I can’t say I know what it’s like to be a gay man. For one, I’m technically bisexual and queer. I’m attracted to the person and the gender, and I have had lovely relationships with men, women and non-binary folks. To me, this makes me hella gay: I’ve been a woman with women, a man with men, a gender-curious person figuring it all out with other gender explorers.
Also, I sing and wear rainbows. As a child, I loved theatre and performance. My grandmother used to ask me to perform in her living room. “Make all your faces for us,” she’d say. The world saw a petite five-year-old girl with long brown hair and expressive brown eyes. In retrospect, I could just as easily have been a flamboyant boy loving the dress and the attention.
What I loved about my time dating women as a woman—before I realized anything material about my own gender—was the amount of fun we had while figuring out what we liked. There was no expectation about how sex was “supposed” to work, or about who would do what at home. There was no prohibition on talking about your feelings or expressing love and affection for those you cared for. You could be warm and open and vulnerable and sweet and tender and have the hottest, most intense kink scene of your life—in one session.
It also helped that we knew how to enjoy every part of our bodies, how to ride waves of sensation for hours. We could come so many times we lost count, if we wanted—or we could forget about orgasms and spend a day tracing every curve, getting to know details we’d somehow discovered just then, even if we’d played many times before.
This is still my favourite kind of sex. It’s not about gender, really—it’s more a frame of mind.
How I came to realize I was actually a queer man, not a queer woman, is another story. After I came out as trans, my mom asked, “Are you still bisexual?” “Yes, mom,” I said. I am! I still swoon for butch dykes, still fall for bookish guys in glasses, still appreciate gender-bending in all its beauty.
This story, though, is about finding my footing in the abyss known as Grindr.
I had been on testosterone for about six months when a friend I’ll call Scott turned to me and said, “You need a Grindr”—the app gay guys use to find hookups. I looked at him in disbelief. “I’ve always dated and hooked up with people I’ve met in person,” I replied. “Besides, am I going to be the only trans guy on Grindr?”
Scott took my phone and started filling out my profile. A few minutes later, I was officially registered: I had a name, a photo, some sort of bio and a lot of “tribes”—like “Trans,” “Muscle,” and “Geek.” After Scott left my house, he tapped me—Grindr’s version of a “like”—and sent me a message: “Good luck out there, handsome!” I put down my phone and left Grindr alone.
A few days later, my husband, Raj, asked me, “How’s it going on Grindr?” I hadn’t really looked, so I pulled out my phone and checked. I found a sea of isolated body parts: Headless torsos in profile pictures. Messages containing dick pics or ass pics, but not both. And, usually, no words. (Sometimes, one little word would come through. “Sup?”) Mostly though, it was dicks and asses. One profile read, “It’s 2019. No pic of your hole, no chat.” Really? I’ve never wanted to see someone’s hole before meeting them.
“I’ve never wanted to see someone’s hole before meeting them.”
So I didn’t know how to cope with the expectation of sending dick and ass pics when I don’t have a standard flesh dick and I’m not particularly interested in anyone else fucking me in the ass. I do, however, have lots of silicone dicks; I actually like that they’re in various shapes and sizes, and my partners can choose the ones they like. Also, I’m thankful that I don’t have a refractory period and that I’m always hard. One hilarious bit of transitioning was when Facebook realized I was a dude: I started getting ads for Viagra. I laughed, and thought, “Thanks for the correct gendering. And also, I will never have that problem.” I wasn’t going to send pictures of a dick I didn’t have, I didn’t want to send pictures of my actual crotch and I didn’t want to send pictures of my ass. Basically, old-fashioned though I may be, I much prefer sending pictures of my face. The face is the most expressive part of our bodies, and watching people’s faces during sex is half the fun.
One day I walked into my bedroom after work and was surprised to find a music stand with my three dicks on top, arranged from small to large. I wondered what happened, since I hadn’t put them there. Turns out Raj had surprised me by taking dick pics for me. He said, “Look! I thought you should have dick pics for Grindr. So I arranged a photo shoot.” I burst out laughing, and thanked the universe for having such a fantastic husband.
It still took me a while to have my first hookup on Grindr. I got a message from a blond guy in glasses asking how my day was going. “I’m exhausted from a long day at work,” I said. “Well, I could come over and service you,” he said. My eyes lit up. I hadn’t thought of that! So we negotiated activities and safer sex precautions. I checked in with Scott on safety. “Is this really a thing that people do?” He reassured me that yes, inviting strangers over to your house to fuck is definitely a thing that gay men do. I checked in with Raj on safety: He preferred having a stranger at our place rather than me going off into the unknown. Raj settled into the guest bedroom, expecting this to take awhile, since I typically play for hours.
So the dude showed up. He looked like his picture, hooray! And he was familiar with my anatomy. He went down on me beautifully, and I came a few times. Afterwards, he said, “I feel better. Do you feel better?” Yes, I did. And then he left. It was simple and kind and exactly what I needed at the end of a long day.
I went into the guest bedroom and snuggled Raj. He looked at me and asked, “What happened? That was only, like, fifteen minutes.” Truth: It was really short. But honestly, that’s all I had the capacity for that day. I was tired and it was a sweet release. Then Raj and I, feminist nerds that we are, spent the next two hours processing this experience: He couldn’t imagine this happening in the straight world, mostly because of the patriarchy and all the attendant safety concerns. But also because there’s so much more of a dance around desires and expectations and flirtations—it’s just not normal to be that direct and also kind.
I wish I could say all my experiences were that great. They weren’t. Some guys thought I was a girl: “Sorry, I’m into men, so I’m not into you,” or, “Oh man, I’ve been looking to hook up with a girl for awhile.” Some guys fetishized trans people, and would write “TS or CD only” on their profiles, saying they’re looking only for transsexuals and cross-dressers. One of the worst offenders was the guy who had “whites only” on his profile, then continued creating new accounts and messaging me after I blocked him, asking, “What? You’re white, why is this so bad?” Ugh. I couldn’t believe I even had to explain that.
“I wish I could say all my experiences were that great. They weren’t.”
I try to focus on the fantastic experiences instead. In small town New Zealand, right after someone rejected me for not being born with a dick, a gorgeous man sucked my testosterone-grown cock for 40 minutes. Cosmic justice! On my way to the airport in Denver, I stopped by the apartment of a 6 foot 3 inch-tall jock and fisted him before my flight. At home in San Francisco, a bi guy came over and had trouble getting it up, so I asked him to fuck me with his hand the way he would with his dick. I came a few times, and he said, “That was amazing.” I replied: “Look, dude, we can use our whole bodies. Your dick is optional.”
One of my favourites, though, was flipping a leather daddy in the Castro. He was in his mid-40s and swore that he never subbed for younger guys. I’m switchy by nature—meaning I enjoy both dominant and submissive roles in BDSM scenes—so I raised an eyebrow, made a mental note and negotiated our first scene with me as the sub. The second time we played, while we were making out, he paused, looked at me all confused and asked, “I… think I want you to flog me?” Hell yes, I could do that. So I strung him up in his doorway. As I flogged him, he said, “Oh, you’re good at that, boy.” Eventually I untied him and moved him to his couch, while keeping him under me. Some slaps and caresses and careful positioning later, he’d shifted from calling me boy to calling me daddy. My switchy self beamed. I was gay man enough.
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