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 until the friend raises the topic for conversation? Should one act differently, or remain the same?
Having a supportive, caring and loyal friend can be one of the best things a crossdreser (or anyone, really) can have! And definitely not a silly question at all! As you say, common-sense and communication are hugely important.
Your level of inquisitiveness might depend on your friend – if they’ve opened up about this to you, then you’re probably ok to ask whatever you want, so long as they feel like you won’t judge them for it. Personally, I’m super open about it and happy to answer questions, so long as they’re not…weird? For example, once when dressed at work, a workmate asked, in front of a few people, whether I was wearing women’s underwear too. Kind of inappropriate, given our relationship and the setting. If a close friend asked that in a private conversation, I wouldn’t have cared at all, and now we can talk about underwear :D
We spend a lot of our time fearing what could happen after telling someone about us, and having a non-judgemental person there to hear us out, understand, and accept us is worth their weight in gold. And definitely act exactly the same! They’re friends with *you*, not someone else :)
So long as you treat them with respect and sensitivity (like you would anyone else!) you will do fine :)
I would think a reasonable response to the underwear question might be “I’m wearing my underwear.”