Groans4U

I've experienced that. Eventually everything comes out, although it's only happened with toys and not my hand. It happens most with small toys with flared ends. I have a doc Johnson anal probe, which is tiny but the bulbed end sometimes gets locked tight, I'm guessing by the sigmoid entrance, for a maybe 30 seconds after I cum. Even when pulling it and relaxing it won't come out, but eventually I loosen up and it comes out. First time it happened it freaked me out a bit.

Back when I was trying to fist myself I was given a good tip. Clench and relax. Once warmed up. At the point where you can't go further, instead of pushing/bearing harder down on the toy clench your butt hole as much as possible and hold it (for how long is trial and error, and you probably won't be able to hold it for too long anyway), then stop holding and r-e-l-a-x and at the same time try bearing down on the toy again. It probably won't work immediately but you should definitely notice some difference. Just repeat several times each session. Also good breathing technique can help. When you clench, inhale, and when you relax and bear down, exhale.