Emptying your bowels 30-60 minutes before any type of anal play will help you relax and make using a plug more comfortable and less messy
Lube is essential when using a butt plug because our butts don't self lubricate, you'll also want to select a lube compatible with your butt plug's material. For instance, you can use water, silicone, oil, or hybrid lubes when using a glass or metal plug. However, with a silicone plug, you'll want to stick to water-based, oil, or hybrid lubes unless otherwise directed by the manufacturer.
When applying lube, be sure to lubricate the outside and inside of the anus. While you can use your fingers for the outside, a lube applicator comes in handy for getting lube into your anal canal. Gloves or finger cots are also great to use when applying lube, especially if you have longer nails.
Find a position you'll be comfortable holding for a few minutes, such as laying on your side, back, or getting on all fours. It all comes down to personal preference and comfort. Next, take a few deep breaths and concentrate on relaxing your butt muscles and sphincter. Position the plug right at the opening of the anus and gently press in, slowly adding more pressure as you ease the plug inside. Take your time.
It may feel weird at first or a bit uncomfortable, but it shouldn't hurt. If you're experiencing pain, stop, remove the plug, and rest, then add more lube and try again. Once the plug is inserted, you can wear it for as long as it's comfortable. As your muscles begin to tire the plug, may slip out. At this point, you should remove the plug for a while.