It was around midnight on Friday and I was trying and failing to catch the bartender’s eye when I felt a firm whack on the seat of my jeans. I turned to see Andrea’s grinning face.
“What are you having?” she shouted above the band. Her face was flushed in the heat of the packed pub. I pointed to my preferred ale and she immediately ordered two, having no trouble getting the bartender’s attention with her blonde hair and tight purple silk shirt, unbuttoned to reveal generous cleavage.
“Got my bumper fixed!” she said, referring to where I had run into the back of her car six weeks earlier. She patted my backside proprietorially, “How’s yours?”
It had been six weeks since she had taken down my pants and thrashed my bare bottom with a cane to make up for my lack of insurance. It had taken about three and a half weeks for the bruises to fade completely. I had checked every morning in the bathroom mirror and then wanked myself off. The memory of the searing pain had become fonder over time.
“It’s f-fine thanks,” I stammered, my face flushing too. I hadn’t seen her since. She was a professional older woman and I was an undergraduate so our paths didn’t cross and wanking off at the memory aside, I still wasn’t sure how I felt about this woman brutally
caning my arse.
She grinned at me again. I think she was a little bit drunk. I certainly was. I could feel heat radiating off her. We sipped our beers at the bar, Andrea searching my face with that slightly mocking grin. About halfway through, she leaned forwards and put her lips to my ear. I felt her hot breath as she whispered, “Coming then?” then licked my earlobe wetly.
My hand shook and most of my beer spilled. She laughed, downed the remainder of hers, took my hand and led me out of the bar.
“If you come inside I’m going to cane you again.” She whispered in my ear as the cab pulled into her street. “Just here thanks,” she said more loudly to the driver and tossed him some cash.
She opened her door.
“Coming?”
My legs were jelly. I could just stay in the cab and go home, backside undamaged.
Fuck it. I lurched out of the cab and followed her tight black skirt up the path to her door.
Inside she turned and kissed me hard, hands gripping my buttocks. “Strip and stand in the corner with your hands on your head. If I get back and my instructions haven’t been followed, you won’t like it.”
She disappeared up the stairs. I took off my clothes and contemplated the corner, my fingers gently stroking my naked backside. I remembered how much her cane had hurt the last time. That was payment for damaging her car. I owed her nothing now and could just walk out the door, I thought. I stripped and stood in the corner, hands on my head feeling a complete idiot. I entertained myself by touching the tip of my hot, throbbing erection to the coolness of the wall.
“Are you fucking my wall?” Andrea laughed. I turned. She had removed her shirt and was clad in black bra and her tight black skirt and was gently flexing the same cane she had used on me last time.
“I was -” It was too hard to explain. “Let’s just get on with this. How do you want me?”
“All business huh?” Andrea laughed again. She was certainly in a good mood, which I hoped was a good thing. She strode forward, grabbed my cock and pulled me towards her couch.
“Kneel on the seat, lean over the back, stick your arse out.”
I did as instructed. She walked around in front of me and took off her bra.
“Oh fuck.” I feasted my eyes. She leaned forward and I took a nipple in my mouth. She shuddered and put her hands in my hair.
“Oh Dan, I’m going to make you scream.”
She disengaged her nipple and her bare feet padded on the carpet as she positioned herself to my left. Tap tap tap, I felt the cane on my bare buttocks. Tap tap tap. She rested it lightly on my unblemished skin. It was cool and hard.
“A dozen I think,” she murmured.
Swish swick!
A line of fire across my arse. I gasped, crazily thinking how different a cane striking my bottom sounded in a carpeted loungeroom compared to last time in the floorboarded kitchen. That thought was blown out of my head by a second swick! across my arse.
I thought I’d remembered the pain, but it was far worse than I had braced myself for.
Swick!
Swick!
“Fuck! Andrea-“
Swick!
That one was extra hard. I took the hint and tried to stay silent.
Swick!
Another hard one right on my sit spot. I jerked and grunted. Andrea’s hand gently caressed my now-welted behind.
“That’s six. Get up.”
I stood shakily. Her skirt whispered to the ground. She was naked. She lay on the couch and spread her legs wide. The invitation was clear.
My cock rose and I mounted her, my cock sliding gloriously into her hot, wet cunt. I started thrusting slowly.
“Harder!”
I pumped my hips. She pulled my face to hers and kissed me hard, our tongues entwined.
“You still – ahh – have six – ohh to go. If you come, it will hurt – uhh – twice as much.”
She grinned at me evilly as I fucked her. She knew I was close. I knew she was right. With more self-control than I knew I possessed, I pulled my cock out of her velvety cunt and stood, my arse burning, my penis hard as rock.
“Smart boy,” she murmured, fingering her pussy, then rose gracefully to continue my torture.
“Grab your ankles this time.”
I bent, feeling utterly vulnerable and off-balance mentally and physically.
Tap tap tap. My arse was taut in this position. My hard-on poked into my stomach.
Swick!
“Oh my god!” It hurt even more in this position.
“Count them.”
“One.”
Swick!
“T – two.”
Swick!
Oh the pain! It was at a crescendo now and I swayed. Andrea’s hands gently steadied me.
“Don’t want you falling and hurting yourself,” she said.
“Thanks,” I replied to the woman caning me.
She patted my flaming behind.
“Ready? We’ll have to do that one again as you forgot to count.”
“What? You bitch!”
CRACK! She spanked my right cheek hard, igniting the cane-welts.
“Ready, Dan?”
“Ready.” My surrender was complete.
Swick!
“OH! Three.”
“Last three are going to be fast. No need to count. Try to hold still.”
I felt the cane tap high, middle and sit spot. She was lining them up. I tried to relax, to anchor myself.
Swick! Swick! Swick!
I screamed, clapped my hands to my cheeks and jumped round the room like a rabbit.
Andrea drunk it in with that lopsided grin. She really got off on this. So do you, I thought to myself.
She got back on the couch.
“Well done, Dan, now when you’re quite ready, come and fuck me.”
I climbed on top of Andrea and pressed my quivering cock into her and soon was jackhammering her pussy. She arched her back, coming, her fingers raking my raw buttocks, sending white lightning straight to my groin. I came hard into her, hot semen boiling out of me again and again as she writhed under me.
I awoke in her bed, lying on my stomach, Andrea’s fingers idly tracing the welts on my arse.
“Stop that.” I pushed her arm away.
Whack!
“Fuck Andrea! That hurt!”
“Sorry, but there’s the matter of you jumping up before I said you could last night to deal with…”
“Oh come on, Andrea, I think you’ve beaten me enough for one weekend,” I complained, but my growing erection betrayed me.
“Do you want me to fetch the cane or shall I take care of it now with six with the hand?”
“Hand.”
Jesus, what was I turning into?
“Hold still.”
She got to her knees. She put her left hand in the small of my back and lifted her right high. She was naked and her breasts were golden in the morning sunlight.
Whack! Whack! Whack! Whack! Whack! Whack!
Fast and hard. The sting on my already damaged bottom was incredible. I writhed on the bed in pain and growing excitement.
I felt her lips kiss my burning arse.
“There we are. All square. Good boy.” Her tongue licked a warm, soothing trail over my skin. She rolled me onto my back and impaled herself on my cock.
This was going to be quite a weekend.
