Try first making a list of his interests, and do each month based on that.

For example, if he is a baseball fan and the baseball season starts in April (I'm just guessing at that, I have no real idea) a photo of yourself in a long baseball shirt may be good for that month. Sling a bat over your shoulder and you've got a good prop. If you want to go more toward the risque (and you are of legal age for more risque shots!) wear a swimsuit bottom with the baseball shirt.