Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always, you can email me at, anonymity assured. 

With that in mind, here we go:

“We all witnessed the Dobbsnail Boot on Saturday. I have literally never been on the emotional rollercoaster that that game sent me on! It was an amazing experience. My buddies and I were going absolutely crazy after the game. As the true Vol fans that we are, we kept that positive energy going as we headed out on the town to keep stomping peoples noses with our own Dobbsnail Boots. (Sidenote: if I’m a bar owner in Knoxville, I immediately create a “Dobbsnail Boot Shot” and become the most profitable bar in the state of Tennessee. Easy money.) That night was a spiritual experience. Truly. We did it big and all made our way back to the house somehow.

Then my buddy’s girlfriend started talking to him. They are both in their late 20’s and have been off and on for almost 3 years and haven’t spent a full calendar year dating the entire time. They have been a train wreck from the beginning, yet somehow keep coming back for each other. We have all told him on multiple occasions to move on, but he won’t. So back to Saturday night, we are all still high on the Vols win and more than slightly inebriated, and she starts asking him when they are going to get married. He (drunkenly) responds as we all wanted to, “What?! We just beat UGA on a hail marry pass and you want to talk about marriage?!”

Needless to say, she was crushed, and they broke up again. All signs indicate that this is a done deal. He really seems over her now.

My question for you is why did she feel like the night after the most iconic play in UT football history would be a perfect time to talk about marriage?”

Because she was concerned that her boyfriend cared more about Tennessee football than he did about her and she wanted him to convince her otherwise.

Unfortunately for her, it was a really, really big play… and he does care more about Tennessee football than he does her.

Both of them will be better off.

Chalk it up as another big win for Jauan Jennings.

“Have you watched Westworld on HBO yet? If not, you have to. I find myself wondering if we’ll, at some point, become so technologically advanced, that it becomes the norm for every American home to have a couple of sex robots stashed away in a robot closet to use as we see fit? Also, does this satisfy the need to stray from a committed relationship? Does sex with a robot count as cheating? Do women and men get jealous of robots? And who has to clean the sex robots? Is that the worst job ever?”

I don’t know if we’ll have sex robots any time soon — because the technology to make a robot seem as real as a human isn’t there yet — but I definitely think virtual reality sex will become pretty common in the next 20 years. 

That’s the next iteration of sex and technology, right?

Basically any time a new technology happens we find out a way to wed sex to it. The Internet gets invented and before long people are having cybersex. Texting leads to sexting. Webcams leads to sexcams. The moment a new technology arrives we find a way to incorporate sex into it because there’s money to be made there. 

Virtual reality is going to be great for two things: a. sports and b. sex. And, like most things, the majority of the money that is made off of virtual reality will end up coming from sex. 

“A couple of months ago, I’m talking with my buddy about sex with our wives. A little background first…We are both mid 30’s. Both married around the 10 year mark, both with two kids. Our wives are friends as well. So obviously, the vast majority of “sex with our wives” stories, come from before they were our wives.

He’s excited and can’t wait to tell me about the night before. What he describes next, can best be described as, random, wild ass, couch sex. As a married man, you know that random, wild ass, couch sex just doesn’t happen. At least not without copious amounts of alcohol, but even then, pretty damn rare. He is riding the euphoric high of unprovoked sex. Feeling sorry for myself, I went home, reminiscing about the days of yore. The kids are in bed, long asleep. I’m on the couch watching tv, wife in the bedroom watching tv. Then it happens. She appears from the hallway with a look of sheer determination. No words are spoken. I know that it’s about to go down. The first thought that crosses my mind, “don’t fuck this up”. I did not. I’m talking, pre-game warm up, multiple positions, and photo finish. I’m in disbelief for at least an hour afterwards. What just happened? We just banged, on the couch, while the kids were home, and it was her idea! My first thought: the wives planned this, right? I mean, there is no way that this just happened to both of us. I keep this all to myself.

Fast forward to this week. I’m working from home. Wife is at work. She arrives home around mid day. Says she has a break between appointments. I was headed out. She tells me to wait. My heart starts racing. “Don’t fuck this up.” What I got was sex, IN THE DAYLIGHT, and confirmation that her stop at home was solely to play hide the wiener. This morning, my buddy sent me a text. He got similar treatment yesterday. Now, it’s confirmed. The wives have some sort of friendly competition going on.

Now, I’m a smart dude. I want to share my experiences with my friend, but I’m worried that he will fuck it up. There’s no way that he can keep this to himself. He will certainly bring this up with his wife, and break the first rule of random sex with your wife, “Never talk about random sex with your wife.” I’m nervous as I type this.

No way I bring this up with her, right? Do I just play dumb , sit back, and patiently wait for the next episode?”

This is such a perfect married man sentence to begin this email: “So obviously, the vast majority of “sex with our wives” stories, come from before they were our wives.”

Also, what are the odds that both your wives read the mailbag and despite the fact that you were worried about your buddy fucking it up, you just fucked it up by emailing me?

In the meantime, you guys need to make sure that this wife competition goes to ten overtimes.

But if you want to get really aggressive with the competition you start leaking fake sex acts to each other in the hope that the other wife hears about it and tries to compete. “Guess what John said Jennifer did last night? Threesome with the hot kindergarten teacher at the elementary school. I swear to God, he says they did it. I couldn’t believe it either. She must be really wild!”

Good luck. 

“I had sex with my fiance and actively thought about another woman while we had sex.

This isn’t some Scarlett Johansson/Blake Lively bullshit. I was thinking about a woman I know who I have never had sex with. What the hell is wrong with me?”


“This could be the weirdest story of a trip to the tailors you have ever heard. I went to the alterations shop to pick up my amazing Outkick pants today. My team has homecoming soon and I am pretty excited about these fresh, new, amazing pants. The shop owner brought them out and I headed to the dressing room to try them on. There were two dressing room doors, both closed, so I opened the UNLOCKED door on the left and quickly discovered the room was occupied.

The woman in there was naked as the day she was born, except the t-shirt she was currently pulling off over her head. No shoes, socks, or underwear to speak of at all. This was a pleasant surprise for one of us, but embarrassing for both. I quickly shut the door, apologized a dozen times, and slipped into the other dressing room. I stood there alone in silence wondering what to do. Should I apologize once again? Should I come out with some witty joke? To be honest, I was trying to think of what Clay Travis would do in this situation. Before I could figure it out, she concluded her business at the shop and left the building.

So I tried on the perfectly hemmed pants and did a deep knee bend to test their flexibility. “POP!” I busted the seam that runs up the ass crack. Luckily I was 10 feet away from the one person uniquely equipped to handle this emergency on a Friday afternoon. I complimented his work on the hemming, then asked him to fix my busted ass quickly. He did, I paid for his services, and left.

In the parking lot, I had the most awkward situation of the whole event. The naked lady from before was sitting in the front parking spot pretending to check her phone, watching for the perpetrator. I immediately recognized her, but she did not recognize me. A few seconds after I left the shop, another dude walked out right behind me. As I was driving away I saw her get out of her car to confront him about the incident. Poor guy never saw it coming!”

What if you’ve got this all wrong and she actually wanted to bang that guy? And she would have banged you, but she got confused as to who had seen her naked?

Trust me, this kind of thing happens all the time when hot women are showing houses on Pornhub.

In all seriousness, I’m baffled by this situation, why would she be completely naked in the dressing room? I can see being in her underwear or even being topless, but why doesn’t she have panties on? Is it possible she and her boyfriend do this for fun? Was she trying to surprise him and instead you showed up?

I feel like we need to hear her side of the story here. 

Also, the more times you compliment Outkick’s pants the better your chances of making the anonymous mailbag. You may be young, but that was a veteran move by you.

Our pants are almost gone.

“I’m hoping you can settle something for me. My group of girlfriends and I have had the same debate going on for a while now, and we seem to be split down the middle. We keep arguing back and forth about what is considered a blowjob. Myself and a few friends think a blowjob is only a blowjob when the guy finishes, but the other half seem to think it’s a blowjob anytime there’s a dick in the mouth. I have no idea how you can count it as a blowjob if the guy isn’t finishing but somehow more than one of my friends agrees with this insane idea. Please settle this for me!”

Okay, let’s take this out of the blow job arena and put it in the context of regular sex. Did you have sex if copulation occurs, but the guy doesn’t finish?

The answer is, yes, right?

Okay, what about a guy going down on a girl? Does it count as a guy going down on a girl even if the girl doesn’t have an orgasm?

The answer is indisputably yes, right?

So it counts as a blow job even if he doesn’t finish. (Now, we can hem and haw here on details — for instance does one lollipop suck count, I would argue no, but if there is at least one minute involved, it’s definitely a blow job.)

“Clay, I am a senior at a private high school and we have a sister school that is known for being extremely liberal and over the top PC. During the Trump-Clinton debate, I posted a snapchat story of a speech bubble next to Hillary’s face and it read, “I can’t even satisfy my own husband.” It was a common joke that is tossed around on social media quite often, so I thought nothing of it. I received a few texts and snapchats back saying how funny my snapchat story was and all was well.

30 minutes later, I look at my snapchat story, and it had 10 screenshots, all from girls in my grade at our sister school. I began to get texts and calls from all sorts of people calling me a sexist and a “hater of women.”

I took it down due to the bad publicity, and took to twitter to say, “Geez, y’all can’t take a joke.” I still do not think is was an over the top joke. The next day at school, everyone is on their phones viewing a handwritten letter addressed to me from one of the PC girls in my grade. The letter accused me of being a sexist bigot who hates women. The conclusion of the letter said, “Good luck finding a wife that will satisfy you.”

Everyone at my school is defending me, agreeing it was a simple joke that should not have offended anyone. Everyone at my sister school thinks I am the most sexist guy ever. So Clay, I am a sexist bigot? Was my joke too far? Or did the PC feminists overreact a little?”

Jesus, this is absurd.

I don’t know how you can even go to high school or college today and not be a total pussy. 

But let’s dive in here to your question. 

First, no one could satisfy Bill Clinton. The dude is a certifiable poonhound. He could have been married to a porn star with an insatiable sexual appetite and he still wouldn’t have been satisfied with her.

Because what he’s after isn’t sex, it’s sex with new women.

Most women aren’t wired this way so they always react with surprise when they see a man cheat, especially if his partner is good looking, and say, “Why would he cheat on her, she’s beautiful!”

Men, on the other hand, all understand why this happens. Now a man may not cheat on his significant other, but he totally understands why another man would cheat on his wife. It’s because that’s the way men are wired biologically. You may not do it yourself, but you understand the thought process. (Yes, even your husband or boyfriend who is claiming right now that he has no idea how a guy could do this. He’s lying to you.)

Now, as for whether what you said was offensive, of course not.

This is fairly tame for presidential humor, especially if you’re supporting the other side. 

I’d like to say that a high school girl handwriting a letter complaining about your Snapchat joke during the presidential debate and insulting your ability to find a wife — IN A DECADE OR MORE — is too absurd to believe actually happened, but welcome to the modern educational environment.

Your joke was perfectly fine and, to be honest, not even that original. Like you said, it’s a common joke theme.

Everyone who was offended by it is a total pussy.

And what’s our number one rule at Outkick?

Don’t be a pussy.


So don’t worry about it.

Also, if you want to be really diabolical, find out who this girl’s biggest enemy is and invite her to prom this year. You’ll set off a cavalcade of “Mean Girls” drama at the school that will last the rest of the year.

You’re welcome.

I’m off to Dallas; we’ll have Vince Young and Brian Bosworth on the Outkick show tomorrow. 

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.