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(+2)(-1)

is there a transgirl dating option?

(+3)

Gabby was probably designed the closest to that in that she can have a dick, though maybe not exactly what you were hoping for.

In the PC Feminization storyline with Chloe you can get her to have a dick later in the story, as well.

Besides that, I guess there hasn't been a traditional transgirl character option, so it might be a good idea for a character in the third town.

(+1)

would be amazing if u decide to have one, ill keep my fingers crossed. what about futanari?

(+2)

Basically the same answer, I think Gabby would fit what you are looking for. You can start building a relationship with her after you bring her the trinket from the park, which will give her a dick.