Crossdressing, etc.

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!

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

03/01/2014 tagged crossdresser / question / 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

12/01/2013 tagged crossdresser / question

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

11/01/2013 tagged crossdresser / family / question

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?

10/01/2013 tagged crossdresser / family / questions

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?

09/01/2013 tagged crossdresser / question / why

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

08/20/2013 tagged crossdresser / dating / questions / relationships

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

08/01/2013 tagged crossdresser / family / marriage / question

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?

03/02/2011 tagged crossdresser / transition / transsexual

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?

02/23/2011 tagged crossdresser / gay / questions / thoughts