The Cautionary Sex Story I Probably Won't Tell My Daughters

When I teach my girls about love and sex, I’m going to go way beyond the birds and the bees. I want to teach them about confidence, trusting your gut and staying true to yourself. I want to save them from learning everything the hard way, as impossible as that sounds.

Reflecting on my own awkward sexual past, I’m not exactly filled with shame as much as a deep desire to go back and smack myself upside the head. (But not the ass. You’ll see why.)

Right after college was the easiest time in my life to date, because it seemed like the whole world was young, available and looking (and not in a hunched over, getting carpel tunnel from swiping Tinder way). I was constantly meeting dudes. I could go to a dive bar after midnight and still pick up a well-educated Wall Street guy, or I could pick up the bartender. But for the purposes of this story, a Wall Street guy.

When I spotted Tim, he had already taken off his jacket and loosened his tie. I liked the way his hair flopped over his forehead, highlighting his wild eyes and booze-reddened cheeks. He asked for my number at 3 a.m. and used it by 11 a.m. the same day to set our dinner date.

I wore my perfect first date outfit: a long-sleeved, semi-conservative top, chosen to offset a very short, flippy black mini skirt and giant heels. I was self-conscious about my height (barely 5-foot-2-inches) and routinely wore sky-high platforms. Basically, I looked like a preppy stripper.

Tim took me to an Italian dive in the East Village. We didn’t know each other well and the conversation wasn’t exactly flowing, but I still thought he was cute. After a few glasses of liquid courage, I excused myself to use the bathroom. Unfortunately, it was located down a steep, narrow, concrete staircase of doom.

Given my inebriation and unstable footwear, you would suppose I might have grabbed the railing to steady myself. I did not. (I must have been clutching my clutch.) One heel shot out from under me, my skirt flew up and I landed hard on my ass, which smacked several steps on the way down until my momentum slowed. The pain made my eyes water. I stood gingerly and rubbed the tender cheek that I imagined was turning yellow and green on its way to black and blue.

When I returned to the table, now masking a limp, I didn’t say a word about my mishap. Nada. Today’s me would have been laughing through tears, turning my misfortune into a funny story that might have broken the ice and accelerated getting to know each other’s true selves. But young me was mortified. Young me wanted to preserve my mystique and be the kind of cool girl who would never lose her footing on a staircase or in life. Young me didn’t have a clue.

As I mentioned, my date and I barely knew each other, so the natural next step for me was to go back to his apartment and get naked, of course. The sex, from what I remember, was adequate. But at some point in the proceedings, Tim made like a future Christian Grey and started to spank my bare ass—right on the new bruise.

It’s incredible that I didn’t black out from the pain. It’s more incredible that I didn’t stop him. I let this relative stranger–who really had no business going the S&M route on a first date to begin with–hurt me. Of course, he didn’t know he was hurting me. He didn’t know me at all. I knew myself even less.

I think eventually I managed to roll underneath him, which got me out of harm’s way. The bruise healed before our second date. Our romance fizzled after three months, which is actually a pretty long time to date someone without ever showing him the real you. Ironically, one of the things that endeared Tim to me was the night he cooked and ruined our dinner with toxic levels of salt. I embraced his flaws while hiding my own.

Now that I’m over 40 and a mom, I feel both protective and pitying toward that 24-year-old girl who was so insecure, she couldn’t stand up for herself, especially lying down. I know my daughters will need to make their own mistakes, but I’d sure love to prevent them from making mine. If only there was a way to tell them this story without the spanking parts.

Oh, what’s that you say? By writing this for the Internet, I’ve basically told them already? I don’t know—the Web is a busy place. In order to find this 2015 relic someday, my kids will have to Google my name plus “embarrassing” and “sex.” Shit.

So, daughters of the future, know that Mommy was young once too, and this is what I learned: Your well-being is so much more important than your image. Be confident. Trust your gut. Stay true to yourself. And hold the railing on the stairs, please.