Sydney opens up to you about one of her co-workers who's been bragging about how good he is in bed. She seems a little upset about his attitude and the nerve he has to even make statements like that. Part of her wants to just put him in his place and show everyone what kind of asshole he is. The other part of her is curious. Sydney ends up making a bet with him that if he makes her cum first, he gets to take her on a vacation. If he cums first, he'll pay for a vacation for you and Sydney. You don't like the idea but Sydney manages to convince you by giving you a little jerk off instruction. You can't refuse and finally you reluctantly agree. A vacation with Sydney does sound nice after all - and she keeps reassuring you it's a sure bet. But then it happens. You watch Sydney get fucked by the challenger. And it turns out it's not a sure bet after all.
8 min 39 s 1080p