I mean I have drawn trans guy Cy stuff before, and while he definitely wouldn't be as much of a fiend as canon Cy (tfw dysphoria makes you reluctant to groom teens 😔) I feel like he'd definitely fit in my series of "realistic alternate Cys". I think being exposed to Cy and his transness early on would probably make Lynn more open to the idea of dating a trans man than canon Lynn, but your "yay liberal points" guess is right on the money, she 100% would internally congratulate herself for that. Overall, I still think they'd have a pretty good sex life, but Cy would undeniably be a huge stone top, and it'd probably take fucking decades of being together for him to let Lynn touch his genitals directly, cuz I think his dysphoria would be absolutely hellish.