Hookup with a crossdresser

all the tips i can think of are, be open about your nervousness and see if they are chill and understanding about it and allow yourself to say no in case things move too fast for you, don't stress yourself out about missing out on something, opportunities come again and if they are chill you all can try another time in case.

You and him are there to have fun. Just remember that when you’re nervous

If it makes you feel better, I'm really looking forward to your update! Sharing your story will help others step out of their comfort zone and try new experiences.