Great thread but where to begin?
I didn't really date in high school. I found myself very clumsy in the traditional role of dominant sexually aggressive testosterone oozing male. In college, things changed since I was able to develop relationships in a less stressful situation of getting to know girls in a "hanging out" environment where I would tend to find it easy to have female friends and develop intimacy leading to romantic involvement through "brain sex" followed by my romancing them in an almost tritely traditional way (dinner, wine, chocolate, candlelight, etc.) that was apparently a novel experience for college women in the late '70s.
My first serious girlfriend,with whom I'm still in love and always will be, and I spent most our free time together for nearly 2 years through college. We were pretty much every definition of soulmates, not a college infatuation. We were very intimate not overtly sexual. On occasion we would end up in bed cuddling but our encounters were limited to gentle kissing and nearly asexual caressing and touching. We never actually had genital sex. Eventually this increasing intimacy without progression to a fully sexual relationship caused the relationship to degenerate into a strange state of discomfort that mutually led us to end it. I tried to rekindle the relationship several times over the early years following college while we were both in graduate school (different ends of the country) but nothing ever became of my efforts. We drifted apart. I am pretty sure she ever married.
As I have mulled over the nature of our interactions and her personality, I strongly suspect she was lesbian. In retrospect, I wonder if our relationship might be best understood as a lesbian relationship where I had the inconvenient form of being anatomically male but the deeper connection between us cued in to my underlying feminine persona. This would explain much of the discomfort with intimacy that plagued us both.
I met my wife while in graduate school, another soulmate level relationship. We've been together for over 30 years now with a stable, generally happy marriage. To the point of the thread about roles changing over the years, I find there is more and more uncertainty I have about the sexual roles we play in our marriage. We are very familiar with one another's likes and dislikes and like most who have been married for an extended period of time, sex is very good if not somewhat predictable. Over the past few years, with kids out of the house and more time for introspection, my dysphoria has now come to the fore. Now, I find myself viewing the plumbing and mechanics of sex in a somewhat detached manner, as if the penis were a shared item between us giving us both pleasure. What's new, now I often fantasize about being the receptive partner. At an emotional or romantic level, I don't find myself attracted to men at this point but I can easily imagine having a heterosexual man as a sex partner only with me as a woman. I have no gay male urges whatsoever.
The problem is pretty obvious, I love my wife dearly, she would do just about anything for me but cannot provide this function. Her expectations are clear as well, wanting a traditional male husband for a lover. In practical terms, I can continue in this current state of bedroom affairs (no pun intended) probably indefinitely. Transition would change this dynamic--uncharted territory. With transition would I become functionally a heterosexual woman? Given my experience with this earlier probably psychodynamically lesbian relationship, would I become more bisexual?
Questions to ponder.