I am not sure I can explain this well, but here’s a stab at it.
Straight men, unless a person of color or other minority, typically do not face discrimination. The world is designed around them and the rest of us work it out as best we can.
A straight man who gets off playing dress up and who likes to do this around lesbians is entitled to that fantasy, but he doesn’t have to involve real people in THEIR environment for his sexual pleasure.
Folks are certainly entitled to live out whatever fetish they choose until it crosses over the line and starts to impact other people without their agreement or consent.
As some lesbians have a laundry list of issues about sex with men and the power inequities that often cause those issues, the notion of a straight man thinking that he has the right to live out his sexual fantasy in front of or with a group of lesbians is inherently problematic for me.
In this instance, a friend of the person is asking the question. I have no sense of the character or intentions of the person doing it because it has gone through his friend’s filter first. I can only respond to the question on its face.
Some will say imitation is flattery, but there is a fine line and, from the description in the question, an easy line to step over. There are likely a number of lesbian bars where he would be laughed at or treated with derision, others where he wouldn’t even be noticed and still others where he could get his clock cleaned.
It depends on where he goes and how he behaves as to how the experience might turn out. I am more interested in discussing the fundamental underlying reason why his experience may go poorly in deference to my fellow lesbians who have suffered from childhood sexual abuse, rape, and other very real and very unpleasant experiences. For him, this is a fun little game; he can’t assume his “audience” feels the same way.
One person should not have to pay the price for another’s fun. To deliberately seek an environment where folks have segregated themselves away from people like you, to dress up (either for sexual gratification, to pretend to be one of “them,” or both) is an assertion of the very sense of privilege I am trying to describe.
This is also entirely different from a gay man in drag, or a young man who is trying to sort out his sexual identity. You can have three or four different men wearing women’s clothes and walking into a lesbian bar and the women will quickly sort out if he is a threat or not. Of the potential combinations, the straight man who is doing it for his sexual pleasure and including the typical bar patrons in his fantasy, is the most troubling. Halloween is probably the only time I can think of where it would be viewed most consistently as a costume and might not rise to the level of being a threat.