Daddy Santos on getting what you want
We learn from NYC leather daddy and sex educator, Santos
"What's the point?"
Not the worst reaction I've gotten from a cis gay dude, but it's up there.
This wasn't because I'm trans by the way – this was to me saying I'm a top. Reactions like this don't make me angry or hurt so much as they feel tedious and also generate secondhand embarrassment: if your entire concept of sexuality is insert tab A into slot B how is that sex any different from masturbation?
There's a lot to unpack in the assumption that my being a top misses the point. Foremost, that the feature in fucking me lies in my having penetrable genitals, and that those bits should be on offer. The current zeitgeist seems to omit the possibility of me having a huge, sensitive, flesh and blood dick. Lots of trans men do. I don't happen to, but also nobody ever asks. The fact that I have my natal bits – and even that I enjoy getting fucked – does not mean my purpose is cis men's pleasure.
Working at a sex shop in New York's gay West Village gave me insight into the kinds of expectations gay culture tacks onto identity. Cis twinks and other cis men on the femme side came to the shop desperate to learn how to bottom. One of the first questions I'd always ask was "do you want to?" Some did, others bought trainer kits out of obligation, and a notable few didn't purchase a damn thing but left with much more than they came in with.
In my opinion, cis gay men largely opt out of monolithic male heteronormativity only to don pre-packaged gay masculinities (e.g. nelly, muscle bear, daddy, drag queen) and never bother challenging the expectations associated with, but not necessary to embody, each category. Meanwhile it seems to me that trans men are allowed to be one variety of gay product whose marketed look is androgynous, youthful twink and whose marketed use is the perfect bottom. It's often a revelation to cis gay men that a 40-year-old, hairy, masculine top in leather (essentially the canonical leather man) would be trans.
I was to plan a date – which consisted of three separate destinations – every Tuesday. If I was good I got to carry her purse, and if I was very good, I got to buy her a cocktail.
In a way, my being a leather man is as much performance of an off-the-rack gay masculinity as it is rebellion against cis expectations of how trans men look, act and fuck. Leather dom is where I feel most at home with myself. Let me tell you what I mean, in a more or less linear way…
I was molded by punk music, ethos and fashion, and very aware of its many connections to BDSM. I had already spent countless afternoons tucked into corners at Barnes and Noble, reading erotica by trans man and leather icon Pat Califia when at 19, I bought my first dirty magazine. It was a copy of On Our Backs featuring leather dykes – particularly a submissive crew cut butch in a leather Y harness whose description was my first ever interaction with the word "boi". Reading this word, especially in that context, was profound. Laid out on the page was an affirmation of masculinity and sexuality that finally felt close to my own.
During my early twenties I read as many books from Cleis or Greenery Press as I could find. I also did some provisional BDSM with my first partner back then. Our relationship was on and off for a bit, so during one of my single periods I gave my submission to a high femme domme.
Our dynamic was technically non-sexual though inundated with desire. I was to plan a date – which consisted of three separate destinations – every Tuesday. If I was good I got to carry her purse, and if I was very good, I got to buy her a cocktail. During one of our dates, she sat at a booth and sent me to the bar to bring her a martini saying "don't spill a drop". I still get flustered remembering the intense focus and thrill I felt while delivering that precarious drink: it serves as a reminder not to go too easy on my submissives.
I would go on to spend some years as a 24/7 submissive in a dynamic laden with murky consent. All the while I was mentally exploring and mosaicking fantasies that I hadn't yet realized were rooted in a deep desire to be a dominant leather man. The desire to express a hard-edged, boldly sexual masculinity felt to me at the time like a vague and jumbled envy. I was certainly kinky and devoted to the lifestyle – there were just some pieces missing.
It took lots of book-learning and hard knocks to get from that place of insecurity to more or less holding my own. Part of the process for me was, of course, untangling my understanding of my gender. I gained a real sense of who I was and what I wanted, as opposed to the nebulous sense of self I’d previously had that found solace in other people's desires regardless of whether they were healthy for me.
In time I tired of doms who were greedy as opposed to creative and perceptive. And as I got older, more boys came to me seeking Daddy. I found that my version of Daddy gets what he wants and makes sure the dynamic is as replenishing as it is interesting.
Working at a sex shop also helped me give myself permission to take up more space. I got a rare view of people's vulnerability around sexuality and realized that no matter how desirable we may be according to societal hierarchies, we're all insecure.
Knowing that we're all insecure has really helped with bar cruising. It's an equalizer. There's no way I can know what anyone thinks of themself, or why, but I can allow myself entitlement to sexual attention. I can know that I'm a catch, and that anyone rejecting me is either missing out or helping me dodge a bullet. This is more or less how I came to know confidence, and confidence feels like the defining piece in embodying the mosaic of fantasies I first imagined decades ago.
One of my favorite memories of self-assurance in bar cruising happened just before lockdown. I was riding high from a great date earlier that night and decided to take myself to The Eagle. It's an NYC leather bar, but no one was in gear except a silver haired muscle bear wearing just cowboy boots and a jockstrap. Clearly the hottest guy there. He did a slow lap around the bar, peacocking. Displaying. A while later, he did another lap, but this time he wore nipple suckers – here was the ask, the offer. I love tit play, so I walked right up to him, introduced myself, and within a few minutes I was feeding him poppers and absolutely torturing his tits. Eventually, we stopped because he didn't want to cum yet. That whole interaction happened because we both understood the importance of chance and connection in cruising.
I've gotten to a point where I know that I naturally have big needs. I need the novelty of unpredictability and risk that cruising provides. I prefer having a variety of partners as well as a primary, and I need that primary to love me as I love him: with loyalty and pride, and without the specific chemical cocktail of romantic love. I've found that in a few wonderful submissives, all of whom I'm still grateful to have known.
My current boy has desires congruent and complementary to mine. He's my bitch 24/7 and came to me looking to be trained, used and cherished. To put a finer point on it: before he met me he'd joked about his search for "someone to shave his head and tell him what to do" – and wouldn't you know it, I have a barbering fetish. He is gay and trans just as I am. We both have easily identifiable New York accents (though his is more Long Island) and he knows that "his" mouth is mine and its true purpose isn't speaking anyway, it's worshiping my dick.
Our dynamic works easily because he needs what I want to give and I need what he wants to give. Which brings us full circle to the question I opened this essay with.
“What’s the point?”
Getting what you truly want. That's the fucking point.
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Santos is a Latino, gay, trans, leather man, sex educator, visual artist, punk musician, & lifelong New Yorker.
Follow him on Instagram @mini_husky for updates on an upcoming podcast centering gay & queer trans men & adjacent folk.