I regret ever starting crossdressing; first premonitions that it was bad happened when I shopped for my first skirt [HS], skirt suit [Jr year college], and during my college years. It caused my Project partners to try to blackmail me and result in a C in Sr Design Class, - I fear this affect my Mech Eng career.
And it hurt me in many jobs. I lost many jobs, job interviews, and didn't go temp to perm because of it. So life sucks. I feel I would have had a stellar career with hardly any gay discrimination if I was never a crossdresser. I think I could have been rich if I wasn't a crossdresser, and that I could get more jobs through networking, connections, or just people being favorable to you.
And then the social life hurts too. I don't hang around or have any gay friends, and straight people don't want to associate with you if they know you're a crossdresser. I notice I get shunned by the in crowd and connection because they know about me. They wipe their hands across their chest as a signal / insult that I crossdress.
They just can't seem to accept that some people just want to enjoy wearing the other sex's clothes. They then associate you with being gay.
So the only reward I get from crossdressing is the feel of wearing the clothes, the fetish, and going out and passing as a woman.
Do you regret crossdressing? How has it hurt your life?