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 liz@myweekendshoes.com and I’ll do my best to answer!

Why do you actually feel the need/want to cross dress? When did it start? Why do I feel the need to do it? Honestly, I have no idea, and sometimes I wish I could just store it away somewhere and never have to deal with it again, because apart from the last year or so, it’s been a burden – something I’ve had to deal with as a problem, instead of some inherent part of who I am, like a leg or an arm. Believe me, I wish I had a better answer for you!! As for when it started, […]

Ask a Crossdresser: Why?

 in Ask a Crossdresser  tagged crossdresser / question / why by
Liz, I stumbled upon your blog and the ask page. I am a mostly straight man attracted to M2F girls, and I have a first date with a crossdresser tonight. I was looking around online for dating tips, do’s and don’ts, but couldn’t find much. She seems rather eager for sex, which is fine. I will proceed with caution, but I’m wondering if I should show up with flowers and wine just as I might on a date with a GG. My instinct says yes be the same gentleman I am usually, but I was just looking for confirmation. Definitely, […]

Ask a Crossdresser: Dating a crossdresser

 in Ask a Crossdresser  tagged crossdresser / dating / questions / relationships by
You said you were married. How did you bring it up with your wife? What was her reaction? Was it before/after you started dating/married? So my wife and I were friends online for a looooong time before we were ever romantically linked, and yeah, she knew at least 3 or 4 years beforehand. I guess a lot of things were made easier by the fact that she knew – I suppose she knew what she was getting into, lol – but I was definitely worried about it for a bit, and yeah, even now every so often I get worried […]

Ask a Crossdresser: Your wife

 in Ask a Crossdresser  tagged crossdresser / family / marriage / question by
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Personally: No. I am male, in both body and mind. This is an important point. The parts that we are born with are not the 100% guarantees of gender that some people feel that they are. Gender is something that we carry around with us in our minds – it is who we are, as opposed to what happens to be in our underwear. It’s also worth nothing that you aren’t necessarily EITHER male OR female. Think of gender like the colors black and white – you can be a very dark grey, or a very brilliant white, or equally, […]

Ask a Crossdresser: Will you transition?

 in Ask a Crossdresser  tagged crossdresser / transition / transsexual by
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Short answer: No. Although some crossdressers might be gay, the majority aren’t. It’s an important question. Initially my thoughts on this were “It shouldn’t matter! There’s nothing wrong with being gay!”. While I agree wholeheartedly with the latter, the former is clearly incorrect: it *does* matter a great deal in some cases. If you see a crossdresser in the street and you immediately associate them with being gay, you’re guilty of making false assumptions, but that’s of no real consequence. If you find out after 20 years of marriage that your husband is a crossdresser, and your mind jumps to […]

Ask a Crossdresser: Does it mean you’re gay?

 in Ask a Crossdresser  tagged crossdresser / gay / questions / thoughts by