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 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

You mentioned going into public and getting respect whether you’re dressed as a woman or man, I was wondering about work and such. Where do you work? So like if you work as a crossdresser then obviously it’s okay at work, but I’m wondering how a different job/co-workers react if one day you come in as a man, and the next as a woman? So I work as a software developer in SF, which is helpful, since it’s probably the most accepting place in the country! It took a long time for me to start dressing at work. We had […]

Ask a Crossdresser: Work

Do you ever want to go all the way through with getting implants? What about the surgery of getting your penis removed and them making you have a vagina instead (again, sorry I don’t know the correct terms!!)? Implants and operations? nope. nope nope nope nope. hahaha – apart from the fact that I’m perfectly happy in my current body, and that I do consider myself male (maybe 20% female, lol), I honestly don’t think I’d be able to cope – it’s just far too much work to stay looking good. Getting ready in the mornings on the days that […]

Ask a Crossdresser: Surgery

Do you have children? If no, or intend to? Nope, no children yet – but hopefully soon :D We’re planning on having them in the near future – as for how we deal with things then, I’m uncertain about. Ideally I’d like to be 100% honest and myself around them – “sometimes daddy wears different clothes, and that’s ok” – but I do have that fear that when they go to school they’ll be the kid with the weirdo parents, and I’d hate for them to resent me for it. I actually had a friend at school whose dad was […]

Ask a Crossdresser: Children

Does you extended family know? (Parents, siblings, aunts, uncles, cousins, etc) What was their reaction? So I’m actually 100% open about it now – My facebook profile picture alternates between me dressed as regular me, and me in a wig and makeup and looking spectacular, lol – Everyone knows, and for the most part either don’t care, or at the very least, don’t give me grief about it. My mum I think is having the hardest time dealing with it, but then I also think she’s having a hard time dealing with the fact I’m not a twelve year old […]

Ask a Crossdresser: Who knows?