So I've reached a completely new place, thought I'd share my timeline in case people relate:
9 yo -- Secretly try on panties from the wash, like the way they feel
14 yo -- First paycheck, make several passes at lingerie dept before working up courage to stop and check out bras, helpful saleslady asks if I need help, I tell her I'm looking for my first bra, she's super sweet and helpful... I'm keenly aware of others hearing the discussion and very embarrassed, but manage to settle on a bra
15 yo -- By now I have a nice collection of bras, love the Playtex 18 hour bras. I wear them to school and work under at least two shirts at all times.
16 yo -- Embarrassed and disgusted with my habit, I throw all bras away and swear I will never wear one again
18 yo -- I have a full collection of bras and panties again... I talk to my mom about it because I think she knows... she didn't. She makes me promise to seek psychiatric help.
20 yo -- I see a psychiatrist, I tell her about the crossdressing problem, she tells me it's not a problem, I insist to her that it is as everyone who knows about it thinks so. She says if I THINK it's a problem, thinking so is a problem, and we can work on that... but the crossdressing itself is not a problem.
22 yo -- After a couple of second opinions that agree with this perspective, I finally allow myself to crossdress guilt free, I buy wonderful bras, I wear them daily... not really interested in makeup, dresses... not even panties! Just bras.
24 yo -- A co-worker finds out I'm a CD, sends out a mass email to everyone at work about it... I feel destroyed. Surprisingly everyone but a small minority is extremely supportive, some female co-workers offer to go shopping for bras with me.

30 yo -- I dress up to the nines, heels, dress... everything. I take a shopping tour of Seattle, nothing but positive reactions, zero negativity. But I find dressing as a woman too time consuming and awkward, I chalk it up to experience and leave it be
38 yo -- Still wear bras daily, stayed with my dad for a while, he catches me wearing a bra... very awkward, I barely know him. Shortly after he asks me to leave, it would have hurt a lot if I had known him in the slightest, but it still hurt.
40 yo -- Try to dress up again to the nines for halloween... finding it really comfortable and relaxing, trying the whole outfit ahead of time and going out in public. People are perfectly nice to me despite not being the least bit passable, people call me "ma'am" and "miss" which feels very flattering. After a week of this I decided I'm going to transition to full time dressing up, I've bought lots of additional makeup and will need to learn how to use it, I ordered 3 more dresses and also a skirt and blouse. I have two sets of expensive gel breastforms that make me super busty and really fill out the dresses.
So yeah, I think I'm pretty well committed, I will probably still go out as a man for some percentage of my time but I think that percentage will get smaller as time goes on!

Any feedback on how typical my experience is would be greatly appreciated, I want to know how the paths of others are different or similar to mine. I just got home from the movies, I wore a pink dress with a low cut that shows off cleavage, wore makeup, pink bra, pink panties and pink purse. I wasn't sure if I could hold it so I was stressing out over whether I should use the mens or ladies restroom, but the manager solved the problem by asking me to leave as he noticed I saw two movies after buying only one ticket and was about to walk into a third. D: He called me ma'am though and was very polite.