There is absolutely nothing wrong with crossdressing. Yes society in general does tend to have views on what a male should be like and what a female should be like but that is slowly changing. If it makes you feel good and it doesn't harm anyone than do it. Who cares what society says. You may not want to do it when your out with your parents because they are from a different generation, but if your at a gay club no one will insult you or laugh at you there and there may even be other men crossdressing there. It's our ridiculous cultural values that make you feel ashamed. There is nothing to be ashamed about. The gay movement is having progress. Obama even has a transgendered man in his administration.