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There's a stack of pillows on the bed, and Hobie is reclined against them as casually as ever. He's not nervous the way Gwen is, he's been here before and he's nothing but excited, a grin painted on his handsome face. He opens his arms along the pillows and gestures for her to come to him. "Why don't you come over here, love, we'll get nice and comfy."
She bites her lip from where she stands to the side of her bed. She takes him in with a slow, deep breath, from the socks on his feet, to the same trousers that he always wears, and those belts, and -- and the strap harness he's wearing, she's never seen him wearing that before. She quickly averts her gaze so she won't get caught staring, away, and then back up to his face. She likes him a lot and she really wants to do this, but she's still nervous.
He's grinning when she looks at him, and he asks her, "See something you like?" His confidence is comforting, in a way that makes her feel wanted.
She can do this.
But she still looks away with a pout when she says, "Maybe."
She stops fidgeting with her hands to crawl onto the bed, over to Hobie, where she turns and settles into his open lap. The butterflies in her stomach freeze as he wraps his arms around her and nuzzles up behind her ear. "That's it," he encourages. His voice is soft in her ear, and she can hear him smiling, feel it against her neck, even if she can't see it. "Feels good, doesn'it?"
Gwen has to let out the breath she didn't know she was holding to answer him. She gives a hesitant laugh to cover up her breathlessness, she can still feel his lips on her neck, his nose behind her ear. Through her embarrassment she answers him, "Yeah, it does..."
Hobie only hums in response. He kisses her neck, and lets it linger until it seems like she's calmed down a bit. "That's good. I want you to feel good." He starts to rub his thumbs along her sides where he's holding her. "Where can I touch you?" he asks. They've made out before, but she's never let him touch her before.
She wasn't ready, she wasn't ready.
She'd turn away from his kisses, his promises of sweet relief, Gwen red faced and hard and just saying, "I can't," and Hobie would hug her and tell her it's alright, next time, when she's ready.
But tonight is different, because things have changed. Gwen confessed to Hobie that she'd started touching herself after their makeout sessions, and that she thought she was ready to try the real thing.
They're taking it slow.
"Um," she starts. She doesn't know what she wants - she does know what she wants, but... what if it's not what Hobie wants? Or what if she's bad at it? Her words fail her, so she finds Hobie's hands with her own and starts to guide them over her body. Slowly up and down her sides, getting used to the difference in the size of his hands compared to her own. It's really Hobie touching her, she's really going to do this.
She watches as she moves his hands up to cup her chest, but it feels so much better when she closes her eyes and she feels Hobie's fingers brushing her shirt over her nipples. The first sparks of pleasure land squarely in her groin, and she just knows Hobie is grinning again, and she flushes warm with vulnerability. No one's ever seen her like this before.
Hobie kisses her neck again as he starts touching her tits, and her hands fall away to grip into fists at her sides. The friction of her shirt on her nipples is just right, hardening buds slipping between Hobie's long, relaxed fingers, gentle and tender, until Gwen is filled with the urge to start rolling her hips. She's semi hard already from the small, steady pleasure of having her tits groped and she starts to have a new desire.
Hobie sees the tent growing in her shorts, his head rested casually on her shoulder to watch himself touch her, and she bites her lip as he chuckles and continues to take it as slow as Gwen wants. That's what they agreed on. He says nothing as he feels her catch her breath, go stiff in his arms, wanting, resisting, nervous. There's nothing she wants more than for Hobie to touch her, but there's also fear. She can't believe this is really happening, that Hobie really wants her like this, she's afraid that any minute now Hobie will change his mind and it will all be over.
"T-touch me," she says, shakily with the breath she can't quite catch. After a deep breath in, she adds, "Please..." She juts her hips to indicate where she wants him to touch, and his chuckle gives her butterflies all over again. She's warm and comfortable in his lap and she wants him to touch her and he's going to touch her holy shit.
Hobie hums and brings the slow caress of his hands to a stop. Gwen can feel his breath on her neck, and she's still reminding herself to breathe normally when he kisses her there. He slides his hands down her body, moving one arm to wrap reassuringly around her waist while the other moves further down.
He touches the bulge in her shorts with just his fingertips at first, finding and tiptoeing his fingers along the line of it, because he's a tease and he likes to watch Gwen squirm as he takes his time getting there. Gwen can only bite her lip and watch, with her fists still balled at her sides, as Hobie slowly lowers his whole palm down to cup her. "Like this?" he asks, softly, with his lips still touching her neck and his nose behind her ear.
"Y-yeah," Gwen agrees, because Hobie has her cock in his hand, but then realizes that's actually not what she wants, so she says, "I mean- n-no! Yes and no. Um..." A cringe, because she's still embarrassed to say what she wants. She shouldn't be, Hobie's been great through everything so far, but she can't help it. She feels vulnerable and open and fragile. If things keep going well, Hobie's going to be inside her. No one's ever been inside her before, except for her. It's something special, and she's ready to give it to Hobie. But first, she has to tell him, "I mean u-underneath... please, do it underneath..."
"Ooooh~" Hobie teases in a low, vibrating sing-song. "Don't mind if I do," he says, and Gwen is blushing and holding her breath again as Hobie slides his hand up her cock until he's got her button between his fingers. He undoes her shorts slowly, leaving them both in suspense as he unpops the button, pulls down the zipper. He reaches inside and palms her again through her underwear, which strains around her fully hardened cock.
Gwen doesn't remember to breathe until Hobie says it, "Breathe, love," he says, right against her neck, still warm, still comforting, still sending beat after beat of pleasure rippling down her body with sweet, indulgent kisses. She longs to have those lips on hers, but her longings are interrupted by the unmistakable sparks of pleasure she feels as Hobie starts to stroke her. She still feels vulnerable, and still wonders if it's okay to be this vulnerable with Hobie, but the pleasure-chasing part of her doesn't care anymore. She can say what she wants. What's the worst that could happen?
After letting Hobie stroke her enough to ruin her underwear with a wet spot, she says, "I want you to kiss me." And then, "And I want you to touch me for real."
"You want me to touch you for real, baby?" he repeats, still stroking her with one casual hand. Gwen nods, and Hobie starts kissing up her neck, moving to cradle her down beneath him while kissing up her jaw, her cheek, to her lips, kissing her down into the nest of pillows. They kiss indulgently, like they've done so many times before, but this time Hobie's got his hand inside her pants. Which he removes as he backs away and says, "I'll grab the lube, I'll just be a second."
Hobie slips away from her, and she takes the opportunity to strip herself of her shorts and underwear. He's only gone for a second, and soon he's coming back to Gwen, taking her by her naked knees and fitting his body between them. He checks her out openly as he settles between her legs, her soft thighs, her cute little bush, with just a peek of her tummy behind the shirt she still wears. Gwen tries not to notice Hobie looking, filled with embarrassment to be so on display, but the popping of the lube bottle grabs her attention again.
She watches Hobie squeeze the lube onto his fingers, smear it onto his palm, and reach for her. It all happens so fast, so casually, no hesitation in Hobie's moves. He can't wait to start getting real moans out of her, after how responsive she's been so far. He wraps his wet fingers around her warm cock and gives its a few strokes to smear the lube around.
Gwen sucks in a breath as Hobie starts to move his hand on her, and she bites her lip as the ripples of pleasure start moving through her. It intensifies when Hobie starts thumbing more intentionally around her glans, slow swipes, slick friction, torturously good. He tightens his grip around her just right and finally gets her to whimper, sweet nothings to his ears, and he makes a pleased noise back at her. "I can't wait to have my fingers inside you, feel you squeezin' me every time you make a noise like that," he says, and she whimpers again, and she can feel herself clenching with anticipation. She's fingered herself before, but this is like nothing she's ever experienced. She feels like Hobie's barely touched her and she's fallen apart.
"Please..." she begs, on panting breaths with her eyes squeezed shut. There's no coming back after this. "I... I want to feel you inside me."
Hobie coos at her, with the widest grin painted across his face. "As the Princess commands." He continues to stroke her, slowly shifting his hand downward until he's massaging her taint and then teasing two fingers across her hole. She looks like she's about to cry when he circles back around with one and dips the wet tip inside. "Are you sure you want this?" he asks, without moving his hands from where they are.
Gwen nods her head, eyes still shut tight, but that's not good enough for Hobie.
"Look at me," he says.
It takes her a moment, but she opens her eyes. She has to blink the tears away first, but she opens them. When she's looking at Hobie, she says with her words, "Yes, I want this. I'm just... nervous. You're really good at this."
Hobie gives her a softer grin. He doesn't tell her that she's just extremely easy to please. Instead, he helps her bend her thighs back, and leans in over her to give her a kiss. He sucks her lip into his mouth as he slips the first finger inside, and Gwen moans. It's soft and breathless, and leaves her tingling with pleasure as she feels Hobie prod inside her, kiss her, prod, kiss, prod, kiss, until she's doubtless and dizzy. She's not scared anymore, she just wants, "More..."
Hobie smiles into their kiss and gives her an extra tender one, before shifting his hand to tease a second finger at her hole. He takes the first one out, just to hear Gwen huff, before sliding both of them back in, just to hear her hiss. She sinks into her nest of pillows, cozy where she's folded under Hobie, blissed out on kisses and hyper aware of the way Hobie's long fingers drag in and out of her. He curls them until he finds her sweet spot, and massages his fingers into it until Gwen can't take anymore.
"Hobie!" she cries, her cock and her eyes leaking with overwhelm. She'll cum any second if Hobie doesn't stop, but she wants to take it to the next step first.
As if reading her mind, his eyes on her red face, he asks, "You want me to fuck you now, love?"
She nods, and he kisses her again before using his support arm to push away from her. His cock has been left aside, washed and ready to be used, so he grabs it and fixes it to the strap he's already wearing. When he comes back, Gwen is exactly where he left her, with her knees pushed back and her face flushed and damp. He gets between her legs again, and when his hips bump up to hers, their cocks slide together. It makes her gasp and arch her back, over sensitive and ready to cum, and she tastes like an angel when he kisses her.
He reaches for the lube again, and smears it on his cock until it's nice and warm for her, and then braces himself near her hip to line up. She can feel the tip of his cock press against her hole, and she holds her breath with anticipation as he nudges at it, teasing her, testing the elasticity. She thinks he'll put it in any second, but he just keeps teasing her, until she whines and says, "Please, Hobie... put it in..."
She feels wet and slick everywhere Hobie smears his cock tip. She's hyper aware of the way her rim stretches as he slightly pushes in, then slips back out. "Hobie, please..." she whines again, face hot, fingers gripping into the backs of her thighs where she holds them back. The shame she felt in the beginning is still there, but it no longer outweighs her need. She needs Hobie inside her.
"Don't worry, baby, I've got you," Hobie assures. With a tilt of his hips, he presses in, and Gwen groans as she feels herself open up around him, take him in, squeeze around him. Slowly, he pushes in about halfway, then pulls almost all the way out, then pushes in again. Gwen short circuits as she tries to catch up with the reality of what's happening, until she realizes it's inside and she rolls her eyes back with a whimper.
Hobie takes it all as a good sign to keep going, and he slowly starts fucking into her. He appreciates her from her watery, dazed eyes, to her leaking cock lying on her tummy, and he decides that she deserves another kiss.
He lowers himself until their hips touch, and he can reach Gwen's lips with his own. He continues to hump lazily into her as he gives her an indulgent, open mouthed kiss. She moans into his mouth, sticky and sweet, and worms her little arms up around him to hold him closer. She wants to tell him how good she feels, she wants to tell him she loves him, but the kiss prevents her, and all she gets out is desperate little moans and whines for more. "More, Hobie, faster, more," she mumbles, wet between his incessant kisses.
Hobie hums in response to her, gradually pulls away from her kisses to look down on her with hooded eyes. His hips have come to a stop, with his cock buried inside her, so he can ask her a question. "You want more?"
Gwen nods her head, looking up at him through watery lashes. Her cock is flushed and leaking and she's so close to cumming, but she wants to feel Hobie fuck her, really fuck her, she wants him to get as lost in it as she is.
Hobie gives her another kiss before sitting up and pulling out of her. She whines as she's left empty, but she doesn't have much time to complain as Hobie takes her and rolls her onto her stomach. He takes her hips and pulls them up, spreads her thighs, positions her on her knees with her chest down on the bed, and lines up his cock again. When he pushes in, she gives a long, satisfied moan, as every inch on him rubs against her prostate. The angle is perfect and leaves her with her eyes rolled back again, her fists tight in the blanket.
It doesn't take long for Gwen to finish once he starts thrusting, already teetering on the edge. She holds on for as long as she can, but it's Hobie's words that finally push her over. He holds her by the hips as he buries himself again and again, watching her greedily take him in, it's hypnotizing, there's only one thing he wants. "I wish i could cum inside you," he says, burying himself again with a long, slick stroke. "Fill you up with my seed and breed you." He reaches around her to grab her poor, sensitive cock and feels the last dribbles of her orgasm leaking out of her. He hums and asks, "All finished then?"
Gwen is hardly listening though. Her ears are ringing and everything is hot and quiet and there's a comfortable weight settling inside her that comes screeching alive when Hobie starts to stroke her. Over sensitive and painful, she whines and grips the blanket, only just barely managing to catch Hobie's question. She shakes her head the best she can from her position, pain sparking back up into pleasure the longer Hobie touches her, and she realizes she wants more.
"Mmm, that's good..." Hobie purrs. He sinks all the way inside her as he lies himself down across her back. He hugs her with one arm and continues to stroke her with the other hand, until she's hard and leaking and red and begging him again.
"Hobie, it's too much, oh my god, please, oh, Hobie," in an endless stream, half muffled where she bites the back of her own hand to try to keep quiet. She's full and she's overstimulated and she's on fire with feeling and for once in her life her head is completely empty.
She starts crying when she cums again, and she doesn't realize she's doing it until Hobie is wrapping her up in his arms and shushing her. He pets her hair and kisses her cheek and his cock sits between her legs as a dirty reminder of everything they just did.
She starts crying harder and she doesn't even know why. Hobie continues to comfort her until she calms down and the room quiets.
"You did great," he tells her, and she can only grunt in response. She turns and buries herself in his chest and they stay there quietly until Gwen finally sighs and breaks the silence.
"That was..." she starts.
"Mhm," Hobie responds.
"Can we take a shower?"
Hobie grins. "Of course we can, love."