*I should preface this article by saying that I am speaking here about trans men who vary anatomically from natal males.*

When I first made the decision to transition many years ago, I honestly believed that I would never date, or be in a relationship again. For me this was a sacrifice I needed to make, and was prepared to live with, but was very pleasantly surprised when this turned out not to be the case at all.

My personal experience has been that, despite what many men think, women tend to care more about what’s in your mind and heart, than what’s in your pants.

Sure, we might be at an anatomical disadvantage when it comes to casual sex, but I’d say we’re actually at an experiential, emotional and psychological advantage when it comes to satisfying sex and navigating intimate relationships. Our “predicament” forces us to communicate very openly and honestly, very early on about our vulnerabilities, and allowing ourselves to be vulnerable, is what fosters true connection and trust. Brene Brown has a lot to say about this. If you haven’t heard of her, definitely check her out.

I can speak here only of my experiences over the years of dating straight women, and hope that I can give others insight/hope/understanding with just a few pointers.

Dating sites:

Yes, I’ve used dating sites. My favourite has always been OkCupid. I like it because it allows for very specific filtering, gives a percentage match and allows for more nuanced identities and orientations than any other site. Having said that, I do not take advantage of these nuances in my own profile. I list myself as boring old “heterosexual male” although you can choose trans if you wish. The reason I do this is primarily that I personally, do not identify as trans. Yes, it IS my physical reality, but I have always thought of myself as a heterosexual male whose body, historically, just begged to differ and whose body is now pretty well aligned with what I’ve always known myself to be.

Then at what point do I tell someone I’m trans?

What’s the point in telling someone if it’s not going to get past a first date anyway. Generally I’ll subtly weave a trans topic into conversation to establish their feelings on the subject. Assuming they pass that litmus test, and if after a few dates, there is a clear mutual attraction, it’s then a case of working out that sweet spot of the best time to say something. My experience has been that once someone likes you, then being trans is more often than not, not a deal breaker, though sometimes, it just is.

And yes, I will make out with someone before telling her, as that tells both of us a lot about what kind of physical/sexual chemistry we have. It’s usually only when I think we’re actually getting close to sleeping with each other, that I think it’s time to tell. The first time I had to do this, I was completely terrified, but over time, I’ve gotten a lot more casual about this, which I do think helps quite a lot in terms of how it’s received. I pretty much always say exactly the same thing, which is that “I wasn’t, physically speaking, born male.” This statement usually results in rapid blinking and a very confused look on their part as they’re trying to put the pieces together. The usual responses are “What does that mean?”, “So, you were born female?” or just plain old “Okay……….”

In any case, they never see it coming, so it does take a lot of gentle navigating from that point on to elaborate. I need to always remind myself that I’ve done this before, but at least in my experiences, it’s always been their first time, and I have to hand it to them, I have had some really awesome responses. The first girl I ever told, once I’d elaborated on what that meant in terms of my downstairs configuration, responded with “well… penises can be quite aggressive and stabby…” Another girl said “sometimes you get given a gift you didn’t know you wanted until being presented with it.”

My experience has been that most heterosexual women simply don’t know how they feel about the idea of dating a trans man. It seems to be more of an experiential thing, than an intellectual thing. Yes, some women have given the “I’m really sorry, you’re a really nice guy but…” response, and I always have to be prepared for that, but most of the time, there’s already enough of a connection there, that they are open to exploring further and in most instances, once we do become sexual, they realise that there’s far more pros than cons to being with a trans man.

So what are the pros and cons?

Well, let’s start with the cons. Really there’s just the one, and it’s entirely contentious as to whether that even is a con. I do not have a biological penis. The end. (Admittedly for some women, the fact that they will not be able to have biological children with a trans man is a big deal, but for myself personally, as I don’t want biological kids, this is a moot point.)

Pros: I have a better understanding of the female body than any of their past partners.

I understand that sex is far more satisfying and fulfilling when you’re not just focused on genitals.

Though, having said that, my penis self lubricates AND vibrates! (see the Joystick) For me personally, this is hugely important as I do want mutually satisfying penetrative sex to be part of my sexual relationships. For me, there’s something incredibly intimate about being able to move together in that way and orgasming with my partner. It has also been hugely encouraging to know that some women, who have not been able to orgasm during penetrative sex with their natal partners, have orgasmed with the Joystick.

I won’t make a mess of the sheets. (Though again, I guess it’s contentious as to whether that’s a pro or a con.)

No chance of unwanted pregnancies.

And even if I don’t really know what it’s like to BE a woman. I do know what it’s like to be treated as a women by society and to be in a woman’s body. This gives me social, physical, emotional and psychological insights that no natal male can possibly have.

So I guess in a nut shell, I would just love to have been able to say to my previous self “don’t worry, people WILL love you for who you really are. Be brave enough to be authentically you, be kind and caring, open and loving, and all else will follow.”

PS. I’ve since written a follow up blog post “A trans man’s guide to dating straight women (part 2)”.