Like BriannaJ, I also had an understanding mother.
I knew early on I was different but didn't even consider transitioning until my mid-30s. When I was 4 to about 6 or so, I played dress up with my mother's and sister's and shoes and clothes, they both thought it was cute and played along; my father, however, was a far different story.
When I was about 12, Dad started traveling extensively and I started dressing again only to be caught by my sister playing in her dolls and wearing Mom's hose and one of Sissie's dresses. By then, my feet were too large for either's shoes... When Mom came home, we had the first of many long conversations including subjects such as Christine Jorgenson and crossdressing was odd but not perverted. We then started building me a "secret" wardrobe that could be easily hidden when Dad was home. Even though I wore panties daily, I still liked girls.
In high school, I had to revert to boy's underwear for the year I had gym class and hated it. By the time I went to college, my parents had divorced, I had a good wig, a couple of bras and rice-filled bags to fill them and even went out a couple of times with Mom and sis as my alter-ego. Still thinking I was "just" a CD, I managed to suppress my urges with a heavy class load. After graduation, however, I started dressing almost nightly and wondered if there was anyone out there for me.
When I was 25, I met a wonderful girl. We fell madly in love but before I made any commitment, I respected her enough that I had to let her know the truth. I preparation for her arrival one Friday evening, I had taken extra care to be as womanly as I could possibly be wearing a blue skirt and matching pumps, ecru blouse and faux pearl earrings and necklace. We cried and hugged a lot that night but when she left, I knew not if I would ever see her again. I was startled when she just dropped in the next afternoon, unannounced. I was in guy's grungies, just back from work, when she told me to clean up and change, we were headed out. She also announced that my name was all wrong and christened me as Susan. We ended up at a lingerie boutique where she had pre-arranged an actual bra fitting with artificial breasts. I was in heaven.
Fast forward 10 years and she and I both knew CDing just wasn't enough and the first steps towards full transition were begun. Our young family had known Susan all their lives so nothing seemed amiss as together we began the process to complete the "real" me that had started to emerge all those years ago.
Unfortunately both my mother and bride have passed on to another place but without their Love, help and encouragement, I wouldn't be who I am today.
Susan
PS. Thank you for a great topic and walk down memory lane. And thanks also to those who have taken time to tell their stories.
edit: How could I have forgotten Love (with a capital L) in the last sentence? sb