I am headed out of town on business and I have the opportunity to explore my freedoms a bit. In no way am I able to pass at this point, so I am thinking of bringing some gender blurring clothing and wearing some light makeup, (I.e. a small pair of Mary Janes or some 2.5? heeled booties, some stylish gender neutral dress jeans and a top, some nude color lipsticks some nail polish and my feminine jewelry)...
I find it rather exhilarating to think about and have discussed it with a female friend of mine and she?s very excited for me. She has confided very personal secrets to me, about her life, and we have a strictly plutonic relationship. She is a very good sounding board for me. I plan on ubering everywhere I need to be.
My concern is..... I?m gonna get out of town and choke. Lol
I?m afraid I won?t be able to keep my nerve up and will waste this golden opportunity that I have, to dress gender neutral/leaning toward feminine, chance that I have.

Has anyone else ever had this opportunity and just went out for the first time in mini heels and jeans and blurred the lines? What were your experiences and did you get harassed? What should I expect?

Thanks