I've been doing alot of reflecting back on my teenage years, and thinking about how much I hated myself for wanting to crossdress, no matter how hard I tried to shake the urges.
I was raised in a church, and taught that being gay or bisexual is a sin, and that trans people are messed up in the head.. So when I would find myself putting on my mom's mascara and lipstick, I'd feel this rush of happiness flood over me, and then almost as fast as it came, it went away, leaving me feeling ashamed... staring at a freak in the mirror.. "What the hell is wrong with me"...

Once I moved out, around the age of 19, I started to order crossdressing items off the Internet. I'd have a pretty nice collection going, and then after a big dress up session, I'd feel ashamed of myself, and I threw EVERYTHING away. The infamous Purge. Well a couple weeks would go by, and I'd find myself searching for more stuff online to order.. It was just a vicious cycle.

My girlfriend at the time (now wife) found some pictures I had taken of myself dressed up.. At that point, we had been together for a couple years. I've wanted to tell her about me ever since I started talking to her, but could never find the courage. Well now that she saw pictures, it was pretty much out.
We didn't talk about the pictures for almost a year, until we had a "coming clean" conversation one night.. I told her that ever since I was little, I've been into dressing up like a woman. That I'm not gay. And it's not something I chose to be into..
She didn't really understand, but she said she'd do her best to try.

That's been 3 years ago or so, and over the time, I've slowly been introducing her to more and more things. She's taken me shopping for girl clothes, we've done makeup together, just stuff like that.

She's still not 100% comfortable with me crossdressing, but I can tell she's trying for me, which is all I can ask for!

So going from being depressed, hating myself, purging everything I would buy- to being happy, loving life, and not having any urges to purge... I can definitely say that my "High Point" in my crossdressing has been finally opening up to my love, and finally starting to accept myself!

What's your high point??