I’ve had many of the same external and internal experiences you are mentioning. Widespread reluctance to let biological women or men enjoy the things assigned to the other sex is the source of all kinds of personal and social problems for a lot of people.
I finally found a cure for the gloomy soup and paralysis of depression: positive and life affirming action. I’m experimenting right now to see if I as a male can effectively expand the restrictive cultural mindset about appearance and biology and gender. I’ believe my biology is not determinative or restrictive of my gender, and the experiences I seek in the feminine are available to me as a male.
I want to experience what I see as desirable parts of the woman’s world, but I don’t want to have to make myself physically more like a woman. It seems a scary and difficult course of hormones and surgery, and if that isn’t necessary for my psychic well-being, so much the better.
People dress up or down, more wild, more conservative, more goth, etc. when getting a job or leaving home. They expect it to be understood they are choosing a new relationship with their society.
In the same way, nothing prevents a willing and loving person from letting others express gender in the way they feel it, and I’m not reluctant to ask for that now from those around me.