passing convincingly as a woman in heels and clothes

Hello I need advice please folks Iam a 25 year old male of 5ft 5” height and slim build living in north wales, united kingdom and i need to pass convincingly enough as female whilst on a late night walkabout to passers by and such ideally being fully dressed in normal female clothes ie skirt blouse heels etc. Also could any women reading this let me know how far it would take wearing heels for them to become very uncomfortable, my apologises for this somewhat random question I realise there are hundreds of variables but iam just asking for a ball park figure so that when i plan my route I will definitely get to experience what high heels are capable of inflicting lol any replies will be gratefully recieved Thank you