A Cucumber Up my Cassoo and My First Anal Orgasm

Sorry for the size, could not find a less thick one

I’ll shove a cucumber up my ass!

It was a light bulb moment. Newton had his apple. I went with the gourd family.

I was 18, new to New York, and drunk on the D train. Drunker than usual. I had been embarrassed that night. There was this comedy group at NYU, and I was its sound guy. It was my job to press the play button on a cassette boom box so that, after the punch line of a sketch, R.E.M. or Fine Young Cannibals would kick in. It was 1989.

In rehearsal that night, I’d fucked up a cue. I’d played “The Humpty Dance” after a sketch meant to end with “Back in Black.” One of the group members said, “Kevin, you don’t know this cue by now?” Then he had started singing, “If you don’t know it by now,” like Harold Melvin, and the whole group chimed in like the Blue Notes: “You will never, ever, ever know it, ooo-wooo!”

 

It was silly to be so embarrassed. I was too sensitive. I’d grown up knowing I was gay and not knowing I had ADHD, but always in this tug-of-war between being proud and mortified to be so different. So when the group members went out drinking after rehearsal, I drank deep. Then they all hooked up with various folks of the opposite sex on their dorm room floors, and I, still hiding from them that I was gay, headed home to the hole-in-the-wall I shared with my older brother in Brooklyn.

What could I do to feel better? I’d recently found out about prostate stimulation, and how it supposedly took orgasms to a whole new level. Like, not just turning the volume knob up but also the bass, the treble, and the wah-wah on the guitar. I’d never tried it. I didn’t have a penis on hand to help me out, so I went for the next best thing: a penis-shaped salad topping. 

It was the perfect plan. I’d get my mind off my embarrassment from the show rehearsal and pound some of this closeted sexual tension out of my system with a cuke up the ole wazoo. Two birds, one stone.

Then I remembered that my brother and I lived on dollar slices and Guinness. The last thing we’d have in the fridge were nutrients. And I lived in this quiet Hasidic neighborhood. Surely no grocery would be open at 4 a.m. As the train reached the station, all hope was lost.

Then, for the first time ever, I noticed the sign on the Waldbaum’s grocery by the station: “Open 24 Hours.” I rushed in as if I had a life to save. The whole place was silent. Just flickering fluorescent lights. And the only other soul I saw was this half-asleep stoner dude at the cash register. He watched me sprint to the produce.

There was a nice selection of cukes. I took a moment, like Goldilocks, thinking, Not too big and not too small, and when I found the one that was just right, I rushed to the register.

That’s when it occurred to me: Might this look a bit odd? Rushing in at 4 a.m. for nothing but one cucumber? But I’d spent all my money on Guinness and Jägermeister shots and had only a few coins to spare. Would this be another embarrassment? What might the stoner dude think?

As nonchalantly as I could, I placed my item on the counter for checkout. He looked at it. He looked back at me. But he remained expressionless. He wearily took my change and punched some numbers into the register. As he was bagging the gourd, I thought, I got away with this! He doesn’t suspect a thing!

 

LUKE WINKIE

Yep, Trader Joe’s Cashiers Are Up To Exactly What You Suspected

 

But when he handed me the bag, he raised an eyebrow.

He said, “Enjoy your … salad.”

I know we both found it hilarious, even though we both kept a straight face.

 

About 20 minutes later, I had my first anal orgasm. To say that I enjoyed my salad would be an understatement. The thing is, I more or less knew I was gay well before kindergarten. I’d been masturbating to imaginary versions of fellas I knew from school since I was 9. But the actual mechanics of male-to-male erotic activities were still mysteries to me at 18. As it turned out, the cucumber adventure was one of the first of my lifetime of trials, errors, and triumphs around sex. I’m in my mid-50s now, and one of the things I’m most thrilled about is that, especially in the realm of kink, I continue even these days to discover new ways to have intimate fun in the bedroom. And to this day, I sound like the entire choir singing the “Hallelujah Chorus” when I climax from prostate stimulation.

I think of that cashier when people judge me, poke fun at me, or try to shame me for being me. He’s a reminder that I don’t have to wallow in shame and hurt when that happens. I share stories about my sex life on my podcast RISK! and on my social media quite freely now. People constantly say things to me like, “What a relief to hear you being honest about that stuff. It makes me feel like I have nothing to be ashamed of either. Like it’s OK to be different and I can just laugh it off if people judge me for it.”