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How to Ease Into Anal Sex? Ask These Two Women

How to Ease Into Anal Sex? Ask These Two Women

Generally speaking, anal sex isn’t the first thing that comes to mind when you are thinking of mutually pleasurable things to do with a partner. Instead, the urban sex legend goes, “Guys want it because they’ve heard it’s tighter than normal sex and they’ve seen it in porn, and girls occasionally acquiesce as a bargaining chip/reward/very special birthday present.”

But aside from tipsy late-night conversations between women (or women and their gay guy friends), practical knowledge of butt sex in the wild is hard to come by. Thus, we asked two women who have actually done it about their motives, their preparation process, and whether it’s ever gotten them off.

Probably the No. 1 thing we all want to know is … does it hurt?

Woman A: For me, it did. That first time was like, “Oh dear god, nothing is supposed to go in there.” You really have to relax. Like a lot of deep breathing and you have to let everything go. Then it kinda stops hurting when you finally relax, but for me, it can get bad again when he starts thrusting. I read that putting in a plug during foreplay helps a lot, but I’ve never used one.

Woman B: Yes! If it didn’t, this wouldn’t be a topic of conversation.

Why do it?

Woman A: I decided to try it because I’d heard it can be really pleasant and some girls can orgasm from it. It’s also really taboo and naughty, and I’m one of those girls who likes that. So I thought I’d give it a shot.

Woman B: I usually only do it when drunk and if trying to impress the lucky dude I’m with.

Who wanted to do it more — you or the guy?

Woman A: Me. I had heard that some girls love it, so I wanted to try it. The guy I’m with is not really into it, which is part of the reason I’ve only done it three times.

Woman B: Him. When it happens, it’s because I’ve conceded. Depends on how much I’m into him … and afterward, I kind of feel like he “owes me something.”

What does it feel like the first time?

Woman A: It’s weird. It feels tight and not pleasant. It feels like a muscle cramp. Like you’re trying to open a muscle and stretch it out and it doesn’t want to listen. That’s what it feels like at first. I didn’t like it. And then you relax and it feels a little better.

Woman B: At first, extremely unpleasant. Kinda feels like a penis going in your anus.

What does it feel like over time?

Woman A: It feels like you’re full and it’s super-intense.

Woman B: Over time, you adjust. Similar to vaginal intercourse, I suppose.

Does it ever feel good?

Woman A: I know some girls who love it … [but] it’s one of those things that definitely takes more than one try to see if you like it.

Woman B: It never really feels good. Just becomes more tolerable, I suppose. It also depends on the size of his manhood.

Is getting a wax back there expected the way it is for other body hair down there?

Woman A: I don’t think you have to get waxed. In the beginning of my relationship, I’d get Brazilians, but now I rarely wax for him. So I wasn’t waxed. [But] it might the girl feel more comfortable if she is waxed, if she worries about that stuff.

Woman B: No, a wax isn’t required … I suppose any dude who’s into anal wouldn’t be so particular as to request a smooth entryway.

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On average, how soon in the relationship — if it’s a dating scenario — do you think it generally happens?

Woman A: We had been together for seven months before we did it. But I know girls who do it when they first hook up with a guy. But those are the girls who love it.

Woman B: Hmm … in my experience, if he’s into it, you know soon into the relationship. This type of “fetish” isn’t easily concealed, in my opinion.

How much lube? What brands are best?

Woman A: Lots of lube! Like, lube on me and lube on him. I couldn’t even imagine doing it without lube.

Woman B: Lots. Any kind. Even saliva if nothing else is available.

Do you bleed?

Woman A: I didn’t bleed (well, at least not that I know of). But I feel like it’s totally possible, especially if the guy forces it or you don’t use lube (cringe).

Woman B: Not that I recall.

Do you spread a towel on the bed or anything?

Woman A: I’m not really sure why you would? I feel like it isn’t more messy than normal sex.

Woman B: Sheet stains are a risk and should be considered collateral damage.

Do you have to get an enema and/or anal douche? (I heard you have to get an enema, but from a friend who is sort of uptight/crazy.)

Woman A: So I thought about this, but no, I didn’t get one. I wouldn’t in the future either; I feel like that would be such a process. And I’ve never heard of anyone doing that, so I don’t know if this is normal and I just wasn’t following protocol.

Woman B: Nah. If he’s requesting entrance to my exit, he should know the risks at hand. Unless you had Chipotle for dinner. Then I’d say enema, for sure. I feel like this tends to present itself in the heat of the moment. Who’s gonna say “Hang on, hon, let me go flush my ass. I’ll be back in a few?”

Is there a big cleanup afterward?

Woman A: I don’t think there’s a big cleanup. Especially if you have a condom. Just slip it off and that’s all the cleanup we needed.

Woman B: Again: Chipotle.

Are there useful things re: angles that we should know?

Woman A: I did it doggy style the first time and then I did it with him sitting on a couch (I was on top with my back to his chest sitting on him). The second is definitely better. And according to two gay guys I know, the correct way to do it is to have the girl on top and she can ease herself down and go at her own pace, and once that happens you can flip yourself over so he’s on top now and then you can do whatever you want. But the most important is for the girl to go at her own pace.

Woman B: I think doggy style is most conducive.

Condoms still, obviously, right?

Woman A: Totally to the condoms.

Woman B: Even more so!

Have you ever had an orgasm from anal sex alone?

Woman A: No, but I’ve heard it’s possible.

Woman B: Nope, but then again, I’ve never had one from vaginal penetration alone.

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What do I say? I'm a little shy... But that doesn't stop me from exploring my sexuality. You could say that I'm a little bi-curious ;) Anyway, happily married to a great guy. My interests are travel, staying fit, and having fun... Maybe a too much fun. Lastly, I'm passionate about the lifestyle and sex positive movement that is happening around us.

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