Plastic surgeons know that human skin is very strechable and they often insert special balloons under the skin to stretch it out to create more skin for use elsewhere.
So I would agree that somebody could stretch out their asshole skin by inserting large objects frequently. Skin will stetch and will not always return to its previous state.
I would also guess that somebody could damage their asshole muscle in a manner that would make it very loose. Wether by nerve damage or tearing of the muscle.
However, if you only insert dicks in your asshole that are no bigger than a normal shit, and you make sure the asshole muscle is relaxed properly, I do not see how this would stretch the skin or damage the asshole muscle anymore than taking a shit once a day.
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