Ask a Crossdresser: Dating a crossdresser

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, definitely, definitely treat it as any normal date, because really, that’s what it is! When interacting with a crossdresser, it’s always best to treat them like you would any other lady. Regardless of the reason for why people crossdress (gender identity, fantasy, whatever) it’s important to respect what they’re doing – if they’re presenting as female, you should treat them as such.

Hope it went well!

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