I've been trying anal around a year. I play with a dildo. I empty, clean, relax, lube up, and try different positions, yet I only experience little pleasure. There is no discomfort. I fantasize about anal a lot, and it's a huge disappointment I don't enjoy it. Anyone else experience this? Submitted September 25, 2019 at 01:01AM I've been trying anal around a year. I play with a dildo. I empty, clean, relax, lube up, and try different positions, yet I only experience little pleasure. There is no discomfort. I fantasize about anal a lot, and it's a huge disappointment I don't enjoy it. Anyone else experience this?