First time poster, I figured I would share my story, partly if anyone else is interested, partly for myself and finally to introduce myself to the community.
One of my earliest memories (I was probably 4 or 5) is me going into my mothers bedroom, dressing up and smudging on some make-up, high heels and then strutting out in full dress to surprise my mother and her best friend, I remember getting some laughs followed by a talk on why I should not dress as a girl.
My family has traditional values and passed these on to me leading to me feeling very guilty and ashamed as I continued to wear my mothers and sisters clothes throughout my childhood and teens. I always hated sports, but enjoyed singing in the school choir, naturally I ended up hanging out with the other geeks, playing chess and messing with computers.
I started puberty very early, as I became interested in sex I automatically went after girls, I was so tied up inside that the thought of going out with men would make me sick. Whenever I would fantasize I would always think about everything from the female side, how it would feel, what she/me desired, I never had any fantasies with me in the "male" role.
If I masturbated en femme I would get totally disgusted with myself after I finished, tear everything off only to put it all back an hour later, one time when I was 17 I got very drunk, spent a night with a man with the same result, I was totally disgusted with myself and ran out faster than you can say "Morning".
As I got older the pattern continued, I would purge, throwing away any female items I had accumulated out of shame but then repeat the cycle, sometimes days later but other times several years went by.
Meanwhile I had a long time relationship with a girl in my late teens into my early twenties, in the end I walked away because I realized something wasn't clicking. It was at this point that I decided sexuality wasn't important to me, I buckled up and built a career in computer science, built a live-aboard sailboat, started a couple of companies, travelled all over the place and was very active in community work.
When I hit 30 I realized something was missing, when one does not really care if one lives or dies and is constantly depressed something needs to be done, so when I met an awesome girl I jumped head-first into another relationship, two years later I hit a low-point because I still wasn't happy and from deep deep inside my feminine self surfaced redoubled. This time it was different, the heck with social stigma and conventions, it was time for me and my feminine self to merge and become whole again.
Now I'm 34, I came clean with my girlfriend and being the awesome person she is she accepted me and my feminine self both, offered to help me with my make-up, helped me with plucking my eyebrows and made suggestions for my wardrobe. Now I live en femme all the time around the house and I've started making plans for my transition.
I've reconnected with my body, before I'd lost interest because I felt I would always be ugly no matter what I did, I've started exercising and eating more healthy and I'm happier than I've ever been.
Aside from shopping for female clothes I completed my first laser hair removal session yesterday and I'm getting my first corset sometime next week which should help in shaping my body. I've also made a promise to myself to start hormones as soon as I quit smoking (talk about a motivation).
All the shame and self loathing has now gone away, after living en femme for a couple of weeks I now feel more comfortable with my feminine self than ever before, having others accept me for who I really am is just the icing on the cake.
Random interesting observations (at least to me) and points I have made in the last couple of weeks:
I've accepted the fact that I'm bisexual, I still find women attractive but I've realized that I don't really want to penetrate them, one of the questions that I have been mentally asking myself when I see an attractive woman is: "Would I rather look like her or sleep with her", and the answer is always that I'd rather look/be her. For me this was a pivotal point in making up my mind to transition, I know it's the right thing for me.
One thing I discovered is that the laser hair removal business is full of people trying to rip you off and full of people that don't know what they are doing. I searched until I found a clinic with medical professionals, good equipment and good prices.
I highly recommend http://www.dermace.ca/ for anyone in Southern Ontario, $200 for full body session with facial hair, super service, friendly and professional!
Buying shoes is pretty hard for transgirs, Payless Shoesource has turned out to be my best source along with Aldo, both carry shoes in sizes 11,12,13 and frequently have wide and double wide at reasonable prices, some of the shoe stores that specialize in larger shoes are complete rip-offs with high pressure sales tactics and trying to sell you shoes for $300-500. Another favourite for clothes is Winners, for once it's good to be on the larger side for a woman since the outlets and discount stores tend to have more items for us odd sizes.
There is a brand of control panties sold at Shoppers Drugmart (Pharmaprix) called Secret
http://www.secretlegwear.com/products/ultra-firm-shaping-brief-77.aspx, they are mostly known for their pantihose but I've found the shaping underwear great for tucking, it's comfortable, invisible under tight clothing and flattens everything really well (my girlfriend was perplexed because she could not figure out where everything went and could not see a bulge).
I think that's enough of a rant for one night.
Antonia