Since role-playing makes you pretty vulnerable, do this with a partner that you can really trust. But don’t be afraid to challenge yourself and push yourself beyond your comfort zone.
Start by talking to your partner about the idea. Ask her if she’s ever had a fantasy, like did she want to be seduced by the head cheerleader, be thrown in a cell with a bunch of tough female inmates or be a navy captain with a girl in every port? Admitting these kinds of things can be hard for someone who is shy, so you might want to start things off by sharing a fantasy of your own.
Think About Your RoleIf she seems up for it, make a date for your role-playing adventure. Spend some time thinking or researching the role you’re going to play. Work on your pirate accent or shopping for a school girl costume. Dressing up is half the fun, so visit a costume shop (Halloween is a good time to shop for outfits.) or a second-had store.
Before you begin, talk about how you would like the scene to go. Is it going to end in sex? Will you stay in your roles during sex, or is the fantasy just to get things started? Agree to the scene and don’t push her to do anything she is uncomfortable with. Set your own limits too.
Set Ground RulesSet some ground rules, like no criticizing the other's acting skills and either of you can end the game at any time if you feel uncomfortable. Add other grounds rules that feel appropriate to you both.
Be creative. The whole idea behind role-playing is that it’s supposed to be fun. Set the scene. If you’re playing doctor and nurse, wear lab coats, white sheets on the bed and bring in some toy stethoscopes and band aids.
Set the Scene
Don't just think of characters, but think of a scene. Are you an explorer landing on a deserted island? Did your cable go out and you had to call a repair woman? Don’t be afraid to play around with gender. Maybe you’ve always wondered what it would be like to be a gay or straight man. Go ahead and let your inhibitions down and enjoy the experience.
Like any kind of new activity, it might not go exactly smoothly the first time around. Be patient with one another, talk about what worked and what didn’t work and how you would improve your scene for the next time you play.