Off the top, I want people to know that I am not looking for solutions. There is a case of cans-of-worms, several dichotomies, double-binds and a couple Gordian Knots here. This is mostly a case of me writing to arrange my own thoughts, and putting it here for two lesser reasons. It might help somebody get some insight into their own situation, and some different perspectives, if offered, might be useful to me.
I am 50, MTF, only attracted to females. I am non-op for financial reasons for sure, and probably even if I could afford it; the risk/reward ratio seems negative. I am living with a woman, my age, for 5 months now. We have alot in common, we get along great, are very much in love, and sex is incredible. So I have no right to bitch about anything.
On the other hand, we have some particular problems:
1) Her sexuality. She is not and has never been attracted to women. She does not want to be identified as a lesbian. She does not seem to understand that she can be in a lesbian relationship without generally being attracted to women. We know two lesbian couples, where everybody was married to a man at some point, never was in a relationship with any other woman than her partner, and is not much attracted to other women. But she doesn't see that as similar to us. To some extent, she has a cognitive-dissonance problem, to whit: I am not attracted to women, I am attracted to Gina; therefore Gina cannot be a woman. On the other hand, she very much likes the feminine aspects of my body, and my sexuality. She prefers my smooth soft skin to her recallection of male skin, loves prolonged foreplay, and likes boob-on-boob action as much as I do, which is a real lot.
2) Our sex-life. For most of my life, and 100% of the time for the last 20 years; when I have sex, in my mind, I am a woman. Even if I am having intercourse, in my mind, one of three things is happening. I am imagining I am using a strap-on for my partner's pleasure and eventually climax from clitty-bumping, we are using a double-dildo, or there is no penetration at all, just dry-humping and boob-on-boob action. I have told her this. She seems to understand. She doesn't quite believe it, and she doesn't really like it. On the other hand, what I do works for her. She acknowledges that, by a long-shot, she is having the best sex she has ever had, and is happier than she has ever been.
3) My imaginary sex life. I have been involved, for ten years, in some medium-kinky online roleplay. I am one of the acknowledged leaders and a VIP in this roleplay realm. When my life was crap, roleplay was my life. I lived in VT, and RT was just what I did to pay the bills to make VT possible. But now that I have a real life, I barely care about VT. I have little desire to roleplay at all, no desire for sexual roleplay, and genuinely feel it would be cheating to even risk getting into roleplay that could lead to my character getting captured or raped. This is public knowledge in my realm because I posted about it. I still have a leadership role, but only in an advisory capacity. I still have close friends there, that I want to maintain ties with, including friends I feel closer to than anybody I actually know in RT. It can become easy to share your truest self with somebody you know you will never actually meet. However, my GF is so square that her idea of computer gaming is that she has all the Sims games. Involved roleplay, like I did, is so far out of her realm of experience as to make being with a ->-bleeped-<- seem almost normal. She is jealous, she thinks I will go back to roleplay when our sex gets stale, she doesn't understand that I am genuinely friends with people there, and she is always suspicious that I am sneaking into roleplay when I am on the comp late at night. And she is adamant! that she doesn't want to be the RT body substitute for some VT-based fantasy, which I wouldn't do anyway; but she is all paranoid about it.
4) Her family. Her mother refuses to use appropriate gender references to my face, much less on the phone with my GF or other family members. Her mom says, "If he is a woman, that makes you a lesbian, and I won't have no lesbian daughter." My GF's daughter brought my GF's granddaughter to visit her twice since we have been together; both times at the store where my GF works. I don't think the eight year-old granddaughter knows about me at all. The daughter and granddaughter didn't attend Thanksgiving. At Thanksgiving, everybody dodged gender references pretty well, but the five gender references that were used were all wrong (Mom-2, Sister-2, Son-1, and nobody seemed to notice; which implies that they are all using male gender references when discussing me in my absence. I think they all view me pretty much as just a slightly weird guy, not really worse than some of the other guys she has been with; and better than most.
5) Passing. I totally pass. I am frequently called beautiful, and my GF says so, and says that (even though she is pretty and knows it) I am better looking (as a woman) than she is. On the other hand, she thinks everybody reads me - and half the people who read me want to kill me. In reality, the only time I ever have issues are when straight guys are checking me out (with the intention of hitting on me) and then get offended that I made them have (what they perceive to be) gay desires. My GF also has serious Ladies Room issues. She acknowledges that I should use the ladies, I must use the ladies, and am legally entitled to use the ladies. But she won't go in with me and act normal about it.