Pegging: everything you need to know…and more! (co-authored with Coffee & Kink)

On Sunday morning, I sat down with lovely fellow blogger Coffee & Kink, to talk about pegging! Pegging, for those of you who don’t know, is the act of a woman (or any person with a vulva) fucking a man (or any person with a penis) anally with a strap-on. The term was coined when it won a contest in Dan Savage’s “Savage Love” column to name the act!

CK is a queer cis woman. She identifies as polyamorous, a swinger, and a mainly submissive switch. I’m a straight cis man, and…well you broadly know what kind of stuff I like!

Here’s what we had to say…

EA: Right, ok! So pegging. It might be useful to start with a bit of context here. At Eroticon, we discussed the possibility of you writing a guest post for me, and a few days later you suggested pegging as a potential topic. Can you explain a bit about why you landed on that, and what you had in mind?

CK: I thought of it while writing a post for my blog on my top 5 favourite sex toys (GOD it was hard to limit that to five!) and ended up picking my strap-on as one of them. I’m bi but tend to end up dating more male-bodied people (just a symptom of there being more straight men than queer women around I guess!) and pegging is something I’ve quite recently discovered but really fallen in love with. Beyond the act itself I’m also interested in the power dynamics and the questions around gender roles that it throws up.

EA: And that’s an interesting one right from the get-go! Should pegging throw up issues around power dynamics and gender roles? It does for me – with the former, at least – and it sounds like it does for you too, but that’s about how our society views men being penetrated rather than anything to do with the act itself, right? It reminds me of this tweet I shared the other day…

 

CK: I love that tweet! They’re so right. I wish it didn’t bring up issues of power and gender, but that would only be the case in a perfect world where socially constructed gender roles didn’t exist and power dynamics weren’t attached to specific sex acts. Ask me about the partner who didn’t go down on me for three years because they believed that receiving oral sex put me in the Dominant position!

EA: Seriously?! Wow. There’s a guy who needs to realise that if he does oral properly, there’s every chance the person he’s giving it to will be in no position to dominate anyone!

CK: Hahaha, true that. It’s definitely about how society views men being penetrated – normative views of sex tell us that the woman/vulva-owning person should always be the one penetrated and that therefore being penetrated is a feminine act. (Or a “gay” act, let’s face it – there’s some homophobic stigma attached to this too.)

EA: The homophobia is definitely a factor. And it’s something I thought about, actually, when you first suggested pegging as a post topic. The way you phrased it – ‘an advice post for men who want to try pegging but are worried it’ll destroy their masculinity’ – had me wondering whether guys are more threatened by pegging because of the feminine thing or the gay thing. Like, which one most fucks with their heads? And I honestly don’t know. If you knew which it was, you could start to break it down, but either way I suspect there’s a pretty big wall to get over there for a lot of men. Which is a huge shame

CK: That’s a really good point! The men I’ve talked to about it/heard talk about it seem more worried that liking to be anally penetrated makes them secretly gay. I think the two go together, though – some men see being gay as being feminine (and being feminine as a bad thing, because misogyny.)

EA: Yes, and then you have the Alpha-Doms, who can’t stomach the idea of women penetrating them because it robs them of their magical Domly powers

CK: Oh gosh, yes! The idea that being penetrated automatically makes one submissive is a whole ‘nother can of worms in itself. (See also: “female Dommes don’t get fucked by their subs.”)

EA: Receiving anal is a vulnerable thing in itself, especially when you’ve never done it before, so maybe for a lot of straight, moderately-to-massively Dominant guys, they’re just not used to giving someone else that level of potential sexual power over them. And I use the word potential deliberately. Even if there’s no overt power dynamic present, pegging still requires trust on the part of the recipient. Trust that maybe some guys aren’t used to having to give?

CK: That’s a really good point. You can hurt someone or even cause damage with anal if you’re not sufficiently careful, so there’s definitely a heightened level of vulnerability there. Speaking as a vulva-owning person, being penetrated is still an act of vulnerability, but one I’m used to after so many years of having sex. Being anally penetrated requires an extra level of trust on top of that – it must be even harder for a guy who’s never had that experience.

EA: Exactly! Ok, so maybe we should step back for a moment before getting too deep into the psychology of it all. You sent me some questions by email, and I want to throw one of those back at you – feel free to return the favour! It’s a pretty simple one, actually. How did you discover you were into pegging, and what was your first experience like?

CK: One of my male partners brought it up after we started dating, as he’d been on the receiving end before and liked it. I was always intrigued by the idea but it took a while for me to get comfortable enough to try it. I’d only ever fucked a woman with a strap-on before (and that only once or twice) so it was quite a new thing to get my head around. I didn’t even own an appropriate toy! We were doing some low-key sexting one day a few months back and it came up again, so I just went “fuck it,” went onto Lovehoney and bought a harness and pegging dildo. (The set I have is listed in my ‘Top 5 Toys‘ blog post and I heartily recommend it, whether you’re a beginner or not.) My first experience was hot as fuck and much easier than I’d imagined. I think having been on the receiving end of anal many times prepared me for it as I knew all the basics – go slow, lots and lots and lots of lube, listen to your partner and watch their reactions. He loved it too and I’ve definitely been left wanting more. Same question back at you!

EA: My first experience was actually with a ‘strapless’ strap-on! The Feeldoe – you may or may not be familiar with it? I was 24 and I’d been interested in the idea for a while. I don’t remember exactly how it first crossed my radar, but I’d been sticking things in my butt since my late teens, and at some point clearly decided it was more efficient to let someone else do it for me! Anyway, I was in the early stages of a relationship (this relationship) and she was bang up for it, so the decision to give it a try happened fairly organically. Sadly, while the Feeldoe has a lot going for it, it’s probably NOT the right toy to start with. My partner sort of alternated between awkwardly trying to stop it slipping out, and getting distracted by how good it felt in her cunt, neither of which were much help when it came to focusing on the thing we were trying to do! It felt really, really good though – as well as hot, and dirty, and all those other excellent things

CK: That sounds super yummy! I have been on the receiving end of a Feeldoe – my girlfriend has one – and it’s lovely but, I agree, maybe not a beginner’s toy.

EA: So for a first time, kids, I’d definitely recommend a proper sturdy harness, and maybe a small-to-mid-sized dildo. Your eyes may be bigger than your stomach…or your arse!

CK: That’s very true… you can always build up to bigger ones (or not – it’s not a competition and sticking with things on the smaller end is totally cool and valid too.) That’s what I like about the Lovehoney harness – it comes with a nice smooth 5-inch dildo, but has different sized rings so you can swap out the dildo for a bigger one later if you’re so inclined. While we’re on the subject of toys, I strongly – STRONGLY – recommend something made of good quality silicone. You can get cheaper toys made of jelly or plastics but they don’t tend to be as body safe.

EA: Yes, excellent point. I used a jelly one for a while, and there’s no doubt it felt good…but it’s kind of off-putting when the colour starts to rub off (where’s it going?), and I never felt all that confident about its quality/body safety.

CK: Okay, here’s my next question for you: did your experience change how you felt about your gender identity, sexuality, kink orientation or relationship? Why or why not?

EA: Ooh, good question. Though maybe one with a disappointing answer, in my case! Because no, no it didn’t. It perhaps solidified certain things I already vaguely knew about my kink orientation – that I like being submissive sometimes, and I enjoy various… scenarios that pegging fits into rather well – but in terms of gender identity and sexuality it had no impact whatsoever. Maybe because, as I said, I was already pretty experienced with other forms of anal (self-)penetration by then? It just felt like a particularly enjoyable extension of that.

CK: That makes total sense! Not a disappointing answer at all – I think it’s totally awesome that you know yourself so well that engaging in a specific act doesn’t make you question any of the things you already know about yourself. It was the same for me, really. It definitely put me in a Toppy headspace, which is a thing that I enjoy sometimes, but I already knew all the things about my identity and nothing about that changed at all.

EA: So you had that first experience with pegging, and I’m guessing there have been others since. Has it got better each time, as you’ve learned the ropes, and have you found that what you enjoy most about it has changed/evolved over time? (That first-time thrill vs… something else?)

CK: To be honest, I still haven’t done it many times! It’s one of those things where the stars have to align, as it were – both our headspaces and bodies have to be up for it at the same time, as well as having the energy to deal with the setup and clean-up and so on. But I find that pretty much any sex act gets better over time and with experience. (The biggest lie anyone ever told me? “The time you lose your virginity will be the best sex of your life and nothing will ever beat it.” LIES LIES LIES LIES.) What I enjoy about it, though, remains fairly consistent – the changing up of our usual penetrator/penetratee roles, getting to be in control, seeing my partner’s pleasure in a whole different way, the physical THUD of body against body as I fuck them… You?

EA: Well I’ve had pegging experiences with a number of partners now, over the course of, ooh, about 11 years, so it’s inevitable that there’s been a fair degree of variety! I’m happy to say that I haven’t had any bad pegging experiences. I’ve tended to do it with really switched-on, sex-positive women, who’ve gone out of their way to make it good, perhaps because it involves a heightened level of trust (actually, another contributing factor to this is that the person doing the penetrating is thrusting with something that isn’t part of their body…that they can’t ‘feel’…and most tend to go pretty carefully as a result).

CK: Switched-on, sex-positive partners make any experience better, that’s for sure.

EA: But yes, I’ve found that over time it’s been easier to play around with some of the psychological elements of it, because I’ve got more relaxed about the physical act itself – and that’s pretty cool. You also get to experiment with different positions, angles, etc, and of course everyone has a different style – whether you’re talking PIV sex, oral, spanking, whatever. Variety is the spice of life, etc!

CK: Exactly! Actually that’s a good next question: any particular favourite positions (or any you’ve found that really don’t work?)

EA: I have lots of thoughts on pegging positions! Though to be fair, most of those thoughts essentially boil down to one word: YUM. And I’m particularly interested to get your take on this one, by the way, because I’m guessing the pleasure/utility of certain positions might be very different for the person doing the penetrating than the person on the receiving end. But from my POV, I really like doggy. Or a slight tweak on it, where I’m more on my front than on my hands and knees, with my arse in the air. If I’m feeling super-submissive, or I’m with an experienced partner, doggy is great for just surrendering control and letting her take over. On the other hand, if I feel like I need to take the lead a bit, or it’s a big dildo where I want to ease onto it slowly, straddling her can feel deep, and intense, and just so good – that also works if she wants to watch me come at the end of it, or to suck my cock while I’m riding her.

CK: Ooh, yeah that’s hot.

EA: But for your regular, everyday pegging, it’s hard to beat missionary…for pretty much all the reasons missionary is so great for PIV sex. Closeness, eye contact, ease of communication, etc etc.

CK: I’ve found the most effective position to be me standing on the floor with my partner on their back on the bed. Neither of us is particularly tall so this works well from a height perspective. From behind is also really fun. I’ve never tried doing it missionary but I can see why that could work well!

EA: Yes, I must admit I’m sort of using ‘missionary’ as a catch-all for any position where I’m on my back and she’s on top! The set-up you described works really well – especially if my legs are over her shoulders

CK: Ok, next one. I’m intrigued by a question you suggested in our emails: how does pegging fit into your broader D/s mindset? (If at all.)

EA: It does and it doesn’t – in the sense that it almost occupies its own little space in there, but also connects to a few other kinks that I (or the right partner) can tap into as part of a pegging scenario. I’ll say this – while I absolutely know that it can be, for me being pegged is never a dominant act. Like, I would never tell someone to do it to me. I might ask for it, but I’d always want them then to take the lead. Beyond that, it can range from super-submissive to something more nuanced and complex. How about you?

CK: Yeah, the D/s thing is complicated. I struggle to imagine pegging someone while I’m in a submissive headspace, though I can see ways in which it might work. (Especially if there’s a third party involved – I’ve fucked a girl with a strap-on under orders from a Dominant partner before.) It definitely taps into my more Dominant headspace, because I am the one in physical control and my partner has put so much trust in me to allow me to do that to them. I REALLY like being asked/begged for it – that puts me in a Toppy headspace quicker than almost anything else. But it can also be a D/s-neutral act where neither of us is in a particular Dominant or submissive role and we’re just doing it as equals because it gets us off.

EA: Yes, and I think it’s really important to emphasise that pegging doesn’t have to be connected to D/S play. That’s almost as big a fallacy as the feminine/gay thing. You can have regular, sweet, dildo-in-butt sex just as easily/naturally as you can have regular, sweet, PIV sex.

CK: That leads me nicely into another question you asked me, which was: “Unless you’re using a double-ended/vibrating toy, pegging is very much focused on male physical stimulation – as a woman, what do you get out of it?”

EA: I’m glad you brought that one up! I’m super interested to get your take on it. Is there a physical pleasure component to it for you, or is it mainly all the hot, kinky vibes you get from the whole situation?

CK: Definitely both. As I mentioned previously, the thud of body-on-body is super hot for me – the raw physicality of fucking someone, you know? And if the harness is positioned right, the base of the dildo can stimulate my clitoris and pubic mound in a very enjoyable way. Like realistically it’s never going to make me orgasm, as I need penetration or more concentrated clitoral stimulation for that, but there’s definitely a physical component. Of course, the hot kinky vibes form a big part of it, as is seeing my partner’s reactions – I’m all about reactions and I feed off my partner’s enjoyment.

EA: I’m guessing the noises he makes are a big part of that? I can’t think of anything that makes me louder in bed than that…thud. The feeling of being really full, y’know – full and fucked.

CK: Absolutely. The noises and the facial expressions. Yum! Follow-up question to that: do you orgasm from being pegged?

EA: Yes! Almost every time. Normally with some additional stimulation (my/her hand on my cock, or her mouth), but I’ve come from it before without having my penis touched, and I can often feel it building very quickly just from the penetration

CK: I love making a guy come from a combination of fucking and cock stimulation.

EA: And being told not to come in that situation is incredibly hot. Pegging goes well with orgasm denial/control, for sure.

CK: Ooh… now that I’ve never done but I imagine it would be super hot. I’m usually on the receiving end of orgasm control. Shall we wrap up with some top tips for newbies or people who are nervous but want to try?

EA: That seems sensible! I’ll throw a first one out there, just because I think this is pretty much the #1 tip for anything (or anyone!) new you’re doing sex-wise. C-O-M-M-U-N-I-C-A-T-I-O-N. Communication is key.

CK: Basically that’s my top tip for a happy life, to be honest!

EA: Talk about what you want. What you don’t want. What you think you might like to try. What worries you. How the other person can help. Limits. Fantasies. The whole lot.

CK: All of this! Yes, absolutely. It’s also a good idea to talk about any hang-ups or insecurities (perhaps “will you see me as less manly if you fuck me in the ass?” type of things.) And remember that “I don’t know if I like it/what I like, can we just explore slowly and find out?” is 100% legit. No-one is born knowing what they like sexually, it takes experimentation.

EA: Great point. ‘I don’t know’ is always a legit answer, and a good partner will respect that, and respond to it in the right way. Any specific tips for the person doing the first-time pegging? (I have a couple for the guys, which I’ll share in a minute)

CK: Go slowly. Remember you can’t feel the toy in the way you would with a bio-cock. Watch your partner’s reactions and check in often, asking them how they’re doing. Choose a small-ish toy to begin with (again, smooth silicon is best.) Don’t try to use an internal toy like a Feeldoe the first few times, if you want to use one at all. Don’t try to be in serious D/s space the first time or two – you both need to be able to communicate clearly at this stage. And LUBE LUBE LUBE LUBE LUBE. Water based, high quality (no weird warming or tingling agents and PLEASE FOR THE LOVE OF SEX nothing that is designed to be “numbing.”). Use more than you think you need, then more still. Remember, the ass is not self-lubricating and if there’s not sufficient lubrication, it will not only hurt your partner but risks doing actual damage.

EA: Amen to all of that! You’ve basically just written ‘Pegging 101’ in a couple of paragraphs there! For the guys, I would add this: Explore. Yourself. First. I think it’s a pretty good rule of thumb for sex generally – the first time something gets put inside you, it’s probably best if you’re the one putting it there. Figure out whether you like anal penetration as more than just a concept! Invest in a butt plug, or just use your fingers, but the more you experiment on your own, the higher degree of confidence you’re likely to take into any first-time pegging situation.

CK: That’s such a good tip!

EA: Remember though, if you’re going to use a toy, it absolutely has to have a flared base! A lot of standard dildos are not suitable for anal play – same goes for bullet vibes, vegetables, and champagne corks!

CK: That’s also an amazing point – get something specifically designed for anal play, ideally. But… Champagne corks!? Is that a thing!?

EA: 19-year-old me thought it was a thing… I had fancy but misguided tastes at that age. I was lucky – nothing got stuck – but not everyone will be.

CK: Hey, I once masturbated with my mobile phone on the vibrate setting, no judgement here. But yes, in all seriousness getting things stuck will at best lead to an embarrassing trip to the doctors and at worst could be a major medical emergency.

EA: We’re almost out of time. Final thoughts?

CK: Final thoughts: as with anything else in sex, approach with an open mind, an exploratory headspace, tonnes of communication, and high quality lube.

EA: I’m not sure I can improve on those awesome tips! Except to add: no preconceptions regarding what it says about you. It says nothing, except that you think being fucked in the ass is awesome.

CK: I love that! This was amazing, let’s do another collaboration at some point!

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