Cuckold Cum Competition - Me Versus My Boss' Douchebag Son!

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My Boss' son is constantly stopping by my office, hitting on me, and trying to take me on dates. He knows full well that I have a boyfriend, but doesn't care at all. He knows he's hot, and loaded. He is constantly fucking the other girls around the office. Eventually he overhears that my boyfriend and I are having a hard time paying our rent. He pitches a bet, on who can come first. If he wins, I go on a date with him. If I win, he pays our rent for a whole year. The kicker being, my boyfriend has to watch the whole thing as a witness. I finally convince my boyfriend, and I'm glad; because I have really always wanted to fuck this guy.

Video Transcription

Yeah, I just got home from work.

Um, you remember that guy I was telling you about, the boss's son?

Yeah, Michael.

Yeah, the one that's covered with all the tattoos, that's really fucking hot.

He's been coming in after the gym like every day, all sweaty with all his tattoos showing.

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Well, guess what this little rich fuckboy tried to say to me today?

He wants to make a bet.

Yeah.

A fucking bet that he would come- if he came first, that he would pay an entire year's worth of our rent.

I know.

He bumps the shit out of Brian, though.

Yeah, to like, solidify the deal.

Yeah, I know.

We are behind on bills, so I mean, maybe he will.

I know.

I can't believe this ***, though.

There's no fucking way I'm losing.

Yeah, oh, Brian. I think Brian just got here.

Alright, girl, I'll call you later.

Hey.

Hi.

What's going on?

Oh, you know, just talking to your girlfriend.

Nice. How was work today?

Um, it was okay.

Uh.

What?

Do you remember that *** Michael? You know, my boss's son?

Oh, yeah?

Yeah, so-

Get a second job. You don't need to fuck some rich ***.

I mean, I work like 60 hours a week.

Where do I have time to get a second job? This is ***********. One time. It would be one time.

And I have to watch you fuck that guy that has always been the biggest douche anytime I'm around.

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