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Let me think.
One time, I saw a really kinky black escort who made me cum twice. Booked two hours, she sucked one out, we goofed around, then she got another out of me.
But I'm really a one-shot guy. She worked it too hard the second time and it was a poor orgasm.
So with that said, I'd say 2 or 3, but really the high point was when Koutetsu no Majo Annerose ep 1 came out. The cumshots are INCREDIBLE and its totally fetish. I must've fapped like 5 times in 48 hours.
I kinda envy guys who can do it twice or multiple times in a day. I get major diminishing returns just fapping once a day.