Anonymous Mailbag

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It’s Tuesday, which means it’s time for the anonymous mailbag.

We begin the anonymous mailbag with an email about this insanely absurd backlash against John McEnroe for saying that Serena would be around the 700th best men’s player in the world. A question that he was specifically asked. Go listen to my entire analysis of this story on Outkick the Coverage this morning.

This email summed up many of my thoughts as well.

“This whole John McEnroe vs Serena comments backlash is ridiculous.

Sports media makes their living comparing teams and individual players constantly. Why is it OK to debate whether Alabama could beat the Cleveland Browns? Whether the Warriors could beat great NBA teams of the past? If Tiger Woods would be better than Jack Nicklaus if they played against each other in their primes? Isn’t that disrespectful to diminish the accomplishments of a great team by saying they couldn’t beat other great teams?

Yet that same line of comparison is all of a sudden discriminatory and unfair when the discussion involves different genders? All the talk about how everyone should be treated equal yet when comparisons are made between genders that is crossing the line?

No one knows where Serena would be ranked if she played on the Men’s Tour. Would it be higher than 700? Possibly but no one with any semblance of a brain thinks she would be able to play with the top players. Would everyone that is so offended now feel better if McEnroe had said Serena would be ranked 350 instead of 700?

John McEnroe has been around the game of tennis for over 50 years. He has seen more tennis matches, been around more players and knows more about the game then 99.9% of people in the world yet isn’t allowed to have an opinion on this? Meanwhile those who are criticizing him have nowhere near the experience as he does yet consider themselves experts?

What we do know is this — Serena and Venus both played Karsten Braasch, a male players ranked 203 in the world who rarely even played the tour anymore by this time. He played golf before the matches, smoked and drank during the changeovers yet lost only 3 games total in the 2 sets against the Williams sisters. After that you never heard anymore stories about the Williams sisters playing against men as they knew it was a futile task.

John McEnroe offered for years to play Serena or Venus in a match but they never took him up on the offer. Of course not as they knew what the result would be even against an over the hill former top male player.”

Here’s Serena on David Letterman saying she would lose 6-0, 6-0 if she played one of the top men. And also her saying that the reason she didn’t play men was because she didn’t want to be embarrassed.

Pretty sexist of Serena, tbh.

Okay, on to the typical anonymous mailbag question. And it’s incredible.

“Crazy story from this past weekend. A couple of buddies and myself are at a lakehouse in a pretty tiny town on Friday night and after much drinking we decide to go to the local bar (yes there is only one in the town).

We get there and one of our buddies immediately starts flirting and dancing with these two approximately 40 year old chicks. These girls hang out with us and take shots at the bar with us pretty much the whole night. At this point it’s like 2 am and we all head back to the house.

Well about 30 minutes after we all get there and obviously still drinking etc. we realize our buddy who was leading the efforts with these two chicks shows back up at the house with the 40 year olds. Several of our friends have passed out by this point but for whatever reason these chicks continue to hang out and party with us and at some point start saying that they have fake boobs. Obviously we ask them to show us – and they pretty much immediately take off their shirts and we are just like yep those are fake.

The next morning we ask our buddy who lead the charge with these girls if he ended up getting any action…this is where it gets strange. He says at about 4 am he is walking them out to their car and is giving them hell for not having hooked up with him after a night of dancing, flirting and talking dirty not to mention the taking off the shirts thing. So he asks if he can get a blowjob? The blonde, who at this point is in the drivers seat of her car, says no she doesn’t think so. He says not even a handjob? Again she says no but follows it up with “How about this? I will take my shirt off again and play with my tits and you can jack off.” He says “Okay, but where am i supposed to finish?” That’s when 40 year old number 2 who is in the passenger seat chimes in and says “you can just finish on my leg.”

So he does it. He finishes on girl number 2’s leg while she covers her face and girl number 1 is in the drivers seat shirtless not saying anything. It all ends by him saying “Well that was weird” and walking off.

My question…of the three people involved whose behavior is most psychotic?”

The only thing that explains this decision is that the two women are married and probably strippers.

Otherwise this makes no sense. What normal girl even thinks of this option? “No, I won’t hook up with you, but you can jerk off on my friend while I play with my boobs?” Just not a normal, average woman thought process at all here.

The image I can’t get over, by the way, is girl number two covering her eyes in the passenger seat. (Was it because she couldn’t bear to watch or so she didn’t want to get hit in the face? Both?)

Here’s my psychotic rankings for this trio:

1. The girl getting jerked off on.

This is undoubtedly the weirdest move of all. At least you can argue that jerking off and playing with your boobs are both somewhat normal sexual acts — having someone jerk off onto your leg while you sit in the passenger seat of the car with your eyes covered up is such an incredible sexual act that almost no one can relate to it.

Imagine if you were all telling sex stories one night at the bar and this girl said, “This reminds me of the night my best friend was playing with her boobs in the driver’s seat while I sat in the passenger seat with my eyes covered while a guy we met at the bar jerked off on my leg.”

Total record scratch moment, right?

I mean, seriously, there are tons of women reading this right now. (I swear). And most of them don’t want to get finished on by their boyfriends and husbands actually during sex. And this chick is totally fine with a stranger finishing on her leg for free?

Major psycho alert.

2. The guy jerking off.

Okay, so you ask for sex, get shot down, then ask for a blow job, get shot down, then ask for a hand job, get shot down and eventually you negotiate down to jerking off while a girl plays with her boobs. Is that ideal? Of course not. But is it better than jerking off looking at your iPhone? For sure.

I love the persistence here. Gotta be honest with you guys. Back in my single days no way I’m going all the way down the sexual ladder here. Once the sex and blow job got rejected I’m calling it a night. This guy is like the Henry Clay of sex, just working until he gets a great compromise.

Do you think back in the day Henry Clay could get chicks to do all sorts of freaky stuff? The ultimate negotiator. He starts with something he knows is going to get rejected and before long he’s got Betsy Ross naked in a tub with a flag pole.

I’m just saying, guy seems like he would have been good at getting bloomers dropping after a few drinks.

Anyway, this guy would be be number three on this list except for the fact that he asks where he’s supposed to finish? Seriously, this is a real question you ask? You’re jerking off outside a passenger side door of a lakehouse in the middle of nowhere while a 40 year old woman plays with her boobs in the driver’s seat and you’re worried about where you finish?

Just go in the dirt, Onan.

3. The girl playing with her boobs.

Total stripper move here. She’s thinking: “I want to be rid of this guy. What do I do to get rid of him? I’ll play with my boobs.”

I don’t even think this is even very deviant behavior in the grand scheme of things.

That’s it, this is in the indisputable sexual perversion power rankings. Anyone who disagrees with this order is loopy.

By the way, this story is hysterical to read, but can you imagine if some drunk dude walked on the front porch and witnessed this all happening? Was the car on? It’s even funnier to me if the car was on and the car lights were on too.

Think about this scene then.

A girl in the driver’s seat is rubbing her boobs all around, a girl in the passenger seat has her eyes covered with your forearm and your buddy is just jerking as hard as he can, pants down around his ankles, in the middle of the night outside a lakehouse in the middle of nowhere.

Tell me if a book or movie started this way you’d stop reading or turn it off. No way.

Just a mesmerizing story.

You know both these women got home and their husbands were like, “What’d y’all do tonight?”

And both women were like, “Just had a few drinks, nothing special.”

This story is what the anonymous mailbag was made for.

“I got caught taking a shit in the bushes of my apartment complex. About a week ago, I was deathly ill. The type of sick where all you can do is pray for the sweet reprieve of death. I finally work up the courage to take my lab puppy out to take his own dump, and while I’m several buildings down I get the familiar feeling of gastrointestinal distress.

Thankfully, this is at night so I’m not worried about being seen clinching my ass cheeks together and doing the shit shuffle as quickly as I can back to my building. As I near my building I realize I’m on the verge of a major blowout and no amount of ass retraction is going to prevent this. With no time to spare, and in one swift motion, I dive behind a tiny bush surrounding an AC unit, thrown my gym shorts and boxers around my ankles, and let the magic happen.

My mistake becomes apparent when I realize there is a car coming, and it’s heading straight to the empty parking spot in front of the bush. I try to crouch and conceal myself as much as possible, but in my condition, while trying to corral a puppy, my effort is futile. There I am staring straight into the headlights of one of my neighbors, taking a greasy shit in the bushes of a swanky apartment complex. Realizing there is nothing I can do, I decide to own the situation and wave at whoever is blinding me with their headlights. The car then backs out, and drives off. It’s been a week, and I’ve not been confronted by any of my neighbors.”

The only thing that could make this story better is if the person pulling into your apartment complex was the girl who just got jerked off on.

She pulls into her apartment complex ready to take a shower and pretend that her night didn’t just end as it did and she sees you shitting behind a tiny bush, with a Lab puppy on a leash beside you, and just gives up on life. Turns around and just starts driving, no idea where she’s headed, just going somewhere, anywhere but where she is.

I’d love if you got called in by the apartment complex manager and you had to explain yourself. Could you get evicted here if you just said, “Look, I was going to shit myself and I did what I had to do.”

I don’t think you could.

“I’m in a relatively new relationship with a great guy. We make each other happy, we have fun together, everything is great.

The other day, after drinking all afternoon at the pool at my place, we stopped for wings on the way back to his place. I vividly remember watching him wash his hands after eating ATOMIC wings, and about an hour later we started fooling around.

Well, let’s just say he didn’t wash his hands well enough, and my nether regions were set on fire. I was a good sport about it. Granted, the pain wasn’t that awful, and we laughed about it for at least 45 minutes. We still laugh about it today, and honestly I’m pretty sure I gave him a blow job that night.

Here’s where I need your help…I need some kind of revenge here. I’ve been plotting, and he actually suggested that I ask you, since we’re both fans. It’s worth noting that I thoroughly enjoy having sex with this guy (and I’m not an asshole) therefore doing anything to his dick is honestly a punishment for me too. So whatcha got?”

Tell him you’ll be in a threesome with a hot girlfriend of yours if he lets you bang him in the ass while wearing a dildo.

Then, if he agrees, strap on and just before entry say, “You know what? I changed my mind. I think you’re gay for letting me do this. I can’t stay in this relationship.”

And then leave the bedroom.

Sit outside on the couch.

If you can keep from laughing, just wait until he comes sprinting out of the bedroom trying to defend himself. See how long you can argue that you think he’s gay. And listen to his defense that he isn’t gay.

This may not work since he reads the mailbag too, but you want to talk about a way to take control of a relationship? Bang, power moves only, ladies. He’s never disagreeing about anything with you again.

Secondary option, tell him you saw that he’d been looking at porn on his iPhone and you were so concerned about the future of the relationship that you scheduled couples counseling. And also emailed his mom about the kind of porn he’d been looking at and wanted to know her opinion of what to do about his addiction.

Either of these is a gold move, I think.

“Clay, I’m an early 30’s white male (aka the devil) and recently met this knockout of a woman. 10/10 body, great career, overall just phenomenal. However, about a week into us getting to know one another, she asks me my political viewpoints. She quickly assumes that I’m a massive Trump supporter because I’m a white Christian living in the Midwest. While I do support some policies, I don’t agree with everything, but that’s another story.

She goes on to tell me how she’s super liberal as of the last couple years and then starts getting emotional when I told her I would never support HRC. Going on and on about how I don’t care about women, minorities, homosexuals, etc. Come to find out that her ex was super far left and they coincidentally started dating over the last couple of years. Is there anything that the far left doesn’t ruin? And I’m pretty sure I need to just walk away from this now, but I feel like she’s been brainwashed and just doesn’t know any better. What say you, wise one?”

If she’s actually a ten, I’d stick around.

It’s a rare couple that doesn’t end up rubbing off on each other at least somewhat politically. Because even if you disagree fundamentally with someone politically, it’s hard to consider them evil if you’re married to the other side. Honestly, we need more mixed marriages in this country, not less.

Before the last election my mother-in-law came up to me and asked if she could talk to me privately. She’s never asked to have a private talk with me in 13 years of my marriage. So I tell my wife about it and I’m thinking, “Oh my God, what’s this conversation going to be about?” I’m terrified that she has terminal cancer or got accidentally emailed my PornHub search history.

So we go upstairs to talk and she says she’s been watching my Outkick the Shows and then she just drops an absolute bombshell, “I think you’re being too kind to Hillary Clinton. She’s an awful human being.”

This just floors me. Turns out she wants to talk about who I’m going to vote for and I said, “You don’t need to worry about me. I’m voting for Gary Johnson. You need to talk to your daughter. She’s a big Hillary supporter.”

So I go back downstairs and my wife is all open-eyed, like what did you guys talk about?!

And I say, “I told your mom you’re voting for Hillary. She’s not happy and wants to talk with you.”

So I guess what I’m getting at here is this, any time someone questions your decision making once you’re married just point that while your decision making may not be perfect, your spouse’s is worse. Bang, problems solved.

If this girl has only become a diehard liberal in the past couple of years that suggests her political philosophy is still pretty fluid. You can probably coax her back from far left liberalism to moderation.

You can work on a lot in a relationship, but you know what you can’t do? Turn a soft six into a hard ten.

Good luck.

“I pray that the same 11 women every night do not ever talk to me, because I am a weak man. I love my wife more than anything in this world,and I don’t want to mess my marriage up. I just want to know if that is noble of me or pathetic. Thoughts?”

It depends on if you know the women or not.

If you’re praying that Tanya, the divorced, 37 year old legal secretary for the partner in your law firm doesn’t talk to you, your marriage is fucked. Because eventually one of those 11 women may want to bang you and you’re basically acknowledging you have no hope of resisting.

But if you’re praying that Charlotte McKinney, the woman in the picture above, doesn’t suddenly show up and ask to blow you in the car outside while your daughter’s second grade talent show is going on, I think that’s an okay prayer.

Just remember to be a gentleman and finish on her leg.

Send your anonymous mailbag questions to, anonymity guaranteed.

Written by Clay Travis

Clay Travis is the founder of the fastest growing national multimedia platform, OutKick, that produces and distributes engaging content across sports and pop culture to millions of fans across the country. OutKick was created by Travis in 2011 and sold to the Fox Corporation in 2021.

One of the most electrifying and outspoken personalities in the industry, Travis hosts OutKick The Show where he provides his unfiltered opinion on the most compelling headlines throughout sports, culture, and politics. He also makes regular appearances on FOX News Media as a contributor providing analysis on a variety of subjects ranging from sports news to the cultural landscape. Throughout the college football season, Travis is on Big Noon Kickoff for Fox Sports breaking down the game and the latest storylines.

Additionally, Travis serves as a co-host of The Clay Travis and Buck Sexton Show, a three-hour conservative radio talk program syndicated across Premiere Networks radio stations nationwide.

Previously, he launched OutKick The Coverage on Fox Sports Radio that included interviews and listener interactions and was on Fox Sports Bet for four years. Additionally, Travis started an iHeartRadio Original Podcast called Wins & Losses that featured in-depth conversations with the biggest names in sports.

Travis is a graduate of George Washington University as well as Vanderbilt Law School. Based in Nashville, he is the author of Dixieland Delight, On Rocky Top, and Republicans Buy Sneakers Too.