He’ll be painfully self-conscious at first, but tan lines on a sissy are quite cute. Don’t let him squirm his way out with a one piece! A bikini is de riguer for your sissy—the more revealing and playful, the better. Bikini beauties are eyecandy for the boys on the beach.
Tip: Every time a boy gives him the eye, tell him to stand up, count to twenty, and stretch his legs and arms in that boy’s direction. It will get him used to the concept of posing for male eyes. Prompt him with cues to smile and wink.