More dating quandaries

OK, here is another issue some of you may encounter. I am currently involved with a guy named "Bob", his sister is "Sarah". "Sarah" has a husband named "Gary". Read her first message at the bottom, then my reply
Here follows the email conversation....
Hello Sarah
Thank you so much for sharing with me, I feel like we are well on the way to really understanding each other and hopefully being good friends. I SOOO value a genetic woman's friendship and openness, it helps me in learning at least a tiny bit of what I was denied while growing up. Even though I was made to culturize as a male, I have always felt more kinship with other women. I feel so bad for my four sisters sometimes, because I understand and sympathize for the raw deal that women get in our culture. There were abuse issues of every sort for my sisters (and myself, but that's besides the point) while growing up. They have all four had a rough row to hoe.
I won't presume to say I know the depth of your struggle, but I can say I truly believe you in every aspect of what you say about it; I would never discount any of that. Rather, I am in awe of what you've accomplished despite it all, and proud to know someone of your strength and resilience. It's a very small percentage of people, male or female, who can overcome all of what you have.
I hope that you might read this straight through, though I know it is long. If you want the simple answer to your question about why I feel the need to 'advertise' my identity, then page through and look for the asterisks '*****'. The short answer is there. 'True Selves' will elucidate and back me up on this, which is why I so want you to read it.
There was a little girl once, who, despite everything she knew to the contrary, was forced to deny and subjugate herself, her very identity and essence, because she was born with the opposite genitalia from her mind. As she grew in this confused state, even her body rebelled against her mind and formed into the genetic male I physically became. Every Christmas, every birthday, every trip to the store for clothes, every day in school when the girls didn't want to play with me though I didn't want to play with the boys. Every time I looked in the mirror, absolutely everything was a denial of who I felt I was, such that I stopped believing it and pushed that identity to a very dark place I thought it could never escape from.
I don't think I was ever considered a very manly man, but I became convincing enough that I could function pretty well in this man's world (as much as women might want it to be different, it still is that way). I did some notable things in my 20 year military career, and enjoyed more than the average share of success.
That career and the family life I started was for a very long time, enough to distract me from my identity questions. But eventually, any career draws to a close. Mine did, and at that point, only my family life was left as distraction from the need to be myself. Both my parents were gone at this point, my father taken by cancer, my mother by foul play. My own mortality was becoming evident to me. I treasured my family greatly, coming from the similarly broken family life you did, I wanted that stable family life for myself and my child that I was denied. Had that family also lasted, I might never have pursued transition.
But at some point, my wife's sexuality struggles became too much for her and she declared the need to leave me and pursue a life being with women. I cannot deny culpability in this, my identity struggle was making me so miserable, I was climbing into a bottle to escape it and making others around me miserable. At any rate, it was only after this happened that I pursued transition.
It might seem a blessing, that I could grow up with white male privilege. And I understand how some women might feel I am an interloper, now 'infiltrating' the life of a woman. I won't deny there were indeed some compensations in growing up male. But all my successes were empty to me, I never felt they were 'mine'.
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'Cisgendered' is the label used to define people who have a homogenous gender identity and biological sex. A cisgendered woman feels like a woman, and has the body of a woman; the male bodied cisgender identifies as male.
The most common mistake among cisgendered people is to fail to separate gender identity from sexuality (I'm sorry Sarah, but nearly the first words you said here did just that when you pegged this as a sexuality issue!). Therefore, it becomes easy for the cisgendered to assume that a transgender person should be able to 'hide' their being transgender just as a homosexual person can hide their sexuality. If one can ignore the stereotyping of gay and lesbian people, you know that a person's sexuality is invisible, a woman who is lesbian does not 'look' inherently different from a straight woman.
The issue here is identity, not sexuality! If you read straight through this letter (or if you go back now and do so) you will see that at every turn, identity, not sexuality, is the 'issue' for me.
According to most people I meet, I "pass"; in other words, I look like a woman to most everyone around me. I don't know if you believe this, I don't believe I do "pass", but for the arguments sake I will concede that I do, and Gary, for example, will not question I am simply a woman.
Perhaps, by virtue of my favorable genetics, people believe I am simply a woman (again, I don't believe everyone sees this). This is gratifying, but if I identify as truly a woman to people I meet, I am lying. I am hiding my identity, past and present, from others. My sexuality is nobody's business but my own, and certainly doesn't need to be advertised. But my identity is not the same thing. If I am asked, "What did you do in the past for work"?, sure, I could play off that I was in the military for 20 years as a woman (again, a lie, but let's just play along with society here, right?) The next question is commonly, "Did you and your husband have children"? I could lie here for conversations sake to bypass the issue, but would YOU deny your own children's existence? The next question is commonly, "How old is your son and/or where does he live"? My son lives in San Diego with his mother..........
Lie after lie is compounded, almost instantly. I'm not being asked to simply hide who I go to bed with, I'm being asked to hide who I am. I just got done NOT hiding that I am female, should I now hide that I WAS male?
Alone by myself, I could go out to social events and be approached by men who see me as a woman. Again, it's gratifying, but let's face it, men are not particularly discriminating, are they?!! lol! "oh gee, look at the tits, yep, must be a girl!"
I could let that go, and say yes, I am a woman. Then I go out with the guy, who has proclaimed to all his buddies that he is "going out with the hottie by the pool table"!
If he and all his friends believe this, then he and I go out and perhaps some petting begins to happen. If I have really 'fooled' him this far (the standard accusation for those girls like me who have failed to "ADVERTISE" who they are), by now he finds out I have a penis. That's how girls like me end up dragged on a chain behind some stupid homophobic redneck's pick-up truck.....
All of what I have said can be dismissed as fervor rhetoric by an interested party. Perhaps it is, but it is nonetheless the truth.
So let's say we go out on our motorcycle outing this coming weekend, and Bob and I take a spill. Knocked unconscious, with my clothes ripped off my body during the spill, you and Gary come back to help. What then?
Granted, as an exact example this is an unlikely scenario. But it doesn't take much imagination to see the lesser circumstances where this might surface anyhow. If I play along with those who want me to simply be silent, I am then disclosed as a liar and pervert when others find out...... all my fault. I could live with this, I already knew that my label at that point would put me at fault. What do you want to do with the fact you already knew? What then, does Bob do ?
If you did so, thank you for reading all of this.
M
Subject: Just a question about something
Hello there,
I know that the struggles you have with your particular sexuality issues have made life pretty different for you both. God knows that I should be more screwed up than I am considering the background. I guess I am different and cope differently. I was doing some pretty crazy and destructive sexual things but I think that *** really did wake me up. I wanted more for him and realized that if I did not fight for him he would end up in a bad place. So I chose conservatism in life and stability over everything to change things for myself and my children.
Here is my question. I really do not discuss things of a sexual nature with everyone because it really is not anyone’s business but mine. I have been really open about sex with my kids because I did not want any teenage parents or dead people due to transmitted diseases. So far so good with that. They can come to me with problems [like *** had recently] and tell me anything and I do not judge or shun them.
When you are transgender, why do you feel that everyone needs to know every little thing? Also, another subject I have been mulling over….. If Marie is going to eventually have her operation and fully change gender, why would you look back and need to let people know about any change. I am not saying it is anything to hide, please do not misunderstand me…… I just do not understand the compulsion for everyone to know every detail of your private life.
I hope you do not take this the wrong way. I just don’t understand it.
Gary has been won over by the great person Bob is and he sees that he has lived on his own and is a stronger person. He respects that and loves Bob for the great guy he is. He trusts the person and he also can see the close relationship we have. That is the way Gary is and it will not change.
So, what is wrong with leaving well enough alone and just looking ahead? When I was in counseling the person told me that some things are just better left alone. I was so mad at Mom for so long for being weak. Guess what? If you want a relationship with a weaker person you have to make it work and shield them from things they are not equipped emotionally to hear about. Mom still does not acknowledge my years of drug abuse and crazy living. It never happened in her little world. So is it wrong to shelter this person? She had a sick [tuberculosis bedridden for lots of her childhood] mother who died when she was 12, lived with an alcoholic father off and on, and most of the time with whatever relative would have them. She then married our father who was overbearing and often just mean to her. She did the best she could.
Anyway, I am so thinking of this stuff all the time that it is waking me up at night. So, think about this and let me know your opinion. I am open to everything but that is because I am really beyond being shocked. I have pretty much seen it all……. Sadly. I want to have a perfect little life in my next life. Ha ha. This life has been good but the hard stuff is so hard. I could go for the mindless life with no trouble and everyone in my life being happy all the time. Is there such a thing?
Oh well, I will sleep better now that I have unloaded some of that. Now it’s your turn….. Sorry. Love and hugs to you both.
Sarah