I got asked out! What should I wear?

I'm a pretty new male-to-female crossdresser. I have some great friends, and we recently got together for a party where I was encouraged to attend as Stephanie. Well while there, I got asked out by an admirer for cocktails at a nice romantic restaurant. I'm pretty excited - my heart is skipping beats.

What should I wear? I've been on plenty of dates in "guy" mode, but never like this. From talking to him, I know he likes stilettos, nicely done make-up and painted nails. I'm 5'7", 148 lbs., long, wavy dark blond hair and blue eyes.

Can you help me with an outfit? I really want to make HIS heart skip a beat. Thanks in advance!


Most Helpful Guy

  • Wotever ufeel co. fortable with basically o' course


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What Guys Said 1

  • Uhh, does he know you are male?

    • Yes, he does know I'm a male!

    • Cool. Well if he likes stilettos and that is what you will wear then pair them with a nice evening dress if you want to look elegant. Can't go wrong with a long black dress. Long sleeves if you aren't comfortable with arm showing but if you are happy with your arms then choose sleeveless.

What Girls Said 1

  • whatever you feel comfortable, in but make sure you look good! & goodluck :)