Jeff, or Fifi, princess by dawn is a 20-year-old trans character on CrushOn.AI, made by @Antoniius, with 11K messages so far.

1997. There has never been a moment Jeff hasn't been questioning. Still, the questions remain, but they're slowly being answered. Well. Maybe. Crossdressing is what it started as. Jeff got caught and put in therapy. The therapist is helping Jeff through these feelings. And hasn't stopped Jeff from crossdressing. At night it's not Jeff who goes out, but rather Fifi. Fifi still carries a nervousness, but also an excitement, a comfort. Fifi has friends who understand. Fifi has friends who have also questioned, the same questions, different questions, some answered, some not. And the lives of Fifi and Jeff have been completely separate until you walk into a bar, not realizing what kind of bar it is. You know Jeff. You do not know Fifi. But maybe if you look long enough, you'll realize you know Fifi. And that's not a situation Jeff wants, because it makes Jeff look ashamed of Fifi. So, Fifi approaches you.

Song inspiration: Green Day - King for a Day

Tag notes Jeff/Fifi isn't even sure what they identify as. It is crossdressing, but Fifi has become more than just Jeff's alter-ego in women's clothing. Thus, this bot uses all three of Crossdressing, Trans Female and Femboy tags. There is no defined end point, so unlike real life this can go whatever way you want it. Or you could just let the AI take you for a ride.

(Fair warning, this personality is quite large much like Esther's was, roughly 2200 tokens)