Lust With Levi

Dear Levi B.,

I consider myself to be a queer man, but, for whatever reason, I’ve only ever dated straight women. I just got out of a long-term relationship, so I’m trying to put myself back on the market. Recently, I’ve been communicating with a woman online who I found through a Craigslist personal ad who identifies as queer. From some of the things she’s told me, I’m starting to think that she might be a trans woman. We haven’t met in person, yet, but I feel a little nervous and I’m wondering if I should bring it up with her.
Crushin’ and Questioning

Dear Crushin’ and Questioning,
Don’t be dismayed. It’s always a little intimidating to try something new and when it comes to matters of love and lust and identity, it can be utterly overwhelming. But I have some suggestions for you to help you feel more at ease.
First, for others reading this column let me define “trans woman.” A trans woman is a person assigned male at birth, who feels that the designation does not describe their internal gender identity and wish to identify as a woman instead, in order to live in a way that better reflects their understanding of themself. They might also use the terms: tranny girl, tranny grrl, transwoman, t girl, transsexual or some variation of these terms. Now to your question…
You met someone online. She seems nice, you have some things in common, things are going well. Do you ask her if she’s trans? I wouldn’t. In the event that she isn’t trans, she may be offended at the suggestion –though this would indicate her own transphobia, but, alas, it is a pervasive and often un-challenged –ism in our society. If she is trans, she will tell you when she thinks the time is right. She is as unsure of you as you are of her at this point, and coming out as trans can be a difficult and painful process. I’m sure it’s no shock to you that many people react in fear and disgust when they learn that a friend, partner, or family member is trans. She needs to know if you’re worth the risk. Let her get to know you. Arrange a coffee date or two so that she can get to know you better and discover for herself that you are a sensitive, trustworthy guy. If she is trans, she will tell you when she is ready. Let her. It isn’t yours to decide when and how that information is shared.
If she does come out to you as trans, take some time to search yourself for whether or not you are really interested in her and why. I’m sure it will seem new and unfamiliar, but remember that every person you date, regardless of their gender or body parts or hormones, is new and unfamiliar and unique. Even a non-trans woman has her own sexual preferences, body shape, genitalia variations, and physical responses. A trans woman, in that right, isn’t so different from a non-trans woman. Personally, I think you should go for it. There’s no good reason to write her off simply for being trans. That being said, nobody wants to be someone’s personal experiment. If you want to date her or have sex with her because you think it would be so cool to date a trans woman and then tell your friends about it later, or because you’re just really curious about what she looks like between the legs, you really need to re-examine your motives. As with anyone, you should date her because you feel a connection, because you like and respect her, because you’re attracted to her.
If you get to this point, and you’ve decided to pursue some form of relationship –and I hope you do– you and she will probably start thinking about doin’ it. Intimidated? Don’t be. It all boils down to the same thing: communicate. Every trans woman –and everyone else, too– has different needs, desires, and boundaries in bed. Talk to her about what she likes. She may have certain body parts she doesn’t want touched or talked about, especially those that are “male” body parts, or she might celebrate those parts of her body and want them to be touched more than others. Or she might not really care one way or the other. Often trans people have special names for body parts they attribute to their assigned sex or their “former self.” Ask if she has any names she prefers for her body parts. She may also be on hormones and/or be post-op, meaning she underwent “sex reassignment surgery”. Be aware that her body might look and feel different than what you’re expecting.
On the subject of hormones and surgery: those are other topics that she will tell you about when she’s ready, so as tempting as it is, don’t ask.
To summarize: be yourself and let her learn to trust you, and communicate, communicate, communicate! Good luck!
Lusting for You,
Levi B.