I've been in the company of transsexuals and transvestites (socially, pubs and clubs), and I am by no means an expert, but where is Rodrigo coming from? Initially he got "attention" by being The Human Ken Doll, getting fake pecs, facial surgery and all that to become doll-like, but male.
Then he decided to become, well, not quite Barbie but a Real Doll travesty of a woman (unfortunately many TS and TV women go for the sexualised fuck dolly look and you're unlikely to see them in dress-down female mode, as it doesn't fit in with the fantasy slutty schtick). Some like to look like an extra from Dynasty or do the Lolita thing - it's rare you see a portrayal of understated and subtly classy femaledom in this world - sorry, but it's just my experience.
I'm guessing attention is the operative word here and Jessica just lives in la-la land? Why would you put your body and mind through all that? Doesn't she have anyone around her to give her advice?
What is the end game here?
I have no problem referring to a person by their chosen gender - but sometimes the behaviour, mindset, attitude, conveyed to a CIS female as an outsider looking in, could frankly be insulting (and I had a TV friend who would agree with me, at times). That's a different tangent, though.
Definitely Cupid Stunt. All done in the best possible taste!
Absolutely loved Kenny!