Pain, Pleasure, and the Unknown Masked Mistress
Dear Mizz Geena,
A year ago, at a BDSM Halloween party, I met a Domme who changed everything I thought I knew about submission. She wore a half-mask that covered her face, dark lipstick, and a leather corset that made it impossible to look away. I was new then, still trying to understand the etiquette of these events, nervous but eager. She noticed me immediately.
She asked if I’d ever played before, and before I could really answer, she had cuffed my wrists. I remember the cool metal, the way she leaned close enough for me to smell her perfume, the command in her voice as she led me to a bench. When she attached me, I realized I couldn’t move. Panic hit for a second, but she reached over and slid her fingers into my mouth, telling me to relax. I was drooling and shaking, lost between fear and desire.
Then the tone shifted. She pulled her panties down and stuffed them into my mouth to silence me. The first crack of the cane tore through my mind. The pain was sharp, relentless. The crowd started to gather, watching, laughing, cheering her on. I wanted to scream stop, but at the same time, I didn’t want it to end. I was hard as a fucking rock, my body betraying every ounce of pride I had left.
And then she pegged me. It was only my second time ever, but nothing like the first. She made a show of it, lubing me up, looking right into the crowd as she fucked me. Hard. Rough. Fast. She made me take it all, and the crowd watched as I broke down. By the end, I was trembling, soaked in sweat and cum, completely gone. I had come several times, unable to stop myself.
When she finished, she leaned down, whispered something in my ear I still can’t forget—“Good toy”—then she was gone.
Last week, almost a year later, I got a message from an unknown number. Just three words: “Ready for round two?”
I don’t know who she is. I’ve thought about her every day since that night. Part of me wants to surrender again, no questions asked. But another part of me wonders if I should demand to know her identity first.
Mizz Geena, should I give in to the mystery, or insist on unmasking the woman who ruined me so perfectly?
—The boy on the bench
Dear boy on the bench.
You’ve given me a lot to think about, and I’m sure many readers will feel the same mix of arousal and unease. Parts of your story are concerning. You were new, inexperienced, and there was no clear conversation about consent or limits before things began. That is never ideal, even when the experience turns out to be thrilling.
Still, you didn’t describe saying no or using a safeword, and from what you wrote, you were deeply aroused and satisfied by what happened. The scene was rough, raw, and unplanned, but it also clearly awakened something inside you. Those moments where control slips away are often where true submission begins. She got what she wanted, and you discovered a new level of surrender. That is why it was hot. You were ruined so perfectly because you let it happen.
As for your mystery Domme, you absolutely have the right to ask questions or set boundaries. You might even text her a few points in advance, just to establish some limits or a hard stop if needed. That doesn’t make you less submissive, it makes you a responsible one. However, understand that unmasking her might ruin part of what is turning you on in the first place. The anonymity, the danger, and the uncertainty all feed the fantasy.
In the spirit of Kinktober, I say lean into the mystery, but do it with care. Have a safety net in place, perhaps a friend who knows where you are and can check in or step in if needed. That way you can surrender without losing your footing.
Enjoy your kinky self, Haunted Sub. And yes, report back on November 1st. I want to know how round two unfolds.
—Mizz Geena
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