Upcoming Night Out and I need help?

Hi everyone. I am a relatively new crossdresser, and I was recently asked out on a date (in girl mode). I'm arguably passable, which is fun, and am certainly flattered to have been asked out.

Which brings me to my point of this question. I don't know what would be great to wear, as I've never been on a date from this side. We're going out next week to a nice restaurant and maybe drink after. I'm 5'7" 150. I plan on shopping on Monday evening, and so any help you can give would be great. What are good stores to hit? What would you recommend from an outfit perspective? I've definitely started to realize what a girl goes through when getting ready and trying to impress a guy!
Yes, he does know I'm a MtF cd. Thanks for the clarification.


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What Guys Said 1

  • Does he know you're a cross dresser? Just saying, because things may not go down well if he finds out and wasn't aware of it earlier. What you wear would be the least of your worries at that point.


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