I want my girlfriend to dress me up like a girl, like makeup and everything. Its always been a dream of mine to become a girl for a day. I also like to crossdress sometimes, but she doesn't know. How do I go about asking?
Most Helpful Girl
I would start out asking her if she found it odd if she came home one day and saw you wearing a dress or something of the sort. Based on her reaction you should be able to decide if asking her if she would dress you up would be a good idea or not.0
Most Helpful Guy
You can ask her to help you to dress as a woman for Halloween.0