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?

Ok that title is a bit of a paraphrase – here’s the full question I received: I’m still figuring out crossdressing with the support of my wife. The biggest challenge for me is how do you balance your feminine and masculine side? And did you ever feel guilty for being a married crossdresser, like you’re letting your wife and/or yourself down? If so how do you combat those moments? GREAT question! How do I balance the masculine and feminine side? I don’t really know, to be honest – the way I stay most sane, I think, is that I accept […]

Ask a Crossdresser: How do you deal with guilt?

So you’ve discovered that your husband is a crossdresser. Maybe you stumbled across their hidden cache of clothing and makeup, or after years of bottling up a secret which they thought was shameful they couldn’t take it any longer and revealed it to you. Maybe you’re scared and confused about what this means about him, and what it means about your relationship. Maybe you’re concerned that having hidden something for so long, you don’t know who he is, or maybe you’re worried that if he’s been able to hide this from you, what else could he be hiding? It’s very […]

Help! My Husband is a Crossdresser!

Why take NSFW photos? Of course, I want to be viewed as a good example, a model crossdresser – someone who comports and conducts themselves in a manner that is respectable and does not adversely affect society’s view of the crossdressing community. I hope I do this well, and if you believe this is not so, please let me know. I will repeat, over and over again, until I am blue in the face under my many, many layers of concealer and foundation: This is not a fetish for me. This is not sexual. This is not how I get […]

Ask a Crossdresser: Why do you have NSFW photos?

I actually get this quite a lot – got this from a coworker most recently What’s the difference between drag and what you do? I get this a lot, actually. Once, in Mac (the makeup store, jeez you guys) I was in male-mode, buying makeup – and the super helpful assistant asked “So, are you a performer?”, clearly intimating I was a drag performer. Honey. No. Similarly, I’ve had friends ask me if I’ve ever considered getting up on stage and doing an act. Good lord, most of the time I just want to be left alone! Getting up on […]

Ask a Crossdresser: Crossdressing vs Drag

So like, when you’re dressed up, what bathroom do you use? I had a co-worker ask me this once (HEY, IT STILL COUNTS) and I forgot to write about it. Also, a commenter asked a similar question, and it definitely deserves a thorough answer. So. When I’m at work and I’m dressed up, I use the men’s bathrooms. Since I present as female maybe 10% of the time, it seems inconsistent to pick and choose which bathroom I’d use at work. Almost certainly, no one would have any issues with me using the women’s bathroom, but it still feels a […]

Ask a Crossdresser: Bathrooms

I am myself a crossdresser, lucky to have an encouraging girlfriend, but I’m still on the closet. My outings are as a male wearing girls clothes, jeans or blouses. I have to say here that I don’t live in such a forward-thinking society, thus, the fear of rejection is greater in comparison to probably where you live. To the point: when I decide to dress-up I always think of the people I’ll meet – my coworkers, or more terribly, family. I think of everyone but myself. If I think I won’t be seeing them that particular day, I go for […]

Ask a Crossdresser: Other People

Which way do you dress most of the time? What percentages if you had to estimate? I would say 90% of the time, I’m dressed as a male. Frequency varies a lot. Maybe I’ll go a month without thinking about it or dressing, I’ll get a (horribly itchy) beard going. And then maybe the next month I’ll dress up at work maybe once or twice a week. There’s no real pattern – it’s really just whenever mood and opportunity strike! (I mention opportunity, because some days at work I end up having to interview people, and regardless of mood, I […]

Ask a Crossdresser: How often?