1920 x 1080p HD — You know I never back down from a challenge, even if it means you get a little jealous. Your girlfriend Sydney confesses something a little odd to you. She says one of her male coworkers is a total arrogant jerk and constantly brags about being good in bed, and she feels the need to put him in his place. You ask what she means, and she tells you she made him a bet. She’ll fuck him, and if he can make her cum, she’ll go on vacation with him, but if she makes him cum first, he’ll pay for a vacation for you two. You really don’t like the sound of this, but after a bit of convincing by letting you jerk off for her, she gets you to agree. You know how good she is in bed and how likely it is that she’ll have him cumming in less than a minute, and well, it is a fully paid vacation. But then they end up together and she even makes you watch. It looks like she has him right where she wants him, but then you notice she’s actually starting to enjoy herself, and it makes you uneasy. This might not be the sure thing you both thought it was!