For me, I think that it all began when I was an adolescent, about 60 years ago, when I first tried on Mom's bra. I developed a secret attraction to lingerie at that time and it lasted until I went away to college. Fast forward about 45 years and, frustrated and unsatisfied with my marriage, I secretly began going to pro dommes for BDSM, CBT, etc as I saw it as non-cheating on my marriage vows. On one such session, the Domme did the 'Forced Fem' session, completely dressed and made me up and then took me out to dinner as girlfriends. She had unlocked my feminine side and then years later, I began secretly wearing panties and bras whenever my wife was not around. She came home early one day and caught me in panties, recognized my interest in femininity and soon began to feminize me. Along with that control that She began to exercise over me, we began to practice chastity on the honor system. Only after I proved to be 'dishonorable' was the cage introduced to control the wanking. So, in short, my path went from Alpha Male to being feminized to chastity to caged.
Based on my discussion with other feminized men, I sense that everybody has a different story, commitment from their spouse/gf, and, in many cases, the feminization has been a culmination of secretly harbored, long time interests. If you would have asked me 10 years ago about this, I would have responded much like Chris82. Actually, it was the caring interest of my wife that enabled me to confront, address and enjoy my femininity. Our relationship and sex like has grown by leaps and bounds since She has taken control of my masculinity and turned me into her devoted and loving sissy!