[DanB]

I was once dared to cum 3 times in a row. There was no way I could do that normally, so I had to ruin the first 2 orgasms. Best strategy for someone who hasn't done that before starts with getting right to the edge. Then use one finger to lightly stroke the spot on the underside of your penis just below the head. As soon as you feel yourself start to ejaculate, take the finger away. This is much easier than trying to stroke all the way to orgasm and take your hands away at the last second.