Up until just now, I was not aware of any of my real life friends being into crossdressing.
One of my high school friends, let's call him "Tim" posted a YouTube video in 2009 where he and his friends danced to an anime theme song. Tim was wearing a dress (in the style of anime cosplay, but still a dress). I thought nothing of it when I first saw it in 2009 though, since plenty of people "crossplay" for anime-related stuff, and Tim was really into watching anime at the time.
Later on, I noticed that he started updating his Facebook picture with cutesy anime dolls, and then put a picture of himself wearing a pink wig and dress, again in the style of anime. But eventually his interest in anime started fading and he began embracing something new - the animated show My Little Pony: Friendship is Magic (usually abbreviated as MLP:FiM). For those who aren't aware, it is a show marketed for very young girls, but the high-quality animation style and positive messages have made the show attractive to many adults of both sexes, who refer to themselves as "bronies". Tim likes the show and identifies as a "brony", and posts a lot of MLP-related material on his Facebook, and even has a separate Facebook page for music remixes he made based off of the show's audio (and he has set his gender to female on this other page).
In 2011 he put up another crossdressing picture in a colorful dress where he holds an umbrella and carries some type of toy. Now this is going to make me sound like a total stalker, but I started looking at Tim's posts on brony forums and then just today, out of curiosity, I did a Google search for his main Internet handle and then "crossdressing" and I found some forum posts where he identifies as a "regular crossdresser" and also a post where he said his mom knows about the crossdressing, but it didn't surprise her because she knows he likes weird and girly things. He also made a post on a blog about how he strongly dislikes traditional gender roles.
So it looks like one of my real life friends is a crossdresser and is even somewhat out of the closet about it! Though I should say something about the way he dresses, because it's a bit different than how most girls on this forum dress. His outfits are feminine but mainly aimed to be cute and silly. He does the dress, stockings, pink and bright colors, etc, but he doesn't wear heels, skin-tight dresses, put on makeup or otherwise try to give his image a sexual allure. He also hasn't assigned a female persona or name to himself (he has the Facebook pony music page, but that's more a part of the brony fandom than a crossdressing thing). For him I don't think that his goal is to be able to pass as a woman, and I don't think there is a sexual aspect to it either; if there is he has been completely silent about it. I'd love to post pictures but I don't want to violate his privacy.
Anyway, I'm thrilled that one of my friends is a dresser. I don't talk to him that much, just occasionally on Skype because we both compose electronic music and I like sharing tracks with him. But I hope to at some point talk to him about the dressing. I'm not going to drop any hints that I Google-stalked him, of course, I'll probably just start a conversation about MLP:FiM (since I've watched a few episode myself), then lead the conversation to a talk about "girly things" and gender roles and then perhaps casually mention crossdressing and see if he says anything about it. He's a cool guy, eccentric in the way that I myself am, and is one of the few people I know in real life with whom I'd feel 100% comfortable talking to about my own dressing habits.
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Originally Posted by JessHaust
Re: One of my old high school friends is a crossdresser!
