February 27, 2007 1:55 AM GMT
Well...........it's a complex issue.
Long-term, I recommend two books MEN ARE FROM MARS, WOMEN ARE FROM VENUS. They will help you understand women's brains and culture and this will help you meet her needs as well as learn how to behave as a member of a new gender-culture. For those who are transsexual, this is easier because their brain structure is so female they do it naturally. For those of us further toward the blue end of the spectrum than our TS sisters, who have known it from childhood, we need to overcome our "training" in boy-culture. Another good book for understanding women is WHY MEN ARE THE WAY THEY ARE (which is actually about why women are the way they are but men don't read books like that and women wouldn't buy it if it was WHY WOMEN ARE THE WAY THEY ARE....which it is.)
Short-term....ask and listen. Wendy is a LOT more pleasant to be around than He is so just being me makes my SO much more comfortable. Be especially thoughtful and focus on her needs. Do the kind of things girls do...offer to get beverages, do the cleaning, etc. If you can't cook, provide some take-out food. Just be extra nice. Don't force it.
I recommend, initially, casual, ordinary-girl clothes. Perhaps one little black dress outfit. Steer clear of the more "exotic" clothing styles unless your girlfriend indicates an interest in you wearing something in a "street-walker" outfit. Even a pair of jeans or slacks might come in handy. If you have a favorite outfit you are dying to try with "the whole works", go for it. Leave yourself as many options as possible to maximize the chances to enjoy yourself. Your friend may want to choose outfits for you as well. My SO is quite a fashion expert and a cosmetologist and even the clothes I get from her are color coordinated and suitable for my age and build. Your friend's interests and desires may be quite different. Ask her. Listen. Even if it's not what you want, be open minded. I am wearing things now I would never have picked for myself and love them. Be flexible. Have fun. Don't make it stressful or be too rigid about what you want. Share your feelings and thoughts...that's what girls do with each other. Your friend is likely to enjoy having a new girlfriend as well as a boyfriend.
Long-term, you may find that your choices and her advice are not your best choice for passing or for you. Don't worry about it. This is about having fun and letting yourself go. Fashion, style and passing can come later. Just have fun. Afterwards, talk about it with your girlfriend and plan your next time together. The day after you go home....call her and tell her how much you enjoyed it and appreciate her help and friendship. This is important. Don't forget.