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Take him to the corvette dealer and get a pic of him holding the door open, he'll like that. ?? heck even holding a motrocycle like he's going to ride might be kewl, if he's into those kinds of things
Does he have a sport? maybe one doing something sporty, hell even fishing would be OK, or standing in the dugout door
Gotta get one of him humping a statue just for blackmail later. and one by a nice staue plain
Porch swings or brick steps are good ideas
Fancy wrought iron gates is a good backdrop, as is a stone wall, or a water fall
Heck his guitar and a cool backdrop would work, or playing the guitar sitting on some old steps or a beat up porch would be artsy
Hanging on a farm fence would be kewl too, like where they have horses
a pic outside the local teen hangout might be kewl, even a drive in with him in the car and a try at the window might be nice
comming down the slide at the park arms up like it's a "big' ride might work
If he has a letttermans jacket, a pic of that at the back drop or leaning on the pole of the field goal might work
against a wall with kewl graffitti, or by and antique coke machine, or a piece of art at the museum
him reading from a distance with his back against a tree might work

Do you have a professional photog in your city that has some "scenes" set up on the outside, we do and you can sneak over there on a Sunday morning and use the scenes to take pics, they have an arbor a bench a little brook with a bridge and a plain brick wall