Why do some already 'successful' men troon out?

[Butcher Pete]

Pornsick perverts are gonna indulge in pornsick perversions.

 

[I (Don't) Have A Gun]

Define "successful."

There are plenty of "successful" people who are utter failures in their personal lives.

I'm going to assume by success it means money, career, a wife and / or children.
But at the end of the day money solves problems it doesn't buy happiness and more importantly fulfilment, and I've seen many unhappily married men who don't particularly love or care for their children.

From that perspective trooning out is probably just an extreme attempt to try and feel fulfilled, to fill that hole in their soul that money, a career and family couldn't. Certainly it might explain why a 40+ year old man suddenly decided to dress like a little girl. Now if it is successful or not is a different conversation...

 

[Pampered Degenerate]

In those cases, I believe that trooning out is the next logical step from engaging in sadomasochism, it's a humiliation fetish. See the Wachowski brothers, for example.

 

[Sweetpeaa]

In this case of Mr.Fong for an example I think this was just a case of lonely chink syndrome.