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Your First

Summary:

You're at a gay bar looking for a rebound when you meet Casey.

You're pinned to his bed when you realize he's a boy.

Notes:

(See the end of the work for notes.)

Work Text:

You'd just broken up with your girlfriend of two years when you first met Casey. You were at a gay bar, letting the too-loud music drown out your thoughts. It wasn't good music, but the bass made your toes tingle through the floor, and that's the best you could ask for at the time.

You looked over at the bar from where you perched, and watched a skinny girl with a black undercut approach. She was kinda cute, in a boyish way. You weren't usually a fan of butch girls, but you could definitely dig someone more in-the-middle like her. Dressed androgynously, with a lip piercing and dark, brooding eyes. Eyes that lit up when she realized you were staring at her. She bought two drinks, carried one to you.

"Hey," you could barely hear her voice, but you had a knack for reading lips. She sounded a bit hoarse, you knew, but you weren't about to back out just cus of a sore throat.

"What's your name?" You asked, testing the waters for now. You noticed her look at your wrist before answering. Your lesbian flag band was easy to make out, even in the dim light. She smiled, pleased by what she saw.

"I'm Casey!" Her fingers were long, and lingered on the cup she handed to you. Her nails were painted baby blue. Trimmed short, good.

"Wanna go outside?" You drained the cup quickly, taking big gulps. You'd come here looking for a rebound anyways.

"My apartment is across the street," she gestured with her hands as she talked. "It's small, but I live alone. We'd have the place to ourselves."

You finished your drink, let her grab you by the sleeve and pull you carefully through the crowd to the door.

In the light of the apartment's hall, she looked a little more masc than you first realized. Her shoulders were broad, her hands rougher than expected. You wondered if maybe she was trans trans. You hadn't dated a trans girl before, but you wouldn't be opposed. Then again, the thought of touching a dick... Actually, while it would have made you cringe usually... Right then, after that drink, you felt a little more open to it.

Casey's apartment set off a couple more alarm bells. It was sparsely decorated, with pizza boxes on the counter and a hamper full of laundry blocking the hallway. You noticed all the clothes in the basket were dark-colored men's clothing. Nothing like the light, breezy clothes Casey was dressed in.

Inside the bedroom, there was only a bed, a bookshelf, and a desk with a PC. The PC monitor was dark, so you couldn't glean anything from it. Not that you needed to.

You sat on the bed, uneasiness creeping in. Casey sat beside you, put a hand on your wrist. Her fingers wrapped around your bracelet. Twisted it until the flag was facing inside, then released it to return to its original shape. You knew something was wrong then.

Casey's voice was deep, now that you were away from the booming music. "Am I your first boy?" His voice made you squeeze your thighs together. You hadn't known... No, that wasn't true. You'd suspected it the entire time you were walking. Since leaving the bar, he'd been silent, only gesturing with his hands for you to follow. You'd watched him leer at your low-cut top, watched the way he licked his lips.

He wasn't trans. He was a boy. And you, a lesbian, had just followed him into his bedroom like a puppy.

"Is that a yes? Don't worry, I'll be gentle~" He slid his hand along your forearm, and slowly, carefully, pushed you onto your back. You let him pin your wrists, let him climb atop your lap. He was shorter than you. Skinnier. If you really wanted him to stop, you could probably make him. So why didn't you?

Casey's lips met yours, and you whined. He used his knee to spread your thighs, rubbed it against your frustrated clit. You gasped against his mouth. He kept going, pressed his tongue past your lips. It was hot and slimy, and moved expertly. You wondered if he would use it on your pussy, too. The thought made you so wet.

He stretched your bracelet, slipped your other wrist through it, used it to cuff your hands together. He held them above your head with one hand while he used the other to explore your body. He kissed you between heavy breaths, murmurs of praise. "Good girl. Open up for me."

You tilted your head back, and his lips found your neck. His hands pushed your sweater up, slid crudely under your bra. The wire bit your sides as it deformed, but you didn't stop him. He squeezed tight, ran his rough palm over your nipple. His baby blue nails dug into your skin, left crescent moon depressions in your titflesh. "Ahn! Hahhh...!" It hurt, it hurt, it felt so good.

Casey bit your neck as his hand abandoned your chest, leaving it aching. He slid his palm over your stomach, down to your jeans. He unzipped your pants. He tugged them down your thighs. He was so slow, so meticulous. He was doing it on purpose. You whined his name. "Casey! Casey!" That made him speed up.

The next thing you felt was his dick against your mons. You hadn't shaved, almost never bothered. He didn't either. Your arms strained as he slid his cockhead up and down between your clit and your navel. A trail of precum, sticky and shimmering, followed. You were aching for him to stick it inside. You tried to buck your hips, and he pressed his hand against your stomach, pinned you down like an animal in heat.

He denied you, made you wait, and you broke easily. Tears filled your eyes and you begged. "Please! Please put it in me, I can't take it!"

"But you're a lesbian," he crowed. "And I'm a boy~" He was so hot. You were a dyke. But...

"Please. I don't care. I'll be whatever you want me to be, just put it in."

He didn't. Instead, he used his hand. Grinding his palm over your clit, he brought you to the edge. His fingers skirted over your pussy lips, leaving your insides desperately empty. You groaned and whimpered and begged more, but he still made you wait.

"Be a good dyke and wait," Casey kissed your chest. He finally unclasped your bra, let your heaving breasts spill out properly. You had a painful red scratch on the side of your ribs, from how he'd ruined your bra. He kissed it, sending a shudder through you. Then he kissed your breasts, your collar, your nipples. Between the fingernail bruises. Between your cleavage.

You couldn't bear it any longer. You came from the combined stimulation of his kisses and the palm on your clit. Your body crumpled up, buckled. You tried to roll up in a ball, tried to defend yourself from the overwhelming touch. But Casey didn't let you. He used his hands to hold you flat to the bed, used his lips to draw more desperate, overstimulated cries from your lips.

You had lost. Utterly lost yourself to his dick without ever feeling it inside you. He'd broken you so easily.

"So much for being a lesbian, I guess." Casey laughed cruelly as he finally, finally stuffed his cock inside your aching, hungry hole. Your walls clenched tight, throbbed against his thick shaft. It was the best thing you'd ever felt. You cried as Casey thrust into you, again and again, bringing you more pleasure than your ex-girlfriends ever had.

He didn't stop until you'd cum four times, and he'd pumped two thick, creamy loads inside you. You weren't on birth control. Obviously. You were a helpless dyke, pinned to the bed by a prettyboy with a cock the size of a beer can. He'd fucked you beyond your breaking point, fucked you so hard you didn't even consider pretending you didn't want more.

"Y-your phone number," you begged as he zipped his pants up.

He shook his head.

"Please. Nobody else..." Nobody else could compare. Nobody else could fuck you so perfectly. You crawled onto the floor, legs sore, and pawed at his waistband. "I'll suck your dick. Please. Just tell me your phone number. I need to see you again."

Finally, he caved in, though he didn't let you suck him off. "Next time," he ran a hand through your hair. "If you're still wearing that pride bracelet, I'm not gonna hold back." That had been him holding back. That had been "gentle."

You wore the bracelet next time.

Notes:

I hope you enjoyed this! I was a little worried Casey would come across as a 'trap' stereotype. I think a little of that is unavoidable when working with mistaken gender stuff. But I hope you understand that he isn't inspired by transphobia! (Just a little in-character lesbophobia, like you signed up for.)