Lauren, who was twenty at the time, still lived with her parents in a humble, brick A-frame house north of Waveland. The parents were gone, or so I assumed. She never mentioned them one way or the other. She answered the door in a button-down shirt and bare legs.
“Hello, birthday boy,” she said to me.
In any other context, I would’ve been so aroused. This was the stuff of my fantasies, a woman who could be pinned up on my bedroom wall seducing me—me!—but I was feeling limp in every sense of the word, wilting under the pressure.
“Don’t be nervous,” she said, making a stark appraisal of my reaction. She took me by the hand and led me through her house, a small kitchen with dishes in the sink, a radiator with peeling paint, a bowl of kibble, and cat litter. It calmed me. Seeing the mundane in her life brought her back to earth, or at least that’s where I tried to maintain my focus.
Once inside her bedroom, she made it so easy. I had no context, other than the occasional foray into internet porn or sex scenes from movies, where everyone is so smooth and confident.
She took it slow, drawing close to me, letting me smell her perfume, gently brushing her lips against my neck, running her hands up the sides of my legs. She started swaying, though there was no music, humming something I didn’t recognize.
She turned around, pressing her buttocks against my crotch, her head against my shoulder, as I silently begged for an erection, to get past the nerves and get into the moment. She took my hands and cupped them around her breasts and moaned.
“You feel good,” she whispered.
Then my hands took on a life of their own, squeezing her breasts, cupping her neck, running through her hair, pressing against her silk panties.
And then, batter up, I was in the moment. She had helped me get there, had guided me through the first curves and turns, and now I was ready to take the wheel.
I wish I could say that Lauren enjoyed hours of ecstasy. My best estimate is that it was four minutes—and that was with me trying hard tohold it in—and I’m not sure any particular moment would have qualified to her as ecstatic. I didn’t have any idea how long I was supposed to hold out, not the slightest concept of how to bring a member of the female species to orgasm.
But she made me feel like she’d had the time of her life. She wrapped her legs around my back and held me there, afterward, for a long time.
“I like feeling you inside me,” she whispered.
The truth, I was more relieved than anything.
She brought in a couple of beers and we drank them and talked on her bed. I was a few months away from college, and she told me she was saving up so she could afford college, too. We talked about music, about baseball, and one beer became another. That was one more beer than I’d ever drunk, but the buzz from my first sexual encounter was far more intoxication than any alcohol could provide.
We were standing by her dresser, looking at pictures of her from high school, when she looked at the clock on the wall. “My parents will be home in about an hour,” she said. “Sometimes they come home a little early.”
“So the birthday boy should probably get going,” I said.
“Mmm.” She put her hands on my chest. “You’re not a boy, you’re a man,” she said. “So how ’bout you fuck me one more time before you leave?”
She sure knew how to punch my buttons.
—
And now, here we are, nineteen years later. I am rapidly approaching that cliff. It’s not too late to turn back. That’s the beauty of it; until I jump, I can always change my mind.
My life has been okay. I put myself together and moved on. I can keep that life, nice and safe, more or less, boring and uneventful, maybe, but meaningful to me. As long as I can still teach, even if I’m run out of my law school by Dean Comstock—I can find some school, prestigious or not, it won’t matter as long as I can still teach and talk and write about the law.
If I take the plunge, I don’t know where I will land. It might be the biggest mistake of my life. It could well be the end of me.
43
Vicky
I sit in a high-back chair outside the ballroom at the Peninsula Hotel, where inside, eight hundred of the wealthiest people in Chicago mingle and play casino games to raise money for autism awareness. I am not dressed for a night like this and have no invitation, but I wore a dress, anyway, to generally fit in.
In my lap is my phone, in my ears, AirPods. I look like I’m watching something on my phone. I am not. The screen is blank. But the words from inside the Gold Coast Room come through the AirPods with decent clarity:
He:“So are you staying here tonight?”
She:“No. Are you?”
He:“I have a suite.”