Skip to content
20% OFF YOUR FIRST ORDER | use CODE: NEW20.Shop Now

Free Shipping on All Orders Over $59

Crossdressing Stories

Sissy Story: Midnight Business

by Casey Perkin 09 May 2025 0 comments

The bass thumped low in the private lounge, lights pulsing with heat and hunger. The club was filled with noise, laughter, and the metallic scent of champagne. I'd worked here for almost three years, long enough to know when someone wasn't here for just a show.
She was different.

Vivian Locke.

I didn't know her name yet, but I recognized her the moment she walked in—sleek blazer over a silk blouse, heels that looked lethal, a phone in one hand and a drink in the other. She wasn't clapping, or throwing bills, or giggling with the rest of the bachelorette crowd. She was watching. Still. Intense. Like she owned the room—and maybe she did.

When my routine started, I worked the floor like usual. Rolled my hips, peeled my shirt off slow, let the crowd scream. But I kept coming back to her with every movement, every glance. Her red lips didn't curve. Her eyes didn't flicker. But they never left my body.

When the set ended, I stepped off stage slick with sweat, adrenaline still riding me like a drug. I wiped my face and reached into my locker.

A card.

Suite 1803. Midnight.

Elegant handwriting.

I hesitated for all of five seconds. I wasn't supposed to take private after-hours requests unless they went through the club. But rules blurred when temptation looked like her.
The suite was exactly what I expected—sleek, cold, expensive. Floor-to-ceiling windows with the city sprawled beneath, lights blinking like stars. She stood near the minibar, drink in hand, expression unreadable.

"I didn't think you'd show," she said.

"You invited me."

"I like men who follow instructions."

I stepped closer, eyes on hers. "What exactly are the instructions?"

She didn't answer at first. Just set her glass down and walked past me, heels echoing on the floor. Her perfume hit me like heat—dark florals and something sharper underneath. Her fingers grazed my chest.

"Take off your shirt."

It wasn't a question.

I obeyed.

She circled me slowly. Like a lioness deciding where to sink her teeth. "You're prettier up close."

"I get that a lot."

She smirked. "I doubt anyone tells you what to do."

I let her push me onto the couch, straddling me with confidence I hadn't expected. She didn't fumble, didn't rush. Her hands mapped my skin like she owned it. When she kissed me, it wasn't gentle—it was a test. And I passed it by kissing her harder.

Clothes came off. Restraint unraveled. The sex was messy, intense, not just physical—it was something else. Something about the way she held control until she couldn't. The way her breath hitched when I whispered her name. The way she moaned when I told her she didn't need to pretend to be in charge here.

Afterward, she pulled her blouse back on and lit a cigarette by the window, barely glancing at me.

"This doesn't leave this room," she said, voice calm, detached.

"Didn't plan on posting it on Instagram."

She gave a breath of laughter but didn't smile. "You're not who I thought you were."

"Disappointed?"

"Worried," she said. "You could be a problem."

I didn't expect to see her again. But the next Thursday, she was back. Same club, same seat. She didn't ask. Just nodded. I followed.

Every Thursday, it was the same. A private room. A few words. A lot of heat.

But she started to slip.

One night, she stayed longer. Let me kiss her slower. Let her guard down just enough for me to feel the chill behind her confidence.

She told me her name. Vivian. Said she ran one of the largest tech firms in the valley. Said she had a fiancé once. "He liked power games. So do I. But I like being the one holding the leash."

"Maybe that's why you keep coming back," I murmured. "Because I don't need one."

Her eyes narrowed, then softened. She leaned in. "Don't flatter yourself."

But that night, she stayed until morning.

We ordered breakfast. I watched her slip one of my T-shirts on like it meant nothing. She caught me looking.

"Don't read into this."

"I won't," I lied.

The truth was, I was already too deep. She made me want more. Not just her body—her time. Her thoughts. Her secrets.

One afternoon, I saw her outside the club with a man—tall, polished, a corporate shark in a gray suit. Her COO, I guessed. Maybe more. She didn't see me.

The next night, she didn't show.

Or the one after.

I didn't hear from her for a week.

Then, a message.

"My place. Tonight. Wear nothing underneath."

I went.

Vivian was already halfway drunk, heels off, hair down. There was something unsteady about her that night. Her touches were rougher. Her mouth tasted bitter. Her words more desperate.

"You'll ruin me," she whispered as she undid my belt. "You already are."

I pinned her wrists over her head. "Then stop coming back."

She moaned instead of answering.

The sex was furious, like punishment. When we were both breathless and tangled, I finally asked, "Why me?"

She didn't move. Just stared at the ceiling.

"Because you see me," she said. "And I hate that."

For a long time, neither of us spoke.

Then she said, almost too quiet, "What would you do if I asked you to stop dancing?"

"Would you ask?"

She didn't answer.

But she didn't send me away, either.

The next morning, she wasn't in bed. Just a note.

"I fly to Tokyo tomorrow. Might be a while. Don't wait."

I stared at the words.

And waited anyway.

The next time I saw her, something had shifted.

Vivian didn't say a word when I walked into her penthouse. She didn't kiss me. She didn't touch me. She just looked me over, cool and measured, and tossed a small velvet box on the bed.

"Put it on," she said, crossing her legs slowly.

I opened it.

A lace-trimmed black satin thong.

I blinked. "You're serious?"

Her brow arched. "You follow instructions. That's why I keep you around."

A flush crept into my neck, unexpected and warm. I should've pushed back. Should've joked, or resisted. But instead, my fingers moved. I undressed, slowly, and slid the delicate fabric over my hips.

It was soft. Tight. Indecent.

Her eyes gleamed with satisfaction.

"Now kneel."

There was something terrifying about how easily I dropped to my knees. How natural it

felt to obey.

She stood and walked behind me, her heels clicking against the marble floor. Her fingers brushed down my back—soft, then sharp. Nails.

"You like this," she murmured near my ear. "Don't lie to yourself."

I swallowed hard.

"I…" My voice cracked. "I don't know what you're doing to me."

Vivian laughed softly. "You're a beautiful mess. And now you're mine."

That night, she didn't just take me. She trained me.

She whispered instructions in my ear—how to present, how to beg, how to touch her exactly the way she wanted. She made me speak with my hands behind my back. Made me repeat humiliating lines with her fingers wrapped around my jaw.

"You're not a man here," she said, straddling me with silk ropes in her hands. "You're a toy. My little sissy plaything. Say it."

I hesitated—barely.

Her slap wasn't hard. But it was sharp enough to make my stomach flip.

"Say it, baby."

"I'm your… sissy," I whispered, cheeks burning, cock aching in the lace.
"Good boy."

From then on, it wasn't just sex. It was control.

She had me wear panties under my jeans when we met in public. Whisper filthy things to me over dinner. Once, she made me kneel in the backseat of her limo, lipstick smudged on my lips, one of her bras beneath my shirt. Her manicured nails traced my throat while her voice oozed command.

"You're softer than you pretend to be," she told me. "I see through you. You ache to be owned."

And the worst part was—she wasn't wrong.

I stopped dancing two weeks later.

No explanation. No fanfare. I just walked out of the club one night and didn't come back.

Vivian didn't ask me to quit. She didn't have to. She already had all of me.

She kept me in her world like a secret.

In public, I wore tailored suits and stood behind her like a shadow. In private, I wore whatever she chose—usually nothing but lace and a collar. She made me write lines. Kneel. Whisper her name like prayer.

Some nights she was gentle—petting me like something precious. Other nights, she broke me open with her teeth.

The only thing that didn't change was how badly I needed her.

One night, after she used me so thoroughly I couldn't move, she curled beside me and finally asked, "What do you want from me?"

I hesitated.

Then, honest: "More."

Her red lips curved. "More pain?"

"More you."

She looked at me, then reached for the drawer beside the bed.

A lockable collar. Simple. Elegant. Satin-lined.

"You want to belong to me?"

My chest tightened. I nodded.

She fastened it around my throat, fingers slow, reverent.

"There," she whispered, kissing my temple. "My sissy little boy. My pet."

And just like that, I stopped being her Thursday-night distraction.

I became hers.

Entirely.

Prev post
Next post

Leave a comment

Please note, comments need to be approved before they are published.

Thanks for subscribing!

This email has been registered!

Shop the look

Choose options

Recently viewed

Edit option
Back In Stock Notification

Choose options

this is just a warning
Login
Shopping cart
0 items

Before you leave...

Take 20% off your first order

20% off

Enter the code below at checkout to get 20% off your first order

CODESALE20

Continue Shopping