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Rooftop Deadline

6 min read

The city lights glittered like scattered diamonds far below us, but all I could see was Elena’s sharp green eyes pinning me against the rooftop ledge. My new boss had dragged me up here after hours under the excuse of reviewing quarterly projections, yet the way her tight black pencil skirt hugged her hips and her crisp white blouse strained over full, firm tits screamed something else entirely. Tension crackled between us from the first second she hired me; now, alone with the wind whipping her dark hair across those high cheekbones, the desire felt thick enough to choke on.

“You’re staring again, Marcus,” Elena said, voice low and clipped like she was issuing orders in the boardroom. She stepped closer, heels clicking on concrete, close enough that I caught the warm vanilla scent of her skin mixed with the cool night air.

“I can’t help it,” I admitted, pulse hammering. “You’re… distracting as hell, Ms. Voss.”

She laughed once, short and husky. “It’s Elena up here. And you’ve been distracting me since your first day. That cocky little smile every time you hand in reports. Makes me wonder what else that mouth can do.”

Her words hit like a spark on dry tinder. Before I could answer, she grabbed my tie and yanked me into a fierce kiss. Her lips were soft but demanding, tongue sliding against mine with zero hesitation. I groaned into her mouth, hands finding her waist, pulling her tight body flush against me. She felt incredible—curves in all the right places, heat radiating through her clothes.

Elena broke the kiss just enough to whisper hot against my ear, “I need this. Right now. Don’t you dare hold back.”

My cock was already straining against my slacks. She noticed, palming me roughly through the fabric. “Fuck, you’re big,” she murmured, squeezing. I spun her around so her hands braced on the wide concrete ledge overlooking the glittering skyline. The city hummed far beneath us, distant car horns and wind the only sounds besides our ragged breathing.

I dropped to my knees, shoving her skirt up those long, toned legs. No panties—just a smooth, shaved pussy already glistening with arousal. The sight made my mouth water.

“Elena… you’re soaked,” I said, voice rough.

“Then taste me,” she ordered, pushing her ass back toward my face. I buried my tongue between her slick folds, licking her swollen clit in firm circles. She tasted sweet and tangy, her juices coating my lips as I sucked that sensitive nub. Elena moaned loud, the sound echoing off the rooftop walls. “Yes… just like that. Deeper, Marcus. Eat my pussy like you mean it.”

I slid two fingers inside her tight heat, curling them against her front wall while my tongue flicked faster. Her thighs trembled. She reached back, gripping my hair, grinding against my face. “Oh god… I’m gonna cum already. Don’t stop—fuck!”

Her body seized, pussy clenching hard around my fingers as she came with a sharp cry. Wetness flooded my tongue. I kept licking through every shudder until she was panting, legs shaky.

She turned, eyes wild with lust, and pushed me onto the low metal bench nearby. “My turn.” Elena unzipped me with impatient hands, freeing my thick cock. It sprang up, heavy and veined, pre-cum beading at the tip. She licked her lips. “Look at this gorgeous dick. I’ve been thinking about it during every meeting.”

She sank down, taking me into her hot mouth in one smooth glide. The wet heat was insane. Elena sucked me deep, throat relaxing as she swallowed almost every inch, nose brushing my stomach. Saliva dripped down my balls while she bobbed, humming around my shaft. The obscene slurping sounds mixed with the wind.

“Shit, Elena… your mouth feels perfect,” I groaned, threading fingers through her silky hair.

She popped off with a gasp, strings of spit connecting her swollen lips to my glistening cock. “I want it inside me. Now.”

I pulled her onto my lap, facing the city. Her skirt bunched at her waist as she straddled me. Elena gripped my cock, rubbing the fat head along her dripping slit before sinking down slowly. We both moaned as her tight pussy stretched around me, inch by inch, until I was buried balls-deep in her velvet heat.

“Fuck, you’re filling me so good,” she gasped, forehead against mine. Her inner walls fluttered, adjusting to my size.

She started riding me hard, tits bouncing inside her half-unbuttoned blouse. I yanked the fabric open, sucking one stiff nipple into my mouth while palming her juicy ass. The slap of skin on skin rang out over the rooftop. Every downward thrust made her clit grind against my base, her slick juices coating my thighs.

“Harder,” she demanded, nails digging into my shoulders. “Pound my pussy, Marcus. Make me cum on your cock.”

I thrust up to meet her, gripping her hips, driving deep. The bench creaked beneath us. Her second orgasm hit fast—she arched back, mouth open in a silent scream, pussy spasming wildly around my dick. The rhythmic squeeze pushed me over the edge.

“I’m gonna cum,” I warned, voice breaking.

“Inside me,” Elena breathed, still grinding through her climax. “Fill me up.”

I exploded, thick ropes of hot cum pulsing deep into her clenching pussy. She milked every drop, riding me slower now, savoring the wet, messy warmth leaking between us. We stayed locked together, breathing hard, city lights twinkling below like silent witnesses.

After a long minute, Elena kissed me softly, a rare gentle smile curving her lips. “This doesn’t change your performance review, by the way.”

I chuckled, still buried inside her. “Wouldn’t dream of it, boss.”

She nipped my jaw. “Good. Because we’re doing this again next deadline.”

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