Milo grinned at her response and as she played with his shirt. Ah, how he had already wanted and longed to include this strange, new woman in a part of his life that he had enjoyed on his own. He could sense the potential in her, he could practically taste the fun. But his seafaring abilities were sort of a special aspect of Milo's strange, twisted life, and they could not be exploited on a woman who wanted to remain a booty call. He would not assume her intention, but he could not assume she wished to be a regular visitor of his either.
So he tilted his head and said, "Well, I may or may not have access to a bona fide pirate ship." So it was a small cargo ship, it looked like a pirate ship if you put a pirate flag on it. "And if you can prove yourself to be a proper sailor, you can become my first mate." He grinned wider, excited by the idea of proposing a challenge. So excited he was that he had not even thought up the particulars when he said, "You have to pass three pirate tests, and I'll take you on the boat ride of a lifetime during the next weekend you have free."