I posted this as a comment on a post elsewhere, but decided it was worth sharing here. That other post was about someone riding a double dildo folded to go in both of her holes, for background. Anyway, on with the story…
I had a girlfriend (see the note below) a long time ago that had a smaller one of these with a bend cast into it. She’d put it in and then put on panties to hold it in, usually. But one time she was wearing a black miniskirt with no underwear and we were taking the train home from clubbing in NYC. After we stood up to get ready for our stop, it fell out of her. Probably too much of the cum way up inside both of her holes had slithered back down while we were sitting on the train. Now, remember this was the early 80s and finding a girl that both shaved and did anal was a rarity (she was a very minor porn starlet).