First case that comes to mind is Chastity/Chaz Bono.

And if your mom was Cher, you, too, might decide to choose to reject womanhood rather than dress up in Bob Mackie wear

Chastity Bono is a really sad case. My aunt was acquainted with her because they ran in the same lesbian circles back in the days before all lesbian communities & bars got turned into generic qweer spaces. My Aunt was so disappointed when Chastity transitioned. According to her, Chastity took it REALLY hard when her father died. And constantly being compared to Cher and seeing people joke about how fat and frumpy she was compared to her glamorous mother took a huge toll.

It makes sense to me because, ever since Chastity "became a man", nobody shits on her for being fat or not being as pretty as Cher

R Kelly has a lesbian daughter who went through an FTM phase for awhile. She said she got depressed while ID'ing as a man, and that she's happier now. I feel for her, having a dad like him.