The Only True Top I've Been with Was Trans

There’s no more inane question to me than one of the most frequently uttered in the gay community than, "Are you a top or a bottom?"

I literally can’t tell you the intense negative visceral reaction that it causes.

Technically I am top.

And by that I mean I have never been fucked in the ass.

This is not to say the notion hasn’t occurred to me. I think early on in dating life, my “top” status was driven mostly by my intense phobia of acquiring HIV more than anything.

Also putting things in your butt hurts the first few times for the most part.

My first boyfriend and I dated, on and off, for over eight years.

In that time we consummated (i.e. fucked) maybe a handful of times. People give me weird looks when I tell them that, and I guess for a lot of people for whom fucking is the end and all and be all (or at least a good 90 percent) of sex, that makes sense.

Ryan and I were best friends first and foremost, and we’re both truly versatile in all senses of the word — I think. A lot of our sexual experiences revolved around our adolescent- or college-aged fantasies (we both had played NCAA sports in college) and was definitely more mental than anything else. Our intense friendship which begat the relationship, and physical similarities, added to an intense attraction and love that stays with me to this day.

That’s to say, our sex life involved a lot of dirty talk, foreplay, porn, and jockstraps.

And ecstasy.

It was the '90s after all.

Also if ever there was a time I was going to bottom, it would have been with him.

But alas, unlike Goldie Locks, we couldn't find "just right" and he proved too big for what I was comfortable with.

My next two relationships I was the top in, and involved more fucking, but also led to what I thought was a funny sort of role play in my own life.

I often wore my hat backwards, I was athletic, I was outwardly “straight” acting. I was also very loudly out, but I found myself often playing a version of me that wasn’t an act per se, just a certain combination of actual elements of myself that interacted with the person I was talking to’s perception of me seamlessly.

I remember once going to the Lure, which was a legendary leather club in New York City’s meatpacking district. Every Wednesday, they had an “open” night called ‘Pork’ that allowed the non-diehard leather, Chelsea, and East Village gay boys to dip their toe in the fetish laden bar.

My memories of nights at the Lure are highly titillating, yet at the time, they required copious amount of beer drinking to get to the point I felt even vaguely comfortable talking to, let alone participating in anything with, some of the guys. But one interaction has always indelibly remained in my mind.

This hot guy wearing a leather harness and other superhot accoutrements came up to me, a self-identified “top,” when I was just buzzed enough to make eye contact, and not knowing the proper etiquette of my surroundings, I simply nodded “S’up” (wearing a backwards baseball cap, navy blue Del the Funky Homosapien hoodie, baggy jeans, and Adidas) to which he replied “Get over here boy and get on your knees.”

The hood rat in me came alive and replied, “What did you say mother***er?”

At which point this super stud retreated into a nelly queen, and apologized profusely.

And I suddenly realized that the leather and all the posturing at this bar was exactly like drag. That is to say: an act.

And I’ve met drag queens that are more convincing tops.

A few years later I would meet a guy named Jon who changed my life in remarkable ways.

We’d seen each other out a number of times and after a few months, while hanging out at a bar with some mutual friends, I finally was like, “Hey, we should hang out sometime.”

We were sitting at a table across from each other and he said, “I didn’t think you were into guys like me.”

I was slightly baffled, confused if I’d heard him correctly.

“What the hell does that mean?”

He replied, “I’m trans.”

Later we would have a conversation about how alhtough we’d chatted on Grindr a number of times in addition to seeing each other around, I’d never actually read his profile (who does?).

So we had a funny exchange that resulted in an ill-fated but adventurous relationship, and definitely one of the hottest I’ve ever had.

Since then I’ve dated a few trans guys — I feel like this important to mention for a few reasons.

One is to dispel the ridiculous (and I mean ridiculous) comments and reactions that I’ve had from both my straight and gay friends.

From straight friends, after an explanation of what an FTM (Female to Male) guy is, it was fist bumps and “I always knew you were straight bro.”

No! I screamed in my head.

From gay friends it was a myriad of stupidity that makes me question everything about gay culture: “So do you f*** him in the ass?” or the inevitable, “Wait, he has a pussy? Ewww.”

It was a very isolating experience.

There’s a tremendous amount of transference and extraordinary empathy that can be overwhelming for an individual like me, who hewed closely, and was comfortable with a basic gender binary while engaging in this relationship. Again, some of this came down to some kind of psychological adherence to “normal” when you seek to justify your own existence as a queer person.

Yet the flipside was when we were alone, I thought of none of these things.

We were just two dudes crazy about each other. And in fact, our physiological differences added to the excitement. 

Indeed the very fact that I realized I could surprise myself sexually in my late 30s created a buoyancy in my attitude about getting older in general. 

It was during this period that I realized Jon was the top that wasn’t faking it. At all. He was exactly who he was and conveyed that in a number of ways that didn’t necessarily involve physical penetration, but he had the ability to dominate my mind.

And that’s what topping is really about.

My friend Cole who’s also trans gay guy — and a top — talk about this a lot. We definitely vibe on a level I don’t currently have with any of my cis gay friends.

As a matter of fact, in the small circle of cis and trans gay guys that we’re friends with, it’s the type of discussion that comes up fairly often.

There’s a camaraderie and brotherhood that we feel that I’ve never felt as strongly with other cis-gay guys who are supposed to be the conventional path.

The top/bottom question is closely tied with dick size, and is something that also rubs me the wrong way in being used as a barometer of whether the sex is going to be good or not.

So it upsets me when Cole offers up observations like this: “As a gay trans dude, I know there are gay men out there that wouldn’t like my body as it stands. A part of me struggles with that because it isn’t my fault. I understand preferences but it feels so strange to be reduced to a single body part. The idea that my body is incomplete because I don’t have a penis is baffling. I guess I kinda forget that I’m not just a regular dude until someone reminds me of how different I am. I forget that some gay men find trans bodies disgusting. It’s really sad actually because I only see beauty. Trans bodies are works of art. They’re a struggle through constant change and self-discovery.”

Cole might not have a penis but he’s “kinda happy about it because through this experience I’ve met some of the strongest, bravest, and most vulnerable people I know.”

Cole thinks we have to recognize just how phallocentric the gay world has been, and many men who ID as gay (or bi) struggle with their own issues around their penis (size, look, behavior).

Often their own issues are projected onto trans men who are pre- or non-operative, but it's more part of a bigger issue that affects men in general.

And Cole is honestly the truest top I’ve ever known.

Featured above: Trans actor Luke Hudson