A good friend of mine helped me fuck my wife (then girlfriend) on several occasions. On one of those occasions, we both managed to penetrate her pussy at the same time. And yes, we both came inside of her. I can't recall our exact positions, but I do remember her moaning with pleasure. That happened about 10 years ago (or more). To this day she still enjoys riding a dildo while I slip into her from behind. The sensation of her wet pussy and pulsing dildo usually makes me cum incredibly fast. I would say try it!
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