The answer to this question varies greatly based on the implement you are using and the teen boy. If you are using a paddle, be weary of the force but make sure you get your point across. A red or purple butt is not a bad thing and often times teens will try to make excuses for their actions just to get out of the spanking in the short term. I believe the best way to spank a teen boy is to make him strip to his boxers or a jock and then expose just his butt. A parent should not make it awkward for the teen but it needs to be bare butt to get the point across. Sometimes boxers will suffice but a jock is the best option. Part of the ritual of a spanking is the humiliation and perhaps the best way to do this is to use his own leather belt to spank him. Some may feel bad when spanking their teen but it gets the point across so make sure it HURTS. If they don't feel it, it usually means nothing. 50+ hits is very common. Do not limit yourself to a set number of hits but hit until he is crying (for real), his butt is turning purple, and most of all when you feel you have made your point (then add a few more for god measure). Once again, this is not a sexual experience but discipline so even though he will be near naked, make sure it is clear that this is a punishment
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