I have seen this happen many times IRL

Jennifer Jason Leigh - Fast Times at Ridgemont High

Quick Times (xpost from r/nsfwedit)

AIKA | Tan Babysitter Gets Seduced And Creampied Multiple Times

Aika - Makes Him Cum Three Times

Good times

Phoebe Cates in 'Fast Times at Ridgemont High'

I wanna let one lucky older guy cum on my ass multiple times

Saturate my horny times

I will make you so pleased that you will cum many times

I am the kind of latina that fucks 5 times a day!

Slap it three times before you cum inside