Meet Cleo

Cleo matches my type, almost to a t.

She stands 5’1″. Her breasts, she tells me, are “28-C,” but, since that can be hard to find, she wears a 32A or B bra, most of the time. Long, lustrous, brunette hair that was straightened when I saw her, but clearly naturally wants to curl.

She is smart. Self-assured. Accomplished.

She has known she was submissive since she was four years old, she says.

She listens exquisitely, learns exquisitely. She doesn’t presume anything. “What should I call you?” she asked, at a moment when far too many have called me “Sir” or “Daddy.” I hate that, because inevitably someone who calls me “Sir” or “Daddy” already has slotted me into a role, a position – one that many before me, and many after me, will fill.

We all (and I certainly) engage in a bit of fantasy when we engage with sex, a bit of fantasy that what we are doing is unique, special, when in fact, there’s an inevitable aspect of repetition to sex, across pairings, across time. Still: if you call me “N,” I’m reasonably sure I’m – if not the only one ever to have gone by that name, at least one of a very small number, and that name will lodge, firmly, in your mind as me. Call me “Sir” or “Daddy,” though, and I’m just one among many.

Back to Cleo: she knows, intuitively, how to avoid the pitfalls of poor communication, of poor submission. She said “no” to me today, in the midst of what might be a difficult conversation in which we’re working out the parameters of our relationship, and even then, at that moment, she did it in a perfect way, declining what I had asked to see (three minutes of her teasing her clit through her jeans), while offering something close to that (that she would do as I asked, but not send me a video of it, and instead, would tell me about it).

This kind of response makes my cock so fucking hard.

I don’t know if Cleo and I will have a second date. Our first I haven’t yet written up, but I will say, it featured us unexpectedly – for both of us – repairing to a hotel room where we began the process of getting to know one another’s bodies. And let me tell you, hers is fantastic.

Her face, too: high cheekbones, long cheeks. Bright brown eyes (“poop brown,” she called them). A wide mouth with full lips. (“People have told me I look like Julia Roberts,” she said, disavowing any such resemblance. “Don’t be silly!” I said. “You’re much prettier.” And she is.)

She also looks a bit like my first serious college girlfriend, J, whom I saw for nearly two years, and who was preternaturally gorgeous. And tiny. J’s mouth was a little less wide, her lips a little more full. But J was gorgeous. And so is Cleo.

My fingers are crossed with/for her. My hopes are high.