Hello Padma. Thanks for the reply. I suppose it was presumptuous of me to wrap myself in the transgender banner without doing more homework or giving more explanation. So, I guess I'll just press on with details on the source of my confusion for whoever wants to chime in.
In terms of gender identity, I certainly feel like a man. I've never had the slightest desire to be a woman or dress like a girl or play with dolls. (Though I don't mind playing Barbie's or House with my niece even when she assigns me the role of the girl—much to my family's horror). I'm a masculine looking guy—other than dainty hands and a big chest that as I age are becoming more like small breasts. I also have a voice that always has bounced around from deep resonance to effeminate. I also have suspicions that I have some internal female sexual organs.
My interests, however, are masculine. I am more attuned to male authors, for example. My viewpoints are imbued though with a strong feminine sensibility. I also have very poor mechanical aptitude and physical sense of direction, which fairly or not, are generally viewed as unmanly.
Sexually speaking, I am attracted to feminine women. Unfortunately, most women are not attracted to me. While there may be some initial physical attraction, they quickly get turned off. That could be entirely attributable to my lack of self-esteem and confidence, but I sense it goes deeper than that. I've lived most of my life in the rural Midwest and it's only been in the last few years where I've worked in a major city and done some international travel that I've really been more exposed to gay and lesbian people. They seem, in general, to have a stronger, more lasting attraction to and interest to me. Gay men seem to approach me quite often. A few have persistently tried to convince me to "give it a go." Sometimes I think I should try it once just to see if there is anything there, but while I can notice and acknowledge when a man is handsome, there just is zero heat behind it.
Having said that, I did have a sexual encounter with a former man. She told me it was the most at ease, enjoyable sexual experience she has ever had. I enjoyed it too; and it was one of the few times in my sexual life where I was a confident, effective, involved lover. It has also happened a few times with women who I knew or come to find are bi-sexual or lesbian. They have been escorts or strippers.
My experiences outside of that scenario have always been not good to disastrous. This could all go back to a self-esteem/confidence complex, but I have also had not good to disastrous experiences in paid sex. Basically, in the vast majority of my sexual experiences I am inept, clumsy, detached, self-conscious, shrinking and ineffectual. Always with straight women. My only positive sexual experiences have been with a former man and bi-sexual or lesbian women.
Another sexual paradox for me is that while I am passive and shy upon meeting women and have an inclination to defer to them socially, I am not interested in being sexually submissive. I prefer and enjoy more being the active giver and doer.
All these realizations have finally come together in my recent soul searching and processing of all my past experiences to try to come to terms with what is amiss. It's all very strange. I am not sure what to make of it. Again, I should not have jumped right on to the transgender bandwagon. It was insensitive to people who have struggled with gender transitioning, the desire or the dilemma of undertaking that. As agonizing and unhappy as my life has been, I have not had to face anything as difficult as that. Since I am not facing that dilemma, perhaps my presence is inappropriate for this forum. Please don't hesitate to tell me if that's the case. Thanks.