The Guide to Pegging

I was going to call this “The Ultimate Guide to Getting Your Male Partner To Consider Anal Play” but it seemed like too long of a subject title. Instead I decided to go with the name popularized by Savage Love for a woman fucking her man in the ass.

I decided to write this because of the wide spread popularity of articles targeted at the male audience to get their female counterparts to participate in anal play. There seems to be a spotlight on this particular orientation of things, which falsely leads us to believe that women do not want to fuck their men in the ass.

From my perspective it’s simply because most people haven’t considered it. How many times in your life does someone ask you “Hey, have you ever wanted to have a penis to fuck your man with?” I mean, One- men are characteristically more hesitant to anal play (we’ll get to that later) and Two- Most who consider themselves women do not have penises and therefore do not consider themselves capable of penetrating their male partner. Unless you are particularly sexually imaginative you may not twist and turn these gender norms like others would.

I believe part of the popularity of pegging may have stemmed from the new openness surrounding anal sex as well as the boom in sex toys. I can’t say whether or not more couples are participating in anal sex and other forms of anal play, or if they are just more openly discussed. Regardless, it’s there, and it’s becoming more and more acceptable to readily admit that you like something up your ass. And not in the “foot up your-” kind of way. As for toys, there are more and more options like double penetration toys or strap-ons that (while perhaps marketed towards FF couples) shine a particular light on a woman with a vagina suddenly having a dick. I know I am not in the minority when I say I have often wondered what it would be like to have one, and even though I am not a lesbian I was quick to throw all sorts of strap-ons to my wishlist. A few weeks later it hit me, maybe I can use them.


One unfortunate point to get past (which some may find the most difficult, and … impenetrable) is the idea that enjoying anal sex or anal play of any sort makes you gay. I have some sympathy with this point. If you can believe that enjoying a particular sexual act makes you gay, you are so far withdrawn from the realities of sex and sexuality that you can hardly be blamed. I have to realize that I am in the minority as far as courses and education and studying goes on gender issues. There is still a huge population of people who don’t know the difference between gender, or sex, or sexuality, or orientation, or trans or bi or les or queer or… and while this can be aggravating for those who put so much soul into the equality of all sorts of people I have to accept that some people are going to look at anal sex and think “gay” because that’s how gay has been made public for so long. I look at it from this perspective: being gay is something that exists in your mind, it is an orientation. Not everyone who is gay likes or participates in anal sex. Liking anal sex/play means that you’ve had nerve endings stimulated and you then experience pleasure. This doesn’t mean that everyone will enjoy anal sex but I do think it means that we have the ability to, and that doesn’t make us gay. It makes us pretty lucky.

Attached to that, and somewhat of a biproduct of that, is the idea that you are less masculine if you are put into that position. That you are “less of a man” because you are playing a female-typed role. All I can say about that is… if you’re going to think like that, you’re missing out on a lot of things in life. Men and women’s roles are constantly weaving into one another. Men certainly never play stay at home dad, they never have jewelry, they’re never sensitive. That would be absurd!  Sarcasm intact, what we perceive as things “women do” and “men do” are all created by us and can be broken by us. It is only when we get into sex that these things become even more of an issue. A woman can certainly grab a dildo and fuck her boyfriend in the ass if she and he so please to do so.

It is true, though, that there may be a bit of submission involved. The same sort of submission a woman might feel when bent over and taken from behind. There is an air of it there, and with the newness and taboo-ness of taking a man from behind it might be even more submissive of a move to make. If your partner likes to be submissive it may be an easier subject to broach.

Introduction (and more problems)

You can’t expect to be laying in bed fooling around and then pull out a big dildo with a strap and ask your partner to bend over. That’s no way to begin any conversation. Conversation (pre-meditated) is the most important thing in bringing up new activities in the bedroom. And sometimes you must converse often, throughout different times of the day, week, month, year. Patience is your greatest ally. So is knowing when you need to stop conversing. And recognizing when ‘asking’ becomes pleading and nagging. Some people just aren’t interested, and if your partner is one of those, the rest of this post might not be for you. As much as I’d love to say “those fools, denying the greatest pleasure known to man” it’s impossible to say that everyone will appreciate (or even find pleasure in) anal sex.

The introduction into anal play may be easier if you and your partner already have a rapport in speaking about one another’s fantasies. Is it something you have mentioned before? Have you mentioned other things you’re interested in doing? Has he? Are you fairly sexually explorative? Speaking about fantasies often may allow more openness in your relationship as you two become more comfortable admitting things you may not have wanted to admit earlier on. I remember lying about some of the things that I was interested in trying in the past just because I didn’t particularly feel like being judged at that moment in time. It happens.

If your partner is hesitant to the idea, cover their problems with it first. If you’re lucky and pass straight past gender-typing and ‘the gay’ issue there are still a lot of other things men (and women) can be nervous about pertaining to anal sex or anal play.

It’s gross, dirty, taboo, “why would I?”, I hear it hurts, I’d rather not, I’d never thought about it and I don’t want to now, I don’t feel comfortable enough to try that yet/now, I tried it once and it did hurt so I’m not trying it again…

These are all subjects for another post, but in summary: yes it can be dirty, proper preparation can help keep things as clean as possible. Also- what part of sex is clean to begin with? Fewer people have problems with sucking dick, but in retrospect… Oh, and taboo. Right. This makes it twice as exciting, give in a little. Why would you? Why wouldn’t you? I hear it hurts too, so let’s try not to make it hurt. We’ll go slow, we’ll use lube, and we’ll make you feel good. If you hadn’t thought about it before, think about it now. And if it hurt once, it might not hurt the second time. What went wrong, if anything, that made it uncomfortable?

Anal Play

For beginning with anal play the rules are the same whether you’re male or female. Start slow, and work your way up. Fingering is the best way to start because you (the giver) have the ability to feel the muscles relax and tell you when/if to continue penetrating. It will also allow you (the receiver) to become accustomed to having something in your ass. Remember that anal play does not mean “only look at someones ass for an entire night” and this line of thinking may provide a boring and less-than-attractive experience. While anal play can feel good all on it’s own, it’s extremely helpful to double team it up with some other sort of stimulation. For men- start with the usual. A handjob, a blowjob, maybe even sex. Then slowly start to work your way downwards. As you start fingering the ass, don’t let up with stimulating the head/shaft/balls. If possible, go for a blowjob/handjob while you finger with the other hand. If you want to focus completely on him, let him masturbate while you finger. The added stimulation will assure that he’s still aroused, feeling good, and make it easier for him to relax his muscles while hopefully preventing tension. Oh, and please don’t forget lube. Lube, lube. LUBE.

A movie I highly recommend watching is “The Expert’s Guide To Anal Sex” by Tristan Taormino. This video goes more in depth on the anatomy of the anus and how the sphincter muscles work in unison. It will explain how to achieve pleasurable anal sex, or penetration at all. It will also talk about nerve endings and why anal sex feels good. For sake of length, I’ve decided not to go more in depth on anal sex in and of itself.

A note to men:

If you have ever considered having anal sex with a woman (or ever have had anal sex with a woman) I encourage you to take a moment and consider the idea for yourself. There is a reason there are now so many prostate stimulating toys out there for men. Stimulating the prostate can lead to similar feelings (and orgasms) as stimulating the g-spot in women. You can experience greater and longer orgasms, as well as greater sensations during sex. If that isn’t reason enough to give it a shot, I’m not sure what is. It is possible that you may have a bad experience, as many do, and it’s possible you may not. It’s also possible you may not be able or willing to have anal sex for a long period of time. Starting with any kind of anal play besides anal sex may be just as rewarding and fulfilling for you and your partner. Regardless of whether or not you are interested, please listen to your partners fantasies with an open mind, as you would hope they’d do for you.

If there is anything more you want to know submit at the top!

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