Emmi, if you're TG or possibly TS, its not about wearing pretty dresses...actually, the big thing is to be able to live in real life....to integrate your desire to present as a woman with the rest of your life. How you relate to your wife, kids, co-workers, neighbors, etc. Its not impossible...but you need to think about and carefully plan your emergence...rather than just sitting around fantasizing about it.
By the way, I dress every day, go out nearly every day and there are just few occassions where a cute dress really works. I love dressing up, but I also like to blend in. Today, I went to the store in a Shaker-knit tunic and white jeans. I looked good, I felt good about myself and I blended in pretty well with the other ladies at the grocery store. (Other than the fact that I'm 6'2" in bare feet!)