's name while in bed with another woman.
Because he always ended calling out her name into the darkness when he thought about Pepper. Her perfect body, hot little grin on her face (she wasn't angry in his imagination), hands on her hips. His own hand around his hard dick, moving slowly at first, thinking about Pepper teasing him, with her little hands all over his body, touching every inch of his skin, his own hands busy with her breasts. Breasts he knew for certain would fit perfectly in his hands. He'd done the math. After coming out of the shower and into the cooler air, her nipples had been hard and they were again in his imagination.
He was blessed sometimes. His intellect and imagination meant he could perfectly visualise new weaponry he wanted to design and women he wanted to sleep with, all in his head.
He thrust his hips up into his hand on occasion, unable to help himself, unable to stop the little movements that didn't quite synchronise with his hand. He wasn't entirely in control of all parts of his body around the waist and groin area at the best of times, and now, with a tight grip around his shaft, and a horse cry pushing at his chest wanting to be released, he had no chance of regaining control of himself. Pepper was always a good fantasy, just the thought of the woman in bed with him had him perspiring at the brow a little, as he worked himself harder, built the pleasure up higher. He played with his balls, flicked his thumb over the head of his erection randomly, making him gasp, the push of pleasure at his chest closing around him tighter, the cry coming closer to the surface.
He knew what to do to get himself off quickly, masturbation wasn't often needed pre-Iron Man, but it was a familiar habit and he'd figured his own body out early on in his life. When he thought about Pepper though he liked to prolong it, make it as amazing as she was because he knew it was unlikely he'd ever have the real thing.
Which saddened him and spurred him on at the same time to a greater orgasm
With a faster pace of his wrist, and the little gasps getting louder and more frequent he knew he was close. He gripped the sheets and let the cry loose, yelling out Pepper's name as he came, a little yelp following, his entire body shaking from his groin up, down to his toes, then back up to his dick as he emptied himself. He was breathing hard, still thinking about Pepper and relaxing into his mattress, sticky trails of his bodily fluid marking him all the way up to his arc reactor.
Cleaning up, a little unsteady on his feet, his breathing still ragged, he thought back to that one single event in time. Taking in every inch of skin before being presented with her door.
He never did figure out why she didn't resign.