I recently met this incredible girl, right from the start, there was a strong connection between us. She's genuinely kind, and we share a surprising amount of interests. However, there's something about myself I haven't shared with her. I’m a massive sissy. This is a big part of who I am, and figuring out the best time and way to share this with someone I'm dating has always been a challenge for me. My main worry is about how this revelation might affect our relationship or her view of me. I really like her and am hopeful about where things might go, but I also believe honesty is crucial in any relationship. Given that we're still early in the dating phase, I'm pondering if it's too soon or the right time to have this conversation.

She already knows that I’m a “feminine boy” and she thinks I’m hot, which is almost close to impossible to find women into someone like me, I asked her what her thoughts were about chastity cages and she didn’t understand so I explained to her in a very elegant and vanilla way on why I thought chastity is such a beautiful thing/dynamic and she said “I still don’t understand but I respect it”. I have the biggest hunch she’s going to leave when it all comes out and thats normal, girls always ghost me after I show them. Even my best friend left me (when I told her about my sissy and godess fantasies) after years of friendship hanging out with me fully crossdressed almost daily after work.

I usually break it to the girls I talk to after a month so they know what my personality is (I’m literally so cool) and it never works. Do I need to be on kink dating sites? Do I need to advertise myself as a sissy from the start? I’m already feminine in my day to day life but I must be doing something wrong trying to hide my chastity lifestyle in regular life. For those who've been in similar situations, how did you navigate this conversation, and what advice would you offer? (Please be kind as I am to others)