The longest I went was a threesome. It took about four hours to bust the first nut. One of the women was hot and the other (her girlfriend) gave great head. I think I was probably experiencing "Retarded Ejaculation." Most women don't want four hours of vaginal penetration. With my wife bare I would nut in less than 30 minutes or so. However, in a condom with strange, not so fast. I'm hypersexual and was screwing several new women every week. I would nut with one chick and a couple hours later I'd be looking for another.