Crossdressing Articles

My thoughts about how to approach life as a crossdresser, and how to deal with it.


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Many years ago, I made a promise to my wife that if and when she became pregnant, as a show of solidarity, I would sport a beard the whole time for her benefit, as a lover of a good beard. Then, at long last, sometime last year she got pregnant. Thus began the long hiatus of Liz. Actually, that’s probably not fair. My dressing up had slowed to a crawl before that, and I hadn’t really dressed at work for many, many months. I suppose that I was already on a down-swing, and the bearded-ness, and general mental-fuzziness from there […]

Dressing again after a long hiatus



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You’re so vain – I bet you think this post is about you, don’t you? You might be right. I tend to be an over-analyzer. My teenage years (which I might counter-intuitively deign to leak far into my twenties) were plagued by late-nights in bed trying to sleep, playing conversations with people I’d had that day over and over in my head trying to glean more meaning than was superficially apparent from the words that they actually said, whilst also worrying about whether or not my responses were appropriate, or whether I was able to make myself fully understood. That […]

The Vain Crossdresser: A Defence of Vanity.



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I read an article not-too-long ago at The Onion, titled Woman Feels Like She’s Finally Ready To Start Receiving Unsolicited Vulgar Messages Again. (If you’re unaware, The Onion is a solid satire site). This particular article, as with all good satire, is both hilarious and extremely pointed – it hit its subject matter squarely on the nose – or went cleanly through it and continued on a path out of the back of its skull, if we insist on sticking to our ‘pointed’ metaphor. As a male on the internet, I in no way stand out. No one cares what […]

Male Attention (or “How To Make Me Not Like You”)



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One of the first questions we ask ourselves once we realise that we’re crossdressers/transvestites is “Why am I like this? Why am I a crossdresser?” Usually it’s not from a place of genuine curiosity, but a place of shame, or of misplaced guilt, or of anguish, because we’re suddenly assaulted by this reality of being different from everyone else – not by choice, but by circumstance, as if Fate has dealt us a shitty hand that we have no choice but to play. Well, ok. That’s one way to look at it. Another way to look at it is as […]

Crossdressing: Nature or Nurture?





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Living in a different country than my parents means that on occasion I get to travel back to the motherland that is the UK and hang out with them for a bit (along with not paying for a hotel, which is quite nice). We’re a bit boring – we tend to just sit around watching TV, but then again, that’s what we always did when I lived there; sometimes I think it’s a miracle that my eyes aren’t actually rectangular. I’ve mentioned before that I’m very open about my crossdressing. My parents know about it – I don’t think they […]

Is Crossdressing Funny?