For the briefest of moments, I freely admit I was quite uneasy.
I had never before experienced corporal punishment of that sort, at least not since the occasional spanking I'd received as a child. And while I had so enjoyed the videos in which Miss Vera had punished countless other men and women, never had it crossed my mind that the day would come in which I would find myself in the same precarious position.
But that day had come, and there was nothing I could do about it.
With my eyes facing the wall, it was impossible for Miss Vera to see the fear that was quickly filling them, but my body language more than made up for that. I was practically shivering on principle alone, although, strangely enough, my cock had not shrunk back in the slightest since she had pulled out the crop.
That alone was all Miss Vera needed to see to know that, afraid or not, a part of me was quite intrigued...
And that was the part she intended to play with. The very same part which had gotten me into this situation in the first place.
"While you've been a good boy, Edward, I must confess that, knowing how long you gooned over my content for free all those years... You understand you need to be punished, don't you? It's really the only way I can be certain you will never be that naughty again."
Once upon a time, I may have disagreed, but now... She was right. I had been so bad, so naughty, and though I'd spent a fair amount of money on her in my quest to repay that debt, it was not enough. There were certain things even money could not pay for, but that didn't mean there weren't other ways for me to do so.
Before I could fully process her words, however, I felt the sting of the crop against my bare ass cheek. The leather tip cracked, and, had I not been restrained as I was, I likely would have jumped into the air from the sensation. Alas, such movement, just like any pleasure I could possibly derive from the surrounding leather as well as the gorgeous Goddess who owned them was denied to me.
Besides, now was not the time for pleasure. Now was the time for punishment.
"As this is your first time, Edward, I won't besmirch you for failing to properly express yourself. However, you should always thank you Goddess for anything and everything she does to you. Is that understood?"
Another strike, this time on the other cheek, and though it hurt quite a bit, I knew what she was getting at. Even with the gag firmly in my mouth, I replied as best I could with a muffled "Thank you, Miss Vera."
From behind me, she giggled. "Good boy."
The pain from the crop was replaced momentarily by the familiar sensation of Miss Vera's soft, leather-clad palm as she gently rubbed my cheeks, and I moaned through the gag. It felt so good, but such joy was taken away just as quickly as it had been offered.
Again, the crop struck my tender flesh, and this time Miss Vera didn't stop at a single hit. Four strikes on each cheek, and with each one, another muffled offer of thanks. And after every one of those, the briefest touch of her gloved hands. It was lovely, yet fleeting, and I wanted nothing more than to feel it again. No matter what.
Not content to simply redden my behind one strike at a time, Miss Vera's crop moved up and began to leave a number of marks across my bare back. I could feel tears forming, but again, offered my thanks. She was certainly right about my needing to be hydrated for this lesson.
She gently ran her fingers along my back, the cool leather mixing with the harsh stings, and all the while, my aching cock continued to leak. A small puddle of precum was beginning to form on the marble floor beneath me, and it honestly baffled me.
Much as I had enjoyed watching such things happen to others, I didn't think I would grow so aroused being in the same position. Yet there was something about being there, surrounded by Miss Vera's leather, feeling her touch, knowing that she was doing what was needed... My mind could barely conceive of all of this, it struggled to make sense of things... With every strike, every thanks, every touch, and every repetition of this cycle, I was beginning to equate them together.
The pain of the crop, the pleasure of her leather gloves... The sound of her giggles whenever I struggled to thank her through the gag or struggled against the restraints, they were one and the same. A wondrous cocktail, one which reminded me again and again and again that her pleasure, especially when it was derived from my submission, was all that mattered.
Knowing just how much Miss Vera enjoyed what she was doing to me made me enjoy it, and I knew right then that no amount of pictures or videos could ever truly compare to the real thing. To truly serving her.
After a few more strikes, Miss Vera stopped her assault, but if I thought for a second she was finished with my lesson I was quite mistaken. The sound of her heels tapping against the floor filled the air, and Miss Vera was soon standing beside me. She could see the tracks of my tears streaming down my face, but more than that, she could see the puddle on the floor.
"Hmm, I think you might be enjoying this a bit too much Edward. Such a naughty little boy, dribbling precum when you should be taking your licks... Perhaps a stronger lesson might be required."
The tip of her crop gently tapped my cock, and it squirmed from the new sensation but still did not shrink. Miss Vera ran it along the length of my erection, tracing lines up, down and around, and even poking at my full balls. I moaned, and almost instinctively replied with a muffled "Yes Miss Vera."
So lost in the mix of everything, I had no idea what I'd just agreed to, not until she put the crop back on the shelf and picked up a large leather paddle. "Yes, this should do nicely. Now, be a good boy Edward, and count for me. You can do that, can't you sweetie?"