Came out a little to my mom finally.
So if you feel like searching threads, you can read about how I shared with my mother in law in 2017 that I wore panties and the occasional bra. Ended up being no big deal, actually worked out well, as we have actually gone shopping together a couple times. Well, I assumed I could never have this same conversation with my mom, but on the phone today we discussed her weight loss and how to handle it. She mentioned she was visiting my brother and had some jeans she'd found, wanted to know my size. I paused, and told her I hadn't worn many means jeans since my heart surgery, explained that the vein taken out of my leg had made them uncomfortable, and I preferred an elastic style jean. I told her I made the switch to mostly women's jeans. She paused and asked what size, I told her 22 or 24 depending on brand. I told her I didn't want her to be surprised if I had any medical issues come up, so my mother in law had already been told since we live closer to her. I then told her I had switched to women's underwear because of the vein issue. I expected a laugh or "WHAT??!" but she said, "well, you have to do what works.... you're not wearing bras are you?" (She knew it had been recommended by my surgeon after the insurance refused to pay for the chest support recommended to provide support after my heart surgery). I told her yes, I did, but rarely, only when doing a fair amount of heavy lifting. She laughed and said she was kidding, but it actually made sense. Then she said something I never expected to come out of her mouth...."You know, it's crazy how women can wear men's clothes and no one cares, but men can't wear women's clothes without it being a problem." I was shocked... but happy I was finally able to get it out in the open and it doesn't seem to be a problem.