Wish I could give you screenies, but I can't. I don't have that dress.
We tried three different ones.
One had 2 arms, but they were already wide and resting on her bicep.
So with arms down, the sleeves slid down and the dress fell off. Well. It didn't "fall off", but it dropped below V4's boobs. Not quite the effect you look for in a gown lol.

When I said adjust for rotation, I meant because V4 was rotated a bit in the last frame, we applied that rotation to the first frame, thinking maybe the dress is twisting off and that's what's causing it -- didn't make a blind bit of difference.

The harsher setting... yeah, we cranked up the cloth settings until you had about as much movement in the cloth as you get in leather -- and it still slipped below the boobs.
If we kept the arms up, the dress stayed almost on the boobs, but not quite.

The strapless one... ferget it. It just landed below her boobs every time. We couldn't get the darn thing to stay on her.
I got a feebie one here and I'm running that through a simulation atm... and it seems to behave.
It has arms though.

I can only assume it was the way that dress was set up. (They were all evening gowns, if anyone has an idea of which dynamic ones they might have been... holler. I should have taken the name down lol.)

Collision friction on or off made no difference.
Poking in or not made no difference either. :/
In fact, having the dress stick inside her boobs made a tiny bit of difference -- until the last couple of frames when it all slipped half way down her boob again.

Silke