First Time's a Charm

The piece I was originally going to post today went by the wayside (long story), so instead I’m putting up something from the archives.

This is a piece about bad sex. Specifically, it’s about the first time — well, more or less the first time — that I had sex with another woman. What with it being a story about bad sex, I feel compelled to say two things: (1) I’m very glad I stuck with the “having sex with women” project despite a laughably bad first experience (an important lesson to remember when you’re sexually experimenting), and (2) Yes, I’ve learned a lot since I was 24.

Please note: This piece discusses my personal sex life — in particular, my sexual history — in quite a bit of detail. Family members and others who don’t want to read that stuff, please don’t. This piece was originally published in 1997 on Fishnet.

First Time’s a Charm

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Okay. I was 24, which explains a lot. I had just broken up with my husband, I had just gotten into therapy, and the only time I’d ever had sex with another women had been at an orgy with my boyfriend when I was in college, which explains even more. So I answered this woman’s personal ad; I don’t remember now what it said, except that the headline was “Creamy Petite Asian” and the ad said she was looking for sex, not a relationship, which suited me just fine.

So we meet at the Mediterraneum, this quasi-beatnik cafe in Berkeley, and right away it’s awkward city. We have pretty much nothing to say to each other — she doesn’t read much, I don’t watch much TV — and while she’s reasonably attractive, she’s not exactly setting off the old sprinkler system, if you know what I mean. Plus, this is maybe my second time answering a personal ad in my life. Plus, I’m acutely and grotesquely self-conscious, hyperaware of the fact that “I’m dating a woman, I’m dating a woman, I’m dating a woman,” and way- hyperaware of my near- complete inexperience with said gender. Plus, this is a really shitty and difficult time in my life; I’m basically an aimless, passive, wounded bundle of neuroses, and I get awkward and tongue-tied at the drop of a hat. Plus, I want desperately to seem cool, and as we all know, wanting desperately to seem cool is pretty much an ironclad guarantee that you won’t.

Highway overpass
So there we are, drinking our coffees at the Mediterraneum, trying to find things to say to each other, with long awkward pauses in between blurts of failed communication, and lines of conversation whizzing past one another like cars on an overpass over the highway. At one point she says something about how she hasn’t done this very much before, and I blurt out in a flood of relief, “I’m so glad you said that, I’ve hardly ever had sex with women before either,” and she gives me this withering look and says, “I didn’t mean that I’d never had sex with women. I’ve been doing that for years. I meant dating women in public.” Great. Score one for Greta in the “seeming cool” portion of the competition.

Failing to find a hole in the floor of the cafe into which I can crawl and die, I sputter inanely for a bit instead and grasp for some other topic of conversation. We chat awkwardly for a bit longer, I’m trying to think of a graceful way to get the hell out of there, when she says casually:

“So, do you want to come home with me?”


This catches me completely off guard — or would have if I had been even remotely composed and on-guard at the time. It’s definitely unexpected; with the possible exception of, “I am Anna Karenina, true ruler of the glorious Russian Empire, and there are bats in my underwear,” it is pretty much the last thing I expected to hear her say.

The thing is, an honest answer would have been, “No, actually, I don’t. You’re not really my type, and I feel totally ill-at-ease and like a complete moronic geek- dork with this whole situation in general and with you in particular, and if you don’t mind, I think I’d like to go home, bang my head against a wall for a few minutes, and then go make a big joke out of it with my housemates.” On the other hand, I’m 24 and a dyke virgin (well, almost), and if I don’t take her up on her offer I will never, ever, ever have another chance to have sex with another woman as long as I live. Besides, I want to seem cool — remember? — and saying “No” to a reasonably attractive woman you just met who wants to take you home and fuck you is definitely Not Cool. Besides, at this point in my life, I’m really bad at saying “No.”

So I say, “Um… yeah. Sure. Okay.”

“Great,” she says. “My motorcycle’s out front.”

Well, at least I get a motorcycle ride out of it. Truth is, I’m actually pretty excited — terrified of doing the wrong thing, and utterly clueless as to what the right thing might be, but excited nonetheless. It’s not really a sexual excitement per se — it’s more of a getting- on- a- bus- that- you- have- no- idea- where- it’s- going excitement — but it’ll certainly do for the moment. We get on her bike and head to her place in Oakland; she puts my hands down at the bottom of her belly, and I assume (wrongly, as it later turned out) that she wants me to feel her up, and I think that would be a pretty cool ‘n sexy thing to do, so I try to get my hands into her pants. She’s wearing skintight jeans, though, and I succeed only in working my right hand into her waistband, where it presses firmly against her bladder for the duration of the trip.

Christopher cross
So we get to her house, and the first thing she does is flip on the radio. Lite rock, less talk. Or maybe The Quiet Storm; I forget. Right away, whatever shreds of a mood I have are blown into hamburger. There is no way in hell I can get in the mood with Christopher Cross on the radio. I drop my purse and my jacket on the floor, and stand there paralyzed in the middle of her bedroom, wondering what the hell I’m supposed to do next.

I honestly have no memory of how we got our clothes off and got into bed. I assume she managed it somehow. There’s no way I could have made it happen; I was far too busy doing my imitation of a deer on the highway to have done anything so aggressive and forthright as taking my clothes off. And sadly, or perhaps mercifully, I have very little clear memory of what we actually did once we got there. I didn’t have the faintest idea what I was doing, and she was offering no clues. “Asking clearly for what you want” was obviously not in this woman’s vocabulary (to be fair, it obviously wasn’t in mine, either). She was more of the trial-and-error, “grab something and play with it and see what happens and hope for the best” school of thought. And I sure as hell wasn’t about to ask her. I wanted to seem cool — remember? — and saying “I feel kind of awkward and don’t know what you want, why don’t you tell me” seemed like the absolute pinnacle of uncool.

Hall and oates
And telling her what I wanted was definitely out of the question. Mostly what I wanted was for her to turn the damn radio off. My memory of that evening consists mainly of awkward, start-and-stop fumblings and an acute consciousness of my own incompetence, punctuated every now and then by the awareness that yes, indeed, that really was Hall and Oates on the radio.

The one vivid memory I have of the actual sexual encounter was of me going down on her. She was very close to coming, and she started pushing back hard on my forehead, a move that I interpreted to mean, “Stop, please.” So I stopped. I even patted myself on the back a little for having read her body language so well. Wrongo. Boy, howdy, was that ever the wrong thing to do. She sort of wound down, and a few minutes later she said in this kind of snide, frustrated voice, “Do you always do that?”

“Do what?” I asked.

“Stop right before someone’s about to come.”

“Uhhhhhh…” I retorted.

Car radio
We didn’t say much after that. She gave me a ride home in her truck; she kept her eyes firmly on the road, and I stared out the window and brooded. Christopher Cross came on the radio again, and she sang along as we pulled up into my driveway. “Ride, ride like the wind…” We parted with some conspicuously insincere noises about giving each other a call sometime; she vroomed away in her truck, and I hastily trotted up the stairs and into the living room where my housemates were playing gin rummy.

“So how’d your date go?” one of them asked.

I plopped down on the sofa, buried my head in my hands, and burst into giggles.

First Time's a Charm
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12 thoughts on “First Time's a Charm

  1. 1

    I take it that Hollywood producers are not beating down your door to buy the rights to this story. It’s well told, but it doesn’t quite fit into Hollywood’s fireworks-the-first-time, happy-ever-after mold, does it?

  2. MAK

    Kinda glad to see this, because in the era when I first began dating women (late 80s, early 90s), it was taken as given in my crowd that sex between women was going to be automatically good, Thankfully we at least had Joann Loulan who acknowledged that just being two women was not enough. As an awkward 23 year old who had never had sex with anyone at that time, my first sexual encounter was pretty pathetic.

  3. 4

    Well, Chaplain, it isn’t exactly a happy and elating story, is it? Most people watch movies to get away from all this “realism” stuff! It’s informative, sure, but that is taste few people have.

  4. 5

    Hi Greta! Okay, this has nothing to do with your post, but I was over on slacktivist lurking round the whole big theism/atheism thread that’s going on right now. And one theist on there are making an argument that seems to break down something like this: “You can’t judge theology by the standards of physics, in the same way you can’t judge literature by those standards. It’s a different discipline.” And then I start having an argument with the theists in my head (yeah, I do that too).
    Me: But if you’re saying that God has an effect on the physical world, then you’ve got to treat him (her, it, whatever) as a physical manifestation, and therefore subject to the laws of physics!
    TIMH: But literature has an effect on the material world too. A performance of Hamlet is a physical manifestation of a literary text. But no-one suggests that people who have an emotional reaction to Hamlet are therefore misguided. Or that any study of the text must be done via double-blind trials. So why are you saying that for theology?
    Me: Errr… I’m going to have to get back to you on that one.
    I really hate it when my imaginary debating partners defeat me.
    Help me out here, Greta, you’re much more able to reason these things through than I am. Could you use your insight and logical powers to blow away the mists that beset me?

  5. 6

    I will if I can, Claire. My schedule is pretty tight for the next few days, though: I won’t even have time for much blogging.
    If it helps you: Here’s a piece I wrote on exactly this subject: what aspects of human experience are an irrational, emotional, intuitive response appropriate for, and for what aspects are logic and reason and evidence appropriate.
    My argument in a nutshell: For matters of opinion and subjective experience, the emotional, irrational, intuitive approach is fine. But when it comes to questions of what is literally true in the real world that we all share, that’s when you need to try to filter out bias and subjectivity, and focus on evidence and reason. As centuries of human history and science have borne out.
    The piece is titled “‘A Different Way of Knowing’: The Uses of Irrationality… and its Limitations” and here’s the link.
    And the Hamlet argument is just silly. If you’re going to discuss people’s subjective responses to the content of a performance of Hamlet, then an emotional, intuitive response is valid. (Although I would hope you’d at least pay attention to “objective fact” issues, such as the historical context that the play was written in.) But if you’re going to discuss what is physically happening on stage — the forces of gravity, the mechanics of body movement, the motion of sound waves in space — then nobody cares, or should care, what your opinion and intuition are, unless you can back it up with evidence and logic.

  6. 7

    In spite of my being het, this post really, really resonates with me. I am in the process of ending my marriage, and sex with other (younger) men is definitely on the agenda. Trouble is, I got married to the third person I ever had sex with (dumb, dumb, DUMB) and my husband and I haven’t been exactly adventurous.
    So now I’m this 40-year old pseudo-virgin, thinking about playing Mrs. Robinson with a bunch of college boys, and I know my first attempts are going to be a disaster. Hell, all my attempts might be disasters. But I have to try, so it’s good to know that even the superstars of sex have had their off days.
    Peace out.

  7. 8

    Thanks, Greta. I really enjoyed that. My first time went rather well–I got my introduction to sex from a much older woman–but when I decided to strike out on my own with my less-experienced age-appropriate girlfriend, it was like the blind leading the blind. It’s like I’d been learning to dance with a woman who knew how to lead in reverse. I knew nothing about leading.
    I’m also glad I stuck with it, and I hope I’ve improved over the years as well.

  8. 10

    Thank you! That sorted me out. See, I kind of felt like there was something wrong with that argument, but I couldn’t see what. This is something I get a lot, and it’s often hard for me to work out if it’s me not wanting to accept something because it doesn’t suit my worldview, or if it’s because the argument itself really is wrong or stupid.
    That’s why it’s so great to have someone around who’s better at working through things logically than I am!
    Much gratitude,

  9. 12

    Kudos for a great story (I second what hoverFrog said!).
    I thought something was wrong with me when my own first time ended up being more like trying to start a car on a cold day than racing down the interstate. My then-girlfriend was considerably more nderstanding!

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