To answer the question, the longest I've had a butt plug in was 5 days. If I needed to go to bathroom, I would take it out, clean it, do my business, clean my backside then relube the toy and slip it back in. For longer periods of time like this I would sometimes find it very exciting and sometimes I would completely forget it was even there. I've only ever worn nJoy SS butt plugs for days like this, because I know I can get them very clean. I wore the large, 1.5 diameter for a few days, I can even pass gas with this one in and not lose it. The medium is too small for me and doesn't want to stay in for more than an hour or two so I don't even bother with it any more. The nJoy 2.0 is an AMAZING toy and keeps me horny, but it is too much for me for extended wear so I only wear it for a few hours. By the way, why IS this post in the oral section?