Needs to fit balls too

Cups, shot glasses or strange glass thimbles?

Look, idk about OP, but waaaay early on in my first days of sex, one of the sets of condoms we got just wouldn’t fit.

There she was waiting for me.

“What do you mean it won’t fit?”

“It won’t stretch enough to get through the ring.”

“That explains a lot.” (It took her a while to get “used to me”)

It’s only been a problem with two kinds, so I avoid those.