Never Have I Ever: Had Anal Sex

Here's What It's Like To Try Backdoor For The First Time

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Maria and Eli are a married couple from Chicago in their early 30s. They have a two-year-old child together but have never had anal sex...until about a month ago. Well, there were several attempts involved, but as they were all towards the same goal, it counts.

Some readers may think, “How can two people make it past one kid, and into their 30s, without putting it up the butt?” These are likely the adventurous folks who attend sex parties, or whose lives looks less traditional than marriage and kids. Others readers, may simply not find anal sex appealing. What is kinky, and what is vanilla, is all about perspective.

In many ways, anal sex is more physically dangerous than attending a sex party and having vaginal sex with your fluid-bonded partner at a sex party. Unlike the vagina, the anus isn’t self-lubricating. Without the proper warm-up, plenty of lube, and a willingness to go slow, it can be easy to have one awkward or painful anal sex experience and write it off forever. Or, without lube and warm-up, the receptive partner can experience tearing and bleeding (eek) that would give one good reason to be okay with not experiencing anal. However, when their sex life became a bit stagnant after having a kid, Maria and Eli decided to go where they have never gone before (with anyone): up the butt. Here’s what they had to say about their first-time experience with anal sex.

AskMen: You two obviously are committed to one another. You’ve made vows and created offspring. What happened this past month that suddenly put anal on the table, and what kept it off the menu before now?

Eli: Well, to get to your second question, I was never against anal sex, it just didn’t turn me on the way it seems to with other guys and some of my friends. I’m a big fan of the vagina. Not to sound too Christian or anything but… it’s just, what it’s made for you know? Anal seemed complicated, and Maria never really brought it up, and the same goes for the women I dated before we met.

Maria: Yeah, I have the same boring answer. It just was never a “thing” for me. And to answer the other part of the question, I recently got over my guilt and started watching porn, after a friend suggested it to help get my sex drive back after having a kid and being too tired for anything. I stumbled across some anal sex videos and... yeah…couldn’t get it out of my head.

How did you bring it up to Eli? Suggesting something new, even in a relationship as close as you two share, can be scary.

Maria: Well first we talked about porn and watched the porn together.

Ooh!

Eli: And the first one she picked was like, “All Anal” or something like that. So I got the point.

Maria: It may sound crazy, but yeah, I was nervous to bring it up, but I thought if he watched the video with me he’d also think it was hot, and want to try, and I was right. We had sex like we normally do with the porn on, and afterward the conversation about trying anal just came up.

So did you try it there and then?

Eli: Not right there and then because like, well we just already had sex, but like a week later. But it was a disaster. We didn’t use lube, I just tried spit, and it hurt her, and then [our son] woke up. Parents know how hard it is to find alone time for sex. Doing something you’ve never done before in bed with kids in the house is damn near impossible.

Yeah, I think that’s a common mistake a lot of people make the first time they try butt sex. You need to go slow, use lube, do your research, warm up; it’s not like in porn videos where you can just stick it in. Especially with kids around, I imagine.

Maria: Yeah, that first night I think we both forgot about it because we had to get up and deal with [our son]. But a few days later I started Googling and researching about it, and talked to one of my single girlfriends who is adventurous, and realized what we did wrong. We have lube, lots of women need it more often for any type of sex after having kids, so we were just idiots that first time for not using it.

RELATED: The Best Positions For Anal Sex, Revealed

You said “first time…” Does that mean there was a successful second time?

Maria: We gave our kid to my mom for the weekend. Ha! Please don’t use our real names for this.

Eli: Hahaha yeah we needed time alone anyway, so we gave [our son] to Maria’s mom for the weekend, and did date night, breakfast in bed, the works.

The works meaning butt sex?

Maria: Yes. I gave Eli strict instructions, we started with his fingers, used lots of lube, and went super slowly. It was painful, but not totally in a bad way? I came by touching myself while he did it, that’s for sure, but then after I came, I wanted him to stop and asked him to take it out [laughs].

Oh yeah, I’ve done that plenty of times. That totally counts. Men get too many orgasms anyways. Congrats on the anal and the successful marriage!

Eli: Ha, thanks!