I Had Sex With A Famous Writer. Our Encounter Left Me Deeply Unsettled.

The author in 2009.He wanted me to sit on his face.“But I don’t feel clean,” I told him.“I don’t care. I like it a little dirty.” This author, whose words I devoured, was now greedy to taste me. I got into position, and he gobbled me up.I couldn’t laugh, but I felt ridiculous. Maybe I didn’t want to have sex with him; I just wanted to procreate intellectually. I’d much rather be fucking one of his books. How had I ended up here? And why couldn’t I let myself leave?I read the interview with the literary legend in BUTT magazine, one of my favourite indie publications, in which he described his open relationship with his partner and how he found younger guys on a site called SilverDaddies.com. “The thing is, when I was in my 20s, I found lots of men in their 40s and 50s to fuck me. And it was very, very exciting. I mean, some of them were extremely powerful guys… Physically and in the world,” he said in the frank Q&A.The idea made sense. I was now in my late 20s, so if I was going to get anywhere in this complicated world, I needed to catch up. Since I wanted to be a famous writer, did that mean I needed to meet and fuck older powerful men? OK, I’d try.Within hours, I logged on to the site and created a simple profile with a cute photo that showcased my blue eyes and youthful features. Within a day, someone who fit the author’s description reached out, and I replied, explaining that I knew who he was and that I was available for hooking up since I was in an open relationship as well. “I’m so glad you answered!” he emailed immediately. “Yep, I’m the writer. I’m enclosing a not very sexy pic. I live with someone, but we haven’t had sex in nine years and he has a lover so — well, that’s my story. That’s great you’re so open with your lover. Best way. I love your looks and your profile so let’s get together soon...”I was giddy. Someone I’d idolised for his mind was validating me. I told my boyfriend about it, eager to get his permission and approval.“Should I hook up with him?” I asked. “I’m not attracted to him, but I mean, should I?”“Sure, if you want to,” my boyfriend said. “Why wouldn’t you?”“Well,” I stalled. I was nervous. We’d discussed our version of ethical non-monogamy and mapped out boundaries. We started with three: no sleepovers, no repeats, and be honest, telling one another everything.The idea was to curb the possibility of emotional attachments. Cuddling in bed can lead to deeper feelings and is something more intimate, in our book, than fellatio. A regular sexual partner can also become a habitual distraction. The original intent was to ensure that we didn’t deny ourselves potential experiences that we’d later regret and then hold against each other. The three rules seemed sufficient. But then other rules — more like suggestions — followed. Since he shaves his head daily, no bald guys (I broke that rule). And because of his professional background: no architects (I broke that rule, but the hook up was with a landscape architect with great legs, so I didn’t think it really counted). And I told him I didn’t want him with guys who resembled me (that rule was also broken). Of course, those were just our fears that we could replace each other physically, and therefore emotionally, which hasn’t been true.In this case, it was definitely a unique opportunity. Yet it felt like I was trading my body for a chance to network, which already began to make me feel cheap. I’d always told myself that it’s better to regret the things you’ve done rather than regret never having done anything, so I reassured myself that I’d say yes if the author wanted me.The next day, I got another email from him inviting me to come by after work. The author’s apartment was a few blocks away from my office in Chelsea. I texted my boyfriend to let him know I’d be late, and gave him the address in case he got worried. Then I walked to the author’s apartment. You can always back out, you can always just turn around and go home, I told myself.I trembled as I rang his buzzer — nervous and afraid and not sure what to expect, but wanting to meet someone who was a hero to me, who had helped form my idea of what it meant to be a gay man with talent and a brain. But what if it was a trap, a joke, a prank? Or what if I couldn’t get it up? He answered the door with a jolly smile, still cherubic at 66. He kissed me — a strange, awkward, fumbly sort of kiss that immediately turned me off. Kissing is my biggest turn-on, and if someone couldn’t kiss the way that I liked, I’d often decline to go further. But I told myself not to let it thwart the plan. I pushed myself to try again.I noticed the books and the nice dark wood furniture as he led me to his bedroom. He kissed me again — the same tepid kiss that made my heart (and my dick) sink. Then he began to worship me. I was a prized possession. I kissed him again, trying to force him to soften up, let me use my tongue in a way that would feel more sensual, so I could get aroused. He undid my belt. He wanted me. I didn’t feel attracted to him, but it wasn’t hard to get me hard. I was 29 and forever horny. Plus, I’d had sex with older, unattractive men before. I told myself it was empathy: I wanted these men to feel happy, not rejected, and if I could give them some little piece of happiness, it felt like the least I could do. Fulfil a fantasy. Be a sex surrogate.Yet underneath that idea, I knew it wasn’t truly just me being magnanimous to an elder, since by taking responsibility for his emotions, I was the one in control. I wanted him to be happy. If I made him happy, then maybe we’d be friends, share some bond that started with sex but transcended it, brought us to some height of connection beyond the coital plane.Yet, at this point with the literary icon, I also separated from my body: Did we look comical? Certainly, we wouldn’t look sexy. Perhaps I looked perfect, golden and beautiful against his large, sagging frame. The idea of intense attention perked me up — I could do this! — even if I wasn’t sure what I was comfortable doing. I knew he was HIV-positive and into kink; he’d written about both topics extensively. Although I’d never knowingly had sex with someone who was positive, I knew enough about undetectable viral loads and how to have safer sex that I didn’t want that to negate this moment. Still, I remained bashful and timid. The author wanted me to be rough, to beat him with my belt. He wanted me to piss on him as he lay prostrate in the tub. “I don’t think I can do that,” I confessed.My weak limbs didn’t feel up to athletic exertions. “I don’t want to do that,” was what I should have said, but it made me seem like I was the neophyte, the passive one, begging off doing something that would please him. Always striving to be the good boy, I wanted to achieve and not disappoint in this case as well.We moved to the floor, and he jerked off. I averted my eyes, locked my gaze on his toes. My cerebral watchdog stalked us, sniffing at our two bodies — one fat, one thin — fascinated and repelled by our bestial embrace. I heard him grunt and groan. I tried to finish, so I conjured up a regular fantasy that usually got me off. “Wow, impressive. Nice job,” the author said. “Ha, thanks,” I replied with a coy grin. I basked in his praise, feeling like I’d been awarded a gold star for my efforts.Afterward, we both lay there on the hardwood floor and began to chat. He told me about a young hustler he’d met online and how he’d been sending money to him despite never having met. I wondered if he thought I was some sort of sex worker and expected me to ask him for money. Instead, I changed the subject and asked about his teaching at an Ivy League school and told him how my partner was getting his Ph.D. I wanted him to know that I was educated, knowledgeable, something resembling his equal, not a guy looking for a handout. “Actually, I have to get going! I’m having dinner,” he said, and mentioned another author known for her stupendous literary output that appealed to goth girls and emo-types. “Oh? That’s great!” I said and joked that he should tell her to stop writing so much. “She has so many books, and I can’t tell if any of them are any good.”“She can’t help it,” he said, chuckling.I felt like we had a conspiracy, some sort of important literary link that eclipsed our hookup.We cleaned off, put on our clothes, and promised we’d see each other again.Later that night, I received an email from the author: “That made me entirely happy! I’m off to school tomorrow — but later in the week?” I didn’t reply. Something had switched in me when I got home. My boyfriend was eager to hear the details, and I tried to make a sexy anecdote out of the entire situation, but I started to feel strange. What had I done? I’d embraced an idea of openness when it came to sex and sexuality: I was an ethical slut, sex-positive and non-monogamous. This had all been an equal exchange; it was OK. I hadn’t violated any personal moral code. The author had been a total gentleman, and everything had been consensual. I’d crafted my own dogma based on so many beliefs, but at the centre was the core neo-pagan tenet I’d incorporated: And it harm none, do what you will. But I’d miscalculated. I never expected that I could be emotionally harmed by my own actions. My boyfriend was eager to hear the details, and I tried to make a sexy anecdote out of the entire situation, but I started to feel strange. What had I done? I felt dirty, as if I had betrayed myself. I hadn’t wanted to have sex with him, but I told myself I did so that I could say that I did. I subscribed to the adage credited to Oscar Wilde: “Everything in the world is about sex, except sex. Sex is about power.” This had been entirely transactional. I wasn’t so naive to think that there was such a thing as unconditional love — or sex. But now I felt like a fool. Hadn’t my friends laughed and told me how I was “sexually generous”? But this wasn’t me being charitable, this was me wanting to conquer the author and reap the spoils of that successful encounter. Was I a sexual opportunist, having deployed my youth and vitality for communion with one of my heroes? I’d turned my body into a harpoon and launched it at this man who just wanted a fun time. I’d captured my white whale, and now I regretted it. I tamped down the disgust, telling myself I was better than that, and vowed to never brazenly use my body as a bargaining chip again.These feelings festered within me, but it didn’t affect my imagined mentor. He continued to reach out as I dodged his queries, coming up with excuses, not wanting to hurt his feelings with my rejection, not bold enough to tell him honestly, “I don’t think I’m ready. I’m still a boy, clinging to some myth of innocence. Can we just be friends?” We’d both been naked and vulnerable, but I felt like I lacked the psychic armour to handle another encounter. I’d fantasised about joining us together, my own silver daddy dream that’d translate into a fantastic intellectual union. I’d meet him and he’d pass on a spark that would inflame me. I’d keep that torch of creativity, nurture it until I could pass it on. But the reality wasn’t that nice and neat. Rather than achieving the connection I’d desired, it’d backfired. And it was all my fault.For years, I worried that I’d done some psychic harm to myself by putting myself into that scenario. As I pondered the impetus, I remembered the impact of novels that helped lead me to that confusing moment. Instead of picturing our naked bodies, my mind wandered to the used bookstores and thrift shops where I’d sought refuge growing up, feeling like a misfit in a small town in South Georgia. It was the mid-’90s: We didn’t have the internet yet, and I’d exhausted most everything I could find in the local public library. I’d burned through those card catalogs — everything from apocryphal Bible stories and psychic mysteries to unicorns and Wiccan pagan mythology — but the small strip mall shops and cute cottages crammed with cracked spines of castoffs still held surprises. I searched for sci-fi and fantasy series, graduated to Kurt Vonnegut and Tom Robbins. I needed to liberate my mind from anything that had a whiff of “classic.” That’s how I ended up with multiple copies of anything by Faulkner, Camus or Salinger, as well as “Jonathan Livingston Seagull,” “Zen and the Art of Motorcycle Maintenance” and other 1970s bestsellers that had lost their cultural currency. I used my dollars earned at my part-time Wendy’s job to save these volumes from a wasted life.I stumbled upon a trickle of gay authors that became familiar: Paul Monette’s ”Becoming a Man” showed up often; something by Felice Picano or Michael Cunningham; Andrew Holleran’s “Dancer From the Dance”; a ”Men on Men” anthology of gay shorts. It took me more than a decade before I realised that I had been unearthing the discarded libraries of dead gay men — that generation that perished as I was growing up during the AIDS crisis. This was the flotsam left after their families picked over the wreckage of their lives. Unsure what to do with these objects, they ended up here. I took it as my grandiose duty to collect, cherish, preserve them.The father of a high school friend treasured his dead gay brother’s collection, and he lent me those books from a shelf in his study: Edmund White, Armistead Maupin, Alan Hollinghurst, Christopher Isherwood, Larry Kramer. “Yes, my brother died of AIDS,” my friend’s dad explained. “Borrow any of them you want.” Up until that point, I’d never met an HIV-positive person, yet I had absorbed the lesson all around me: being gay meant certain death. The books became my education, a connection to my queer heritage. My friend’s dad became a mentor and quasi-paternal figure who counselled me as I strove to be the first in my family to attend college. His gentle reassurance that I wasn’t sick or discardable helped me survive those tumultuous teenage years. It wasn’t what I received from my biological parents.“I’m worried you’ll be alone. That you’ll get hurt,” my mom said when I sat down with her at 15 to officially come out. Amid the ’90s “culture wars” in the “don’t ask, don’t tell” era, I had the radical notion that I could dare to be me. “Two men can’t love one another,” conservative politicians announced on television. Gay men were the most visible they’d been in history, but they were cursed, afflicted, doomed. That’s what gay meant: lonely, no love, death. Although they were from a different era, reading these novels felt like an epiphany: love, sex, hope. Perhaps that’s why I was eager to do anything to meet the author of one of those pivotal novels. I wanted to be his intellectual progeny. Sex proved I had a connection — a real, palpable bond — to the men who had come before me. Hadn’t he befriended Foucault? Had they shared their bodies? Did that mean I now had a sexual bond with all the men those men had fondled and caressed, sucked and fucked? Without queer forbears to teach me the ways of my tribe, I wanted to feel a connection to my “family tree” — whether through their minds and books or a more carnal education.Nearly a decade after we hooked up, I attended a book event at which the author was present. By this time, I was an editor at a magazine, and I’d even met and befriended the writer’s husband while on a trip to Key West, where I was working on a travel story. We’d spent a night carousing his favourite gay spots, but I never revealed that I’d had that time with his husband in any physical way. Although I still hadn’t published a novel or had my own big literary splash, I did feel like I’d finally accessed this rarefied world in some fashion by regularly hobnobbing with bold-name writers and creatives. I dodged predatory men who tried to slither into my life and trade their influence for sex. I began to believe that I could elevate myself through my talents and force of will. So I felt semi-secure on my perch when I saw the author again. He leaned against a shelf of books in a literary agent’s impressive Tribeca loft, and I smiled in recognition. I noticed the twinkle in his eyes. He seemed smitten, and he flirted. He didn’t recognise me or remember that hour we’d spent naked together almost 10 years prior. And why should he? He’d famously had thousands of conquests. I wasn’t a chapter or a story in his memory. Lucky if I even rated a footnote. Now it was my turn to transform that afternoon together into a story — something that felt important and not just another squandered opportunity.Jerry Portwood is a writer, editor and journalist. He’s the founder of The Queer Love Project, a platform where LGBTQ+ people share their stories. Previously, he was a top editor at Rolling Stone, Out magazine and New York Press. He’s a long time instructor at the New School, where he teaches essay writing and criticism. He splits his time between his home in West Harlem in New York City and Cambridge, Massachusetts, where he lives with his husband. He’s working on his debut novel, “The Loneliest Boy in the World Saves Us All,” which he plans to publish soon.Related...I Idolised My High School Teacher. Then I Dated Him.A Guy I Once Dated Is Now Famous, And It's As Weird As You'd ImagineI Dated My Camp Boyfriend For 3 Summers. Years Later, His Sister Found Me — And We Fell In Love.

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