My vantage from the cheap uneducated seats high and up to the left in some stadium, which makes me feel uncomfortable sharing to the head coach on the 50 yard line.
Redlines + Boundaries = No
Expectations to "Redlines + Boundaries" = Maybe
Expectations = Yes
The caveat to this, the person has to be a friend and in a discussion where communication and dialog is open and two-way.
To anyone else in life all three things above = No
tl;dr - example
So to do a give and take using your shared experiences when bonded with my past and present (hypothetical).
We both swap right, meet at Maggiano's some where and COVID is done. We talk about what turns on each other about the opposite sex.
We talk and we share and we both admit ok there is something here. Coffee, desert and we disappear
You are nervous because I stated one of my strong preferences is hair on a woman. You cringe. Am I honest, do I share, what should I expect.
At this point you have to answer a few of the things I listed above.
Prior to my "evolvement" I would have done what probably a lot of guys did. Kept my mouth shut, but then if you shared and showed who you were, but we all know and women have a sixth sense if a guy is lying. Who knows what happens.
Post "evolvement" if things "really" clicked, I would say if you are comfortable with me, please take it off I want to see the you as you are, but your body your choice. My view is if the wig is part of your identity and provides you confidence, why should I rob you of it. The thing is each interaction without full disclosure causes drift. Is it good or bad? Dunno, but the sooner disclosed the faster the bonding.
E.g. if I knew it was an extremely sensitive thing for you, I would try to make sure extra love, care, and sensitivity would be done. Soft touches on your head and strong focus on you as a woman.
I can't attack my boundaries and preferences where it might hurt with out the knowledge and disclosure. It would be a respect thing for me, but for some guys it would really show the work they have done on the masculinity and humanity.
You win some and you lose some. Great analysis BTW. I also hope my share using your shared experiences did not cause any discomfort and bring back bad memories. It was not my intent, and if I did I apologizes.
thanks now have a Mexican Coke, Espresso with Tiramisu , or a cold glass of sweet tea (or bourbon) on me :)