Well from my own discoveries, you can wear a buttplug for a extremely long time without any problems, I own a large steel plug which is best for long term wear, my record so far is 22 days without taking it out once, I sleep with it in everyday, I wear it basically all the time just pull it out to check if everything is ok, the only pain I've ever had is when the base pinches with your skin if you sit on a flat surface wrong, this stops when you have been wearing it awhile and learn how to sit. Some tips for extreme long term wear, BUY A STEEL BUTTPLUG, the reason being is they can respond to temperatures very well. But to get them to stay lubed up and not painful for a long time is first clean yourself out, if you plan on having it in for a month, or two months, do some serious cleaning, I mean at least 5-6 hours of just getting your entire large, and a large portion of your small intestine cleaned out, if you plan to wear it for 3 days then just a quick 15 minute clean will do. You need to buy silicone lubricant, there are two reasons to this the first being it evaporates and absorbs into you much slower than water, and because it becomes much thinner with heat. So after cleaning yourself out, heat up your buttplug, now be careful I don't mean 150 degrees, just heat it up to the hottest temperature that you feel comfortable with, coat it, and the inside of your rectal cavity with lubricant, insert it and lay down and try and invert your abdomen area. The reason that you do all of this is because gravity as you wear the plug will push the lubricant down to the bottom of the plug, the point of the heat is to thin it out, which makes the lubricant travel further into your intestines, upper rectal cavity, ETC. this eliminates the problem of the steel plugs becoming dry after a long period of wear, this is because once the buttplug cools to your body temp the lube will become thicker and will slowly drain down as you walk around, or do whatever, the correct amount of lubricant is actually very important. If you plan to do short times (a few minutes to about 3 days) then a normal amount would be about a 2 handfuls of lube. If you plan on doing more than that then it spikes dramatically due to the fact that you start absorbing and evaporating lubricant, so instead of telling you how much per day, in case someone wants to go longer. So for every 5 days after about three days, you need to do about another 4 to 6 handfuls depending on you and the plug, every 20 days you need another 9-11 handfuls... The reason I'm measuring it by handfuls is because the bigger the person holds more line in their hand and their rectal cavity, so one handful would be as if you put a decent amount of soap in your hand like you do in the shower. If you feel ANY dryness during the time that you are doing this then restart, and add whatever amount you think is right for you, then invert you abdomen for a longer period of time