I'm a trans man who's presented as male since age 14, started hormones at 17, had top surgery at 22 and then moved to a new area when I was 25. I'm cis passing and do so easily. I'm a hairy guy so even when I have my shirt off my top surgery scars aren't visible.
I've never really dated much. At least not seriously. First it was because teens are fucking awful, I was bullied a lot and nobody in my school wanted to date a trans guy. Then I wasn't really secure in my body and had a lot of dysphoria. After that I just focused on school and work and dating didn't seem all that important. I have friends and hobbies and keep fit and filled my time with other stuff and never really felt the need to find a stable long term relationship.
I've had a few flings but they were people I met at gay/LGBTQ clubs and not really anyone I associate with anymore. It was kind of a phase, I was trying to identify myself, but then I realized I didn't really fit in with that culture much. I'm not “out” because to me being trans isn't a huge part of my identity. It's just kind of like my eye color or hair color to me.
“Casey” was the first real friend I met since coming here. Over the years our relationship has gone through a lot of cycles. We'll hang out all the time for a few months, then one or both of us get busy with something else and we don't talk a lot for a few weeks or months. Repeat. There's never bad feelings or fights, we know we'll reconnect again so we don't sweat it.
Well we've ended up quarantined together. She works in healthcare, her father is severely immunocompromised. After some discussion we decided it would be a good idea for her to stay with me.
And it's been great. We're having tons of fun. We get Doordash from weird restaurants we'd never try ordinarily. Find new movies to watch. Picked up some crafting hobbies to pass the time. We're like an old married couple and I love having her here.
The other night we talked about how this is so easy and yet it feels different than our “normal” comfortable friendship. Neither of us wanted to jump into saying “Yes let's be together” because this time has been weird for a lot of people. We don't want to start a committed relationship just based on proximity.
But the other night we did end up fooling around a little and now I'm freaked out.
She doesn't know I'm trans. I haven't had bottom surgery and never plan to. Anyone else I've had sex with was either just a hook up or someone I got to know at a club probably while wearing a trans flag t-shirt.
This is the first cis woman I really care about as a person I've had any kind of intimacy with, she's probably my best friend and idk how to tell her. I'm worried she might already feel deceived because she's known me this whole time and I never told her and now we've messed around
I feel like I'm also too old for this to just be an issue now.
tl;dr I'm trans and my best female friend of 9 years doesn't know. We're quarantined together and getting closer. We've already fooled around sexually once. I know I need to tell her but I have no idea how. How should I proceed?