House to myself, and a large Cucumber available. It was a monster: A full 3 inch (beer can thick or closed fist) wide at one end tapering down slightly on the other, drastically curved. It was time to stuff the chute to the max and hold for a long period. My idea was to expand that rectum cavity and anal-ring and hold, to allow the ring to breakdown and the chute to get used to being filled to the max. This exercise may allow the ring to easily start taking the big black dong in daily sessions.
The scene was set, Just shaved the pubes, balls and asshole bald, and snapped a larger rubber-band around the nuts, isolating them off nicely. Fat end first. The monster was greased. The 3 inch end split the ring and the chute accepted it with ease (still in great rectal shape). Once the widest part made it past, the taper on the cucumber, cause the whole thing to slide right up the chute until it hit the bend.
My plan was to lay down for 1/2 hour and allow the chute to relax and accept the stretching, 20 minutes and I started jacking my hard cock. I stopped and caught myself, had another 10 minutes of training, so I got another thick rubber band, doubled it over and around the balls and cock this time. I held my bald hard cock straight out and started to work my banded of nuts and not jacking. Got into a good rhythm working the nuts and hold the cock straight out. In combination with my rectum chute stuffed to the max, I was getting ready to squirt off hard.
I eased the large cucumber out so that the Ring was at maximum stretch when the powerful cumshot hit, so the asshole ring could spasm fully dilated causing even more anal-ring break down. A big one hit, sending the ring into powerful spasms as the ring tried to clamp down, losing all control of the ring for those 10 seconds. Great solo ring breakdown!