10 Stories About Having Anal Sex For The First Time That Explain Exactly What To Expect

Anal sex is a bit like a roller-coaster: exciting for some, nerve-wracking for others, and an experience with so much fun potential. Maybe anal sex is your only/main option, because of your anatomy or because of vaginal discomfort. Anal can also be a kinky alternative, or a kinky way to give or receive double the pleasure. If you're curious about what your first time having anal sex will be like, take it from the women and non-binary folks who've been there: It's going to be a physically distinct as well as emotionally distinct experience.

There might be some physical discomfort in the beginning, since your muscles are trying something new. That's why it's important to take it easy, be patient, and ensure that the receiving partner lubes up during anal sex. As for emotional discomfort? There really shouldn't be any. Sexual consent is always and absolutely necessary — no "if"s, "and"s, or "but"s about it. Something to consider is that consent for having anal sex, specifically, is crucial, too. As Planned Parenthood puts its, "Without consent, sexual activity (including oral sex, genital touching, and vaginal or anal penetration) is sexual assault or rape."

Another aspect to consider is safety during anal sex. Use a condom to prevent the passing of STDs. And if you're switching from anal sex to vaginal sex — in that order — a new condom is necessary. Once you've got the time, lube, condoms, and a patient, consenting partner, you'll be good to go. Here are 10 women and non-binary people on what their first time having anal sex like — the convos they had leading up to it, how it felt emotionally, and whether or not they'd do it again.

Alone time is key

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It was something we’d discussed doing before and it was kind of the first time having sex in a house without anyone else there (since we had a bunch of roommates at the time). I didn’t enjoy it that much, but I also didn’t hate it as much as I thought. My partner had had anal before and loves it.
We’ve done it since, though, and I’ve grown to enjoy anal play a lot more. Although, I still have some resistance to anal regularly, because it’s just kind of a hassle with potential before and after clean-up, and safe sex stuff.

— Alissandra, 25

No, seriously

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I did it for the first time on Valentine’s Day with my ex-boyfriend. I wanted to try it because I was curious about it and he was down to try something new, too. I think I was more excited to do it than he was because I wanted to brag to my friends about how I was so 'sexually adventurous.'
We did it in my freshman-year dorm room; I was in a split double. He put it in me, and I think I did the "and I oop" face, sat up, and ran to the other side of my dorm room. We tried it again, but right as he was about to put it up my a**, my roommate came back. (She had a boyfriend, too and was coming to get something before the two of them had sex. She had assumed me and my boyfriend would already be at dinner.) When she opened the door my boyfriend popped up, covered himself in the blanket, and hid behind my door. I didn’t tell my roommate until much later that the sex she had walked in on was actually us trying anal.

—Allison, 20

Foreplay helps a bunch

My SO and I tried anal, and it was awesome. We were actually kind of irresponsible and didn't really work up to it, but did use plenty of lube and had done a lot of foreplay. I was OK with it and relaxed, and I experienced almost zero pain. [I] enjoyed it a whole lot!
I never seem to get quite as wet as when we do anal doing anything else... Since we first started doing anal, we have bought a slim dildo that we use to loosen me up a bit before his penis and it has helped a lot.

Captain_jawa on Reddit

Lube is essential — so is trust

I had my first anal experience a few months ago, but it wasn’t a very pleasant one. It was my first D/S [dominant-submissive] dynamic relationship and he never used lube, saying he didn’t like using it because it was “messy." He would only use spit and I almost always found a little blood after.
I’m angry at myself for letting it go down that way. But I ended things with him, so I won’t have to deal with that anymore. I’m sure I’ll eventually trust someone enough to try again, just not sure when.

— Kaileigh, 31

Building up to it with butt plugs helps, too

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For me, it was a great experience, because we built up to it over a long period of time with external stimulation, fingering, and butt plugs. I felt really comfortable because my partner was very responsive and didn’t make me feel pressured at all.

— Sammy Rei, 28

Giving can be as fun as receiving

Zackary Drucker / Gender Spectrum Collection
I have an interesting 'first-time giving anal' story. The [person] I was dating at the time came out to me as MTF [male-to-female] trans. While I was shocked finding this out, it was kinda nice. I got to explore a little of lesbianism and the dominant kink of mine... I was all down for this kind of scenario. I really enjoyed being on the giving end of pleasure, in that sense.
I'd love to do it again, but my current BF isn't into it, which is fine. LOL I got to at least play it out once!

— Holly, 23

It can def keep your sex life interesting

My partner and I didn't have much experience with anything other than 'vanilla,' so we experimented with loads of things. Turns out anal was something that we found interesting and different. It feels more naughty, like doing it on a sofa.

The_Hatchet on Reddit

Go into anal relaxed

It was about four weeks after having our daughter. We were a little wary of PIV [penis-in-vagina] sex, but were feeling sexy. We had never done any anal play before, but my husband said that he wanted to finger my ass, so I said OK. Then one thing led to another, and we did it. It went well. I'd tried anal with exes and he could never put it in because it was too painful. I just relaxed and let it happen. It was pretty enjoyable. No soreness, blood, or poop.

SpicyPoffin on Reddit

And take your time

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So, once upon a time, I never thought I would want to ever try anal. But when you meet someone you love and care about and trust, and they really want to try, you also want to try for them. First few times were awful. We had to stop. And stop. I didn't like it. I didn't want to do it at all. [Then, the other day] I had successful anal sex with my boyfriend.
I just really wanted to please him with it, so I spent a lot of time reading how to help make things work out smoothly. Read a lot of Reddit stories. The key is: Be relaxed. No really, it hurts if you are tense. A couple of days ago we tried it again, and I actually got off at the same time as him while doing it...
TL; DR: Anal can be nice.

— dirtypaws on Reddit

Best-case scenario: Everything just comes together

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OMG, I did anal for the first time a few months ago! Loved it. I think we were just having a relaxed conversation about sex and our experiences. He’d done anal, but I hadn’t but always wanted to! I’m not sure who brought it up first ... I think before he may have just asked if I wanted to try.
I was a little nervous that it would hurt, but I was also excited about it — because I felt totally comfortable with him, and I knew it’d bring us closer. And there’s taboo around anal, so it felt a little freaky which I loved. Plus it’s sort of like "another virginity," in a way, so I felt that same level of innocence as my first time having sex.
I always felt like the first person I did anal with would be someone special, and he’s definitely special to me! And of course, he loved it. So, [I felt] mostly excited, sort of nervous, but also completely and totally comfortable. And a little naughty.

— Kyoko, 22

You might try anal and absolutely love it. In that case, bring on the anal beads and the butt plugs, and maybe even experimenting with different kinds of lube. Or it might be the case that your first (or even second and third) time having anal sex might just feel OK — and that's perfectly fine, too. Whatever the case may be, pat yourself on the back (or butt) for trying something new in bed.