Originally Posted by
asiafever
Firstly to clarify my position I'm all for it, if all parties involved are happy then really I don't care what persuasion someone is, I've been a groomsman at a gay wedding and one of my oldest friends is in a relationship with a ts. I'm terminally straight, though I've seen pics of ts that I've thought "She is sexy" but I have no interest in a sword fight.
Your situation is unique in that here you have the management of a very hetero place, so he may feel he has a reputation to protect, and there may be cultural obstacles to overcome also. I would suggest to tread carefully, really suss out the lay of the land before proceeding too far. Even bringing something up in passing like "Hey, have you had many gay guys coming in to try a girl to see if they like it?" Or something similar to bring the topic up. If he goes full homophobe then you have an immediate answer and not to waste your time, if it then leads to a more positive conversation you can press further, ask about ts, bi guys etc, eventually try and work around to what his preferences are.
I mean of course you could just go "Hey Tim, listen, I'm not sure if you knew but I'm bi and find you attractive, would you be interested?"
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