"I was always afraid it would hurt, but anal sex actually isn’t so much painful as it is uncomfortable. But! The discomfort is so extreme for some people that they can barely do it - like my best friend, who’s tried a few times with her fiancé and barely gotten it in, no matter how much lube they use. The key, apparently, is to be relaxed, which you really aren’t gonna be - in fact, knowing it’s about to happen will make you tense up more than usual - unless you happen to love it. I…do not love it, but my boyfriend is super into it, and he’s very respectful and lovely about not pressuring me. We maybe do it once every couple of months. I’m usually a little tipsy, which helps with the relaxation part and makes the whole thing a little easier. He’s a big advocate of using a buttplug beforehand to 'loosen everything up,' which may or may not work, but just draws it out more than I’d like." —Anna B.
Related: 8 Things You Need to Know About Anal Sex
"It's not the worst thing ever, but kind of like the same way flossing isn't the worst thing ever. There's nothing fun about it for me. It's not that it's painful, it's just mildly uncomfortable and really not my thing." —Jo R.
"I used to be obsessed with anal. At one point in high school, I was having more anal than regular sex. When done right - and by right I mean when the guy doesn't shove his d*ck into you like a horse in heat - anal can teeter on that dangerous line between pleasure and pain. He feels bigger than ever and completely fills you up. As he's going in, you have to hold your breath because you feel like your body doesn't have room for air and his d*ck at the same time, but once he's in, the pleasure radiates through your whole body. One time, however, my boyfriend and I were walking around my neighbourhood and fighting, as per usual. After coming to no resolution at all, we decided to agree to disagree and, of course, have hate sex next to a neighbour's house in broad daylight. He pulled down my shorts and without any warning or lube, shoved it up there like he was stuffing a cannon to launch it against his worst enemy. I screamed, 'TAKE IT OUT TAKE IT OUT TAKE IT OUT!!!' Once he was out, I had to pull up my shorts, squat down on the floor, and meditate so I wouldn't sh*t all over the grass. It literally felt like he was pulling out my insides along with his penis. The moral of the story: Hate sex is hot, but hate anal leads to pain and explosive diarrhea." —Nina T.
"I tried it once a long time ago. The guy I was seeing wanted to do it, and I was resistant but eventually gave in. He tried to put it in, but it just hurt too much. I don't think he used lube, and it's just really tight. Maybe I'd do it again with the right person if I had a lot of trust in him. Either way, it's not something at the top of my list." —Clara A.
"Amusingly, my first sexual intercourse was via anal penetration. My high school sweetheart was raised strictly Catholic and was 'saving it for marriage.' While I was disinterested in this wait time, he did explain that anal sex didn't count since it couldn't lead to procreation. His being exceedingly well-endowed made taking it slowly and using plenty of lube the obvious choice. The oddest thing I noticed was that the initial penetration would generate a tight sensation in my throat, similar to what you might feel after a bad scare. But it was an exciting feeling, not scary at all. It's a slow but pleasantly luxurious sensation of being gently and benignly pulled inside out. It certainly was extremely erotic, and I felt aware of my entire body as an erogenous zone. I discovered I was able to orgasm via anal penetration, and anal play is something I enjoy to this day." —Mollena W.
"The key to good anal - yes, that's a thing - is having a partner you trust completely and who will do it right. That means lots of lube, start small with a pinky finger just like in Fifty Shades, then work your way up to small toys or butt plugs. After that, anal can be amazing! It is super intense, and your lover has to be extremely delicate and careful and be a good listener and super patient—and you as the receiver have to have a lot of trust in that. Because the anus is, after all, an exit, not an entrance, and so it could really, really hurt. This is not an act that should ever be undertaken with a random dude or at a random moment; you both have to want it, and you both have to be prepared. No assholes allowed in the asshole! I think that's one of the best parts of the whole ordeal. It takes so much time, trust, and communication that it just amplifies everything physical going on because you are so connected with your partner." —Tess N.