The appeal of the posterior

With the eyes of the world on Kim Kardashian’s “Break the Internet” Paper magazine cover, and all things ass-related becoming a bit less taboo, we wanted to share a personal story about trying anal sex.

The first time I tried it was after my high school boyfriend’s good friends (a couple) raved about how great it was, how they did it all the time, especially if she was on her period. We did it in my basement, bent over a hideous, orange 70s couch. I can’t remember if my parents were home upstairs, but I seriously hope not.

We used lube, eased into it and he went slow, checking several times to make sure I was ok. It didn’t hurt, nor did it feel amazing. It was a little weird and uncomfortable, kind of like losing your virginity, but definitely not the painful and traumatic experience you often hear about.

That was the second time.

The second time we were just plain stupid (try to keep in mind I was 17 before you unleash your judgements). We did it in the shower and quickly learned that water is NOT a suitable replacement for lube. In fact, it’s quite the opposite. The experience was extremely painful, he immediately pulled out, and we never tried it again.

That’s one of the biggest problems with anal sex: Once it doesn’t go well, it’s very hard to shake the memory and muster the courage to try again. And what’s the point if vaginal intercourse is working just fine?

I got back on the horse, so to speak, about two years later with a guy I was seeing in college. He was oddly open to experimenting (more so than any guy I’ve dated), in spite of the fact that I’d just taken his virginity a few months prior, which wasn’t easy either. We waited a few months and the first time we tried to have sex, he stopped right before, told me he couldn’t, and ran out of my dorm room.

Perhaps he felt like he was making up for lost time, because he’s the only partner of mine that’s ever been open to and initiated things like playing with anal beads or sucking my toes. The latter was surprisingly arousing and I wish I could convince my current boyfriend that my feet aren’t all that disgusting. Unfortunately, the rest of our experimentations, which took place in a sweaty, attic room at his parents’ house, didn’t go as well. This includes anal sex. It hurt badly and like the last time, ended quickly. Looking back, I think much of our failure can be attributed to our total lack of incompatibility, chemistry and simply not knowing each other very well.

But, I’m not a quitter. The next time was with someone I’d been intimate with for about five years, on and off. Admittedly, it was a turbulent, incredibly unhealthy relationship, yet there was a lot of history and passion mixed in it. We’d discussed trying anal for several years before we actually went for it. 

We were smart about it, working our way up slowly with fingers. It finally happened in his horribly messy room on his mattress on the floor, just after a blowout fight. The timing wasn’t ideal, but our make-ups were always especially hot and heavy, and for the first time, I understood why people have anal sex. It can feel good. Really good. I came. We did it a few more times after that night and it never went badly.

I’ve been in an actual healthy relationship for more than three years with a man that I live with and plan to marry—and we haven’t had anal sex—yet. He says he’s never had it with anyone, but he also hasn’t expressed a huge desire to try it. I feel bad, like I’m cheating him out of a seriously intimate experience I’ve given to others who meant less to me. And even though my last attempts at anal were surprisingly successful, I still haven’t forgotten the times that weren’t. One day, I hope to saddle up for him.

Jessica May is a freelance writer happily living in sin with her boyfriend and vibrator.

Photo credit: Creative Commons 


  1. Andrea Jayne on November 16, 2014 at 11:12 pm

    Interesting post…I find that it only works if the guy is of a certain length/girth. Gentlemen that are "hung" and thick, no way! Nope, no, no-ish.

  2. on March 26, 2015 at 5:17 am

    It’s awesome to read some honest and nuanced insight from a woman, both positive and negative, in regards to anal sex. It’s a bit problematic, however, that the author concludes that she feels, "bad, like I’m cheating him out of a seriously intimate experience I’ve given to others who meant less to me." While this may be her honest experience, following this line of thought to its logical conclusion is disturbing indeed – specifically this sentiment infers that 1) a person might "owe" a certain sex act to a current partner 2) that there is something "wrong" with past sexual experience/s and 3) that this sex act primarily functions as a "gift" rather than an act of exploration or pleasure or whatever other experience for the woman and her own body. I’m not saying Ms. May’s thoughts ought to be policed, simply that it would be great if she could acknowledge the implications of her statements and that they are representative not of directives or imperatives for other people, but of her personal emotions.

    As to the commenter Andrea – again, totally a valid personal experience. But since there is so little representation of anal experiences for women, I’d like to add that preferences in length and girth vary widely from person to person and body to body. Personally, I actually find larger penises (or dildos, or hands) to be more comfortable and pleasurable anally, likely because smaller ones involve more continued contracting of the sphincter, which is the part of anal sex that is less comfortable and less pleasurable for me. Big penises (or dildos, or hands, etc) allow the sphincter to relax in an open position while length and girth ensure that my hot spots, specifically the underside of my g-spot get reached. Hot indeed.

    Thanks Crave for your awesome work on sex positivity and keeping such conversations alive (and sexy, and fun) online!

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