I believe that crossdressing is more biological than psychological. Only about 3-4% of the population enjoys crossdressing. If it was contagious then the percentage would be much higher. Where I went to school we had pep-rallies with short humorous skits. It was common to include some crossdressing in the skit. Also my school had womanless pageants during spirit week. I would guess that about 50% of men crossdress at some point in their lives, but for the vast majority they feel nothing special from it.

I believe that our brains are hardwired for crossdressing. When we crossdress our brains interpret it as actual contact with a female. Our brain releases a host of feel-good neurotransmitters (dopamine, serotonin, oxytocin and others) which produce sensations of well-being, comfort, pleasure, sexual gratification and self-identity (bonding). We love it. Most non-crossdressers feel nothing but embarrassment and they do NOT enjoy it.

Perhaps some of us were hardwired at an early age but never experienced the right trigger until puberty, or even later.