The Beginner’s Guide to Roleplaying During Sex

Roleplaying during sex can be a tricky thing. It has the potential to be a hot-as-hell exploration of power dynamics through an alluring fantasy scenario. But it can also be a cheesy, bumbling cringefest. The idea that it can turn into the latter has stopped many people from trying their hand at roleplay in the first place. The possibility of awkwardness is an incredibly powerful deterrent. 

But we all deserve to have sex that’s exciting, fulfilling, and fun, and when roleplay’s done right it can definitely be all that and more. Incorporating roleplay sessions can add some spice to a sexual dynamic that’s fallen into routine, be a bonding moment in a bubbling fling, or get you off in a way that you didn’t know you needed. Whether you want to pretend to be your partner’s forbidden mistress, or that you’re both athletes in the showers after a practice, this guide can help you bring these fantasies into reality without it being awkward. 

Finding & Defining Your Desires in Roleplay 

We’re well aware that figuring out what you need and want out of sex can be a tricky, unclear process. For total beginners, you might want to try checking out our guide on exploring your sexual needs and desires. But even if you’re totally grounded in what you need and want from sex in general, roleplaying for beginners can be tricky, unfamiliar territory. Maybe you’re intrigued by the idea, but you’re not sure what exactly you want out of a roleplay session. 

Chances are you already have some idea of what people roleplay as — the repair-person fixing the pipes, the cheerleader and the football player, the masseuse and their client, the list goes on and on. A great start would be to think about these scenarios and note how you feel about them in a non-judgemental way. Try not to worry about being cheesy, or about having weird desires. We promise you that everyone’s desires are weird, which means that no one’s are. Think about what you like and don’t like from these scenarios, and what could be done to make them more suited to your wants. 

Communicating What You Want Effectively & Transparently 

As sex expert Vanessa Marin tells to Bustle, the importance of deep planning for roleplay can’t be overstated. In the interests of keeping things feeling natural and chill, you might have the impression that they also need to be spontaneous. And for those not used to it, planning sex in advance might feel awkward at first. It’s hard to talk about what you want! But trust us — setting out desires and expectations before initiating the roleplay session will make things way, way smoother. The awkwardness of mapping out a fantasy is tiny when compared to the awkwardness of trying to roleplay with someone who has no idea what you’re doing and can’t catch on. You don’t want that. 

Even worse, you definitely don’t want your partner to not be super into what you’re doing, or to play along half-heartedly. Sex is obviously best when everyone involved is invested, present, and passionate. This holds true for roleplay as well. So what do we prescribe? Have honest and transparent conversations about what you want with your partner. Get a collaborative process going around figuring out the details of the roleplay session, and encourage your partner’s excitement and active involvement. 

The other important piece of this part of the process is to make sure both you and your partner are explicitly setting your boundaries and limits. Don’t wait for your partner to bring up a concern they have about some aspect of the session; make space for any discomforts or potential anxieties to be discussed, from either you or your partner.

“We promise you that everyone’s desires are weird, which means that no one’s are.“

Roleplaying for Beginners in a Sexy & Casual Way 

There’s a hurdle you have to get through when trying roleplay for the first time. Accept the reality now: it’s probably going to feel at least a little weird at first. Maybe there will be a bit of self-consciousness or self-doubt involved in the beginning. But like they discuss in this Thrillist article, a good way to get past that is to lean into the silliness. Sex has a tendency to feel Very Serious and Very Important, which can make you take yourself really seriously. But in the end, roleplay is really just a game — albeit one that you’re trying to get off to. As a game, it’s best if you approach it with a sense of play.