The other day I read about a local makeup artist who is offereing her services for a fixed hourly rate and she has a creative edge, has some experience in fashion, costume, etc. I contacted her to see what she how she would react to doing male to female makeovers for a party. She was really enthusiastic, said she has done male to female before. Its a bit hard to justify to hire her for one session just for myself, but she agreed to break it up so I could do a couple sessions which is pretty cool because then I can try at least a couple ideas and work on a costume between them. She also seemed to have no problem doing more than one person at a time which may work for a couples theme with my wife and I. She was also willing to help me learn how to do it myself, wants pictures of my face so she can think about bone structure and how to make it work.
How cool is that? Now, I'm challenged to come up with a really cool costume idea...