Before you go all “Shut Up And Take My Money” buying your new toys, harnesses, dildos in every colour and shape imaginable, plus if you’re planning on engaging in pegging with someone (instead of as a solo activity), then you need a consenting and enthusiastic partner!
If you can’t talk about this with a partner, how do you imagine dealing with them if there is an accidental poo-nami during pegging? Being vulnerable about sex can be tough, but if you want the strap, you’ve got to have the chat.
Approaching the topic with your partner
Times have changed a lot since Slave D and I started exploring pegging (back in my day-!) and I’ve seen how pegging is mentioned a lot more commonly now - and not just as a blue joke. We’ve seen it as a reference in Deadpool, Deadpool and Wolverine, Broad City and Sex and the City. But as we talked about earlier, some people still have misconceptions or hesitations about it.
If you’re the pegger or the peggee, a way to consider introducing it is talking about it being a fantasy of yours. Any partner worth their salt should never shame you for your fantasies and might be curious about knowing more. That’s the first step in talking about it. Obviously the ideal would be a partner who responds “oh my god, that’s one of my top fantasies as well, let’s do it!” But that’s not always the case.
You might also have a very open minded partner who is happy to try it out and see if they like it - which is how Slave D and I approached it after he warmed up to the idea. (His own judicial application of femdom pegging porn didn’t hurt either!)
But the biggest and most important part of this is to have an enthusiastic partner. A partner who is only doing it for you might sound noble and thoughtful, but pegging is intimate in so many ways. You’re touching a butthole! If they’re not into it, they might risk hurting themselves (more on that in the prep section) or also hurting your feelings/desire to peg again. It’s a big mental boner deflater to feel your partner isn’t into what you’re doing.
Getting into it
Get your mind out of the gutter and into the details! You might think that once you’ve agreed to the strap, that’s you done and dusted - but there’s some things we think you should chat through so there’s no surprises during sex.
Have you checked your butthole?
This is a two-for-one question! For the peggee party, have they ever touched their anus during masturbation or had someone touch it before? Are they comfortable with you touching them without any further sexual intent? This can be a good exercise for you both as it’ll give you a sense of the sensations and how it makes you both feel.
Secondly, if the peggee isn’t aware, how do they feel about touching their butthole? Do they think they might like to try fingering themselves first (with or without their partner there), do they want you to finger them before pegging, how do they feel about possibly using a douche?
Talking about anal sex can get folks a bit flustered, but relax and just be curious! If you’re both willing to try pegging, getting comfortable talking about it is really helpful and also can also turn into something really hot if you both enjoy it. You’d be amazed at how talking about pegging prep can become its own form of dirty talk because it builds the anticipation in you both.
Fingers, Tongues or Plugs?
No, this isn’t a weird sex version of Fuck, Marry, Kill. If you’ve chatted about fingering, then let’s talk about other anal stimulation and prep. How do you both feel about butt plugs? If you’re the peggee who hasn’t been pegged before - why not think of incorporating it into your other horizontal hobbies?
For example, why not try out both of you wearing buttplugs during sex and see how you both feel? If you’re both really into it, then maybe the pegger can also wear a buttplug as they peg to have even more stimulation.
Then what about rimming? This absolutely is not everyone’s bag - and that’s entirely fair, but don’t make assumptions about what the other person might be into. Some people are really into anal play and pegging but absolutely do not want anyone’s mouth near their butt. Other people swear by rimming as their favourite foreplay activity for pegging specifically. If you’ve got concerns about errant hairs being caught in your mouth or want to practice safe sex - you can use a dental dam or cut a condom open and use it as a barrier so you’re not directly mouth-to-ass if that feels too intense.
The Poop Conundrum
You need to talk about this, as shit literally happens. This might not be a big chat - some couples are extremely open in discussing their bowel habits or they might have kids and therefore poo doesn’t bother them in the slightest.
On the other side, you might feel super awkward if there is poop on a condom or dildo after pegging. Say so! You might agree to just dispose of the condom without looking at it too closely or put your dildos into the sink or shower to wash straight after play. But it’s worth becoming comfortable with the knowledge that maybe you might see or smell poop at some point during your pegging play.
Also, maybe just talk through what happens if there is an unexpected poo-nami. Slave D and I had a very memorable experience the first thing we used a fucking machine and despite cleaning, the dynamic efforts of the machine plus the vibrations were more than his butt were used to and there was poop.
My recommendation is always to laugh about it because these things happen, they make you closer in some ways - but make sure you know that’s the right approach as maybe one partner will feel they’re being laughed at, or being mocked (for pooping or being pooped upon).
Positions
You don’t need to plan with military precision and timings, but if this has come from a fantasy - talk that through. Did one of you imagine the peggee being on all fours, moaning into their arms as they’re being railed whilst the other is thinking of some more slow and tender face-to-face fucking? How does the peggee feel about being on top - they can control the dildo better and how much they can take, but if you’re not used to being on top, it can feel a little scary and vulnerable.
If you’re not sure at all what positions to try, then fret not as we’ve covered a whole bunch in our illustrated guide. Why not have that open and talk together about which positions you want to try first?
When?
Again, no need for military precision and having a clipboard or gantt chart at the ready. But if it’s your first time pegging or being pegged, then don’t assume it’s going to be “wham bam, thank you ma’am”. There’s more prep involved and first times shouldn’t be rushed. So try to make sure you have a few hours where you’re alone together, there’s no housemates or children or nosey neighbours who might interrupt you or some dinner appointment you need to make later that night.
We don’t have to get our rocks off to have a good time, oh no.
Oooooh coming in with a contentious statement here! But one worth considering - especially if you’re used to having sex that crescendos in an orgasm. Hear me out, not all sex needs to have orgasms in it - sometimes sex is just great because you’re getting pleasure with no intention or end-goal in mind.
Also, some people might find it hard or even impossible to come through anal play. For people with penises, if you’re not used to being pegged, the sensation of being ‘filled’ can take some time to adjust to and might not give you the stimulation you need in order to orgasm. And then, on the contrary, there are some people who find that anal orgasms - or assgasms as we’ve seen them called online - are completely achievable.
This is a conversation that should filter through into your actual pegging, because the peggee might want to get off, but find that actually having their genitals touched as well as being filled with the dildo feels too much or overwhelming.
Try some things out, and talk to each other. We find that after building up and pegging for a little while, it’s much easier for Slave D to recognise if he’ll be able to come from being pegged or when he feels stimulated enough to want me to help him finish.
It could be that you keep the acts entirely separate as well, and peg for the fun of pegging but then both orgasm after your strap time is done.
To kink or not to kink?
If you’re a regular visitor to our site (hi there!), then you might already be kinkily minded, if not actively incorporating kink into your sex life. We support and celebrate you. Yet, if you’ve not tried pegging before, it’s worth considering if you want to go into it including all the “bells and whistles” (I do mean incorporating other kink acts, but if you want to literally include bells and whistles, you do you.)
This should be relatively common practice about negotiating and understanding your wants, desires and limits with kink play, but discuss them again for your first time pegging. Questions like do you want to be restrained, do you want me to talk dirty to you or humiliate you during pegging? How do you feel about sucking the dildo before we peg?
Open conversations before you get into the act can also help create the best experience for both of you, if you know what the other person fantasises about, what the right things to say are and how they want to be treated when they take the strap.
Under lock and key
Surely you didn’t expect a House of Denial guide without us talking about discussing our favourite topic, chastity!
Chastity and pegging go hand-in-hand to us (or should that be cock in cage?) and we’ve mentioned it in our favourite pegging-compatible kinks section (spoiler alert!). If you are in chastity, but introducing pegging into your intimate life - what does that look like? Will they be caged for the first experience or not caged at all during any pegging?
Depending on your dynamic, make sure you also go over safewords or check-in words/actions in case the experience of being caged is painful or taking away from the experience. It can take some adjusting to wearing a cage whilst being pegged, if that’s what you want to do, which just gives you a great reason to do it more often. Oh no, we have homework to do, what a shame…(!)
Keep the conversation going: checking in
The pegging conversations shouldn’t stop with negotiations, but be the start of a fluid conversation-and-check-in that continues into the pegging - and beyond.
Remember that you’re in this together, so you need to check in a lot during your first pegging sessions. It’s not any commentary on your skills or being patronising or cautious - you’re learning together.
Go slow, take your time, don’t be afraid to use more lube or ask for more. If something doesn’t feel good for either of you, you need to say so. If something feels uncomfortable, stop for a moment and adjust or reassess. Some people can find that if they are pegged for too long, their skin becomes sensitive or even is at a greater risk of tearing - so listen to your body (peggee) or check them out if they’re saying it’s getting tender (pegger).
Plus, if it isn’t working for you both, sometimes it’s best to stop and try again at a later time. No one is a world champion at things the first time they try it - learn, listen, readjust, try again.
Then, after pegging has occurred and you’re lying together in a sweaty, tangled heap, guess what - it’s time for another check in. Checking in and going over how things went is an important part of aftercare.
The trilogy of pegging chats; the aftermath.
Aftercare is a crucial part of pegging play - so much so that we ended our guide with it!
After all is said and done, talk to each other again about how you felt. Was it what you imagined? Did it feel better or worse or more than you had anticipated? Were there any comedic mishaps to giggle through or unfortunate cramp episodes or position changes that you did? All of these conversations and feedback help you both discover what you enjoy and help you get better at verbalising it.
You might also find that your partner sees something you didn’t even realise - Slave D told me how he knew I was really into pegging (wouldn’t you like to know that particular tell!) and by the same token, I’ve spotted little physical signs of when a position is or isn’t working for him which we’ve chatted about later.
Hi-ho, is it time to find our pegging kit we go?
And there you have it folks - a trio of conversations with some prompts to help you talk about before, during and after pegging. Will this feel a bit awkward if you’ve never talked about buttholes before with a partner or potential partner? For sure it will do, but it’s also such an exciting opportunity to learn more about each other and become closer and have great pegging sex together.
Talk lots, and keep talking even if pegging becomes a regular part of your life - there’s always something to adjust or try or experiment with!
So now, it’s time to start compiling your dream pegging kit.
ABOUT THE AUTHOR
Mistress K
Mistress K (she/her) is a queer kinky woman and in a long-term chastity-led relationship with Slave D, the other half of the dynamic duo who run House of Denial.
Thoughtfully dedicated to consent-led BDSM practices and interactions, Mistress K supports our community via our customer service channels (does that make her a service top domme?) by engaging with anyone interested, enthusiastic or curious about chastity.
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