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

Personal adsOkay. 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 overpassSo 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?”


BatsThis 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.”

MotorcycleWell, 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 crossSo 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 oatesAnd 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 radioWe 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.