I remember trying this when I was much younger and it stung. Now I tried it and it's not that bad. If you use something that doesn't stretch you, you can pretty much go up to your prostate without discomfort. If you stretch or go in and out a lot, you could end up with a burning pain when you pee but it goes away pretty quick. Going through the prostate burns more and can be uncomfortable but I'm finding less discomfort the more I do it. Girlfriend loves it and gets off on it, so that's fun.