The request came through late one evening and I remember blinking at my phone, thinking—really? He told me upfront that he had just ended a DDLG relationship and wasn’t ready for anything serious, but still wanted… well, a shadow of it, I suppose. I didn’t know what to make of it, but I said yes. I usually do.
He insisted we meet in a café first, neutral ground. That already told me he wasn’t reckless. I asked about dress—normally I turn up quite polished, heels, all that—but for him? He just wrote back, “Cute. Comfortable.” Oddly specific, yet simple. It reminded me a little of when Kate set the stage for Duo dominatrix session, how the tiniest details of dress and attitude ended up shaping the whole atmosphere.
I was braced for the worst, if I’m honest. But when I walked in and spotted him, over fifty, silver hair, fit in that quietly disciplined way—it was a relief. More than that, it was… pleasant. He hugged me quickly, nothing invasive, and I felt my shoulders drop.
“You look even better in person,” he said, a wink that should have been cheesy but somehow wasn’t.
I laughed, awkwardly, and sat down. He laid out his conditions—roleplay, boundaries, how he wasn’t looking for another sugar-baby situation. I almost asked why not, but the way he avoided certain words told me enough. Some things are better left untouched.
The talk drifted to safer ground. His business. His hobbies. He lit up about his work in a way I didn’t expect, and I found myself leaning in. Passion does that—it draws you closer, even if you don’t mean it to. It had the same effect as that night of soft candlelight and high heels in Liverpool Street, when conversation alone felt charged with something more.
By the time the coffee cooled, we had settled on a hotel meet. My rule, not his, but he agreed without hesitation.
Second meeting. I knocked. The door swung open instantly, as though he had been waiting right there. Another hug—this one warmer. I caught myself smiling more than I meant to.
He took my coat like a gentleman and asked if I wanted room service. I waved him off. I didn’t need a sandwich; I needed to know how far I could trust this man.
Then the moment tilted. Bedroom. A brush of hair off my face. That slow lean in, like he was testing whether I’d let him. I did. His lips were careful, skilled even, and my hands betrayed me by clutching his shirt. For a second, I forgot this was supposed to be roleplay.
“What does my baby girl want?” he whispered.
I swallowed, played along. “You.”
He laughed quietly, scooped me up, and the rest… well, let’s just say the lines between fantasy and reality blurred more than I expected. That blur reminded me of the time I picked up the phone on a whim and ended up slipping into someone’s secret world—an escort answering the call, caught between duty and desire.
When I left, another date was already pencilled in. And walking back down the hotel corridor, shoes in hand, I had to admit to myself—I could get used to this arrangement.
If the psychology of power and surrender catches your curiosity, you might also enjoy exploring The unapologetic guide to humiliation kink.