The Guys Who Were Disappointed When They Finally Had Anal Sex with Their Girlfriends

It turns out you can’t believe everything you hear on the Howard Stern Show

When it comes to top-tier romantic writing, people often bring up Shakespeare’s sonnets or the legendary correspondence between famous couples like F. Scott Fitzgerald and his wife Zelda. But for me, in the pantheon of iconic expressions of passion, no one can ever top the love letters James Joyce wrote to his dirty little fuckbird, Nora Barnacle. Over the top in both their adoration and filth, there was one thing that took Joyce’s euphoria to the next level — when Nora agreed to let him fuck her “arseways.” 

In fact, Joyce never tired of Nora’s ass after the initial pounding and constantly dreamed of fucking all of the farts out of her. According to him, she gave him the thrill of doing something he considered the most taboo, and therefore, the hottest. Personally, I think Joyce’s obsession with dirty “no limits” sex (aka anal) is far more understandable than any of his books.

Even now — in a world where you can easily watch porn in which a live-action Marge Simpson gets her yellow pussy split open by Homer’s giant yellow cock — for many straight men, anal remains a forbidden, prized sexual conquest. Lucky for them, too, their female partners are on board. According to a study in The Journal of Sexual Medicine, about 43 percent of females have engaged in anal sex, which is a solid gain from the previous high of 33 percent. This is in line with porn search increases in the category as well: Pornhub says in 2019 it was a top ten search term, the most popular one being “anal gangbang.”

Moreover, I dare you to find a woman who has never been asked if she’s down with an ass fucking. If anything, it’s become a kind of badge of honor to be a woman who’s done it. A porn star friend of mine once put it this way: “It’s not that I love anal as much as I love being a girl who does anal.” (Someone cross-stitch this on a pillow for me, please.)

I know EXACTLY what she’s talking about. I once had a guy pounding me from behind, and after a few moments, he started growling, “You like it in the ass. Don’t you? You love getting fucked in the ass.” 

There was only one problem: He was in my pussy. With perfect comedic timing, I looked behind my shoulder and said, “Seriously?” But he was too busy “enjoying anal” to notice. I shrugged and accepted my good luck: I now had the reputation of a cool girl who does anal without any of the hassle. I had stolen anal valor. (In my defense, I did properly earn it years later.)

Yet not every guy who has his anal dreams come true lives happily ever after. Some have flown too close to the chocolate starfish and been burned by those heightened expectations. Brady, a 33-year-old in Minnesota, first became intrigued by the act after hearing Howard Stern wax rhapsodically about it on his late-night E! show. When Brady told a woman he had never tried it, she decided to give him a surprise. “She put a condom on me and worked my dick right up her ass. I initially thought, This feels different, but I ended up hating every second of it, although she seemed to like it. I just wasn’t into it.”

For Isaac, a 36-year-old in Oklahoma City, the problem was the level of expectation. We’d kinda built it up over a few days, and made it a ‘special night’ where we had dinner and a few drinks beforehand.” But when the moment came, it just didn’t live up to the hype. “We were doing it doggy style, and she asked me to slip it into her ass. I made sure to go slow and ease it in because I was terrified of hurting her. She was kinda into it, but for me, the entire time I was just thinking, I wanna be in that other hole, the wet one right next door.”

James, a 45-year-old in New Jersey, has a much funnier reason for not enjoying anal. When he met his future wife, they talked about giving it a go. On the night it was going down, however, things didn’t go as planned. “At the moment of penetration, a driver outside of our apartment leaned on his car horn. We both laughed so hard she squeezed me out of her.” The connection to that moment of sexual slapstick was impossible to recover from. “The next time we tried it, all I could think about was the car horn. I haven’t been back in the butt since,” he jokes.

Of course, the thing that most frequently ruins the “fantasy” of anal is that shit happens — literally. Brad, a 49-year-old in Canada, spent years fantasizing about the act, but when it finally happened, kind of spur-of-the-moment, things got messy. “There was significant smell and residue afterwards, making me do the penguin walk to the bathroom to wash off my dick,” he says. “This girl was very cute and clean, but the human body does what it does.”

Despite his bad experience, Brad is willing to give it another go. “I’d be willing to try it again in the future, but only at the female’s request,” he tells me. “And I’d make sure there was ample pre-cleaning. While pussy typically smells great, the smell of shit can really kill the mood.”

James Joyce begs to differ, Brad.