Not sure if this is a thing in game but I wish there was a Quest or Upgrade that gave a Perk that would let your dong fit anyone. If not a way to take Condensol mid conversation.
I mean, you could always save edit to have multiple one eyed wonder weasels of varying sizes if you really wanna see everything. But it's admittedly a bit of a pain to do, because a lot of the scenes seem to use exclusive statements about your bologna pony. Like, if you have dongers that qualify for more than one scene, you'll usually always end up with the same scene, and you'll need to get rid of that one to see the others. That's only if you're really determined to see everything though. If you just wanna be able to sling one up every character after just one change, you can probably just add a smaller backup wang that you can ignore except for when you're too big to fit otherwise. Although, I think there's a few scenes that don't take bulk penii into account, and only check the meatrod supreme, so you have to make your first pleasure pole the small one, but then you end up using the teeny weeny in more scenes, and it just turns into a general pain in the ass. And not in the fun way. I think there's a way to get polydicktaly in the game itself without cheating, but it's been a while, and I'm a lazy bastard, so I always just cheated that shit how I wanted it.
But a "spongy" trait or something so that your lil' Richard would squeeze to fit into anything would definitely make the game more fun. No running back and forth trying to alter the size of your Johnson (or save editing), just a grand old time with a collapsible willy. It'd kinda be a bitch to code though. You'd have to go back and add shit to every scene. I mean, you'd really only need to add a check at the front to see the max supported size in the scene, and feed that into the scene to get the text, but you'd have to do that over and over.