Brutally Erotic Caning Stories That’ll Make You Cry

Ever heard the joke by Emo Phillips? “You don’t appreciate a lot of stuff in school until you get older. Little things like being spanked every day by a middle-aged woman.”

That joke perfectly sums up some of the most brutal caning stories I’ve ever experienced in my life, the most hardcore of which I will share with you today.

Corporal punishment in Northern Irish private schools was only abolished in 2003. I’m old enough to remember being thrashed as a form of punishment.

At the time, it was one of the most horrendous things I could imagine, and I tried my best to suppress the memories of being caned until I cried my eyes out and begged for mercy.

I’d been caught fighting with another girl before being dragged to the sadistic headmistress’s office, where we were both thrashed and sent home distraught.

Little did I know that a seed had been planted at the time. Over a decade later, I’d be voluntarily seeking out corporal punishment. The caning stories of my life were far from over.

Kink Porn Awakens a Deep Lust For Corporal Punishment

As the camera panned into the weary, swollen, and bloodshot eyes of the 20-year-old BDSM submissive sucking a ball gag on screen, she was begging for mercy. But she received none.

The cane sliced through the air like a knife and obliterated what was left of her young ass as she wailed and flailed wildly, hopelessly unable to move in the tight shibari rope that bound her.

I’d been edging to hardcore BDSM porn and fetish cams for the past twelve hours on Kink.com. Naturally, memories of my own caning experience began to surface in my Porn-riddled mind.

“I… I fucking hate you”, I grunted through gritted teeth as my pussy gurgled with the sweet fluids of female ejaculate.

But rather than force them away like I was used to, I revelled in them and masturbated to the memories of being turned into a pathetic, snivelling bitch begging an older woman for mercy.

I wanted to cum, but I made a fateful decision instead. I was going to seek out a disciplinarian online and submit to them for the chance to relive my corporal punishment experience.

Setting my search filters on the Ashley Madison hookup app to BDSM, Fetish, and Corporal Punishment, it didn’t take me long to find what I was looking for.

Mistress Helga: A Sadistic Dominatrix In London

Her name was Helga. A German Domme who’d lived in the UK for fifteen years, she was a sneering woman in her mid-40s with jet black hair and a buxom chest bursting out of latex.

She was naturally beautiful and oozed assertiveness, but her eyes projected an unmistakably sadistic streak. My hands rattled as I typed my message due to nervousness and lust.

“Dear Helga, I recently came across your AFF profile and instantly felt the urge to drop to my knees. I’m a dedicated kinkster but have only recently discovered a newfound desire for corporal punishment. I would like to request to submit to you humbly. With utmost respect, Catherine.”

To my disappointment, Helga left my message on read for four days. But finally, her response came through and was even more sadistic than I’d hoped.

“I’ve just perused your website to discover you’re quite a mischievous little whore, aren’t you? Usually, I aim for the sweet, innocent, and naive type of female subs. However, I feel it would equally pleasure me to punish you for a lifetime of whoredom. A bonus of cheap guttersluts like you is their inbuilt tolerance to the more extreme levels of BDSM. Should you accept, your appointment is Friday at 9 pm. Do not be late.”

Helga’s message made me weak at the knees. I had less than 24 hours to prepare and no idea what to expect. Regardless, I shaved my body all over and douched myself.

The Second Installment Of The Caning Stories of My Life Begins

In a leafy suburb on the outskirts of London, open my Ashley Madison app to confirm the address.

It was a large, gated house with the lower floors obscured by hedgerows. I parked opposite and could see the curtains twitching on the upper floor.

“I see you, whore.” Helga’s latest message read, “come to the gate, and we’ll let you in. Once you’re in, on your knees and crawl to the front door. Don’t worry, the neighbours can’t see”.

I hurried across the street with my high heels snapping through the quiet night. The cold winter air snapped between my legs and tickled the dampness of my slit.

Inside, my heart sank. Between me and the door was a gravel driveway topped with a range rover and an Audi. But I did as I was told.

The agonizing crawl to the front door took me five minutes. When I reached it, my ears were filled with tears. Wiping them, I looked up to see Helga open the door.

My eyes went from her shiny black heels, past her muscular legs clad in black leather pants and up to her large, natural bust bursting out of a latex corset.

Helga was looking down at me, disgusted. “You’re late”, she said in a harsh robotic tone tinged with a German accent, “get the fuck up and come inside”.

I was bang on time, but the unexpected task of crawling over harsh gravel had delayed me. I didn’t dare argue with her. Besides, I was hypnotized by her MILF ass swaying in black leather.

Helga opened a black metal door leading downstairs into an underground lair. This is it, I thought to myself and hesitated to enter. “Fucking move, you scum cunt!” Helga barked.

Helga had fittingly adopted her cellar as a BDSM dungeon. Complete with everything from a Queening stool and strapon bench to a headmistress desk and a St. Andrew’s Cross.

“Strip naked and get on your knees, harlot!” Helga ordered. I winced and let out a cry of pain as my destroyed knees connected with the concrete floor, “ohhh, stop snivelling. We haven’t even started yet!”

Helga inspected a long line of riding crops, canes, African Sjamboks, and other weapons of corporal punishment lining her wall alongside an array of sex toys and bondage equipment.

Helga took a seat behind her foreboding desk with a cane in hand; I was ordered to stand in front of her. I’d left my high heels and panties on at her request but was otherwise completely naked.

“Let me tell you something, you whore!” Helga laughed with her back to me, “you’ll come to regret all of your slutty boasts online. Life is a mixture of pain and pleasure. You’ve had quite enough of the latter; it’s my job to show you the other side of the coin”.

There Is No Alternative But The Cane

Helga sat in silence and glared into my eyes, subconsciously making me avert my gaze to the cold, unforgiving concrete floor.

“Look at me, cunt!” she roared with a thrash of the cane on her desk, “there is no alternative for you other than the cane. Do you know what they did to harlots like you in medieval times? Class yourself lucky, whore! Repeat after me: There is no alternative but the cane!“

I did as I was told. I chanted Helga’s mantra repeatedly and waited for her to tell me when to stop. But she didn’t. Helga smirked as I chanted moronically and manoeuvred behind me.

With a gentle push on my upper back, I was now bent over her desk and still chanting There is no alternative but the cane!

“Lie flat and drip the edge of the desk. Keep your ass up or face the consequences,” Helga grunted as my panties were yanked down by my ankles and my feet were kicked together.

My safeword set by Helga was humiliating and cunning: “Let me go, I’ve met my match”.

It was time.

The Caning of a Sordid Whore

Helga gently placed the cane against my bare cheeks like a woodcutter lined up with his axe. My heart was pounding out of my chest, and every part of my body rattled.

As the cold kiss of the cane released from my asscheeks, it felt like an eternity before it came back down.

*Swoosh! Thwack!*

I felt like a match was being held to my ass. I stifled my reaction so as not to encourage this sadistic bitch. But Helga knew what I was doing. I exhaled and prepared for the rest.

*Swoosh! Thwack!*

She targeted the line right this time between my ass and my thighs. I felt like my whole lower body was in flames. A third hit smashed into my upper ass as I tried to compose myself.

“Owwwww, fuckkkkk!!” I roared out as tears streamed down my face. The pain was excruciating.

“You fucking what?” Helga roared, coming around to be face to face with me, “you think I let subs use foul language in my dungeon? You pathetic little shitbag!”

A vicious slap knocked my face from right to left. As I turned to look back at Helga, she spat directly in my face before returning to her caning position.

Never neglecting a change for sleaze, I slurped her spit as it dribbled down towards my mouth. As I tried to swallow it, the fourth strike came across the centre of my buttocks, causing me to choke on it.

My legs buckled, and my feet spread either side of me before Helga violently kicked them back together. The sound of my heels scraping across the concrete filled the air, and my panties stretched to the point of tearing.

“Close your legs!” Helga barked, “you’re not in one of your sordid dens of sleaze now; this is a dungeon!”

Somehow, Helga could find the few sections of my arse that had been spared the wrath of the cane. Like a military general, she targeted each weak point until I collapsed.

Helga embarked on phase two when there was no fresh flesh left to destroy and began targetting the horrendous welts on my ass with secondary bites of the cane.

I wailed and cried genuine tears. The pain was horrific, and I’m not afraid to say that the safeword was on the tip of my tongue numerous times. But admit defeat and compromise my status of a whore to another woman? Fuck that!

The biggest test was one of Helga’s cruellest tricks. A *swoosh* cut through the air, but she stopped millimetres from my ass flesh.

Before I could even comprehend what was happening, a wave of joy and optimism flooded my body. Was she finally finished with me? I thought. Then, she struck like lightning with her hardest blow yet.

I felt the pain punch up my spine like I’d been hit by lightning. I stamped my heel-clad feet on the ground in a vain effort to distract from the pain. My hands clenched the wooden desk so tight I thought it would snap in two.

“Hands on your head!” Helga barked, “I’m sick of watching your filthy whore hands all over my beautiful desk”.

With nothing to hold on to, the caning was even more horrific. Over thirty minutes, my ass had been truly destroyed by her caning hand.

When Helga relented, I was in floods of tears and snivelling like a puppy. But the pause was only temporary.

“Don’t Ogle Me, You Porn-Addicted Little Pervert!”

“Time for a lie-down, whore,” Helga murmured whilst hanging up her cane and inspecting the others, “you’ve earned it.”

“Oh, thank you! Thank you, Mistress!” I grovelled whilst dropping to my knees and kissing her shiny black high heels as Helga looked down at me with hatred in her eyes.

“You fucking disgust me”, she grunted down at me, “do you have any idea where those heels have even been?” but I wasn’t deterred.

I sat on the BDSM bench Helga usually used for strapon fucking and felt the cold leather caress my raw asscheeks.

As I did, I admired the beautiful MILF body of Helga clad in her Femdom outfit. Then, she glanced at me and caught me ogling her enormous breasts.

“Who the fuck are you looking at?” She said aggressively whilst stamping a heel on the ground, “don’t ogle me, you porn-addicted little pervert!”

I was mortified and in terror that she would resume the onslaught on my ass. I couldn’t take anymore. When Helga stormed toward me, I was rattling with fear.

“Was it these you were looking at?” She said in an oddly calm voice whilst pushing her latex-clad tits into my face, “they’re all-natural, you know? If only you knew how many subs had submitted to me for the chance to see these”.

I meekly lifted my gaze towards them. These enormous milkers were now glazed in a thick layer of sweat and shining audaciously from their latex prison.

“You really want to see them, don’t you?” Helga smirked, “say, please give me twenty more lashes, mistress! I’ll reveal them to you”.

Bastinado

A logical woman would have said no. But my porn-addicted mind doesn’t run on logic. Despite the horror of twenty more, I blurted out what Helga wanted to hear and was being ordered back to the desk once again.

Thankfully, my ass was retired. Helga made me lie on my back and present my petite feet to her. She planned to finish me with a Bastinado foot-whipping session.

My heels were taken off and cast aside, and Helga ripped off my panties to stop them from getting in the way. Before chucking them across the dungeon, she huffed their scent deeply.

“As filthy as you harlots are, there are few things as beautiful as the scent of a whore’s cunny!” Helga said with a viscous, lusty tone.

The Bastinado that followed was agony but far from the level of the ass caning I’d received. My tears flowed during the lashes combined with the pressure of the wooden desk on my raw ass.

For every thrash, I had to thank Helga loudly for her severe abuse of my body. When we reached the 19th lash of the cane, I laughed uncontrollably at the thought of this being over.

“Almost there, sweetheart!” Helga laughed cruelly, “3… 2…” she interrupted herself by launching a mouthful of spit on my naked tits, “1!”

Rather than strike my feet, Helga launched an unexpected strike on my ass. I screamed, wailed, and cried louder and harder than I had all night.

As I struggled to cope with the pair, she grabbed my feet and smashed the final piece of the Bastinado session into the raw and burning soles of my feet.

“You’re screaming and crying like a pathetic girl, but your pussy is leaking!” Helga laughed, “there’s no level of filth you won’t make yourself wet over, is there?”

The pain was so bad that I felt sheer hatred bubbling up inside my body for Helga. So much so that I wanted to hit her for the agony she’d put me through. Then, I was given a reward.

Forced To Cum & Kicked To The Curb

I could hardly move for the pain. Helga hung up her whip and cleaned the sweat from my feet off its harsh leather exterior. Then, she slid her small hands into a pair of black latex gloves.

No sooner had the gloves gone on than Helga slid out of her latex corset to reveal a perky set of enormous natural tits.

As much hatred as I had for this sadistic bitch, I was immensely jealous of her breasts. They were simply divine.

“They’re better than you imagined, aren’t they? You’ve earned this sight”, Helga said proudly, “now spread your legs and show me that meaty twat!”

Hyptnized by her giant milkers, I did as I was told. My eyes were glued to her tits as Helga rudely slapped a layer of her spit on my wet pussy.

After rubbing my clit, she shoved two, then three, fingers deep inside me and targeted my G-spot before violently pumping my quivering fuckhole.

“How many dicks has this fucking thing swallowed up over the years, eh?” Helga laughed, “I just know you could take my whole fist. This cunt has seen some action!”

Helga’s strong arm pistoned up and down, and her giant tits bounced wildly on her chest. With my eyes fixed on them, she spat on her hand and rubbed her saliva all over them, creating a proper Porn Tits look.

I couldn’t hold it. I gripped my tits and stared at hers as my body began to convulse. The emotions running through me were wild. I was going to cum. Hard.

“I… I fucking hate you”, I grunted through gritted teeth as my pussy gurgled with the sweet fluids of female ejaculate.

“I know”, Helga said whilst looking me dead in the eye with a sadistic smile, “now spurt, you cheap whore!”

“Ngggghhhhaaaaaa!!” I roared as my neglected slit pumped Slit Gush down the front of Helga’s desk as I released a raspy, primal moan. The agonizing welts on my body felt immense in the throes of orgasm.

In a daze, I watched in a drunken-like state as Helga removed her soaking-wet latex glove and grabbed my discarded panties before soaking up the pool of squirt on the floor with them.

“Here, this will make it easier on you,” she said with a hint of sympathy, “hopefully it has a soothing effect when you’re on your way home”.

No sooner had I slipped back into soaking panties and got dressed; Helga was leading me to the door unceremoniously and opened it to reveal the cold, dark night that awaited me.

“Forgetting something?” she said aggressively, “and I’m not talking about your dignity. Say thank you”.

“Th- … Thank you, Mistress”, I said hesitantly only to see a dissatisfied look from Helga, “I deserved everything”.

Helga smirked at my final sentence and closed the door behind me without saying goodbye. I hadn’t been told to, but I knew the proper etiquette.

I returned to my knees and crawled back across the merciless gravel driveway to my car until I reached the gate.

The pain was compatible with the aftermath of a recent accident I had when I was hit by a motorcycle. I shuffled across the street as it began to rain, snivelling and wincing all the way.

When I got home, I collapsed in bed and nearly passed out from exhaustion. I had to lie on my front in bed to save myself from the pain.

The next morning, I opened up the Ashley Madison site, as I do the second I wake up most days, to find a message from Helga that read:

“You did yourself proud last night and took that punishment like a true champion. When you chose to crawl back along the gravel at the end? I was watching from the window and was so proud. My dungeon is open to you anytime you need to flagellate yourself for your sins. I’m sure I’ll be seeing you soon”.

Helga was correct. It wasn’t long before a sadistic lust drove me back to her front door again.

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Affiliate Disclaimer: The first of my caning stories may contain affiliate links to products or services that may have been used in the making of this story. When you purchase through these links, I can receive a small commission at no extra cost to you to help me keep running the site.