Wear whatever, pool is pool. Don't think so much about what to wear, just go have fun, talk about stuff while playing, joke about how you gona crush him, do a small bet that if you win he must... or if he wins you must... If he wins tell him you let him and you will beat him the next time. As I said just have fun, don't think so much about th chlothing.
Slutty low cut blouse, see down it when leaning over making shots dress/cutoffs ride up when leaning over to expose lower buns RED lipstick, display pouty lips (oral expert) Highest heels that make calves most sexy
Trying to fit in Almost tight blouse/sweater, no see um Slacks but could be jeans, not TOO tight Lower heels but don't have to be flats.. again, making calves look ideal is A-OK Polish long nails match lipstick, nice large earrings, hair must NOT get in the way but must be a sexy mane