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It’s not that Dean doesn’t get horny.
There isn’t anything farther from the truth, actually. He’s twenty-four years old, no longer constantly stuck at his dad’s side and free to choose what hunts he takes, what motels he shacks up in and how many hours he spends reading lore. That sort of liberation is a turn-on all by itself in Dean’s book.
The problem also isn’t Dean’s sexuality. He is definitely, definitely attracted to women. Both men and women, but mostly women. He’s lost count of the amount of daydreams he’s had of pinning a beautiful lady down in his bed—or, even better, getting pinned down by a beautiful lady in his bed. Kissing her, biting her, feeling her teeth on his neck, on his shoulders, feeling her nails scratch down his back… Yeah, Dean likes women, for sure.
No, the problem is a little more complicated than that.
To put it simply, you can’t exactly nail a woman when you don’t have a hammer.
Well, to Dean’s knowledge, at least. He’ll learn soon enough that that isn’t the case, and he’ll curse himself for not having this knowledge when he turned down that hot emo chick back in Nevada after a tough salt ‘n burn. Or that gorgeous bartender down south with wide hips and a rack to die for who served him at least two free drinks after he miraculously survived a chupacabra the night before. Or—and this is the most painful one—the literal goddess, complete with sparkle-in-the-light brown eyes and acres of smooth amber brown skin, who’s been subtly flirting with him ever since he showed up at the bar.
The bar he left. With her. Because Dean Winchester is a weak, weak man.
“Do you always zone out during conversations, or are you trying to tell me something?” Cassie teases, smiling at him over her shoulder as she steps deeper into her bedroom.
Dean’s embarrassment manifests, a warm red flush spreading over his freckled cheeks, dusting his ears, running down his neck. He stands up straighter, stops leaning against the doorframe, and tries to focus on what the woman is saying, the gentleness of her movements when she slips out of her cute button-down top, the black lace of her bra and underwear snug against her smooth dark skin.
Dean is a flirt, yes. It’s almost compulsive, the way he looks at a person from across the room, his knowing smirk like a red-tinted spotlight. He likes flirting, he likes pretty people, and he likes the idea of sex. But he usually chickens out before it gets to this point.
Truth is, he’s terrified of disappointing people. And people will be disappointed when they find out playboy Dean Winchester can’t fuck them into a mattress like he’s expected to. Really, why else would they entertain him? It’s not like his personality makes up for anything. He’s loud and impulsive and rude, and by the time you’re ready to look past that, he’s already gone.
And now Dean is coming to terms with how terrible of an idea this is. He should’ve declined Cassie’s offer when she found him drinking alone at the counter, staring at nothing with even more nothing swishing around in his head. He shouldn’t have followed her back to her place like a puppy chasing a treat, cloudy-headed and damp between his legs. What an idiot he is. The one thing people actually want him for is the one thing he can’t provide.
Cassie must notice his panic because she pulls her shirt back over her shoulders and crosses her arms over her chest. There’s no anger on her face, no annoyance, not even pity. She looks worried and a little guilty as she comes back, looking up at him with those striking doe eyes, framed by feathery curly hair that Dean wants to fist and tug on like an animal.
“Are you alright?” she asks. “We don’t have to do this if you don’t want to. I’m sorry if I came on too strong.”
Dean’s hands find Cassie’s shoulders on their own, his eyes moving down to the skin of her collarbone peaking out.
“Dean?”
“Yeah,” he chokes out. “I want to, it’s just…” His hands drop back to his sides, already missing the warmth of her body. He can’t stop thinking about how warm she is, how warm she’d be pressed against him, hands tangled in his hair, or his tangled in hers, touching and feeling and—
“Just take a deep breath, alright?” she says, taking his hand in hers. Warm. How long has it been since Dean held hands with someone? His avoidance of sex doesn’t apply to kissing (more accurately: sloppy make-out sessions in grimey bars, sometimes alleyways if he’s feeling extra scummy), but were any of those people this gentle with him? This tender?
Dean can hear his own heart pounding in his chest, and it makes him dizzy. He wants this so bad, so so bad, but he knows he can’t have it. There’s something wrong with him, with the way he was built, and he can’t do this. He has to leave.
He has to, and he doesn’t.
“I know words aren’t your thing,” Cassie says with a soft smile, “and usually that wouldn’t be an issue, but right now I need you to communicate with me. Can you tell me what's going on?”
Her thumbs rub circles on the backs of his hands, and he imagines pulling her arms up, wrapping them around his shoulders and kissing her hard. He thinks about lifting her up by her thighs, carrying her to the bed and tossing her down. Kissing her more, slipping his hand into those pretty lace panties, feeling how soaked and ready she is for him…
“I want to do this,” he breathes, “I want you, I just dunno how to, uh…”
Cassie’s smile is something ridiculously giddy. “Whatever you’re comfortable with, Dean. I’m not picky. Though I am curious about how a flirty guy like you managed to stay a virgin for this long.”
Dean’s blush returns, and he leans forward and down, tucking his head in her collarbone, turning so his lips brush against the side of her neck. “Not a virgin,” he mutters.
Cassie cards her fingers through his hair, letting him nuzzle into her like a big cat. “What is it then, sweetheart? You can tell me.”
Dean’s words fail him, so he chooses a more hands-on approach. He takes her hand, the one not in his hair because he truly can’t part with that feeling, maybe not ever, and pulls it down to the waistband of his jeans. He has to take a few breaths before his courage kicks in, popping the button and leading Cassie’s slim fingers down, down, down, raking through his thick pubic hair and toward the wetness between his legs.
He expects her to rip her hand away and call the whole thing off, and he’s pleasantly surprised when she doesn’t. Instead, she presses her fingertips into his clit, drinking in the shaky exhale he lets out against her neck.
“Is this okay?” she asks, adding a bit more pressure as she circles it.
Dean nods dumbly, his hands snaking around her waist.
“Oh, baby,” Cassie cooes. “Did you think this was going to be a deal breaker for me? Not at all.”
Dean groans, leaning into her a little more. “I can’t fuck you the way I want to,” he admits, “the way you want me to.”
“I want you any way I can have you,” Cassie corrects him. “And you most definitely can fuck me. Come here, I want to show you something.”
She leads him across the room, and Dean fights off a needy whine when he’s pulled off of Cassie’s shoulder. She sits on the bed, and Dean sits beside her, watching silently as she pulls a box out from under her bed. She takes out a fake dick, royal blue and made of silicone, about eight inches long complete with a few fake veins running from base to tip, and an adjustable nylon harness.
“Usually I wear it for my partner,” Cassie says, “but I think it suits you. Do you want to try it on?”
Dean nods, accepting the toy when Cassie hands it over. It’s heavier than he expected. He looks at Cassie for answers.
“It vibrates, too,” she says. “Here, let me help you put it on.”
Dean peels off his jeans embarrassingly quick, though the boxers come off slower. Cassie is patient with him, one hand on his knee and the other stroking the toy. When Dean’s ready, she helps him into the harness and adjusts the straps to fit his hips. On the inside of the harness, there’s a small nub that presses against his clit. He assumes this is the part that vibrates.
Cassie smiles at him, gorgeous and excited, and Dean is drunk with lust. He still feels clumsy, unsure how to work this thing, but again, Cassie is patient. She pushes herself up and swings a leg over Dean’s thighs, planting herself in his lap. The toy stands proud between them, nudging against Cassie’s lacey underwear when she experimentally rolls her hips forward.
Meanwhile, her fingers dance up his biceps, palms sliding into place on his shoulders, then to the back of his neck, pulling him closer. She leans in so her lips brush against his ear, and when she speaks, it’s like a gentle breeze on a hot summer day. “Do you want to fuck me, Dean?”
Dean’s words fail him yet again. All he can do is nod, keeping his hands planted firmly on Cassie’s hips.
She chuckles at that, nosing her way down Dean’s neck, pressing a kiss just below his ear. “Have you done something like this before?”
“No,” Dean whispers. “But I can– I can do it.”
Cassie doesn’t comment on the obvious level of desperation in his voice, but her lips twitch against his skin. “I know you can, baby. And I’ll let you, but first I need to show you the ropes.” She smiles completely now, kissing again before pulling away ever so slightly. “I need to show you how I like it, don’t I?”
“Yes,” Dean blurts. Honestly, he’d agree to anything right now if it meant keeping Cassie’s body pressed against his. This is the closest to heaven he’s ever been, probably ever will be.
Cassie is kind when she pulls him into the center of the bed, pushing his shoulders so he’s flat on his back. He appreciates that she doesn’t make a move on his shirt and keeps quiet if she notices the bandages wrapped tightly around his chest. The reminder of their existence makes Dean a little nauseous, so he focuses on the woman above him, how her thighs bracket his hips so perfectly and how the tips of her curls tickle his skin when she leans forward.
“Tell me if I do anything you don’t like,” she says.
Dean nods, squeezing the meat on her thighs as her lips connect with his neck once again. He can’t even comprehend why or how this goddess put herself in the same sentence as the words “don’t like.” Dean is so painfully turned on right now, so enamored by her, he doesn’t even know what to do with himself.
He watches intently as Cassie maneuvers out of her underwear, tossing the pretty lace panties over the side of the bed. She’s warm and wet when she settles back into Dean’s lap, sitting up and grinding against his thigh. And when she smiles down at him, Dean’s heart does three cartwheels in a row.
“Can I use your hand first?” she asks. Dean is too quick to provide, taking his left hand off her thigh and finding hers somewhere between them. “Good job, baby, thank you,” she praises, pressing a kiss to his wrist. Dean shivers when she guides their hands down and turns them so his palm is facing up. She uses his middle and ring fingers to work herself open, sighing contently when Dean takes control with exploratory scissoring motions.
“Good?” he asks, adding some more pressure, a little rougher.
“Mhm,” Cassie grins, leaning back with her hands on his knees. She’s getting wetter and wetter, her insides softer and more relaxed around him as he continues. “Good, it’s so good, Dean. Add another one, please.”
He complies, squeezing his index finger beside the other two. He can feel her clench around him, soaking his hand and grinding down to meet his curious, determined fingers. He picks up the pace, eyeing her chest and the smoothness of her skin. As gorgeous as that bra is, Dean wants it off.
“Okay, that’s enough,” she huffs. Her thighs are shaking, holding herself up, and Dean feels a swell of pride. He takes his hand back and pushes his fingertips into her mouth. She hums appreciatively, sucking and licking, and when she’s done, she lets Dean have a turn. There isn’t much left to taste, so he quickly dips his fingers back into her pussy and then sucks the new wetness off his fingers, fighting the urge to squirm with excitement.
At the same time, he feels the phantom pressure as Cassie’s hand circles around the base of the toy, giddy when she raises her hips more and pushes the head in. The sound she makes when she sinks down is gorgeously obscene.
“Fuck, you feel so good inside me,” she whispers, running her palms over Dean’s collarbones, resting on his shoulders. She grinds down once, twice, three times, and Dean has officially adopted a new religion. Cassie Robsinon is his goddess, beautiful and divine in every sense of the word. In addition to the breath-taking view, Cassie’s weight pushes the toy harder against Dean’s clit. The combination has his breath stuttering. He’s so loopy with pleasure, it’s indescribable.
Cassie rides him for a while, praising him softly every time one of his little whimpers stretches into a groan. She leans back, presumably to hit her own sweet spot, and gives Dean a front row seat to this new perspective of her body, warm tones and smooth lines. Dean wants to get his mouth on her, he needs to, but he’s trapped beneath her, forced to watch as she pleasures herself on top of him. Dean tries to check in with himself, to figure out what it is about this that has him feeling better than he’s ever felt before, but the reasons are stacked too high. He loves being useful, loves being in this beautiful woman’s company, loves having her attention, loves the zing of pleasure he gets whenever she decides to roll the right way and reward him. Everything about it is intoxicating.
Eventually, though, Cassie’s hands move to Dean’s wrists, guiding him to hold her even tighter. “Here, baby, bend your knees,” she instructs. And Dean does as he’s told, like the good boy he is, planting his feet and subsequently pushing deeper into the woman above him. “You think you can fuck up into me like this, sweetheart?”
Dean nods, shifting a bit to get himself more comfortable, more confident.
“I need you to use your words, Dean,” Cassie hums. “My needy bitch better not be just a pretty face. I like ‘em at least a little smart, y’know.”
“S-sorry,” Dean chokes out, letting out a pitiful sound somewhere between a gasp and a whimper. Cassie’s teasing him so well, riling him up inside and out, it’s hard to focus. “I c-can, I can, please.”
Cassie’s hands cradle his face, and one of her thumbs traces his bottom lip. At the same time, she presses her hips down more, more pressure on Dean’s clit that’s already soaked from the subtle slide of the toy. “You can what, Dean?”
“I can use m-my words,” Dean pants. “I can f-fuck you, please, please, I can.”
“Good boy,” Cassie praises, drawing the words out. They drip like honey into Dean’s heart, into the burning creature inside him begging for approval. Cassie gives it so freely, so kindly, and Dean wants to cry. He can feel tears pricking in his eyes and he bites his lip to keep from sobbing.
“Oh, baby,” Cassie cooes. She runs her fingers through his hair with so much tenderness, scratching his scalp and bending down to kiss his cheek as she does so. He wants her to yank and pull so badly, to treat him rough and tap into that attitude he saw at the bar as she turned away every man on her way over to Dean. But instead he’s patient, keeps his mouth shut as Cassie pets and coddles him.
“My little crybaby. You look so pretty when your eyes are all wet. Those pretty lashes clumping together.” She peppers kisses over his eyes, then she moves her mouth to his ear, her breath subtle against his skin. “You like when I call you a good boy, Dean? You like being my good boy?”
“Fuck, yes. Yes, please, I do, I like it,” he whines, pushing his hips up, hoping to hear that sinful moan she gave when she first sank down. He’s rewarded with something similar, a small gasp that makes his heart beat a little faster, a little harder.
“Then you better behave for me, baby. Fuck me nice and deep,” Cassie orders, sitting back up to smoothe her hands down Dean’s sides. Her hands leave for only a moment to unclip her bra and toss it away, revealing perky breasts that Dean is obsessed with. He wants to wet her tits with his mouth, wants to suck bruises into them and grab them as she rides him, but that’ll have to wait. Cassie has different plans for him right now.
“No slacking off, sweetheart,” she warns, shifting a bit to give them the best angle. Dean’s legs are still bent in the perfect position for him to fuck upwards; he’s just waiting for Cassie to give the greenlight. “You better use all that muscle you got and make me cum hard. Maybe if you follow directions, I’ll give you a reward. But you have to keep being my good boy, my good bitch.”
“I can! I-I will, I will, please,” Dean gasps, rutting up some more and feeling the pressure against his clit. God, he feels so stupid but in the best way. His mind feels clear and cloudy at the same time, stupid with lust and desperation and the need to be a good boy for his lady. A good bitch. Fuck, he’ll do anything, anything she asks, as long as it keeps feeling like this, like high on touch and tenderness and teasing with spurts of roughness that get him even wetter. He’s craving more. More, more, more. And he’s ready to beg for it.
Cassie must see it because she smiles, smiles so soft and so sweet, and Dean leans up to kiss her again, hungry, then rolls his hips and pulls hers down, forcing his cock even deeper. He’s brimming with energy, licking into Cassie’s mouth when she moans, letting out a soft sound of his own when her hand finally fists in his hair, tugging his head back and exposing his neck.
“I’m going to mark you up so pretty,” Cassie murmurs against his skin. “I want everyone to see the rewards you get for fucking me so good.”
His next thrust up is involuntary, and Cassie falls forward, her chest pressed against his. Dean takes this as a greenlight and picks up a sharp rhythm, angling himself just right as he pistons in and out. Cassie practically screams with pleasure as she tucks her face against his neck.
“Keep going, keep going,” she pants, “Fuck, that’s good, your cock is so good, baby.”
Dean groans, slamming her down as he thrusts up, feeding on the desperate sounds she makes.
“You’re gonna make me come, Dean,” Cassie breathes, and Dean nearly loses it when her teeth scrape his skin. He whines, moving faster, breathing harder. Cassie seems to catch on, stabilizing herself as best she can and reaching for the remote control she tucked off to the side earlier. With the press of a button, the toy starts to vibrate, and Dean sobs, tightening his grip on her even harder. Part of him is worried he’ll leave bruises, but most of him is desperate to.
Cassie leans down again, tugging his earlobe with her teeth. “What do you need, baby?” she asks. “I need my pretty bitch to tell me what he needs.”
Thousands of filthy ideas overcome him, but Dean spits out the first thing that comes to mind: “Bite me. Fuck, bite me hard, please.”
“Of course, sweetheart,” Cassie cooes. “Anything for my good boy.”
Dean cries out when Cassie yanks his head to the side by his hair, exposing the column of his throat and sinking her teeth in, definitely hard enough to bruise. She holds him when he twitches, grinding down on his cock and humming when his hands travel up and into her hair, pulling her impossibly closer. He’s coming almost instantly, locking up and then shaking and crying softly, and then Cassie pulls off his neck and moves higher, biting down harder, shaking with an orgasm of her own.
She clicks the toy off when they’re both trembling from overstimulation, panting like animals. The toy is soaked, and Dean’s shirt and bandages are damp with sweat. Cassie rolls over, letting the toy slip out, and curls into Dean’s side, eyes fluttering closed.
After they catch their breath, Dean moves to the edge of the bed and stands up. Cassie giggles as he tries to wiggle out of the harness, eventually crawling over to help loosen the straps. The toy falls to the floor, and Dean kicks it off to the side next to the pile of fabric that is Cassie’s clothes.
“You up for a shower?” Cassie asks.
Dean freezes. That would require removing his shirt and bindings, and…
“I won’t join you if you don’t want me to,” Cassie says in that soft, loving way Dean is so unused to. “I don’t mind waiting.”
Showering alone somehow feels worse, which is another new feeling. He isn’t sure how to express it, but he does his best for Cassie’s sake. “Come with me,” he mutters, “just…”
“We can keep the lights off, and if you feel uncomfortable at any point, just say the word,” Cassie says.
Dean nods. He offers his hand to Cassie, helps her stand up on her shaky legs and moves with her to her bathroom (which is a lot bigger than any motel Dean’s ever been in, he pettily notices).
As promised, they keep the lights off, undressing in darkness with the water running to heat up. Dean kicks his bandages and tank top into the corner and steps under the hot shower water. Cassie follows shortly after, her chest to his back. He’s almost half a foot taller than her, so it’s a little silly, but Dean likes it anyway. They stand under the spray together for a while, slowly inching together until Cassie’s cheek is pressed between Dean’s shoulder blades and her thin arms are wrapped around his stomach.
“You’re really something special, Dean,” Cassie whispers.
He isn’t sure what to say.
Thankfully, Cassie doesn’t take offense to his silence. She reaches for her soap and net sponge and hums as she cleans herself. Dean is handed a regular wash cloth, apparently unfit for the net sponge, but he uses the same delicious-smelling soap. Once Dean has scrubbed himself down, satisfied with his smell, he loses his patience. In a bold move, he turns around.
“All done?” Cassie asks.
“No,” Dean answers. “Cassie, I’ve gotta tell you… I’ve never, um… I’ve never done this part before.”
“Showering with someone?”
Yes, but that’s not what Dean is trying to communicate. He glances between Cassie and himself, his chest, and after a few ticks of silence, Cassie understands.
“Oh,” Cassie says. “Thanks for trusting me, then. I have to say, though, it’s not healthy to bind with bandages. You could really injure yourself.”
Dean just shrugs. His chest isn’t big enough for it to be a big deal, but Cassie’s got a point. He gets banged around enough by the supernatural; he doesn’t need to be hurt by anything else and have it fuck up a hunt.
“I have a trans friend on campus,” Cassie mentions. “I could ask him where he got his binder. I won’t tell him about you, obviously, but if that’s something you wanna look into…”
Dean wants to cry. “That’d be awesome,” he breathes. “Thanks. Seriously, you have no idea how much that means to me.”
Cassie goes on her tippy toes and presses a chaste kiss to Dean’s lips. “You’re welcome, Dean. By the way, that means you have to give me your number.”
Dean smirks. “After that orgasm? I’d be crazy not to.”