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I got the medium since I'm pretty experienced when it comes to back door play, and it was really pleasantly challenging at first, but once I relaxed and got used to it, I could wear it for a whole day if I wanted (I sleep with it in almost every night); that's how comfortable it is!!! I think it was a combination of perfect stem length (so that it didn't wanna push out when I cough or something) plus the slight squishiness the whole plug has ( mine had the inner squishy completely intact) which allowed me to comfortably wear it the whole time: it's comfortable af.