Work Text:
“You want to do what to me?” Charlie asks, a spoonful of cereal halfway to his mouth. Wheaties and milk start to spill over the sides of the spoon, and he plops the whole thing back down into the bowl.
“It’s my turn to pick,” Harper says, not actually answering his question. “We did your thing last week.”
“Okay, but I’m pretty sure 69ing is a little bit different than… you know… what did you call it again?”
“Pegging,” Harper replies matter-of-factly. “And that was the whole point of this, to try new things.”
“Yeah, but…” Charlie is starting to run out of excuses. It’s not like he’s even really against the idea. He’s experimented on himself a bit in the past, and he had let Harper finger him during week two of Operation Expand Our Horizons (he’d put the kibosh on making a full-blown spreadsheet, but he’d caved on granting her naming rights). But getting a finger or two up there feels decidedly different than, you know, a whole dick, silicone or not.
Harper’s still giving him that look though, the one that looks like a mix between a rain-drenched puppy and an orphan begging for an extra scrap of food. It’s truly devious on her part—she knows he can’t resist that look (not that he ever tries that hard).
He sighs. “Okay, okay. Pegging it is.” Harper squeals and flings her arms around his neck, pressing her lips to his cheek with a wet smack.
“Great. How about tonight?” she asks, and he chokes on the sip of coffee he somehow thought it would be safe to take.
“Tonight?”
“Hey, go big or go home, Young,” she replies.
“I’m pretty sure that’s not the right adage for this endeavor,” he mutters under his breath. Looking up at Harper, he asks, “Do I need to, uh, do anything to… prepare?”, once again feeling completely unsure about this whole situation. Should he call Duncan for pointers? No, absolutely not. He’d never hear the end of it. And then a horrifying realization hits him. “Harper, have you talked to Duncan about this?” he asks, feeling like he already knows the answer.
“I might have texted him for some recommendations on supplies,” she replies coyly.
Charlie groans and lets his head drop towards his chest. “I’m never going to hear the end of this,” he whines.
“He was actually very helpful. You wouldn’t believe the sheer amount of dildo options on the market these days. But I think we picked out a good one.”
“We?!?” Charlie wheezes out. Jesus Christ. “You two went shopping together? For a dildo, for MY ass?” He thinks he might actually have a stroke right now. There are probably worse ways to go, but since he’s also pretty sure Duncan will manage to bring up the circumstances that led to his death in the eulogy, he’d really prefer not to.
“I just took him on the exploratory mission,” Harper says, smoothing her hands over Charlie’s shoulders. “I promise he wasn’t there when I actually picked everything out.”
Charlie takes some deep breaths and tries to get his heart rate down to something resembling healthy. And then he has a thought that makes it speed right back up.
“Wait. Harper. We’re not going too big though, right?” he says, his mind flashing through images of some of the dildos he’s seen in Duncan’s bedroom. Harper just grins and waggles her eyebrows salaciously as she turns to leave the room. “Harper, not too big though!” Charlie yells after her. “I’d rather go home!” He sighs, dropping his head into his hands as the front door closes behind her.
Jesus, he really hopes his ass is ready for whatever’s coming his way.
***
In the end, it turns out he spent an entire day having anxiety cramps for nothing. Harper shows up with a completely non-threateningly-sized dildo, holding it up for him to inspect as she explains, “I tried to find something close to yours. Is that weird? I thought it would seem… familiar?” She’s blushing a little as she says it, and Charlie pulls her in for a kiss, cupping her cheeks in his hands.
“It’s perfect,” he says. “I think. I don’t really know. But I think I can handle it.”
They take it slow, making out on the bed, slowly removing articles of clothing as if it was just another normal Tuesday, getting down to skin on skin. But then Harper turns to fumble in the nightstand, emerging with the bottle of lube they’d acquired a couple of weeks ago, and Charlie’s eyes flick to where the dildo is lying on the dresser. Harper puts a hand on his cheek, making him meet her eyes.
“It’s just us right now,” she says, as she flicks open the cap of the bottle and pours some onto her fingers. She reaches between them, her hand wrapping around his dick, and he groans at the silky-slick feeling of the lube as she strokes him. She hikes her leg up, draping it over his hip, then slides her hand around, teasing at the cleft of his ass. “Still okay?” she asks, dipping just slightly between his cheeks.
Charlie nods against her shoulder, mouthing at her neck. He thinks back to the first time they did this, and how quickly the feeling of her fingers there had gone from strange and foreign to just good. They shift around, her arms too short to get enough purchase in their current configuration, and Charlie ends up on his back, Harper straddling his thighs as she dribbles more lube onto her hands. She fondles his balls before reaching lower, pressing two fingers slowly inside.
Charlie groans, spreading his legs just a bit more, and Harper places a hand on his chest to steady herself, kissing his pecs as she works her fingers in and out. This is as far as they’ve ever gone, and Charlie realizes he’s trembling a little as Harper pulls her fingers out just a bit so she can work in a third.
“Hey,” she says, settling next to him on the bed so she can squeeze his thigh without taking her fingers out of him. “It’s gonna be good. I’ve got you.”
The third finger is in now, and it is good, a deep throbbing pulse going from his balls up to his dick, and then she curls her fingers just slightly, and Charlie gasps, white-hot pleasure coursing through his body. Harper does it again, smiling against his throat as he fucks himself down onto her fingers.
“Okay,” he pants out. “I think… I think maybe it’s time to get. You know. The stuff.”
He feels empty without her fingers inside him, and he idly swipes his own fingers over his swollen hole as he palms his dick, watching Harper work out the proper way to get the dildo into the faux leather harness and onto her hips.
“Want some help?” he asks, and she looks up at him with the determined set to her face that lets him know she absolutely needs help, and also that she absolutely will not ask for it.
He pushes himself up, kneeling on the edge of the bed as he inspects the buckles, holding the harness against her as he tightens first one side and then the other, checking to make sure it’s not too tight. “Okay?” he asks, sitting back to take in the whole look, and fuck, he was not prepared for how hot she looks, hip cocked just slightly, hand now wrapped around the shaft of the dildo.
She nods, looking down at herself and then back to him. “Do you know what made me decide I wanted to do this?” she asks rhetorically, pushing Charlie back onto the bed as she kneels over him again. The dildo drags against his stomach and he shivers.
“I thought about how much I love getting fucked by you, and I wanted to see what it felt like. To be on the other side of it for once.” Her eyes are dark with desire, and Charlie feels breathless looking at her.
“Okay then,” he says, “come on. Time to see what all the fuss is about.” He flips over, wiggling his ass suggestively, and she laughs, slapping his flank lightly as she gets into place behind him.
He jumps slightly as more cold lube dribbles down his crack before Harper works it in between his cheeks, teasing the tips of her fingers inside. “Spread your legs for me a little more,” she says, her voice gone low and husky. It sends another shiver down Charlie’s spine, and he’s happy to comply, Harper’s knees knocking against his as the blunt head of the dildo presses against his entrance.
He breathes out, trying to relax his body as Harper slowly pushes inside, and they both moan in unison as the head of the dildo slips inside him. “Fuck, this is so hot,” Harper says under her breath, barely a murmur, and Charlie wishes he could see what she’s seeing. Maybe next time they’ll set up a videocamera.
She presses forward just a bit more, and Charlie groans, willing his body to loosen up and take it. It’s so much better than just her fingers, and the initial dull ache fades into the background, replaced by the exquisite pleasure of being full of dick—full of Harper’s dick, he thinks to himself—and he presses his ass back at that thought, feeling Harper bottom out, her hips now pressed solidly against him.
“Is this… is it good?” she asks. He can tell she’s nervous, her hands fluttering awkwardly along his back, and Charlie tries to give her a thumbs up, but just ends up face-planting into the pillows. It drives the dildo deeper inside him, and he moans as she hits that spot again, the same one she’d found with her fingers, that sends electric sparks through his whole body. “Fuck, Harps. Yes, yes, you’re doing amazing. Just keep fucking doing that.”
She pulls back, thrusting in a few stuttering jolts before settling into a rhythm, and Charlie is absolutely man enough to admit that this is one of the greatest things he’s ever felt. She leans over him, and he loves the way her breasts feel pressed against his bare back—yet another checkmark on the “reasons to do this again ASAP” list.
Harper has always seemed so petite to him—not delicate or fragile by any means, but just the right size to tuck into him. He loves how it feels as though he could wrap his entire self around her like a reverse safety blanket. Now though, it’s like she’s surrounding him, touching him on every inch of his body in a way that almost feels impossible. Her arm snakes around his waist, wrapping around his dick, and he gasps at the overstimulation.
“Harper… Harper,” he manages to pant out. “Harps, I’m not gonna last much longer. Fuck, this is so good.”
“I need you,” she pants out just as desperately, and Charlie whimpers as she pulls out suddenly, flopping next to him on the bed. He turns his head, barely processing what’s going on, and sees her fumbling at harness’ buckles. “Charlie, please,” she whines out, then makes a triumphant sound as she gets the first buckle open. “I need you to fuck me now.”
He scrambles up with a speed that surprises him, blanketing himself over Harper’s body and pushing the dildo and harness aside enough that he can touch her, sliding his fingers through her wetness, rubbing against her clit until she’s writhing below him. “Come on, come on,” she demands, grabbing at his ass to pull him forward, and he slides his hands up to her breasts, thumbing at her nipples as he lines himself up and presses inside her.
She throws her head back and groans, one leg wrapping around his thighs as she lifts her hips up against him, and he picks up the pace. One of Harper’s hands is still resting on his ass, and he wishes her fingers would reach around to his hole. He feels a little empty, and if there was time, he’d suggest they try to get the dildo in while he fucks her, but he’d meant it when he said he was close, his orgasm already building as he fucks into her hot wet tightness.
She slides her other hand between them, fingers on her clit, and the press of her hand against his dick is the last straw, his orgasm bursting through him until he’s seeing stars. Through the rush of white noise in his brain, he hears Harper letting out high, breathy gasps, and her thigh gives one final tremble before dropping down.
He pulls out gently, settling onto the bed and curling around her. The harness is still half on, and he uses the last of his energy to unclasp it, letting it drop onto the mattress as he pulls Harper against him. She’s loose and pliant, smiling sleepily up at him.
“You liked it?” she asks, fingers running down his side.
“Yeah,” he replies, “definitely. Fuck, that was hot.” She grins up at him, and he leans down to kiss her. “What about you? Fulfill all your fantasies?”
“Mm,” she murmurs, stretching languidly against him. “Definitely. We will be doing this again.”
Charlie is half asleep already, Harper a warm weight against him and every inch of his body humming in contentment. He turns to click off the light, pulling the blankets over them as they both drift off to sleep.