Angela’s Story: Nan bets a hundred


Angela’s Story begins here.

I once heard a story about a man who put his head in a lion’s mouth. On being asked why he had done it he replied, “it seemed like a good idea at the time.”

Now maybe it is just me, but I always thought all these glib reasons for doing the most incredibly stupid things was just in stories. Then I went to a party with David, Nan and Alex and things got a little interesting.

We were talking about life, the universe and everything, when Nan asked, “why is it always six of the best?”

David spluttered on his drink and Alex laughed.

I was blushing in case someone had overheard. It would have been a great topic of conversation over dinner between the four of us, but in the middle of a vanilla party, it was a bit rich.

Oh vanilla is my new word. I was at a student party to mark the end of my second year at college and the subject turned to BDSM. It must be a new fashion. Apparently vanilla is out and alternative sex is the new black.

“No seriously, why is it six? Why not eight or 10 or five or…” Nan did a flip with her eyes and looked skyward for inspiration. I guessed she had been drinking too much again. Alex certainly thought so from the way he was glaring at her.

“I think it is because traditionally it was thought that six of the best with a serious cane was the most anybody could reasonably stand,” David suggested helpfully somewhat amused.

“But Alex has given me much more than six before and I know you have really handed out a dose to Angela now and again,” Nan scoffed taking another sip of her drink.

“Shush,” I hissed looking around mortified.

“But seriously though,” Nan pressed on regardless.

“Well obviously there are exceptions for particularly naughty bottoms,” Alex said archly relieving Nan of her drink.

I had to laugh because he sniffed it for evidence of goodness knows what.

“I must have taken two, three or even four dozen before now,” Nan bragged. “I mean it hurt, but it wasn’t exactly the end of the world.”

I remembered a couple if three-dozen sessions and baulked, it might not have been the end of the world, but it had been close to being the end of my end, I thought.

“Funny, I don’t remember you being quite so stoical at the time,” Alex said with a hint of irritation.

“But you do know what I mean,” Nan said dismissively.

“No, not really,” David chuckled, “why don’t you enlighten us.”

“I bet if I had to I could take a hundred strokes with a cane,” Nan said a little too loudly for my liking.

“I bet you couldn’t,” Alex was agog and sniffed her drink again adding as an aside, “what is she on?”

“I bet I could. I bet you £100 that I could.”

I gaped and saw David and Alex exchange looks.

“So you are saying that you could take 100 cane strokes on your bare bottom?” Alex said thoughtfully, adding, “what with no special conditions?”

“Yep,” Nan said triumphantly, giving me a conspiratorial look. “No special conditions.”

I wondered if she had some angle or some clever ruse to throw at us as punch line. Personally I would pay £100 not to have my bottom caned.

“You’re on,” Alex said holding out his hand to shake.

Nan took it and pumped it once decisively.

“David, I suggest we convene at our place tomorrow night and as the expert, you do the honours with a cane of your choice,” Alex said with a shrug.

“Hold on, I…” Nan spluttered.

My jaw dropped as I realised that she had just be mouthing off and not thinking it through as usual.


The following evening David was in an odd mood and I watched as he laid out his many canes to peruse.

“This thin one would really hurt,” I said picking up one that I had never felt. “But it wouldn’t do much damage, even after a hundred strokes.”

I was excited about what was to come, but also a little scared. Nan, either through design, or drunken folly was raising the bar for both of us. If she took all 100 strokes then at some point, somehow I know that my bottom would get a taste of the honours.

“Yes, and more, she would be very sorry after a dozen but it would too easily prove her point. I really think she needs a lesson, besides I owe it to Alex to have her beg off.”

“But what if she doesn’t,” I asked in dismay.

“Will you kindly allow me to handle this,” David snapped.

I knew when to keep quiet.

We arrived at Alex and Nan’s about an hour later. I still didn’t know what David had in mind, as he had taken about a dozen canes in a long holdall. Poor Nan must have been terrified, I thought as Alex ushered us in.

Nan was waiting in the main room dressed only in a hooded zip-fronted sports top, the kind made from sweat top material. She was wearing the hood up, which served to emphasise her naked legs and firm defiant bottom.

Alex had placed Nan with her arms behind her back facing the wall. I thought it a bit mean as this was supposed to be a contest not punishment, but it was Alex’s house so it was his rules. I was certain David would have done the same in his position.

It was a few minutes before David was ready and then Alex had Nan turn around.

She tugged the front of her sweat top down to cover her sex and I blushed for her. This also made the hood close around her face, so that all I could see was her obstinate pout.

Then I saw that David was holding the largest and heaviest of his canes, the one he referred to as his borstal cane. I had only felt it once or twice and that had been for six on each occasion. I nearly protested, Nan wouldn’t sit down for a year.

Nan looked up at David’s weapon of choice and her eyes went wide. The insolent pout was replaced with a perfect O.

“Bend over the back of the armchair dear,” Alex instructed. “Keep your legs straight and your bottom up looking pretty for David.”

I expected Nan to surrender at this point, although I would have been disappointed. Thankfully, and I mean that if I am honest, she took one reluctant step forward and then she obeyed. Her gorgeous bottom was thrust up and back a little to perfection and I went a little tight down below and not a little moist.

Then once Nan’s eyes were firmly fixed on a single point on the opposite wall as she had been trained to do, Alex produced a standard cane from behind his back and David and he swapped sticks.

I must admit I grinned at this, both in relief and amusement at the ruse.

“Now my love, are you sure you want to go through with this?” Alex asked. “I could make it six of the best for wasting our time and then we could just have a drink.”

“Just get on with it,” Nan said grumpily.

“Alright then. We will begin with a dozen. You will take them all with the minimum of fuss. Then I will ask you if you want to continue, do you follow me?”

“Yes I get it,” Nan said sullenly.

“Then David will give you a baker’s dozen and so on, alternating between 12 and 13 strokes until you want to give up. For the last 13, you will be allowed to stop proceedings at any time.”

“Alright, I agree,” Nan muttered.

“I wasn’t asking,” Alex said sternly. “David, over to you.”

David had taken his sweater off and was busy cutting the air with practice strokes by this time. Each cut made me jump and tingle all over, heaven knows what Nan was thinking.

All eyes were on her firm white bottom as David lined up for the first stroke.

“Ready?” David asked.

“Get on with it, will you,” Nan said impatiently.

“Manners,” Alex snapped. “You don’t want a spanking in front of our friends before we even begin do you?”

“Sorry,” Nan said meekly.

Then Alex nodded to David and then he stood back.

David tapped Nan across the bottom with the cane a few times and I heard a sharp intake of breath. I knew how she felt.

The first stroke came suddenly. The swoosh-crack of it made me jump, but I barely saw it. Then only evidence was the white-on-white line across Nan’s neat buttocks.

I usually can’t keep quiet for the cane but there was barely a gasp from Nan.

We all waited as the line swelled a little and turned rose pink.

No one spoke and I surreptitiously rubbed my thighs in my excitement.

Then David caned in again hard.

Nan gave a little hint of a groan and I saw the top of her head bob up and down for a few beats.

Again we waited for the stroke to develop alongside its sister.

Two strokes and only 98 to go I thought as I licked my lips. This was a rare treat to be this close to the real deal without being next in line. I relished the novelty.

David kept to the same pace for the next 10 minutes. It must have seemed longer to Nan. Usually that would have been enough to have her climbing the walls and crying for mummy, but I suppose with the right mind-set and the knowledge you have a long way to go, a girl can hold the pace, for a while anyway.

“That’s 12,” Alex said at last. “Shall we stop?”

“No,” Nan said huskily. Her voice was on the verge of tears. I could almost hear her eyes watering from where I stood.

“Very well,” Alex said.

For the next 13 David took on a very determined demeanour and seemed to lean into each stroke. These he lay on faster and after only four minutes the second set was over.

By now, with 25 clear rides on her bottom, there was little enough virgin flesh left for further chastisement and I felt certain that Nan would surrender.

“Enough?” Alex asked. There was a concerned edge to his voice now.

Nan shook her head slowly and deliberately. Then there was the smallest of whimpers.

David and Alex exchanged glances and David looked at me. I was open mouthed in awe and excitement, but I didn’t dare speak. Then Alex shrugged.


“Uh,” Nan groaned at the 31st stroke.

After that, her by now audible breathing became ragged and she groaned out loud at every stroke.

The third set had been given almost as slowly as the first dozen and I was beginning to realise that a caning that was only a third of the way through after nearly half an hour added up to one epically seared rear.

It was only after David finally stopped the caning that I realised that Nan was gently crying.

“Shall we end it then?” Alex asked.

He had a bitter look on his face and I felt guilty for enjoying Nan’s caning quite so much.

“Nan?” Alex pressed. “I think the point has been made, don’t you? Give it up now.”

There was an almost tangible tingle in the air and I held my breath.

Nan was breathing heavily through her nose and her head rose and fell with the effort.

“Nan shall we stop?” David asked.

Nan shook her head. It was almost in perceptible, but it was clear. I had been transfixed by the scene so long that I realised I was dribbling. I blushed at this and hastily wiped my mouth.

Nan’s bottom was heavily scored and where the strokes had started to merge had taken on a glassy ruby appearance. I wondered if David might give up. He certainly looked reluctant to begin over and seemed to weigh up the situation along with the cane in his hand.

Then David walked over to his bag and picked up a new cane. The thin one I had seen earlier.

I held my breath as David lined up for the stroke. Then it came.

Nan’s shriek took me by surprise. Alex frowned and kissed the air like David did whenever West Ham had a near miss with a shot on goal.

Nan’s reaction was to set the tone for the rest of the fourth set of strokes and by the end she was in bits and started wailing something incoherently into the carpet behind the armchair.

“I think we really are done now aren’t we?” Alex said, sounding relieved.

“Fuck you,” Nan spat.

“I won’t have this,” Alex said angrily. “If you going to be like that then we really have gone too far.”

“Sorry,” Nan said in a small voice. “But I can go on. Really I can.”

“Alright then,” David agreed, “But we’ll take a break, so into the corner with you.”

“I’d rather go on,” Nan said sounding more like her usual self.

“I really don’t care what you’d rather,” David said, but he had a twinkle in his eye.

To be continued.

3 Responses to “Angela’s Story: Nan bets a hundred”

  1. 1 Karl Friedrich Gauss

    My vote for a surprise ending: Angela’s going to volunteer to take the remaining strokes for her dear friend.

  2. 2 paul1510

    DJ this is cruel, when do we see the finale.

  3. 3 anushree

    you know what I am going to say. So, thanks.

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