"Buy me one of those."

An attractive woman, maybe mid-thirties slid into the stool next to me at the hotel bar. She was dressed in an immaculate black business suit matching her dark, slightly curly hair, and carrying a long thin leather bag. She caught me glancing at her thighs as her slightly too short skirt rode up and quirked her lips at me.

"Well?"

I signalled to the barman for another two single malts.

"Here for the conference?" I asked in a weary tone.

"Long day?" she asked, sipping her drink and closing her eyes appreciatively.

"Well yeah, it's a boring job, but it pays the bills." I sighed. "Then I was drinking alone in a hotel bar, but things suddenly started looking up. You?"

"Just got stood up, actually."

"Bummer."

She finished her drink and gestured to the barman, "Another?"

"Sure."

Things were definitely looking up.

She was a fascinating lady, though I was aware that I was mostly talking about myself and how uninteresting I found my job and conferences in particular. Erica was quite evasive about herself, so I decided a direct question might get her to open up a bit.

"So what's in the bag?" The oddly shaped bag was propped up against the bar.

"Work tools."

"Work tools?"

She took a lingering sip of her fourth whisky for the evening. I do love a woman who loves whisky.

"Do you really want to know?"

"Sure."

"Canes," she said. "I have canes in my bag."

I was about to ask the obvious question and she leant forward and murmured in my ear. "I cane men on their bare bottoms for a living."

"Well," I croaked, my throat suddenly going dry, "That certainly sounds more interesting than my job."

"Sometimes women too, to be honest, but mostly men. I specialise in business conferences, actually. Business types seem to be into this sort of thing, and canes tend to be a lot quieter than... other implements. Bit more hotel friendly. As long as there's not too much screaming."

"I can see how that might be an occupational hazard. Would certainly relieve the boredom I suppose."

I couldn't take my eyes off the bag.

"Yeah, though my client chickened out this evening, so I'm feeling a little frustrated. Still paid his bill though, so there's that."

"So you enjoy..."

"Caning arses? Oh hell yes. You certainly get to see a different side of people."

"Literally and figuratively," I said.

She laughed. "Quite. Seriously though, it's very real, and quite cathartic for all involved."

For the first time in the evening, there was an awkward pause in the conversation.

"Okay." She said.

"Okay, what?"

"Don't play innocent. I know you're wondering. Yes, I'll come upstairs and cane your arse for you."

I paused. Yes, I was. My whole body was flooded with adrenaline.

"This isn't a business arrangement if you're worried. I've already been paid tonight. Consider it a friendly caning."

She put her hand on mine and grinned evilly as she could felt it shake slightly.

She pulled me towards the lifts.

"Don't forget your bag," I said.

We waited for what seemed like an age for the lift, her hand resting proprietorially on my ass. The ass she was about to cane. She glanced down at the rising tent in my trousers.

Ding! Went the elevator.

"Saved by the bell." She murmured and pushed me gently inside.

"You're pretty quiet. You're not going to chicken out on me too are you?" She asked as the doors closed. "I really need to give somebody a sore ass tonight."

She grabbed my tie and pushed me against the wall. 

"I'll be honest, I do it for the money, but I'm a kinky girl - inflicting a little pain on a consenting adult turns me on, and what turns me on, even more, is that adult taking it well. So let's make it interesting: take your caning like a man and you're in for a hell of a night."

She kissed me hard, and I tasted whisky on her tongue, then she reached up and twisted my nipples, hard, sending a jolt of energy through me. I couldn't quite believe how completely this woman had taken control of me.

The doors opened and I led her like a zombie to my room. She got a couple of whiskies out of the mini bar and sat on the bed, "Dutch courage for the condemned man? Settle your nerves. Actually, take off your clothes first then I'll talk you through what's going to happen."

We both took off our jackets then she crossed her gorgeous legs and watched me take off everything else. When I was standing naked, hands cupped over my erection, she patted the bed beside her and handed me my drink.

She slid a wicked-looking cane out of her bag and handed it to me. It was surprisingly supple.

"Okay, my executive service is 12 good whacks with this on the bare ass kneeling on the bed, or for the novice, six lying down. As it's your first time - and it is your first time, isn't it?"

My throat was dry, so I just nodded, not trusting my voice.

"As you're a novice, you can take six lying down. After that I'm usually off to my next appointment, leaving the poor businessman to finish his business on his own, but this is off the books and if you're good... you know the deal."

"I'm all about my boys taking their punishment, so there's no warmup beforehand. I'm going to cane you once every thirty seconds to let the full effect sink in. It will hurt like hell, but will all be over in three minutes. You'll have six raised stripes on your ass afterwards, and you'll remember me every time you sit down for a few days, and you'll probably be bruised for a couple of weeks."

Her fingers were gently stroking my erection as she matter-of-factly explained how she was going to inflict my punishment.

"Your job is to lie there and take it well. Occasionally I break the skin, but usually not. I promise you won't be permanently damaged. You've heard of a safeword?"

I nodded.

"Well we're not roleplaying, so if you say "stop" I'll stop straight away, though that means there won't be any of this afterwards." 

She bent down and gently enclosed the head of my cock in her warm mouth. 

"All clear?" 

I nodded. She smiled brightly but said "Good, but you need to say it. Say "Please cane me, Erica."

"Please cane me, Erica." It came out surprisingly convincingly.

"Good boy. Stand up."

I followed orders. She placed some pillows on the bed and held out her hand for the cane. She tapped the pillows with it.

"Assume the position."

She got up and dimmed the lights as I arranged myself for punishment, bare bottom in the air, hard-on pressing into the pillows, head cradled on my folded arms. "Bare Bottom," I thought to myself and almost giggled at the absurdity of it all, but then Erica steadied herself, tapping the cane gently on the target.

She lifted the cane, paused, stared intently, then whipped it down with a surprising viciousness.

THWACK

I was just able to think "wow, a cane hitting my ass really does go "thwack" when the pain hit me. Wow, that really fucking hurt! My body jerked involuntarily, and I curled my toes and hissed through my teeth.

"One," she said. "Try not to move too much."

I lay there as the line of fire across my ass slowly cooled. Five more of those.

THWACK

"Two." 

I grunted. My erection was gone. This really fucking hurt. I could make this stop. Why was I letting her do this to me?

She adjusted her skirt; she put a bit of hip into her stroke. Our eyes met, and we shared a moment that she really was enjoying causing me pain. There was a challenge in her gaze. Pride made me nod gently to continue.

THWACK

"Three."

I made a sort of involuntary UHHH noise. I straightened my body into a perfect plank against the pain.

"Keep still, please. I'm going to give you two in a row."

"Wha-" I thought.

THWACK

"Four."

THWACK

"Five!"

I gave an utterly embarrassing squeal, and my hands shot to my ass. The pain was shattering. The heat of my skin was incredible. I writhed on the pillows.

"One more." She said.

She waited until I was still. Amazingly, I felt my cock stir. I had adjusted to the overwhelming pain, and this was starting to turn me on again. Our eyes met again, and I stuck my burning ass out for the last stroke. Her lips quirked, then her eyes went back to the target, and I braced myself.

THWACK

It was the hardest one. I shouted "FUUUCK" into the pillows to muffle the sound.

Erica sat on the bed, her fingers idly tracing the raised lines on my ass as I tried to control myself. 

"How was that?" I asked, which immediately struck me as ridiculous, but I was worried I hadn't taken it as well as she hoped.

"You took it like a man." She proclaimed, then smacked my raw ass hard with the flat of her hand. While I was gasping at the unexpected reawakening of pain, she started unbuttoning her shirt.

At an imperious gesture from her finger, I rolled over, gritting my teeth at the contact with the sheets, but drinking in the glory of her naked body in the dim light of the room, my erection reawakening as the pain transformed into a warm, slightly scratchy throbbing.

She crawled catlike onto the bed, gave my hard-on one long, languorous lick, stiffening it to iron, then climbed on top of me and sheathed my cock inside her glorious hot wet cunt.

This was definitely the most interesting conference I had ever attended.