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I feel like it isn't more messy than normal sex. I decided to try it because I'd heard it can be really pleasant and some girls can orgasm from it. I usually only do it when drunk and if trying to impress the lucky dude I'm with. It was my first time and it was super painful — almost made me never want to do it again. The Meanest Reviews of "Man of the Woods". Start with your partner sitting as you mount his lap, face-to-face.