View From The Top: A Short History of What I Learned From Dating

F., my first girlfriend. We take turns wearing the strap-on. We are both slowly coming into a more and more masculine identity, but we don’t really talk about gender. We take turns being on top. (At least, that’s how it feels to me — I wait my turn to top, and tolerate being on the bottom.) I am thrilled to explore everything, eager and game for whatever she wants, curious and vocal about things I want to try. I don’t remember whose idea it was to fist, but I remember the feeling of being filled that deep for the first time, and how her eyes sparkled with awe. That, I thought. I want more of that. From our relationship, I learned to seek someone with devotion in their gaze. I learned that I wanted to be in charge most, if not all, of the time.

D., my first girl love. I started understanding what radical femininity and femme identity were through being D.’s best friend, and quickly fell for her. We flirted and hugged and kissed during spin the bottle and, once, slept in the same bed. I still remember the smell of her shampoo and how her skin would flush red in the heat of summer. I followed her around like a baby duck. And I played my whole hand early. She knew she could have me whenever she wanted me. I could not get enough of the friction between us, my budding butch gender and her fierce strength. Our relationship solidified my desire for someone who identified as a femme bottom, and made me even more confident to call myself a butch top.

M., my college girlfriend. I thought she was exactly that: a femme bottom to my butch top. I thought she wanted to play with the things I wanted to play with: bondage, flogging, ice, wax — the sensation play of safe BDSM, done for exploration. She was so into it. She talked a big game. She wanted to try everything, but shied away from it all. We stopped having sex after only two years, but stayed together for two more. She talked a lot about transitioning. Her fantasies were about gay men. I thought I’d chosen well, but I had apparently misread her. I was still seeking a femme bottom, I was still aching to manifest the butch top that I knew was in me.

C., my quick fling. We went deep fast, and we all know how that ends: in explosion. But still, it was the best sex of my life, and I finally got to be the butch top alongside a femme bottom. It was all I wanted, and more. Yes, I thought. This is what I want. It was so hard to let go of it, because it was what I thought I wanted and had sought for so long — but there were so many other ways we weren’t compatible. I learned to trust the red flags. I learned to listen to my friends. I learned to identify as stone, as a shorthand for top, because not everyone identified as a bottom, but they understood what they would get with a stone butch.

R., my playful equal. Another sex educator. High femme and well-equipped, whip-smart and knew exactly what she wanted. Unafraid to talk. Unafraid to ask for more. Eager and willing to dive deep into my body, and into hers. She and I studied at the same sangha, shared the same philosophies. But she wanted to switch, more than I did. And she didn’t want as much strap-on play as I did. I learned that I would most prefer to strap on nine times out of ten, and I rarely wanted to be touched. I learned that I wasn’t just a service top — though I loved focusing on the pleasure of my partner, I wanted more. I wanted to practice being in charge even deeper.

T., my best friend and big crush. I tried to keep my boundaries strong when she was dating others, when I was dating others, when neither of us were single, but we were clearly drawn to each other. Our friendship was a romance and we courted as much as anyone. Brunches, wine, take-out and late-night chats until I had to call a car to get home because the subways were no longer running. Desire and desire and desire. I thought we would eventually have a go of it, if I stuck around. We never did. I learned not to get too romantically involved in friendships, as it’s so hard to de-escalate to a softer friendship, so they often result in a more serious friend breakup. I learned I wanted not just a femme bottom, but a femme submissive — a femme girl to my butch Daddy. I learned that there were some femmes who were as focused on receiving strap-on sex as I was focused on giving it.

S., my girl. Until S, I wasn’t a dominant, I was a top. With S, I became a dominant, and truly practiced being a daddy. On our first date I told her I was stone, but we slowly unravelled that and complicated it until we understood that I could tell her how to touch me and it was still part of her submission. I gave her a collar. I thought we were building toward forever. I wanted everything with her. I thought we were on a “power escalator,” slowly building trust and moving toward a total power exchange, where she was given over to me completely. And while she went along on the ride for quite a while, it wasn’t right for her. It didn’t occur to me that we would stop deepening the power dynamic. From our relationship, I learned how far I wanted to go — not just bedroom play, not just life rules, but completely. I craved the kind of authority that would extend to every piece of my partner’s life.

N., my fireball vixen. A tiny fling with a deep friendship. Wine and late-night conversations and she slid the word “daddy” into our play like it had always been there, and I wept at the recognition. Even if I wasn’t her daddy, I was a daddy, it was that deep in me. I learned that my lust lives deep, and that I could still court, be courted, flirt, be seduced. I learned that casual short play is still possible, though it isn’t nearly as satisfying as the fully upturned offering of a long-term submissive.

r., the boy I’m going to marry, to keep, to cherish for as long as we possibly can. I wish someone had told me sooner that I had been seeking mastery all this time, but I wouldn’t have been ready to hear it. Until r came along. Until we discovered it for ourselves, from the ground up. We read books and books and books together, trying to discover these urges that had always been in us but never before had a name. From our relationship, I’ve learned that I sometimes go off into my own world and don’t take him with me, even though the only thing he wants to do is come. From our relationship, I’ve learned that there is a gap between what I want to control and what I can control. From our relationship, I’ve learned that I still need to internalize and improve my ability to stay in the present and not live in the past. I’ve learned that I hold on to hurts, I attach to events and people and places, I have a very hard time letting go. I’ve learned that once I have a plan, breaking from that plan tends to make me very grumpy. I’ve learned so much about myself, while at the same time learning so much about him.

Each person I’ve been privileged to be with, each person who has let me deep into their intimate inner world, I’ve learned from. I’ve learned more about who I am, and figured out more each time what kind of partner I’m looking for. Sometimes that was about communication, sometimes emotional compatibility, sometimes gender and power. All of those learnings combined led me to rife. I never really would have known he is what I was looking for, but when I saw him, I knew. I get to be my best self with him, and he keeps encouraging me to be even better, even truer, even brighter.

* All details are slightly fudged and combined to create more anonymity.

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Sinclair Sexsmith

Sinclair Sexsmith (they/them) is “the best-known butch erotica writer whose kinky, groundbreaking stories have turned on countless queer women” (AfterEllen), who “is in all the books, wins all the awards, speaks at all the panels and readings, knows all the stuff, and writes for all the places” (Autostraddle). ​Their short story collection, Sweet & Rough: Queer Kink Erotica, was a 2016 finalist for the Lambda Literary Award. Sinclair identifies as a white non-binary butch dominant, a survivor and an introvert. Follow their writings at Sugarbutch Chronicles.

Sinclair has written 43 articles for us.


  1. as someone who has been reading your work through so many of these relationships but also just as a person who can read, i really loved this

  2. Beautifully and respectfully written.

    it’s amazing to condense, what, 20 years of dating history and lessons and look at our relationship trajectories this way, from a zoomed-out perspective time offers. Makes me want to do one, too. :)

  3. I’m just starting on this journey and feeling like I’m supposed to know myself and desires before seeking a partner, so it is really liberating to be reminded that it is a journey and I will continually be surprising myself. And that is OK.

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