Anonymous Mailbag

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Charlotte McKinney, Kliff Kingsbury

It’s Tuesday, time for the anonymous mailbag. 

Since all of you are here to laugh, I’m embedding my mom reading mean Tweets up top here. If you haven’t already seen it earlier this morning, it’s the perfect way to start off the anonymous mailbag. 

Happy belated mother’s day. 

Okay, here we go with the anonymous mailbag. 

“I’m married with two young kids and was lucky enough to break away for a date night this past weekend which resulted in drunk sex. During said drunk sex, I went down on my wife. As I was waiting to receive my act of reciprocation, she says, “I can’t do that with this thing in my mouth.” This “thing” she speaks of his an orthodontic appliance she had put in the roof of her mouth a few weeks ago. I was blown away (figuratively of course) that I had not foreseen the impact of this to our sex life. So my options are: 1) Brave the aluminum bj and see how it goes or 2) miss out on bj’s for the next 2 years (admittedly this is like 20 bj’s, but still)

What should I do?

Also, is “Can she still give head?” the single greatest question to ask at an orthodontic consult?”

Your final question sounds like it’s from a Will Ferrell movie. And I’m picturing that guy who always played the quack doctor on “30 Rock,” immediately responding, “Sure, she could, but she’s married now. No need.” Then giving an awkward high five. 

To answer your question: I think you risk the aluminum bj. 

Can it really be more dangerous than a high school girl who has never given a blow job before giving her first blow job with braces on in high school? And literally thousands of guys reading this mailbag right now took that risk and most of your penises are perfectly fine today. (Except for all of you with herpes, y’all are fucked). 

“Clay, I will come out and say it flatly. I spank the monkey at work with regularity (and have for 30 years without incident). What’s more, I consider it in the interests of my employer. Keeps me level-headed and on point. How common do you think this is? Should employers encourage it? Would it make sense for an employer to provide a masturbatorium for employees as a perk?”

What could go wrong with a masturbatorium? As someone who used to do sexual harassment investigations, I’m already thinking about how incredible it would be to ask this question of a boss, “So you thought, you should encourage masturbation at work and you created a room where you encouraged employees to masturbate during work hours? And you thought there would be no issues with that?” (The craziest thing about this idea is I’m sure they have it in some place like Finland. And if you talked to some Finnish employer about it, he would just say, “Ja, we masturbate at work. We’re not prudish animals like you Americans.” And everyone would think it was completely normal to masturbate at work in Finland.)

I would say that, conservatively, 75 percent of men have masturbated at work at some point in their working lives.

99.9 percent of all men will, however, deny it publicly.

As for women, it would be a much lower percentage. And a much hotter one.


I’ve recently started dating a guy and we’re both professional and in our early 30’s. Everything is going well. Our sex life is the only exception.

For one, he hadn’t been with a woman for years when we met and was out of practice. No problem. So when we first slept together, things weren’t very good, mainly because he couldn’t keep it up. He knew it.

Then as we got more practice, things did better and more consistent. However, he would still inexplicably lose the wind in his sails, and that’s when we both started to get frustrated.

To his credit, he went to the doctor and got some of those bright colored pills featured on golf tournament tv commercials. The first time he tried one out, I could immediately see and feel the difference. What miracle drugs! We were on our way to great sex. I don’t care if we’re young. Whatever it takes.

Since that time, though, he has rarely taken them, likely because his performance and the sex overall has gotten generally better. In his mind, he probably sees no need to take them anymore. But even on a good day, he’s rarely as hard as he was when on the pill. Plus if he can’t stay hard consistently, it limits what positions we can try.

We recently moved in together and hook up often. Almost every night, I want to ask him to take one but am worried I’ll hurt his confidence. Any advice on how I child encourage him to take the pills without hurting his feelings? Do you know many guys who go through this?”

Kudos to you for dating the guy who “hadn’t been with a woman for years.” I don’t know how that’s possible in your early 30’s if you have a decent job and you aren’t a serial killer, but maybe he was in the Catholic ministry and then bailed.  

The “my penis doesn’t work” industry is worth hundreds of billions of dollars. Yet everyone’s penis supposedly works fine. This means lots of people are lying about how well their penis works. 

Here’s the deal — Viagra and its competitors work so well that some college kids take it to last forever even when they don’t need it. Because, you know, unlike the rest of us college kids can just have sex all day and have no responsibilities and, I’m sorry, you’re all getting angry at work. And all you college kids reading this right now don’t even know how good you have it. Because you haven’t started work yet. Right now you’re all pissy because some boy or girl isn’t returning your texts fast enough and you think that’s a big deal. Boy are you about to be in for it.  

As for your problem, the only thing I’d be nervous about is whether consistently taking the pill will make him dependent on the pill for all sexual performance. So then what happens if you’re on vacation and he forgets his pills? What if it’s Mexico and he gets the wrong pills at the Mexican pharmacy and dies? Wouldn’t you feel bad then?

So I’d suggest taking the pills on special nights. Let’s say, once a week, when you have time to spend hooking up. The kind of night where you’d be willing to put on lingerie as opposed to having sex with your socks on.

You’re a new couple now, odds are you won’t be having sex every night in the future. That actually will make things easier for him because once you’re down to a couple of times a week — which statistically is likely to happen — then you can go with the pills on a more frequent basis. 

So the way I’d classify the pill taking is for “special nights.” You can help make those nights more special by doing more special things on those nights. I leave it to your devices to figure out what those things are.

What you definitely don’t want to say is, “I don’t like your penis as much when you aren’t on drugs.” Because a large percentage of erections are pyschological. And you don’t want to give him any reason to think about his penis not working.

“So, I’m a 23 year college graduate living near Nashville with an extremely complicated situation with my grandmother. Yes, you read it correctly, my grandmother.

Backstory: My grandmother gave birth to my father at the age of 15. She has since then had four children with four different fathers. She has been married eight times and has lived with 17 different men. Today, she is at the age of 54 and even though it pains me to say this she is honestly, smoking hot. In the wake of each divorce, she has had two boob jobs and botox done, graciously funded by her ex husbands. She is the true definition of a cougar. By the way, she is in a current relationship with a 24 year old. Say hello to my new grandpa.

Now, to clear things up, I am not involved sexually with my grandmother but she wants to be involved with one of my friends. How do I know this? Recently, my best friend and I traveled to her house to stay the weekend. Our first night there, my best friend is walking around with his shirt off and is looking at the pictures on her mantle. Nana walks up behind him and starts provocatively scratching his back and massaging his shoulders. Later, she tells him that if he ever needs “a place to stay” that their is always a bed for him there. What should I do? Never visit her again or ask her to stop? Thanks for your guided, gay, muslim wisdom.”

Sure, this question could be entirely made up, but the amount of detail in here is so well done I’m inclined to believe it’s true. Either that or this is just the plot of “Granny Bangers 48.”

I can’t believe I’m writing this but assuming this story is actually true: YOU CAN NEVER ALLOW ANY OF YOUR FRIENDS TO BE NEAR YOUR GRANDMOTHER. 


And I’m totally expecting for your grandma to be an Outkick reader and for her to send me naked photos next time I solicit mailbag questions.


“Gay Muslim,

To go along with the story of your son discovering that when he plays with his junk it gets bigger and daughter sitting next to the jacuzzi jet and saying it feels good, I have a similar story. I am the father of three boys, my wife likes to say she doesn’t live in a house she lives in a locker room.

Well. with that said one Mother’s Day a couple of years ago I asked the boys what we should get their mother. They came up with the idea of buying her an electric back massager. She constantly wanted me to rub her shoulders and the boys, taking pity on their old man, thought it was great idea.

So, fast forward about 6 months, I come home and there is my youngest son 8, sitting on the couch with the back massager on his junk, he looks at me and says “This feels so good”, next to him is my middle son 10, ” It does dad, you should try”. I ask whether their mother knew what they were doing, obviously she was clueless. When she did find out she immediately ripped it out of my sons hands and hid the thing. Needless to say she was traumatized, fast forward about 3 months, and my two boys are asking where the massager was, they wanted to put it on their junk because it felt so good.”

I can’t imagine what it’s like to be a mom of multiple boys, to raise your sons the best way you know how, to love them with every fiber of your being — and then see them slowly turn into penis obsessed teenagers with no regards for anything except chasing their own erections.

Once they hit their teenage years, a mom of three boys is basically living in a masturbatorium. You can’t open a closed door anywhere in the house without expecting to see an exposed penis.

I’m sorry, ladies.

The only consolation prize, I suppose, is that unlike teenage daughters at least your teenage sons won’t ever hate you.    

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.