So, in this post, lets talk about the fantasy of having a generic actually dress you up as a woman. Earlier in my life, this seemed like a great idea! Who would know more about dressing me up?
Ironically, the only one that did dumped me later before I went into the Army. As I moved forward and became better at the "science and artistry" of makeup, on occasion I would be the one getting the requests for help. I still do from beginning cross dressers. While I'm flattered, I simply don't labor under the idea I'm qualified to do it.
Although I wouldn't trade that one fantasy night of being cross dressed up by a generic, I necessarily wouldn't recommend it. Now, before your spouse or girlfriend wants to seek me out and "bitch slap" me-hear me out. Many women are good at understanding what looks good on them but maybe not so much on you. My deceased wife of 25 years rarely wore makeup at all and asked me for help when she did. Also I will refer you to Maria's blog "A Cross Dresser's Wife." for a different "look" at this topic.
Then, there are the generics who sell the lines of cosmetics such as Mary Kay. Again, a little research is in order. For example- in the Dayton, Ohio area there is a representative who has experience up to and including drag queens. Two summers ago, I contacted her about a consultation, explaining quickly I was not a drag queen. I simply wanted her to share her makeup expertise with me-woman to woman. She did, I was quite satisfied and if you are in the Dayton, Ohio area, I can share where you can contact her. Be aware though, the product line is not inexpensive.
So, if you want to dress up or be dressed up as a maid that's all good too. Often a fantasy can be better than the real thing. And, if your dream is to be like the cross dresser at Halloween above-go for it! Just be aware fact and fiction can be mistaken for each other. Often without the best results.