(M/F) A costly mistake leads to a painful lesson.

I was running late for a lecture when it happened. The Porche in front of me hit the brakes suddenly and I was just slightly too close. I skidded agonisingly then with a delicate “crunch” came to a stop.

“Shit!” I said and got out to inspect the damage.

Surely it couldn’t be too bad.

An attractive blonde, maybe mid-30s emerged from the Porche, looking not surprisingly quite unhappy.
“Are you okay?” I asked anxiously.

She adjusted the jacket of her charcoal business suit, which truth be told, fitted her extremely well.
“Yes, I’m fine, you hardly touched me. Let’s hope there’s not too much damage.”

“Sorry, I was too close, I’m running late.”

Ironically, the bumper of my clunker was barely dented, but the back of her car was going to need some serious work. My heart sank.

“Well that’s not going to be cheap. I hope you’re insured.” She said.

I wasn’t, and as a university student there was no way I as going to be able to pay for the repairs.

“Right,” she sighed. “I live just around the corner. Follow me there and we’ll work something out.”

I pulled up outside an elegant two-storey house in a leafy street. Great, I thought, you don’t get rich without being generous with money. This was going to cost me.

I followed her pleasantly-filled pencil skirt up the walk to her front door.

“My name’s Andrea.” she said, ushering me in and heading for the kitchen. “Let’s have a pot of tea and get this sorted.”

“Dan.” I said. “Tea would be nice.” I didn’t usually drink tea, but now was not the time to be difficult.

I sat as she put the kettle on. She really was gorgeous. Honey blonde, wide-spaced blue eyes, great body with two medium-sized but shapely breasts straining her purple business shirt. She reminded me of my english teacher in high school who everyone had a massive crush on. My hormones waged war with my feelings of dread about the car and I shifted a bit on my seat to ease my growing erection.

“Milk?” she asked , glancing humorously towards my pants region as if she knew exactly what was going on down there.

“Thanks.” I croaked.

“So Dan, you’re a student?” Andrea asked as I awkwardly sipped my tea.

We made some small talk about the university. She was a graduate from there with a degree in business administration. We finished our mugs.

“Well Dan, what are we to do? You aren’t insured and you can’t afford to pay for my repairs, and you ran into the back of me so there’s no argument about whose fault it is.”

“I’m so sorry Andrea. I have a part time job. I can pay you off in instalments…”

We both knew that would take forever. There was a long silence. For the first time Andrea looked uncomfortable.

“Look Dan, I have an idea. You damaged my rear end, so… wait here a minute.”

She disappeared upstairs and returned a few minutes later looking flushed, holding what was unmistakably an extremely mean-looking crook-handled cane.

She placed it on the table between us and said, a little breathily “You damaged my rear end, so I’d like to return the favour.”

I felt a surge of adrenaline in the pit of my stomach. My hands trembled as I reached for the cane and slid it toward myself.

“You want to… give me a caning?”

“Yes Dan. it’s…” she smiled and leaned forward, back in control of the situation, “an interest of mine. Sadly, it’s been a while. Anyway, how I see it is you’ve done wrong and you need to atone somehow. Say… twelve of the best and your rear end, a bit of discomfort, well, a LOT of discomfort if we’re being honest and we’ll call it all square. I’ll pay for the repairs to my rear end and I’ll even rub a bit of lotion on yours afterwards if you like. No lasting harm done. What do you say?”

I picked up the cane. It was about a metre long and under a centimetre thick. I swished it and it made an alarming “whoosh” as it whipped flexibly through the air. I tapped the palm my hand with it. It stung, and I imagined it crashing into my backside at high speed.

Fuck.

Andrea grinned at me. We both knew I had no choice.

“Okay, fair enough.” I said. “Not too hard though, please.”

“Oh it’ll be hard, it is a punishment after all. No point if it doesn’t sting a bit!” she said, reaching for the cane. “Stand up!”

Oh shit. For some reason, this gorgeous woman’s threat to beat me with a cane had given me a raging hard-on. I hesitated.

“Don’t worry about hiding what’s going on inside your jeans! You’ll be stark naked in a minute!” She rapped the cane on the table and I jumped out of the chair slightly awkwardly, my cock a bar of steel.

“You heard me, everything off!” she barked and flicked the cane at my hip. Ow! That thing stung.
I hesitated again.

“Make me wait and I’ll make it eighteen!” she said, flexing the cane happily. “Suits me.”

I fumbled at my buttons, stripping naked in front of this lovely woman I had just met. I finally stood, naked, covering my erection which hadn’t subsided in the least.

“Hands on your head!”

I reluctantly complied. My dick pointed straight to the ceiling. She tapped it gently with the cane and laughed when I flinched.

“Don’t worry.” she said, shrugging off her jacket. Her nipples were standing out hard through her silk shirt. She started a slow lap around me, like I was under inspection. “This is for your backside.” And she punctuated the word with a sharp slap to my ass. It stung then tingled. Fuck, this was crazy.

She stepped back around the front, her heels clicking on the floorboards, and put her hands on my face and looked me in the eyes. I shivered.

“This is going to hurt, and you deserve it. I’m going to give you six, then you can have a break, then you’ll get the last six. You can yell, but please don’t scream too loud. We’re pretty far back from the road.”

The sun shone through the kitchen window, but it was private as the view was obscured by bushes.

Nobody was going to see my caning except Andrea.

This strangely reassured me and under the fear, I felt a surge of intimacy. This woman was totally in control of me for the next few, no doubt excruciating, minutes.

“I am going to hit you hard, but I promise I won’t cut you, no matter how painful it feels. You’ll be bruised and reminded about what happened every time you sit for the next couple of weeks but there will be no lasting harm and no hard feelings on my part.”

She continued to stare into my eyes until, in a daze, I nodded. She let go of my face, dragged a chair out into the open and said. “Okay, it’s time to get started. Put your hands on the seat and arch your back.”

Her eyes were dancing with excitement as I bent and offered my bare backside to her, heart beating rapidly. She adjusted my position, making me shuffle awkwardly til she was perfectly satisfied.

“You might want to grip the sides of the seat. If you get up, I’ll add a stroke. If you wiggle around too much, I’ll add a stroke. Understand?”

I grunted, just wanting it to get started now.

“Please say ‘yes Andrea’ if you understand.”

“Yes Andrea.” I croaked.

To my left I saw her kick off her black shoes. The sight of her bare feet on the floorboards somehow made the situation seem all the more bizarre. The cane tapped ominously n my buttocks.

“Try to relax. It will bruise less.”

I tried to relax. The cane drew back. A pause. I could still get up. I could stop this. I could work something else-

A swoosh.

Too late.

CRACK!

Bizarrely for a moment there was no pain, then
“FUUUUCK!” I screamed. I jumped up and clutched my bottom, jumping on both feet, my erection disappearing and flopping up and down. I turned beseechingly to Andrea, realising I was due for an extra stroke when I couldn’t imagine bending over for even one more of those.

She grinned as my frantic rubbing made my cock flop up and down. “Oh dear, looks like you’re getting an extra one already!” She tapped the seat of the chair and commanded “Over you go, and do try and hang on this time.”

Seeing there was to be no mercy, I tried to pull myself together. My fingers gingerly felt a weal forming right across the centre of my buttocks. Andrea gazed at me impassively, lips quirked. I had no choice. I turned. I bent. I gripped the seat. Hard.

Tap tap tap.

Pause.

Whoosh CRACK!

This one was well above the first. I shouted like a wounded bull and drummed my feet, but hung on to the chair.

Tap tap tap.

Longer pause. Oh just fucking get on with it you bitch.

Whoosh CRACK!

This one hit me right in the crease where my legs met my arse. As the white fire from the pain died down and I steading myself for the next cane stroke, I pictured my bottom with three widely spaced parallel lines. ‘Fuck she’s going to fill in the gaps!’ I thought and nearly giggled before.

CRACK!

CRACK!

“FUCK! FUCK! FUCK!”

She struck me twice, fast, hard and closely spaced. I barely managed to stop myself from jumping up and instead actually did giggle madly as I pictured her filling in the space between the two top marks.

“Oh think it’s funny do you? Okay, I’ll lay them on a bit harder.”

I saw her feet shuffle back slightly.

“NO NO!”

WHOOSH CRACK!

“OWOWOWOWOWWW!”

This was the hardest stroke yet. I drummed my feet, my knuckles white from gripping the chair. Her fingers gently stroked my striped bottom, tracing the weals she had caused to rise.

“You’d be halfway done now if you hadn’t got up.
Time for your extra stroke. Stick it out please.”

I did my best, resigned. She tapped the space just above the last stripe.

“Brace yourself.”

WHOOSH CRACK!

When my dance of pain had finished, I noticed she had seated herself.

“You can stand.”

I stood, ever-so-gently caressing my welted behind. She poured herself another cup of tea from the pot and gestured to mine. I shook my head.

“Come on, you could use a cup of tea after that.”

‘After that’! Like it had nothing to do with her beating my ass with a cane! Well it might put off the second session a bit.

“Sure, thanks.”

“Take a seat.”

“I’ll stand if you don’t mind.” She smiled and handed me my mug.

The incongruity of us both quietly sipping our tea after the madness of the last few minutes struck me and I started giggling again, which set Andrea off and we both started laughing so hard I had to put my tea down to avoid spilling it.

After a beating and then a good belly laugh I felt a strange calm descend over me. The sweat on my body was cooling and the lines of fire on my arse settled down to a steady general burning.

“I don’t suppose this means you’ll let me off the next six?” I asked hopefully.

Andrea laughed again and said “‘Fraid not, Dan. You’re over halfway there as long as you don’t jump around and I’ll let you in on a secret – I’m quite enjoying this.”

“Well I’m not.”

“Come on, you earned it. Imagine the pain of me paying for my own repairs if that helps.”

“Yeah, that will be a huge help. Do you have any idea how much this hurts?”

We smiled at each other and I suddenly realised we were flirting! This sadistic bitch had just caned me and was about to do it again, and we were sipping tea and having a laugh about it! My penis started to respond to the situation in the only way it knew how.
Andrea’s eyebrows rose. “Well, looks like some part of you’s looking forward to the second half!”

I blushed. “Please! Seriously Andrea, it really hurts!”
“Sorry Dan, a deal’s a deal. Finish your tea and we’ll get this over with.”

“Can I use the bathroom first – the tea..?

“Okay, can’t have you wetting yourself. Up the stairs and first on your right. Be quick or I’ll add another.”
I took the stairs, my erection bobbing. My state meant it took some time to empty my bladder. I hurried back down and she tutted.

“Oh dear, looks like you’ve earned an extra stroke Dan.”

I couldn’t bear it. “No, please Andrea!”

“Okay. come here. Face me. Hands on head. Don’t make a sound.”

She took my nipples between her index finger and thumb and squeezed hard this new pain shot straight to my groin then she twisted and doubled the sweet agony. She held my gaze then unexpectedly kissed me on the lips, slipping her warm tongue into my mouth, then let go of my nipples and stepped back.

I was drunk on sensation and dazedly followed her instructions to resume the position.

She waited, tapping my bottom with the cane as I returned to my senses.

“Okay Dan, I’ll let you off that extra one. Six to go. You’ve done amazingly so far. Hold tight.”

Tap tap tap

WHOOSH CRACK!

My bottom, which had settled down to a surprisingly pleasant sting erupted in pain again. I nearly jumped up in surprise but stopped myself.

“One.” She said.

Tap tap tap

I was in agony, but at the same time, I could not remember feeling more alive.

WHOOSH CRACK!

“OH GOD ANDREA THAT HURTS!”

She placed her hand gently on my bottom and bent to whisper warmly in my ear. “Okay Dan, I’m going to give you three in a row now. It’s going to hurt, but don’t move as you wouldn’t like it if I missed. She kissed my cheek and withdrew.

Tap tap tap.

Tap tap tap.

CRACK! CRACK! CRACK!!

I screamed but didn’t let go, sinking to my knees instead. She allowed me maybe a minute to sob, then tapped my arse warningly.

“Get up Dan. Last one coming up, and just a warning, the last one’s always the hardest.”

I straightened my legs. I saw her feet retreat from me and was momentarily puzzled, then realised ‘fuck, she’s taking a runup!’

Her feet skipped gracefully forward. I held my breath.
The cane made more of a ripping sound than a whoosh before it smashed dead-centre into my defenceless bottom.

I roared with pain and the chair fell to the ground as I danced wildly around the kitchen. I found myself babbling “please don’t give me an extra Andrea” and she enfolded me in a hug, then led me to the living room and lay me face-down on the couch where I slowly fell into a doze.

I woke to see Andrea sitting in a chair, watching me.

“Ah, back with us?”
I didn’t know what to say.

She held up a bottle of aloe vera. I nodded.

She knelt beside me, lifted the blanket she had clearly placed over me while I dozed and squirted cream on the damage she had inflicted on me. I gasped at the cold, then groaned with pleasure as she gently kneaded it into my bruised skin.

“It’s so hot.” She murmured, adding more cream. “I’m sorry I had to do that, but it did solve a problem, and I know it’s difficult to understand, but I really enjoyed doing that to you.”

“Feels so good.” I said.

“Sit up.” She said. “Time for your reward.”

I sat up and winced at the pain.

She chuckled. “Okay, stand up then.”

I stood, and so did my cock. She licked it
langourously from root to tip then took me warmly in her mouth, her head bobbing while her fingers tickled my welted backside.

I gripped her golden hair as an eruption built. She took her lips from my cock with a soft pop and to my horror said “and now, there’s only the matter of your extra stroke to be dealt with.”

As I started to babble a protest, she grabbed my balls with her left hand, cheekily licked the tip of my straining penis and SMACKED my ass with her right hand as hard as she could. Sensation erupted through my body and I came the hardest I ever had in my life, bathing Andrea’s face and shirt with ropes of cum as I erupted again and again.

My knees buckled and we ended up laughing in the carpet, her wiping her face with her finger and licking and swallowing every drop.

As we came back to earth, she looked ruefully down to her stained silk shirt.

“I ought to punish you for this?” She said, grinning.

“I’ve got a better idea.” I said, my cock beginning to rise again.

She smiled, got to her feet, and led me upstairs to the bedroom.

Source: reddit.com/r/eroticliterature/comments/nlrxkx/mf_a_costly_mistake_leads_to_a_painful_lesson