When I was 16, there was a girl at my high school with the same first name and the same birthday as me. For this purpose, let’s say my/our name(s) is/are Jenny. She was “the popular Jenny,” the skinny, blonde Jenny, and I was the slightly overweight, frizzy-haired mall-Goth Jenny.
Other Jenny lived in an upper-middle-class township where all the moms wore makeup, and worked part-time if at all, and went to the Dominican together over summer break. I lived in a teeny affordable housing apartment with my family that always had the neighbors’ weed smell wafting through it. So I pretty much spent half my time in Hot Topic pretending to like KoRn because my best friends did, and the other half of the time deeply, painfully jealous of Other Jenny.
So one day Other Jenny came to class with a Coach purse, one of the ones with the C’s on it that my friends always made fun of. (This was the transitional period between the “popular girls have hideous Coach purses” phase and “popular girls have hideous Dooney and Burke purses” phase.)
I had been dimly aware of sugar babies because of things I read online, and it always interested me. I didn’t consider myself particularly attractive then, and although at the time I saw that kind of transaction as purely goal-oriented/only to afford the tacky C-stamped swag that Jenny had, it actually had two benefits: The swag, obviously, and the idea that I was cute enough that someone would want to buy me for a sex thing, which of course is so sad. (And wound up leading to a decade of therapy.)
I was a virgin at this time and figured that if I aimed for some specific fetish I could avoid actually having sex with someone in this situation. Given that the men would likely be older, I figured the whole daddy/daughter spanking thing would be the thing that was least sexual to me that could get me to the Cs the fastest. I put an ad on Craigslist (College co-ed girl looking to be spoiled – f for m) and made a fake e-mail account, which was a whole thing because it was pre-Gmail (remember Yahoo?). I did not specify the amount of money because I am a nice girl and thought that was rude. So like, THAT was my boundary, you guys. I did mention Coach, telling the guy who replied a "gift card would be cool."
He picked me up at Penn Station. He was maybe 42. He looked sort of like Ed O’Neill and lived in the Financial District. We didn’t speak much, and it didn’t seem like he did this that often. He was paternal but also awkward and shy, not like one of those schmoozy guys who shows up with a backseat full of Mike’s Hard and 50 feet of Kevlar rope on "To Catch a Predator."
Nearby, a mom was showing her daughter how to put on lipstick. I remember very clearly thinking: Come ON. How on the nose is this? This is like a freaking Paul Haggis screenplay.
I can’t remember what he did for a living, but I remember him being way less wealthy than I thought he’d be — his apartment was really modest, and had bare walls, like it was just this impersonal place he slept in nightly. I guess I thought it would be like “noveau riche finance guy who’s balding a little and lives in a super-modern classic six,” not a normal work-a-day man who has bills to pay, compounded by an unfortunate and expensive fetish for spanking young girls off the Interwebz.
This is going to sound like a lie but before we went to his apartment he took me to Ground Zero. I swear to God this is true. We looked at a bunch of rubble together, and he talked to me about what 9/11 was like for New Yorkers, how the mayor was dealing with it, etc. I kept glancing around at the other people, positive someone was magically going to identify us as a creepy Craigslist blind date and tell my parents that their daughter was starring in a Lifetime reality series called "Sex Work Lite: Virgins Who Are Scared Edition."
He spanked me on my bare ass with a heart-shaped paddle and kept asking me if I was a bad girl. I didn’t know what the answer should be, so I was like “Nnnnn….yeah?”
He actually tried to pay me in a MetroCard, which in retrospect is hilarious (or sad? Or both), but I wheedled and said “Daddyyyyy” a bunch until he gave me the gift card. It was for way less than I thought it would be — $70 — which was more demoralizing than the actual spanking. In fact, this really wasn’t a traumatizing experience in the least. The motivation behind it, a.k.a feeling so damn unpretty, was the problem that landed me in therapy later. But the actual experience? I’ve been way more emotionally scarred in the long-term by some of my normal adult pro bono sexual interactions.
I could only afford a wristlet. Remember those? It was brown and had the Cs all over it and I LOVED it. Freshman year of college it got stolen when I left it on a bed/coat area at a party. I recently mentioned this theft (not the story behind it, obviously) to my boss, a fashion editor/lovable snob, and she sniffed, “That’s for the best.” If she only knew.