As always I enjoyed this. As you know from reading my posts I have many a time spanked multiple boys at the same sitting as you said, well, one after the other.
The most that I have spanked at one time is 5, it was a sleepover Donny was having, there was Donny who was 9 almost 10 the rest of the boys were 9 if I remember correctly. I caught them throwing rocks over my fence at my best friend Helen's house, thankfully they didn't hit it.
With three boys then add their friends spending a good deal of time here, over the years I have many many times spanked 2, 3 and 4 at a time. I will bare them all before I start to spank. They are all so close in age I didn't save the youngest for last, I would just grab who was closest and take him over my lap then continue that same way, but if I thought a lesson had to be learned and one of my boys was the ringleader so to speak then I would make him wait and have to watch and hear the others being spanked.
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