I’ve lived in New York City for a little over 10 years. As any of the other writers for The Frisky can tell you (and have written about over and over), dating in this city isn’t as easy as a walk in Central Park. In a city of eight million people where the single women outnumber the single men by roughly 150,000, the stakes are high and the pickings slim. Having been out there floating in that sea for longer than I would have wished on most people, archenemies excluded, naturally I have found myself in sexual predicaments that, tragically, I probably won’t be forgetting anytime soon. Actually, there’s a very good chance I’ll never forget some of these scarring and haunting forays into the ridiculous. And because of this, I think the best way to deal is to share them with someone besides my therapist.
1. The Footjob: I had heard of the footjob; I had also heard that dumb guys sometimes try to stick their penises in your belly button instead of your vagina. In other words, for me, it was one of those urban legends you hear about in high school, and one that I never thought would be requested of me.
I had managed to live a whole 27 years without encountering even the slightest suggestion from a dude that this was his desire, so when it happened, I laughed. I asked him if he was serious; he asked me how he could not be? He loved feet and couldn’t think of anything sexier that me masturbating him with mine. So, with each of us on our backs, but facing each other when we propped ourselves up, I proceeded to give him a very physically awkward footjob, as angling one’s legs properly in order for the soles of the feet to rub in an up and down motion hardly comes natural. As he shut his eyes and moaned, I rolled my eyes and stared out the window. Eventually — i.e. almost immediately — I got a charley horse in my leg, so I stopped and politely told him that was the first and last time I would rub his dick with the bottom of my feet.
2. Armpit Licking: To this day, I’m still trying to figure out how this could be appealing to anyone. For starters, there are two flavor choices, neither of which sounds particularly appetizing — deodorant or body odor? Call me crazy, but lapping up either of those does not a sexy time make. However, that didn’t stop this particular fella, as he proceeded to lap up all of my Secret solid from one armpit, before moving on to the next. I clearly remember him saying, “I hope you’re enjoying this as much as I am.” I just nodded. I was enjoying it, but only because I couldn’t wait to tell my friends about it at brunch that weekend.
3. Toe Hickeys: Mr. Footjob really couldn’t get enough of feet. One night, he came over with Hershey’s syrup, not for an ice cream sundae as you might assumed, but because he wanted to drizzle the syrup over my toes and suck them. I had a roommate in college who was really in to having her toes sucked, so this wasn’t a completely new or even bizarre concept for me. But what was bizarre was the strength of his suction; he wasn’t just trying to get every ounce of Hershey’s syrup off my toes, but it felt as though he wanted to take some blood and flesh too. When I couldn’t bear it anymore, I asked him to stop, washed my feet and found that my toes were covered in hickeys. At 15, a hickey might be a badge of “Hell yeah, I got some bitches!”, but in your ’20s, you really start to question your life decisions. Especially when those hickeys make impossible to wear sandals for a week in the dead of summer.
4. Period Cunnilingus: I had been in a non-serious, strictly friends with benefits situation with a guy for a few months. On more than one occasion, he had expressed his disappointment over the fact that I never had my period when we hooked up. The reason for that was simple: I’d ignore his booty call when it was that time of the month. But one night I ran into him at a bar and brought him home, knowing that I had my period. I had never had period sex before, but figured since my sheets were navy blue, if he was down, I’d go for it. Why not? YOLO! I wasn’t on my back for more than 30 seconds when he pulled down my underwear, and with his tongue all ready to do some serious licking, he headed straight downtown where things were looking mighty bloody. I pulled him up and told him he didn’t have to do that considering it was that time of the month. Instead of being repulsed, he told me, “Nothing tastes better than a bloody pussy.” With that, he dove in, I closed my eyes, cringed, silently questioned his sanity, and after just a few minutes asked him to stop. He looked up at me; his mouth and nose covered in blood and asked what was wrong. “Everything,” I said.
5. Tapioca Titty Fuck: Ah, the titty fuck. I have engaged in this sex act probably less than 10 times in my life, despite having the perfect rack for the job. However, on one such rare occasion, my then-suitor wanted to use lube to get things nice and slippery. I was game; well, as game as I could be for a titty fuck. But the problem was he had no lube; no olive oil, Vaseline, not even any lotion to be had. What he did have, however, was Swiss Miss tapioca, which, for some reason, I allowed him to smear between my boobs and on his dick so he could get that good ol’ fashioned slippin’ and slidin’ thing down. Unfortunately, this was actually the second time in my life that tapioca had been worked into a sex act, the first being in college after watching “Varsity Blues” and not having any whipped cream on hand.
6. The Groomer: It wasn’t until a couple years into my life in New York City that I started getting Brazilian waxes on a regular basis. Up until then, I’d do it occasionally when I had the money, but I wasn’t religious in my waxing practices. The presence of some bush led a guy I was dating, fairly seriously, to ask if he could shave me. “It turns me on so much,” he said. Admittedly, I was intrigued by how he could be excited by such a thing, but wasn’t very sold on the idea of having someone, besides myself, wielding a razor near my lady bits. But a few days later, there I was, spread eagle on his bed (we really should have done it in the shower). Always one for picturing a dramatic ending, as I lay there, I couldn’t stop envisioning how my clit would look in his hand if he accidentally lost sight of what he was doing and fucked up. Never again.
7. Whisky Nipples: I used to meet up with the bartender I was dating at closing time when he was the only one left at work to lock up. We always had fun with no one around: danced , fucked in the office, drank the expensive booze, you know, your usual after-hours behavior. He really loved two things: whisky and my boobs. One night, after too many shots, he asked me to take off my shirt and lay on the bar. I thought we were just going to have sex on the bar, a cute story to one day tell the grandkids, you know. But instead, after I removed my bra, he poured whisky over my nipples and feverishly lapped it up, like a man stranded in the desert coming upon a pool of water. Later, an argument ensued when I was told that there were security cameras in the main part of the bar, and that the incident would be forever on tape. In that moment, all dreams of running for president went out the window.
I don’t necessarily regret any of these things, because they were, at least now in retrospect, really, really funny. Besides, I’m pretty sure I’m not the only out there to have gotten a charley horse from giving a footjob. Come on, I know you’re out there … and if not, share your most ridiculous sexual encounters in the comments!