Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

As always, send your questions to, anonymity guaranteed.

And when you head down to the beaches at 30A, why stay in a tiny condo when you can stay in a mansion on the beach? Check out these houses that my friends at 30A cottages have available for rent. Use the code Outkick and save 5% in February, March and April.  

Here we go:

“Question for you. Was recently talking to this girl who was against having sex before she got married. However, she would do LITERALLY anything else. Including, to my surprise, anal sex.

How many girls out there are morally okay having anal sex with guys but won’t have regular sex? Does this make any sense? I just really wanted to have regular sex.”

Extremely religious people believe many dumb things, but this might be the dumbest.

Play this logic out with me. So let’s say you arrive at the pearly gates and God is flipping through your roster of sins to see whether you get to go to heaven. Do you really think God is going to be like, “Kaitlyn, okay, you didn’t have premarital sex so that’s 50 Jesus bonus points, but,” flipping through his chart, “I do see that you had anal sex with 32 guys and that you blew 74 guys. But well done for not having vaginal sex, you kept that chastity belt on! 50 more Jesus points!”

This is just insanely stupid to me.

Futhermore, doesn’t it make God seem like a huge pervert.

If anyone else but God kept track of your sexual shenanigans while secretly spying on you all the time, he’d be in jail and have to register as a sex offender. But God does it and it’s perfectly normal?

I’m just not buying it.

Also, can you imagine how long the line is at the pearly gates if every masturbation is recorded? God’s like: “Clay Travis, okay, wow, you have really jerked off a ton of times. You should be in the jerk off hall of fame with these numbers. You’re the Babe Ruth of jerk offs.” 

And while we’re on the topic, isn’t getting into heaven basically pass/fail? Don’t you want to be closer to the fail line than to passing with ease? If we’re all ending up the same place for all eternity, it seems like you should have some fun/sin as much as you can and still get your passing grade. I mean, don’t you think the dude who only had sex with his wife has some regrets if he died and was in line right behind Wilt Chamberlain?

Wilt’s looking over his shoulder, like, “My bad, dude, it’s going to be a little wait.”

God’s up there reading off this long laundry list of girls Chamberlain banged and the guy behind him is getting all mad because it’s like being in line at a grocery store when you only have one thing and the guy in front of you has two cart fulls of objects. 

I hate standing in line for anything, even Heaven. I want a Heaven fastpass. Surely they have that by now.  

“I want to know if it is socially acceptable to watch the new movie 50 Shades Darker (alone) as a single 26 year old male?”

This is 100% socially unacceptable.  

But you’re 26, hop on Tinder and take a date to this movie. If she won’t bang you after watching 50 Shades Darker, then you have no hope for sex. 

By the way, does this movie, which opens on Valentine’s Day weekend, have the highest percentage of couples that will have sex after a movie of all time? What’s number two and aired in theaters? Basic Instinct? 9.5 Weeks? Any other nominees? 50 Shades Darker is a movie entirely about freaky sex. The only reason to go to this movie is so you know your wife or girlfriend will do freaky stuff after the movie, right? 

Basically if you go to this movie with a girl and she doesn’t have sex with you after it’s over, you have really fucked something up. 

“I need a ruling from the King Solomon of college football and real-world relationships.

I’m a divorced dad in my early 30s, and my girlfriend is in her early 20s. On the weekends that I’m not parenting, we basically just hang out in my room, watch movies, and have sex. A lot. Plus we’ve both been tested and she’s got birth control handled, so it’s all bareback! Nothing is out of bounds or off limits, and the only thing that caps our “festivities” is the number of times I can perform. All day Saturday. All day Sunday.

Sounds great right? Well, it is. But there is one unintended result: I have missed the 2016 football season. It’s like 80% fewer games than I saw last year. I sometimes caught MNF, and maybe an early Saturday game (I’m west coast), and I made plans for the occasional “big game”, but by-and-large I missed football this year.

The worst part? I don’t think I care! It’s fucking awesome! Sex is just this assumed thing we do every day we’re together. We’ve been dating a year now, and sex has replaced football watching as my primary weekend activity.

The craziest part? She knows it and will occasionally tease me about it…at opportune times. She’ll ask if I’d rather be watching football while giving me a BJ. She has oft noted we can go watch football, but that she’ll have to get dressed for that (she’s ALWAYS naked). She’s reminded me that I could be watching the game with my friends, as I was about to enter her.

Am I insane for not caring? Or is it completely rational to skip 95% of games for a no limit bareback sex buffet with a super fit smokeshow in her early 20s?”

Brace yourselves: I would rather watch college football than have unlimited sex on a Saturday. Even worse, I think I’d rather watch the Tennessee Titans play than have unlimited sex on a Sunday too. 

My rationale here is pretty simple, there are only about 16 weekends a year when I’ve got football to watch. That leaves 36 other weekends to have unlimited sex. 

Also, what does unlimited sex mean? I’m 37, that’s like four times having sex. That’s going to take me about 14 minutes total. What the hell else am I doing with the rest of the day? 

I’d rather watch football. 

“Clay, I’m writing you because I have nowhere else to turn and if you can’t trust the advice of a gay radical Muslim transgender person who can you trust?

My dilemma is me and my friends have always been apart of the “party crowd” but now we’re all a little bit older, though still in our prime (all in our 20’s) but my problem is most of us now have a child/children, I don’t, but one person in particular just had a boy about a year ago and now brings the baby to all “social gatherings.”

The problem is, is his wife just got a new job and she’s working longer and more hours and unable to now watch the baby when he comes out to drink with us and have a good time. Well this doesn’t put a stop to his partying itch that he needs to scratch as he’s always up for a good time but now as of recent, the baby’s always there and he, like most babies, cry ALOT.

My question is how would you go about approaching the situation? Do you not say anything and spend your weekends wasted, listening to a screaming baby that’s teething? I obviously can’t tell him “Hey man could you grab me a beer and by the way your kid is driving me crazy.” He’s my best friend so I really can’t just stop hanging out with him but, I also can’t continue with what’s become the norm as of late. I don’t really know what the others think about it as I’ve never really spoken about it out of fear it gets back to him. So Clay, I come to you as my last hope, what should I do?”

The solution here is simple: he has to get a babysitter. 

Babysitters aren’t that expensive. If he puts the baby to bed then all the babysitter has to do is sit there and make sure the house doesn’t burn down. Seriously, it’s the biggest racket out there. I’ve paid thousands of dollars for babysitters to come over to my house and watch movies for several hours while the kids are sleeping. Plus, it’s a cash business so the babysitter gets to keep your entire cash paycheck.

And you have to book a damn babysitter like a month in advance. It’s such a racket.  

Babysitters and strippers are the only people who I’ve needed cash for in the past ten years. And at least the stripper is doing something. The babysitter is just sitting there.

I know what you’re all thinking, and it’s pretty much genius, why not combine the two — babysitter strippers!   

It’s not just for pornhub!

(Seriously the number of featured videos with babysitters, step moms, step sisters and assorted other family related connections makes me nervous about our country’s masturbatory future. You millennials are all claiming to be social justice warriors and you’re jerking off like crazy to stepsister and stepmom porn. I see through your charade of altruism, assholes.)

Having said that, you want a billion dollar business? Uber for babysitters. You background check every client and then you pull up the app and you can see how far away all the babysitters are when you need one. Then you can watch them drive towards your house in their cars and get a babysitter on demand. Related, is there anything worse than getting a dumb Uber driver who can’t find his way to your pick-up location? You’re holding up the app watching them and they take a wrong turn and the wait time goes from three minutes to eight minutes? “Fuck you! It’s freezing out here. And you can’t follow the directions on your phone?” 

I have to lead the nation in Uber drivers who go the wrong way. It’s like watching dumb people play Pacman. 

Also, this past weekend in Houston I got an Uber driver who was deaf. It popped up on the screen that I couldn’t call them. I showed my wife and asked her if I should screenshot and it and Tweet it out, but she said that would be rude to a deaf person. What? He’s deaf, it’s not like I outed him for herpes.

Of course this deaf dude went the wrong way and I’m just sitting there with my phone thinking, “What do I do now?” I can’t cancel on a deaf Uber driver because my rating would take a hit.

So he eventually shows and talks perfectly normal.

I think he’s faking being deaf so he gets less complaints.  

“I was walking my dog by a playground across the street from my house. I see a boy (about 6 years old) put a banana in his pocket. We are both facing each other and his dad had to have seen me see him perform this act. As I walk by I simply say “Looks like you have a banana in your pocket.” I did not ask if he had a banana in his pocket and I definitely did not drop the “excited to see me” punchline.

The dad proceeds to scream and ultimately threaten me, it was the level of anger where I knew whatever I would say would just make it worse…I could also tell my dog was getting very defensive, which I have never seen him act like so I just got out of the situation as fast as possible.

I’ve lost sleep over the fear that what I said was really fucked up and creepy. Are my fears substantiated or was this dude just a huge douche?”

This is where being a single dude works against you.

If you change the sexes here and you’re a hot girl out walking your dog and you say the exact same thing the dad actually finishes the joke for you, “No, he’s just excited to see you,” and you probably make his day. I guarantee you that if a hot chick said this to any of my guy friends while they were out with their kid I would hear about it. And then I would also hear about how much this hot chick wanted to bang my friend.

100% without a doubt. And all your dad friends would share this story too. Just more evidence of #hotgirlprivilege   

But what you did is, I’m gonna be honest, a little creepy. Even if your intent was to be perfectly normal, it was pretty socially awkward. Fair or not, single men are the biggest threats to young children. Which is why I would never allow a single guy to babysit my kids. Just won’t do it. I’m sexist against men in this way.   

This dad saw you as a threat and while he may have overreacted I can’t say that based on statistical data he was completely in the wrong. 

If this had been me I wouldn’t have made a scene, but I probably would have laughed awkwardly and taken my kid’s hand. 

“My wife and I are separated and going through a divorce. We are getting along much better, worked out property and money issues, and the visitation schedule has been going great with our little one. Your storybook ending divorce I’d say. 

I told you all that to get to my question. My ex’s father has always been an important person in her life. He’s a great guy. Hell, I like him. But he kind of sucks at doing dad stuff. She was fine with most of it except for her birthday. Every year since we had been together, I’ve had to sneak off at some point during the day to call and remind him it’s her birthday.  

I would go make the call. He’d call her cell a few minutes later wishing her a happy birthday. This allowed her to enjoy the occasion, and I didn’t have to hear her spiral into depression while recounting every birthday he had forgotten over the years. 

She has no idea I’ve been doing this the last several years. I still get along with everybody wonderfully. Her dad and I even have a few hunting/fishing excursions planned for later in the year. Her first birthday since we’ve been divorced/separated is coming up soon. Should I give my ex father in law a few more birthday reminders? Or does she lose this illusion of her father in the divorce? Thanks and “your gay.””

I’d keep calling my father-in-law on her birthday to remind him to call. 

You share a kid with this woman and her happiness, or lack thereof, with her dad could end up impacting her relationship with your son as well as your son’s relationship with his grandpa. 

Just because you’re divorced doesn’t mean you have to become an asshole. And if you know it would upset your wife if you stop doing this and it doesn’t take you much time and you stop doing it solely because you got divorced, I think that’s an asshole move on your part.  

“I’m a 21 year old college student here in the South and have been an avid reader/listener of yours for a long time now. Every time for the past two months my friends and I have met up to go out or just watch a movie, we’ve had a very heated argument over a very delicate topic. 


Half of our friend group believes the correct way is to plug the tip of your penis with your thumb right at the moment of climax to avoid making a mess. The other half believes that you finish on your stomach/naval area, then go clean it up. I’m asking your opinion on the matter and trying to stay as unbiased as possible. Like I said, when the topic gets brought up several minutes of screaming and arguing ensue. If you could settle this once and for all we would all be extremely grateful. 

Also, what percentage of the male population do you think utilizes each technique? It’s just so hard to fathom using the other way. It just seems so natural to you, and the other way seems so foreign.”

Plugging your penis at the time of ejaculation while masturbating is fucking absurd to me. Like this seems like legitimately psychotic behavior to me.

First of all, where does it go? Doesn’t it still have to come out? Aren’t you clogging up the pipes here by doing this for years and years? Do people actually do this? Not to cast aspersions upon anyone’s character but I’m pretty sure the people who put their thumb over their penis at the time of masturbatory ejaculation all do this are sex offenders. 

There is only one answer here: You have to masturbate like a gentleman.

You get toilet paper or a Kleenex, place it on your stomach, jerk off, and voila, no mess.

Any other masturbatory decision and you have no soul.

Send your anonymous mailbag questions to 

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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