First Attempt at Roleplay Failed

I'm Sarah, in my early 40s, and I've recently started exploring DDLG with a friend who's into the dynamic. Our first attempt was supposed to be an exercise in trust and guidance, but it ended up feeling more like a painful reminder of my own insecurities. Trying to step into the role as an older figure felt both humbling and isolating. Despite our mutual consent, I couldn't quite shake off the feeling that I failed him as his guide. The experience left me questioning my ability to fully embrace this side of kink.