Upcoming date - what to wear?

I've recently started crossdressing, and I've found myself in a "first." I hrecently got together with some friends where I was encouraged to present as "Stephanie." Well while there, I got asked out by an guy (who knows I'm a CD) for dinner at a pretty nice restaurant. I'm very excited (and nervous) - 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.

What should I wear? I think I'm as excited about the shopping and picking something out as I am the date itself, lol.


Most Helpful Guy

  • just 2 questions if u don't mind sharin... wot's yer sexuality? and wot made u start crossdressin?
    anyway... since he knows u r CD it's fine. also don't dress da way a guy likes... but da way u feel comfortable wid.

    have u ever tried stilettos before? if not better avoid... they r pretty hard to walk (never worn 'em personally. but many gals claim it needs some time to learn to walk stilettos).

    generally wot clothes do u prefer? of course i'm talkin about feminine or unisex clothes at least.

    • I've always really liked girls' clothes. I'd consider myself straight, but it's funny that I've found that I start thinking differently when dressed as a girl. I love skirts and dresses. Yes, I have worn stilettos. I really want to make him say "wow!" when he sees me.

    • huh... clothes cannot change yer sexuality as far as i know... but anyway.

      ok if u've worn stilettos and u've worn 'em before it's fine... maybe a blue dress would be pretty nice judgin by yer hair-color... especially if yer skin color's tanned

Most Helpful Girl

  • wear a nice dress.


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What Guys Said 1

  • Black mini-dress and thigh-high stocking, hold-ups would be enough for me! Or possibly black tights if you prefer. Should set off your blonde hair very nicely,


What Girls Said 0

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