I am dubious. The lesbian and bi dating scene in a place like Charlottesville is not that big. The number of lesbian and bi women who are interested in sleeping with trans women* is not that big. Chris is a mess, physically and mentally.
Add to that his biggest barrier, that he is on one hand completely resistant to approaching people in an appropriate way (like talking to them at a bar or party), but ridiculously unaware of how creepy he comes off via email, and I don't see it happening.
I know sweet, attractive lesbians who have a hard time finding a date here in the Boston area, which has a big lesbian and bi community. As for casual hookups, I think Barn (typo, but it stays) circumscribes Chris's social life enough that he's not likely to be in position for those (closing time beer goggles, going to a "poly munch").
I think Chris's best chance for sex given his life at the moment would be joining some kind of queer consciousness-raising group and finding someone else who's got issues and doesn't find him repulsive. But he's too lazy to do anything other than play with LEGO and rage about blue arms.
*I also think Chris's unusual gender-identity status is going to be a big strike against him. He doesn't have the self-awareness or panache to pull off "male lesbian" or "female soul in man's body," and he isn't really making the choices that say "woman" to people in the LGBTQ&c. scene, like using female pronouns. Or, for that matter, shaving his face!