A Fun Five Hundred


Not all of my sessions are structured towards punishment. Not everyone wants to be scolded. Some people visit me purely to experience the cathartic nature of CP with someone who truly enjoys administering it. Dean is one of these people.

On a Saturday afternoon in mid-September, I find myself in a wonderfully sadistic mood whilst preparing for Dean’s arrival. He has been reporting to me each week via email with updates on his personal targets and has truly excelled himself. The targets were set earlier in the year and Corporal Punishment is offered to him as a reward for achieving his goals.

Dean’s goals have been immensely challenging for him and he relishes in this. As my eyes drifted slowly over my vast collection of punishing implements, a plan began forming in my mind.

‘He needs to be challenged’, I thought.

Methodically and deliberately, I set about selecting twenty pieces from my collection to display on the chair in the playroom. My choices were well considered and with each one I became more excited for the session ahead. 

  • Thick based, heavy wooden spoon.
  • Long handled, flat based wooden spoon.
  • Dense ebony hairbrush with concave bottom.
  • Lightweight, oval wooden bath brush.
  • Flat round bath brush with heavy head.
  • Lollypop shaped dark wooden paddle.
  • Thick, heavy cheeseboard style paddle.
  • Long handled, flat spoon shaped paddle.
  • Thin, stingy teak paddle with varnished finish.
  • Slim, holed dark wooden paddle.
  • Varnished, lightweight paddle with holes.
  • Ruler shaped wooden paddle with metal studs.
  • Quarter inch, silicone bat shaped paddle.
  • Heavy rubber soled gent’s plimsoll.
  • ‘Hand of God’ – holed, broad leather paddle.
  • Metre long, heavy leather tawse.
  • Straight dragon cane – junior with leather handle.
  • Straight dragon cane – senior with leather handle.
  • Crooked handled senior dragon cane.
  • Sinister black whangee cane.

A deliciously devious and varied selection for an experienced bottom.

The implements were laid out in all their glory and, after a brief catch up over hot tea, Dean was invited to join me in my playroom where his fate had already been sealed. No sooner had I opened the playroom door than I heard a gasp escape Dean’s lips. He had spotted the overwhelming array instantly and turned to me with a glimmer of real fear in his eyes. How splendid.

I closed the door behind me and made my way over to the couch in silence. Dean’s eyes flicked back and forth from me to the chair, searching for answers. There were none to be found. Yet. I fired an evil grin I his direction, enjoying every moment of his confusion and terror. Eventually, when I was ready, I began explaining my intentions to him.

Five hundred strokes, twenty implements and three choices to be made.


Choice 1 – Decide if you would rather take 25 strokes from each implement here, or 20 from each plus an additional 20 from my hand as a brief warm up.


Choice 2 – Carefully look through the implements and decide if any of them are ‘hard limits’.


Choice 3 – You are permitted to make one implement swap for another piece in my collection.


A lot to think about. Dean mused slowly and I could tell he was struggling to come to terms with what he was presented with. After a short stutter, he began to reveal his choices. He wanted to forego a warm up with my hand. He advised that none of the implements were outside of his limits and, on that basis, he chose not to swap any of them. Very wise decisions indeed, and ones that pleased me. I had time to play with and I intended very much to ‘play’. I talked through some of the implements with Dean, prolonging his anticipation. Experienced or not, he knew this was going to hurt. He also knew that I would enjoy every moment of it.

I chose the thick wooden spoon to begin and had been striding around the room for some time with it in my hand. Ever ready to strike. Dean knew it could come at any moment. Was he prepared? Once we began, he knew it wouldn’t stop until the chair was clear of all implements.

I picked the precise moment to begin. By this point Dean was nervously giggling at his imminent demise. He wondered if he could cope. I’ve no doubt he had received more than 500 strokes in previous sessions but having it all laid out in front of him made the challenge devastatingly real.




As if out of nowhere Dean’s left buttock absorbed the first strike. The nervous laughter stopped suddenly as his body processed the shock of the impact. A neat oval shaped redness formed quickly. It was time for business.

Another equally intense thwack met with his right buttock. Another deep exhale.

Only two strokes in and Dean knew already that this session would be a testing one.

Varying in intensity and speed, the twenty-five strokes made their way onto Dean’s bottom one by one, slowly decorating the blank canvas with vivid hues of pink and red.

After I was finished with each implement, I told Dean, I would place them along the wall next to him. We could both see what had gone before and, therefore, what was left to come. The visual impact of the implements was proving to be difficult for Dean. As he often does, he chuckled at the ridiculousness of his situation. I met him with an evil chuckle of my own, before moving toward the chair to select my next implement.

The ritualistic nature of the selection process was beautifully powerful. I took my time deliberating over the collection before me and could hear Dean’s heavy breathing behind me as he watched the process out of the corner of his eye. With each piece, I saw an opportunity. I wanted to paint with varied and exciting brush strokes across his bottom. Rather than merely start with the lowest in intensity and work our way through, I interspersed more severe implements with those easier to handle. An irregularity to my selections fuelled Dean’s fear throughout the scene. He couldn’t predict what was coming. I made sure of it.


After the first fifty strokes, I let him stand up to stretch and drink a little. I laughed when I pointed out we were only 10% of the way through. Remorseful acceptance.

Back over the bench and I continued with my masterpiece. Flashes of purple and hot white crept through from behind the crimson surface.

Quick fire sections at lighter intensity to maximise the sting were followed with rhythmically slow, hard, deep thuds.

We took another break at the half way point and Dean sat for the first time on his already sore bottom. A breath-taking silence passed between us as I watched Dean’s eyes move from the implements against the wall – the ones he was now safe from – to the ones still adorning the chair – the ones he has yet to face.

Time passes. Intensity grows. Soreness fades. Anticipation rises.

He’s bent over the pommel horse before he has a chance to plead for any mercy. We have some serious pieces left and it’s only going to get worse from here.

Dean is made to count some of the sets, while he is still able.





Stroke after stroke. A crescendo of pain. Absurdity causing giggles. Both of us enjoying the moment together.

He’d been caned. He’d been paddled. He’d been strapped. He’d been tawsed.

It was time for the final pieces – a thick rubber paddle and the ‘Hand of God’.

So far away from that break after the first 10%. We now only had that far left to go. He was exhausted but ready to finish it. These fifty strokes from both implements were mixed together. The heavy thud of the rubber paddle packed a punch while the ‘Hand of God’ attacked his upper thighs relentlessly.


As the five hundredth stroke loomed, I glanced at Dean’s face. He eyes showed promise of glazing over though I knew instantly he wasn’t quite there. It fell and we both knew we needed just that little bit more.

Aiming at his upper thighs, I proceeded to beat the ‘Hand of God’ across them at a quickening speed. He watched my fury through the mirror in front of him – a mix of pain and pleasure on his face.

Sharp, sudden strokes slamming against him. Whack after whack. Pain reigning down. Speed hastening. The fire grew. Until…




The last stroke fell across his badly bruised legs and bottom. We were both spent.

My breathing was as heavy as his and, for a moment, we allowed the sound of it to occupy the room fully. I casually tossed the leather paddle aside and slumped into the settee behind Dean. After a short time, our eyes met through the mirror and a smile crept across both of our faces. It erupted into laughter and the intense weight of the atmosphere created in session lifted.

Slowly, Dean pulled himself off the pommel horse and we shared an embrace. As usual, we headed back down to safety and comfort for a cheery conversation.





Dean took on the Fun Five Hundred Challenge and excelled himself. Do you think you could handle the same?




These sessions are tailored to the individuals I am playing with.  No session will be repeated like for like and, indeed, cannot be due to the nature of the relationships I have with the persons in question.


Names have been changed to protect identity. Consent has been granted for photographs and blog entries to be published.

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