After almost 35 years I've finally started to come out previously in order the only folks who knew I crossdressed or ever thought about becoming a woman was my jr high counselor she only knew the cd side of myself, 2 female and 1 male friend in a mmorpg I play those 3 know i'm seriously considering transitioning and that I do identify as transgender they were told almost 2 months ago, my current therapist I started seeing her a moth ago and discussions do occupy at least 15-20 min of every session were going though my life one stage at a time right now she wants to hear about my time in the service. And as of 2 hours ago my little brother now knows tell him was hard really hard it took me a few minutes to compose myself and say something after I dragged him aside but wow what a relief. Since I live with him and his fiancee he was bond to notice my forms on at some point or the dresser draw slowing filling up with womans clothing, or my painted toenails, or the woman's underwear hanging up in apartment drying. Next is his fiancee and that's happening tonight my little sister next time I see her alone and a close friend of mine with one or more of her daughters tonight or tomorrow. My folks/grandparents are gonna be the hardest i'm 100% sure my mother will be ok prob 75% sure my grandparents will be ok but 100% sure my father and I will have a major fight and pretty sure i'm gonna get disowned by him. Hes always shown me to be a homophobe from the day he caught me mastubating and made a comment asking me "what are you gay" to the ->-bleeped-<-storm that happened when my former brother in law became my former sister in law and also a few times a trans woman that stood out a bit passed by us when he ran a photo business up at loudon nh speedway. I still hold hope for him and me but im 100% prepared to walk away from him forever we've never gotten along to start with. My folks will be told separately with my father only if the following condition is met i've been on hormones for a few month now and the changes to my body can no longer be hidden.
At this time the only thing I know is i want to transition but what I don't know for sure is it right for me i'm discussing it with my therapist every week and i'm gonna go off her judgement I do know when i'm dress or well underdressed I only own a few sets of bras/panties atm + nail polish i'm a totally different person i'm happy I feel good i'm more motivated to do something I play my games less and do things around the house more or go for walks altho to date there has only been 2 occasions ive gone anywhere with my forms yesterday I went to a store with my forms and a big winter jacket zipped up and last week to my therapist's office with plans to do that again tomorrow. I plan more excursions like these but only as long as I can hide em there only b cups so they do hide well but only under some of my jackets.
Wish me luck I grew up in a fairly religious roman catholic family but so far so good all my brother said really was do what makes you happy and Ill still love you even if you do become Rylie and a sister to me.
Edit: Now both my friend and brothers fiancee knows full disclosure and best thing is both were very supportive! :)
Edit 2: And now my sister knows with a few surprises shes always apparently thought i was maybee trans and she admitted she at times has felt wrong in her body to but she does say its not bad and most of the times shes happy as a woman.