Archive of Our Own ^beta

Chapter Text

Matt enters the kitchen in search of a refill for his boyfriend. He spots the large punch bowl pretty quickly and heads over to it, giving a quiet ‘excuse me’ as he slips past the only other person in the kitchen. He doesn’t pay them much mind.

As he finishes ladling the drink for Alex the other person in the kitchen says something to him.

“Hey Matt, can I ask you something?”

He turns around still holding the drink, and realises the other person in the kitchen is the party host, Alison. They’re at her parents place, her stepfather is pretty rich Matt’s heard. Her parents are out of town right now, which is why Alison is getting away with hosting a college party here, but Matt doesn’t really care about the specifics. It’s not going to be his head on the chopping block if anything is broken, and he and Alison aren’t close. He’s only here tonight because Alex wanted to come, Alex has been trying to stay connected to his old friends since coming out as trans, but most of them haven’t been all that accepting. Alison included. Which kind of pisses Matt off, if he’s being honest, but he keeps things polite, for Alex’s sake.

“Sure, what is it Alison?”

“What would you say if I told you Caitlyn was super into you? Would you do anything about it?” Alison tilts her head to the side as she says it.

“I’m gay.” Matt means to say more but he’s just so shocked by Alison’s question that that’s the first thing out of his mouth. His sexuality is a known fact among the group. He realises he’s left the words hanging like that and quickly goes to add more.

“She knows that, you know that. Everybody does. She’s a nice person, but it just isn’t happening.” He tries to keep the offense from his voice, reminding himself he’s trying to keep the peace. For Alex.

“But I mean. You’re really into Caitlyn though.” She replies.

Something about the words feel like they have a force behind them as she says them, and something shifts in his head as she speaks, but he forgets as soon as she finishes talking, in the span of a blink.

He blushes and scratches the back of his neck bashfully, “I mean yeah. Weird as that is considering I’m only into guys usually, but I’m with Alex. I’m not gonna cheat on him obviously.”

“Yes you are.” She gives him a falsely serene smile as she steps into his space.

“Huh?” He manages to get out before she meets his eyes. He finds he can’t look away as she begins to speak.

“You never started dating Alex, you’re single right now and can’t get Caitlyn out of your head, you’re head over heels for her. You’ve been thinking of getting with her for a while now. You’re finally gonna do it tonight.”

Yeah he’s been wanting to ask out Caitlyn for a while, he’s really, really into her. He’s probably been hesitating because it’s the first time he’s ever been attracted to a woman. And he’s kind of confused about just how strong his feelings are, they’re more intense than most of his crushes on guys have been. He’s kind of wondering if that means something for his sexuality, like maybe he might be bisexual.

“In fact you’ve been single since forever, you’ve never dated anyone. All the crushes you’ve ever had have been on girls in your friend groups, not on guys. And you’ve never slept with a guy either, only a couple girls since starting college.”

Right all of that was true, he was nervous about asking out his first girl. He’d never gotten up the courage before. But he’d had an easier time with sleeping with them a few times now. He-

“You’re as straight as they come, never looking at another guy with the slightest bit of lust, only women. When people ask if you’re gay you’ll laugh it off like it’s a funny joke, because it is.”

Alison’s smile has become distinctly cruel but Matt doesn’t know why. They’re just talking about… Well he’s just listening to her say things that are completely true. Why is he listening to her repeat things about him back to him? He was meant to be doing something-

“Now go ask Caitlyn to go upstairs with you to the guest bedroom and make all her dreams come true by fucking her brains out. Then ask her to be your girlfriend. When she says yes you’ll be over the moon about it. You’ll be the most dedicated boyfriend she could ask for. After all, you’re a sweetheart, I know you are.” Alison pats him on the cheek and steps back.

Matt blinks, disoriented for some reason. Why was Alison in his space saying all that stuff? He glances down at her in confusion.

“Off you go! Cait’s in the hallway! Go get her tiger!” Alison urges.

The question slips from his mind, and he promptly forgets about it. He steels his courage as he takes a step towards the door, before noticing he’s carrying a drink. For Alex.

“I was…this was for Alex, I think.” He says, unable to recall the exact line of thought that brought him to the kitchen.

“No worries, I’ll take that to her, sorry, him.” Alison takes the drink out of his hand and walks straight out the kitchen without a backwards glance.

Matt shrugs at the strangeness of her actions and heads towards the hall. He squeezes past several people and through a few doorways and finds himself in the hallway in no time at all. His eyes find Caitlyn within a moment, she’s the most beautiful person there, to him anyway. Like she’s outshining everyone else. As he approaches he notices she speaking to one of their friends, Mia.

They stop talking as he steps into their bubble.

“Sorry to interrupt you both, but I just need to ask Caitlyn something.”

An adorable blush spreads across her cheeks, “What did you want to ask me?”

He glances at Mia, “It’s kind of a private question if you can give us a second?”

Mia’s eyes flit to Caitlyn looking for confirmation before she slowly answers, “Yeah, sure. Talk to you later Cait.”

Matt immediately turns back to Caitlyn as Mia leaves, her eyes moving back up to his as well.

“So what’s the big question? You have me kind of nervous now.” She chuckles.

He leans down to whisper in her ear, her breath stutters in surprise as he moves into her personal space.

“I was wondering if you wanted to go upstairs to the guest bedroom with me.” He says quietly and then pulls away.

Her eyes grow wide and her blush intensifies, “Seriously? And this isn’t like a prank or-? I mean aren’t you gay?”

He laughs lightly, “With the way I feel about you? Not in the slightest, I’d say.”

She looks unsure as he smiles down at her but a smile slowly spreads across her lips, matching his own.

“I…Okay, yeah. Let’s go upstairs.”

He takes her hand and leads her to the staircase. About halfway up he hears wolf whistles from the other people in the hallway but ignores them. Caitlyn hides her face in his side as they climb the stairs together.

She leads the way to the guest bedroom, more familiar with the layout of the house than him.

“We’re really doing this.” She says once they’re standing by the bed, the door closed behind them.

“Yeah, if you want to. I sure do.”

Her light, happy smile causes warmth to spread through his chest.

“Then there’s no time to waste.” She says stepping close to him and lifting a hand to his shirt button.

He let her slowly undo each button sinking down as she does and then coming back up to push his shirt off his shoulders. As she moves down to his fly he puts his hands on her hips, sliding her t-shirt up. She pulls her hands away from him long enough to let the shirt come off and then returns to pulling his jeans down. He steps out of them as they fall to the floor and then distracts her from his underwear by slipping a hand into her shorts and panties. He rubs his fingers up and down her slit, finding her already moist.

Cait shudders, her breath hitching. She runs her hand along his dick through his briefs in appreciation. As she goes to pull his underwear down again he begins teasing her in earnest. Rubbing back and forth, finding her clit and giving that extra attention, pressing his fingers just barely in. Her hands come up to her own pants and rip them off hurriedly. He chuckles and pulls his hand from her panties, moving to pull them down. She steps out of them impatiently, clearly wanting to get to it. He obliges, removing his briefs without further pause.

Her hands find his body as soon as he’s straightened back up, exploring his chest, his hips. One hand finds its way to his hardening dick, giving it a stroke. He hums in encouragement. She gives it a few more strokes.

He decides to return the favour with his fingers finding their way back between her legs, as his other hand grabs her ass to pull her close. He dips a finger inside her pussy slowly, she opens to him with ease and he quickly presses a second alongside it. She moans quietly as his fingers press in, stretching her open in short thrusts.

“Fuck Matt. I want you inside me now, I’ve waited too long already.” Caitlyn whispers.

He lets her manoeuvrer him towards the bed. She pushes him down, down, down until his back hits the mattress. She crawls over him, kneeling above his hips. He's pleasantly surprised to learn she likes to be on top. He admires the view of her body from below as she shuffles into position. She gives his dick a few short pumps before holding it so she can sink down onto it slowly. He groans low in his throat and his hands come up to hold her hips. She throws her head back, moaning in bliss as he bottoms outside her.

He squeezes her hips in silent encouragement as she lifts herself up and thrusts back down, fucking herself on him. She sets the pace real slow at first, and he lets her.  He thrusts up to meet her with each slow gyration of their hips. Once she’s found her rhythm, he slides his hands up her sides until he reaches her chest. He takes her tits in his hands kneading them and tweaking her nipples.

“Caitlyn you’re beautiful you know that?” He can’t help but say.

She looks at him bashfully and shakes her head a little, “Sap.”

She slows, leaning forward to kiss him passionately. Whispering, “Can’t believe this is really happening,” to herself as she pulls away.

“Believe it.” He answers and she looks caught.

He distracts her by thrusting up into her and reaching a hand down to rub her clit.

She trembles and then slowly picks up the pace again, fucking herself down onto him, meeting him as he thrusts up.

When she inevitably begins to tire he asks, “Want me to take the lead for a bit?”

She nods and he flips them over carefully. He kisses her again, more intense than the last, and then lifts her legs onto his shoulders. He lines back up and slams home. She moans loudly at the new angle. One of her hands quickly moves between her legs as he holds her and starts giving her a deep hard fucking. Pulling out fast and thrusting in deep, over and over. She grinds into each of his thrusts with enthusiasm.

“Oh fuck! Yeah just like that, just like that.” She says breathlessly as he pounds into her.

“You gonna cum for me soon Cait?”

She nods vigorously which causes him to speed up, hitting that same angle as before. She moans high and desperate, as her hand rubs quickly over her clit. After several more thrusts he feels her tighten around him and watches her quake beneath him. Moaning his name loud enough he’s sure they can hear it downstairs. He fucks her through it, slowing down as she comes down from her orgasm. He’s pretty close himself but pulls out reluctantly, taking himself in hand to finish off outside her pussy.

Her hand comes up after just a couple pumps to stop him and he glances up to see an eager look in her eye.

“Let me.” She shuffles forward to take his cock in her mouth.

His head falls back as he groans at the feeling of her tongue coming up to tease the underside of his dick. She’s no expert but he was already close to cumming and her tongue teases and licks him as she takes him as deep as she can on each bob of her head. He cums within minutes, warning her just in time to watch her deliberately plunge her head forward to take him as deep as she can, swallowing his load. The sight is a sinful thing.

They cuddle up on the bed after that, basking in the afterglow. She hums quietly, it’s a happy sound. He’s pretty damn satisfied as well, and his nerves a distant thing in this pleasant fuzzy place he’s in. So after a few minutes, he looks over to meet her eyes and asks.

“Will you go out with me? I know this is all out of order, sex first and all.”

Surprise stretches across her features, quickly morphing into joy.

“Yes! Absolutely. I’ve been…well I’ve into you for ages. Been wanting to ask you out but wasn’t sure since…well you said you were gay before today, but then earlier you said…” She looks unsure as she trails off.

“I’m definitely not gay. I’ve been wanting to ask you out for a long while as well, haven’t gotten the courage until now. Maybe it sounds stupid but this made it easier.”

She smiles widely and leans forward a little, “If we’re going out can I kiss you again then?”

He leans the rest of the way in and meets her, kissing her languidly, savouring it. The afterglow has faded, but he feels even better now as he pulls his now girlfriend close, kissing the top of her head with a smile.

Chapter Text

Alex is standing on his own waiting for Matt to come back with his drink so they can continue their conversation when Alison comes over and hands him a drink.

“Thanks?” He says, confused.

“Matt needed a break from all the noise for a minute so I offered to bring your drink over.” Alison explains.

“Oh, thank you then.” Alex says more warmly this time.

“Alex can we…talk? Maybe somewhere quieter?”

With the serious and slightly uncomfortable look on her face he can guess she wants to make amends about how she’s reacted to his transition. How a lot of their friends have. He’d prefer if Matt were with him for this, Matt’s been his rock since he came out several months ago. He was the most vocally supportive of Alex’s friends. And Alex knows Matt actually sees him as a guy considering he asked him out a few months ago. Alex had been crushing on Matt for ages and was super happy when Matt asked him out.

Alex has gotten a few nasty comments since then implying that he’s faking being trans just so Matt will be willing to date him now. Alison herself has even implied it, though not outright said it.

Alex eyes her with some trepidation but he knows things will never get fixed if he doesn’t talk to his friends so he says, “Yeah alright.”

They weave through a few rooms as she leads him to her stepfather’s study. The sounds of the party group muffled as Alison closes the door. Alex has been in here before once or twice, it’s a nice space. Lots of stuff that looks expensive, like the big, varnished wood desk.

“So.” Alison starts.

Alex turns to look at her, meeting her eyes. He immediately feels strangely trapped in her gaze. Like her eyes are boring into him. He tries to look away but can’t.

“Since Matt is probably upstairs by now fucking Cait you obviously can’t be his boyfriend anymore.”

Alex can’t believe Matt would cheat on him like that out of nowhere, he’s breaking up with him first chance he gets. He has half a mind to interrupt them right now even. Alex feels his betrayal threaten to choke him, confused by his gay boyfriend cheating on him with a woman. Does that mean Matt isn’t really gay and never saw Alex as a man in the first place? The thought makes him want to cry-

“You’re not going to be anyone’s boyfriend now or in the future. Because you’ll be their girlfriend, just as you were in the past. It’s time for you to give up this nonsense, I’ve tried convincing you the normal way.”

“Alison w-” He starts but the feeling from her gaze comes back full force before he can fully form a thought.

“You’re not a man, you’re a woman. A tomboy, sure, but you’re not a guy. You realise how silly you’ve been now. You can’t wake up and decide you want to be a boy, it doesn’t work that way, you’ll always be a woman.”

Of course she’ll always be a woman, she understands that now. The things all her friends have been saying are just true, and she’s finally realised that. It’s taken far too long. A kind of quiet despair echoes through her chest at the realisation of the cold, hard truth.

“Every memory you have since starting your transition is now tinged with discomfort and confusion. You weren’t happy for even a second, not when people called you Alex. Not when they called you a guy, or used ‘he’. Hearing people call you ‘she’ again will bring a rush of relief. You’ve missed it, it’s right. It’s comfortable. It’s how it’s supposed to be.”

Why did she struggle through coming out and transitioning for so long when it was so clearly wrong for her? It didn’t feel right at all, but once she’d started she just didn’t stop. Didn’t admit to herself it was wrong.

“You’re going to ask people to go back to calling you Heather. That name feels like you. Alex doesn’t.”

Yeah Heather is definitely the name she wants to go by. Alex just doesn’t fit, never did.

She notices Alison glance past her to the desk, breaking eye contact momentarily but before Heather can speak Alison’s eyes are back.

“Right now you’re going to turn around and find a pair of scissors to cut that binder off you. You can ask to head to my room to borrow one of my bras afterwards.”

Heather blinked and turned around on autopilot, searching the desk for a pair of scissors. She needs this binder off now. And she doesn’t care if it gets destroyed in the process, despite how expensive it was.

She finds a pair in one of the draws and lifts her shirt to find the edge of her binder and start snipping. It takes a bit of effort since the scissors are for paper cutting but she sighs in relief when she reaches the armpit, quickly cutting the shoulder above it so it falls away. She doesn’t even look at the scrap of fabric on the floor, to busy being self-conscious about her nipples being visible through her shirt.

“Hey Alison can I borrow a bra? I don’t really want to hang at the party like this, it’s pretty embarrassing.” Heather asks.

“Yeah sure! You’re lucky my bedroom is down here on the ground floor and pretty close by, I don’t think anyone will notice if we’re quick.”

“Thank you!” Heather says enthusiastically as she follows Alison out of the study and past the crowd of people to Alison’s room.

Heather closes the door quickly, hoping nobody looked at her too closely and noticed she was bra-less.

Alison’s already headed over to her stuff and found a bra when Heather looks over at her. Alison hands it to her and turns around.

“Here you go, I’ll just look the other way for a sec. It should fit, I think we’re a similar size.”

Even with Alison looking away Heather puts the bra on under her shirt. It’s more awkward that way and she finds that Alison’s chest is definitely smaller than her own, so her breasts are barely contained, but she doesn’t complain. She’ll take a bra that’s a little too tight over none. Alison turns back around a minute later.

“Much better! Don’t you agree?” She says with more enthusiasm than Heather feels.

Heather doesn’t really know what she feels, to be honest. Her head is a mess and she has a lot to sort through, but she answers anyway, “Thank you, and yeah I think so?”

Alison frowns at her uncertain answer. Heather feels a little bad but she’s not sure what for. Alison takes a step towards her and catches her eye.

“Heather you’re overjoyed that you’ve finally realised you were wasting your time playing at being a boy. Now you can finally embrace your womanhood and be yourself. You’re kinda masc and there’s nothing wrong with that! Women can have short hair, not really wear much makeup and prefer jeans to dresses. All this time you thought you had to be a man to be more masculine, but you’re just butch!”

It was pretty silly in retrospect, that she thought she needed to be a man in order to keep her hair short. Other people might judge her for being a woman who doesn’t like makeup, but that’s their problem. And it’s not like any of them were any nicer when she called herself a man anyway.

“You’re not just butch, you’re a dyke. A lesbian through and through. You like pretty girls. All your past crushes have secretly been on your closest female friends. To your quiet shame as each of them turned out to be straight.”

Heather blushes as her past crushes come to mind. She’s always fallen for her friends in the past, unluckily for her. She needs to put herself out their and meet some gay women if she’s ever gonna have any hope of dating.

“The memory of your first kiss with Jake that you told me about? That never happened, you kissed your old friend from highschool, Jessica. It was just an experiment for her but for you it awakened your interest in other girls. Since then you’ve known you are a lesbian and never doubted it.”

Heather remembers that kiss vividly. They were both fourteen and nervous to kiss boys without any practice, or Jessica was anyway. Heather wasn’t so sure about boys, and when Jessica kissed her she knew she’d never think about them at all. It was a sweet kiss, unsure and fumbling, but Heather still remembers it fondly, as well as the crush on Jessica that she had for years after that.

“Forget the first time you had sex, with Joseph. Your first time was drunk at your first college party, you were talking to a cute girl while the both of you got drunk. You ended up stumbling into bed together, she rocked your world.”

Heather wishes she had that girl’s number, she still thinks about that night often enough to consider repeating it. But she can’t even remember the woman’s name, and never asked for her number.

“That about does it I think. That talk helped clear things up for you, you told me all your insecurities about transition and how you’ve been making a mistake. You came out to me as a lesbian. You feel more comfortable now that the words are out in the open, and feel confident enough to start sharing them with others. You feel confident in yourself, your identity. You feel happier.”

Heather blinks and something clicks into place, like the world righting itself. She feels lighter, more carefree now. She really needed that talk, to just say all that stuff out loud.

“Thank you for letting me get all that out, you’re a good friend Alison.” Heather reaches out to pull her into a hug in thanks.

Alison pulls back after giving her a squeeze, “Anytime! What are friends for huh? If anyone gives you trouble about all this they’ll have me to answer to yeah?”

Heather can’t help but feel a little embarrassed even as she smiles, “Thanks Ali!”

“Let’s get back to the party then, I bet people are wondering where we are.” Alison says.

Heather nods and they head back out into party. Heather does so with a new sense of purpose as she plans how to tell each of her other friends the news.