Rooftop Midnight: Barrett Claims Selena's First

The rooftop smelled like warm tar and a basil plant somebody had abandoned to the elements, and at midnight the city under them hummed the way a laptop fan hummed when Barrett forgot to close seventeen tabs. Barrett, twenty-two and a software engineer who treated lust the way other people treated unread email, dropped onto the faded lounge chair with a bottle of wine so cheap the label looked personally offended. Selena, twenty-one, his neighbor from 4B and the only woman who could make a cardigan look like a challenge, sat cross-legged on the concrete with a paperback she had not turned a page of in twenty minutes.

"You lured me up here to stargaze," she said, "and then you brought a wine that tastes like a nine-volt."

"Atmosphere," Barrett said. "Stars are free. The battery is three dollars. I'm basically philanthropy."

She laughed, bright and bubbly, the sound that had been ruining his focus through the shared wall since she moved in two years ago, already twenty, already an adult with a lease and a library card and an unfortunate talent for standing too close in the mailroom. They had been flirting like it was a hobby they were both too chicken to monetize. Tonight the hobby had teeth.

He poured a splash into two chipped mugs. They each took one cautious sip, made the same betrayed face, and set the mugs down on the ledge, barely touched. Clear-headed. Wide awake. The wine was scenery and they both knew it.

Above them the sky was light pollution with one stubborn star punching through. Selena tipped her head back, throat long in the dark, and Barrett's brain filed a bug report it had no intention of fixing.

"You've been weird all week," she said.

"I've been normal. My normal includes thinking about your mouth during stand-up. And right now. And also yesterday, when you borrowed my screwdriver and said torque like it was dirty."

She went pink to the ears. The book slid off her knee. "Barrett."

"Selena."

"I've never been kissed."

The witty software engineer in him blue-screened for a full second. "You've never—what? You're twenty-one. You annotate novels for fun. There should be a line of men at your door holding consent forms and decent wine."

"I was busy being bookish and terrified," she said. Her voice went small, then braver, the way she got when she decided a sentence was going to happen whether her face cooperated or not. "And I've never had sex. Not once. Not anything that counts. And I've been fantasizing about you taking my first time. Specifically you. On this rooftop, if I'm being humiliatingly honest, which I am, because the star is out and you're looking at me like that and I can't joke it away anymore."

The air between them snapped. Barrett's pulse did something undignified and deeply unprofessional. He nudged the wine farther down the ledge so nobody could blame three sips of battery for the yes already lighting up his whole nervous system.

"Say it again," he said, softer. "So I know I'm not hallucinating my favorite fantasy in unnecessarily high resolution."

"I want you." Selena's hands twisted in her cardigan. "I've wanted you since I was old enough to want anyone, which was after I turned eighteen and not a minute before, and I want you to be the one who shows me. If you want that too. If this isn't just the bit."

"The bit retired about forty seconds ago." He leaned forward, elbows on his knees, and let her see he was serious under the grin. "I want that so much it's embarrassing for a man who debugs payment systems for a living. I've wanted you since you moved in. Adult you. Lease-signing, cardigan-wearing, ruin-my-productivity you."

She laughed, shaky, and the heat stopped pretending it was a joke.

The confession flipped a switch Barrett had been politely not touching for two years of hallway compliments and shared takeout. He sat back, studied her flushed face like it was a pull request he intended to approve with comments, and let the grin go filthy on purpose.

"So," he said, "never been kissed, never been fucked, and your big plan was to ambush me under a sad star with wine that could strip paint. Bold. Reckless. I'm into it. Do you want the gentle tutorial, or do you want me to narrate every filthy thing I'm going to do to you until you laugh so hard you forget to be nervous?"

"Both," she said, and then she squirmed, thighs pressing together on the concrete like her body had filed its own request. "Mostly the second one. God, don't look so pleased."

"I'm a software engineer. Pleased is my only facial expression when something finally compiles." He patted the lounge chair beside his hip. "Come here before I start diagramming this on a napkin."

She climbed up, knees on the cushion, cardigan slipping off one shoulder. Up close she smelled like paper and the lemon soap from her apartment, and her eyes were huge and bright and completely sure. Barrett waited. He was horny enough to power a small server, but he was not going to rush the part where she chose him out loud again.

"Show me everything," Selena said. The words came out bold, almost astonished at themselves. "I mean it. I want the whole ridiculous education. Kissing. Hands. Whatever you do with that mouth you've been threatening me with since March. And I want you to keep talking, because if you go quiet I might remember I'm a virgin and spontaneously combust from embarrassment."

"Combustion is a valid outcome," he said, and kissed her.

It was clumsy for half a second, noses, a startled laugh against his mouth, and then it wasn't. She learned fast. She always did. Her lips parted, shy and then hungry, and Barrett made a noise he would deny in any code review. They kissed like teenagers who had been handed a permission slip and a deadline, messy and grinning, her fingers in his hair, his palm spread warm over the small of her back. She tasted like the one sip of bad wine and something sweeter underneath, and every time she giggled into the kiss he got harder, which was inconvenient and also the entire point.

"Hands," she breathed, when they broke for air. "You can—I want your hands. Over clothes is fine. Under is fine. I'm saying yes. Keep saying things so I know you're still you."

"I'm still me. Horny edition." His hands roamed, respectful and greedy at once, learning the shape of her through the soft cotton dress under the cardigan, the curve of her waist, the swell of her ass when she arched into him with a shocked little oh. "You're shaking."

"Good shaking," she said. "Enthusiastic shaking. Don't you dare stop to ask if I'm sure unless I look unsure, and I don't. I look like a woman who just discovered kissing is a competitive sport and intends to medal."

He laughed into her neck and she shivered so hard the lounge chair creaked. His palm slid up her ribs, over the dress, and cupped her breast. She made a sound like a laugh and a moan had collided in a hallway.

"Okay," she whispered, forehead against his. "Okay, new information. I like that. I like that a stupid amount. Barrett."

"Yeah."

"Be my first." Her voice went breathless and clear, no wobble left in the ask. "Right here. On this lounge chair. I don't want to go downstairs and lose my nerve in a hallway that smells like someone else's dinner. I want you to take me here, under the stupid star, and I want you to want it as much as I do. Tell me you do."

"I do." He held her face so she could see it, the joke dialed down to something hot and steady. "I want to be your first. I want you eager and laughing and telling me yes the whole way. If you want to stop, we stop. If you want more, you get more. Deal?"

"Deal," she said, and kissed him like she was signing it. "Now stop being noble for eight seconds and touch me like you've been thinking about it in meetings."

"I have been thinking about it in meetings," he said, and did.

He eased her back on the lounge chair, the city a muted glow beyond the parapet, and kissed her until the cardigan was a lost cause on the concrete and her dress was rucked at her waist. Her panties were pale and already damp, and when his knuckles brushed them she jolted and laughed, half mortified, wholly turned on.

"That's normal," he said, grinning against her throat. "That's the good kind of data."

"Your dirty talk is a status report."

"You love it."

"I do," she admitted, and spread her knees a little, invitation written in the way her hands fisted in his shirt. "Please. Show me."

Barrett slid down the chair, kissed the inside of one thigh, then the other, and looked up so she could see his face. "I'm going to eat your pussy until you come. First time for that too, yeah?"

"Yes. God, yes. Do it. I want it."

He hooked her panties aside—then, when she lifted her hips with a impatient little huff, pulled them off entirely and tossed them somewhere near the abandoned basil. She was slick and pink and trembling, and the first slow lick made her slap a hand over her own mouth.

"Nobody's up here," he said. "You can be loud. I want the reviews."

"Five stars, shut up, more—"

He gave her more. He licked her open with filthy patience, tongue broad and then pointed, learning what made her hips jump and what made her swear in a voice that did not belong to the woman who color-coded her bookshelf. When he sealed his mouth over her clit and sucked, gentle then firmer, she grabbed his hair and made a sound that was half giggle, half wrecked moan.

"Oh—oh, that's—Barrett, that's not fair, that's—"

"Say if it's too much."

"It's perfect too much. Don't stop. Please don't stop."

He didn't. He worked her with his mouth and two careful fingers, curling just enough to make her eyes fly wide, talking her through it between licks because she had asked him to keep talking. "There you go. Sweet girl. First time anybody's had their mouth on this perfect pussy and you're already soaking my chin. You taste ridiculous. I'm going to do this until your brain reboots."

She laughed, breathless, and the laugh broke into a gasp when he sucked again, steady, devoted, a little mean in the best way. Her thighs shook around his ears. Her free hand scrambled for the chair arm. "Something's—I'm—I think I'm—"

"Let it happen. I've got you. Come on my mouth. That's it."

She came with a shocked, bright cry, hips rocking, the orgasm rolling through her so hard she laughed in the middle of it, overwhelmed and delighted and completely gone. Barrett stayed with her until the shakes softened, kissing her thigh, murmuring nonsense praise while she stared at the sky like it had personally betrayed her by being less interesting than his tongue.

"That," she panted, "was illegal. That should require a license."

"I'll laminate one." He kissed his way back up, letting her taste herself on his mouth, and she kissed him back with new greed, nervous energy sparking into boldness. Her hand found the front of his pants and froze, then pressed, curious and eager.

"My turn," she said. "I want to try. I've never—obviously—but I want to. Tell me if I'm terrible. Be funny about it so I don't die."

"You're not going to be terrible. You're going to be enthusiastic and a little clumsy and I'm going to lose my mind anyway." He sat back against the chair, undid his belt, and freed his cock, already thick and flushed and leaking at the tip. Her eyes went wide. Then she grinned, wicked and shy at once.

"Okay. Wow. That's a lot of software engineer."

"Selena."

"I'm nervous and excited, which is my brand." She wrapped her hand around him, experimental, and he groaned. Encouraged, she leaned down and took him into her mouth.

It was clumsy. She went too fast, gagged a little, pulled off with a laugh that was more thrill than shame, and tried again, slower, tongue learning the shape of him while her hand worked what she couldn't fit. Barrett's head hit the cushion. His hand settled in her hair, not pushing, just there, and the sight of her—cardigan gone, dress bunched, mouth stretched around him, eyes flicking up to check if she was doing it right—nearly ended the lesson early.

"Easy," he managed. "You don't have to take all of it. Use your hand. Flatten your tongue. Fuck, just like that. You're a natural menace."

She hummed, pleased, and the vibration made his thighs tense. She bobbed, messy and eager, spit shining on her chin, occasionally pulling off to breathe and giggle and say, "Is this okay? You look like you're buffering," before sinking down again with more confidence. Barrett lasted as long as pride allowed and then gently eased her off, chest heaving.

"If you keep going I'm going to finish in your mouth, and I have other plans that involve actually taking your virginity before I embarrass myself."

"Those are good plans." She wiped her mouth with the back of her hand, eyes bright. "I want that. I want you inside me. Missionary, I think? I want to see your face. I want my legs around you. And I want you to go slow until I say otherwise, and then I want you to stop being careful in the fun way. Yes. Explicit yes. Enthusiastic yes. The yes with footnotes."

"Footnotes received." He dug a condom from his wallet—he was horny, not stupid—and rolled it on while she watched like it was the best documentary of her life. Then he settled over her on the lounge chair, the night air cool on his back, her body warm and open under him. He notched against her, slick and ready, and held still. "Breathe. Tell me."

"I want you," she said, wrapping her legs around his waist, ankles crossing at his lower back, pulling him in with a determination that made his vision blur. "Take it. Be my first. Now."

He pushed in slow. She was tight, incredibly tight, and her breath hitched, fingers digging into his shoulders. He stopped halfway, kissing her jaw, her mouth, murmuring until the pinch in her face eased into wonder.

"Okay?"

"Okay. Full. Weird. Good weird. More."

He sank the rest of the way, buried to the hilt, and they both made sounds that were not dignified. Her legs locked around him. He stayed deep and still, letting her adjust, forehead against hers, grinning because he couldn't not. "Hi. You're not a virgin anymore. How's the customer experience?"

She laughed, and the laugh squeezed around him so perfectly he swore. "Five stars. Move. Please move. I want to feel it."

He did, long careful strokes that grew surer when she met them, heels digging into his ass, her moans tumbling into giggles whenever the chair squeaked like it had opinions. He fucked her in missionary with her legs wrapped tight, kissing her through it, one hand braced beside her head, the other sliding between them to circle her clit because he was greedy for her sounds. She gasped his name. She told him yes, harder, there, don't stop, and he gave her all of it, the slide of his cock opening her again and again while the city pretended not to listen.

"I want to try something," she said, voice wrecked and delighted. "I want to ride you. The—the backward one. So I can control how deep. So I can watch you go inside me. Is that allowed in lesson one?"

"Lesson one is a buffet." He pulled out carefully, rolled onto his back on the wide lounge chair, and helped her straddle him facing his feet, hands steady on her hips. "Reverse cowgirl. You set the pace. You watch. If it stings, you lift off. I'm not going anywhere."

She reached down, lined him up with clumsy determination, and sank onto his cock with a long, shaky moan. From this angle she could see everything—the way he disappeared into her, inch by inch, her body taking him—and the sight punched a laugh out of her that turned into a groan.

"Oh my God. I can see it. Barrett, I can see your cock going into me."

"Yeah you can." His hands stroked her thighs, her ass, not steering, just worshipping. "Take what you want. Use me."

She did. She rose and fell, shallow at first, testing, then deeper when the stretch melted into heat, controlling every inch, watching him vanish inside her with fascinated, filthy delight. Her ass bounced against his hips. Her hands braced on his thighs. She found a rhythm and rode it, giggling when she went too fast and moaned when she got it right, and Barrett held on by his teeth, praising her in a voice gone rough.

"Look at you. Riding me like you invented it. Such a good girl. Taking every bit. You feel insane."

"I feel—" She ground down, clit rubbing against the base of him, and her second orgasm came up fast and bright. "I'm gonna—again—oh—"

"That's it. Come on my cock. Let me feel it."

She came shaking, laughing and moaning at once, clenching so hard around him that Barrett's control snapped clean in half. "Selena—I'm close—where do you want it?"

"On me," she gasped, still riding the aftershocks, giggling through them. "On my tits. I want to see. Pull out. Yes, yes—"

He helped her off, ripped the condom away, and she turned, dropping to her knees beside the chair with her dress dragged down and her breasts bare, eyes sparkling, mouth open on a moan that wouldn't quit. Barrett stroked himself twice, three times, and came hard across her tits, thick stripes painting her skin while she giggled and moaned through the tail of her orgasm, one hand between her own thighs, shameless and radiant and brand new.

They caught their breath under a sky that had not improved and did not need to. Barrett found the thin blanket they kept in the rooftop bin for cold nights and wrapped it around both of them, tugging her in against his chest, her cheek sticky-laughing against his shoulder, his heartbeat finally remembering how to be a normal human rhythm.

"This rooftop," Selena announced, voice hoarse and happy, "is my new favorite place on Earth. Officially. I'm putting it in my contacts."

"Your first time," Barrett said, kissing her hair, "just became my best time. I'm putting that in my performance review."

She snorted, then winced in a pleased way when her thighs reminded her what they had done. "My legs are traitors. They're shaking. I give them ten minutes before they unionize."

"Ten minutes, then my apartment," he said. "Round two. Actual bed. Better lighting. I'll even pretend to be a gentleman for the elevator ride."

"Lesson number two," she teased, poking his chest, "had better include whatever that thing was you did with your tongue, plus a diagram, plus you letting me be on top facing you so I can watch you lose the ability to form sentences."

"Deal," he said, and they laughed into the blanket, already teasing, already wanting, the cheap wine forgotten on the ledge and the star still doing its one job overhead.

She would never again walk past a lounge chair without remembering the exact second she stopped being afraid of wanting him.