Absolutely great advice so far. I especially like Fran's comment. I think talking to Cross Dressers will be really beneficial for you. Not only for general support and understanding, but for using clothes and makeup to best minimize any "masculine traits" you may have.
Finding guys to hook up - well, that's hard to gauge. Some guys dearly love meeting CD/TVs while others won't even consider them as options no matter how "convincing" they are.
Some things to consider about your body:
1) Hair loss can be corrected - Either surgically or with medicine (if it's bothering you at all, you may want to talk to your DR about Finastricide (sp?)
2) Neck, torso, hands, feet, and shoulders are something you will not be able to change, so learning how to work around them will probably be important. Remember though, women come in every shape and size - so there will be women who naturally have bigger shoulders than you (for example)
Shopping is actually easy:
1) Figure out your sizes and do it online - sizing can be tricky, so make sure you read the shop's return policy.
2) Walk into a store with a "list" and say you are having an anniversary, birthday, w/e for a friend/wide/mother and would like some assistance. Folks in shops love to help guys pick out clothes for the women in their lives.
3) If you are in a department store, and don't want to bother or are otherwise to afraid to talk to one of the employees - buy your clothes and then pick up a card or some wrapping paper (see above)
4) If you live in or near a city, most shops for "big/tall women" do a ton of business with all members of the local trans* community. There is a good chance they have a discrete changing room just for you.
5) Most important - Act like you have every reason to be in that place buying those items. If you act like people should be staring at you and whispering, they will. (Remember this every time you "dress up" and you will probably have a ball)
6) almost forgot - visit a local thrift store or second-hand shop. It's an inexpensive way to get some classic basics (black skirts, white tops etc.) as well as figure out what styles, cuts, lengths, colors , etc. work for you. I guarantee the people there won't care who you are or what you buy.
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