His cup runneth over

It's been more than three months since the boy stopped coming wherever he so pleased and into a cup. He understands his punishment and while he might not like it, he is always eager to fulfill it.
Not the boy's cup but very similar

I can tell that he does not enjoy it or even look forward to it. Yet he does it anyway. Because he knows this is something that I not only want but command. I am pleased with his progress and the more his cup fills the less I feel angry about his transgressions.

My goal was never to completely fill the cup (though that was always an option) it was simply to remind him that his body as long as he submits to me is mine to use however I see fit.

And now, here he is looming on the 25th and final time he will fill the cup. I leave it up to you dear readers.

How should he finish his punishment? Please vote on the right hand side by May 5th.
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"Whipped" into shape

In the dark, cool basement of the party I listened to the moans and screams of pain and pleasure around me. As my Mistress tied me up in front of the St. Andrews Cross, I could hear the slapping of leather against flesh behind me. To my right, I spotted a woman’s rear turning a shade of crimson as she was spanked repeatedly. 

Once my Mistress finished tying me up, I leaned back against the cross. She must have been able to sense my distraction, as she informed me to shut my eyes. 

 I foolishly asked why she wanted me to do that. My Mistress immediately responded with “Because I said so!" 

As I closed my eyes, I felt her hands run across my chest. The screams and moans of the others continued to echo, acting as a soundtrack to our scene. I felt her tongue brush my nipples before she clamped them. 

There was a brief moment of pause before she became verbal. “You haven’t been following the rules," she yelled at me. 

I must have responded with an air of confusion, because she immediately whipped me. “ Repeat them to me," she demanded.

As I recited each rule, she whipped me repeatedly. 

After reciting all five of them, she replied “You haven’t been calling me by the proper name. You haven’t been calling me anything at all. Did you think I wouldn’t notice?”

As if she knew the answer to that already, she punished me with a stinging whip across my nipples. I yelled out in pain. My scream went unnoticed amidst the gaggle of pain-filled outbursts flooding the room. I later found out this is when others started to watch our scene.

“Are you going to follow the rules?” She whipped me once more. 

“Yes” I replied. She whipped me again. 

“Yes what?” She said. 

“Yes Mistress” I responded with a trembling voice. 

She then started whipping me frantically across my chest, legs, and midsection. My body began trembling uncontrollably and whimpers escaped my mouth. My nipples were in an immense amount of pain. I believe she was aware of this, but she didn’t seem to care and may have even laughed but I can't be sure. I could feel tears forming in my eyes. My screams of pain again meshed with the others.  She whipped me for what felt like an eternity. Finally, she let up. I was left gasping for breath before I collapsed in a pile on the floor...

Edited for approval by: Natali Noir
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