Hehe Binx, I guess if it's worth saying once.... it's worth saying twice?
Keith,
I hope you don't get to feeling we are all preaching to you, or 'getting on your case'.
I think you can see this is all coming from personal experience.
Although my little list in the beginning seems comical, it actually is pretty valid.
There are many ways to initiate or educate your GF about men wearing skirts.
You know her, think about the ways she might be most accepting when hearing about men-in-skirts.
If you/she have strong religious feelings, perhaps finding a few quotes from your particular religious text concerning men and their skirts, could help.
If it's more of, "In America (if that is where you are) men don't wear skirts!), then take it from the perspective of kilt-wearing perhaps.
Although, I think for some folks it is still quite a leap-of-faith going from guys in kilts to guys in other sorts of skirts.
You can find many references here and in the old Tom's Cafe, to men who wear skirts in other countries.
Some of these skirts are: sulus, sarongs, dhotis, etc.
Find yourself a 'manly' sarong and just start wearing it around the house, indoors, at first.
If your girlfriend asks, just tell her the truth... you are comfortable in a sarong.
They are pretty cheap and depending on your build, easy to find.
I have had numerous women tell me, "My husband wears a sarong when we're on vacation to Hawaii.". I guess it just doesn't dawn on them that a sarong could be just as comfortable back home also.
You are going to see it here, again and again, that you should find a way to come out with your interest in wearing skirts.
Hiding it and having it come out later either accidentaly or on purpose can cause major problems in any relationship.
You do not want your GF to wonder why you 'hid' this from her all this time, nor do you want her to wonder what else you are hiding from her and how/when she will find out.
As painful as it may seem to be now, it will only be more painful the longer it takes to come out.
There should be no shame in you wanting to wear a skirt. There are only a small handful of countries in this world where a man is seen in a negative light if he is wearing a skirt... think about it.
Here in America, home of the 'free' and the 'brave', men are scared to wear clothing that is totally acceptable elsewhere in 'lesser developed' countries.
Such a sad mindset, isn't it?