The first time a boyfriend asked me to try anal sex was in high school. I was 17. And because I loved him — in the way you can only when love when everything is fantastical and a first — I agreed to try it. We dated for three years, and basically introduced each other to every type of sex there could be: I even gave him a Kama Sutra book for Valentine’s Day one year, not realizing that experimenting with so much inexperience would never be quite as hot as my coveted Cosmopolitan magazines promised it would be.
Even so, after reading about what to do, we gave it a try. But as soon as he barely entered me, I asked him to stop and apologized, telling him that I just couldn’t do it. It was too scary. Too much. It hurt.
Fast forward to a few months after I turn 22 and I’m desperately in love with a "mature 29-year-old" man that we’ll call Scott*. After years of lackluster, jack-rabbit sex, I’m amazed at what this older dude can do with his tongue, with his hands, and with his body. He isn’t the most well-endowed man I’d ever known, but he is the first to ever give me a stellar orgasm and to really, as the romance novels put it, worship my body.
We’ve been dating for a while, and after a quickie in the morning, he casually asks if I’d ever be up for trying anal sex. I go into the story about my ex-boyfriend from when I was younger and he rolls his eyes, kisses my cheeks and says, “But I know what I’m doing. It’ll be good for you, I promise.” I tell him I’ll think about it, but secretly, I just want to do more research (my journalist brain never stops investigating!) to figure out if anal sex is ever good for women.
The very idea of someone entering into your backside seems a little gross — right? You’re only supposed to dispose of (gross) things back there, not put something inside that’ll be painful as it moves deeper. I couldn’t understand — for the life of me — why in the world anal sex would make me as turned on as I am in doggy style?
Even though I’m nervous, I trust Scott. And he’s made me so much more adventurous in bed and more comfortable with my sexuality, so I decide if I’m going to try anal sex with anyone, it’s him.
The first time we went for it, he started by going down on me. It was as good as it always was and right when I thought I couldn’t take it, we started having "normal" sex. It was slow and sensual and he made sure to focus on kissing my neck and ears, getting me more and more turned on. He then flipped me over and we had really hard doggy style for a while, and without lube or anything, he easily slipped inside my backend.
Like before, it was painful, but he told me to breathe as slowly eased all the way in. He then reached around and started to play with me with his fingers as he gradually moved faster. I got more comfortable as he went on, and almost forgot where he was. As I let go more, the tension faded. It didn’t hurt as much. And without even thinking about it, I had one of those explosive orgasms that you feel all the way up to your face.
It was amazing. And I was hooked.
For the duration of our year-and-a-half relationship, we worked in anal sex at least once a week. We got into such a steamy rhythm that we eventually tried different anal sex positions — including missionary and spooning. It easily became one of my favorite ways to have sex, and though the clean-up was pretty messy every time, I loved how the orgasms varied and how much fun we had with it.
Nowadays, the "anal sex conversation" is one I bring up with guys I’m dating. Once we make it exclusive, I casually bring up the topic of things to try in bed, just like my previous ex-boyfriends had done. Most of the time, like 9.5 out of 10, men are pleasantly surprised with my appetite for non-traditional intercourse. It isn’t always good, and to be fair, sometimes a guy is simply way too big for it to feel good. But sometimes, I get lucky (and ahem, he does too) and I find that happy place with anal sex again.
It might seem invasive to some — and yeah, a little dirty — to have anal sex as part of your bedroom adventures, but I think it's always worth a shot. And frankly, a few shots. Just like when you lose your virginity, losing your anal sex virginity isn’t exactly pleasurable. But with the right person, the right patience, and the right movement, you might just find yourself persuaded to the other side.
My biggest recommendation? Though my first anal sex experience was sans lube and it was fine, lube will be your best friend. And a nice, warm shower before you get it on.
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