Sissy Story - The Corporate Takeover

I signed the last page with a hand that would not stop shaking.

Vera took the pen back. She did not thank me. She set the contract on the glass desk and tapped the clause I had already read three times, the one that put my company under her control and put me under something worse.

“You still own the apartment,” she said. “For now. Everything else is mine. Including you.”

My cock twitched in my suit trousers before my mind could catch up. Heat crawled up my throat. Thirty-four years of boardrooms and clean exits, and my body answered her like a dog hearing keys.

I tried to hold her stare. She wore black silk and a blazer cut sharp enough to cut. Her nails were red. Her mouth was calm.

“I can still walk,” I said. My voice came out thin.

“You can. The door is unlocked. Walk out and I call the creditors tonight. Your name hits every trade paper by morning.” She tipped her head. “Or you stay. You kneel. You learn what you signed for.”

My knees knew the answer first. I hated that. I locked them hard and stayed on my feet, breath snagging, while my cock thickened against the zipper like it had already chosen her.

She opened a drawer. Black lace spilled over her palm. A pair of panties. Sheer stockings. A pink silicone plug with a flared base. A small silver key on a thin chain.

My stomach dropped. My cock jumped again, harder, traitor-fast, and the shame of it made my face burn.

“Take off the suit,” Vera said. “Fold it. Put it on the chair. You do not wear men’s clothes in my office after eight.”

I stood there one second too long. She waited. No raised voice. No threat beyond what she already owned.

I stripped.

Jacket. Shirt. The belt I had worn to close deals. My hands fumbled the zipper. My cock sprang free, half hard already, flushed and wet at the tip. I almost covered it. Her eyes stopped me.

“Look at that,” she said. “You lose your company and you still get hard for the woman who took it. Put the lace on.”

The panties were soft. Real silk, not cheap costume fabric. They slid up my thighs and cupped my cock in a tight pink pouch that left nothing to the imagination. The front tented. A dark spot spread where precome soaked through.

I almost laughed. It came out broken.

Vera stepped in. She took my chin. “Stockings next. Sit on the desk. Face me.”

The glass was cold under my bare ass. I rolled the sheer black stockings up one leg, then the other, careful with the seams the way she watched me be careful. The lace tops dug into my thighs. My cock strained the panties harder, trapped and leaking.

Some clean version of me, the one who still sat at the head of a table, screamed that this was a joke I could still end. That man felt far away. The man on the desk kept dressing.

“Stand. Turn. Hands on the glass. Ass out.”

I obeyed. The position shoved my hips back. Air touched the cleft of my ass through the thin silk. My ears rang.

Vera’s palm settled on my lower back. Firm. Claiming. “You signed for chastity. You signed for training. You signed for whatever I put on you, in you, and around your cock until I decide you have earned the right to come. Say yes, Mistress.”

My mouth was dry. “Yes, Mistress.”

“Good sissy.”

The word landed low in my gut. My cock kicked in the lace. I bit my lip so I would not make a sound.

She peeled the panties down just enough. Cool gel on her fingers. Then pressure at my asshole, patient and certain. The tip of the plug kissed me. I clenched on instinct.

“Breathe out,” she said. “Push back onto it. You do not get to keep this hole closed anymore.”

I pushed. The plug opened me, thick enough to burn, slick enough to slide. My rim stretched around the widest part and then closed on the neck. The base sat snug between my cheeks. Full. Wrong. So full I had to lock my knees to stay up.

My cock dripped a string onto the desk.

Vera pulled the panties back into place over the plug. The lace pressed the base deeper when I shifted. Every small move made my cock jump and my face heat.

“Pretty,” she said. “Now the cage.”

She held up a clear plastic chastity cage, curved, with a lock at the base. Small. Mean. Built for a cock that was already too hard to fit clean.

“Please,” I said, and I did not know if I meant stop or hurry.

“Quiet. Soft for me. Or I ice you and put it on cold.”

I stared at the far wall and tried to think of anything that was not her hands, her voice, the plug in my ass. My cock stayed stubborn. She wrapped cool fingers around the shaft and squeezed once, hard enough to steal the edge. Then she fed me into the cage piece by piece, forcing the head into the tube while I hissed through my teeth.

The ring locked behind my balls. The cage closed. The click of the lock was small and final.

My cock tried to swell and hit plastic. Pressure. Nowhere to go. The ache hit fast. Precome beaded at the tip of the cage and dropped onto the glass.

Vera hung the key around her own neck. It rested against her collarbone like jewelry.

“You stay locked until I open you. Weeks. Months. However long it takes to break the man who thought he ran this firm.” She tapped the cage. “This is mine. Your ass is mine. Your mouth will be mine. Say it.”

“My cock is yours. My ass is yours. My mouth is yours.” The words came out rough. Saying them made my trapped cock pulse against the plastic until my eyes watered.

She smiled with half her mouth. “On your knees. Crawl to the couch.”

The carpet burned my knees. The plug shifted with every inch. My caged cock bounced useless and heavy between my legs, the pink lace stretched tight around the plastic. I crawled past the windows that looked over the city I used to own, and I kept my eyes on the floor because if I saw my reflection I might shatter.

Vera sat on the black leather couch and crossed her legs. She pointed between her feet.

“Closer. Face in. Breathe me.”

I pressed my face to the inside of her thigh. Silk stocking. Warm skin. The scent of her cunt under the skirt. My mouth watered. My caged cock throbbed in a useless, furious rhythm.

She uncrossed her legs and hiked the skirt. No panties. Bare pussy, shaved smooth, already glossy at the slit. She opened herself with two fingers and held my head by the hair.

“Worship. Slow. You do not get to rush. You do not get to come. You get to make me wet while that little thing stays locked and crying.”

I licked. Long strokes up her folds. The taste hit me and my hips jerked, grinding the cage against nothing. The plug rolled inside me. A broken sound left my throat and went straight into her cunt.

“That’s it. Tongue on my clit. Circles. Good boy. Good girl. Both. Whatever you are now.”

I worked her clit the way she ordered, careful, then firmer when her grip tightened. Her hips rolled against my mouth. Wet sounds filled the office. My jaw ached. My cock ached worse, swollen tight against the cage, balls drawn up and denied.

She pushed two fingers into her pussy beside my tongue, fucked herself once, then pulled those wet fingers free and shoved them into my mouth.

“Clean. Taste what you do to me when you crawl.”

I sucked. Salt and heat. My tongue worked between her knuckles like I had been waiting my whole life for this exact filth. The thought that I used to fire men for less than this made my stomach turn and my cock leak into the cage at the same time.

Vera pulled her fingers free. She reached down and pinched one of my nipples through nothing but air and shame, hard enough that I gasped.

“Stand. Hands behind your head. Present.”

I stood. Legs apart. Chest out. Pink lace. Black stockings. Clear cage shiny with precome. Plug base visible under the thin fabric when she turned me.

She walked a slow circle. Inspection. Her heel clicked once on the floor and the sound went up my spine.

“You look expensive,” she said. “Like a secret I bought with your own money. Turn your head. Look at yourself in the window.”

The glass threw my reflection back. A grown man in lingerie with a locked cock and a plug in his ass, mouth shiny from her cunt. The man who closed the East Harbor deal. The man who never knelt.

I almost looked away. She caught my jaw and held me there.

“Stay. See what I made.”

My reflection stayed. My cock strained the cage until the plastic bit. A thin line of precome ran down the tube and onto the lace.

Vera opened another drawer. She brought out a remote and a small egg vibrator, pink to match the panties. She slipped the egg into the front of the lace, nestled against the underside of the cage where the plastic left a gap of skin. One click. Low buzz.

My knees buckled. The vibration hit the trapped cock and the plug at once through bone and tension. I grabbed for the desk and missed. She caught my arm and held me up like I weighed nothing.

“Stay standing. Hands behind your head. You do not touch. You do not hump the air. You take it.”

The buzz climbed. My hips jerked against orders. The plug rocked deep. My cock tried to get hard in a space that would not allow it, and the denial turned the pleasure sharp, mean, endless. Sweat ran down my spine into the lace waistband.

“Please,” I said again. “Mistress. Please.”

“Please what.”

“Please let me come. Or stop. Or, fuck, I don’t, I can’t,”

“You can. You will. You are going to stand here and leak for me until your legs shake. Then you are going to thank me for the cage.”

The remote clicked higher. My vision narrowed. A wet spot spread across the front of the panties until the lace clung translucent to the plastic. My balls pulled tight. Orgasm hovered right there, thick and close, and the cage refused it. The edge went on and on until my thighs trembled and a broken noise tore out of me.

Vera shut the vibe off.

The silence hit like a slap. My cock throbbed in furious little jumps. Nothing. No release. Only the ache and the plug and her calm breathing.

“Thank me.”

“Thank you for the cage, Mistress.” My voice cracked on the last word.

“Thank me for the plug.”

“Thank you for the plug, Mistress.”

“Thank me for making you pretty.”

Heat flooded my face. “Thank you for making me pretty, Mistress.”

She kissed the corner of my mouth. Soft. Controlled. Then she bit my lower lip hard enough to sting.

“Tonight was orientation,” she said against my mouth. “Tomorrow you report at seven in the clothes I leave on your bed. You will wear the cage under your skirt. You will sit through the board call with a plug in your ass and a remote in my pocket. If you come without permission, I sell the apartment and put you in the guest suite with a collar and a schedule.”

My pulse hammered in the cage. “Yes, Mistress.”

She stepped back. Looked me over one more time. Then she unhooked the front of her blazer, let it fall, and the black silk blouse underneath opened on a line of skin I wanted to put my mouth on until I forgot my own name.

“On the couch. On your back. Legs open. Hold your knees.”

I lay down. The leather stuck to my bare shoulders. I pulled my knees up and apart, stockings stretched, lace crotch on full display, cage pointing useless at the ceiling. The position opened my ass around the plug base. Exposed. Owned. Harder than I had ever been in my life and locked out of every relief.

Vera stood between my spread thighs and stripped the rest of the way down. Full breasts. Hard nipples. That wet cunt I had just worshipped. She took a thick black strap-on harness from the side table, stepped into it, and buckled the straps tight around her hips. The dildo jutted out heavy and long, glossy, ridged near the base.

My hole clenched on the plug already inside me. My caged cock gave a helpless spurt of precome that rolled down onto my stomach.

She stroked the shaft once with a slick palm and smiled the way she had smiled when she took my company.

“First you lose the company,” Vera said. “Then you lose the right to come. Now you lose the last place you thought was still yours.”

She hooked two fingers under the base of the plug and began to pull.

My rim stretched. The burn bloomed. My locked cock jumped and strained and got nothing. I held my knees wider because she had told me to, and because some raw hungry part of me already needed what came next more than air.

The plug left me empty with a soft wet sound. Cool air hit my open asshole. Vera lined the thick head of the strap-on against me, pressed until the tip nestled just inside, and paused there with her hands locked on my thighs.

“Beg for it,” she said. “Use the word sissy. Mean it.”

My mouth opened. The city lights blurred beyond the glass. The key to my cock shone between her breasts. The head of her cock sat in my ass and waited, and every proud thing I had ever been sat right there on the edge of breaking.