I Pegged a Trump Supporter

"I opened his mind... and his butthole"

Playboy recently removed all essays from their website. This means countless essays, including my favorite piece of written work, are no longer available online¹.

Last night, I attended the Authors For Harris² call, filled with 45-minutes of tangible tips that writers can take to advocate for Harris. This call inspired me to republish my Playboy essay, Pegging for Politics, here on Substack. Yes, this is an essay about sex. But it’s also about critical thinking and the value of across-the-aisle discourse.

I resisted my writerly urge to re-edit this essay because I want it to remain a time capsule of where my writing skills and my budding activism were in June 2019. I was 3.5 years sober, still finding my voice as a writer, political thinker, and mental health advocate. I had no idea I’d write a book called Dry Humping, become the internet’s The Sober Sexpert, and be interviewed by Dan Savage³.

Reader, I encourage you to engage in uncomfortable political conversations if you have the capacity. Your approach doesn’t need to include pegging (although you absolutely can!), but maybe provide intellectual stimulation through discussion rather than monologing about why they’re wrong.

Ask them to expand on the Fox News talking point they just repeated or inquire why they’re so passionate about a certain issue. People want to learn, but they often don’t know where to start or are afraid to ask “the wrong⁴” questions.

Essentially, keep the door, and your butthole, open.

XO,

Tawny

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Here’s the Essay

We met on the tarmac in Iceland, awaiting take off for New York City. I was on the aisle; he casually slid past me into his window seat. Obligatory smiles were exchanged. As the flight attendants’ safety video began, I realized there was nobody seated in between us. We had the whole row.

We bonded over similar experiences at the Blue Lagoon, still in awe of how soft our faces still were after hours of face masks in the exotic man-made abyss. He asked about my favorite parts of Iceland. I recalled how much I loved the Reykjavik Museum of Modern Art and the History of Punk Rock Museum (which was appropriately located in a repurposed but still dingy underground public bathroom). His stories of drunken bar scenes and late nights with his hostel-mates showed me that we were on different wavelengths.

I had quit drinking a year and a half earlier, I told my new friend, Tanvir. On this trip, when my friends went to bars, I did my own thing. Except for when they went to a bar that we were pretty sure was brothel. That was my scene. Plus the bar served non-alcoholic beer. The three of us hung out in the dimly lit bar listening to European techno music while observing beautiful, minimally dressed women take men up the red velvet staircase.

At one point, one of the women sat with us. Her accent was thick, revealing her Russian roots. It was the summer of 2017 and only a few months prior, I was at the Women’s March in Washington D.C. I didn’t want to have a casual conversation with this woman, I wanted to know what she thought of American politics and Donald Trump. My friends were annoyed, but I was entertained. She thought Trump was a joke; she felt bad for the American people.

Throughout the night, I had my eye on another woman. Her dark hair, fair skin, and tight leather skirt intrigued me. I wanted her to talk to me, to take my hand and guide me upstairs. I would have enjoyed my experience with her, paid her for her work, and went on with my night. But I was scared to pursue her.

Tanvir's eyes grew. He was enjoying my titillating story. Hours flew by as we flew across the Atlantic Ocean. Our six-hour flight felt like several dates. We covered everything from work, family dynamics, last serious relationships, personal goals, and had our first argument: a debate on time management. I adamantly claimed that with proper scheduling and making lists, one could get a lot done. His retort was based on time being a social construct.

Three hours into the flight, he asked if he could kiss me. I said yes. He unbuckled his seatbelt, moved into the middle seat, and pressed his lips against mine. Holy shit! I’m making out with a stranger on an airplane! We held hands while discussing what our first actual date would be.

A week later when I was settled back into my routine of being a writer who works retail and he settled back into his job in finance, I texted him, “Face mask and chill?” I was proud of this proposition; it was clever and it referenced our shared love of face masks at the Blue Lagoon in Iceland. He came over later that night, but soon enough we learned the only things we had in common (besides wellness treatments) was a physical attraction and making out on a plane. Luckily, it was a resume for a perfect friends-with-benefits situation.

We hooked up on a few different occasions before it happened.

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One night he came over while I was watching that episode of Broad City. “What’s pegging?”, he asked. Once he realized that pegging meant a woman penetrated a man's anus with a strap-on, his jaw dropped. “I’m not going to do that with you”, he announced.

“I never asked, but it’s something I’d like to try with someone at some point,” I responded.

“That’s fine,” he said, “but not with me." Later that night in bed, he told me that he had given it some thought and he’d be willing to try pegging.

A few days later I got a text from him.“I bought a strap-on," he said. I was giddy. Holy shit, this guy really wants me to peg himI told Tanvir to masturbate with the toy a few times before we played with it together, per an experienced friend's advice.

“This won’t be like Broad City and you don’t want to be there for the first time something goes in his ass; that needs to be done on his own,” my friend thankfully told me.

I went to his place a few nights later. He ordered Indian food (amateur move, according to my anally-experienced friend) while we watched Game of Thrones. I’d never seen an episode before, but I was down to see what the hype was all about. He made himself a vodka drink, offering me one. “I’m sober," I reminded him.

“You don’t even drink vodka?!” It was yet another confirmation that I’d never develop romantic feelings for this man.

After the show, we headed upstairs. I got in his bed. He tossed me the strap-on. The harness was black, adjustable. The removable dildo was red, silicone. Average length and girth. Just thinking about the fact that he masturbated with the toy turned me on. I pegged him. And we loved it. The first time was awkward, but we laughed through it. The awkwardness was all part of the fun.

Another night, after more pegging, our conversation got serious. We went all the way...politically. He made statements that struck a nerve; each one dropped like a bomb onto my living room floor. Derogatory comments about sex workers, for example. As a sex columnist who almost hired a prostitute in Iceland, I strongly disagreed and the conversation got heated. This discussion was a bit more heated than our debate on time.

More bombs fell. “Trump was a better option,” he said. My blood began to boil and I asked him, politely, to leave. I had heard enough. Then I remembered how politically confused I felt when I moved to New York City from Texas. I was lucky enough to have a friend listen to my ignorant questions without judging me. She kindly met me where I was without pushing her agenda onto me. So I decided it was time to pay it forward with Tanvir.

I told him that he could ask me anything he wanted about social politics. That I’d listen to him without judging him or his questions, then respond if I knew the answer. The next two hours went a little something like this:

He said, “I don’t get the trans community. Why can’t people just stay how they were born?”

I briefly explained the difference between sex and gender to Tanvir and urged him to do more research on the topic. I also let him know how offensive that question can be to people in the trans community.

He went on, “If two men can’t get pregnant, what’s the point in fucking?”

I retorted, “Are you fucking me to get me pregnant?”

He kept on, “Fair point. Why do people get into sex work? Why don’t they respect themselves?”

I’d recently written an article about the soft-sex industry so I spoke to the research I’d done. I told him that it’s a reasonable income source for some people. It’s like any job where some folks love it. Some folks do it because it works with their schedule or skill set. Some folks do it for the money. Or myriad other reasons one selects a line of work. I also let him know that it can be challenging for people in the trans community to find work due to ignorant state laws, so sex work is sometimes one of the few viable financial options.

The conversation impacted each of us. He admitted that he had formed opinions on issues that have never affected him so he never gave much thought to how said issues impact others. He didn’t use the word privilege but he seemed to grasp the concept. I gained some insight on what it’s like to be a straight, cisgender man in this political climate. I was also appreciative of my friend who showed me how to have a mature, productive conversation about politics instead of a circular debate that won’t get anywhere. Listening to each other can go a very long way. At least it did with us.

Over the few months we were hooking up, I questioned myself. Am I content with sleeping with a man who doesn’t care about politics? About the LGBTQ+ community? About other marginalized communities? I was fucking a Trump supporter, literally. My mind didn't feel good about it, but my body felt great. I learned that—like most things—it’s not black and white. Tanvir’s apolitical stance lied somewhere in the grey. He thought he was a Trump supporter because his family members supported Trump. Going with it was easier than questioning his own personal politics. He told me that I was the first person to give him the space to ask questions. I didn’t judge him for what he asked so that allowed him to access his true curiosity. I opened his mind and his butthole.

I continued to hook up with him because he was open-minded. As long as we kept the conversation light and the bedroom activity heavy, it worked. I’d peg him, he’d fuck me, then we’d snuggle while watching Rick & Morty until we fell asleep.

When I moved to New York City, I wasn’t much different from Tanvir. Though I’d always been a bisexual woman who’s an outspoken ally to other members of the LGBTQ+ community, there was still a lot that my privilege had blocked me from experiencing while growing up in Texas. I even voted for Mitt Romney in the 2008 election.

My time with Tanvir ended mutually; we both wanted to put our energy toward finding a serious relationship. He wanted a farewell fuck; I didn’t. So we didn’t. We haven’t spoken since.

If we met under different circumstances and solely discussed politics, I may have pegged him for someone else. But I remained open-minded while establishing my boundaries and was able to peg him just the way he was.

1. Unless you’re a WayBackMachine nerd like me

2. Led by

Catherine’s Newsletter

3. Savage’s listeners and readers coined the term pegging, which is now in the Oxford English Dictionary

4. I firmly believe any question that comes from a place of genuine curiosity or the desire to learn is valid—even if it uses offensive language. A curious approach is vastly different from someone who’s intentionally trying to be hateful or abusive through language.