Okay, so... here's my life story?
1995: First innocent association with the female gender role in the form of playing the mom cat on the playground in first grade. I distinctly remember getting the butterfly feeling in my stomach when I did that. It just felt.. right.
2000: First encounter with anal masturbation. Middle school age. Immediately ashamed afterwards.
2002: First incident of crossdressing in private (stole mom's clothes)
2005: First realization that I was gay. Deleted all my gay porn out of shame, followed my immediately downloading more in the coming days. I ping-ponged like that a few times.
2007: Crossdressing in private regularly. I did become sexually aroused during cross-dressing, but CD was never required to become aroused. I think it was the thought of being a woman which just felt right? I have no idea. I remember also becoming aroused during leg shaving, at least at first. (Note: this is kind of what concerns me after reading that people who have sexual fantasies involving crossdressing aren't trans.. or something)
2008, February: Began to grow out hair to make myself look a bit better in the mirror when I was crossdressing.
2009, March: Met three girls at an anime convention. We began to regularly spend time together, and I asked them if they thought I would look good crossdressing at a later convention. They encouraged me and I bought a dinky dress at Hot Topic. Sexual arousal during crossdressing was still present.
2009, March-April: Began doing as little manual work as possible, to diminish muscles and prevent injury, in an attempt to look more feminine.
2009, May: I began having symptoms of which would later be determined to be ulcerative colitis. Freaking the eff out.
2009, July: Got a colonoscopy due to said symptoms. Everything checked out fine except for a tiny bit of inflammation inside the rectum. Was a relief.
2009, July: Went to the anime convention for which I bought the dress. I didn't pass, but it was fun. It felt good to dress as a female in public. I wasn't sexually aroused.
2009, October: Began having the same symptoms I had in May. Concern arose.
2009, November: After another convention at which I wore the same dress, the symptoms I had in May began to get bad.
2009, December: Diagnosed with ulcerative colitis. It was bad. I fell into a deep depression.
2010, January: Vivid suicidal visions started happening, usually associated with blood and crossdressing. Was very strange. (Note: colitis is a type of inflammatory bowel disease. It's an autoimmune reaction, and mine happens to be triggered by stress)
2010, March: Colitis symptoms not as bad, being controlled a little bit by medication I reluctantly began taking.
2010, April: Met the love of my life at a convention.
2010, June: Talked to said love on Facebook, and we met up at my house one night. We fooled around a little bit, that was all. The next morning, my colitis symptoms spiked and it was bad for a week.
2010-2011: I never liked it when my boyfriend took my picture, unless I looked passable in the photo. I began dabbling on the internet about transsexualism, and concluded that I didn't want breasts, didn't want the risk of hormones, and I'm not trans. Sexual activity with my boyfriend involved me crossdressing. Not always, but a lot. He didn't demand it of me, but I liked doing it.
2012, Jan: Got a job as a valet with my boyfriend. It's easy enough, and in Aug, 2013, I'll qualify for health insurance, so okay whatever. It was nice working with him. But... my thoughts about ->-bleeped-<- were evolving.
2012, April: Every day. Every day I see myself in the reflection of car windows, glossy paint on the doors, in the rearview mirror. Every day I see a man. A long-haired, big nosed man. I kept looking at him in the mirror. Every car. Sadness overtook me each time.
2012, May: My colitis symptoms spiked. Really badly. What I would in the months ahead discover was gender dysphoria hit me like a baseball bat.
2012, June: Colitis symptoms still bad. Suicidal thoughts haunted me again. Broke down at work and cried in the podium one day. Made an appointment with an LGBT-friendly doctor. Told him all what I just told you. He gave me a month to think about it and see a therapist.
2012, July: Went back to the doctor. Was prescribed finasteride. Symptoms still bad. Talking bloody diarrhea every day, 10 times a day. It was physically and emotionally damaging. Broke down and told my brother what I was doing with the medication and about the suicidal thoughts. He was supportive. (Note: I was no longer aroused by crossdressing alone by this time.)
2012, early August: Saw a therapist, finally. Told him about my primary concern at the time, which was the colitis. Touched on the dysphoria, but it wasn't his area of expertise so mostly we talked about colitis and its impact on my life. The next day was moving day for me and my boyfriend. We moved into an apartment.
2012, mid August: Colitis symptoms calmed down for the most part, after what felt like decades. It was a relief to finally not be bound to a toilet.
2012, August 20th: Prescribed Estradiol by the doctor. Colitis symptoms leveled out and I began to feel normal again.
2012, September-December: I would get occasional flashes of dysphoria-based suicidal thoughts. Mainly triggered when I would gaze at myself in the review mirror of cars I'm parking at work. Happening monthly, these episodes could last 5 minutes to two hours. The hour-long episodes featured vivid suicidal thoughts. It would scare me into tears or near-tears. I don't want to die

2013-present: Welcoming any new changes, but I still look at myself in the mirror in cars I'm parking and in all reflective surfaces I find in public, and find every male bit I can see. The vivid suicidal visions come maybe bimonthly now.
However...
As the changes become more apparent, I begin to fear what is to come. I begin to ponder if I made the right choice. I begin to think that maybe this whole transition thing was merely an offshoot of being so wrought with mental and physical pain with colitis. I fear not passing in every aspect. Voice, mannerisms, look, etc...
Maybe? Maybe I made a mistake? Should I stop before it's too late? I run these scenarios through my head to no avail.