First Time Anal With Her Boss

$name1 stays late for a review and ends up bent over her boss’s desk with his cock opening her virgin arse.

The office was empty except for the hum of the servers and the soft glow of Mr Hale’s desk lamp.

$name1 stood in front of his desk in her blouse and skirt, performance review folder clutched to her chest like armour. He had asked her to stay behind. He always asked her to stay behind. Tonight his eyes had a different hunger in them.

“Shut the door, $name1,” he said. “And lock it.”

She locked it. Her cunt fluttered. She hated that it fluttered.

Hale leaned back in his chair, tie loosened, watching her. “You’ve been distracting every man on this floor for months. Crossing your legs in meetings. Bending over the printer. I’ve jerked off thinking about that arse more times than I’ll admit.”

Heat flooded her face. “Sir—”

“Tonight you’re going to put that arse on my desk. I’m going to eat it. Then I’m going to fuck it. Have you ever taken a cock there?”

$name1’s mouth went dry. “No. Never.”

“Good.” He stood, walked around the desk, and turned her to face it. “First time belongs to me. Bend over.”

She bent. Cheek to cool wood. He shoved her skirt up, dragged her knickers down to her knees, and spread her cheeks with both thumbs. For a long moment he just looked. Then his tongue dragged over her arsehole, hot and filthy, and $name1 whimpered like she’d been shocked.

“Oh my god—”

“Quiet,” Hale muttered against her. “Or the cleaners will hear what a slut my assistant is.”

He licked her open with patient, filthy focus — circling, pressing, fucking the tip of his tongue into the tight ring while his fingers rubbed her dripping cunt. $name1 gripped the far edge of the desk, hips pushing back despite herself. No one had ever touched her there. The shame and the pleasure braided together until she was moaning into the wood.

He stood. She heard the belt. The zipper. The wet sound of him stroking himself with her juices.

“Spit,” he ordered, holding his cock near her face.

She spat on the thick head. He rubbed it against her virgin arsehole, pressing, not entering yet.

“Ask for it, $name1. Ask your boss to fuck your arse.”

Her voice shook. “Please, sir. Please fuck my arse. Stretch me. I want your cock in my virgin hole. Ruin me on your desk.”

He pushed.

The burn was sharp and overwhelming. $name1 cried out, then bit her lip as the head popped inside. Hale held still, breathing hard, one hand stroking her back.

“Good girl. Breathe. You’re taking your boss’s cock in your arse like you were made for it.”

He fed her another inch. Then another. She felt split open, impossibly full, every nerve screaming. When his hips finally met her cheeks she sobbed with relief and need tangled together.

“Fuck — you’re so tight,” Hale groaned. “This arse is mine now. Say it.”

“My arse is yours,” $name1 gasped. “Fuck it. Please fuck it.”

He started to move — slow at first, then deeper, then harder as her body loosened and the burn melted into a dark, filthy pleasure she’d never known. The desk creaked. Her tits scraped the wood through her open blouse. Every thrust punched a moan out of her.

Hale reached under and rubbed her clit while he fucked her arse. “$name1. Cum for me. Cum with my cock buried in your virgin hole.”

She came hard, screaming into her forearm, cunt clenching on emptiness while her arse fluttered around him. The orgasm ripped through her like lightning. Hale cursed, slammed deep, and flooded her arse with hot cum — pulse after pulse, claiming her from the inside.

He stayed buried for a long moment, then pulled out slowly. She felt empty and used and dripping. Cum leaked down her thighs onto the office carpet in a sticky trail she could feel with every breath.

Hale crouched behind her and spread her cheeks again, watching his cum drip from her stretched arsehole. He pushed two fingers back into her, scooping, then stood and held them to her lips.

“Clean them. Taste what I put in you.”

$name1 sucked his fingers clean without hesitation, tasting salt and herself and the shame that made her cunt throb all over again. He kissed her forehead almost gently — a terrible contrast to what he’d just done to her.

He wiped his cock on her knickers, then tucked them into his pocket like a trophy. “You’ll go home without these. Tomorrow you’ll wear a plug to our ten o’clock — I’ll leave one in your top drawer. And $name1?”

She straightened on shaky legs, skirt smoothed down over her bare, aching arse. “Yes, sir?”

“This stays between us. But it isn’t a one-time thing. Next late night, I fuck your throat first until you cry. Then I take this arse again. Clear?”

“$name1 understands,” she said, and the smile she gave him was filthy and grateful and already hungry for more. “Should I thank you for my first time, sir?”

“You already did. With that scream.”

She walked to the lift with cum in her arse and her boss’s want still ringing in her ears. In the mirrored walls she looked thoroughly debauched — lipstick smeared, blouse wrinkled, eyes bright. She pressed the ground-floor button and clenched around the ache he’d left, already wondering how thick the plug in her drawer would be, and how loud she’d have to be quiet when he bent her over that desk again.

Author: Alice

Alice is one of the founding authors of NaughtyFable.com, and enjoys a variety of erotic kinks from cuckolding and voyeurism, to oral fixations and fantasy genres.