[Kisune Karnon]

Let's do some pump progression with the inflatable plug. Make sure to use as much lube as needed.

Insert the plug. Do 1 full pump and then push it out without using your hands.
Deflate.
Insert the plug. Do 2 full pumps and then push it out without using your hands.
Deflate.
Repeat adding 1 full pump each iteration and pushing it out without your hands.

Be sure to count properly. Once it starts to come out on its own while you are pumping, hold it in with your hand to keep stretching your hole.

I don't know what your maximum amount of pumps are. You need to beat this maximum with this progression by a minimum of 3 pumps.

Once you hit your new max. Hold the plug in your ass for 10 minutes so your ass can get use to the new maximum. Bonus points if you make your new max 5 more pumps than your old.