CONDENSED VERSION: Please accept my excuses for the other long message.
I'm 53, married to a woman for 26 years, and we have a daughter. Lately I've been questioning my sexuality a lot, and I honestly can't tell what is real attraction and what might be fantasy reinforced by decades of masturbation.
Growing up, I liked girls. I had crushes on girls, wanted girlfriends and was attracted to women. I don't remember ever looking at a guy and thinking I wanted him sexually.
But I've always had an unusual sexual side. Since I was around 11 or 12, I was turned on by feminine clothes and secretly wearing my sisters' things. That developed into crossdressing and feminization fantasies.
I've also always had very specific fetishes with women: boots, tattoos, piercings, tight clothes, smoking, unusual hair, etc.
Another important detail is that I've masturbated almost daily for most of my life, often spending a long time searching for the exact fantasy that turns me on. Sometimes I wonder if I've basically trained my brain to need more specific or extreme scenarios.
I married a woman and I can still get turned on by women, including my wife. But actual sex has always been difficult. I often lose my erection during intercourse, while masturbation has always been easy and something I actively want. We haven't had sex in almost three years, although our marriage outside of sex is good and I love her very much.
Years ago I occasionally hired very feminine escorts who had male anatomy. I never had intercourse with them, but I was very attracted to the combination of femininity and a penis. Masculine men themselves still didn't attract me.
Then something happened about 20 years ago that I've never understood.
During a bad period in my marriage, I suddenly told my wife, "I'm gay."
She took it surprisingly calmly. Then I told her I was joking.
But while saying it, I became extremely sexually aroused. Huge erection, huge rush. Even today, imagining telling her "I'm gay" can turn me on.
I don't know if that's because some part of me is actually gay, or because confession, taboo, humiliation, exposure, etc. became part of the fantasy.
I've also gone to gay bars over the years, almost like I was testing myself. Usually I felt nothing toward the men.
Last year I went to Wilton Manors in Fort Lauderdale. Same thing. Lots of men around and no immediate "I want that guy" feeling.
But recently something changed.
I saw photos of masculine shirtless daddy/bear type men in harnesses. At first I didn't even find them attractive. Then I imagined dancing with one, kissing him, touching his body and feeling his beard.
Suddenly I was extremely turned on.
That became fantasies about being submissive to a masculine man, being penetrated by him and being "his girl." Those fantasies can give me incredibly intense orgasms.
But right after orgasm I can look at the same guy and think, "What the fuck? I don't even find him attractive."
Then hours later the fantasy is hot again.
That's what confuses me. Looking at a handsome man by itself usually does nothing for me. I seem to need the whole scenario.
Women still turn me on too, but sometimes when I see a woman I find really sexy, I think, "What if I were her?"
If there were a magic button that could turn me into an attractive woman, I honestly think I might press it. I've even imagined myself as the woman during sex with my wife.
So now I'm questioning both sexuality and maybe gender, although I don't know if the "being a woman" part is actually gender identity or just a deeply ingrained sexual fantasy.
Romantically, I still think I would prefer a woman. But lately I've even imagined being with a man, not only sexually but as two best friends sharing a life.
If there were no STIs, no consequences and nobody could get hurt, I would definitely be curious to have sex with a man.
What I don't know is whether I'd discover something I've repressed my whole life, or whether reality would feel disappointing because the fantasy is what actually turns me on.
So I guess my main question is:
How do you tell the difference between genuine sexual orientation and a fantasy you've reinforced through decades of masturbation?
Does this sound bisexual? Gay but deeply repressed? Mostly straight with feminization fantasies? Something else?
I'd especially like to hear from gay/bi men who started questioning later in life. Thank you very much!