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.

Problems

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 If you can believe that enjoying a particular sexual act makes you gay, you are so far withdrawn from the realities of sex and sexuality that you can hardly be blamed.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. If you’d like to read posts I’ve already written about anal sex and how to go about it you can click these links:

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 I didn’t cover that you’d like to hear more about don’t be afraid to submit it to my formspring.

For male prostate stimulators click here.

14 thoughts on “The Guide to Pegging

  1. I haven’t ever desired anal sex and while I have had a few things up my ass I didn’t find any of them particularly exciting including numerous attempts at prostate stimulation. I do get off, however, on pleasing women and wonder if there are many women who fantasize/desire to peg their man. So my question is to the women – Do you want to do it? And do you see it as a sign of equality or dominance or whatever.

    • I do it for my boyfriend and really enjoy the dominance aspect. It’s fun role play and it feels great to break out of gender/hetero norms,

  2. I know you’ll complain about this, but if I wanted to get my ass drilled, I’d just date a guy. That way I wouldn’t have to worry about pregnancy, gold digging, nagging, etc that comes from dating girls.

  3. Pingback: Pegging/Anal « suggestivetongue

  4. Pingback: top posts of 2011 | suggestivetongue

  5. Highly detailed and very enlightening.
    Thanks.
    If I was honest about it, I have no interest in anal sex, either for myself or with a woman – that said, I’m not averse to discussing it and seeing if it feels right at the time. Except for the fact that (as the image you’ve posted so aptly puts) god seems to have put a mans g-spot up his arse and the added stimulation and sensation – as you pointed out – can be great, I find that hygenically I’d be less inclined. And this is partly because to be honest Id be unhappy doing this without some ‘cleansing’ by both parties of the parts concerned and I’d not be bothered to do that regularly unless it was just too awesome for words.
    But that’s for whatever day I finally decide whether or not I want to go there.
    You’re absolutely right about the “gay” thing and people having issues about it and masculinity, the unfortunate truth is that the majority of the world will not be changing that viewpoint anytime soon because between religion and our many, many old cultures we have too much damned baggage for stuff like this or most any other more intelligent and liberal changes in our ilfestyles and society. It will all take time. A LOT of time.
    And if a guy gives the excuse “it’ll hurt” then he deserves to be smacked soundly because unless he’s never seen porn in his life or is completely new to sex/has never been with anyone who isn’t well-versed, then he knows that early sex – even vaginal – can be tight and painful initially (hell, porn stories and the like abound with these fantasies in my past experience) and even in video porn, anal sex is shown to be painfully-pleasurable a great deal of the time. So that’s just being ignorant because you can’t think of a rational argument.
    I had this thought a long time ago that your article brought back – we learn so much and borrow and steal so liberally from the ancient Greeks in so many aspects of our lives that we don’t even realise it, perhaps this is just another aspect we should wonder if in some respect they may have been on to something. Food for thought.
    In closing (before I ramble too far), I’m not a fan or proponant right now but I can’t honestly say what the future holds – I’m very firmly heterosexual in my preference, I’ve dipped a toe and pondered this a lot to be fair to myself in life and not come to this conclusion lightly or because “its whats expected” (though it is) and am always open to learning about life.
    (Wow, I really outdid myself with the length here – sorry!)
    Anyway, nice blog and you have a great way of clearly and logically putting things.
    Cheers.

  6. Very informative and interesting material, but I am quite sure that there is no shortage of men who enjoy this highly intimate and erotic activity (in fact, the intimacy is even greater knowing he is trusting his partner enough to not betray his confidence-because, little as I hate to admit it, we are not nearly as accepting in society of any diversity-and I dont know many guys, myself included, who wouldnt be embarrassed having someone inform their friends/family they enjoy this)- I truly do enjoy it-or would, if I found a partner who did as well. For me its as much about the intimacy, trust, love, and pleasing my partner (thats another commentary in itself) than about the physical act-it has to mean something to be worth doing. In other words, i need my partner to know-whether its a one time thing with a friend who remains a close friend-closer than before, or a long term partner-I am going to be in their lives whether she indulges me in my fantasies-any of them, or not. The person is the important part. Not the act.

    That said, I look at any online site where ladies are open about their desire to peg men-and the lines of men wishing for it are miles long. I think its much easier for ladies to find willing partners than for men to. If I am wrong, I would ask someone to prove it, lol (just kidding).

  7. Me and my wife have tried it. We both like it, and do it from time to time. Its not just the feeling of it at all, its the image with her wearing a strapon, we prefer the feeldoe. much more personal and intimate. I think that the image of it, and the control she has over me is much more amazing then the actual feel of it, which dont get me wrong is quite amazing to :) Its another way for us to be intimate and we love it.

  8. So, I saw this one day after the first time my girlfriend pegged me. I say first time because I would be surprised (and a little disappointed) if it doesn’t happen again. Our relationship is very sexually adventurous, and we had started talking about it at least as far back as December. It was late February when we actually started trying ass play, beginning with a single finger mostly held in place and adding size and motion as it became comfortable. Because we did things gradually (and because we used a dildo that is a little bit smaller than my own penis), when we did eventually move to pegging, it was nice and comfortable and not at all painful. There were a couple of positions that led to uncomfortable angles, but we quickly addressed those issues. All-in-all, it was a beautifully intimate experience.

    Before I met my girlfriend, I felt insecure about my wishes for pegging. But between the two of us, there really weren’t any communication barriers to get past. The question of, “Does it mean I’m gay?” is a lot easier to reject when it’s a beautiful, sexy woman whom you trust talking about it, obviously turned on by the idea. Her enthusiasm at the prospect was what gave me the courage to ask to try anal play. Discussing something and finding you both want it is still a big step away from deciding you’re ready to try.

  9. Pingback: Top Posts of 2012 | suggestivetongue

  10. Pingback: Pegging: Tool for The Job | suggestivetongue

  11. Me and my fiancee began exploring my g spot a few months ago , and this eventually led to pegging. It’s safe to say I LOVE IT!!! And theres no questioning my sexuality over it either. I am a straight male , with a beautiful girl… One of the greatest gratifications (besides the stimulation I recieve) is how wet my womans Vagina gets from being the dominant in bed for a change !
    Highly recommended it

  12. My boyfriend and I have found that we both very much enjoy pegging. He was the one who initially brought it up. As I had previously told him that I liked a bit of anal play. We went shopping together for toys and he mentioned pegging a few tones. I was (like some women will inevitably be) skeptical about whether or not o was comfortable with donning a wang and bending him over. But low and behold, I love it. For me, I think it’s more or less the fact he trusts me so greatly. And there is constant feedback on what is good, what is not so good, and what he would like me to do differently next time. He also takes in to account my feelings on the situation and whether or not I am into it at the time. Adding a bit of “kink” from time to time can be a really healthy thing for an already strong, and open (as far as communtication goes, as I don’t like to share) relationship. Keep in mind that communication is, and always should be, #1.

What do you think?

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s