If you want to leave an anal plug in for an extended period of time it is recommended that you remove the plug and replenish the lubricant occasionally throughout the day.
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If you are interested in leaving an anal plug in for a long period of time, try one that is made of silicone or jelly rubber with a bulbous head and a narrow shaft and of course a flared base.
Tip: If you are going to wear an anal plug all day, carry a small ziplock bag with you so if the plug becomes uncomfortable or you need to remove it for some reason, you have a sanitary place to put it!
Since the anus is not self lubricating a personal lubricant needs to be applied before use as over a period of time that lubricant can dry up.