Listen: I know it was my idea to go on a Sex Nerd Sandra podcast listening spree while we were sitting together in Los Angeles traffic. I know I’m the one who put on the episode about prostate play, and suggested that we listen to one-hour and thirteen-minutes of two people talking about the pleasures that lay just beyond the butthole (I guess). I squirmed around like a dork, side-eyeing you and giggling like a 7-year old hearing about pee-pees. You sat there driving, straight faced, and staring ahead.
I know we’ve been dating for over a year. And that I told you, initially, I was pretty open-minded sexually. I know we’ve done some stuff other couples could never mutually agree upon.
I’m so into you—but I just cannot put my finger up your butt.
It killed me when I told you this while we were shoveling pre-beach breakfasts into our faces at House of Pies, that you sighed quietly and got all solemn and stared down at your picked-apart Huevos Rancheros that kind of looked like puke for what felt like an hour.
“I didn’t realize it was off the table,” you said disappointingly. The waiter came over at the utmost height of awkwardness and asked if everything was OK. I said yes, loudly and quickly, to ward him off, while you nodded your head.
“Except my girlfriend is denying me a 10-minute orgasm,” you muttered as he walked away.
It’s not that I want to withhold pleasure from you! Or like I don’t know what to do: I’m supposed to reach around, slide my lubed-up finger down your buttcrack and stick the tip of my finger—with a clean, short, filed nail, of course—into your sphincter, create a hook shape to help the anus open up, wait until you’re loose or whatever, go in a bit further, and find that plum-sized sack that’s your prostate that’s up towards your bellybutton. With the pad of my finger, I’m supposed to go tap, tap, tap.
And I can change speeds: Taptaptaptap.
Or go around in circles. Or slide in and out (slowly!).
We both know I don’t think male anal play = gay. Except if this wasn’t a widespread societal belief, I’m sure heterosexual couples would be all up in each other’s asses.
I wanted to vomit and cry the first dozen times I gave blowjobs. But we also both know I’ve long since gotten over that…
The prostate is supposedly the mystical “g-spot for men.” If you denied me g-spot pleasure, let’s be frank, I’d break up with you. I’d scoff about your selfishness with my friends over vodka drinks and tiny little appetizers, and we’d all lady-cackle and call you a loser.
So why can’t I bring myself to kill the double standard with a little of the old phalange-in-butt, in-out?
Plain and simple, I’ll tell you why: Poop.
I’ve heard you shit, and you’ve seen me pant and heave and pace in that eerie psych ward waiting room in Brooklyn while the schizophrenic man strapped to the gurney in front of us screamed and cried. We’ve sobbed a bunch together, and mutually agreed upon which piece of dirty laundry in the room would make the best cum rag.
But if I touch your poop, I swear to god. I don’t know how I could ever make eye contact with you again.
Again, with the gay thing—or let’s just talk anal sex in general: My squeamishness with anything in the butt started long before I considered prostate play. That ex-boyfriend from a couple years ago (yeah, THAT one) who persisted I take it from behind was always met with a buttload (excuse me) of questions along the lines of, “But… poop?”
“If I shit on your sheets, I’d never forgive myself,” I’d tell him. I’d peruse message boards about going to anal pleasure town out of curiosity, and come back to him with questions. “Am I really supposed to ‘clear out,’ and shoot lube into my ass with a turkey baster?”
He’d give me a look like I had a bit of crap on my face. “No, Caitlin… no…” he’d say. Still, I couldn’t be convinced.
And then one day, with the next dude, I’m wasted and I think why not? We never talked about it, there was no pressure, and his sheets were always disgusting, anyway.
(Sorry, I know you don’t like to hear about that.)
So what I’m trying to get at here is that I really want to give you the most intense orgasm of your life. I want for you to have healthy innards, and if a prostate massage promotes that, well OK, then. But I just need some time to warm up to the idea, and what I really want to know is: Could you clear out, and then can we go out drinking tonight?