Anita sipped her coffee, then stared into it like she hoped it had some answers for her.

We'd been friends from way back at uni. There had always been chemistry between us, but other lovers, travel and jobs had always gotten in the way. We had both ended up in the same city with marriages and kids and were happy to be old friends and catch up for coffee or lunch every now and then.

I knew her pretty well. "What's on your mind?" I asked. 

She started then seemed to make a difference and gulped the last of her coffee.

"Can you come up to my office?" she asked.

I had nothing to do for the rest of the afternoon. "Sure, what's this about?" I asked.

"It's is a little... wait till we get to my office."

I followed, intrigued, as she led me to the elevator. She was average height, long dark hair, and kept herself fit. I couldn't help glancing at her gorgeous ass filling out her black office skirt. She noticed me checking her out in the lift's mirror and smirked at my reflection. I grinned back. She knew about the chemistry though we never spoke of it.

It was an awkward ride up to her floor. She seemed uncharacteristically nervous and clearly didn't want to talk.

Her office floor was empty. "Team-building exercises. I managed to get out of it." She said and ushered me into her office and closed the door. I took a seat on the couch. She went to sit in her chair, thought better of it and perched on her desk.

"Dan, just listen will you?"

I nodded. I know how to shut up.

"You're one of the few people I trust absolutely, will you keep what I'm about to say completely between us? No exceptions?"

I nodded, then realised I should probably say it. "Yes of course," I said.

"There's something about me you don't know. Nobody knows. I want... I want..."

She looked at me a bit desperately then went to a bookshelf and reached up to get something from the top. I couldn't help taking another look at her ass rather beautifully tightening the fabric of her skirt.

There was a wooden scraping sound and she brought down what could only be described as a cane. She turned to me, her face red. It was about three-quarters of a metre long with a crook handle at one end. It was a shiny deep yellow and maybe just over half a centimetre in diameter with a slight bend that made it look all the more wicked.

The die was clearly cast. 

"I want to be caned."

My first impulse to laugh or make a joke was quickly stifled by the seriousness on her face. She'd played plenty of tricks in the past and had a deadpan sense of humour, but I could tell she wasn't kidding. 

I thought for a moment, and decided to relieve a bit of the tension. "Well, at least you don't want to use that thing on me," I said. 

She smiled a bit weakly, "Dan, I've tried to talk to Nick about this but he won't do it. The best he can do is smack my ass while he's fucking me."

I shifted a bit on the couch as the image made my cock rise. She didn't seem to notice.

"Dan, for a long time I've wanted to know what it's like to be caned. I don't know why, it's always fascinated me. I'm not getting any younger and I need to know. Nick wouldn't do it and I don't want to pay someone I don't know, so..."

She was obviously a bit desperate. I'd never seen her flustered before.

"You want me to cane you?"

"Yes Dan, I know it's a lot to ask but it's - I don't know.. will you? Just once. No questions asked?"

I held out my hand and she passed the cane to me. I patted the other seat of the couch for her to sit beside me and she obeyed.

I tapped the cane firmly on my left palm. Wow! The thing stung. 

"So, do you want it on your, uh, hands or..."

"My bum, Dan! My bare bottom."

And with that, I felt a surge of adrenaline go through me. The thought of thrashing Anita's shapely bare ass filled me with a sensation of power I'd never felt and never expected to feel. 'Holy shit!' I thought, 'I really want to do this.'

The realisation that deliberately hurting one of my best friends turned me on so much was a little disturbing.

I must have been lost in thought because the silence lengthened and suddenly Anita struggled to get out of the couch saying, "Sorry, this is crazy! I don't know what I was..."

I grabbed her arm to prevent her from rising. That surge again, simply from taking charge. "No, Anita! I'm sorry, this was a lot to take in."

I looked her in the eyes and saw the embarrassment.

"I'm honoured that you trusted me enough and were brave enough to share this with me. Since we're being honest, the idea of caning you - willingly - really turns me on. Just so you know. Jesus this is unexpected! We need to talk about this first though. When do you want to do this? How much? How hard?"

She smiled weakly and took a trembling breath. "There's nobody here all afternoon. I believe six is the traditional number. I want it to be hard."

"It might shock you, but I've never actually caned someone before," I said, grabbing a cushion. "Perhaps I should take a few practice swings at one of these before I start whacking your - ahem - ass. Wheel out your chair for me."

She wheeled her chair to the centre of the room and I stacked up some cushion to the height I estimated her bum would be when she bent over. My cock stiffened at this mental image and I tried to hunch over to hide it.

"You're about to be caning my naked bottom, Dan. I'd be hurt if you weren't a little excited by the prospect." She glanced meaningfully at the bulge.

I tapped the top cushion with the cane and took on a mock-schoolmasterly tone. "Right Anita, this is your naked bottom after you have, uh, assumed the position. Prepare yourself, cushion!" She giggled.

I drew back the cane and whooshed it through the air a few times. It was extremely flexible and really did make a whooshing sound. I lined up the cushion and whoosh-WHACK! Anita and I had been on the tennis team together at uni and she knew I had a pretty good swing. She did, however, stop giggling.

"Hmm, maybe a little more gently to start off with." I used mostly my wrist this time and the cushion still got a substantial stroke.

"About that?"

Anita was transfixed on the cushion, her hands unconsciously rubbing her skirt. She nodded

I repeated the stroke a few times. It was easy to control at this speed, but it looked like it would still really sting. The sight of her mesmerised by the cane doing to the cushion what she was about to willingly subject her backside to was mind-blowingly sexy but at the same time troubling. Now it was becoming more real I was worried about hurting her.

She read my mind. "Look, Dan, I want it to hurt! I know it's a hard thing to get past, but please..."

She started unbuttoning her shirt.

"Hey, you don't need to take that -"

"Consider it a little bonus," she said, laying her shirt on the couch and unhooking her bra, letting her breasts bounce free.

"As good as you always imagined?" she asked cheekily, raising her arms and giving a twirl. They were gorgeous and she knew it, white against her tan and her small bright red nipples standing out like bullets.

I unashamedly drank in the view I had wanted to see for over twenty years as she dropped her skirt to the carpet and gracefully bent to pick it up. She dropped it on the couch and put her thumbs into the straps of her panties.

"No," I said tapping her ass gently with the cane. This got her attention and she froze, staring at the cane tip. "I'll deal with those when the time comes."

She gave me a genuine smile at this. "As you wish, sir."

"And I quite like you calling me sir for the purposes of this exercise."

"Yes, sir!"

I whacked her ass a bit harder with the cane.

"And that was for being a smartarse! Right, how are we going to do this?"

"I thought you could warm me up a bit."

"Do what?"

"Spank me a bit with your hand first."

"Okay," I said, trying not to sound too eager and failing.

I sat on the couch and gestured her to stand in front of me. She stood, trembling as I gently tugged her panties to her knees, revealing a neatly trimmed triangle of pubic hair. Her entire body seemed to blush.

I patted my lap. "Assume the position, as they say in the classics."

She laid herself across my lap, wriggling her crotch on my rock hard erection.

"None of that, young lady!" I said sternly and gave her a light smack with my hand.

That surge again as she squeaked and her bottom rippled.

"You ready for this?"

She nodded. I started spanking her gently and she sighed with pleasure or maybe relief.

Slap! Slap! Slap! I smacked her left then right cheeks alternately, savouring the sensations and sound. She lay passively, just taking it. 'What was the etiquette in spanking your best friend's bottom?' I mused. 'Do you make polite conversation?' Smack! Smack! Smack! 'Is it okay to whack the same cheek twice in a row?' I realised I was in charge. Smack! Whack! I gave her two good ones quickly on her right cheek. She squeaked and shifted a bit. Oh, this was fun. I upped the tempo.

Her ass began to go pink and I could see her pussy peek out from between her legs when she started wriggling her hips as I made the spanks increasingly firm. 

Smack! Smack! Smack! Smack! I began to snap my wrist. She started squeaking and my palm was stinging. 

"Okay, Anita, I think it's time for the main event," I said.

She gave a huge sigh that sounded like regret and wriggled off my lap. I missed her ass already. 

I stood, retrieving the cane. Anita stood staring at me flexing the rod, rubbing her bottom. Her tits bobbed distractingly.

"Okay, bend over the desk." I gave her a gentle nudge in the right direction but she said, "wait," and put a cushion on the edge where her hips were to go, then she stretched herself over it and gripped the far side.

The sight of my oldest friend Anita, bent over her own stark naked, with her panties around her ankles, reddened ass tilted up for the cane was a sight I was unlikely to ever forget. 

"I bet you didn't expect this when you left the house today," she said.

"Life's always an adventure with you, Anita," I said, swishing the cane experimentally.

"Okay," she said, surprisingly businesslike all of a sudden, "When you hit me with that, don't go any higher than here," she indicated a spot a few centimetres below the top of her asscrack. 

"Hold that pose!" I said, grabbing a whiteboard marker from her desk and marking the spot.

"Well that was strangely humiliating," she said.

"I'm about to cane you with this stick," I said.

"Okay in context, I see your point. Also, make sure the point doesn't wrap around my hip, so line the end up about halfway across my right - yes there, and also, try to avoid hitting me below the crease, and the crease itself is called "the sit spot" and is extremely sensitive and I'll feel it every time I sit down for a few days."

"So avoid that too?"

"Do whatever you feel necessary, sir."

"God, this is hot."

"You should feel my ass."

"You should SEE your ass! Okay, young lady, prepare yourself for a few test whacks, then we'll give you your six."

Anita stretched herself back across the desk. She pulled herself a bit further forward so she was up on her toes with her bottom perked invitingly. I laid the cane across the middle of her backside, tapped it a few times, then pulled it back, keeping my eyes glued to the target. She tensed. 

Thwick!

"Ooh!"

I had just flicked my wrist. "Not too hard?"

"You can do better than that!"

"Okay, brace yourself."

Whoosh! Thwack!

"Aah!"

A thin red line appeared this time. 

"More?"

"Yep."

Whoosh! Thwack!

"AAAAH!" 

A white line appeared where I struck her this time, quickly reddening. Anita jumped up, rubbing vigorously, her tits bouncing beguilingly.

"Oh wow, that really stings! Then it stings even more! I didn't expect it to hurt this much! Ow!"

"You still want to do this?"

She grinned, showing all her teeth. "Hell yes, can't chicken out now. Six of those please, sir."

She bent over the desk again. My best friend, a lovely woman I had coffee with, talked politics with, a successful businesswoman, submitting to me, presenting her gorgeous, vulnerable bottom for the cane. I felt that surge of power again and savoured the wildness of the moment. It was so gloriously uncivilised and we both wanted it to happen.

"Are you ready?" My cane tapped her ass.

"Yes, sir. Please cane me now."

Whoosh! Thwack!

She grunted and wriggled wildly, but kept her hands on the end of the desk.

"That's one."

I waited, watching the stripe redden across her backside. When she was still I lined up the next one, a bit lower.

Whoosh! Thwack!

She squeaked and jumped a bit, waving her ass from side to side, giving me a look at her pussy, which glistened suspiciously.

"Two."

Swoosh! Crack!

"AAAAGH!" She jumped to her feet, hands gripping her bottom, and danced around like a lunatic yipping, "Ow, Ow, Ow, Ow, OW!"

I stood back and enjoyed the show. "Three."

She looked at me beseechingly, jumping up and down, hands still gripping her abused buttocks.

"Do you want to stop?"

"God no, I've never felt so alive! Just give me a minute."

As her tits bounced in time to her mad dance I knew exactly what she meant. I could make her jump and scream but she wanted it. This was completely insane but incredibly erotic.

"Okay, get over!"

She bent. I traced my fingers gently across the stripes. Her skin was hot and the stripes were slightly raised. She groaned sensually as I did so and I let my fingers drop to her pussy which was hot and wet. She stiffened. 'Had I crossed a line? We were both married to different people. Was naked caning ok and touching not?' I stepped back.

"Last three. Ready?"

"Yes, sir."

Whoosh! THWACK!

"Eeeek!"

"Four."

Her legs came off the floor then she rubbed furiously, showing me everything. I gave her a minute. Seemed fair.

"Hands out of the way."

Swoosh! CRACK!

"OWOWOWOWOWOWOWOWOW!" Anita literally ran a lap of her office and then jumped and rubbed furiously.

"One to go."

She nodded. The cushion had fallen to the floor but she kicked it out of the way and flattened her tits on the desk, arching her back to present her ass to the cane. 

The stripes on her ass were incongruously neat. I was quite proud of my branding her like this. 

I tapped the cane on her so far untouched sit spot. Her indrawn breathed hissed through her teeth.

Whoosh! THWACK!

Anita shrieked and drummed her feet on the carpet but didn't jump up or rub. It seemed like an invitation so I put down the cane and started rubbing, making soothing noises. As she calmed, I allowed my fingertips to touch the lips of her pussy. She shuddered and stuck out her ass. I took her invitation and stuck three fingers inside her. She groaned loudly and came nearly immediately. I obligingly fucked her pussy with my fingers until she subsided, My other hand gently playing with the stripes I had given her.

I got to my knees and kissed her burning bum all over, making my way to her pussy. She shuddered.

"Fuck me, Dan."

I hesitated. It seemed crazy to draw the line at this point.

"FUCK ME, DAN."

She clearly agreed. I jumped to my feet, unzipped my pants, grabbed her hips and rammed myself into her to the hilt. I slammed into her hard, feeling the heat from her skin. I jackhammered into her. I could feel an orgasm boiling.

Damn it, there was one thing I'd never tried either.

"Anita, I'm going to come on your face." 

I pulled out and she turned and fell to her knees, submissive, face up, ready. I came like a firehose. She quickly squeezed her eyes shut and opened her mouth and I coated her tongue as well. When my balls were empty I guided her mouth onto my cock to suck it clean.

I stood, wobbly-kneed, holding her head, watching my cum drip down her face

"Could you get me a tissue?" She asked and we both laughed, breaking the spell. I wiped her face clean and we lay together on the carpet wondering what to do next.

"Well that was nuts," she said.

"Was it what you expected?"

"Sort of. I'll need to think about it."

"Well, anything for a friend," I said, wondering if we still were.