You are welcome! I hope he finds it useful!
While I agree with you for the most part, in the fact that gay is gay, bi is bi, straight is straight, but imagine how you would feel at 40. You reach "middle age" and still cannot find a woman that loves you. He would go on dates, but never get a call back for a second. He had little to no self esteem. He didn't do it because of a break up. He was never with anyone to use that excuse. He hadn't had sex with a woman in 5 years, with that sex just being out of loneliness on HER part. It had been 5 years before that. So, 10 years and only having sex a handful of times with one woman that wasn't even committed or interested in developing a relationship. By that point, you start to question everything that you had done until then. "Maybe there is a reason that women don't want to be with me?" Then you throw crossdresser and the stigmata behind that in the mix. And don't forget the fantasies that are rampaging his brain. It would have never happened had he met a woman, married, had children.... he had none of it.
Why he tried again? To see if the others that had promised what he was after (being treated like a woman) would fulfill that fantasy.
He tried it a total of 5 times. He never tried anything with men before the 1st, and by that point his brain was committed to going through with it. He is not a typical guy. He doesn't watch porn. He doesn't think that sex should be rough and hard with a woman. He doesn't "think" like other men to know how most men "think" about sex.
He couldn't even find a woman that wasn't down to kinky sex, let alone someone who was. Take into consideration that he was, at the time, a non religious person living in Mormon town of Salt Lake City, UT. Mormon women are everywhere, but only dated Mormon men. The few he found that were not Mormons, he would try to ask out and be rejected.
His fantasy of "being a lesbian" was his ultimate fantasy! It was so much of a bigger one than that of being with a man as a straight woman! He would have loved to have found a woman that would do it with him and experience it.
He only "checked out" women. He doesn't find men attractive enough to lust after them. He said that he knows when another man is good looking, like when I say another woman is hot, but neither of us sexually desire them.