Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

I’m moving fast this morning because I have to be finished with the mailbag in time for Outkick the Show at 2 eastern today. Thanks for everyone who came and hung out during the show yesterday. We had over 200,000 of you for our broadcast. Also thanks to Joel Klatt, Petros, Matt Leinart, Reggie Bush, Braxton Miller, Trent Richardson, Barstool Big Cat, Kayce Smith, Laura Rutledge, Mattie Lou, and Elika. It was lots of fun.  

At least until we got backdoored by Clemson with 12 seconds left. Not gonna lie, that one hurt a ton. 

I’m traveling back to Nashville on Wednesday and we’ll have a special evening edition of Outkick the Show discussing “Making a Murderer” on Wednesday night. Yep, Outkick primetime. So finish “Making a Murderer” if you want to participate. And then go read my column so you’re ready to discuss things.

Send your anonymous mailbag questions to

Okay, here we go:

“I need the advice of a Southern Gay Muslim regarding some accidentally discovered pornography belonging to my father. My father has currently started reading your columns so keep me anonymous please. I currently go to an SEC school and came home for the holidays. I borrowed my father’s old gym bag to workout over the break and brought it back to school after the break on accident. While unpacking, I came across an old school DVD titled “Sexy Sluts 6″ in a side pocket. I obviously found it hilarious at the time until my Dad asked me to bring the bag back to him the next time I come home….My question is whether or not I should throw the DVD away when I give the bag back and assume he forgot about it (the bag has been in his closet for years), or give it back to him with the DVD in the pocket and let him find it himself? I feel like he would be slightly embarrassed if I left it in the bag because he would know that I noticed it. I secretly would like to leave it in the bag though to make him sweat it out. To further this discussion I also wonder how many 40-60 year old men still use DVD/VHS pornography? I am not the first one of my friends who has discovered DVD or VHS porn from their father.”

You should text your dad — if he texts — “Will drop off gym bag soon. Do you want “Sexy Sluts 6″ back or not?”

I’m going out on a limb here and going to guess that the order you watch Sexy Sluts isn’t that important. For instance, you aren’t missing major plot points by just skipping ahead to number six. 

Also, your dad is reading the mailbag right now and just discovered that you found his old-school porn, which is perfect. Just be glad it wasn’t a homemade sex tape of he and your mom. 

As for what percentage of men still use DVD/VHS pornography, I think it’s low. How many people even still have VCRs? Or even DVDs? On demand and streaming just crushed that technology. So I’m going 10%. And you have to go over the age of sixty for that too. There’s no way that any forty year old man is jerking off to anything other than Internet porn.  

“My soon-to-be wife and I are a great match for one another. She is beautiful, smart, ambitious, funny, and comes from a rich Southern family. Aside from our families, we have had very familiar life experiences except for one thing – our “number.” While her “number” was not and is not important to me, she felt compelled to ask me very early on in our relationship. As soon as we slept together for the very first time, as we were both basking in our respective exploit, she nuzzled into me and asked in an innocuous way: “How many girls have you slept with?” I was caught off guard and answered immediately and honestly, without using any reason or logic, the correct answer.

I had been a degenerate in the past and had slept with my fair share of women with loose morals. I had previously lied to girls in the past about this question but for some reason answered her truthfully. She was not pleased. She tensed up and pulled away. For a slim moment I was proud of myself for being forthright and honest, because after all, that is what lasting relationships are built upon, right? Then, she asked if I wanted to know how many she had slept with and I replied no, that I wasn’t interested. My answer did not stop her. She continued to tell me that she had only slept with three men, including me sixty seconds ago, and continued verbatim that she had “given a lot of guys blow jobs…like A LOT.” We lay in bed silent for a couple of minutes and then got up, began our day, and never spoke about it again.

Fast forward five years later: we have never talked about her comment but I think about it every time she gives me a blow job now and almost every time I meet one of her guy friends from college. Should I have lied and said that I had only slept with a handful of girls in my past? If so, she would have surely replied that she had only slept with three guys and all would be well in the world. As we are getting married in February, this won’t apply to me, but will apply many of the single guys out there: Should men lie about their “number”? If so, should you round up, down, or try to predict a “number” that matches your respective lady friend?”

I think you predict the number initially and try to be close to what you think your partner’s number is. If you feel guilty about this later, you can clarify, but, honestly, this conversation isn’t that important in the grand scheme of things once the relationship gets rolling. So if you’re dating a girl you think is virginal and church going, you shoot low. If you’re dating a porn star, you try to make it seem like you can barely avoid having sex every time you leave your house. It’s all about trying to be roughly equal.  

If you are bad at predicting my general advice would be to say you’ve slept with nine people. It’s less than double digits, but not a small number. It seems totally average. Totally average numbers are tough to get very worked up about. 

One caveat: It’s totally acceptable for all guys to follow their (reduced) number by saying, “I mean, I could have slept with a lot more girls, but I only have sex with the girls I really like. Like you.” This will probably be a total lie, but she’ll believe it and probably sleep with you again.   

Good bar debate: would you rather your wife or girlfriend have slept with 100 dudes and blown four or slept with four and blown 100?

For women, would you rather your husband or boyfriend have slept with no girls when you started dating at the age of thirty or 25?

Secondary good bar debate: is there a number of people that your present partner could have had sex or oral sex with that you would end the present relationship? And what is that number?

“So we have discussed multiple items about proper gym etiquette. I ran across another one this morning and I’m curious if the guy is a genius or not.

This morning at the Y I see an old guy spreading his ass cheeks with one hand and blow drying his asshole with the YMCA’s hair dryer.

Have you seen this play yet? Should I avoid this altogether or just save it until I get to an age that having hot air dry my asshole is the best part of the day before I get dressed?”

My first thought is — how wet can your asshole possibly be? At no point in my life have I ever thought that after getting out of a shower and toweling off I have to get my asshole drier. That’s never even occurred to me.  

My second thought is — would this feel incredible? So incredible that I’d be willing to blow dry my asshole in front of a large group of men? And that the only reason I haven’t tried it is because a. I don’t own a hair dryer and b. I’m unwilling to do this in a crowded gym? It has to feel pretty good, right? I mean, a blow dryer on your hair feels great, what would a blow dryer on your asshole, with warm arm also rolling around your grundle and caressing your balls feel like? 

My third thought — you have to bring your own blow dryer to the Y. How in the world do you use that blow dryer next after the guy dries his asshole with it? 

Fourth thought — how much funnier is this to see if it’s a wall blow dryer that is timed out. And the old dude keeps redoing it again and again? Total Steven Avery move there, you know. 

“I need your advice. I am a happily married man with 2 beautiful children (ages 6 & 4). However, I find myself on many occasions having a Will Ferrell counseling moment from “Old School” when he is supposed to be in the “tree of trust” Just like the Will Ferrell character when I see a hot woman I sometimes wonder what type and color of lingerie she is wearing. From a gay muslim who has to see his fair share of hot women working in TV, what is your thought on this?”

Everything about the movie “Old School” is hysterical, but the Will Ferrell scenes are heartbreaking because they so perfectly encapsulate the married man mind. 

Watch this scene and tell me it isn’t sublime. 

And how about this one about his Saturday plans?

The simple fact is this — being married is much less fun than being single. It just is. Now there are good things about being married, but when it comes to pure, unadulterated fun, marriage isn’t as fun. And that’s no matter who your wife is.  

“Hello oh mighty great one. I need your gay homophobic Muslim wisdom regarding the female gender. So I’ve had a best friend who happens to be a girl all throughout high school and college. We’ve been through it all. I’ve held her hair while she blew chunks off a balcony, she’s pretended to be my girlfriend to help me escape crazy women at the bar. She’s like my twin sister. Anyways, her roommate wants to bang my brains out. Her roommate is a very beautiful woman, but doesn’t want a relationship. My friend would be totally fine if I took her on a date but would rip my pecker off if we just hooked up. I don’t want a girlfriend either but want some sex. What’s the play here?”

The subtext of this email is glaring: Do you actually like your best friend as something more than a friend?

Because if you do then tell her you like her and see what happens. 

Otherwise, I don’t see this as a difficult decision at all, hook up with the hot roommate.

Honestly, upon further reflection, I would hook up with the roommate no matter what. It it makes your best friend jealous then she likes you too. This is how all great relationships begin — by hooking up with other people.  

“Got a question regarding dealing with my girlfriend and strippers. I honestly am not a big fan of the strippers I am 26, I have been there and done that (maybe growing up in a town of 3,000 and watching the strippers there may have had some impact) but I am getting to a point where my friends are starting to get married which means bachelor parties and the possibility of strippers. Well over the last few months my girlfriend is struggling with the stripper issue, she absolutely despises the strippers and thinks it is disgusting and demeaning to her. I have told her numerous times if the bachelor party goes to the strippers I am obviously going to go but I don’t need to get lap dances or anything of that nature and it doesn’t seem to have much impact on her levels of rage when discussing the strippers. What would you say or do?”

If you’re 26 and your girlfriend is worried about strippers at bachelor parties, you need a new girlfriend. This isn’t so much about you going to the strip club is it is her trying to control you. 

My position on this — and every woman should read this — is it’s much easier for bachelor parties to pick up girls outside of strip clubs than it is inside strip clubs. That is, sex is more likely when a group of bachelors goes out to a regular bar than it is to a strip club. Girls who are opposed to strip clubs on bachelor party trips are fighting a dumb battle. You should want the guys in the strip clubs and away from the regular girls. The regular girls are the ones that cause the problems. 

“Going on a ski trip next week, condo address is on Robert E. Lee Blvd. What is the correct PC bro reaction?

1. Form a protest at the front of the street not letting anyone come or go until they change the street name.
2. Form a protest demanding HOA presidents resignation?”

Wait, they name streets after Confederate generals in places where you can ski?

Big news on the PC bro front, the state of Wisconsin has banned students from chanting air ball because it’s too mean. This is incredible because you can’t even satirize PC bros now. PC bro culture has so taken over that the most patently absurd thing you can think about is actually becoming reality.  

“Is it acceptable to rub one out in your own home while you have family staying over? How about if you are away from your home turf at your siblings? At the in-laws? How about grandparents if they are still alive? Your own parents?

If that is acceptable, are there any caveats? Only in your bedroom? In the room you are staying in? In the shower/bathroom?”

It’s perfectly acceptable to masturbate in any location so long as you are solo.

Unless you’re a guy in a sorority house having a group masturbation orgy with all the girls there, which is also acceptable.

Related: I hate you.  

“While not a connoisseur of the genre, the occasional adult film scene has made its way onto my computer screen, as well as my friend’s. We were discussing the basic structure of an adult film scene and I mentioned how ridiculous it is. Every scene is blowjob/sex/blowjob (that the woman seems to really enjoy) until the guy finishes. In the real world, there are usually no blowjobs before sex, and certainly no post sex blowjobs. I said this pattern occurs in less than 1% of all sex between married couples. My friend thinks that, although his wife wouldn’t ever do this, this pattern occurs in approximately 15% of all married sex encounters. He bases this on a theory that there are plenty of ex-strippers and women who bring nothing to the relationship other than great tits and a morally casual attitude that landed some chump. In fact, he thinks it may increase the longer those marriage go since a stripper/hooker/trophy wife might up her dirtiness game to avoid getting traded in for a newer model.

Since we both read your site, I thought I would ask you to be the neutral arbiter so that I may taunt him in writing and generally demonstrate my overall superiority in all ways to him.”

You’re right and your friend is wrong: I say it happens in less than 1% of all marital sexual encounters. 

Also, am I the only guy who thinks watching a blow job scene in a porno movie is incredibly boring? And they last forever. It just seems like the porn star is totally showing off. “Oh, I get so many blow jobs that they don’t even do it for me.” Thanks, asshole.

The rest of us married schlubs are out here blow drying our assholes for sexual fulfillment and you can’t even orgasm from a blow job.

I hate you.

Send your anonymous mailbag questions to Full 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.