This actually ties really heavily into something that's been rattling around in my head for a while about Chris. Occasionally, people will ask if Chris is really trans, or if this is just a ploy to get women. (Because that makes sense, right?) Marvin has repeatedly pointed out that Chris is fully invested in the trans thing. Here's why I think he is:
As HumanBeanbag pointed out, Chris' ideas on gender roles are firmly stuck in the 1950s. In Chris' world, men are supposed to be rough and tough providers, and women are supposed to be gentle and kind caregivers. (Who are in turn cared for by men.)
Based on this view, Chris is, obviously, a complete failure as a man. He's not tough. He's not a provider. His parents have cared for him his entire life. And in Chris' view, being a man is hard. You have to go to work, and we all know how Chris feels about work.
But on the flipside, in Chris' world, being a woman is easy. Based on Sonichu, according to Chris, all a woman has to do is go shopping, cook, and be there for some loving when the man wants it. Oh, and maybe take care of some kids, but how hard could that be? (Spoiler alert: It's really, really hard, but Chris doesn't know that.)
My theory - At some point, Chris looked at his future as a man, and didn't like it. He considered what he thinks being a woman is like, and said, "Hm, yeah, dat's easier, I wan dat," and began shifting his own personal backstory to be that he's a female soul in a man's body. And that's how Tranny Chris was born.