plugs that stay put

I tried the Tripple Ripple butt plug but unfortunately it does not stay in place. It eventually pops out. What you can do is sit down whilst wearing it. Otherwise, use different sized butt plugs, which work absolutely perfect. I understand your idea of wanting to stretch your anus. Use the butt plugs. It will work promise. You can also use suitable size dildos to probe the anus after using the butt plugs. This will maintain the anus relaxed. Cheers!

as the tripple ripple review describes, a hand needs to keep it in, a hand that could be used better elsewhere. I even see some contorsionist action necessary.
perhaps your suggestion of different sizes plugs is a better solution although this will also stretch the "special" cupboard :)