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.
--
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)
--
“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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today's theme: horny texting throughout the years [more]
Shane: I know you’re not going to be happy but I can’t stand it anymore. I’m shaving.
Ilya: Noooo
Ilya: One more night
Shane: Ugh Ilya...
Ilya: One more beard burn. You always shave so I can't feel
Shane: Fine. But I get to decide where. And you don’t get to bitch about it.
Ilya: I think after this week I am used to your scruff against my face and thighs sweetheart
Shane: I’m not talking about your face or thighs sweetheart.
Ilya: What else?
Ilya: Oh
Ilya: I’m coming home rn be ready
_ _ _
Ilya: This is Shane Hollander?
Shane: What?
Ilya: My friend gave me #
Ilya: Love to watch u play. I have seen all ur games :)
Shane: …okay.
Shane: Thank you?
Ilya: My friend said u would be shy lol
Shane: Not shy. Just trying to figure out what’s going on.
Ilya: What’s going on is ur biggest fan is texting u to say ur the hottest player in the league ;)
Shane: Thanks.
Shane: That’s inaccurate though.
Ilya: ?
Shane: Ilya Rozanov is the hottest player in the league. By far.
Ilya: I mean hottest in looks
Ilya: Sexiest
Shane: I know.
Shane: That’s Rozanov.
Ilya: So you do like men. Good to know ;)
Ilya: You are very good at stick handling. Maybe sometime u can handle mine.
Shane: I don’t even know who you are.
Ilya: [One New Photo]
Shane: Wow. Didn’t realize I had such jacked fans.
Ilya: Big dick too
Shane: Don’t believe you.
Ilya: [One New Photo]
Ilya: You like?
Shane: I like.
Ilya: How much?
Ilya: Would u fuck a fan Shane?
Shane: Maybe one. If he could be discreet.
Ilya: Trust me if you come by it will be you who has to try hard to be quiet ;)
Ilya: [Location Sent]
Shane: Wait is this real?
Shane: You’re in town rn?
Ilya: Door is unlocked. Don’t keep ur fan waiting Shane Hollander.
_ _ _
Shane: I’m hard.
Ilya: And hello to u too ;)
Shane: Hello. Your flight got in? You’re home?
Ilya: Yes. And you are at awards dinner yes?
Shane: Yes.
Ilya: Lol you like hockey a little too much i think
Shane: Shut up. It’s not because of that.
Ilya: Sure
Shane: I can’t stop thinking about last night.
Shane: I can still feel you inside. What the fuck did you do to me?
Ilya: Fuck Hollander.
Ilya: That is your fault. You were begging for it so deep
Ilya: Go to bathroom and call me
Shane: I can’t.
Ilya: Why not
Shane: I can’t stand up.
Shane: They’ll see.
Ilya: Oh u are HARD hard huh sweetheart
Ilya: Show has started?
Shane: About to.
Ilya: Wait for lights to go out. Then go to the bathroom.
Ilya: And until then don’t think about me under the table sucking your poor big achey cock.
Shane: Oh my god fuck you. Why would you say that to me right now!
Ilya: You love it
Ilya: Like how u loved it hitting that deep last night
Ilya: We could feel me in ur tummy remember? ;)
Shane: That was so fucking hot.
Shane: Also fuck you - I’m turning my phone off until I can get out.
Ilya: LOL
(eleven minutes pass)
Shane: In the bathroom.
Ilya: Alone?
Shane: Yeah.
Ilya: [Incoming Call…]
_ _ _
Shane: Good evening, Mr. Rozanov. Thank you for choosing our resort for your stay this weekend. Unfortunately we are no longer able to fulfill your request.
Ilya: What is this. You are forwarding me something?
Shane: Due to unforeseeable circumstances we will have to cancel your stay with us. We hope you understand!
Ilya: Hm. Where was I staying?
Shane: Bali
Ilya: For how long?
Shane: Three nights and possibly an additional day because you really liked the resort package and also the pina colada at the swim up bar
Ilya: I see
Ilya: This is unacceptable
Ilya: You will need to compensate me.
Shane: Of course! Your account has already been fully reimbursed.
Ilya: Not good enough
Ilya: Who am I speaking with
Shane: My name is Shane, sir.
Ilya: I was promised beautiful views Shane. You will have to show them to me now instead.
Shane: I don’t know what you mean. What would you have me do?
Ilya: I think you know.
Shane: Surely you’re not suggesting what I think you’re suggesting.
Shane: That’s extremely inappropriate, Mr. Rozanov.
Shane: They’ll fire me if they find out.
Ilya: I come to this business for a service. If your owner does not serve me, then you will
Ilya: Now let me see you Shane
Shane: [One New Photo]
Ilya: They have handsome face like yours working phone? Waste. Just like how you waste my time now.
Ilya: Give me something better.
Shane: Better…? What do you suggest?
Ilya: Something worth my time.
Ilya: Shirt off. Mouth open. Tongue out.
Shane: Are you being serious?
Ilya: You will provide compensation you said
Shane: [One New Photo]
Ilya: Good boy. You look delicious like this. More.
Shane: I don’t know what to do.
Ilya: Yes you do. You are already imagining my cock filling ur mouth yes?
Shane: Oh fuck.
Shane: Yes sir.
Ilya: Where else could I put it hm? Another place tight and warm.
Shane: [One New Photo]
Shane: Like here?
Ilya: Exactly there. Fuck you are gorgeous. You must know this.
Shane: Yes sir.
Ilya: You are here to serve me aren’t you
Shane: Fuck yes.
Shane: Yes sir.
Ilya: Get somewhere private. I’m calling in thirty seconds.
Ilya: [Incoming Facetime…]
(one hour-long call later)
Shane: Wait should we actually go to Bali or something?
Shane: I’m pulling up the calendar.
Shane: What the fuck is "Suckfest With Marly" on the 17th
_ _ _
Shane: Okay where did you put it this time?
Ilya: Where did I put what 🤔
Shane: Ilya you can’t keep hiding it every time you leave for a couple days. It’s childish.
Shane: And mean.
Ilya: Oh no. Are u already hard baby? Can’t find your toy?
Shane: Where is it.
Ilya: Be patient. I will be home Saturday to fill u up how u need.
Shane: Tell me where it is and I’ll send pics.
Ilya: No u won’t.
Shane: I’m wearing the black jockstrap with the red trim. Put it on especially for you.
Ilya: Bottom shelf in garage
Shane: Seriously? What the fuck is your problem.
Ilya: ❤️
Ilya: Picture
Ilya: Shane
Ilya: Hello?
Ilya: Asshole.
ilya railing the life out of shane with his hand around shane's throat while grunting, "take this fucking cock, hollander. good boy, good fucking boy" and shane is laying there making this face cause he's so fucked and blissed out:
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Shane and Ilya being so desperate after time apart (for whatever reason you want this is a horny post) they end up fucking on the floor by the door. Shane on his back legs wrapped around Ilya’s hips, nails digging in in, dragging down hard to leave marks, shaking and gasping into Ilya’s neck grunting about “harder harder need to feel it” like Ilya isn’t currently trying to fuck him through the floor. Then after sprawled out and messy, sweat and cum on them, Shane sprawled on top of Ilya, panting and laughing about the fact Ilya’s suitcase is still by Ilya’s foot, the front door not even fully clicked shut, loosely on the latch. Ilya still has his shoes on. Ilya sees the carpet burn on Shane’s back when they finally make it up to the shower and apologises but Shane is just like hmmm. I don’t mind it and Ilya is like oh you freak- all eyebrows and they are making out again hot and all tongues
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shane loves how deep ilya can get inside him with his cock. he loves when ilya is fucking him hard and fast but even more so when ilya is cumming because he snaps his hips up against shane's ass and keeps himself buried inside as he unloads into shane, and shane can feel the entire length of his cock occupying the space in his body. in addition to the feeling he loves visualising how deep ilya has gotten. if he could see into his body from the outside maybe ilya's cock would be buried halfway through his torso. spearing him like a thing. a toy. just a perfect glove for ilya's perfect dick.
At night, in the dark, under his covers, behind a locked bedroom door and a double dead-bolted front door, after checking FindMy three times to triple check that his parents are still in a different city and not somehow on their way to his apartment. His dildo is also there.
Places Ilya initiates sexting
The locker room
On a run
His home shower
The club
Brunch with Svetlana
The Porsche dealership
Lifting weights with cliff
While taking a shit
In the back of an uber
On the other side of the room
The MLH awards
During a live interview
While watching men’s gymnastics
In the refrigerated aisle while trying to decide between brands of yogurt
shane laying facedown on the dock at the cottage, soaking up the sun, and ilya walks up to him to tug his swimsuit down and kicks his legs apart to look at his hole. he goes into the water. shane stays exactly how ilya left him.
the tpe cottage is so Real to me. you understand. they could have had guests over and it wouldn't have mattered. if ilya wants to see shane's hole, he does. if he wants shane to spread his legs and stay with his hard dick pressed against his towel, suddenly aware of the sweat covering him in a way that sunbathing usually distracts him from, then he does. and when ilya comes back, he might decide to take shane's swimsuit with him. maybe he'll just tell shane that he's doing him a favor- after all, he has so many photoshoots, surely it'll be easier for them if he doesn't have tanlines? and shane will lay there and let him, floating blissfully.
oh i didnt know people would be interested i just thought it was sillay how it sounded together. but umm... met gala afterparty private bathroom they're both drunk and probably on a little coke or something and connor is hungrily pawing at hudson's crotch and practically begging to suck his dick. hudson is like hesitant bc connor is his boybestie and they haven't fooled around in months so it feels new all over again and weird (he's trying to ignore the girlfriend shaped elephant in the room-- they both are). he eventually lets connor slip his hands under his shorts while kissing at his neck and-- are those tears? why is connor crying? he was just begging to suck him and now he's crying?
he watches as connor sinks to his knees and starts to mouth at the growing tent through the silk of his boyshorts, eyes wet and pupils blown. hudson's a little uncomfortable, but connor seems desperate for it, so he relents. anything to make him feel better.
it's a pretty messy blowjob-- yet one of the better ones hudson's gotten over the years. there's a feverish passion behind it, and he's always one for passion. connor's pretty teal blue eyes filled with tears as he takes hudson in a single swallow.
again... it's an odd situation to be in, hudson thinks. watching his best friend suck his dick in a sickeningly desperate fashion. like he's clinging onto the moments they have together until they have to return to the real world. hudson feels sick thinking about it. he doesn't want to leave this room, and he knows connor feels the same.
his train of thought is broken by sounds of gagging and saliva hitting the marble tile, miraculously missing the tan of his trousers. connor pulls off, coughing, apologizing. his hand is holding his cock in an iron grip.
hudson smooths a hand through connor's gelled-back curls. "you-- fuck-- you don't have to apologize, connie."
"i do," he sniffles. "i'm such a fucking mess for you, huddy. it's fucked up."
it's as close a love confession as either is able to admit.
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transilya who tells shane hes not going to come inside him while strapping him down and making shane beg and cry for his cum has infected my mind
shane wants it sooooo bad. he wants to see ilya lose control. he wants that hard hard deep deep press of his hips and the hot breath in his ear that means hes finally coming inside him. and he wants ilya to keep going until he does it a second time at least. he wants it to not stop until theyre both overstimulated and it's sloppy enough that it does really feel like ilya has shot off two or three times inside him. but ilya wants to keep just pounding and seeing how frustrated he can get shane before he gives him that. turning off the part of his brain that just wants to chase the feeling on his dick against the strap's base in favour of hard slapping thrusts that make shane's breath and pleas for ilya's load come in and out in gasps.
LEO!!! can fairy!shane ride a fleshlight while ilya uses it? can ilya have a dick piercing that fairy!shane uses to get off while making out with ilya's slit? can ilya use a little bullet vibrator on his dick while fairy!shane straddles the vibrator? can ilya tickle fairy!shane's wings with a feather while fairy!shane humps ilya's nipple?
YES YES YES YES YES YES ABSOLUTELY
oh god now i'm thinking about fairy!shane sitting on ilya's nipple......gently rocking back and forth, fisting ilya's nipple hair. the hard part of ilya's nipple can fit inside of him so he's just feeling it and focusing on the warmth and shape of it and moaning quietly. ilya is asleep while this is happening x
