The First Time I Paid Her to Break Me

I never told anyone about the first time I paid for it.

Not my friends, not the therapist I lied to for three years, not even the girl I was dating who thought my “kink” was just liking it from behind. Paying a woman to beat my ass raw felt like the ultimate proof I was fucked up. Her name was Mistress Cassandra, and I found her on a site that’s been dead for years. One page. Rules. Limits. A tribute that made my stomach flip. I sent the money at 2 a.m. with shaking hands, praying she’d disappear so I could pretend I never tried.

She didn’t disappear.

Friday night, room 1218. I stood outside the door sweating bullets in December. The door cracked open, a manicured hand snatched my tie, and I was inside before I could breathe.

She was tiny—five-four without the boots—but the second our eyes met I dropped to my knees like gravity had doubled. Black leather corset crushing her waist, tits pushed up like weapons, thigh-high boots that turned her legs into forever. Hair like ink to her ass. Eyes that looked bored with my entire existence.

“You’re late.” Flat. Cold. No smile.

“I’m sorry, Mistress.”

“Strip. Fold everything. Corner. Nose to the wall, hands behind your head.”

I obeyed so fast I tripped. Naked, freezing, cock already betraying me. I heard latex gloves snap, metal clinking, her boots pacing. Time stretched until my legs shook.

“Turn around.”

She sat on the bed like a queen on a throne, a thin wooden paddle across her lap.

“Crawl.”

Carpet burned my knees. I kissed her boot without being told. She let me. Then the paddle hooked under my chin, forced my eyes up.

“You paid for two hours,” she said. “In two hours you’ll hate me. And you’ll thank me for it. Open.”

A red ball gag filled my mouth before I could answer. Drool started instantly.

She kicked my knees apart until my balls nearly touched the floor. “Ass up. Forehead down.”

The first crack of the paddle was a gunshot. No warm-up. Just pure fire. I screamed into rubber. She grabbed my hair, yanked me back.

“Stay.”

Another. Harder. Then a rhythm—slow, surgical, merciless. By twenty, I was sobbing snot and tears into the carpet. She never spoke. Just painted my ass with agony like it was her job.

She pulled the gag half out. “Color?”

“Green,” I rasped. “Please don’t stop.”

First smile. Feral.

“Good boy.”

She threw me over the foot of the bed, cuffed wrists and ankles wide. My cock leaked a puddle on the comforter. She noticed and sneered.

“Pathetic.”

Belt buckle. Not mine—hers.

The first lash wrapped my hip like fire. She adjusted and striped me perfectly. Thirty times. I lost language. Just animal noises and pleas for more.

Then the cane. Six perfect tramlines. On the sixth I came untouched, shooting ropes onto the hotel bed while my body convulsed in the cuffs.

She flipped me onto my back, straddled my chest. Her pussy an inch from my face, covered in black lace, wet and musky. She grabbed my throat.

“You don’t get to taste me tonight. But you’ll watch.”

She fucked herself with two fingers right above my face while slapping my balls raw. When she came she clawed my chest until I bled, moaning like a demon.

Afterward she smoked a cigarette and watched me shake in the cuffs like I was art.

“You’ll book me again next month,” she said.

“Yes, Mistress.”

“And the month after.”

“Yes, Mistress.”

She uncuffed me, handed me water, traced the welts with one finger while I whimpered.

“You’ll sit on this for a week and remember who owns you now.”

Nine days I couldn’t sit. Ate standing at my desk. Jerked off in the office bathroom remembering her belt, her taste of leather still in my mouth.

That was six years ago.

I’ve been back every four to six weeks since. Hairbrush until I bawl. Sjambok that cuts. Hours kneeling ignored while she watches TV. Once she pissed on me in the shower and I thanked her for it.

This is real femdom spanking. Not the pretty gifs. Not the porn where everyone smiles.

It’s ugly. It’s humiliating. It hurts like a motherfucker. You cry. You piss yourself. You beg for shit you can’t say out loud.

And it’s the only time I’ve ever felt truly alive.

If your hand is between your legs right now, or your throat is tight because you know exactly what I mean—stop waiting.

Book the session. Send the tribute. Knock on the door.

Because the second it closes behind you and you realize there’s no escape, that’s when you’ll finally breathe.

I was ashamed once.
Now every stripe on my ass is a badge.
Every tear over a woman’s lap is a prayer answered.

And I’ll keep crawling back—wallet open, ass up, mouth shut except to say thank you—until the day I die.

Because this raw, filthy, brutal surrender is the only truth I’ve ever known.