I've got 2 characters over 250 but the Killing Loneliness achievement is still locked.
I'm glad you like the game!
As far as trans men content in general, I've actually had this asked a couple of times recently, but unfortunately, at least right now, I don't have any plans for it. Even disregarding the time it takes to go through and update all of the scenes for new options, the more specific something is, the harder it is to find videos that really fit the scenes and I just don't know that there are enough varied videos of that type out there to actually cover all of the scenes in the game.
That being said, it could change in the future as that sort of stuff continues getting made, I just don't know that it would even be possible at the moment.