Crossdress Mixtape

Here’s a playlist of transgender-themed songs that I enjoy.

The Magnetic Fields – Andrew in Drag (2012)

Good luck getting this one out of your head. Although the concept of drag is more about performance than anything on the transgender spectrum, I think it is still close enough to justify being on my list. The Magnetic Fields (who clearly own the world’s best rhyming dictionary) sing a happy-go-lucky pop tune about falling in love with your friend’s drag persona at first sight. While the song may appear lighthearted at first, I think anything that deals with the taboo of loving someone with nontraditional gender roles is in fact a quite serious one. It takes courage to discuss anything related to that nature, and while the song may be fictional, the idea certainly comes from somewhere and that should be respected. And like I said, it’s catchy as hell.

The Replacements – Androgynous (1991)

I have to admit, I’m not very familiar with The Replacements. When I first heard this song on the radio, it immediately jumped out at me. The opening lyrics are, “Here come Dick, he’s wearing a skirt / Here comes Jane, y’know she’s sporting a chain.” I love them because of how many different levels they work on. Obviously, you have the vaguely socially acceptable, pushing gender boundaries of the crosdressed pair, but what really stands out are there names. Not only are they wearing the wrong sexes clothing, but they’re the Dick and Jane from the very traditional children’s book series. There’s also the fact that the boy wearing the skirt is named Dick, but that’s just middle-school-me laughing at the sexual implication of the name. Tee hee.

The end of the song sends some mixed messages. “Tomorrow who’s gonna fuss?” sounds great in theory. Hooray! Social progress! Crossdressing, however minimum, is accepted! But then we hear that tomorrow Dick is back to wearing pants, and Jane, a dress. Where’s the change in that? I understand that the tone of the song has more to do with rebellious trends than it does crossdressing, but still – my crossdressing isn’t a trend. I guess I should write my own song.

David Bowie – Queen Bitch (1971)

There are a whole slew of genderqueer songs to choose from with David Bowie, but if I had to choose my favorite, Queen Bitch takes the crown. Yes, it’s true, the song is about Bowie’s friend being picked up by a crossdressing prostitute, a story I cannot relate to. I can’t help but ignore, though, the repeated phrase, “I can do better than that.” Bowie is tapping into something I’ve discussed in earlier posts, which is the competitive nature of crossdressing. The sport of it. Whenever I see a crossdresser impress me (be it with make up, wig, clothing, body, etc.) I always think to myself (in this order): A) How did she do it? and B) How can I do it better.

Admittedly, I’m almost never able to do it, and even fewer times can I do it better. Regardless, if you don’t try, you may also wind up like Bowie, who repeats later, “Why didn’t I say?” (That is, in reference to it not being he who goes home with his friend while en femme.)

Walk on the Wild Side – Lou Reed (1972)

Bowie’s “Queen Bitch” was supposedly a tribute to Lou Reed. A year later, Reed released the classic song “Walk on the Wild Side.” The song follows the travels of a number of crossdressers, who are all “followers” of Andy Warhol.  The song is mostly a series of  vignettes, with little in terms of relevance to my experience crossdressing. Even without my deep thoughts, though, it’s place in the pantheon of transgender songs is undeniable and I expect it will outlast all other songs on this list in terms of popularity and radio play.

James – Laid (1993)

This is one of those songs that everyone is familiar with, but most don’t have a clue what it’s about.  While not totally clear, the lead singer is clearly singing about a relationship that involves some sort of nontraditional gender roles. Specifically in the lines, “Dressed me up in womens’ clothes / Messed around with gender roles /Line my eyes and call me pretty.” The singer seems to have mixed feelings about the relationship. For one, he’s seeing a therapist. The relationship continues, however, and when it appears he’s being stalked by his lover, he eventually succumbs. I have to wonder, though, is it Stockholm syndrome, or just someone accepting who they love?

Garbage – Cherry Lips (2001)

I’ll be honest. I’ve heard this song a million times, and didn’t realize it was about a crossdresser until I looked it up. Apparently, Cherry Lips was the name taken by a boy in the book Sarah by J.T. LeRoy. The boy’s mother is a truck-stop prostitute, and when she ignores him, he begins to wear her clothes and take on her role. I haven’t read the book, but probably will at some point.

The Kinks – Lola (1970)

Who didn’t see this one coming? A classic in it’s own right, Lola is probably one of the first songs you think of when you think of crossdressing songs. Which is probably all the time, if you’re like me. My favorite line in the song is, “Girls will be boys and boys will be girls / It’s a mixed up muddled up shook up world except for Lola.” I love the idea of the world being crazy, and transgendered people are the only one who have things straight. Can anyone really be 100% male or female in terms of their interests and the expectations set upon them by society? Lola accepts the world as it is, and is therefore enjoys being male and female, which is more than most people can say.

Matt Nathanson – Kinks Shirt (2013)

Thirty-three years after the release of Lola, here’s a song that references it that isn’t by Weird Al. And what a tribute it is. A modern day Ray Davies, Matt Nathanson has fallen in love with a crossdresser, and if you watch the music video, just goes for it. No question asked. I love the picture he paints in the lyrics of all of the things about the crossdresser than stand out as memorable to him. Her silhouette, red painted fingernails, party dress, the way she walks, talks and of course, her Kinks shirt. It’s these images, these microscopic moments of femininity, that stand out to him, but are also the ones that stand out to me. The only difference is how we respond to them. He’s attracted to them, beauty being genderless, while I try to emulate them.

The song itself is also catchy, and the music video manages to be funny, without mocking the topic.

If you have any other songs you think I should listen to, or add to the list, feel free to post in the comments. And please, no Aerosmith.

Casual Updates

So much tell everyone regarding the weeks following my transformation session, but it’s late, so I’m going to be quick.

Halloween – I was Little Red Riding Hood, while my fiancee was the Big Bad Wolf. Totally rocked it, and told a number of people (quite clearly) about the role crossdressing plays in my life. Felt good.

Casual – I’ve been doing a lot more casual/hidden-in-plain-sight dressing lately. Leggings beneath jeans, underwear, painted toe nails. It’s easy to do, and makes me happy.

New Wig – I couldn’t get over how much I liked the long-hair pictures from the transformation session, so I bought my own long hair wig. It arrived this week, but I didn’t get a chance to try it on until today. It’s a little bit browner than I thought I was getting, but after playing around with it, and wearing half the day, I think I have it under control. Here’s a pic of the wig, front and back.


front and back

Overall, I think the short wigs do a better job of shaping my face, but there’s nothing like having long hair to play with and style. The brown hue is also growing on me.

In case anyone was curious, there are about 40 pictures from the transformation on flickr. At some point I will edit a few to make my postable here, but they’re worth creating a flickr account for, because his make-up job is fantastic. I can’t wait to go back.

I want to update a bit more frequently going forward, but easier said than done. Until next time!