He was a man who liked routine, so his punishment scenarios rarely changed. She'd kneel at the bottom edge of the bed, face down in a pillow, ass in the air, legs spread wide. It was humbling, this holes-exposed-for-punishment position, and just being in it could cause her tears to flow. He didn't mind tears, or crying, or begging -- expected them, in fact --as long as she understood that they had no effect on the severity or duration of her ordeal.
It always started with a beating of her asshole with a narrow but heavy strap he'd had made specifically for this task, by a leather crafter at a street fair. His aim was precise and no amount of dodging on her part prevented the wicked end of the heavy leather from snapping directly onto her exposed hole. She knew that as long as her buttocks were moving (and it was only her buttocks because she knew better than to move out of position), her strapping wouldn't officially begin. But she couldn't help it. Her ass would desperately weave up and down, side to side until, exhausted by the futile effort, she was finally still. Then came the official start of her punishment, the rapid and steady strokes of the strap directly on her asshole. Ten, twenty, thirty, forty, fifty. After every twenty strokes or so, he would stop to prove the hole, causing her to squeal and buck under his hand. The strapping stopped only when he felt her asshole swell to a tight plumpness, and he could tell by the way she flinched at the lightest touch, that it was time for Step Two.
He used what she thought of as the building block technique of punishment, with each step contributing to the pain factor of subsequent steps. The purpose of the asshole strapping was not only for punishment in and of itself, but to set the groundwork for a more painful ass-fucking to come.
The size of the putt plug used in Step Two depended on the severity of her crime, but even the smallest of his collection was too much for her tightly closed rectum. There had been no training of her asshole to widen it to accommodate whatever she would be required to take, as she had often read about in stories. Her asshole was never used except for punishment. He wanted her as tightly closed as possible, so that the maximum pain was caused by each invasion she was required to endure. This was his sacrifice, that he didn't use her asshole regularly, as he would have liked. She was, generally, an obedient girl and this, one of the harshest of the punishment scenarios came into play only once or twice each year. But those months of sacrifice was worth those few moments when, howling and shaking uncontrollably beneath him, her asshole sucked his cock into a vice so tight that he though his entire body would explode from its orgasmic power.
But we digress....
The most painful insertion decreed a dry plug, but experience had taught him that a dry plug was almost impossible to insert. And while the aggressive pushing elicited more than the requisite cries of pain, he really didn't have all day to seat one butt plug. So before the plug went in, he would take a small amount of pepper oil on a gloved finer. She would cry out as the finger worked lightly over her bruised anus, then again as the finger pushes open her sphincter to coat the area just inside her hole. Her relief at the finger's exit lasts only as long as it takes for the oil to begin its burn. The pepper oil is a satisfying compromise -- the small amount of oil easing the plug past the sphincter while creating a burn on asshole. And if the plug carries with it the residue of the oil down the deep, dark path of her rectum, all the better.
He pushes the putt plug against her bruised and burning hole as she screams her distress into her pillow. Its a credit to his training that she would never think of moving away but remains, ass offered upward, to allow for the torture of her already tortured hole. Her swollen sphincter doesn't part easily, even coated with oil, and a long few minutes of pushing and twisting is necessary before her asshole opens. This is her begging time, as the plug makes it's slow decent into the depths of her bowels. Please, I'll be good. Please. Oh god it hurts...hurts so much. Please. Please. I'm sorry. I'll be good, I promise. I'll be good.
As the widest part of the plug reaches her sphincter, he stops to allow her to feel the full impact of the stretching of her hole. He waits until her crying has stopped, then waits another minute for her to quietly accept this modification of her body. Then, recognizing the slight body shift that signals her acquiescence, he pushes the plug all the way.