Sissy Story - The Mistress's Interrogation Room

I signed the consent form with a hand that already trembled. The ink looked too black against the white paper, permanent in a way my resolve was not. Mistress Claire took the sheet, folded it once, and set it on the steel table like a finished meal.

The interrogation room smelled of polish and cold metal. A single lamp hung over a bolted chair with black straps hanging from the arms. Mirrors lined one wall, and I hated how clearly they threw my face back at me, jaw tight, eyes too bright.

She wore black trousers and a white blouse open at the throat. No costume. No performance. Just certainty. Her heels clicked once on the concrete, then stopped.

“Stand there. Hands at your sides. Eyes on me.”

I obeyed before my pride could invent a reason not to. My cock thickened in my jeans at the sound of her voice alone, and the heat of that betrayal crawled up my neck. Thirty-two years of running meetings, of being the man who decided things, and a single order had me half hard under denim.

She circled me. Fingers traced the back of my collar, then the belt loops at my hips. When she stopped in front of me again, her gaze dropped to the bulge and stayed there.

“Already. And we have not even begun.”

I opened my mouth to deny it. Nothing useful came out.

She unbuttoned my shirt with tidy, efficient motions, each button a small theft. The fabric left my shoulders, and the cool air found my skin. She folded the shirt and set it on the table. Next came my belt, drawn free with a soft hiss. My jeans and boxers followed until I stood bare under that lamp, cock rising against my will, flushed and obvious.

“Turn. Look at yourself.”

I faced the mirrors. A tall man with a hard jaw and a traitorous erection stared back. Behind him, Mistress Claire stood with her arms crossed, assessing me the way a tailor assesses cloth.

“Tonight you stop being that,” she said. “Tonight you become useful.”

She opened a black case on the table. Lace and silk waited in neat stacks, pale pink and cream, the kind of fabric that belonged on someone else. Beside them sat a steel chastity cage, a bottle of lube, a remote, and a thick pink strap-on harness with a curved dildo already locked into place. My mouth went dry.

If I walk out now, I still get to pretend I only came for the dare.

My feet stayed planted.

She held up a pair of pink lace panties. “Step in.”

I stepped. The lace dragged up my thighs and settled over my cock, thin and useless as a cover. The front pouch stretched obscenely. She smoothed the fabric with two fingers, then cupped me through the lace until I twitched into her palm.

“Pretty already,” she murmured. “We will make you prettier.”

A matching bralette came next, straps adjusted tight enough that the lace bit lightly into my chest. She clipped a thin silver chain between the cups and gave it a small tug. My nipples tightened. Shame flooded my gut in a hot, sick rush that only made my cock push harder against the lace.

She guided me to the chair. “Sit.”

The leather was cold under my bare ass. Straps closed around my wrists and ankles with soft clicks. I tested them once. No give. My pulse hammered in my throat.

Mistress Claire knelt between my spread knees and looked up at me with calm eyes. “This cock has made too many decisions for you. We fix that first.”

She peeled the lace aside. Her fingers were cool and sure as she rolled a thin silicone sleeve down my shaft, then fitted the steel cage over it. The ring locked behind my balls with a quiet snick that seemed louder than it should have. Instantly, the pressure changed. My cock tried to swell and met steel. A dull ache bloomed at the base.

I made a sound I did not choose.

“Good,” she said. “Feel that. That is ownership.”

She set the key on a chain around her own neck. The metal rested in the hollow of her throat like a private joke. Then she pulled the lace panties back over the cage so the steel shape showed through the pink. In the mirror, I looked ruined already. Feminized from the waist up in lace, locked and helpless below.

She stood and unfastened her trousers. The harness came next, black straps settling over her hips, the pink dildo jutting thick and shameless from her body. She stroked lube along the shaft with unhurried passes, the wet sound filling the quiet room. My empty hole clenched at the noise alone.

“You will answer every question,” she said. “You will use full sentences. You will call me Mistress. If you lie, or hedge, or try to sound like a man who still has options, I stop being patient.”

She rolled a stool between my knees and sat. One gloved finger, slick with lube, pressed against my asshole. I flinched. She waited until I settled, then pushed inside to the first knuckle.

The stretch burned sweet and low. My caged cock jerked uselessly against steel. Sweat pricked along my hairline.

“Question one. Why did you come here tonight?”

I swallowed. “I wanted… I wanted to try submission.”

Her finger curled. Found a spot that made my thighs jump. “Try is a tourist word. Try again.”

The second finger joined the first. Fuller. Meaner. She scissored once, and my breath broke apart.

“I came because I cannot stop thinking about being forced into this. About being dressed and locked and used.”

“Better.” A third finger stretched me open until my hole fluttered around the intrusion. “And what do you want to be called when I am finished with you?”

My brain reached for a name that still belonged to boardrooms and bar tabs. What left my mouth was thinner.

“Sissy. I want to be called your sissy.”

Her smile was small and pleased. “There he is. Or rather, there she is.”

She withdrew her fingers. The emptiness hit harder than the stretch. Before I could brace, the blunt head of the strap-on pressed to my slicked hole. She held still, letting me feel the size of it, the promise of how deep it would go.

“Last chance to use a safe word,” she said. “After this, you earn every inch by answering. Clear?”

“Yes, Mistress.”

She pushed.

The head breached me in one thick slide, and a raw sound tore out of my chest. My wrists yanked against the straps. The cage clamped down on my desperate cock until the ache turned sharp. She fed me more, slow and relentless, until the harness kissed my ass and the dildo sat heavy inside me, rearranging everything I thought I still controlled.

“Breathe,” she ordered.

I breathed. Barely.

She began to fuck me in short, measured thrusts. Each one drove the toy across that swollen place inside me until sparks of pressure built behind the cage. My lace-covered chest rose and fell too fast. Pink fabric stuck to my damp skin. In the mirror, a strapped man in lingerie took a pink cock like he had been waiting his whole life for it, and the worst part was how true that looked.

“Question two,” she said, hips rolling. “Tell me what you are, out loud, while I use this hole.”

“I am… ah… I am your sissy. I am locked. I am…” My voice cracked as she drove deeper. “I am a pretty thing for your cock.”

“Again. Filthier.”

She snapped her hips. The dildo punched that spot hard enough that my vision thinned at the edges. Precome leaked inside the cage with nowhere to go. My balls drew up, denied and frantic.

“I am a lace-wearing, cock-locked little slut who gets wet when you humiliate him. Who wants to be trained. Who wants to be made pretty and kept.”

“Him,” she corrected, and twisted the strap-on on the next thrust so I felt every ridge. “Wrong pronoun. Fix it.”

Heat flooded my face. “Who wants to be made pretty and kept. Who wants you to turn her into something obedient.”

“Yes.”

She reached for the remote on the table and pressed a button. Somewhere under the lace, a tiny vibe I had not noticed kicked on against the base of the cage. The vibration shot through steel into my trapped cock, merciless and precise. My body arched as far as the straps allowed. A broken moan escaped me.

She pegged me harder now, rhythm building, the slap of harness against ass filling the room. My hole stretched around the thick pink shaft, greedy and sore. Every thrust shoved me toward an edge I could not cross while locked. The denial made the pleasure vicious.

“You will come only when I unlock you,” she said. “If you ever come. That depends on how well you train. On how pretty you look when you beg. On whether you still try to hide the man you used to be.”

I nodded too fast. Words failed. Spit wet my lower lip.

She leaned in until her mouth nearly touched mine, still fucking me deep, still working that vibe against the cage. Her free hand closed around the chain between my lace cups and pulled until my back left the chair.

“Question three,” she whispered against my mouth. “When I take this dildo out and put you on your knees in front of that mirror, what will you ask me for?”

My mind scrambled. Pride offered one answer. My dripping, locked, lace-wrapped body offered another.

“I will ask you to finish turning me,” I said, voice wrecked. “I will ask you to dress me properly. To keep the key. To fuck my ass until I thank you for every thrust. I will ask you to make me your sissy for real.”

Her eyes darkened with satisfaction. She kissed the corner of my mouth once, almost tender, then slammed the strap-on home to the hilt and held it there, grinding.

The vibe climbed a notch. My caged cock pulsed in useless spasms. My hole clenched around the thick toy as if it could keep her inside forever. Tears pricked at the corners of my eyes, born of pressure and need and the sick, sweet knowledge that I meant every word.

Mistress Claire reached for the key at her throat.

She did not unlock me.

Instead she lifted a second item from the case: a wider plug, glossy black, and a silk scarf the color of old roses. She set them on my bare thigh where I could see them, feel their weight, understand what came next.

“That was the interview,” she said, and pulled the dildo halfway out so my empty rim fluttered around the tip. “Now we begin the real interrogation. And this time, sissy, you do not get to answer with words alone.”

She drove back in hard enough to knock the breath from my lungs, thumb poised over the vibe remote, the key still warm against her skin, and the only thought left in my head was how badly I needed her to break whatever was left of me before the night was done.