Ask a Crossdresser Archives - My Weekend Shoes https://www.myweekendshoes.com/category/ask-a-crossdresser/ Crossdressing, etc. Sat, 30 May 2020 20:28:29 +0000 en-US hourly 1 https://wordpress.org/?v=6.9.4 https://www.myweekendshoes.com/wp-content/uploads/2017/06/cropped-sitelogo-1-32x32.png Ask a Crossdresser Archives - My Weekend Shoes https://www.myweekendshoes.com/category/ask-a-crossdresser/ 32 32 Ask A Crossdresser: Names https://www.myweekendshoes.com/2020/05/ask-a-crossdresser-names/ https://www.myweekendshoes.com/2020/05/ask-a-crossdresser-names/#comments Sat, 30 May 2020 18:48:49 +0000 https://www.myweekendshoes.com/?p=3919 A friend of mine recently asked me “So how did you pick out the name Liz Summers?” upon which I searched back for the blog post where I explained it. Well, it turns out I never did. Which brings up a good point – why even have a female name? I’m not female, I have […]

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]]> https://www.myweekendshoes.com/2020/05/ask-a-crossdresser-names/feed/ 15 Ask a Crossdresser: Is just dressing enough? https://www.myweekendshoes.com/2015/11/ask-a-crossdresser-is-just-dressing-enough/ https://www.myweekendshoes.com/2015/11/ask-a-crossdresser-is-just-dressing-enough/#comments Sun, 01 Nov 2015 16:19:47 +0000 http://www.myweekendshoes.com/?p=2136 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 […]

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]]> https://www.myweekendshoes.com/2015/11/ask-a-crossdresser-is-just-dressing-enough/feed/ 8 Ask a Crossdresser: How do you deal with guilt? https://www.myweekendshoes.com/2015/10/ask-a-crossdresser-how-do-you-deal-with-guilt/ https://www.myweekendshoes.com/2015/10/ask-a-crossdresser-how-do-you-deal-with-guilt/#comments Tue, 20 Oct 2015 15:57:24 +0000 http://www.myweekendshoes.com/?p=2139 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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]]> https://www.myweekendshoes.com/2015/10/ask-a-crossdresser-how-do-you-deal-with-guilt/feed/ 4 Ask a Crossdresser: How to be a good friend https://www.myweekendshoes.com/2015/10/ask-a-crossdresser-how-to-be-a-good-friend/ https://www.myweekendshoes.com/2015/10/ask-a-crossdresser-how-to-be-a-good-friend/#comments Mon, 12 Oct 2015 15:20:06 +0000 http://www.myweekendshoes.com/?p=2133 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 […]

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]]> https://www.myweekendshoes.com/2015/10/ask-a-crossdresser-how-to-be-a-good-friend/feed/ 1 Ask a Crossdresser: Sexuality while dressed https://www.myweekendshoes.com/2015/09/ask-a-crossdresser-sexuality-while-dressed/ https://www.myweekendshoes.com/2015/09/ask-a-crossdresser-sexuality-while-dressed/#comments Tue, 01 Sep 2015 16:53:58 +0000 http://www.myweekendshoes.com/?p=2030 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 […]

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]]> https://www.myweekendshoes.com/2015/09/ask-a-crossdresser-sexuality-while-dressed/feed/ 6 Ask a Crossdresser: Why do you have NSFW photos? https://www.myweekendshoes.com/2015/06/ask-a-crossdresser-why-do-you-have-nsfw-photos/ https://www.myweekendshoes.com/2015/06/ask-a-crossdresser-why-do-you-have-nsfw-photos/#comments Wed, 10 Jun 2015 18:11:31 +0000 http://www.myweekendshoes.com/?p=1916 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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]]> https://www.myweekendshoes.com/2015/06/ask-a-crossdresser-why-do-you-have-nsfw-photos/feed/ 2 Ask a Crossdresser: Crossdressing vs Drag https://www.myweekendshoes.com/2014/09/ask-a-crossdresser-crossdressing-vs-drag/ https://www.myweekendshoes.com/2014/09/ask-a-crossdresser-crossdressing-vs-drag/#comments Mon, 01 Sep 2014 19:00:02 +0000 http://www.myweekendshoes.com/?p=1218 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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]]> https://www.myweekendshoes.com/2014/09/ask-a-crossdresser-crossdressing-vs-drag/feed/ 1 Ask a Crossdresser: Bathrooms https://www.myweekendshoes.com/2014/08/ask-a-crossdresser-bathrooms/ https://www.myweekendshoes.com/2014/08/ask-a-crossdresser-bathrooms/#comments Fri, 01 Aug 2014 19:10:11 +0000 http://www.myweekendshoes.com/?p=1222 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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]]> https://www.myweekendshoes.com/2014/08/ask-a-crossdresser-bathrooms/feed/ 7 Ask a Crossdresser: Other People https://www.myweekendshoes.com/2014/07/ask-a-crossdresser-other-people/ https://www.myweekendshoes.com/2014/07/ask-a-crossdresser-other-people/#respond Tue, 01 Jul 2014 14:00:13 +0000 http://www.myweekendshoes.com/?p=1276 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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]]> https://www.myweekendshoes.com/2014/07/ask-a-crossdresser-other-people/feed/ 0 Ask a Crossdresser: How often? https://www.myweekendshoes.com/2014/06/ask-a-crossdresser-how-often/ https://www.myweekendshoes.com/2014/06/ask-a-crossdresser-how-often/#respond Sun, 01 Jun 2014 20:32:51 +0000 http://www.myweekendshoes.com/?p=798 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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