As far as hiding the tomgirlism and arguing with Barb, it started out that way. We know they argued about it quite a bit. Barb said stuff like "I didn't raise a daughter" and she also (for some bizarre reason) hypothesized to Chris that he might murder her because of it. I don't really get the connection between Chris turning into a woman and murder, but that's Barb, I guess. And of course, there was the time where Barb forcibly cut Chris' hair.
However, Chris stuck to his guns. He kept up the tomgirl shit (and now transgenderism/transvestism) and Barb gradually stopped complaining. She still doesn't like it, but she gave up pestering Chris about it. Now I'm pretty sure he does it openly in front of her.
Also, I just want to note: I wouldn't characterize Barb as having tight control over Chris' finances. Chris handles his own bills, he handles his own money. The big thing Barb does is that she can snatch money from Chris whenever she wants. I don't know how often she does this, but she probably does it to cover the electric bill or something.
Really, Chris has way more power in 14BC than he realizes.