22 Pirate and Captive Maiden

You can play your own version of Captain Jack Sparrow with this role-playing game—just get ready to capture the bootie!

The Sexy Setup

Tell your lover you have a swashbuckling game in mind: You’re going to be the pirate and she gets to play the captive maiden. If she’s willing, ask her to dress in a maiden’s outfit, like a dress with a low-cut top, plenty of jewelry, and a full skirt (with no undergarments!).

Rules & Tools

You need to dress like a pirate for this game, whether that means buying a costume or making your own. Take your inspiration from books and movies: Wrap your head in a bandanna, darken your eyes, put on a big white shirt unbuttoned to your waist, slip into your tightest pants, and put on your seafaring boots. Collect your props, such as an eye patch, a hook for a hand, or a toy parrot on your shoulder.

Playing the Game

Sweet and safe: Open the game with this line: “Ahoy, mates! Keep your hands off the Captain’s maiden!” Then pretend you’re protecting her from a room full of leering faces and dozens of hands by pulling her onto your lap, stroking her hair, and kissing her bosom.

Reach under her skirt and secretly pleasure her while the other pirates continue drinking, eating, and making noise. She’s your captive, but you’re her protector!

Hot and spicy: This time she’s your captive, but you’re the horny pirate who’s been at sea far too long. It’s been months since you’ve seen a woman, let alone touched one, and she’s beautiful to boot. Tie her hands behind her back and manhandle her breasts, or rip off her dress and tie her naked to a chair for your viewing pleasure. Tease her breasts and nipples with your lips and mouth until she’s wet, then pull her hair and kiss her roughly. Take her any way you want—you’re the captain of this boat!

Up the Ante

• If your lover is willing, make her your sex slave. Rip her clothes off, then make her perform all the duties of a captive maiden completely naked. That might include hoisting the sails (removing your clothing), walking the plank (sucking you off), and swabbing the deck (cleaning up the mess!).