Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday and I’m dealing with wonky wifi at my in-law’s house so if there are any issues with the anonymous mailbag today, blame my mother in law. 

As always you can email your anonymous mailbag questions to, anonymity guaranteed. 

With that in mind, here we go. 


Love the anonymous mailbag, it is one of my weekly highlights.

Many moons ago in college a fraternity brother of mine was sick with stomach flu or some other bullshit. He was always one of those guys that always had some kind of cold or something. Good friend but total mama’s boy. Anyway, another buddy and I decided to go over check in on him and bring him some food. We arrive at his condo, don’t think anything of the car parked in front of his place (ooooh foreshadowing).

We knock, no response but the door is unlocked so we go in. We yell but no response so we assume he is sleeping. Of course we raid his fridge for a couple of beers and head upstairs. As we get close to his room we hear some noise, grunting and the like. Normally I would assume he was getting laid but not in his current condition. My buddy and I exchange a look but solider on.

His door is ajar, we peek in. The scene before us will be burned into my mind until the day I die. Our friend, on all fours with his underwear at his knees. His freaking mother behind him ramming a suppository up his ass. She is really going at it, in and out like she was churning butter or something. He is moaning, grunting, hands clenching bedsheets. His mother’s cooing voice “It’s ok honey, it’s ok (also burned into my mind thank you very much)

All we could do was retreat as quickly and quietly as possible. Normally we would have taunted him until our throats were sore but his mom was a very nice lady. She would have been horrified had she known we saw this. We get in my friend’s car, for some reason he floors it like we just robbed a bank. We pull around a corner and stop. Both of us fall out of the car laughing. The kind of laughing that ends up hurting your stomach and face. I am not ashamed to admit that I peed my pants that day.

The guy is well aware of this. Of course we told everyone when we got back. We teased him mercilessly a couple of day later. Someone even drew a stick figure mural to commemorate the event.”

Several questions here: Do grownups still get suppositories? Am I the only person who is lucky enough to have never gotten one of these in his life? And how sick would you have to be to let your mom still do this to you in college? I honestly think I would rather die than have my mom ram anything into my ass. 

He’s lucky you didn’t record it with your iPhones.


I’d like to remain anonymous please. Anyways, with gay marriage now the law of the land, is there anyone more excited than divorce, estate and probate lawyers? A whole new class of clients has opened up. And let’s be real, gays are going to get divorced as frequently as straight couples. Your thoughts?”

It’s a massive coup for divorce lawyers because you have to assume that the rate of gay divorce will end up being pretty similar to the rate of straight divorce. I would imagine that gay couples are less likely to have kids, which you would think would make the rate of divorce higher. Honestly, how many of you reading this right now would get divorced if you didn’t have kids?

Anyway, the gay divorce rate equaling straight people might take a while to happen because — just wait — in a few years everyone will be doing stories on how bad gay people feel to be getting divorced. You fight for generations for the right to gay marriage and then you get divorced three years after you get married? It’s like you’re a traitor to the struggle. 

So there will be tons of gay people who would ordinarily get divorced that won’t because they don’t want to get divorced this soon after gay marriage becomes legal. 

Regardless, if you’re a divorce lawyer in a big city this is your own personal stimulus plan. 

As for estate and probate lawyers, my guess is they’ve been working around the legal challenges of gay estate and probate issues for generations now. So I doubt it impacts them that much.  

“Since when do you let a female reader state in last week’s mailbag “I might have had group sex before” without extracting details? You’ve had plenty in recent episodes, but still … disappointing. And does she have any self-esteem issues? Just curious.”

Several of you emailed demanding to know why I didn’t quiz her more on the group sex admission. 

But you guys have to keep in mind, I’ve got an upstanding reputation to maintain here and…

Okay, you’re right, I blew it. 

“I love your stuff. You are uniquely entertaining. This is for the anonymous mailbag, because … Well, I think it will be obvious. I grew up in a pretty conservative southern home, and am a (SEC grad.) And I have a pretty visible career in my area.

I have started dating this girl who is really cool. I can actually see it becoming something pretty serious. We are both 27, and let’s be honest, we both have sexual pasts. But there is one thing I’m having a hard time getting past. She told me she had sex with a black guy. Is this something any other normal white guy would have a problem with? I’m not a racist in the least. I’ve just never encountered this situation before, so it’s all new to me. Thanks! Keep up the good work, or else fire that asshole Clay Travis.”

So if your girlfriend banged Barack Obama, you’d be upset with her because she slept with a black dude?

That’s insanity to me. I would brag to everyone I knew if my wife had banged Obama. 

I remember when I was in college one of the guys we knew had hooked up with Monica Lewinsky before she banged Bill Clinton. Monica Lewinsky wasn’t even attractive, but everyone thought it was the coolest thing ever that this random dude at George Washington had been hooking up with Lewinsky and then she went from him to Clinton. This was his go to line at any college party for two years — that he banged Monica Lewinsky and then she banged the president. It was gold. There were girls banging him because he banged Monica Lewinsky. 

If you’re over 22 — and probably much younger than that — you have to assume that your wife or girlfriend or your husband or boyfriend has had sex with someone before you. No one marries a virgin anymore in this era. (And if you did marry a virgin, chances are, she was doing anal and blowing dudes like crazy to preserve her technical virginity. So congrats on that. If you married a guy and he says he was a virgin, either you got married when you were 18 or he’s probably gay.)

So let’s unpack your fears here: Would you have an issue if she had banged an Asian or Hispanic dude too? Or just a black guy? You say yourself that you don’t have an issue that she’s had sex before, just that she slept with a black guy.

I don’t get this, why single out the black guy? 

Is this penis size fear?

Because the most recent penis study found no racial disparities in penis size between white and black men. (Luckily Greg Oden wasn’t a part of the study). Other than penis size fear, I honestly can’t come up with a theory to explain this other than racism.

I’m open to other suggestions, but, as an expert in racism, I think this is racist behavior on you and your penis’s part. 

By the way, easy racism test for a white guy: would you sleep with Beyonce or Halle Berry?

If you say no, I think you’re racist. I don’t need to know anything else about you. 

“A few weeks ago, myself, another guy and three other couples went on a cruise to the Bahamas. The trip was fantastic and resulted in an epic story.

There’s a program where you pay X amount of dollars at the beginning of the Cruise. By doing that, you’re allowed 15 drinks per day starting from 6 a.m. to 6 a.m. the next day. Once you reach the 15 limit, you’re officially cut off from any drinks until 6 a.m. the next day. The staff made that abundantly clear to us, which is fine. 15 drinks in that amount of time was a perfect amount for all of us.

Or so we thought.

The second night, I had gotten lucky with a girl and was leaving her cabin to head back to mine. I walk in to find my roommate passed out sitting on the toilet wearing nothing but a tank top.

I think nothing of it and pass out, only to wake up the next day and our room smells like roadkill. So I walk upstairs to get some fresh air and breakfast. I come back and look in the bathroom to find the source of the smell: Dude’s shorts have shit stains all over them. Everyone in our group is assuming this dude shit himself last night and we’re giving him the worst hell about it on the beach.

So the day passes by and we finally come back from the beach to the boat to get ready for dinner. Before dinner, we all decided we wanted something to drink. So we go to the bar upstairs and order something. However, the bartender tells the guy that his account has been frozen by the ship. We’re all looking around wondering what we he could’ve done wrong.

So he decides to go to guest services while the rest of us are getting drinks to figure out what’s wrong with his account. He comes back with the most outrageous story.

Apparently the night before he went to guest services because he was mad that he got cut off and was raising hell about it. Guest services claim that he pulled down his pants and dropped a deuce right in the middle of the lobby. Security was called and he was escorted back to our room. All of us are in shock and can’t help but burst out laughing. Now he can’t drink the rest of the cruise.

The final nail in the coffin though, is that as we’re waiting to leave the ship on the last day, his name is called over the intercom to come to guest services. He’s given a letter saying he’s been banned from any future cruises on this particular cruise line.

Now, my question to you, is what extremes do you have to go to get banned from ever setting foot on another cruise ship? Surely taking a shit in the middle of the lobby in front of the whole world to see has to be at the top.”

My first thought upon reading this — there has to be video, right?

My second thought, your friend is probably a psychopath. We don’t judge here in the anonymous mailbag, but I’m terrified to think about what kind of porn he watches. And he’s definitely thought about smothering kittens for fun. 

My third thought, just because you get cut off on the 15 drinks, couldn’t you buy an additional drink without using your all you can drink ticket? Granted, he might have been really drunk by that point, but it’s certainly possible, right?

Fourth thought, this reminds me of the guy who got banned for life from American Airlines for peeing in the seat back pocket on a flight to Vegas. I would give anything to be able to read each company’s list of what people have done to be banned for life. I would think the behavioral standards on a cruise ship would be incredibly lenient. I mean, we’re not talking about a high end group of people on most cruise ships, it’s like a Greyhound of the seas.   

“I spent the weekend in Austin playing golf with one of my best friends. When I got home Monday, I asked my wife what she wanted to do the next day.

She said, “I kind of just want to eat a steak and have some sex.” 

Did I marry a unicorn?” 


Or she just went off birth control without telling you and is trying to get pregnant. 

Send your anonymous mailbag questions to Anonymity guaranteed. 

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.


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