Holy shit, that was a hot date.
Serena knew we were going to a hotel; I didn’t. I mean, I thought it was likely, but I wasn’t sure, not by a long shot. She arrived about twenty minutes late for our reservation at a yummy sushi place. She wore a sexy, greenish-blue camisole that featured her tiny breasts beautifully, black leggings, and a black jacket. Her boots were chunky, lifting her a few inches higher. Even in the boots, though, she was five or six inches beneath me. And I’m not tall.
As dinner ended, I said to her, “Do I have your permission to book a hotel?” She raised her eyebrow. Our eyes locked, and she nodded, a tiny little nod, giving a giant quantity of permission.
Twenty minutes later, I sent her up to the hotel room with instructions to edge with the vibrator I had brought her, and if she ran out of patience, or if she found herself too close to coming, I told her she should start writing. When I arrived, fifteen or twenty minutes after sending her upstairs, she had written about one paragraph. All it said was that I was coming up quicker than she had expected.
For the first forty minutes or so, we lay on the bed, and I just teased her, tracing the outline of her blue, cut-out panties with my finger, running it up and down the seam, pressing lightly against her clit. She shuddered and came more than once to the slightest touch. We talked about her work, about the challenges of a relationship. I’m a deviation from her norm. We kissed a lot. At a certain point, I rolled over on my back and told her I wanted her to lead with the kissing. I wanted her to kiss me the way she wanted to kiss me.
Everything was tender on this evening.
She told me that she can get quite wild, and she’s read enough of my blog to know that I can too. But this was not an evening for that. This was a get-to-know-you evening, one in which, although she was submissive and I was dominant, the form of my dominance was gentle, sensual, patient, teasing. She told me she likes that I’m bossy, and I am. I told her what to do with her body. I tossed her around on the bed a little, but not too much. No part of the evening was violent in any way. I playfully tapped her cheek at one point, and she shook her head. That’s not for her. Her ass? She likes that spanked, but no marks, please.
After a couple of orgasms at the hands of my hands, I shuttled down the bed and planted my head between her thighs. I pulled off her tiny thong and dove in. She tasted sweet, and shuddered with orgasm after orgasm. Some of them came with a finger inside of her, some with two. At least one with my thumb in her ass. I pressed down on her pubis. I pinned her down by her chest. I held her thighs back against the bed and prevented her writhing. We took lots of breaks. We talked a lot. We learned a lot about each other. About our respective mommy and daddy issues. About our histories.
We talked about my relationship to straight fucking. I told her how it’s really not generally my preferred form of sex. At some point, I predicted that I might depart from my norm with her, though. And with my cock rock hard at a certain point, I told her I wanted to grab a condom. I got up, fished them out of my bag. She had seen them in the side pocket when I had offered her weed earlier in the evening. I fished in the main compartment, and she corrected me. “They’re in the pocket,” she said. I grabbed the condom, came back to the bed, and she lowered her soft mouth back onto my cock. I held her head gently, but with enough firmness to indicate, I think, what I might be capable of. We had talked about face-fucking, and agreed that that was perhaps a future night’s activity.
A few more minutes, and then I said, “Get on top of me. I want you to ride me.” She climbed on, and it was only a few thrusts before her first orgasm. Then we added a vibrator (one I had brought as a gift for her, to the restaurant) to the mix, and it was just the beginning of the night. And a few more orgasms followed, with each one her pussy clenching and expelling me. Several times she gushed, sometimes a little, but once, enough to drench the bed.
More conversation, more cock-sucking, a little more of my devouring her. My orgasm came late in the evening, much later than either of us had imagined, and it was actually at my hand. “I’m not ready to have your cum in my mouth yet,” she said. “I want it, but not yet.” “Where do you want it?” I asked. She motioned to her abdomen. Then, after some more attention by her mouth, I said, “What about in a condom inside of you?” And she nodded. She climbed back on. And once again, it wasn’t fifteen or twenty seconds, three or four good thrusts before she expelled me, and fell over with her final orgasm of the night.
“Did you come?” she asked. I shook my head no. Alas, her mouth was where my cum wanted to be, and deprived of that target, I wasn’t able to come, either by her mouth or her hands. And so, in the end, while kissing her as she ground on top of me, I stroked my cock to a giant release, coming all over both of our abdomens.
“We need a shower,” she said. And we did. We got in the shower, sudsed each other up, dried off, and continued our conversation. A little more kissing, a little more teasing.
And finally, at about two in the morning, nearly seven hours after we first kissed hello, we said goodnight in the dark.
The first time I wrote this post, I omitted the fact that I handed Serena money. The evening would not have happened had I not paid her. When she pointed this out to me and asked me why I had left it out, I gave a partial answer. I said it had something to do with my shame. That’s true, but incomplete. In the months my blog went dark, as I’ve written, I descended. Some of that descent was conscious, and some, in a retrospectively familiar way, I managed not to see in spite of how glaringly obvious it was. My capacity for self-deception is enormous.
Twice in the years since this blog began, I have paid a woman to have sex with me. This was the second time. I’m crystal clear that it will be the last, at least in this jag of shame and confusion. But I didn’t want to write about it. I didn’t want to admit, to see in print, the truth. I can color that truth, make it a little less shameful, and a little hotter. It is true that I desperately wanted Serena. That the idea of not feeling her mouth on my cock, of not tasting her cunt, was simply unimaginable to me. And it is true that my desire, my ardor, was different in kind from what I’ve felt in a long time. It’s also true that that desire had a pure, non-commercial aspect to it. Even as I handed her the money, even as I agreed to pay her, I could feel the cost of that desire. Not the financial cost, but the psychic cost, the wound that paying inflicts on me at my own hand, eviscerating so much of the pleasure, eradicating it, replacing it with remorse, regret, guilt, and shame. I didn’t want to admit this, not to myself, not to you.
Serena and I talked about it a lot. It’s complicated, I know, to be in a position where I’m telling someone who does sex work that I want what she offers for free. But the truth is, and this is where perhaps there’s some redemption for me, it’s not so much that I want it for free, although I do. No, more than that, it’s that I don’t want it for money.
And, a final postscript: this was the last date with Serena at which money changed hands. But, thankfully for both of us, it wasn’t our last date.