Sissy's Janitor Begs for Her Sheer Stocking Cock

The soft hum of the fluorescent lights was the only sound left on the twenty-third floor after eight o’clock. Sissy sat at the wide mahogany desk in the corner office, legs crossed, the tight charcoal pencil skirt hugging her hips and thighs like a second skin. Her sheer black stockings shimmered under the lamplight with every subtle shift, the delicate nylon catching faint reflections that made her long legs look almost liquid. Glossy patent six-inch heels dangled from her toes as she typed the final quarterly report, red nails clicking across the keyboard.

The door clicked open.

Marcus stepped in pushing his cleaning cart, mop handle rattling softly. The twenty-two-year-old janitor froze the moment he saw her. His gaze dropped immediately to those sheer stockings, tracing the delicate seam that ran up the back of her calf and disappeared beneath the hem of her skirt. He had been watching her for months—stealing glances in the elevator, lingering outside conference rooms, jerking off in the supply closet to the memory of her legs. Tonight his control finally snapped.

Sissy felt his stare like a physical touch. She slowly uncrossed her legs, then crossed them again the other way. The sheer nylon whispered, a soft, silky shhhick that cut through the quiet like a moan.

Marcus’s breath hitched audibly. The mop slipped from his fingers and clattered to the floor. Without thinking, he sank to his knees right there in the doorway, eyes wide and desperate.

“Please…” His voice cracked. “Miss Sissy… I can’t… I can’t take it anymore. I’ve been dying for months. Just… let me worship you. Let me worship your legs… your cock… please.”

Sissy leaned back in the leather chair, one perfectly arched brow lifting. A slow, wicked smile curved her crimson lips. She didn’t speak at first. Instead she recrossed her legs again, deliberately dragging one stocking-clad calf over the other so the nylon hissed louder this time. Marcus whimpered.

“Confess,” she said, voice low and velvet-smooth. “Tell me every filthy little fantasy you’ve had about me, janitor boy. Be specific. If you want my sheer stocking cock, you’re going to beg properly.”

Marcus’s hands trembled as they rested on his thighs. His cock strained painfully against his work pants.

“I… I jerk off every night thinking about your legs in these stockings. I imagine you sitting on my face, smothering me with your thighs while your cock stretches the nylon against my tongue. I dream about licking every inch of that sheer fabric until it’s soaked with my spit. I want to feel it get hard under my mouth, feel you throb through the silk while I suck you like a desperate whore. Please, Miss Sissy… I’ll do anything. I’ll clean this whole building with my tongue if you just let me taste you.”

Sissy’s smile deepened. She uncrossed her legs once more, spreading them just enough to let the tight skirt ride higher. The delicate bulge at the apex of her thighs was already visible—her cock half-hard and pressing against the sheer black gusset of her stockings and the tiny lace thong beneath.

“Keep going,” she purred, slowly sliding one glossy heel up and down her opposite calf, the nylon singing. “Tell me how you want to be used.”

Marcus crawled forward on his knees until he was between her spread legs, staring up at her with naked hunger.

“I want you to fuck my throat until I cry. I want you to rip those stockings open and bury every inch inside my ass while I’m bent over that desk. I want to feel your nylon thighs slapping against me. I want you to make me cum just from getting fucked by your stocking cock. Please… I’m begging you. I’m your filthy little janitor slut. Use me.”

Sissy’s cock surged fully hard at his desperate words, the thick shaft now clearly outlined beneath the delicate sheer nylon, veins and ridges visible through the glossy fabric. A small wet spot of precum had already bloomed near the tip.

She reached down, delicate fingers tracing the massive bulge.

“You’ve been such a patient, obsessed little boy,” she murmured. “Look at you on your knees, shaking. Fine. Prove it.”

With a graceful motion she hiked her pencil skirt all the way to her waist, fully revealing the obscene sight: her long, elegant cock encased in the sheerest black stockings, the material so fine it looked painted on. The head glistened with precum, stretching the nylon into a lewd, shiny dome.

Marcus moaned like he’d been struck. He lunged forward without waiting for further permission, pressing his open mouth against the silky shaft. His tongue dragged up the entire length, tasting the smooth, slightly textured nylon and the salty tang of her precum seeping through. He sucked greedily at the head, lips sealed around the sheer-covered glans, cheeks hollowing as he nursed on her through the delicate fabric.

Sissy sighed in pleasure, one hand sliding into his messy hair. “That’s it… worship it. Show me how long you’ve needed this.”

Marcus licked and sucked with frantic devotion, lapping at every inch of her silk-clad cock. The sheer nylon grew wet and translucent under his tongue, clinging obscenely to her throbbing flesh. He moaned around her, the vibrations traveling straight to her balls.

Finally Sissy gripped his hair tighter and pulled him back. With a sharp rrriiiip, she tore a neat hole right at the crotch of her stockings. Her cock sprang free—thick, veined, and glistening—still framed by the torn edges of black nylon like a lewd gift.

“Open your throat,” she commanded.

Marcus obeyed instantly. Sissy stood, towering over him in her glossy heels, and fed her bare cock between his lips. She didn’t go slow. She pushed deep, sliding over his tongue until she felt his throat open and accept her. Holding his head steady, she began to fuck his face with long, smooth strokes, the torn stockings brushing against his nose and chin with every thrust.

Saliva dripped from his stretched lips. His eyes watered but never left hers.

After several minutes of thorough throat-fucking, Sissy pulled out with a wet pop. She spun him around and bent him over the wide executive desk, yanking his pants and boxers down in one rough motion. His ass was smooth and pale, clenching in anticipation.

She spat on her cock, lined up, and drove in.

Marcus cried out in pure bliss as she buried all eight inches inside him. The torn nylon around the base of her cock rubbed against his stretched rim with every thrust. Sissy fucked him hard, hips snapping, the sound of skin meeting skin echoing through the empty office. One hand reached around to stroke his leaking cock through the front of his bunched-up pants, squeezing and teasing.

“You feel that, janitor boy? That’s my sheer-stocking cock owning your ass.”

She pounded him relentlessly in standing doggy, then suddenly pulled out, sat in the big leather office chair, and dragged him on top. Turning him to face away from her, she pulled him down into reverse cowgirl. Marcus sank onto her cock with a broken moan, impaling himself completely. Sissy’s hands gripped his hips as she thrust upward, the torn stockings sliding against his balls and inner thighs with every bounce.

He rode her desperately, rolling his hips, feeling every veined inch stretch him open while her nylon-clad thighs pressed hot and smooth against his skin. Sissy reached around again, jerking him fast and tight.

“Cum for me,” she growled against his ear. “Cum while I fill you.”

Marcus shattered first. Thick ropes of cum splattered across the torn black nylon of her stockings and down her glossy heels as he convulsed on her cock. The sight and sensation pushed Sissy over the edge. With a low, throaty cry she buried herself to the hilt and unloaded, pumping jet after jet of hot cum deep into his clenching ass until it overflowed and dripped down her balls.

They stayed locked together for a long moment, breathing hard.

Finally Sissy eased him off. Her spent cock glistened with cum and lube. She guided his head back down.

“Clean me.”

Marcus obeyed without hesitation, licking her softening cock through the torn, cum-soaked stockings. He sucked every drop of their combined mess from the delicate nylon, moaning softly at the taste.

When she was satisfied, Sissy stood. She let him jerk his spent cock one last time, aiming it at her beautiful legs. Marcus painted her sheer black stockings with the last weak spurts of his orgasm, thick white streaks contrasting obscenely against the glossy black nylon.

Sissy smiled down at him, calm and regal once more. She smoothed her pencil skirt back into place, hiding the torn crotch and glistening cock. Her heels clicked as she stepped around the desk, leaving him on his knees, trembling and covered in their combined fluids.

“Clean every trace of this, janitor,” she said coolly, voice once again that of the composed executive. “I expect this office to be spotless.”

She turned and strode toward the door, hips swaying, the faint shhhick of her cum-streaked stockings still audible with every step. Just as her hand touched the door handle, the sharp electronic beep of the security system echoed down the hallway outside—followed by the unmistakable sound of heavy boots and two male voices talking quietly.

The night security team was doing their ten o’clock rounds.

Sissy paused, lips curving into a dangerous little smile as she glanced back at Marcus’s wide, cum-drunk eyes.

“Better hurry,” she whispered.

Then she slipped out, leaving the trembling janitor on his knees with a belly full of her cum, stockings ruined, and the sound of approaching footsteps growing louder down the corridor.