I sort of touched on this the other day, posting about trans visibility & representation in entertainment. I've not seen Wentworth or oitnb, but I've watched Sense8 and of course I've seen plenty of representation of trans individuals in other than shows, movies, etc. I think, like any character portrayal, the context matters as much as the method.
For instance, what sparked interest in the topic was the show Twin Peaks. During it's original 2 season run from 1990-92, David Duchovny actually guest started for a few episodes (pre x-files) as DEA agent & transwoman (then described as a ->-bleeped-<-) who had recently transitioned from Dennis to Denise after discovering herself during an under cover operation. I actually really enjoyed the way the show & Duchovny handled the part. You need to keep in mind the surreal, bizarre, awkward structure of twin peaks when thinking about this, but the main character who knew this character previously took to the change as simply as saying "Okay," and a little blurb about how he looked forward to hearing her story. The character interactions we're believable in the context, if not realistic, ranging from one or two characters who were present for the introduction candidly offering a weird look, to others either totally seeing her as any other woman, and others seemingly clocking her but saying nothing. In the end it didn't feel like the character was the butt of a joke, just another stop on the show's surreal journey as it critiques everyday life and weirdisms. They definitely used the character for humor, but I never felt that they demeaned the character in the least bit. If anything most of the humor came from the audience and character reactions to Denise's presence. Furthermore he sunk so well into the role to the point where I was giggling most of the time he was on screen. I'm about to get into the 2017 season and I read he reprised the role, so I can't wait to see what has changed in the portrayal and depiction as opposed to 25 years ago. Needless to say, I have my hopes up for a fantastic performance.
In the case you describe in Wentworth, just going on what you said, that seems as though it could be a misrepresentation, I'd have to see it for myself to give a good critique. Tessa is absolutely right that there is no singular representation of transmen or women, so try looking to the context and character backstory, but I do find it at the very least odd that the character is supposed to have transitioned & post op but have all of those other male traits as well as being in a women's prison.
