Having been butt plugging for a year, I reached a stage where a medium-circumference (1.5 inches) steel plug actually induces an anal orgasm, which is wonderful. I now find that my smaller "training" plugs tend not to stay in place while I'm moving. Inserting them still arouses, but retention is reduced. Do others have this retention issue (the anal muscles have been relaxed to accept wider toys but do not retain the smaller ones)?
I have had that problem as well I just get a bigger butt plug . My smaller butt plugs when I have it in and I move around it will fall out . So I use a bigger one and I do give my butt a break for a couple of days no more than two days and that helps to keep my new butt plug in .
I have the same issue with the small or medium plug. It feels great when I first insert it, but falls out easily a short time afterwards. I need something larger. Whatever size my FB used on me the last time, which was a vibrating plug, worked well. I couldn't see it since he had me tied down looking forward and he told me to remain looking forward while he inserted it into my ass. When he made me reposition myself after a while of teasing me with the vibration settings, I told him it might fall out. He laughed and said it won't, and he was right. It didn't come out until he was ready to fuck me. Inserting and removing did hurt a bit, so I'm guessing it was extra large.
Wow I have to use a bigger butt plug my small plug does fall out a lot to but I use a bigger one and it stays in and I try not to use it every day like I did with my first one so it give time for my ass to go back in to shape.