Erotic Story - Her Pretty Sissy

The conference room door locked with a soft click that went straight to my cock.

Vera stood with her back to the glass, thirty-two floors of city light behind her, and looked at me the way she looked at quarterly reports. Cool. Certain. Already decided. Her black pencil skirt hugged her hips. The silk blouse was open one button lower than she wore it for clients. She had kicked her heels off under the table. Bare feet on the carpet. Red toenails. She held something in her hand I could not name yet.

“You stayed late, Marcus. Good.”

My name still fit in the room. For now. My pulse did not. Heat crawled up my throat and settled low, thick and stupid, while my brain scrambled for the professional exit I should have taken twenty minutes ago. I had told myself I was only clearing the Q3 deck. I had told myself the look she gave me at five o’clock meant nothing.

My cock disagreed. It pressed hard against the seam of my trousers, already leaking enough that the cotton stuck.

“I can finish from home,” I said. My voice came out thin.

“You will finish when I say.” She set the small black bag on the table and unzipped it without hurry. Lace spilled out. Pale pink. Sheer. A pair of stockings rolled into a silk knot. Something metal caught the light. “Drop the laptop. Hands on the table. Palms flat.”

I did it. The polished wood was cold under my fingers. My reflection swam in the dark glass behind her, a man in a good shirt with his cock already shaming him through the wool. Thirty-one years old. Senior analyst. The one who closed the Langford account. And I was hard because my boss had brought panties into the conference room.

You can still walk out. Call it a misunderstanding. Keep your job and your spine.

I stayed.

Vera stepped close enough that her perfume hit me, something expensive and sharp. She reached for my belt. The buckle clicked. Zipper down. Cool air on my thighs. She peeled my trousers and briefs to my knees in one smooth pull and left them there, trapping me. My cock sprang free, flushed dark, the tip already wet. She looked at it the way she looked at a bad forecast.

“Small,” she said. Flat. Accurate. “Look at that. All that arrogance in meetings, and this is what you bring me.”

The word landed in my gut and twisted into heat. My cock twitched. A bead of precum slid down the shaft. She saw it. Of course she did.

“Oh.” A small smile. “You like that. Good. Honesty is the first lesson.”

Her fingers closed around me. Loose. Barely a grip. She stroked once, slow, and my hips jerked forward into nothing. She let go. I made a sound I did not recognize.

“Still,” she said.

I locked my knees. My balls ached. The shame of standing there with my pants around my ankles in the glass tower where I had presented to investors last week sat on my tongue like copper. She lifted the pink lace from the bag and held it up between two fingers. The crotch was tiny. Decorative. Meant for someone who did not have a cock.

“Step out of those. Fully. Then put these on.”

I stepped free of the trousers and briefs. Bare feet on corporate carpet. My shirt hung open over my chest because she had unbuttoned it while I was still processing the first order. She waited. I took the panties. The lace was soft. Expensive. The elastic stretched as I pulled them up my thighs. My cock tented the front immediately, the head peeking past the lace edge, wet and ugly against the pretty fabric.

Vera hummed. Approval. Or appraisal. “Turn. Hands on the glass.”

I turned. The city blurred thirty-two floors down. My breath fogged a small circle. Behind me, silk unrolled. She knelt. Her hands guided my foot into a stocking, then the other, the nylon whispering up my calves, over my knees, up my thighs. She clipped them to a garter belt I had not seen her put on me. The straps pulled. The stockings sat smooth and tight. When she stood and turned me back around, the reflection in the glass was worse than imagination. Shirt open. Pink lace. Stockings. A hard little cock straining the front of women’s panties like a joke that had become real.

“Pretty,” she said. “Almost. We fix the rest.”

She took the metal from the bag. A chastity cage. Clear polycarbonate. A small padlock. A ring. I had seen pictures once, late, alone, and closed the tab like it burned. She held it up so I had to look.

“This stays on until I decide otherwise. You will not touch yourself. You will not come. You will thank me when I let you leak.” Her eyes lifted to mine. “Kneel.”

My knees hit the carpet. The lace dug into my hipbones. My cock throbbed inside the pink, trapped and ridiculous. She stepped out of her own panties under the skirt, stepped forward, and the scent of her cunt hit me before the taste did. She fisted my hair and pulled my face between her thighs.

“Worship. Tongue flat. Do not get greedy.”

I licked. Her folds were slick already, salt and heat, her clit swollen under my tongue when I found it. She used my mouth like a tool. Adjusted my angle with her grip. When I tried to push deeper she pulled me back by the hair until my scalp sang.

“I said flat. You are not fucking me with your tongue. You are cleaning your superior.”

I flattened my tongue and worked her in long strokes. My cock jerked in the lace with every wet sound. Precum had soaked a dark patch through the pink. The cage waited on the table beside my abandoned laptop. The thought of that ring locking around my balls while I still tasted her made my stomach drop and my cock pulse harder.

She came on my face with a short, sharp breath and a grip that nearly pulled hair free. Her thighs shook against my cheeks. Cum and slick smeared my mouth and chin. She held me there through it, then pushed me back onto my heels.

“Look at you.” She dragged a thumb across my lower lip and forced it into my mouth. I sucked. “Messy little sissy. Say it.”

I swallowed. “Messy little sissy.”

“Louder. And add whose.”

“Your messy little sissy.” The words scraped out raw. My cock jumped so hard the lace shifted.

Vera smiled with her eyes only. She picked up the cage and the ring. “Stand. Hands behind your back.”

I stood. Stockings whispered when my thighs brushed. She worked the ring behind my balls first, cool plastic against hot skin, then guided my cock down into the tube. It was snug. Too snug for how hard I still was. She squeezed the base of my shaft with two fingers until the blood eased enough to seat me fully, and the pressure made my vision spark at the edges. The tube locked into the ring. The padlock clicked.

Gone. My cock was a locked shape under pink lace, visible, useless, owned.

“Breathe,” she said.

I breathed. My balls hung full and tight below the ring. Every heartbeat thudded in the cage. She adjusted the panties over the plastic so the lace framed it, pretty and exposed.

“Walk to the end of the table and back.”

I walked. The stockings made my gait wrong. Soft. The cage shifted with each step, a constant reminder that I could not get hard the way I used to, that hard now meant trapped and aching. When I turned, she was seated in the chair at the head of the table, legs crossed, one stockinged foot swinging.

“Again. Slower. I want to watch my pretty thing move.”

I walked again. Heat flooded my face. My cock tried to swell inside the cage and hit plastic. A thin sound left me. Vera uncrossed her legs and crooked a finger.

“Back on your knees. Between mine. Cheek on my thigh.”

I knelt. Rested my cheek on the smooth nylon of her stocking. Her hand stroked my hair like I was a pet she had trained. With the other she reached into the bag and produced a small remote and a bullet vibe, pink to match the panties. She slipped the vibe into the front of the lace, nestled against the cage and the skin of my locked cock, and switched it on low.

The buzz hit me like a slap. My hips stuttered. My mouth opened against her thigh.

“Still,” she said. “This is not for your pleasure. This is to remind you what you are while I decide how far we go tonight.”

The vibe hummed. My locked cock strained. Precum leaked through the vents of the cage and wet the lace and the vibe both. She increased the speed one notch. My thighs shook. The resistance thought came sharp and useless: This is your career, your name, your body, and you are letting her lock it in pink under the building cameras.

I stayed on my knees with my cheek on her stocking and my locked cock buzzing in lace.

Vera uncrossed something else from the bag. A slim plug, black silicone, flared base. Lube. She set them on the table where I could see them without lifting my head.

“You will take this next. Then you will thank me. Then we go to my office, and you will learn what your mouth is for when I am finished with your ass.” Her fingers tightened in my hair. “Ask for the plug, Marcus. Use the right name for yourself when you do.”

My mouth was dry. The vibe buzzed. The cage held me. The stockings hugged my legs. Her cunt was still glossy an inch from my face, and the plug gleamed under the overhead lights like a verdict.

I licked my lips. Tasted her. Tasted my own shame.

“Please put the plug in your sissy,” I said. The words came out cracked and hungry. “Please train me.”

Vera’s smile finally reached her mouth. She clicked the vibe one speed higher until my whole lower body jerked, and the plug and lube sat waiting on the polished wood while the city burned cold and distant behind the glass.

“Good boy,” she said. “Now bend over the table. Ass up. Lace pulled to the side. And do not you dare come.”