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 the Whole ‘Package’
Let me start with the less-obvious point, StWP: being interested in trans women doesn’t make you gay. Trans women are women. Similarly, being interested in butt-play, whether giving or receiving, has nothing to do with your sexual orientation; it just means you’re discovering that you’re kinkier than you realized you were. Hell, even just wanting to play around with gender roles doesn’t mean that you’re not straight. Trans porn that features women with penises isn’t being filmed for gay men; some straight dudes are fascinated by cock but not by men.
And hey, that’s awesome. No matter what the reason for your newfound interest, let your freak flag fly high and proud and follow the best-practices as outlined by the anal safety snails.
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 it gets a little tricky. It sounds to me like you’re fetishizing and exoticisizing them. While there’re definitely trans women who’ll appreciate a man who’s into them because they’re trans – after all, we’re not just people, we’re also pieces of meat – 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. Being made to feel like they’re just “a chick with a dick” who’s there to thrill somebody looking for a walk on the wild side is going to be incredibly dehumanizing to them and that’s a shitty thing to do to someone.
(Unless of course, that’s their particular kink. 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.
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. You can also browse around on OKCupid, looking for people who’ve answered specific questions or checking for particular keywords. although 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.
Your other option, if you’re looking for a specific experience, rather than looking to find a partner (trans or cis) who’s kinky, is to hire a sex-worker. Do your due diligence first; there’re review sites that cover sex work and escorts, which will help you find someone who specializes in the activities you want, as well as give you a reasonable idea of what you’ll be paying. This helps ensure that not only will you be getting exactly what you’re looking for, but making sure that everyone involved is cool with what you want.
I have an odd question, Doc.
You see, I recently went on a very awkward date…or rather I went out for coffee with an acquaintance from a place I frequent and found out most of the way through the hangout that this was a date (full of all the maddening plausible deniability queer female/female pairings sometimes entail). The conversations went well generally and we’re into a lot of the same things. The thing that made this excruciating was mostly how frequently she’d beat herself up out loud over mistakes that were so tiny that I not only didn’t notice them, but right now I still couldn’t tell you what any of them were. To me this seemed desperate at best and pressure-y at worst and in either case it seemed ridiculously unnecessary considering what she’s got going for her. She’s attractive. She’s super-smart. She does tons of awesome things like martial arts and fire-dancing. There’s really no reason why she should expect to have such a hard time finding somebody.
So, the prospect of a relationship with me is dead in the water anyway because I actually DON’T want to date anyone who is into all the same things I’m into (besides, I was totally under the impression that this was gonna be Friends Coffee not Date Coffee). We kinda left things hanging after that date and I totally could just fade back out from here. I do however, think we’d make pretty good friends when and if the crush thing fades. I also know that in a lot of your posts you touch on the fact that nobody, especially not somebody who is turning you down right now, is obligated to teach people how not to be creepy and awkward.
But what if I kinda want to? Minus the benign incompatibilities, I think this should have gone way better than it did for reasons I can (and just did) point out. If I were to somehow explain this to her, I’m thinking it would be just a one-shot statement not a drawn out series of lessons and would also contain ample disclaimers about how my advice is not for her to learn how to try to pick ME up because no and because stated reasons. But that aside, what I’m seeing is someone who’s a really cool and awesome person who might not be aware of how much she’s shooting herself in the foot with the self-deprecation and unreasonable lack of confidence. Is there any reason why putting that out there to her might be a bad idea?
Ok, I see where you’re coming from TM and I totally get that you have a good heart and just want to help your new acquaintance. But unless she’s asking you for help, this has the potential to be very, very awkward for everybody involved, and more than a little painful for her.
I mean, imagine if someone you were interested in decided to tell you that she’d noticed some thing about you that you’re incredibly insecure about and while she may not be interested in dating you (Lord no!), she’d be willing to offer you some pointers about that thing you’re insecure about. Bad enough that sempai noticed this thing about you that you’re already self-conscious about but she’s letting you know that she noticed and thinks it’s something you need to work on.
Shit, that’s like a year’s worth of nightmare fuel right there, especially for someone who’s a little (or a lot) socially awkward.
If you want to give her some advice, that’s cool… but let her come to you with questions, instead of telling her everything she did wrong. If you absolutely need to be proactive, then maybe you can just float the offer – phrasing it as “hey, I’d rather be friends, but I’ve been in the dating game a while if you have any questions…”
Or you could always just set up a blog and hang out your dating advice shingle.
Hey, it worked for me!
Me and my girl have been together for about 7 months now. Though I am unwilling to sound the wedding bells, I do feel this is working better than any relation I’ve been in previously. But what I want to ask is this. She often feels depressed and stressed. She doesn’t apreciate if I approach her problems practically, but offering a shoulder and saying I feel for her and understand feels like it’s enough. Any advice on the matter?
You’re running into a man/woman socialization issue, CW. Men are socialized to be doers; we grow up taught that when we see a problem or a conflict, the best way to handle it is to solve it, no matter what it is. This can be handy, but it’s a pain in the ass when it comes to interpersonal relationships because not everyone is looking for an answer. More often than not, women aren’t looking for someone to solve their problems, they’re just looking for someone to vent to and want some emotional support. While it’s totally understandable that you want to do something – this person you care about is in distress! – providing a shoulder and a sympathetic ear is doing something, and it’s frequently more appreciated than a list of solutions they likely have already considered.
When in doubt, however, just ask: “Hey, would you prefer a shoulder or would you like me to brainstorm this with you?”