Ask the Master of the Extraordinary – A Scared Boyfriend

I have gotten stupid emails from you idiots before but this is easily the dumbest one that I have ever received: 

Dear Master of the Extraordinary, 

Your site is great, bro. I think ya’ll are real funny. Congratulations and keep up the good work! So listen, like, I’m in a bit of a pickle here. You see, I have this fantastic girlfriend; she’s real hot. I mean like smokin’. Trouble is there is something she doesn’t know about me. You see, I may have kind of done some porn or something when I was younger.  Nothing too big, you know. Just a little bit of guy-on-guy action.  Anyways, it was a tough time in my life and I’m not proud of it but it happened. However, it’s over now and I’m a bigger man for it.

So I wanted to ask, should I tell her about my past?  We’ve been a lot more open with each other lately. But I just don’t know how she would take it. If I don’t tell her, I’m also afraid she might accidentally run into some of my videos online. Am I being paranoid? I just don’t want to lose her.


A Scared Boyfriend


Dear Scared Boyfriend,

Congratulations! You have just received the Master of the Extraordinary’s first ever I’m a Huge Dumbass Award. Please give us a forwarding address where we can send you the prize. Otherwise you can come down to our office on 123 I’m a Moron Street to pick it up.

How does it feel? Are you going to take your family to Disney World?  Oh, right…. I forgot.

Have you ever considered getting plastic surgery and changing your name? I mean if the internet already knows, it’s only a matter of time before everybody else finds out. Or you could always just settle for a career as a porn star; there’s no such thing as bad publicity (or so they say…). But if you really want to stay with your girlfriend there is only one solution. Offer to have a threesome with her and another guy before you tell her. She’ll be in such a good mood that you’ll be able to tell her anything.


The Master of the Extraordinary

And remember if you too want to tell me about your stupid problems, I can be reached at

– The Master of the Extraordinary


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