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How To Spank Boys
To answer the question, I wouldn't leave briefs on him, as they have raised edges that can dig into the skin.
What clothes you have him leave on will have to take into account if you are hand spanking which might be reasonable directly on the skin, or over thin boxers.
Granddaddy's old paddle can get your message across through boxers and jeans. A safer way is to use a sweatsuit bottom or a pair of smooth shorts to put on as jeans very often have the same raised areas as briefs as well as rivets.
You have to also consider position. Don't have a boy bend over very far, as you will run the risk of striking sensitive areas. While a smaller child can be spanked over a lap, older boys might do better flat in the middle of a bed.

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