TransMasc!Reader x Retired!Simon Riley
Contains (eventual, this chapter): Emotionally unavailable Simon, angst, SMUT, Simon as a hard!dom, Use of “pup”, “lad”, “mutt”, “sir”, “prince”, whatever the opposite of slow burn is, awkward!TransMasc!reader, gender confusions, masturbating, age gap dynamics (Simon is 42, Reader is 22), slight forcemasc vibes?, NOT PROOFREAD, and more to come. ;)
Dating apps fucking sucked. That was the general consensus as you swiped aimlessly, all the men on your screen either repulsive-looking or had something akin to a hate crime written in their bio.
Don’t you just fucking love Englishmen?
You were about to close the app and give up on the prospect of love and everything it stood for before a man caught your eye.
Simon. 42. His face conveniently covered in every photo, either by the phone or a plain piece of black cloth. Photos of his toned abs dominating his profile. Only a few sentences written in his bio.
“Searching for a little lad to throw around ;) Not good at commitment. Picky. 👻”
The ‘picky’ comment was a bit discouraging, but you truthfully had nothing to lose. Maybe a bit of ego, but even that was scarce nowadays. You swiped right, expecting nothing and —
Did it just fucking match?!
The desperate part of you was jumping for joy, but the sensible part of you was clearing your throat and planting your hips firmly in bed as to not bounce off the walls. Despite the time,
You typed up a message anyways. Unfortunately, Simon beat you to it. Cockiest bastard you’d ever matched with on this godforsaken app.
“Was waitin for u to match w me, knew u would”
Okay, ego alert. You snorted, with a complimentary eyeroll, before typing up a quick response.
“Oh, you’re so sure of yourself?”
“Nah just sure of u. i know ur type, pup.”
You wanted to scream. Out of annoyance, out of excitement and a little bit out of fear. You hadn’t even told him your last name, and he was already belittling you and pinning little pet names to you.
“Excuse me?! What the hell does that even mean?”
“Need a big man like myself to protect u”
This guy had a lot of nerve. And probably the qualifications to back up his ego, but still! Give a guy some breathing room.
“What are you even on here for?”
“Wow! You can spell the entire word.”
“Watch it, lad. wouldn’t wanna have to show u who u belong to.”
You audibly gasped. You were sure at this point that this man was either fucking with you, or extremely desperate for some kind of something. The conversation unraveled from there, him sending photos of his gray sweatpants — outlining what it was he was thinking with, and you sending photos of simple things. Thighs, post-workout photos. Anything to keep him wanting. Asking for more.
Maybe this could be something real.
A few weeks had passed, flirty conversations and unfulfilled promises of him doing all kinds of dirty things to you lingering within those conversations. Him sending his number in an attempt to get you off this app.
And right now, you lounging on the couch after an insufferable 7-hour shift at Tesco’s. Narrowly avoiding your manager asking for you to stay over. And Simon’s name flashing across your phone screen, a soft vibration accompanying the image.
He’s fucking calling you!
You picked up way too quickly, any dignity quicker shredded in the wake of this new relationship (could we even call it that?) development. You’d get to hear his voice. After many thirsty images and many nights spent with a soaked gusset, you’d hear the man behind the screen.
He picks up, his end of the line silent for a frozen moment in time before he speaks — the grin he’s wearing evident in the inflection in his voice.
“Hey, pup.” Something akin to a cough rumbles from his lungs and he sighs. “Wanted to hear ya.” You hear a soft zip sound, and it registers with you exactly what this is. What exactly he’s asking for.
“Hi, Simon,” you drawl out, your voice akin to that of a teenage boy, but you push through. He knows your story. Some of it. Why there’s constant red marks on your ribs from your binder, the story of your first awkward packing experience, the trials and tribulations you faced to get here. To become who you are. To become him. He knows it all, and he doesn’t mind. It doesn’t phase him. Encourages him, it seems like.
He laughs gruffly, a thud from him snuffing his cigarette before he has himself in his hand, stroking softly. “Hi, lad. You been good today?” He asks, and normally… this would turn you off. Spark a spite in you to stop taking care of yourself, but it blooms something in your chest. Something soft and warm and dangerous. Something permanent and sticky. Something not easily tamped down.
“Yes, sir,” you smile, voice becoming more timid as Simon gets more bold. He likes you this way, soft and quiet while he does all the protecting. All the instigating. There’s long, focused breaths he’s taking. Surely to keep his composure as the soft squelches grow louder, more rapid.
“How can I know that, lad? You tellin’ me the truth?” He chuffs out, his grin growing larger with every soft giggle you let out. He seems to adjust the microphone, his phone closer to where he’s holding himself in his hand. Like he wants you to hear what he’s doing to the sound of your voice. The squelching a continuous sound, his breathing rough.
“Yes, sir,” you giggle out, your face all splotchy in its flush. He laughs back at you, growing silent for a second before he speaks again.
“You need me to come and show you how to behave anyways, prince?” You flourish at the nickname. Like a flower after fresh rain, sun-bathing and blooming new petals. Even if he’s repeatedly assured you that this is nothing more than fuck-buddies, you can’t help but feel loved. Cared for. Maybe it’s the lack of substantial care as a child, or the lack of any kind of memorable authority figure, but you flourish under his praise. Finally growing into someone important under his ownership.
“Maybe,” you sigh, almost wistfully, and he’s over the edge. Spend lazily shooting onto the concrete of his balcony, next to where the cigarette had been tossed. He’s redone his belt before you can even say his name.
“Address, prince. I need it,” He says, and there’s a soft pleading edge. You hear the rumble of some kind of motorcycle, and type it to him.
“See you soon, Simon,” you sigh again, a whimpered lilt at the end just to be a fucking tease.
“Damn right you will,” and the call is cut.
The knock is firm. Intense. Knowing. Ready.
You open the door, mouth widening as you take him in (with your eyes). Your eyebrows furrow, and he’s on you. Motorcycle helmet and balaclava tossed lazily on your counter, shoes tossed somewhere socially appropriate, and his arms caging you in against the wall. You catch a glimpse of his face here, but everything is moving too quickly to be registered.
His hips rutting against your stomach as he completely fucking dominates your mouth, spit covering your face in a way that isn’t typically possible when kissing anyone else. But Simon had something to prove. Something he wanted to show you.
You make a soft whimper, pushing on his abdomen to hopefully slow down this seemingly immovable object, and he takes a step back. All too abruptly. You whimper at this, too, and he sighs.
“Bedroom.” He snaps, his voice low. You nod, leading him there. You stand in the doorway like a moron before he all but snatches you up and tosses you onto the bed, finding hems to clothing and snatching. You try to close your thighs, slow him down at all but this is now a mission to him.
And you always have to complete the mission.
Once you’re spread out for him on your messy bedding, he looks at you. Still fully clothed to keep a distance. Uphold the dynamic he has created here. But mostly to keep the distance. He wants nothing more than a warm body out of this, but why is it so hard to keep reminding himself of that? When you’re giggling or sending him photos of pastries that’re just too damn sweet to be healthy? Or photos of your orange tabby?
Why is it suddenly so hard to create distance?
But he manages, grabbing at your clit and twisting. He tuts softly, shaking his head.
“Tiniest prick ‘ve ever seen,” he scolds, and it knocks you from your turned-on trance. Did he just..? “Can’t even see it until I start playin’ with it, strokin’ on it,” You are majorly confused, but just lay back and try to enjoy the action. You’ve been lacking in that department, why ruin a good thing? Plus, it’s probably just a weird sex thing. Nothing to worry about.
He gets his mouth on the sensitive nub, now red and swollen from stimulation, and you’re bucking your hips and whining.
“Enough, pup,” he snaps up, his eyes boring into you. He firmly plants hands on your pelvic bones, pressing you down into the bed. “If ya can’t fuckin’ be still, you’re gonna piss me off. N’ ya don’t want that.” And as much as you wanted to be a brat, his eyes and his tone scared the piss out of you.
He ate you until you finished thrice over. Wanted to go for a fourth but you whined too much. It was 9:43PM by the time you had cleaned yourself up and redressed yourself. Finding him getting his things ready by the door after rinsing his face with water.
“Si! Don’t you want to stay?” Your tone broke your own heart. Suddenly, you were five again. Asking your mom to come to a dance recital that she was too drunk to even write on the calendar. Empty promises that she would make it, and yet her seat sat vacant. The spot you begged your teacher to —
“Can’t do that, pup. I work construction. Gotta be up early.” His voice breaks you from the trance. Tears gathering at the brim of your waterline as he looks down at you, his face shielded now with the balaclava. He’s off tomorrow, but you don’t know that. You can’t. He can’t tell you. Can’t stay. Doesn’t want to leave.
He has more he wants to say, festering on the tip of his tongue like molasses. Sticky and immovable. So he just shakes his head, grabbing his helmet and rocking on his feet. He wants to kiss your temple, and give you more comfort. But he’s already waded in too far. Told you he couldn’t fuck you ‘cause he didn’t bring a rubber, but what he didn’t say was he couldn’t guarantee he would pull out at all.
He’s gone, and you’re tearing up. Feeling barely an inch tall. Begging your stepdad to watch cartoons with you, but he’s too doped up to walk straight. Promises for ‘next time, bug.’ A next time you never got.
Simon asks, still in the parking lot of your building.
You respond, because that’s the most honest truth. And he understands. You’re both standing on different sides of the river, and it’s just too cold to swim over.
