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Originally Posted by Skeezyks
Hello Keyplayer: Well... I don't know how old you are.  I'm pushing 70!  I guess I've been trans (MtF) my whole life, although I really didn't understand what it was all about until just a few years ago. (I'm still not sure if I really qualify.) Up to that point I just thought... well... actually I guess I really didn't put much thought into it. I just assumed I was the only person in the world who was afflicted with some kind of disgusting compulsion.  And I just went on living a relatively normal male life on the outside while doing all of the things closeted transgender individuals do in secret.  I never transitioned & I never will although even at my advanced age, it still haunts me. (If you're truly trans, you're trans for life. It never goes away... as I have heard it phrased.)
The only people who know anything about my situation are my psychiatrist & a former therapist I saw for a few months several years ago. Oh & then there's my wife. How she found out was I left her a note with a link to a YouTube video & then proceeded to try to kill myself for the second time.  I woke up in the hospital a day or two later.  We don't talk about it though. We have sort-of a "don't ask / don't tell" policy I guess you might say...
Anyway.... I don't really know how you find the courage to tell someone you may or may not be close to you're transgender.  Obviously, I don't have much experience with it. I presume it's a matter of practice makes perfect. Start with a person you feel the most comfortable with whom you think is likely to be supportive & tell that individual. Then begin moving "up the ladder", so to speak. The more you do it, the more self-confidence you'll build. Over the past few years I've watched a lot of videos on YouTube on the topic of gender transition. And it seems people generally find that it goes much better than they would ever have imagined. 
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Skeez, your emoticons are genius. What an emotional story. And a heartbreaking illustration of what can happen if people are not allowed to be themselves.
I'm glad you came through it and are here to tell the tale.