Girls in the Boys’ Room

Peter/Olivia. NC-17. ~2000 words. Crossdressing.
Sorry sweetheart, Peter thinks–not one bit sorry at all–better luck next time.

Peter almost doesn’t recognise who it is, at first. The way he sits, a careless sprawl, one ankle propped up on his knee and one arm slung over the back of his chair. There’s a glass of whiskey on the rocks balanced on his thigh, long, slender fingers holding it easily in place as his gaze skips over the crowded lounge. His suit’s a classic 20s cut, double-breasted, wide-leg slacks, the thinnest black stripe run through charcoal grey. A matching fedora sits low on his brow.

In jeans, a button-down and a light spring coat, Peter might be slightly underdressed for the meet.

A waitress swings by the table, stops to grant him a wide, warm smile, and Peter hangs back, watching. She stands closer than she has to, hand resting on the back of his chair. She laughs at something he says and sashays away, returning a few moments later with a tiny bowl of nuts and a wink.

“You have a twisted sense of humour,” Peter says, helping himself to the only other chair at the table.

He tilts his head, takes a drink before replying. “I thought you’d appreciate it.”

“Oh, I do. I do. But,” Peter glances at the restaurant set just off the hotel bar, “the Clink?”

He smiles. Candlelight catches on the strong angle of his jaw.

Peter pops one of the salted peanuts into his mouth. “How’d you know I’d show?”

“Should I placate you, say I didn’t?”

Peter cocks an eyebrow. Out of the corner of his eye, he spots the same waitress headed back their way. “Another for him,” he says to her, “and one for me,” and can’t help a grin as something like disappointment clouds her face before she walks away. Sorry sweetheart, Peter thinks–not one bit sorry at all–better luck next time.

“Maybe you should be asking how I knew to get in contact with you.”

“Yeah,” Peter agrees, and leans forward, hands folded in front of his chin, “yeah. I’d say that’s a slight concern.”

Mr Long, Lean and Handsome stands up, drains the last of his drink. Peter’s gaze gets snagged on the smooth line of his throat as he swallows before slipping down the perfectly tailored lines of his suit. “Come with me.”

Peter looks quickly up. “I get the feeling that might not be a good idea.”

Another slow smiles slants his way. Peter shoves his chair back and follows him to the shiny bank of elevators on the room’s far side. He tucks his hands in his pockets, rocking back on his heels as the numbers count down.

The elevator is blessedly empty. Seconds after the door closes his back hits the wall. “Jesus Christ, Olivia,” he breathes, bracing a hand on the railing as she presses close.

It takes him too long to wrap his head around the differences. Her chest is flat against his, her shoulders somehow broader, her hold rougher. Her hair is the same, pulled back in a tight, low tail that drapes down the centre of her back, but doesn’t seem as feminine paired with the thicker line of her brows or the way she holds herself against him. She quirks a smile, shifts, lets him feel the press of her cock before the doors slide open again.

She leads the way down the hall, Peter hurrying to catch up before he gets stuck riding the elevator up the next dozen floors. Even her stride–always quick, purposeful–is different.

He reaches her side as she swipes a keycard through the lock. The tiny light flickers from red to green. She opens the door and steps back for him to go on in.

Peter grins, shrugging out of his jacket as he does. Even if he didn’t know the price tag on a Liberty suite, he’s been in enough hotels to recognise money when he sees it. The impressive riverside view dominates one entire wall of windows, city lights sparkling on its surface.

The perfectly acceptable hotel he’s been staying in is a hole.

A prickling weight settles between his shoulders. It’s been awhile since he felt like this–chest tight, stomach full of butterfly flutters. He honestly doesn’t have the first clue how this is going to go.

Olivia is still by the door when he turns around. He can’t help but stare. His mind plays tricks on him, tells him one moment she’s the woman he knows she is and the next that she isn’t, that the slight bulge at her crotch he felt before–can’t look away from now–is a real cock, that she’ll get hard for him.

“Holy shit.” Peter sits heavily on the foot of the bed. His pulse slams double-time, blood rushing through his veins so fast he’s dizzy for a moment. It clears quickly, leaves him with a hand fisted tight high on his thigh, inches away from his dick.

Olivia moves casually closer. “For a man who prides himself on his open-mindedness, you seem-”

“Incredibly fucking turned on, I know,” Peter cuts in.

“I was going to say panicked.”

“No, this is definitely not panic.” Peter scrapes his teeth over his bottom lip. “This is bitchslapped by a fantasy I didn’t even know I had.”

She kicks his feet apart, making space to stand between his knees. Her knuckles curl under his chin, tilt his head up. She’s always been self-assured, used to playing in a boy’s club and damn good at it. Seeing her like this–all swaggering confidence, cocksure–drives the point straight home.

His hands slide up her thighs as she unbuttons her suit jacket. It falls open, revealing the perfectly-pressed white dress shirt and smooth black vest she wears beneath. The familiar feel of her hips in his hands clashes startlingly with the long, flat line of her chest. It’s too easy to imagine the planes of muscle that shirt could hide.

On pure impulse, Peter presses his face to her groin. She sucks in a sharp breath, fingers digging hard into his shoulder as he opens his mouth against the soft curve of her cock. Whatever she has packed in her pants, it feels like she’s semi-hard beneath the layers of fabric.

He’s already stripping her belt out of the loops before he thinks to ask permission. She doesn’t seem to mind, playful half-smile on her face and her hips angled forward, cock rubbing against his wrist as he goes for her zipper.

He peels open her fly slowly, not sure what he’ll find or what he wants to find, usual cotton or silk and lace, something special. He feels the thick band of the dark boxer-briefs she’s wearing before he sees them for what they are, and by then her slacks are pushed halfway down her thighs.

“This is actually really hot,” he says. “Christ, Olivia, I don’t-”

She takes his hand and sets it square on her cock. “Try that.”

His answering laugh is a little bit breathless. His hands still look big on her body and she still feels so good, soft skin and strong muscle beneath her curves. He knows that it’s not a real cock cupped in his palm but when her eyes go heavy and she fucks up against his hand, it might as fucking well be for the spike of want that goes through him.

He kicks at his shoes and scoots further back onto the bed. “C’mere,” he says, propped up on one elbow, hand outstretched as she steps out of her slacks and toes off her own shoes. She kneels on the bed to pull off her socks and stays there, shirttails framing the damp spot he didn’t know he left behind on her shorts.

She runs a hand down her belly, over her cock. “That looks like you’re asking me to fuck you.”

A fresh rush of pure lust hits Peter so hard his knees jerk up. He shoves the heel of one hand against his dick and plants his feet firmly against the bedspread, unable to stop the roll of his hips.

“No,” he says, finally, pretty sure he’s not going suffer a puberty relapse and cream himself. “Not a horrible idea, though. Just come here.”

She’s all smooth satisfaction as she crawls over him, thighs edging up beneath his like she would fuck him, right now, if he would just get his clothes out of the way.

One long, slow roll of her hips proves it and Peter’s vision blurs. Christ, she’s barely even touching him and he’s almost finished.

“That’s good,” he says, grabbing at her hips to drag her closer, feel her cock pressed hard against his own. “That’s good, right?”

She catches the corner of her lip between her teeth and nods. The bleached white of her collar is stark against the flush creeping slowly up her neck. She thrusts again, harder, hands skidding over the bedspread. His stomach does a crazy flipflop as she pushes his shirt up under his armpits, twists a fist in it and leans most of her weight forward, pinning him down.

“This is better,” she says, remembering the role she’s chosen to play.

Peter puffs out a quick, “Yeah,” arching into her lazy grind. His jeans are too fucking tight, cock trapped against his belly, slick smeared so far down the length of it his balls are sticking to his shorts.

“You’re thinking about it.” She catches his wrist before he can get a grip on her vest and yank her down for the kiss he wants so bad he can already taste it. “Me fucking you like this. Pushing up inside you.”

“Maybe a little,” he hedges, testing her grip just to see the spark light her eyes. He hitches his leg up a little further, groans quietly at the way her hips shift, her cock pressed right up beneath his sac. “Maybe a lot.”

Her jaw goes slack for a moment, spine curving as she ruts against him. He’s sure she’s going to go straight for the finish before she sucks in a breath, says, “You could return the favour.” Her hand drags over his cock, squeezes just enough to make his pulse trip. “Fuck me after I’ve been in you, show me how it’s done.”

“Call me crazy,” he says, fingers scrabbling over hers as they both go for his fly at the same time, “but it doesn’t really seem like you need any pointers.”

She knocks his hand away, gets hers inside just long enough to pull his cock straight out through the slit in his boxers. Her palm curls over the tip, just enough slick there to make it easy when she starts jerking him off. She says something that Peter can’t hear over the sudden rush in his head.

Then her mouth is on his, tongue prying between his lips. His fingers tangle in her hair, knocking her hat off and she laughs into the kiss, turns it wetter, dirtier before he can catch his breath. She makes a noise, soft and quick, like she’s coming, and then he is, all the breath punched right out of his lungs on a harsh groan.

He blinks his eyes back into focus in time to watch her really lose it, head thrown back and mouth wide, lips chewed red. He palms the curve of her ass, pressing her down, and her hand slips off of his cock, come smearing up over his stomach as she slides forward. Her hand is slippery against his face when she tries to kiss him again, fumbling and off-centre.

Grinning to himself, he gathers her lax weight close, rolling over to straddle her hips, jeans stretched taut around his. She stretches out beneath him, lithe and satisfied, cock purposefully nudging his ass.

“My regular clothes are in the closet,” she says, and snaps the waistband of his boxers.

Peter sucks in a breath at the brief sting, laughs. “You don’t think there’d be a sizing issue?”

“Not enough of one.” A small, mischievous smile twists her lips. “You can always buy me a new pair.”


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