question Archives - My Weekend Shoes

Crossdressing: Nature or Nurture?

Liz Summers — Sun, 21 Feb 2016 21:41:05 +0000

One of the first questions we ask ourselves once we realise that we’re crossdressers/transvestites is “Why am I like this? Why am I a crossdresser?” Usually it’s not from a place of genuine curiosity, but a place of shame, or of misplaced guilt, or of anguish, because we’re suddenly assaulted by this reality of being […]

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Ask a Crossdresser: How do you deal with guilt?

Liz Summers — Tue, 20 Oct 2015 15:57:24 +0000

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 […]

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Help! My Husband is a Crossdresser!

Liz Summers — Sun, 09 Aug 2015 23:21:12 +0000

So you’ve discovered that your husband is a crossdresser. Maybe you stumbled across their hidden cache of clothing and makeup, or after years of bottling up a secret which they thought was shameful they couldn’t take it any longer and revealed it to you. Maybe you’re scared and confused about what this means about him, […]

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Ask a Crossdresser: Why do you have NSFW photos?

Liz Summers — Wed, 10 Jun 2015 18:11:31 +0000

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 […]

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Ask a Crossdresser: Crossdressing vs Drag

Liz Summers — Mon, 01 Sep 2014 19:00:02 +0000

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 […]

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Ask a Crossdresser: Bathrooms

Liz Summers — Fri, 01 Aug 2014 19:10:11 +0000

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 […]

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Ask a Crossdresser: Other People

Liz Summers — Tue, 01 Jul 2014 14:00:13 +0000

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 […]

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Ask a Crossdresser: How often?

Liz Summers — Sun, 01 Jun 2014 20:32:51 +0000

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 […]

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Ask a Crossdresser: Voice

Liz Summers — Thu, 01 May 2014 20:31:47 +0000

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 […]

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Ask a Crossdresser: Pronouns

Liz Summers — Wed, 02 Apr 2014 20:33:56 +0000

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 […]

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