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Cuckold Cum Competition – Me VS an Employee at the Office

April 3, 2026

I constantly stop by her office, hitting on her, and trying to take her on dates. I know full well that she has a boyfriend, but I don't care at all. She knows I'm better looking, and loaded. She also knows I am constantly fucking the other girls around the office. Eventually I overhear that her boyfriend and I are having a hard time paying their rent. So I pitch a bet, on who can cum first. If I wins, she goes on a date with me. If she wins, I pay their rent for a whole year. The kicker being, her boyfriend has to watch the whole thing as a witness. She finally convinces her boyfriend, and she's secretly glad; because she has really always wanted to fuck me (I knew it).