Sissy's New Boss Craves Her Silky Stocking Cock

Sissy clicked across the marble floor of the executive suite in her four-inch patent heels, the whisper of her sheer black stockings rubbing together with every step. At twenty-two, she knew exactly how her body looked in the tight charcoal pencil skirt that hugged her round ass and slim hips. The silk blouse clung to her perky tits, but it was the unmistakable bulge already straining against the front of her skirt that made her pulse race. She had been warned that Marcus Kane, the openly perverted CEO of Kane Enterprises, had very particular tastes. She just hadn’t expected him to be so brazen about it on her first day.

Marcus sat behind a massive oak desk, suit jacket already discarded, white shirt unbuttoned at the throat. He was in his mid-forties, broad-shouldered, with a trimmed salt-and-pepper beard and dark eyes that locked onto her the second she stepped through the door. His gaze dropped immediately to the thick, obscene outline of her cock where it pressed against the silky nylon, trapped sideways along her thigh.

“Close the door, Sissy.”

She did. The soft click of the lock he hit on his desk remote made her cock twitch visibly.

Marcus leaned back, palming the growing hardness in his own slacks. “Let’s not waste time on pleasantries. I hired you specifically because of that.” He pointed two fingers at the prominent bulge. “I have an insatiable craving for silky stocking cock, and yours looks fucking perfect. Thick, heavy, already leaking I bet. Show me.”

Sissy’s breath caught. Heat flooded her cheeks and her shaft at the same time. She stepped closer until she stood between his spread knees. With trembling fingers she gripped the hem of her tight pencil skirt and slowly dragged it upward. The silky material whispered over her thighs until the full length of her cock was revealed, wrapped tight in sheer black nylon, the wide cockhead clearly visible through the glossy fabric. A thick bead of precum had already soaked through, leaving a wet spot the size of a quarter right at the tip.

“Fuck,” Marcus groaned, eyes glazed with raw hunger. “Look at that pretty trans cock all gift-wrapped for me. So fucking smooth. So silky. I can see the vein pulsing under the nylon. You’re dripping, baby. That’s all for your new boss?”

“Yes, Sir,” she whispered, voice husky. Her cock gave another heavy throb, pushing harder against the delicate sheer weave. More precum oozed out, turning the black nylon even darker and shinier.

Marcus slid off his chair and dropped to his knees in front of her like a man starving. He pressed his face directly against the warm, silky bulge, inhaling deeply. The heat of his breath made her balls draw up tight inside their nylon prison.

“Goddamn, that scent. Stockings and leaking girl-cock. I’m going to ruin these pretty things.” He rubbed his cheek along the thick shaft, then opened his mouth and dragged his tongue up the entire length through the nylon. “Use my mouth, Sissy. Fuck my face through your stockings. I want to feel every inch sliding over my tongue while it’s still wrapped in silk.”

The filthy plea broke what little restraint she had left. Sissy grabbed the back of his head with both hands, hips rolling forward. She dragged the fat, stocking-covered head across his lips, then pushed. The sheer nylon stretched around her cockhead as it slid into the wet heat of his mouth. Marcus moaned like a whore, eyes rolling back as she began to thrust.

She face-fucked him with long, deliberate strokes, the silky material growing soaked with his spit and her endless precum. Obscene wet sounds filled the office—gluck, gluck, gluck—while strings of mixed fluids dripped from his chin onto his expensive shirt. Every time she pulled back, the nylon clung wetly to her veiny shaft, now completely transparent where it stretched over her cock.

“Enough teasing,” she growled, voice dropping into a filthy register she rarely used. She reached down, hooked two fingers into the crotch of her stockings, and ripped. The delicate nylon tore with a loud shrrrip, creating a perfect hole that let her bare cock spring free—thick, veined, glistening, and flushed dark pink. Her balls still swung heavy behind the torn silk.

Marcus was panting, lips shiny. “Please…”

Sissy grabbed him by the tie, spun him around, and bent the big CEO over his own desk. She kicked his feet apart, yanked his trousers and boxers down to his ankles, and pressed the slick, bare head of her cock against his tight hole.

“No condom,” she warned.

“Fuck no,” he answered, pushing back. “Breed me.”

She drove in with one rough thrust, burying half her cock in his ass on the first stroke. Marcus cried out, hands scrabbling across the polished wood. She gave him no time to adjust—just pulled back and slammed in again, deeper, until her smooth hips met his ass and her torn stockings rubbed against his skin. The contrast of her silky thighs against his balls as she started pounding him was obscene.

Sissy fucked him hard, deep, relentless strokes that made the heavy desk shift. Each thrust made her balls swing forward and slap against him, the torn nylon framing her shaft like a filthy picture frame. Marcus reached back between his own legs, wrapping his fist around the base of her cock every time she pulled out, stroking the slick length while her thighs glided against his knuckles in their silky embrace.

“Harder,” he begged. “Use me like the stocking-cock whore I am.”

She pulled out suddenly, cock glistening with his ass juices, and dropped into his chair. “On my lap. Reverse. I want you to feel every inch of these stockings rubbing your balls while I fill you.”

Marcus didn’t hesitate. He straddled her backward, reaching back to guide her cock back into his stretched hole. The moment he sank down, the torn edges of her stockings dragged along his heavy sack. Sissy moaned at the sight—her thick cock disappearing into his ass while her sheer black legs framed everything. She grabbed his hips and started bouncing him, using him like a fleshlight.

The wet slap of skin and the constant silky glide against his balls drove them both wild. Marcus stroked himself frantically, moaning like a slut while she railed him from below. Her cock throbbed violently inside him.

“I’m gonna cum,” she hissed, nails digging into his waist. “Right up your greedy CEO ass.”

“Do it. Fill me.”

Sissy slammed up one last time and exploded. Thick ropes of hot cum blasted deep inside him, pulse after pulse, until it was leaking out around her shaft and soaking the torn remains of her stockings. She kept grinding through it, milking every drop into his guts while he jerked himself to his own shattering orgasm, painting the front of his desk with long white streaks.

For a long moment the only sounds were their ragged breathing.

Sissy finally eased him off her spent cock. It slid out with a wet pop, already softening but still impressive, glistening with cum and ass juice. She stood, towering over him in her heels, and pointed at her messy, ruined stocking-covered crotch.

“Clean your new favorite toy, Mr. Kane.”

Still on his knees, Marcus leaned in obediently and began licking her cock and balls through the torn, cum-soaked nylon. He sucked every drop of their combined mess from the sheer fabric, humming with filthy satisfaction.

When he finally pulled back, lips swollen and shiny, he looked up at her with pure lust.

“Consider this your orientation complete. Tomorrow we’ll have your first official performance review. I expect that silky stocking cock down my throat before coffee, and buried in my ass before lunch. Wear something even filthier.”

Sissy smiled, slow and wicked. She smoothed her pencil skirt back down over her spent but still twitching cock, the huge wet spot at the front impossible to miss. Without another word she turned, walked to the door, unlocked it, and stepped out into the hallway—heels clicking, torn stockings whispering against her thighs, already planning the crotchless bodysuit and seamed stockings she would wear for him tomorrow.

The door shut softly behind her.