2:02 AM Disclaimer: Alcohol and possibly cannabis may be involved in the following post?
Although I'm working to be slightly more social in this online community, some may not be familiar with my "story" so to recap briefly, I dealt openly with my "transness" as a child growing up and by 15, my incredible parents had long since acknowledged that I never had been and never would be a boy. I started HRT at 17 and by the time that my "transition" was formalized right out of high school in 1973 when I was 18, I was able to blend into the woodwork as they used to say or in today's parlance, was fortunate enough to be "stealth". (I have to use all these quotes because it seems like I'm using language or concepts in order to be commonly understood and for convenience but they don't really feel like they fit or were never part of how I've described things.)
For the most part and pretty much exclusively, I've lived my entire adult life without people knowing that I wasn't born female. I have no family but certainly, I do have a small inner circle that knows of my history but anyone that has gotten to know me in the last 45 years or so would have a hard time believing it if I told them because I'm so thoroughly and completely accepted into the world as female even if by my trans brain's perception, I have some physical ambiguities. There's absolutely no reason in the world to tell anyone, even in the midst of a sexual relationship without some deep emotional or psychic connection that this was going to be a significant thing in my life or that this person had touched my heart and soul in some way.
Nobody has ever asked and it's something very deeply personal for me to share with someone and not something I'm in the practice of doing. I just don't like it when people know I wasn't exactly a girl as a child (but I was never really accepted as a boy either) and it's hard to explain. As an example, I had known my future husband for almost a year and had been having sex with him for two months before we had "the talk" so you can see the depth of how big of a deal sharing the trans part of my history is to me. I just don't do it in the real world. I'm a non-disclosurist!
The only real reason to tell anyone is this crap that rattles around in my brain and that's probably what is prompting me to sit down and write this?
There are three young women in my life I developed close friendships with. All look at me as a wise and caring person they can talk to, share their feelings with and they value my advice and opinion. I've turned to them as well and we've all cried with one another at some point. I'm seen as a trusted friend, big sister and as the cool kickass mom they wish they had and individually, I love all them just the way women do love each other and it's warm and physically affectionate and so uplifting, sustaining` and life giving. Even the dozens of guys I've gotten to know in the last year and a half seem to love me and some I've gotten to know well enough for them to open up to me too. All of these connections and bonds have become so rewarding and such a part of where the joy in my life is right now.
One of these women, I'll call her Karen, and I have become almost spiritually or psychically connected to in some ways and we just click? She's 23, forty years younger than me but wise and experienced beyond her years and is indeed an "old soul". We recognize each other's spirit and heart and see the world and life and people in so much the same way. We both see and connect with a lot of ourselves in each other and this has grown over the last year to where we really do love and care about one another (platonically). There's such an easy comfort between us. It's amazing and so pure and truly something beautiful but in the last month or so particularly, the thought of sharing my trans experience with her has been at the back of my mind and I don't know why? It would be a dumb thing to do.
We've talked about a lot of personal things and some of our deep feelings and emotions. We've shared our triumphs and our failures and our loves and heartbreaks and have opened up and been emotionally vulnerable to one another. We've also gossiped a lot too, have had hours of just girl talk and really respect the other as a valued friend and as someone to just enjoy being with. Many times, we just know what the other is thinking or can sense the other's mood and there's so much non-verbal communication between us, a quick glance or expression can say everything. I get her and she gets me and I cherish that immensely. When we share our cheek to cheek goodbye hugs, hold each other and say nice things, recently her friendly girl kisses or mother/daughterly pecks or whatever they are have been right on the lips and we always say I love you. We're both a bit on the queer side but this isn't that, at all. I have no interest in her romantically. It's just a natural warm bond between two women on the same wavelength that does seem to share a lot of the mother/daughter dynamic in some ways. My other two girl friends and even a couple of the boys are pretty open that they think of me as their second mom. (Keith is 39 and Jennifer is 36 and boy does that make me feel old!)

I feel close enough to my one special friend to share my tea but I don't know why or what would be gained by it? It would bring us closer and she would love me more, I'm sure of that but why would she ever need to know? What is even making me think about this when I would even have sex with someone or start a relationship and not say anything? (Don't judge)
It's not that I feel I'm being dishonest because I've never lied to her about anything. I don't have any made up stories to tell. Most of our childhood experiences and interests were similar. I was never socialized as a boy and we did the same kind of things, played the same way and I was a teenage girl once too so there's no legitimate or logical reason that I would even want her to know.
Part of me does though so why I am even thinking about telling her is the question I am asking myself? I feel it is a burden to tell someone and expect them not to tell anyone else because this is something that is hard not to talk about and as much as I know she does care about me and would never do anything to hurt me, I also know she's shared things with me about other people she wasn't supposed to and I can guess two people she'd share with immediately, her boyfriend and her best friend, both of which I also know and I really don't want that.
They say discretion is the better part of valor and I keep telling myself that and know no good will come of it but something in my heart wants her to know anyway. I've been wrestling with this for the last month and coyly mentioned to her tonight that there were things I wanted to talk about and she got it immediately that it was something important and personal so now she's probably going to bug me about it but I think that's what a part of me wanted anyway or I wouldn't have said anything? (Trying to self analyze here. I confuse the hell out of myself sometimes!)
I've spent a few nights sitting here and writing to myself about this trying to sort out my feelings and where my own head's at and why and have repeatedly come up with convincing arguments to just keep my damn mouth shut but yet again, here I spend another night having the same internal discussion with myself except this time, opening up the floor for comments because I can't seem to do the smart and noble thing and just let it go.
I understand my situation might be a bit different than a lot of folks here but for those that get where I'm coming from, how have you handled wanting to tell someone when all you can think of is good reasons not to? I'm pretty sure I won't ever actually tell her? I know I should just suck it up and get over it because it would make things simpler for her to not know. It's the part of me that does want her to know in spite of it being stupid that I can't figure out. Any ideas? Have other people dealt with something like this?
I know, probably "first world" problems not everyone can relate to. Please don't point out that being out and proud avoids situations like this but I'll live my life, you life yours. We all do what works the best for us. In this case though, I'm not yet sure what that is? Will logic and reason rule out or will what's in my heart speaking to me in a little voice? I don't know?
What say ye any that have managed to wade through this mess?