This topic is perfect for me in that it deals with where I am and what I'm coming to terms with.
My mother left my dad when I was 4 because as my dad put it, she did not want me to grow up to be an all American boy, whatever that mean. She made sure that he did not have much contact with me and we never got all that close.
Mom and I went to live with her mom in a huge 2 story house in which we lived upstairs. I remember the 5th grade when I hit puberty at age 10, saw my first Playboy magazine and started really noticing mom's breasts particularly when she went around the house with pants and a top on but no bra. Long story short, she took advantage of my noticing her breasts and one thing led to another.
Mom really did not want a son which she told me and I got the message for when she got mad she would dress me up in girl's panties. When she got really angry, she would make me wear a bra that she stuffed with left over cotton that came from her mother's cotton farm.
The next year, my mom married a man whom I never bounded with and whose son led me into male oral sex. Mom continued her very strong attachment to me. I told her near the end of high school one day shouting "look you are married now, let go of me!" Basically, she married my step-dad to get out of that small town.
All of this contributed to being so anxious around women that I didn't date in high school, college or in graduate school. However, I look at all sorts of porn, when to topless and strip clubs, and some massage parlors. I felt the need to tell mom what I was doing and she thought all of that was fine and said if I ever needed some extra cash for such entertainment that she would give me some.
In my early thirties, I met and married the first and only woman that I ever felt comfortable with. Several years later, I randomly mentioned on the phone that I had found looking at muscular nude men to be very enjoyable. Her only reply was to say, that's fine if that makes you happy.
It was not long before I bought my wife a realistic vibrator, but really, I bought it for me. We enjoyed it together on the anniversary that I bought it for. She was comfortable with that which was good. The next anniversary, I bought her a dildo with strap for she had told me beforehand that she once told a therapist that she wanted a certain male part.
My wife and enjoyed that orally on our anniversary. After some time though, she said that she was wondering if I wished she has a real male part. I told her no, but that was not really the truth. She told me that I could suck all of the vibrators and dildos that I wanted to as long as I did not suck the real thing.
I was finding shemale porn and bisexual porn more and more of a turn on as this part of my sexuality came more and more to the surface. As it did, I told my therapist that I sometimes wished that I was a girl with big breasts and ordered some fake ones for me which I didn't keep too long and my wife never knew about.
I think that I understand how I got here, but I'm not so sure that I'm entirely comfortable with where I am.
I've tried to write this as compact yet complete as I could without going into extreme detail. I look forward to hearing someone reply to all of this.