Pick a position. The classic 'you've been a naughty boy' pose is him bent over your knee. But you could also have him stand, lie face down on the bed or kneeling on all fours (save that last one for later, though, since it can feel a bit threatening for a first time).
The more fat and muscle a body part has, the harder a strike it can handle. Since the idea of playful spanking is to cause 'pleasant' pain but no damage, those fleshy, gorgeous orbs known as the buttocks are the obvious place to start.
Start with your hand for the first spanking session. If you both enjoy it, then you can move onto soft whips, riding crops or paddles. Don't forget to remove any rings or bracelets, though, and use a pumice stone to remove any rough spots on your hands.
Decide how long you want the session to last. The longer the session is, the lighter the slaps. Intense spanking should be done only for a short period of time.
Wait until he's aroused before attempting your first spank as he'll be far more receptive to erotic pain. So do a lot of kissing and fondling first and run your fingers lightly over his buttocks. Then place one hand on a buttock cheek, the other on the genitals. Start with the cheek closest to you.
Your first spank should be more like a caress than a slap. Cup your hand slightly, keep your fingers together and spank in a slightly upward motion. Massage the area for a few seconds afterward and fondle his genitals afterward.
Does he look intrigued? Try another spank, then another one and another one about three to five seconds apart. Vary the weight, frequency and placement of the slaps.
Now bring out the props you so cleverly hid near the bed: a satin or furry glove or the back of a hairbrush, for example.

If you both enjoyed the session, take a trip to a reputable sex shop (or go online) for some implements. Riding crops are an excellent addition to your toy box. They're good for light or heavy strokes and make a sinister swish and slapping sound, which is a nice touch during fantasy scenarios. They look sexy and they're inexpensive.

You'll also find an array of whips. Rubber whips look fierce but are incredibly soft. If you want more, choose one made of soft, light leather. Both soft whips and crops are great for teasing. Have him gently poke the tip of the crop against your clitoris or brush the strands of the whip across his thighs. Paddles, broad, hard instruments, are for true devotees. They cause much more pain, and it's hard to judge how hard you're hitting when using one.

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