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 said one of her male co-workers is a total arrogant jerk, and constantly brags about being good in bed, and she actually feels the need to take him down a peg. You ask her what that means and she tells you well she actually 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 you by letting you jerk off for her, she gets you to agree. You do know how good she is in bed and how she'll likely have him cumming in less than a minute and well, it IS a full paid vacation. Well they end up getting together and she makes you watch even. It looks like she's got 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 bet that you both thought it was!