There are a lot of rules to this thread, please follow them as best you can. First, the main rule is if you decide to dress as a woman, you can NEVER switch back to being a male. You choose one or the other. The other rule is you can be a man in a dress. You don't have to be a woman. Third, assume that for some strange reason (parallel universe whatever) that current surgical procedures would be available to you in this era but nothing more. It would be, if you wanted, possible to get safe and cosmetically pleasing GRS, FFS, BA.
Now for the game:
People here say they dress for many reasons and often have fantasy ideals of an time in the past. What I want to try here is seeing who would actually live in that era, the reality of the era not the fantasy, as a crossdresser (no plans on changing anything, no hormones, no surgery but wearing the clothing 24/7 for the rest of their lives) or transitioning into being a woman. Limits shall be set. Like for the first era (and we may revisit other eras later if this goes well, you would be middle class. Not the extreme poor nor the upper crust. Middle working class.
Would you choose to live as a transgender person (assume also that you would be safe and society wouldn't care about your being trans but you get all the good and bad of being a woman at that time) 100 years ago? 1916.
Or would that not fit your perspective of being a crossdresser or emulating femininity?
It's my party so I may (like a dungeon master) clarify details of each response. Others may chip in too. Open to everyone (GGs included if they would live in that era as a woman). Now, fully understand the gender division at that time.
OK...go