Ask a Crossdresser

A list of questions people have asked me about my life as a crossdresser/transvestite, and my answers – Feel free to ask me anything!
Email me at and I’ll do my best to answer!

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?

When you’re dressed differently, do you alter your voice? Nope! I very briefly (in terms of minutes, lol) experimented with the idea, but A: I don’t think I could pull it off, and more importantly, B: It’s just not me. I kind of think of the whole crossdressing thing as just a different version of me, but one that’s still authentically me (if that makes any sense) – I don’t have a different personality or voice – it’s not a character or persona, it’s just a different expression of the same thing. Maybe that doesn’t make sense… lol For more […]

Ask a Crossdresser: Voice

So when you’re dressed as a man I assume you prefer to be called be the male pronoun of “he” and as a woman you’d prefer “she”? That was something my friend and I weren’t totally sure about at a drag show but I figured that if they were currently dressed as a woman they wanted to be called a “she”. Yeah, when I’m dressed up as a woman, it seems only right to be referred to as she. Being called “he” when I’m dressed up generally means that either I don’t look good, or the possible that the other […]

Ask a Crossdresser: Pronouns