My boyfriend and I of 2 years have been trying again and again to have pleasant anal sex but sometimes it's pleasant and other times it's quite messy and it hurts. We've tried different positions, using lube, using a condom vs. not using a condom and it'll end up hurting more than pleasurable. We tried doing it the past couple of nights and as disgusting as it sounds, there's always an accident when he pulls out. It's embarrassing and kills the whole vibe, don't judge me 😬 Sometimes anal sex would go great without an accident but the next time I use the bathroom to do a number 2, there's blood. I don't have hemeroids or anything down there and we go slow on my command so it's not like it's rough or anything. Are there any tips out there for ya girl, I truly do want to enjoy it I'm just not sure if it's possible for everyone, could it just might be that I have a tight asshole ? He's the only guy I've ever been with. I've never had anything in there except a couple toys and butt plugs to try and loosen up a bit for my man. He has an average sized penis but is particularly thick. Please no judging or bullshit, I'm really trying to have some good anal sex 😂