How To Ease Your Way Into Anal Play With Your Man

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anal play

Get in there, ladies!

Q. My boyfriend and I are very open in and out of the bedroom and I’m very into anal play and I’m trying to turn him onto it.

I’ve never tried prostate massage on a partner but I’ve done lots of reading and we’ve talked and he said he’s willing to try it and I want it to be a wonderful experience for both of us because I think we will both be really into it.

Any advice for a newbie and any recommendations for toys? Thanks in advance.

A. My recommendation, since he is cool with trying, is you don’t focus on doing any insertion at the beginning since it can be the most intimidating part of anal play.

There are a lot of other things to enjoy before you get to insertion.  

While you’re going down on him, lube up your thumb and give him a “taint” massage, pressing deep into his taint before moving down to his anus and rubbing gently in a circle.

The lube will really make this feel great, and before you know it, he’ll likely be pushing against your thumb, which can be slowly and gradually inserted.

Let him do the thrusting. If he’s enjoying himself, he certainly will.

Another wonderful-feeling thing you can do is a "rimjob.

Running your tongue in a circle on and around the anus can be so wonderful to feel. If you have any concerns about taste or cleanliness, you can always add flavored lube or use an oral barrier.

Once you get to insertion, the big key with anal play is a gel type lube. Thinner lubes work great vaginally or for masturbation — because those are all about the slide — while gel lubes really help, well, lubricate a tight space.

You'll want to start very slowly. 

A pinky finger is excellent for beginning. If the words “is it in” are ever uttered, you know that more can be handled.

As for butt plugs, a common mistake most people make is going with something very small, thinking that they can’t handle more.

In reality, the skinny and small plugs (about the size of a finger) don’t do what they should be doing, which is to fill the rectum, followed by a dip where the sphincter can close to hold them. I’d recommend looking for what he thinks is the largest plug he can accommodate, and then purchase the next larger one.

Beyond that, when you get to the advanced moves of pegging or inserting dildos, it’s all about comfort level and whether or not you are willing to push yourselves just a little bit.

Pegging can seem like a scary thing for many at the beginning, but I know that, for me, this has rapidly become one of my favorite sexual activities.

Hope that helps!

This article was originally published at Life on the Swingset. Reprinted with permission from the author.