Where is the fine line?

Alright I am all for open mindedness, but maybe I am not this open.

Recently I was contacted on the dating website by a straight twenty-three year old male who is into (Drum roll please)........Cross Dressing. Is it me or does a straight male who likes to go around in lipstick and heels sound strange? My only question is why? When is there this line that forms between what qualifies you as gay, straight, or bi? Do we need lines or qualifiers at all?

Take for instance a new guy I met through a friend who is a straight gay porn actor, aka gay for pay. Now I understand that the gay porn industry is much more lucrative than the straight porn industry, but the whole act of having sex with another male while being completely and entirely straight is an oxymoron.

I guess to understand this concept I must first analyze myself a bit. I would not qualify myself as a lesbian, bi, and or entirely straight. I find women very attractive and wouldn't mind someday experiencing a little bit of something with another woman. I enjoy making out with females and unlike some of my other female counter parts it is not for the attention of males. However I do not feel I could be entirely with a woman. I like men. So where does that group me? Can I really judge my boyfriend if he enjoys making out with men when I partake in the same activities with my girl friends? Where is the line that I draw in which I say you're gay, you're straight, and you're bisexual?

In a world full of so many categories, definitions, and boxes that we all allocate to one another, are we limiting ourselves to "free play"?  (Thanks Derrida) The ability to think out of our social structures and realize that we are too complicated to fit into the confines in which we have set in place.