I usually can't go more than a couple of hours with a good size plug in my ass. I usually start small and every so often put in a bigger one. Before long I have to jerk off. If I use a plug with a really wide base I can only take the stretched feeling for a short time. I think my sphincter gets tired. Nonetheless, I went with a simple aneros prostate plug today and it has a very narrow base. I stuck it in about 8 hours ago, which is easily the longest I have ever gone plugged. I think I am going to try to sleep with it tonight. What is the longest time that you have been plugged and how wide was the base of the plug? I would be pretty impressed if there are people out there who have been plugged for several hours with say a plug with a 2" base.