“I’m not very good at talking to women,” he admitted quietly, almost apologising with the words.
“That’s no problem at all. I’m easy going,” I told him, smiling in a way I hoped felt warm rather than professional.
He was new. The Escort agency in London had passed him to me because, apparently, I was the most approachable of the London escorts. I wasn’t sure whether that was meant as flattery or something else, but I went along with it.
He asked for a role-play. Nothing outrageous — just the pretence of two strangers flirting before heading up to his Mayfair hotel room. The request surprised me. For someone who claimed to be shy, it was rather bold. When I pressed gently, he explained in halting tones that he had little experience with women, or people at all. The confession hung in the air, so vulnerable I could only nod.
I chose my outfit carefully: a red dress that clung to my waist, heels that made me walk with a slower rhythm, and jewellery that glittered just enough to say I had tried. My hair pinned up, lips painted, a little armour of confidence. We’d agreed he would wear an iris flower in his buttonhole — an old-fashioned signal, a secret shared only between us.
The hotel lobby was humming quietly when I arrived. I scanned the room, half-nervous, half-curious, and then I saw him. There it was, the iris. What caught me off guard was not the flower, but him. I’d expected awkwardness to show on his face, perhaps even something forgettable. Instead, he looked… striking. Blue eyes that made me lose my balance for a moment, as if the role-play had turned the tables and I was the nervous one.
We spoke. Slowly at first, then with little bursts of laughter. The way he glanced at me, shy yet insistent, turned even the simplest exchange into the way I flirt — alive, uncertain, and far more exciting than either of us had expected.
When he finally asked, tentative but certain, “Shall we go upstairs?” I agreed far too quickly, cheeks warm from my own impatience. In the room, we sat side by side on the bed, words circling in polite half-sentences. I placed my hand lightly on his leg, half testing, half offering. He froze, startled, but not rejecting.
“Do you want me to stop?” I asked softly.
“No,” he said quickly, his voice almost breaking, “I’m just surprised.”
His low self-esteem puzzled me. How could someone so handsome doubt himself so much? I told him as much. He blushed, deflected, tried to laugh it off.
So I kissed him. Just a gentle meeting of lips, nothing staged, nothing dramatic. A small peck that sent sparks running through me. His eyes widened, and then softened. I whispered, “You are exceptionally handsome,” and kissed him again.
What followed was less about roles and more about discovering each other slowly. His nerves melted with each touch, his compliments stumbled out in a rush, and my own professional calm gave way to genuine warmth. We stayed tangled for what felt like hours, lips brushing, hands exploring in careful, reverent strokes.
At one point, he paused, almost overwhelmed, and asked with a sincerity that made me ache, “Really… you think I’m enough?”
“Yes,” I told him simply, holding his gaze. “More than enough.”
We lay there afterwards in silence, listening to the city hum beyond the curtains, neither of us eager to break the spell. It struck me how quickly a simple role-play had shifted into something that felt uncomfortably real — the warmth, the doubts, the way his touch lingered as though he was still convincing himself I was really there.
Later, as I slipped out into the night, I couldn’t help wondering what other firsts I might stumble into in this line of work. Little did I know, my next call would take me into something far more daring — the heady excitement of First Tastes of a Threeway in Mayfair.