Smart Assed Masochist

She has a gentle face, when she smiles it dazzles me. But let her dark lashes lower a little, her lips compress into a stern line the sneer makes me want to crawl under her boots and hide.

The look on her face that night all but toasted me. With her hand tightly on my leash barely a foot from my head there was no way for me to crawl away.

“Stupid little man, do you realize how lucky you are that I allow you to worship me?”

Her other hand flew swiftly from one cheek to the other.

“Do you?” another pair of slaps.

I opened my mouth trying to think of what to say.

“Don’t speak, there’s nothing you can say I want to hear” two more slap.

Her voice and the slaps made me flush, even my ears burned. I was just a helpless little puppet.

“You are nothing more than a doormat, a human shoeshine. Yet you dare to maintain the proper respect a slave owes its Owner.” Amazing how she can talk in capital letters.

I should’ve known this would be coming. I’d been a bit SAMish lately. I had a streak of Smart Assed Masochist. Unlike most SAMs I wasn’t trying to provoke her to get more punishment. Trust me, she never made that a desire. I’m a strongly analytical man whose entire approach to life is colored by irony. Her greatest gift to me when she takes control is shutting that down. In serving her and suffering for her my mind quiets, my detachment surrenders to pure feeling.

The irony had broken through a few times recently when serving her. It would just come out involuntarily. Mostly she’d laugh with good grace, though she always made me pay dearly for my flippancy. Either my SAMishness had come to greatly irk her or she was using it as a pretext. I knew she’d tell me later.

“Tonight a slave gets reeducated in his role in life.” Four or was it six more slaps followed in rapid succession. I could feel how brightly I must be blushing. My head felt like a pink balloon ready to pop.

I didn’t notice that my penis had become a pink balloon as well until she locked a cock ring around it. Already cringing from her words I shrunk a little deeper inside myself. Few things are more sensitive than a stiffly erect cock: erection play can be brutal.

“Slide your knees under my chair, you know the position.”

She pulled out a 16” x 16” bit of plywood with a hold in it, my penis went through the hole. Although I couldn’t steel myself for what was about to happen I tried. Equally I tried to beg with my eyes: foolish effort the look would only egg her on.

She placed a boot on my cock and shoved it down and started tapping and pressing on it. Locked into full erection it wasn’t very flexible and hurt very badly. I lay there and whimpered. Slowly very deliberately she pushed down until she pinched my foreskin against the board. Few things hurt worse than that, it was a punishment she used sparingly. It would hurt for days acting almost like a built in chastity collar.

Boot firmly back on top she used it to shove herself up from the chair. I swooned.

“That was the introductory course. Now we get to your real lesson.”

She moved the chair aside.

The sharp point of her boot hit my penis. It probably wasn’t even that hard a blow. But erect, having been crushed it was a tiny point of pure agony. From the corner of my eye I saw the next swing begin.