November 4, 2021

SEX ON THURSDAY | Can I Please Peg You (Platonically)

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I have always wanted to peg someone. Perhaps it is my raging penis envy, but I have long desired to be the penetrator instead of the penetrated. My mind raced with all the possibilities of my thrusts as the one in charge of the tempos and the depths like a maestro with her baton conducting an entire orchestra of anal amusement. Even if my provisional penis lacked nerve endings, I would be able to feel every tensing muscle and breath of my partner pulsing beneath me. The role reversal would be enough to make me cum in sync with the boy bent over my headboard. 

As luck would have it, I had a friend who wanted to be pegged as much as I wanted to peg. It was a match forged in hanky-panky heaven, the only problem was he lived in Chicago. So we planned it: I would go to the Windy City for fall break so I could flick the bean and see The Bean. 

We both trained mentally and physically. I watched the strap-on porn he sent me while he practiced with various buttplugs. One of which was stainless steel and he wore it out to lunch without anyone noticing.  He was stretching himself out, exploring his boundaries,and stocking up on lube. I was perfecting my pelvic thrusts with the perfectionism of a professional ping pong player. We seemed perfectly prepared for a night of pegging pleasure. 

When I arrived in Chicago, we met in a bookstore off The Blue Line train station. Down the street was a sex shop appropriately named  Pleasure Chest. Behind mirrored chrome display cases of gimp suits and masturbation gloves sat the wall of strap-on harnesses. Some were full leather g-strings while others were shaped like normal lacey panties except for the dildo hole, but all were modelled on plastic mannequin pelvises. 

My friend and I stood in front of this wall struggling to make our decision as if we were in the  line at McDonald’s. A quick look at some of the price tags revealed that the harnesses were out of our budget. Pleasure Chest staff sensed we needed help and showed us the most simple and cost effective beginner harness for 30 dollars.

The harness sat in its box when we got to his apartment. We climbed in bed and he showed me a new TV show he thought I’d like, but the whole time I kept glancing over at his collection of buttplugs erect on the windowsill. I was trying to find the perfect time between episodes to ask, “Can I please peg you?” But then he put on a cat show documentary. 

“I really want to fuck you,” I said with every sultry ounce of my being. He planted a kiss on my forehead and said he was tired, so we ordered Popeyes for delivery and we ate the chicken sandwiches in bed. The crumbs and Bayou Buffalo sauce were getting in the sheets as the bottle of water-based lube looked at me with lustful longing. 

Maybe he was tired or maybe he chickened out like the box of nuggets on the bedside table, but I learned a valuable lesson. Consent is ongoing. No matter how much someone wants something months beforehand doesn’t mean they want it right now. Sometimes they just want to be spooned as you listen to a book on tape. Even our shared, taboo desires can have missed connections and realignments. Even if you’re prepared for months, the moment can present itself and fade away into a Popeyes 10 piece meal… and you have to be okay with that. 

I flew home writing the six word story, “For sale: pegging harness, never worn,” as the faux leather strap sat unopened in my suitcase. But it doesn’t have to be a sad story. I discovered why I liked hanging with my Chicago friend to begin with, sans platonically pegging him. Who else would galavant around in ridiculous outfits and speak in fake Russian accents with me on the train? Anal penetration can blind us from what really matters in a person: their strange yet endearing personality. 

Currently the harness is crumpled up in my underwear drawer, patiently waiting for the right person, time and place. My dreams for it live on in my continued fascination with the realm of sexual mystery. 

Anya Neeze is a student at Cornell University. Comments can be sent to [email protected]. Boink! runs during alternate Sex on Thursdays this semester.