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We all experienced these feelings in the early days of our journey.

I would advise one little step at a time to help you accept and feel confident.
Dressing and meeting a guy and going out is probably not the ideal first step to feeling at ease and comfy.
Maybe the aid of a dressing service, with a female attendee could be the best first step?
You will find the right service that will make you feel at ease and totally welcome in a neutral, no-distraction location.
Then build on that first step by attending a local girls-only gathering, supported by another member of the group.

It is daunting to take the first step/s but once achieved you will think why was I worrying ( as you will then want to go on and do more!).