It's a difficult question, pal. My best experience was with a person, who never did it before. So you'll never know

I had been wearing a 50mm plug (the awesome NJoy 2.0) most of the time for a while, so I was ready to step up. I made contact with a mistress at a local dungeon and explained that I was prepared to take several sessions before I was ready to take a fist. She turned out to be perky and positive and ...