Ask Dr. Nerdlove by Harris O'Malley

How Do I Respectfully Approach Trans Women?

DEAR DR. NERDLOVE: I have re-written this letter a thousand times in my head and am still not sure it is one of the things that registers in the NerdLove realm, yet I feel you might be the only one who can help me with this… well, I hesitate to call it a problem as much as an unyielding curiosity.

Let me just begin by saying for my entire life I have dated in the hetero-realms. I got off to a slow start and hit a bullet train in the vis-a-vis dating world around late high school, with another acceleration happening in college. There are tons of stories there that I’d love to flesh out, but I’ll leave them for the sake of getting right to the point.

I am in a new city and am rediscovering myself as it pertains to finding friends, enjoying the hobbies I am into, etc. I hesitate to say it is going super well but it is going which I am perfectly happy with. My question is simple, and yet kind of touch and go and crazy and god knows what else: I have recently discovered that I have a very real desire to date and or sleep with trans women.

To be frank and clear, I am not attracted to dudes at all. That said, I am however finding that I could be VERY interested in being with a woman who… well, had a significant dude-part (as it were). Now, all of this is quite speculative. I have never been penetrated (pegging, etc whatever you want to call it) but I am very interested in the concept. I should also probably add that I have been single for quite some time and am by no means just swimming in dates that I could potentially attempt to vet with aggressively invasive questions a la “do you have a penis and, if no, do you own a strap on?”

My initial thought is that one would assert the sex positive aspect of this. While I don’t find this desire odd or weird at all, I am just not certain how to approach it. Where do you go or hangout to meet people? In what way do you express your lack of experience in combination with wanting to desperately give things a shot?

I must say that for all my social skills I am not sure how to approach this one. I have an easy enough time talking to women (though I do have to work on the whole “she is sending signals and you should get her number/ask her out” thing) but I feel like this is a multi-tiered dilemma. Any and all love of the nerd persuasion to this situation would be appreciated.


Seeking Something Different


Ok, SSD, this is an area where it’s best to proceed carefully, because it’s very easy to end up making someone feel dehumanized even when you’re trying to express genuine interest in them.

Let me start with the less-obvious point, StWP: being interested in trans women doesn’t make you gay or bi. Trans women are women, period. Similarly, being interested in butt-play, prostate stimulation or other forms of penetrative sex beyond penis-in-vagina, whether giving or receiving, has nothing to do with your sexual orientation; it just means you’re discovering that you’re a little less vanilla or conservative than you realized you were.

Hell, even just wanting to play around with gender roles or doesn’t mean that you’re not straight. It just means that you’re more flexible than other folks.

And hey, that’s awesome. No matter what the reason is for your newfound interest, let your freak flag fly high and proud and follow the best-practices as outlined by guides like Erika Men and Mathew Nolan’s “Oh Joy Sex Toy” or “The Ultimate Guide to Prostate Pleasure” by Charlie Glickman and Aislinn Emirzian.

Now, with that out of the way, let’s get to the part that makes me pause. It’s cool that you’re interested in trans women… but the way you’re framing your interest gets a little tricky. It sounds to me like you’re fetishizing and exoticisizing them, which ain’t cool. 

While there’re definitely trans women who’ll appreciate a man who’s into them because they’re trans – after all, people aren’t just people, we’re all also pieces of meat, and there are times when it’s nice to know that someone wants you specifically for what makes you unique – but there’s a fine like between digging someone for who they are as a person and being reduced to just one aspect of themselves. As long as everyone else involved is on the same page with what’s going on, that’s cool; blessings on you both. But you need to be mindful of the fact that what for you is a kink or a little exciting bit of spice, is someone else’s life.

The last thing most people want is to be a prop for somebody who fancies themselves experimentation with being edgy and transgressive. A trans woman being made to feel like they’re just “a chick with a d

k” who’s there to provide naughty thrills somebody looking for a walk on the wild side is feel incredibly dehumanize and that’s an awful thing to do to someone.

(Unless of course, that’s their particular kink or they’re a sex-worker providing a service. But I wouldn’t bet the rent on it.)

I’m not saying that you can’t or shouldn’t date or sleep with a woman who’s trans, but I am saying that you need to tread incredibly carefully. There’re a lot of potential minefields that you want to avoid, both for your sake and hers.

You’re also assuming that trans women are going to be interested in being the penetrator by default. That ain’t necessarily the case. If what you’re looking for is being pegged by a woman, specifically, you may have better luck looking for a cis woman who’s into bending guys over.

So that being said, your best bet for finding someone is going to be online. After all, you want something fairly specific, and this is one of the times when it’s better for the mountain to come to Mohammad instead of the other way around. If you’re looking for someone who’s packing a strap-on and an urge to use it, you want to go where the kinksters hang out. FetLife and other kink-friendly dating sites are an obvious place to find women who’ve got an interest in pegging. Create an account, get to know folks in your area and see if you can find someone who’s interested in topping a guy who’s curious about being pegged.

You can also browse around on OKCupid, looking for people who’ve answered specific questions or checking for particular keywords. It should be noted that it will take some digging and reading between the lines to find women who might be interested pegging a man; most women who indicate an interest non-standard sex tend to get deluged with so many creepy messages that they tend to fold up shop or go incognito. You may have to create a profile specific to your interests and wait for THEM to find YOU.

But you’re going to need to be very clear about what it is that you want and are looking for. If all you’re doing is looking for a specific experience, then you don’t want to be giving people the impression that you’re looking for a relationship. Giving people the option of opting in will be far better for you - and them - then using the veneer of dating to find the sexual experience you’re after.

You may be better off looking for people who’re willing to provide that exact experience, rather than casting about at random and hoping to find someone who’s either trans and/or into pegging and end up treating them less as a person and more as a means to fulfilling your fantasy.

Good luck.

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