Wow, such moving stories, omigosh..
Umm, well, the question was who was the most difficult person to tell, but first let me say that because I was a genetic female mis-gendered due to medical nonsense, I knew that my family couldn't really say squat about it, no matter if they were trans-phobes or homo-phobes. It was a fact, and they could deal with it, or not. I called each of my siblings, except the rapist, and broke the news. Starting with the two that knew me best, and they cried, and were onboard immediately. A year later, I told my fundamentalist religion believing sibling, and it went fine, too, and she was mad that I had delayed telling her, but my other sibs had warned me off, saying she would be judgmental. She was not, and we have become tighter than any two sisters ever could be, and she was the fastest to get my pronouns right, and to socialize with me without referencing who I used to be. Lesson learned!
But, again, the question was, who was the hardest person to tell?
It wasn't my spouse, lol, she already had a notion I was 'different', ha!
It was the manager of the apartment complex I had been living in for the last several years. See, he oversaw the whole male maintenance crew, and they all saw me as top dog in the complex. I knew that whatever I said about medical history, it would just sound like trans/gay stuff to the crew, and I did not want to get into my mutilated parts, or the DES exposure, and all that stuff with them, most barely made it out of high school. So, I knew my safety was going to become an issue, so the day I went full-time, I marched into the same office that 'alpha dude' had walked into several times a month, for years, in a skimpy blouse, bra, short skirt, make-up, and flip flops, and speaking with my one of best little girl alter's voice, and "I" explained it all to him, as he sat there, jaw on the floor, as the office girls watched from their desks, with eyes popping out, but "I" kept my cool, and told the whole story...
I had to tell it all over again a few times before the 'non-trans/non-gay' part of my story sunk in, but once it did, I was home free, and sitting at the pool in my bikini, and a LOT of the beta males were very nice and friendly afterward. Had to work it out with the sub-alphas, but my 'protector' alters were pretty convincing that there would be no crap taken from anybody, and though I hate to say it, fear of what they figured I might do kept things cool..
Yeah, funny how things work out, huh?
Missy