Word Count: ~1700
Disclaimer: Not my characters.
A/N: This was written for the prompt Dean and Lisa both get off on pegging. Preferably face-to-face. at blindfold_spn. This has been edited and altered somewhat from the original version.
Also at AO3.
When they do it isn't up to Dean.
Well, it sort of was, the first time. Lisa had joked about pegging once, and Dean had just shrugged and said if she wanted, he was game. It had been...well, awhile, but there'd been a time when he'd loved getting fucked. He'd never tried pegging, but he had figured that maybe this would be - well, it might work for him. Plus, boobs and getting fucked? Yeah, Dean could work with that. Lisa had gotten this gleam in her eye before changing the subject.
But he'd forgotten the entire conversation by the time Lisa decided to spice up a blowjob with a bit of fingering. She'd never done that before and fuck, Dean had gotten off so fast and so hard, it was like her lubed finger in his ass had a direct line to the part of his brain that said "come your brains out now."
Lisa had been pretty pleased with herself, and a week later she'd produced the dildo for the first time.
So it isn't up to Dean. He doesn't know when he's going to climb into bed, snuggle up to her, cup her breasts, and run a hand down her smooth, flat stomach to find her cock jutting out.
This night, like every time, it's a surprise.
"Mmm, you like my dick?" she whispers in the dark. "It's so hard. You getting hard too, baby?" She wiggles her ass against his cock, letting him know she can feel him, how hard he's getting.
"Oh, you are," she murmurs, and there's a purr in her voice that Dean doesn't hear that often, and he knows how into this she is.
"Fuck, Lisa." He can hear the little whine in his words, and he has to take a breath, and relax. He knows what's coming.
"You want it, don't you?" She nuzzles her head under the crook of his chin.
"Oh hell, yeah," he says, and she rolls over. The room is dark, just the faintly orange light of the streetlight outside through the lace curtains illuminating her face. The curve of her cheek is all all that's visible but Dean thinks that she's beautiful. He lets himself imagine waking up to her for the rest of his life, just for a moment.
"Turn over, baby," she tells him, and Dean can tell that she's smiling as she gently pushes at one shoulder. He obeys, and waits.
It doesn't take long. He hears the gentle whirring sound of her vibrator for just a moment before it's pressed up against his hole.
"Does that feel good?" she asks.
"God, yeah," he mutters, because it does. It feels fucking amazing. There's a click, and the vibrations increase in strength, taking this from "pleasant sensation" to "holy shit". Lisa keeps the vibrator pressed up against him for what seems like a long time, but it's probably just a few minutes. Dean keeps his eyes closed, doesn't say anything, just waits and breathes. Lisa leans up and kisses the back of his neck, and cups the right side of his ass in her hand for a moment. She reaches around, strokes up and down his dick just once.
"You're so good, Dean. So good for me."
She kisses the back of his shoulder and he leans into the pressure. He hasn't told her he loves her yet - she hasn't said it to him, either - but he thinks he probably will pretty soon. It's kind of hard to be sure, but he thinks what he feels is love.
And then there's no thinking about love or forever or anything else, because there's a click of a bottle and then her finger is wriggling its way into his ass. He sighs at the pressure on the sensitive nerves, the tight muscles already loosened by the vibrator.
Lisa licks a trail up the knobs of his spine and blows hot air onto it. Dean shivers. All this attention, all of it focused on him can be a little overwhelming. Lisa moves her finger around a little, stretching him out, before withdrawing it to add some more lube, before sliding in two fingers. Her fingers aren't long enough to reach his prostate, but the stretch itself feels pretty fucking good.
"You doing okay?" Lisa asks, and Dean realizes that his breath is coming hard and fast now - panting, really.
"Yeah, keep going," he murmurs. "Can't wait to feel you inside me."
She lets out a low sigh at that, and presses her mouth against his back as her fingers work their way back and forth, humming a vibration into his skin.
"Do it," he says.
He can feel her smile spread against his skin.
"You do it," she says. She pulls her fingers out of him and rolls onto her back. In the dim light, Dean can see her cock sticking out obscenely from her body.
And then he's straddling her, his own cock bobbing up against his stomach. The mattress and bedding are softer and more comfortable in this position than any motel room bed. He can see her grinning up at him, and he leans down to kiss her. Lisa kisses back hard, pushing herself up on her elbows to press her body against his. Their dicks rub together, and it's not quite like frottage with a real cock, but the friction sends sparks up Dean's spine.
Dean breaks the kiss by sliding down, licking at her jaw and then down to the hollow of her throat. He's about to nibble at her neck when he realizes that if he covers her with marks, she probably won't wear those low-cut tops for awhile. So he moves down, smiling at the gasp she lets out when he takes her left nipple into his mouth.
Lisa has really sensitive breasts. Dean likes that he knows that.
"Shit," she mutters. "Oh god, Dean. Keep doing that." Her hips - and the cock - buck up, and Dean can feel his own dick twitch in response.
It seems manifestly unfair to pay attention to one breast and not the other, so after a minute of tonguing at one nipple, he switches to the other. She lets out a stream of quiet curse words in between tiny gasps and moans. Her hands snake up around his neck and dig into his hair, scratching at his scalp.
She's writhing and shuddering, and Dean has to put his hands on her hips to steady her. He gently pulls out of her grip and leans back. The bottle of lube is lying on the bedspread and Dean grabs it, uncaps it, and lubes up Lisa's dick quickly. He's had enough foreplay and is ready to get fucked.
Dean is loose, but not enough that it doesn't ache and burn at the stretch, sliding down on Lisa's dick. It's slick and hard and smooth and it's not really like a man's dick, but it feels amazing.
"Oh god," he groans as he presses down. "Fuck."
"You okay?" Lisa asks. Dean can hear the concern in her voice and for a moment it's like his throat has closed up and he can't answer.
"Yeah," he finally gets out. "I'm shit, I'm fine."
To prove it, he presses down the rest of the way in a single thrust. A moan escapes from his lips, loud enough that Lisa puts a finger against his lips. Dean opens his mouth and sucks the finger in.
"Shhh," she says. "Ben."
Dean nods in agreement, and shifts his body, taking in the sensation of being filled. It's good, and when he looks down and sees Lisa looking up at him, it's really good.
She reaches around and smacks his ass.
"Get goin'," she says. "Ride me, cowboy."
He does. He starts with circling his hips, rocking back and forth until he finds his prostate. He can feel his eyelids fluttering uncontrollably, his eyes rolling back into his skull at the sudden shock of pleasure.
"You like my dick?" Lisa whispers. "You like riding me?"
"Love it," he grits out as he slides up and then back down her cock. She holds it steady for him, her hand wrapped around the base, before sliding her hands up over his ass. Dean grins. He knows Lisa's got a thing for his ass.
He doesn't mind.
Dean speeds up his rocking, leaning down just enough to cup his hands over her breasts, flicking his thumbs over her nipples. He's rewarded when Lisa arches her back and bucks her hips, pressing up into him in the most fucking awesome way.
He can't take it anymore, and he grips his dick, starts to jerk himself off. Lisa swats his hand away.
"That's for me," she tells him and props herself up on one elbow and takes hold of his cock. She jerks it hard and fast, not at all in time with his own motions, but it doesn't matter at this point. Her cock hits his prostate again and he's trying to make it last longer, but it's too late; he's coming, hot onto her hand and his stomach. He shudders and bites his lip to keep from shouting.
Lisa's cock doesn't soften and slip out, so Dean lets it stay stiff in his ass for a few seconds, feeling his breath slow down.
It's Lisa's chuckle that brings him back, and he looks down at her with a smile. He crawls forward, the cock popping out, and kisses her.
"Your turn," he says, reaching down to unbuckle the belt that holds her dick on before climbing down the bed to fit himself between her legs.
She's so fucking wet already, so turned on by fucking him, that a single swipe of his tongue has her gasping and grabbing at the sheets.
"Damn, you love fucking me," Dean says, still kneeling between her legs, breathing in the scent.
"Don't sound so pleased with yourself," Lisa tells him.
"Oh, I am pleased with myself," he tells her. "And in a few minutes, you're gonna be pleased with me too."
She bucks her hips up.
"So get to it, cowboy."