Lots of action, lots to tell, so let's get to it.
Where I left things off, I'd just been mercilessly teased on the Venus for hour(s?). The next day, I discovered I was a bit chafed "down there," like I hadn't been since I was a teenager. Overuse, and all. The head was a bit tender to the touch, but I had a full-blown session to take part in the next day, so I soldiered on.
At last, my Keyholder came over later in the day. It was very good to see her, as it always is. We relaxed in each other's company, caught up, etc. But eventually, she set into motion the plans she had.
The first item on the agenda was my punishment. I'd been racking up cane strokes left and right over the past week, mostly for "whining" or being somewhat bratty. Annoying, in any case; earlier, my Keyholder would tell me "that's 5 more" after such incidents. Well, I'd gathered 40 of them by the time Monday rolled around. She had me get the large rattan cane, and the smaller, whippier plastic (rubber?) one. She put me up against the wall, in position, hands on the wall, ass sticking out, and began. These were punishment strokes, and she did not go easy. To say that it hurt would be an understatement. I was soon sweating the fear out of my body, and mustering all self control I had to stay in position and not blubber. I must have whined again, for she added five. It was the worst (best?) caning I'd had in a long time. By 10, I was gritting my teeth. By 20, I was howling. She switched to the plastic cane, which stings much more, but does not thud like the rattan one. It took forever, and no time. All I remember is that at 45, I was a blubbering mess, kneeling on the floor, bathing her feet with my tears. I thanked her for my correction, and kissed her feet. [Ed. My whining has markedly decreased]. I went and showered, readying myself for round two.
Then, she had me ready the Venus-2000. I was very deep in subspace by now, and completely pliant. She placed me on my knees, sitting on my shins/feet, with a yoke on (a tight metal contraption that holds the neck and wrists together in front of you). My ass stung and pulsed from the caning. She bound what needed to be bound to get me helpless, and set to work on the Venus. After some fiddling with it, it clamped on to my penis, and began pumping rhythmically, relentlessly, mercilessly.
It was tough. It was a hard position to hold for a length of time. A disclaimer: I was so deep in subspace that I don't know if this took 5 minutes or 50 minutes. In any case, the position of sitting on my legs got more and more difficult to hold. There were a dozen little pains that took my attention away from the pleasure that the machine was delivering. A rope biting here, the hard, unforgiving clamp of the metal yoke, a cramp in my foot, my tenderized ass rubbing against me. It was more torture than pleasure. I didn't know what my Keyholder had in mind, and I was too zonked out in subspace to know or ask. I felt like I wasn't giving her what she wanted, which (I thought) was me moaning in pleasure on the edge of coming instead of moaning in pain at the difficulty of holding the position for such an extended time. In any case, she eventually let me down, and had me crawl into bed, where I pleasured her at her whim. I ended up not coming (of course), exhausted and asleep in her arms. Not a bad place to be.
The next day, we took it easy. My ass still hurt, the fires stoked by a maintenance caning, and another few strokes of punishment for mild impertinence. We had a wonderful time, doing boyfriend/girlfriend stuff, no one suspecting that this lovely woman with me had reddened my buns so.
p.s.
We've put the contract on an informal hold, for now, for those that have been wondering...
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