don’t mind me @pleaseignoremme - Tumblr Blog

when you experience internalized homophobia and unrequited love for your straight best friend you may or may not develop kinks or fantasies you are not that proud of… one of the hottest things for me is a roleplay where the top is straight (or at least doesn’t admit being anything else) but fucks the bottom while watching porn because a hole is a hole. if that is something you can work with just know that there it at least one person who will get horned up because of it.

thank you for this. my mind ran away, i'm so sorry.

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Pretty: A Hollanov Ficlet

rating: e | wc: ~1880 | tags: college!au, anal, feminization, “straight” ilya, discovering things about yourself by fucking your gay best friend, sex while watching porn (kinda), slight degradation, blink and you'll miss it breeding kink, One Spank, feminization of shane’s asshole (she's a pussy with she/her pronouns)

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“You said you'd do anything.”

Shane swallows visibly, the saliva twitching his Adam’s apple as it goes down. “I know.”

“So is this your limit? You’ve wanted this for five years and this is your limit?”

Shane nibbles his lower lip, toying with the hem. “I didn’t say it was a limit.”

Ilya looks his best friend up and down, a hand sliding around the plumpness of his ass, beneath the gingham skirt and over the lace biting into his cheeks. It wasn’t a demand, so to speak. More of a highly requested suggestion if they were to try this out. Lucky for him, Shane followed through. He hovers over Shane’s lips, squeezing his ass. “You wanted my attention. Now you’ve got it. Are you backing out?”

“I’m not backing out,” Shane snips, shrugging a shoulder anxiously. “It’s just…out of my comfort zone.”

“Well then, we’re even, aren’t we?” Ilya says, digging his nails into his thick ass cheek, and not entirely opposed to the high gasp Shane releases.

It took one conversation, after five years of friendship, and Shane very bashfully admitting that he’s always wondered what all the hype was about with every woman that Ilya got into bed. Shane’s attractions had always been his business. He never forced them onto Ilya, never told him he should “explore more”, they just had their own platonic intimacy apart from the sexual. Shane wasn’t flamboyant or exuberant, he was just Shane. Insanely talented hockey player, peak jock performance, captain of the McGill team, about to graduate and kick ass in the real world, in the real leagues. Ilya was just his junior league buddy-turned-best-friend whose father talked him out of hockey altogether after Junior’s and strong-armed him into a business degree to “make something of himself.”

Sometimes he thinks it’s because his father saw how good Shane Hollander was at just seventeen and knew Ilya would never be that good.

Truthfully, he’d never looked at Shane as an object of lust. He was just his best friend. Objectively attractive, sure. He could acknowledge that Shane was a beautiful man, with a gentle smile and adorable freckles. But that’s as far as it went. Until tonight.

“Did you do what you need to do?” Ilya asks, a knuckle stroking Shane’s cheek.

“Yes,” he mumbles. “It’s ready.”

“Ready for me to just slide in when I please? Like any other girl?” He clarifies, tucking a tendril from his falling bangs behind his ear, his head of hockey hair in full force and pulled into a bun at the back of his head.

“Yes,” he shivers, barely blinking when Ilya tugs at his hair tie and frees his locks for holding.

“Then get on the bed. Face down. On your stomach.”

He hears the muttered “Fuck,” under his friend’s breath, and something about it makes Ilya’s cock throb.

He’s not attracted to men. He fucks women. He has fucked a wide array of women of all shapes and sizes and backgrounds. He knows women.

Shane, well…

He knows Shane incredibly well. Just not like he knows women. But how different, really, can it be? Fucking an ass is fucking an ass, right? A fuckhole is a fuckhole. He’s done it countless times. He likes his women a little freaky, a little kinky; he’s no stranger to entering through a back door. Make Shane put on panties and a little skirt and it might as well be one of his countless hookups over the years.

Ilya strips himself naked, something that Shane has definitely seen before, but never been able to appreciate fully, so he gives him that allowance. He sees his breath catch as his cheek lies atop his forearms, waiting for him and devouring Ilya's body with his lurid gaze. Shane isn’t that far behind — the skirt and panties are all he’s clad in anyway. He throws lube onto the bed, rips a condom from the strip, and flings it, landing on the small of Shane’s beautifully dimpled back.

Laying like this, he really isn’t that different from a woman. Strong thighs, he supposes, but that’s not exclusively masculine. He’s fucked a few muscle mommies in his time. His slutty waist curves beautifully into sturdy hips, and if Shane was a girl, he’d think he could birth a baby from them. Maybe if Ilya tries hard enough, he can knock him up despite the biological setbacks. Shane would probably take him without a condom if Ilya had him stupid enough. Many woman have tried to beg for it before. He has pretty strong resolve, and proudly no pregnancy scares as of yet.

But something about the curve of that fucking waist. The deep dimples above his ass. The thick, perkiness of his cheeks. Ilya is already hard and leaking staring at him. He may not even need the porn.

He turns it on anyway, a laptop perched at the foot of the bed in front of Shane. He picked the video out specifically, long enough that he can do what he needs to do. A toned man, nothing special. A beautiful brunette on her stomach with her ass in the air and an asshole already stretched, her tits pressed against the mattress and hair flowing down her back.

Ilya can do this. Easy. Shane wanted a graduation present, and Ilya is going to give him one.

“Can we at least keep the volume off?” Shane mumbles as the woman starts moaning on screen as fingers fuck her hole.

“I like the sounds,” Ilya purrs, gripping his ass.

“Put something inside me like that and I’ll make sounds for you,” he assures.

Ilya thinks it over, and decides to give it a try. He mutes the video, leaving the woman throwing her head back in silence. That settles Shane a little, resting his head more and propping his ass in the air like a well-trained slut.

“You get fucked often, Shane?” Ilya asks, admiring his cheeks adorning the red lace. “That position seemed pretty automatic. You don’t really talk about it much with me.”

“I get fucked enough,” Shane says dismissively. “And I didn’t think you’d want details.”

“Maybe we can try in the future. You can tell me all about the men who fuck you not as good as I’m about to,” he touts as he rolls the condom down his cock and lubes himself up. With a sharp hand, he smacks Shane’s ass, and the man gasps, his shoulder blades pulling back as he arches gorgeously at the treatment. Ilya chuckles. “I should’ve known. Hockey players like it rough, huh?”

Shane, his defenses dissolving, just exhales, “Yes.”

Ilya jerks down the panties, just under the seat of his ass, and groans as he flips his skirt up. He clearly shaved, made himself smooth and pristine down the split of his ass. Ilya inspects his future dwelling and finds it dark, dusky brown, and shining with lubricant. Shaved, maybe even waxed for how smooth he is when Ilya runs his fingers over the skin. Shane inhales at the touch, leaning back into it searchingly.

“You groomed for me.”

“I wanted to be…pretty,” Shane admits quietly.

“Fuck,” Ilya whispers, dragging his thumb over his slick, clenching hole. “You are very pretty. Look at this pussy, all clean and wet for me.”

Shane whimpers into his arms at the words.

“You like that?” Ilya coos, dragging the heel of his hand up Shane’s back and tangling into his shaggy hair. “You like when I call your pussy pretty? I think she wants me to fuck her. She’s winking at me like a little slut,” he teases, pulling his cheeks apart over and over with his free hand just to rile himself up at the ephemeral sight of him.

Fuck, his best friend is hot. And he wants to fuck him. God, he really wants to fuck him. Is he really this horny that his cock is leaking over his male best friend?

Now isn’t the time to overthink it. Shane is moaning, writhing at his sentiments, and Ilya feels a flush burn over his chest as he lines his cock up to his best friend’s hole. He shakes himself out of a daze and glances past Shane’s plump lips, up at the screen where the brunette is already getting plowed by a cock not that different in size from Ilya’s own.

He makes sure to stare at the girl, stare at her face, as he plunges past the tight ring of his entrance, but all the sounds are Shane. The cry of pleasure is deeper than he’s used to, but it still makes his cock ache as he sinks in deeper and deeper. Shane doesn’t seem to mind, doesn’t tell him to stop or slow down, just moans and whines into his arms as his ass poises in the air. And when he starts to fuck, when he angles it right, Shane’s ass clamps around his dick like a vice, like good cunt when it’s coming around his cock. But he doesn’t even think Shane is close to coming yet.

That’s his prostate. Fuck, that’s hot. Ilya shifts to fuck into it again, and Shane’s thighs shudder as he keens, his hands now clutching the sheets beneath him. Ilya’s hand buries in Shane’s hair, pressing his cheek into the bed as he sets a ragged, relentless pace, feeling out what makes Shane tick like he would any woman.

“Did I find your secret spot? Your special little G spot? You like when I fuck it like that?” Ilya growls into his ear, feeling Shane’s ass bounce back against his hips as he forces himself to watch the screen again and not Shane’s pinched and pleasured face, where the woman is also being pressed into the bed and pounded, clearly shouting in manufactured bliss. But Shane’s noises are real. Very real. He knows fake when he hears it, and it isn’t when a hole is squeezing around his cock like this.

“I think I’m gonna come,” Shane whines, panting, wrapping a hand around his cock and jerking aggressively.

“Already, baby? Video’s not even half done,” he jokes, not sure where the pet name came from, but it felt natural with such a beautiful body beneath him, swallowing his cock like it's nothing at all.

“Fuck me through the whole thing, I don’t care,” Shane whimpers, and then his body jolts, his ass pulling tight around his cock as he splatters onto the interior of his skirt, panting and moaning.

It hits him all at once, a brick to the face, at the expression Shane pulls as he comes, looking so fucking beautiful, so angelic, so pornographic, but better than any porn he’s ever seen. He feels it in his fucking chest when he blows inside him, blindsided entirely and nearly blind himself as his vision blacks out before coming back in blurry and disoriented.

“Oh, fuck. Oh fuck. Jesus Christ,” Ilya babbles, running hands up and down Shane’s back as his cock softens in the messy condom. He pinches it gingerly and extracts himself, slamming the laptop shut and lumbering onto his back with a huff. “Господи. Shane. Fuck.”

“You’re sure you don’t like men? Like, really sure?” Shane breathes out with a wide smile.

“Don’t ask me that now. Let me have a fucking cigarette first.”

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@ilyasmole @loontattoo