Just as with any good sex, trying something yourself first may help you relax. A review conducted on anal in confirmed that up to 40 percent of people have tried it at least once. We always use lube, no questions. It wasn't my first time, but I've never done it regularly. Oral sex is the ultimate gesture of acceptance between two people. In "I Slipped," Mindy's boyfriend Danny tries the surprise approach and she is, of course, shocked. You should be highly aroused before going there, and having an orgasm or three beforehand never hurt either. How's a person ever supposed to give anal sex another try when it feels that bad the first time? Sorry to be gross, but it's hard to find this kind of information! The most important part is to have good lube that you trust, and be sure to use it on both yourself and whatever will be penetrating you for maximum ease. A glass of wine and romance can help. First of all, I cannot really enjoy it if I'm not touching my penis at the same time, which means that I'm ready to orgasm quite early so I cannot satisfy my partner. And thanks to plugs, pegging, and toys, you don't need a person with a penis - or another person at all, really, in order to try it. Yes, you might feel really naughty. Even though it really feels good some of the time, I just can't relax and stop thinking about whether I'm clean inside and whether I really need to go or if it's just the penis causing this feeling of being 'full'. Also, it is quite an intense feeling and it soon becomes too much for me to bare. This was my decision and I really want to enjoy it, I enjoy fingering myself, it turns me on when I think about it and sometimes it really is pleasurable.