Sex and Pancakes

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I think my boyfriend wants to have anal sex. Lately before we have sex he’s been doing this awkward thing where he pushes against my asshole with his dick for a bit before moving down to enter my vagina. The first few times I thought it was dark and he just missed the mark but now I’m pretty sure it’s on purpose. I don’t really know if I want to try anal but I think we should be talking about it if it’s on the table. How do I bring it up?

Has he been giving you any other sort of anal attention? Does he maybe slip a finger by when fingering you or linger down below when giving you head?

Like you assumed, I think it’s pretty clear he’s testing the waters to see what you think about anal because he either wants to do it or is just experiment with that part of you.

The specific testing he’s doing is called “door knocking”—he’s knocking on your door to see if you’re going to let him in.

Before we get to his intentions and what they mean in the context of your relationship, we need to address a very important safer sex note, though. You shouldn’t be moving things—in this case, his dick—between your ass and vagina, regardless of whether he’s got protection on.

I don’t think I need to remind you what your asshole is primarily used for, and even if it’s only touching the opening, you’re still moving bacteria from the ass into the vagina and possibly the urethra, which can cause a variety of extremely painful and annoying infections. So switch condoms any time you switch openings.

Now that that’s covered, let’s get back to your question. Has the topic of anal ever come up? If so, how did the conversation go?

I’m thinking if he knows you’ve never had anal sex (which I’m assuming you haven’t, based on your question) he might think he has more of a chance testing out some anal play when you’re really turned on than just asking you when you’re not.

While this may in fact be the case, first-time anal isn’t something to treat lightly. While it may be really great for some people to just go for it when trying anal for the first time, it can also be pretty damn intimidating, not to mention dangerous if neither of you know what you’re doing, or one person doesn’t want to actually be doing it.

Regardless of whether you want to or not, I agree that you should be talking about it if it’s something he’s hinting towards. I’m also a firm believer that if you can’t talk about something, you probably shouldn’t be doing it.

In terms of bringing it up, you can approach the topic one of two ways—casually or straight to the point. You can strike up a conversation about anal sex generally and feel him out. Maybe ask questions like whether he’s ever done it before, if it’s something that turns him on, etc.

Straight to the point would be telling him you’ve noticed what he’s been doing and asking if it’s because he wants to have anal sex. I would personally suggest a mix of both styles; try being casual at first, but eventually lead into what you think is going on.

I don’t know how the situation is making you feel, but I would imagine there’s at least some sense of pressure on you to go along with it, on top of the awkwardness you described. The good news is since it seems like this has happened a few times it doesn’t look like he would just go ahead and try anal without clear indication from you.

So talk about it, figure out what you both want and if you ever need a guide to easing into anal, write in again!

—Melissa Fuller

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