Diving in


Ashley was anxious. A reasonable sentiment, given that we had never met in person, had met on Zoom only once, and she was about to meet me so that I could devour her cunt. Given that she knew I was, within minutes of meeting her, going to ask her to go to our hotel room, get naked, open her legs, and wait for me.

She walked in to the bar. She was dressed (as I had instructed) ridiculously for the weather. A black dress that left her midriff, and most of her big, round, full breasts exposed. Not to mention 95 percent of the expanse of her legs. And it was chilly out.

She looked gorgeous. Her flesh was pale, white – Zoom does a terrible job rendering flesh, complexion, texture. Her skin is clear, bright. Her lips full, red (painted, at my instruction). She can’t stop herself from smiling: a big, wide, enthusiastic, contagious smile that brings to mind the Spanish word for smile: sonrisa.

As I waited at the bar, I ordered myself a Johnnie Walker Black on the rocks. They had a very conventional, limited selection of single malt scotches. And I had a flask-sized bottle of Ardbeg An Oa in my bag.

I ordered Ashley a glass of sauvignon blanc. Having not been with her previously, I didn’t know what her preferred beverage was. And, I didn’t much care. But I had the sense that she was not a dark liquor kind of woman. And I tend to shy away from fancy cocktails.

There had been a little bit of confusion about just where we were meeting. It was a bar in a hotel. But Ashley became concerned that I had skipped the bar part of the evening and sent her directly to our hotel. Although we had talked about a version of the date that might look a bit like that, I knew at least one drink was necessary. (It turns out that only one drink was necessary.)

At the end of her first drink, I turned to Ashley and said, “I’m gonna ask you a question. Your answer to it is not in any way binding to me. I’m gonna do what I want. But I do want to know the answer for my own information.” And I said, “Would you prefer to have another drink? Or would you prefer to go straight to the hotel?”

Ashley’s response was non-committal. Along the lines of, “I think i’m okay with either.” The truth is, her answer did matter: had she expressed even the slightest hesitation, I would have continued lubricating her with alcohol. But she did not express even the slightest hesitation.

“Okay, then!” I said, and fished the hotel room key out of my pocket. I placed it in front of her. “You know the hotel. I texted you earlier. It’s two blocks away. Room 205. I’d like you to go to the hotel room. Undress. When you’re naked, please lie on the bed, with your feet flat on the bed and your knees bent like this.” I illustrated with my elbow and my hand. She nodded in comprehension. “And play with yourself until I arrive, please. Do not come. But when you’re in that position and ready, text me. At that point, I’ll leave here. So it’ll be a little while before I get to you after you send that text.”

She walked out. I watched her delicious, full, round ass swaying as she did.

Giddy with excitement for the sumptuous meal that I knew awaited me, I got myself a second scotch. And took out my little notebook. In which I wrote the words of this post, up to the word “sonrisa.”

At about that moment. My phone vibrated. Ashley said, “Ready!”

I already had settled up with the bartender, so it took me all of ten or fifteen seconds to get my coat and hat and gloves together, to slide my notebook into my pocket, and to walk out the door. It wasn’t five minutes before I approached the hotel room. I had earlier connected my phone to the bluetooth speaker in the room, and as I approached the room, I reactivated that connection. And started music. (Radio Paradise, my go to, if you’re interested).

So poor Ashley had the sensation of hearing a phone connect and then hearing the music start before there was any sign of me. I waved my room key over the sensor. The door unlocked. I entered.

Ashley lay previously as I had instructed, and took her hands away from her cunt. “The music surprised me!”

“Keep playing with yourself. I’m not ready for you yet.” I poured myself another (little) drink. I plugged my phone in. Adjusted the lights slightly, grabbing a towel from the bathroom, and draping it over the reading light next to the bed.


And then, I dove in. As my tongue connected with her clit for the first time, as I took in the subtle scent and flavors of her cunt – sweet, and musky, yes, but quite subtle – it occurred to me that there was another universe in which I might have ratcheted up the anticipation, in which I might have teased her a little. Even just a tiny bit. In which i might have engaged in something resembling foreplay, before my tongue was on her clit.

This, though, was not that universe. I had waited long enough. I was hungry enough. This particular fantasy was the one I wanted to actualize. And for the next two or maybe, three hours, with no exaggeration, I licked and lapped and slurped and fingered her very pretty, very delicious, very responsive cunt.

Ashley had told me that her orgasms sometimes were elusive to her partners, though never to her. That she needed to guide men, or help them. I confess: I had not imagined I might be in this category. I’m confident. Cocky, even when it comes to my ability to intuit the pleasures and parameters of a particular pussy.

I did collect two three very powerful orgasms from her. I know it was two because she told me. In my mind at the time, it might have been none. It might have been twenty. What mattered, though? I had no doubt Ashley was enjoying my ministrations, and that was all I cared about. I wasn’t particularly orgasm-focused. I was, though, a bit confused: I knew from things she had told me, from videos she had sent me, that the way Ashley touches herself is entirely clit-focused, that penetration just isn’t a part of her self-touching. But when I slid a finger, or two, or three, into her cunt? Ashley’s whole body responded encouragingly, enthusiastically. Maybe I misread her signs, but I had the sense that the thing I might be able to do that would get her off was to fuck her hard with my hand/fist, to pummel her pussy with my fingers, pressing in as hard, as deep, as fast, as I could. It felt to me like the secret to getting her off would be sustaining speed/power/depth even longer than my arm stamina permitted.

But that third fourth orgasm did not seem attainable. At least, not by the likes of me. Ashley asked if she could touch her clit. “Of course!” I said.

Ashley, like many, imagines helping a partner as somehow a defeat or a failure. I don’t see it that way. To my mind, help is a good thing. Sex is complicated. And anything that makes it better – another hand, a toy, another person – it’s all good. (Though obviously, I have some more complicated feelings about all this, as I wrote above that I didn’t imagine I would “need” her help.)

So she touched her clit while I licked beneath her finger, while i fingered her. I kissed her. Rubbed her breasts. Or just watched. In any event, the third orgasm did eventually arrive.

“Sorry I’m so loud!” Ashley said.

“Loud?!?” I asked, in surprise. “I wouldn’t say you’re loud. Expressive. But not loud. At no point did I think, ‘Oh my god, our poor neighbors.’ Or. ‘I’m afraid someone’s going to come and bang on our door and ask us to shut the fuck up.'” And that was true. I did not have those fears.

After that third orgasm, we lay on the bed and cuddled a bit. We talked. About sexual experiences. About open relationships, about jealousy. Ashley is single. And was pretty curious to understand more about my relationship with T.

I answered every question I could. I talked about how, to my mind, jealousy is an inevitable emotion. That the idea of organizing one’s life to avoid any particular emotion just doesn’t make much sense to me. And how we tend to privilege jealousy in ways that I find unhelpful.

Finally, I announced my intention to get ready to leave. “What time do you get up?” I asked.

“Early,” she said. “6:15.”

“Oh, I get up earlier,” I said. “Five.” And together we dressed.

“I’m glad I brought sweatpants,” she said, characterizing that as having cheated somehow.

“That’s not cheating,” I said. “That’s sensible. I asked you to wear something ridiculous. You wore it. But there’s no reason you should wear it home. It’s cold out!” I pulled my slacks on, she pulled her sweatpants up over her legs. We grabbed the rest of our stuff.

I showed her the rope I had brought but not used. “Maybe next time, when you suck my cock as well.”

“I’d like that,” she said. I zipped up my bag and we walked toward the front door. As we approached the front door, I spun her around and pressed her against the door, taking one final kiss from her before emerging from our sanctum.

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