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There’s a recurring plotline in Modern Family, where Phil and Claire Dunphy go to a local hotel each Valentine’s Day and pretend to be suave strangers cheating on their spouses. Their attempts often go awry, such as Claire’s coat getting jammed in the hotel escalator when she has nothing on under it or Phil going to the wrong hotel room, but the couple still manages to slip in some hot, steamy sex somewhere along the way. 

How these events unfold may be a bit more extreme than in your average sexcapade, but Modern Family captures an essential truth about roleplay. Roleplay can be an incredibly hot, deeply satisfying experience...that also has the potential to be deeply embarrassing. Sometimes the fantasies that seem so enticing in our head don’t quite work out the way we hoped. 

Good intimacy has lots of room for making mistakes and iterating on what we’ve already tried, but sometimes you need to go beyond the platitudes about communicating and creating a judgment-free zone and actually work on your skills.

Yes, you should absolutely talk to your partner about your fantasies. Yes, you should be communicating before, during, and after, but you can get that advice from any sex-positive blog.

Today, we're going to focus exclusively on roleplay and teach you how to play without embarrassment. If you follow these methods, you’ll be roleplaying like a pro in no time.


Step 1: Play outside the bedroom 

Roleplay is a lot like acting, but more specifically, roleplay is a lot like improv. You are constantly trying to offer up your partner juicy bits to build on and make something interesting out of what they give you. It’s collaborative storytelling where the two of you are both the audience and the players. 

In improv, the assignment is to try a bunch of things and find what’s funny. In roleplay, the assignment is to try a bunch of things and find what’s sexy. But sometimes these goals can cross over, especially since maintaining a sense of humor in the bedroom is a great way to recover when the tip slips out or someone passes nasty gas.

Rather than suggest that you take an improv class at your local community center, it’s important to realize that you will (likely) only ever have an audience of two for your roleplay. And both of those people will be available for practice quite often.

So, with all of these comparisons to acting, is it important that you’re a great or even half-decent actor? Hell, no! 

What’s important is that you develop a sense of chemistry and playfulness with the person you're intimate with. This is an excellent goal even if you have no interest in roleplay. A little banter and a few impromptu bits can prevent a long-lasting marriage from turning into a roommate situation. 

If you naturally have this kind of dynamic with your person, fantastic! If not, never fear.

Much like a muscle, our sense of play can be exercised. Kids play all the time, but as adults, we worry about looking foolish or wasting our precious time. But what's the point of life if not to be thoroughly enjoyed?

There are many ways to cultivate play in our relationships. One suggestion is to turn a conversation about one thing into another. For example, instead of letting the other person know that they left crumbs on the table, get their attention and pretend to be a detective looking for the crumb culprit. If they’re receptive, they can play along and pretend to be a cagey suspect. 

Even if they don’t jump right in with you, if it makes them laugh, pat yourself on the back for stepping out of your comfort zone and getting a positive response. You don’t have to go on and on about crumbs, you’re just inserting a little flavor to the mundane. 

This exercise can also help teach you about timing - another essential aspect of sexcapades. When is your partner in the mood for this kind of thing? Does it help to cheer them up when they’re down or is that a time where they need you to be serious? Much like consent, you can never go wrong with asking directly, but it will serve you well to learn to read the room - and your partner.


Step 2: Dirty Talk + Imagination

For the purposes of this guide, we'll assume that you’ve already started talking with your partner about the stuff you’re into. Now, it’s time to incorporate some of those fantasies into your dirty talk. 

A lot of dirty talk is observational, “I love it when you touch me there,” or “you’re a good girl, aren’t you?” To move things in the roleplay direction, focus on the more imaginative things you fantasize about when you masturbate. Is it Scottish highlanders? Gruff kidnappers? 

Bringing up our deepest fantasies during sex can feel more vulnerable than saying, “I want to see you covered in my cum,” because being turned on by something that’s inherently sexual feels normal, whereas sexualizing something that exists outside that sphere feels like perversion. Even if we wouldn’t feel the slightest hint of shame over a Sarah J. Maas book, bringing that into our current sexual reality can still be a lift.

The goal here is to eventually start saying a few things in-character. Instead of, “it would be really hot if you were a priest and I was going to confession,” you can say, “Forgive me father for I have sinned.” 

Again, both are great, and you may want to open with that first one, but when you speak in a hypothetical, you are still distancing yourself. When you say it in the first person, you’re one step closer to acting, which is one step closer to roleplay - and one step more vulnerable in front of your partner.

You’re also giving your partner the opportunity to be a part of your fantasies thereby increasing your attraction to them. Even if you’re just doing it in the missionary position, I guarantee you that if they respond with, “Confess, my child,” it’s going to heighten the experience.

Remember, the verbal play doesn't have to last a long time, but it’s a low stress way to get used to being in a roleplay mindset while having sex.

Afterward, make sure to tell your partner anything that they said that really turned you on. They’re also probably throwing things at the dart board and seeing what sticks.

If there was something that they said that killed the moment, you may also want to share that, but be gentle. It can be discouraging to put yourself out there for your partner and not have it be received well. We tend to remember the negative things that are said much more strongly than the positive things. However, the last thing you want is for your partner to go through all that effort and still fall short because you never told them that being called “little girl” is a hard pass for you.

Step 3: Change your look (slightly)

A short skirt and a work blouse can become a secretary outfit. A string of pearls can signify your status as a wealthy heiress.

This isn’t a masquerade ball. It doesn’t take much to transform a simple prop into an effective roleplay costume. Even the most authentic version of the character you’re portraying would likely end up naked by the end of the night, so in some ways you’re just fast forwarding things a bit.

There are two main things to pay attention to in this stage. Firstly, the idea that a small touch can help imaginations to run wild and make it soooo much better. Secondly, the idea that dressing up for each other is a way to woo your partner and continue to try to impress them.

Now, admittedly women have it much easier in this phase, a challenge that we come across all the time when designing the adventures for Saturday Box. There are many different styles of lingerie that can evoke a historical era and accentuate the female form at the same time. There are hair pieces and accessories and jewelry that can add just the right amount flair.

Men have it a lot tougher since men’s fashion is a lot narrower, and many of the male “characters” dress relatively similar or would require pieces that you're less likely to have on hand. Sometimes it feels like your options are full costume or bust. 

In a roleplay, it’s totally fine if only one person is dressed up, but the act of dressing up even if you’re not wearing something much different than what you’d wear to work can still be that much more special because you’re putting in the effort. It's an aesthetically pleasing gift.

Depending on what you’re wearing, you can decide how much of it to keep on during sex, but try to add in the verbal banter even if it has nothing to do with what you’re actually doing. It may be easier to imagine yourself as that character when you're dressed for the part, but if it feels awkward, you may have to build up to it. 

On the plus side, even if you aren’t doing much in the way of roleplay, it can just be nice to see each other in a different outfit.


Step 4: Design a roleplay scenario

The hardest part about roleplay is not knowing what to do next. This is when we’re most likely to freeze like a deer in the headlight or laugh nervously. So, here is where we take everything we learned so far and bring it together. 

Start with a fantasy that you explored in Step 2 or Step 3. Think about how that fantasy become a setup for spicy fun. (For both kink and roleplay, this is often referred to as a “scene.”) 

If you’ve discovered that the schoolgirl/teacher fantasy really turns you on, maybe you could have the “teacher” discipline you for being late. If you can't get enough of Orange is the New Black, have someone arrest you and take you into "jail".

A little bit of planning can go a long way, because it can be hard to think of creative things to say or do in the moment. You also want both people on the same page about what to expect so they can stay present during the roleplay.

When choosing a scene or activity, it helps for both “characters” to have some kind of motivation or goal. It doesn't have to be elaborate. It can be as simple as one person trying to chase the other person around the house and the other person trying to not get caught. 

You can build up to more exciting and interesting roleplays over time, but be warned, planning and prepping for a big roleplay can be a lot of work. 

That’s why we created Saturday Box, so that kink and roleplay could become a regular part of your sex life. Our curated adventures are preplanned and include everything you need to fulfill your fantasies from themed lingerie to character cards and activities. If you liked this roleplay guide, we’re pretty sure you’ll like our boxes. 

Our super sensual Office Romance box is all about the boss/secretary fantasy, and it’s a great way to embark on your roleplay journey. Our next box, coming out in July, will be focused on a spy and interrogator. Both are a great chance to level up your roleplay game and practice everything you’ve learned so far. 

There’s no right or wrong way to roleplay, and it’s important to focus on what feels comfortable and authentic to you. Celebrate putting yourself out there, and trying something new. 

Happy playing!

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