Probably the biggest I've seen(male)

[NeutralOmen]

https://www.xtube.com/video-watch/3-dildos-and-3-fists-in-his-hole-a-monster-prolapse-43881811

Bottom_FF has been stingy for years but this video finally shows off not only the size, but looseness and width of his prolapse. Crazy. 

If only there were a female counterpart! DGG is the closest but she has yet to really break it.

[elirian]

Yeah holy shit, that's absolutely massive.

[the239]

That is a perfect ass. i want mine to do that someday.  i want to prolapse as much as i physically can. idc about my hole i want it destroyed.i need a couple guys to fist me looser and pull me inside out. 

[Rosebutt]

10 minutes ago, the239 said:

That is a perfect ass. i want mine to do that someday.  i want to prolapse as much as i physically can. idc about my hole i want it destroyed.i need a couple guys to fist me looser and pull me inside out. 

Same here.

[mwm831]

I would do anything for my ass to hang out like that

[Rosebutt]

He has mastered not just his anus and not just his second ring but the ability to take large objects past it and pass them back out without any seeming fear of them getting caught or lost. I can only imagine.