Editor’s note: This question comes from the inbox of Cate Osborn, frequent Playboy contributor and Playboy Club creator.
Q: I have always secretly wanted to be pegged, but I feel weird about bringing it up with my partner. We’ve joked about it, but it’s never progressed further. How do I proceed?
Cate Osborn: Imagine it’s your birthday, and you really, really want chocolate cake with sprinkles. Your partner asks you if you want cake, and you say “that’d be great!”, but you feel weird about asking *specifically* for chocolate cake with sprinkles. You don’t want to be demanding, you don’t want to put a bunch of pressure on them, you don’t want them to feel like they HAVE to make you a chocolate cake with sprinkles, you’re just happy that they want to make you a cake at all. The next day, your partner proudly shows up with a beautiful three-layer coconut cake, and you hate coconut.
Asking for what you want is a gift of trust, and trusting your partner with the ‘ask’ is an exchange of vulnerability. You have said the ask out loud, and now, they get to respond. It’s totally normal to have fear or apprehension if the ask is new, or might be surprising, or you’re not sure how they will respond– but you will never, ever get the cake you *really* want unless you tell them about it or you’re willing to hedge your bets on maybe someday getting a chocolate cake by happenstance, but you might have to wait through a lot of vanilla and carrot cake first.
For other people, learning to talk about cake may be a matter of safety. Maybe you have a bad peanut or chocolate allergy, or maybe you carry a lot of trauma around celebrating your birthday, and certain types of cake remind you of certain bad birthday parties you’ve had. In these circumstances, providing your partner with clear and direct communication also keeps you safe, both mentally and physically.
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Now, there is a difference between asking for the type of cake you’d like and demanding cake, insisting upon cake, or forcing your partner to make you a cake even if they’ve made it clear they aren’t at all interested in baking. There is also the do-it-yourself option, if you want chocolate cake with sprinkles so badly, you can get a cake mix and make one yourself, or hire someone to make it for you. You’ve got options.
Cake metaphors aside, pegging can be a tricky topic to navigate because the wide world of butt stuff is still often stigmatized, but the truth of the matter is that all sorts of people of all genders enjoy backdoor action. My pro tip is to treat your ask with the Rule of Cake: nobody would fault you or think you’re weird for asking for chocolate cake on your birthday, asking to be pegged doesn’t have to be ‘weird’ or awkward either. It’s just another topic of conversation between you and your partner. What movie do you want to watch, what kind of cake do you want, could we try pegging sometime?
If you’re nervous about asking, sometimes it helps to talk ABOUT asking, especially in a newer relationship. “Hey, I’ve been thinking about trying something new in the bedroom- how do you like to have those conversations? Is there anything I can do or bring to make you more comfortable while we chat?”
DO NOT, gentle reader, ask in the bedroom immediately before you’re getting into things. This is a surefire way to make a partner feel pressured and on-the-spot. Your partner ALWAYS has the right to say no, or express discomfort or disinterest- however, if they make you feel belittled or like a bad person for asking, it might be time to consider integrating a couples therapist into the conversation. To stretch our cake metaphor to the breaking point, if you partner forgets to add sugar or eggs to the cake, even with the best of intentions, it may be unenjoyable, unsafe or just not very nice to enjoy. It’s important to be able to take feedback, suggestions and try different kinds of dildos…er…cake to find what works for you.
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Consider thinking about what you want to say beforehand. Sometimes it helps me to start at the “why” I want something and work backwards to the “how”: “Hey, I’ve noticed that my orgasms are particularly intense when we fool around with butt stuff, and I was thinking that pegging might be a really interesting thing to try- would that be something you’re open to?”. “I think it’s incredibly hot when I’m in more of a submissive role, and it really helps me turn off my brain– could we talk about your pegging me sometime?”
Once you’ve broached the topic, get curious with each other. “Okay, you’re interested in pegging- how often would you like to incorporate that into our sex life? …That seems like a lot to start, could we talk about maybe trying it a couple of times to get comfortable first? Do you have experience with this activity? What can I do to make you feel safer as the pegger, what I can do to make you feel safer as the pegged? What resources could we look at to make sure we’re doing this safely? Do we need to shop for sex toys or look at some ethical porn for inspiration?”
Ultimately, I can’t tell you exactly how to bring up any topic, but I want to encourage you to try. You only get one beautiful life on this planet, and if you want to spend it getting pegged, you deserve to have that opportunity. But, like many things in life, you’ll have to summon a bit of courage and use a bit of self-advocacy to get there. Try Catieosaurus’s Patented Cake Method and see what happens.
More from Cate Osborn:
Playboy Advisor: Depression is Ruining My Sex Life
Confessions of a Burnt Out Submissive Brat With a Praise Kink
A Day in the Life of a Disabled Person Who, Yes, Has Sex