Spoke to an ex today. He said some women he's been with have been both very fleshy (he LOVES a huge ass) and either too lazy or too inexperienced to move their folds out of the way during initial penetration. Where he'd normally use his hand to make sure his foreskin wasn't getting in the way, his hands were instead busy holding onto handfuls of her. Another way he said his foreskin might end up inside was if the woman was not a tight fit for him.
I'm confused by a number of things here, possibly misreading.
Folds? If by this he means labia then I take exception to his comment about some women being too lazy or inexperienced to move them out of the way. I don't part mine for entry because the feel of them being pushed open is a divine. I also hate spread open positions due to the lack of labial stimulation.
If 'folds' isn't in reference to the labia then these are very fleshy women indeed.
I'm also really confused about his talk about how the foreskin could get "inside" them. If an uncut cock is in a woman the foreskin is in them too. It's attached. There are no tie-backs to keep it at the base. Unless the guy holds the foreskin back throughout the encounter on each outstroke the foreskin in almost all cases rolls forward again. We don't see it because it's rare to pull out entirely and check with each stroke.
Degree of foreskin movement is dependent on a few things: lubrication, flare of glans in relation to the shaft, length & tightness of the foreskin and tightness of the orifice penetrated.
If the opening of the foreskin is too small to retract behind the head as with phimosis then there's not much movement and it's staying forward.
If it's relatively snug and the glans flare enough in relation to the shaft it will still slide on the shaft but sort of ruche up behind the head on the outstroke.
For lubrication vs orifice tightness an experiment.
Take one finger and place it below your lower lip and press just firmly enough that you can feel your gums through your skin. Wiggle your finger and feel how smoothly the inside of your mouth glides over your gums(assuming no braces). Next grab some lube and keep experimenting with more lube or less pressure until your finger slides over your skin more than the inside of your mouth glides over your gums. That's how wet and loose the orifice needs to be for the foreskin not to move at all.
Same idea for entry. Unless the guy has a super long foreskin dangling from his erect penis he doesn't need to roll it back to enter. As soon as there is friction and pressure from the orifice on the outside of the foreskin the penis will glide within it's own sheath until the foreskin is is fully retracted anyway.
Does anyone remember those water balloon tubes? It's pretty much the same action as poking a pencil (eraser first) through one. You'd need a lot of lubrication and a very light touch to stroke over the tube without the tube moving at all over the pencil.