Crossdressing Articles

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


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The last few years, as part of my general plan to be better at certain things, I have a habit of setting a year-long goals for myself, with some monthly sub-goals. One of my goals was to write a blog post every month. So far this year, I’ve written nine – this will be number ten! 83% completion isn’t the worst, especially given everything that’s happened this year. I also have a goal to read a book every month (currently at 50%), to run (33%), and some others. My dressing goal is at 9/12, so 75%. Not the worst, I […]

Crossdressing Goals



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I couldn’t tell you what triggers the need to dress. It’s a lot like… uh… herpes? Like it’s just bubbling under the surface for weeks and months everything’s going fine and then BAM IT IS TIME FOR SHOES AND MAKEUP OMG!!!11oneone etc. People have mentioned being triggered by stress, or dressing to relieve stress, but it’s not something I’d ever experienced before until very recently. My last post talked about the death of my dad. We knew it was coming for 18 months, and while it was awful all the way through, it wasn’t unexpected. A month before he died, […]

Crossdressing and Stress



Following on from my previous blog post, I wanted to talk a little about making dressing up and getting out there a bit easier. The number of days where I had decided I was going to dress up, only to end up not doing so, is depressingly large, and each time, there was always some reason why it wasn’t practical to do so. Fear, I suppose, was one of the biggest hurdles to get over. That’s still a bit of a work-in-progress – each time I dress up, there’s always a little bit of fear, and given the long hiatus, […]

Pragmatic Crossdressing: Getting out the door more easily



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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”)