Yes I have crossdressed most of my life and for the last 5 years I have gone out a couple times a week. As for tips or help there are many options. Most big cities have businesses that will do makeovers for crossdressers but costs some money. Most cosmetic counters at stores like Nordstrom’s or Macy’s are more than willing to help as a lot of them get a commission. Find a female friend that is willing to help, this takes some trust. Also Facebook is a wonderful way to meet other crossdressers and get support and help. Here in Portland Oregon we have a T-girl yahoo group that has 230 members and on a Friday night we can have 15 to 40 of us out together. Find friends that you can go out with as it really makes it a lot easier.