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!


4
From another recent email I received: Are you ever afraid that, or do you ever have the feeling that just “dressing” isn’t or won’t be enough for you? That’s actually something I’m not worried about at all. For me, dressing is basically where it ends. I’ve never had any long-term desire to be a woman – indeed, the rare, short-term thoughts on it I’ve had have evaporated faster than what to watch next on Netflix. Further steps, like transitioning, hormones, voice-coaching, etc are just not something that drives me, or appeal to me. Quite the contrary – although I will […]

Ask a Crossdresser: Is just dressing enough?



3
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?



1
Excerpt from a recent email: I would like to pose a question to you, for your “Ask a crossdresser” section; How to be a supportive friend? It may seem like an silly question, but I think that there are many questions and insecurities that cross a person’s mind when faced with news about a friend/loved one’s crossdressing interests. In essence, a healthy dose of common sense combined with good communication is often the key, but maybe there is more? Are certain things okay to ask, others not? Is it better to be inquisitive, or best to stay quiet and wait […]

Ask a Crossdresser: How to be a good friend



5
Is it normal that I’m attracted to guys when I’m dressed? I’ve heard this a lot – enough for me to say “Yes, this is normal. Lots of people experience this.” However – I don’t understand it. I’ve heard lots and lots of people say that in the instances where they dress up, they find themselves attracted to members of the same gender. The thing I find curious is why that would be. Sexuality is fluid, absolutely – but I don’t feel more attracted to women if I’m putting up shelves, and I don’t feel like I start becoming attracted […]

Ask a Crossdresser: Sexuality while dressed



2
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?



1
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