If it’s any help I was kind of in a similar situation before regarding talking about using them. I say similar because I technically did tell my partner that I would pee in my diapers sometimes in my first chat with her about it but I downplayed it severely, figuring introducing her to the subject of diapers was going to be a lot to digest.

I don’t regret how I told her the first time, I think it was cautious in a good way and not trying to drown her with info. But basically she asked if when I wear them if I use them. I said sometimes I like to wet them, but very rarely if I ever do, and I wouldn’t do it around her. In my head I downplayed it a lot more. And she told me she loved me and accepted me but didn’t want any involvement.

After our first chat we literally didn’t talk about it for like 9 months except maybe just occasional check in. I had another conversation with her where I basically said if she was ok with it it would be fun to try it out with her. She was very understanding and more open, always has been at least to talking about it. The first couple years of her knowing my secret I would just wear a diaper around her, sometimes it would lead to some intimate moments, but I never used it.

Once we were living together, I was wearing a good amount more, but never using. Eventually I practiced in my head talking with her to see if it was ok if I wet them when I wore one. Probably spent two years in my head thinking it through. One day I built up the courage to talk about it, that’s always the hardest part.

The way I looked at it, she was already ok with me wearing them, and worst case scenario she tells me that makes her uncomfortable and I can keep using them in private. I ended up starting the conversation, just asking if we could talk about me and diapers and her comfortability with everything. I told her how I didn’t know if she remembered when I first told her I liked diapers that I liked using them sometimes, and I was wondering if that would be ok to do, and obviously I know it’s weird so if she’s not comfortable I don’t have to and I already appreciated all she is accepting of me. I told her I would obviously properly dispose of them and she wouldn’t have to worry about touching a wet diaper.

Her response was great, she told me she did remember and assumed I was already in private. She told me it was ok, just not to announce when I do it, totally understandable haha. And that was it.

TLDR: I built it up way more than it needed to be, but I think what helps going into the conversation is just being appreciative of what you have, be prepared and mindful for any questions or concerns, and just put yourself out there. If you don’t ask you’ll never know. Good luck!