My No-Sex-Having Friend’s Encounter With A Hooker

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I have a friend who has been, putting delicately, single for a very long time. How long? He struck out with Eve, and hasn’t gotten a date since.

Eve was this super hot religious chick he went to high school with. Recently, he ran into Eve again at some book signing thing for an ex-Fox News anchor in the student union. She got a few more blemishes on her apple over the years, but she was still good enough to sin for. In a matter of speaking. They started dating, and now her folks were pushing them to settle down. My friend was trying to do a little pushing of his own, but Eve was pretty insistent they stick to business the biblical way.

Facing the premature end of his wandering days, and afraid of being pre-mature with a stunner like Eve, my friend decided to get with a hooker.

He came to me for advice. I’ve done a lot of dumb stuff in my life, but that’s one road I’ve never been down before. Naturally, I went straight to our group chat:

Cortez: He needs to do some research. You can’t go into this shit blind. That’s how you get gonorrhea.

Lars: Is this a bucket list thing, or has it just been a while?

Cortez: It’s been awhile. And also the bucket list.

Barnes: I get it. It’s the last chance to be a little wild, pre-marrying the Jesus Camp girl.

Brent: We could take him to Vegas, get the $12.99 special.

Barnes: The what?

Brent: You know those trucks that drive around with pictures of women on them?

Cortez: What kind of hooker can you get for $12.99?

Brent: I told him you can go to a strip club and get motor-butted for $12.99. He wasn’t into that. He wants a hooker.

Me: He says he wants to spend less than $1000 on a hooker.

Barnes: $1,000 dollars?! He could get a $600 flight to Amsterdam, a $200 hotel and still get four hookers. They’re only about $50 there. Hot, clean, and all legal.

Cortez: I think even in America you can get three decent hookers for $1,000.

Brent: He should just ditch the religious chick and stick with hookers.

Lars: This is going to end badly…

As you can see, none of us knew what we were talking about. Except maybe Barnes, who did study abroad in Holland for awhile. My friend ended up going on an incredibly sketchy classifieds website and clicking around until he found someone he liked.

I asked him if he was really going to go through with this. My friend nodded excitedly and told me that for an extra $75, the girl’s ad mentioned he could take an expedition up her poop shoot.

He messaged her, agreed on a price, and tried to go meet at a motel by the highway. He waited there for two hours before she messages him saying she had to go pick up her kid.

Barnes: That’s not a red flag. That’s a fucking air raid siren.

Brent: She probably didn’t like the motel he picked. You need to take a hooker to a Hilton or a Marriott at least. It’s like going out to a restaurant and not tipping.

Barnes: Getting the tip is the important thing in this situation.

Cortez: Honestly, I feel for the guy. Maybe marriage is his only shot to get some action.

Lars: Poor customer service on the hooker’s part.

My friend wasn’t deterred, however, and tried again the next weekend. The hooker’s name was Lisa Mercedes, but she drove a Jetta. He met her at an Olive Garden, where they shared bottomless soup and breadsticks. According to my friend, she ate like she was pregnant with King Kong, and still took a massive to-go bag at the end of the meal.

Cortez Does the “don’t eat like a horse” rule for first date etiquette apply to hookers? Or it more like a business lunch?

Brent: Tapeworms. I’ve seen it before.

They went over to the Courtyard Marriott (Brent’s suggestion) and put the “Do Not Disturb” sign on the door. Apparently, she was very professional. She brought lube, toys, and antibacterial cleaning products. Even the handcuffs had soft felt comfort linings.

My friend was actually having a pretty good time and didn’t regret his decision at all. He looked into Lisa’s eyes and saw a strange sort of beauty. It was like looking into grand, ancient mansion fallen into disrepair, covered with vines and crawling with termites. Like there was a deep purity and perfection that he could tame, that he could save and bring back. Lisa stared back, and there was a light that erupted between them. He didn’t even resist the handcuffs as she fastened him to the bed frame. He could see a life with her, raising her kid. She smiled back and he knew she felt the same. They would be married within a year, and the ceremony was so beautiful and touching, I couldn’t help from crying as I thought about how love springs from strange and mysterious places.

Just kidding. She robbed him.

Brent: Yeah, after the hooker cuffed him to the bed, she took his wallet, keys, and drove off with his truck. Turns out the Jetta was stolen, too.

Lars: When the hotel janitor cut him out, I heard he got home and his house was cleaned out, too, because his address was on his license.

About a month later, my friend’s swab test came back positive for gonorrhea.

Cortez: See? I fucking told him. Dumbass.

Image via Shutterstock

  1. GDI Joe

    It’s gotten to the point where I don’t even care about Fail Friday anymore you fucks.

    8 years ago at 3:58 pm
      1. fratmasterII

        To be fair, I only see Fail Friday on the site and not in the app for some reason.

        8 years ago at 4:24 pm
      2. Henry_Eighth

        To see it on the app you have to log in as a user and pretend to be over 17.

        8 years ago at 4:36 pm
      3. fratsohardUn1versity

        Coach says take of your sneakers, put on your flip flops and meet him in the office in 5

        8 years ago at 7:09 pm
    1. The User Formerly Known as Frabst

      Alcohol kills any bacteria/virus. That’s at least what I tell myself.

      8 years ago at 2:57 pm
  2. Ronnie Swanson

    If my friends and I were in this completely made up situation, our group chat would be similar. That’s the 1 honest, respectable aspect to this piece.

    8 years ago at 4:14 pm