Some Dating Stories

EDIT TO ADD: a friend suggested I add a warning at the top of this post. The wording is theirs, but I basically endorse it. “Warning: The author of this post describes speedy seductions that rely on context and body language to understand what women want without asking directly. It works for the author and his sexual partners, but imitating the author’s seduction style could result in serious boundary violations if you aren’t unusually skilled at understanding context and body language. Err on the side of not committing sexual assaults.”

There’s a genre of dating discourse which I wish were more common, in which people just tell detailed stories of their own flirtation, courtships, dating, hookups, sex, fights, relationships, etc, etc. People tend to instead write about abstract lessons learned and takeaways and models, but so often those lessons and takeaways and models just don’t match my actual observations (of myself or others) at all. So I’m left thinking “ok, clearly this person is Missing Something, but maybe I am also Missing Something, so what the heck is going on here?”. Without their raw data, their actual detailed stories, I don’t have the pieces to put together an accurate model.

Anyway, in a recent comment, I mentioned

Going through the list of women I’ve slept with, the median is around 30 minutes of direct interaction between first meeting and sex.

… and apparently a whole lot of people are very surprised and confused at this. So I guess it’s a good time to write the genre I want to see. Here are some stories from my own life, which I think are pretty representative of my experiences.

Be warned, this is definitely going to be NSFW.

Story 1

I was at a fusion dance[1] in the Bay Area.

Background: I’m a pretty good dancer. At that point I’d been partner dancing for about 15 years. I’d also broken up a month earlier, so I had a sudden influx of time on my hands, and I’d been going out dancing more regularly than usual—maybe once or twice a week. On this particular evening, I was definitely in a In The Market sort of mood, keeping an eye out for sexual opportunities.

As usual, I rotated around dancing with different people each song. There were maybe two or three girls who seemed particularly into the dance, and who I asked for another. A couple of those cases involved very intimate “micro” dances—basically, you dance in a tight hug, with very small torso motions in time with the music.

Mid-late into the evening, with maybe an hour left, I went back to one of the girls I’d had a couple micro dances with. When dancing, she had quickly dropped into a trance-like headspace that I now identify as subspace (a BDSM term which I didn’t know at the time, but which is also common for follows in close partner dances). That seemed promising. I asked her to dance again, and we stood in a corner in close embrace, me leading small motions to the music, her in a trance state following. When the song wrapped up, I whispered “care to dance another?”, and we did. And then another. And then I didn’t even bother asking if she wanted to keep dancing, we just kept at it for eleven songs in a row until the event ended.

We stood there looking at each other for a minute, foreheads pressed together. She was still coming back to full awareness. “I need to get to bed tonight, but we should probably exchange contact info” I said eventually. She agreed.

I don’t think I have the original text chain anymore, but our texts went something like...

Me: I want to dance with you again. Preferably somewhere more private, where the norms do not prevent my lips from stopping before they reach your neck.

Her: So you felt that way too...

Me: What’s your schedule look like?

[… a week passes, with no response...]

Me: Hey, you ok?

Her: Sorry for the silence. Just, um, look I need to be honest with you, I recently separated from my husband. And I’m really excited about you but I don’t want to mislead you, I mean I am still married, but we broke up and it’s still very fresh.

Me: Not a problem. I’m recently out of a ten year relationship myself.

Her: Oh! Sorry to hear that. Anyway yeah, I’d really like to get together.

Me: Are you free <list of evenings, blah blah blah, there followed some logistics>.

(Probably the original texts were less compressed than that, but that was the general gist.)

On the designated evening, I picked her up at her house, around 6 PM or so. We drove about half an hour to a restaurant I like, generally chatting, getting each others’ basic background stories. I don’t remember the details of conversation well enough to recount them.

One moment I do remember was at the restaurant. She was looking nervous, and I said so. She replied that, yeah, she was here with a guy she barely knew, yada yada. So I took both her hands, looked her in the eye, and said roughly “I promise that I will leave you better and stronger than I found you. That is my number one priority, everything else is secondary. I can’t promise that nothing will suck along the way, I can’t promise you won’t get hurt, but I will do everything I can to leave you better and stronger in the end.”

That seemed to help her, a lot.

From the restaurant, we drove back to my apartment. It was somewhat-nicely decorated: string lights on the ceiling, a cool art piece on the wall, big open space for dancing, a pretty French-cafe-style small table and chairs in the corner. (My current place is rather a lot nicer, though.) I put on some music, and we got straight to dancing.

At some early point I asked “Are you hoping I tear off that dress?”. To which she smiled playfully, and replied “Mayyyybe”. I still think of that moment every time someone says “consent means an enthusiastic yes” or “maybe means no”. In fact, I remember thinking of that moment when she herself enthusiastically cheered someone saying “maybe means no, consent requires an enthusiastic yes” at the opening of a sex party some months later.

Anyway, we danced. The first two or three songs were pretty normal fusion dancing: close embrace, micro movements, etc. I would occasionally run a finger down her spine, or make a point of breathing out with my lips near her neck right below the ear. A few songs in, I escalated to kissing her neck, pulling her head back by the hair, and generally running my hands around. I paused at one point to give her safewords, and poked a pressure point until she used them, to make sure she knew she could. She responded well to a little pain, so as we went back to dancing I bit the spot where her neck met her shoulders, and she clearly liked that a lot. Another song in, we made out. Another song or two, and I started to gradually remove her clothes, and both kiss and bite her torso. A few more songs, and eventually I just dropped on a knee and started to eat her out.

She didn’t stay standing very long once that started.

I alternated eating her out and biting her, while pinning her arms down on the floor, or sometimes holding her down by the neck. At the time I didn’t know her well enough to confidently tell when she was or wasn’t orgasming, but with the benefit of hindsight I know she came quite a few times.

Meanwhile, I, uh… somewhat irritatingly-to-me was not getting hard.

I never did manage to get it up that evening. That was how I realized I was burned out, at the time. But I sure did give her a good time. Good enough that she came back the next night. And the night after that. We dated for about a year and a half, seeing each other about once a week on average. There was always sex, usually for at least an hour. Sometimes we went out and did other things too, sometimes we’d chill and watch a movie, sometimes she’d just stay the night and we’d fuck for hours. The carpet of that apartment probably still has glitter in it from her, and her underwear hung from my string lights for months before I moved out.

After that episode, I made sure to stock viagra, and I use it more often than not, even when I’m not stressed. Sex is a lot more fun that way.

Tying back to the original motivator for this post: total direct interaction time between meeting and sex was maybe 3 hours, tops, spread out over 2-3 weeks? An hour of dancing that first night, some texting, an hour-and-change of driving and dinner, then the gradual ramp up to sex.

Story 2

This was the first evening at slutcon. Again, there was fusion dancing. I was dancing with a woman who I’d seen before, she was generally in the Bay Area rationalist/​EA social circles, but I’d never interacted with her much.

This being slutcon, I felt more free than usual to physically escalate in the public dance space. She was clearly into it right from the first song, so I danced another few, quickly escalated to neck-biting and hair-pulling, and three or four songs in I pinned her against a wall and made out a bit.

After a little making out, I leaned in to speak quietly in her ear.

“There’s a secret room in one of the buildings here, with a black stone table in it. I want to bring you to that room. And then I want to pick back up the dancing. I want to kiss your neck and bite your lip and slowly peel off that hot little outfit you’re wearing, all while we still dance. I want to give you safewords. And then I want to pin you down on that stone table, stick my thumb into the pressure points along your thighs hard enough to make you gasp. Bite your breasts, leave a bit of a mark. Eat you out, make you squirm. And then I want to fuck you in that room, long and hard. Interested?”

She was silent for about a minute, while we continued to make out. I’m not sure she was even verbal at that point, she was clearly pretty into things. I eased up on the making out a little, and eventually she said “yes, I’d like that”.

There were some minor logistics, but we fucked basically as advertised. We didn’t go for very long by my standards because it was late; maybe 15 minutes of foreplay, 15 of oral, and then half an hour of outright sex? Since then, I’ve also fucked her in my apartment once, and ate her out at a sex party.

Total direct interaction time between meeting and sex was maybe 30-60 minutes, depending on how we count it.

Story 3

This story I’ve told before.

It was also at slutcon. Usually I am pretty committed to not trading sleep for flirtation, but slutcon was a container for experimentation, so on this occasion I stayed up late. And so, around 2 am, I found myself in a hot tub with maybe 8 naked people, mostly guys. There was a girl there who I’d briefly seen in one of the presentations, and I think I danced with her for one song earlier in the evening. (She goes by Chesed online, and writes at slutstack. She has also publicly written about this occasion and linked to my account, so I’m not going to maintain anonymity here.)

During a lull in conversation, I said “Chesed, what’s your deal? It seems like your brain turns off whenever someone touches you.”. She replied roughly “no, I don’t think that’s true at all”. (Thanks to her account, I know that she was actually thinking “Yes! Exactly!” and in fact she felt quite surprised and flattered to be seen.) Unfortunately she totally failed to convey any playfulness, so I let it drop for a bit, even though I did not really buy her denial.

Maybe ten minutes later, another lull in conversation, I decided “fuck it, it’s slutcon, we’re supposed to try things” and gave it another shot. I crossed the hot tub to sit next to her (still at a comfortable distance) and asked if she wanted to cuddle. She was quiet for a moment, then said “I’m not sure”, so I replied “take your time, I’ll be here”. Over the next 15 minutes or so, she first let her toes touch my toes, and then legs, and then gradually moved closer. I just stayed in place, sometimes making little circles on her skin with whatever body parts were touching. Eventually she was in my lap, and I was tracing patterns on her with my fingers, but not yet touching too personally. As predicted by my original comment, her brain seemed pretty off, she was kinda blissed out.

At that point she opened her eyes and sat up briefly, and said “has everyone done their homework yet?”. This was a reference to the slutcon “homework assignment” given in the opening session: ask to touch at least one woman’s boobs. It was meant to kick all the shy guys into being more forward than usual, which was part of the point of slutcon. Anyway, I am not so dense as to miss a hint that strong. I chuckled, said “ok, ok, I get it”, and proceeded to grope her boobs. Two adjacent guys in the hot tub also took the opportunity to come closer and grope her a bit, and she happily melted back into her blissed-out state.

Things continued to escalate gradually. I applied a little more pain—some scratching, some pressure points, some biting. She clearly liked that. I advised one of the other guys to pull her hair a bit. Another guy and I each fingered her while I held her by the neck, all while she was still on my lap. Eventually, with the fingering getting pretty thorough and me biting her breasts, she politely excused herself and left.

A few days later, one of her boyfriends messaged saying that I should fuck her, and also provided some useful background info regarding her tastes. (If you haven’t read her blog at all, suffice to say: her tastes lean very rough and rapey.) Arrangements were made. I will not go into the details of that encounter here, but suffice to say that it was maybe five minutes before my cock was in her mouth. Equipped with better background info, I gave her safewords up front (and made sure she could use them) and then got very rough pretty quickly, and she sure did like that.

Total direct interaction time between meeting and sex: about 30-60 minutes, depending on how you count it.

Story 4

A month or two after hooking up with Chesed, I got a message on LessWrong:

Hi! I got redirected here from your date me doc. (Disclaimer—I am probably not ambitious or multi-talented enough to fulfill the partner role for you in a LTR—but) You seem like a very interesting person and I want to pick your brain over coffee or something. My Twitter is [redacted] and also this account uses my real name so feel free to internet stalk me and make sure I’m not a psycho.

The name rang a bell. I replied:

Are you the “[name]” who the girlchat-collective told me was looking for a hookup on Thursday night?

and she answered

Guilty 🫣

([Chesed] didn’t say who she reached out to but makes sense it was you.)

Let it be said: Chesed really comes through for her friends. Good woman. I replied back:

Sounds like you should pick my brain postcoitally, then. I do tend to be a lot more open after railing someone for an hour or two, and girlchat probably has good judgement about how well our tastes match. Though admittedly it might take a little while before you’re able to ask coherent questions.

What’s your calendar look like?

And she answered:

(Pretend for the sake of my pride that I’m not that easy to get but also yeah let’s do that)

There followed some logistics, and I sent a hot smutty paragraph detailing what I intended to do to her (similar to the stuff I said in story 2, above, though more expanded).

We arranged the date, she showed up directly to my apartment, and it was straight to foreplay (similar to previous stories, but more roughness earlier). Chesed really nailed the matchmaking, our tastes match very well, and she’s still one of the partners I see most often. When together, we usually fuck, generally pretty rough, some hypnosis thrown in more recently. Occasionally we go out on a date, e.g. to a show or an escape room, or just stay in and cuddle/​chat/​make out. My experience of affection is probably different from other peoples’, but whatever thing I identify as affection, I feel a lot of it toward her. She’s great.

Direct interaction time from first meeting to sex: under 30 minutes.

Story 5

There is only one person I’ve slept with who I interacted with directly for more than five hours beforehand.

We met in college. She was two years behind me, and we were both into the partner dance scene. We ended up platonic friends, and spent most of our social time together in a small group with a few others.

Around the time I graduated, she started to angle for a less platonic relationship. And I have to hand it to her, she really worked for that one. I was still a virgin at that point, had never had a romantic relationship at all, had never even been on a date. I did not know what to do with any of this.

For her part, she was also a virgin, but had a long-term boyfriend from high school. Even before I dated at all I knew polyamory felt far more natural to me than monogamy (claiming ownership over someone else’ love life feels Just Wrong!), so I had no problem with her obvious pursuits when she had another boyfriend.

Anyway, she called every day after I graduated. I visited her, then she visited me, and we escalated physically each time, but verrrrry slowly. It was almost a year after my graduation that we finally had sex, both losing our virginities.

I was with her for ten years, mostly de-facto monogamous. Some of it was good, some of it was quite bad. Overall, in hindsight, it was the worst relationship I’ve had and probably an unusually bad relationship; there were unfixable problems which I now know to avoid upfront. The sex was not the only problem, but it was pretty bad by my current standards.

Direct interaction time from first meeting to sex: years.

  1. ^

    Fusion is a partner dance, and it’s particularly sensual/​intimate as partner dances go. There doesn’t have to be lots of close contact, but there usually is.