Question: How many times can I make a boy cum with my feet? Answer: As many times and as often as I want. This boy is on reverse all fours, and I have my favorite pantyhose gloves on. The gloves make it a little hard to wiggle my way around, which is the perfect excuse for practicing my foot job skills-- not that I need practice, at this point. There’s really never a wrong time. Honestly I’ve gotten so good at it, it's pretty much just foot milking at this point.