double entendre referring to romney saying he was progressive and had “binders full of women” to consider for positions, this is satirically positing he tries to court ‘woke’ voters by having binders full of trans men, the double part being because trans men who either do not want top surgery or haven’t had it yet often wear binders

joke 2 being ‘expand’ is used in quoted text, and as a spoiler this section has to be expanded

joke 3 is by over explaining the jokes so detailed that they are no longer funny, but so detailed that it loops around and becomes funny again

joke 4 being that it didn’t actually become funny during joke 3 so this is an anti-joke

joke 5 being that the anti-joke is so bad, it has actually become funny by this point:::