>>17505080My theory: The lack of authentic femininity in the lives of intelligent young men has caused them to generate femininity internally to sate a need that should be acquired externally.
When everywhere you look are tomboy girlbosses, and culture is constantly putting the man with boobs archetype in place of the damsel in distress, you're need to feel masculine ironically has you exploring your feminine side searching for the "other" to define yourself by.
In this cultural context I believe that crossdressing (which I do from time to time) in private as part of normal masturbation practices, while not healthy per se, is an effective treatment for the underlying dysphoria surrounding the male sexual identity. ie. if throwing on a dress from time to time helps you get comfortably with yourself as a man, then do it. The line is only crossed when crossdressing leads to unhealthy practices like sodomy or poor sexual hygiene.
Ideally society would correct itself are recognize that men and women need each other in order to be men and women, thus removing the cause of the dysphoria, but since that's not likely to happen, certainly not in a reasonable time frame, easing the distress by treating the symptom, particularly in such a harmless way, is sensible.