Wouldn't Chris have been sent to a women's jail? I know the prison documents all list him as a male, but he did get to continue taking his HRT while in there so presumably they do accept him as a legit tranny, and most of what I've read on the subject lately is that troons are getting sent to women's jails in the USA, with many prisoners trooning out for just that reason.
Given access to a population of women mostly deprived of access to men, I think even Chris would have been able to get laid with some regularity. It would have been the start of the institutionalisation saga, with Chris committing increasingly outrageous crimes to get sent back.