For long term wear: Invest in a good quality, thin stemmed plug that stays put, and a good thick lube. Non-porous stainless & glass tend to stay lubed longer, a curved plug is better, a good flared base is a must.
I prefer the NJoy Pure Plug large, typically worn 6-8 hours at a time, mostly for the naughty factor and always for the great fun afterwards, g/f likes her Pure Plug medium. Sometimes I sleep with mine in, never had a lube problem with removal. Everyone's different, re-lube as needed. Usually after a bathroom break and hot shower you should be able to wear one around a good while. (Always take a break and remove it if there is any pain or major discomfort, there should be none). Sometimes there may be very minor discomfort for beginners when first starting out, this is normal and usually goes away after an hour or so.
One trick I tried with this stainless plug (If I go out) was to weave a folded paper napkin or paper towel around the inner ring figure-eight style and lightly saturate it with some thick long-lasting skin moisturizing lotion like Aveeno daily moisturizing lotion link
Stops it from chafing and a very comfortable topical lotion for longer term wear, works great.
(This method actually provides a little extra lube to the plug stem area which can help keep you comfortable after several hours).
Long term wear quickly gets easier with practice, work your way up gradually. I often wear this plug out in public with no worries. Get the right plug and a thick, long-lasting lube and have some fantastic naughty fun!
Highly recommended for long term wear: NJoy Pure Plugs (medium or large) : link