Anonymous Mailbag

Videos by OutKick

Charlotte McKinney, Kliff Kingsbury

It’s Tuesday and you guys continue to inundate the anonymous mailbag with incredible questions. 

I read all of your questions and try to pick out the best questions. Of late, people have also been asking for updates. So for those of you whose questions appear in the mailbag, if you can update us with what happens after the mailbag, many would appreciate it. Because, of course, we’re all one big dysfunctional family here at Outkick. If you send an update, please link the mailbag your question appeared in so I can easily link back to people and not have to search for them. 

As always, send your questions to

Here we go. 

“Over the last couple of years my porn taste has transitioned from typical pornstars screwing on camera porn to live amateur webcam porn. The site I typically go to has around 1,000 live models online at any given time. These models all vary greatly on how much they are willing to do on cam and how much they interact, if any, with guys outside of the site. In addition to doing the live stuff, a lot of the models also make videos and sell them on the site.

There is one model, whose room I have been into maybe 5-10 times, about to make her first sex video, and it’s a threesome video with one of her girlfriends and some random dude she met on Tinder. At one point I made some generic comment, like “I’ll probably get the video, but I’m going to be jealous of this bastard in it.” Normally when you say something like that, you’ll get a laugh and a generic reply back. Well, that’s not what I got. What I got was a very matter of fact sounding answer back, and I quote “Come to [insert City name] and we will make a threesome video with [insert other girl’s name], and you can put it in my butt.”

Normally I would be 100% sure that she was just playing the role here, but this wasn’t the first time she had made a similar comment to me. I decided that next time I was in her room, I would throw the bait out once more, and if she said the same thing then I would ask if she was bullshitting around or was serious. I did and she did, and it turns out she is 100% serious.

Here are a few things to consider:
1. She has been with over 20 guys and says that condoms are a buzzkill. Her friend lost count after 50.
2. I have a good career that I would like to keep.
3. She knows what I look like, so she’s not going to change her mind based on looks.

Apparently this is where I call you a gay Muslim. So, I need your advice ya big liberal conservative racist sexist homophobic gay Jewish Muslim. Do I fly to her and make the threesome video? Do I try to just screw them without doing the video? How inappropriate would it be for me to straight up ask her if I am going to catch something without a condom? Would it matter if I am still flying with my V-badge (hypothetically, of course)? Please help!”

So you’re asking me whether you should fly to a different town to lose your virginity on camera with a web-cam girl and her hot friend. 

Welcome to the anonymous mailbag. 

Selfishly, I want you to do this and write about it for Outkick because it’s an amazing story. But I’ll be honest, I’m terrified that you’ll wake up in a bathtub filled with ice without one of your kidneys. And I want to make sure we keep getting your pageviews at Outkick. 

As a general rule, I’m of the belief that if it seems too good to be true, it probably is.

This certainly seems too good to be true. Presumably this web cam girl is hot, right? (Confession: I’ve never watched a webcam other than a few videos that have been published on PornHub. I feel like once you get into live webcams you probably never stop and I just can’t stomach being a 36 year old dad with three kids, buying fake Internet coins to give to web cam strippers so they’ll say my name out loud while they screw themselves with dildos. That’s where I draw the porn line. I like my porn the old-fashioned way, on my iPhone 6.) But, nerd alert, I have read about web cam girls in the New York Times and the New Yorker so I have a general sense for how the business works. 

Having said that, sometimes you just have to stop and ask yourself — why would a girl who makes tens of thousands of dollars off being hot on a web cam be willing to sleep with her hot friend and some random guy she “met” on the Internet? What’s in it for her? Presumably finding sex partners isn’t difficult for hot girls on the Internet. Even if we presume that she finds it hot to bang random guys who jerk off to her on the Internet, there’s still a ton of them available, right? In fact, this is actually every guy she knows on the Internet. What makes you more desirable than every other guy online? (You also said she knows what you look like, which means you have sent pics to a web cam girl. Good luck with that.) If she were really smart, she might be thinking that a video of her and her friend screwing a random web cam customer might sell better in a — this could be me, fantasy context — but, again, aren’t there tons of guys this would apply to and, if she were really smart, would she really be a web cam girl? Can’t you make much more money stripping in Vegas?

Anyway, I just come back to this question — what have you done that makes her willing to do this with you?

My guess is it’s a scam and once you arrive in town the absolute best case scenario for you is that they’ll try to get as much money out of you as possible to have sex with them. (I think prostitition should be legal, so more power to you if you pay them for sex, but I’d be afraid that they might drug and rob you given that you’re probably not likely to call the police in a strange city and report that the web cam girls you paid for a threesome, weren’t actually as honest as you thought they were).  

But if all this materializes and you find yourself with them, why in the world would you do it on video? You’re not a pornstar. Do you really want a porno video with you in it out there for the rest of your life?

And regardless of what you do, for God’s sake, wear a condom. I’m not sure which is worse, catching herpes from a web cam girl or the inevitable “I’m pregnant and need money for an abortion scam.” 

Update us on your decision, please.  

“You’ve been on a roll lately with the latest anonymous mailbag bachelorette party story (Holy shit I want that story to be true) & the car trip to Florida. Anyways, question for you. A couple of buddies of mine and I were sitting around late Saturday night, drunkenly debating random topics. One of the guys is on the practice squad at a major SEC school. He brought a friend, who happens to be one of the best players on the team. (Player description redacted). The following question came up:

Throughout his collegiate career, how many girls does your SEC star player(s) sleep with? Now I know there is a lot of variables here, so we assumed the player stayed for at least 3 years, was not in a relationship (not that this matters), and is considered one of the Top 5 players on the team.

All kinds of numbers were thrown out on our side. Hell, at one point you would have thought every player was Magic Johnson like and slept with thousands of women.

Thoughts? Over/under?”

This is the ultimate SEC guy debate. If you haven’t had this conversation with friends of yours before then you probably aren’t reading the mailbag and you probably didn’t have any friends in college. 

My answer: It’s totally a question of how many girls that player wants to sleep with. I’m not even kidding about this. I think a star SEC football player — with decent social skills, an active social media profile, and available time — could easily average five girls a week for an entire year. (This would take into account multiples, which I think would happen pretty frequently too and it would also count blow jobs as sex.) Five different girls a week all year around would add up to roughly 260 a year. Over three years you’re talking about 780 girls. 

There’s just no doubt in my mind that would be easily doable. Amazingly, that could be low. Again, it’s a question of how much time he wants to devote to chasing girls. If he were just really active on social media — Twitter, Facebook, Snapchat, Instagram — I think he could hit that number just off girls there. I bet you’d be stunned by the number of women who didn’t even go to the college he attended who would show up just to have sex with him.

I would love to read a star SEC quarterback’s tell all book about his life off the field one day. Can you imagine what, for example, Stephen Garcia’s book would be like?

“Please keep this anonymous as I am in a bit of a bind. I doubt my husband knows who you are but we have a lot of friends who are fans. Fun fact: I bought “Dixieland Delight” after seeing you discuss it on one of those morning shows when it was first published.

My (possibly soon to be ex) husband and I attended and met at a large and obnoxious southern school many years ago. As any good alumna, I joined the alumni association and made annual contributions to the school to get the standing and points necessary to get football tickets. Eventually, enough older folks die off and/or the team started sucking enough for spots to open up for new season ticket holders. My husband wanted none of it and had no interest in season tickets, despite paying outrageous prices for scalped single game tickets.

Anyway, recently I was able to finally purchase my season tickets. Adulthood does have its perks. I am excited to be able to go to a game and sit in seats with chair-backs vs those god awful bleachers that are 100 degrees at all times and next to some chick who always looks like she is about to die or vomit all over me. Side Note: I was that chick once but now I’m older and full of judgment. Get off my lawn!

Guess who is ‘totes’ interested in the season tickets now? The tickets are in my name; I solely paid for them with my ‘pool’ of money. I am thoroughly convinced that splitting up the home game tickets would be worse than any possible divorce proceedings and would rather run them over with a lawnmower than give them to my soon to be ex-husband. What claim do I have to them? I doubt this situation is unique knowing the divorce rate. I want to discuss the flip side too. If we stick together should he automatically be my +1 to every game or should I be able to invite friends or family without feeling like a total dick? Any comments from ‘youre’ gay muslim pov regarding my ‘first world problem’ are appreciated.”

Believe it or not, this is actually a pretty common dispute when couples divorce — who gets the sports tickets? The easy rule is the tickets are marital property and each side would be entitled to half. So you’d get half the games and he’d get half the games. (No judge outside of a sitcom would be so cruel as to require you to each get one ticket and attend the games together for the rest of your lives). The funniest thing about splitting the tickets, is it requires you to interact each year over who gets the good and bad games.  

If the tickets matter a great deal to you, the division of marital property is subject to negotiation. That is, everything can’t be split evenly. What does he love a ton that you don’t really care about? A dog, a golf membership, a boat, I’d claim you want half of something you know he wants a great deal too. Then, as the negotiations continue, I’d angle to get the tickets all for yourself by being willing to give up your interest in something he loves. 

The important thing to recognize is it’s really hard to demonstrate that you paid for the tickets and they should be your property. The only way I could see that working is if you had the tickets before you were married or you inherited them. Then they wouldn’t necessarily be marital property. But in this situation you got the tickets after you were married. Which means he would have a claim on them.  

Also, if your husband doesn’t know who I am, you really should divorce him on the spot. What’s he doing with his life?

“I figured you couldn’t help but open an email with the subject of “boobs.” Secondly, I cannot get over this Game of Thrones episode, and I am jumping the gun on the anonymous mailbag but I just couldn’t help it. I need to give a little background. I attend Ole Miss, and even before I left for college, GOT was a family affair every Sunday night. Now here is the issue: although I am already in college and my only brother is going to be a senior in high school, my mother is still persistent on us not watching whenever there is a sex scene or a beautiful red head with perfect boobs on the screen.

So with tonight’s episode, it caused a fairly significant commotion in our household on whether or not I should have turned away during Cersei’s long and somewhat disappointing walk. My girlfriend of over a year and a half did not seem to care, but my mother was insistent.

With everything available at my fingertips, why is this still an argument and how do I combat this nonsense?”

You’re in college and your mom makes you turn away during nude scenes on Game of Thrones?

Totally unacceptable. 

(I also love that you said your girlfriend doesn’t care. Like it’s possible that she could care about you seeing boobs on television. Are there guys with girlfriends who make them turn away during nude scenes? If so, end that relationship right fucking now. I mean, immediately.)

I’m not sure when I’d be comfortable watching “Game of Thrones,” with my kids — the answer might be never. But you do raise an interesting question, given the modern Internet generation’s ability to find porn, what’s the appropriate age to watch “Game of Thrones” with your parents? My guess is 13 or 14. 

Twenty years ago you or I busted our asses to see airbrushed Playboy models. Nowadays kids have seen videos of gangbangs by the time they’re 11. 

I’d honestly be much more concerned about the violence than I would the nudity. But I get that if you did start watching the show with your kids when they were young teenagers that you might have a rule like that to make you feel better about your parenting. 

But that rule would certainly have to end at some point. 

And that point would have to be before college. 

So I think you tell your mom, “Do you know what I see every weekend at Ole Miss, mom? “Game of Thrones,” is tame. I don’t want to stop watching the show with you, but I will if you keep making me turn away during nude scenes. That’s much weirder than just watching the show.”

The other option, of course, is pretty simple — just don’t watch the show with your parents. 

“Having been a regular Outkick reader for some time, I feel compelled to submit this story for the Anonymous Mailbag. This incident occurred a few years ago, and constitutes a perfect example of the hazards of tailgate related activities. To this day it still the single most heinous thing I have ever seen. Please keep my identity anonymous.

While I was graduate student at a large Big Ten University, my friends and I were tailgating in an area occupied pretty much only by other students. I probably don’t need to explain the general debauchery that occurs in these areas…In any event, at some point I wandered over to the porta-potties to relieve myself, and ended up standing in a pretty big line.

Just as the obnoxiously drunk students in front of me were starting to get on my nerves a little bit, one member of said group entered a porta-john. The drunk kids thought it would be absolutely hilarious to rock it back and forth while he was inside. Of course, they got a little bit carried away and tipped it over.

Fortunately for the kid inside, the door was facing up. Unfortunately, when he opened the door, the hundreds of people in this area got to see him emerge absolutely covered in what I can only describe as the most disgusting mixture of human body fluids and waste imaginable. After a few seconds of shocked silence, all of the bystanders started laughing uncontrollably. The victim stood there in shock for what seemed like forever, and then took off on a dead sprint…presumably for a car wash or something.

This has to be one of the worst things someone could do to another human being right?”

I think — if the victim desires it — you should have to go to jail for a month if you turn a porta-potty over while someone is inside. 

Is there anyone who doesn’t think the culprits would deserve a month in jail for this?

If this happened to me, I would tackle every single person who tipped me over and rub my filth all over them. If I’m going to die of blue feces, you are too. This would also ensure that none of them got to go to the game either. 

Honestly, this story makes me never want to go into a porta-potty ever again. 

“Please keep me anonymous, as even though I live north of the wall, I’ve turned quite a few people onto Outkick.

I was recently declared the judge of a bet between two friends, and I have no idea how to settle it, or whether or not we even should. The bet is whether or not our early thirties female friend is a virgin. There is only $100 on the line, so not a huge amount of money, but still significant.

A little background: She’s good looking, has a good job, in great shape, but isn’t fairly outgoing until you really get to know her. Although she doesn’t drink, she hangs out at the bar with those of us who do. We know she has never had a serious boyfriend, but has dated a few guys for a couple of months.

My question is this: how in the world do we settle this bet? She has a few close girlfriends who are also friends with the guys who made the bet, and we feel like they would know, because unless it’s bachelorette parties, girls talk about everything right?

Option 1: Ask the girlfriends. I feel like this could be accomplished with a little discretion, but even if they answered, can we trust them? I feel like if my friend was a virgin, and someone asked me, I would say “no, shes not” to protect them from being “weird”.
Option 2: Someone gets drunk and ask her directly. The guy betting on #TeamNotVirgin has offered to do this. Going right to the source is probably the best way, but I feel like we are making a big risk to the friend group to asking the question, and we would need a witness there to verify whether we can believe her answer.

Racist gay muslims must be obsessed with peoples’ virginity, so hopefully you can help me out. Is it worth it to settle this bet? And what’s your best strategy for finding a winner?”

I think you go with option three — make up a list of several sexual over/unders involving your friends and place bets on all of them.

Everyone gets to come up with a sexual bet for everyone else. (Note: you cannot include the person in setting the bet and you can’t allow someone to set the line based on something they already know the answer to. You demand honest answers from all participants regardless of the question).

So if there are six people involved, you kick out the sixth guy or girl and the five of you come up with a bet that half of you would take and the other half wouldn’t. It doesn’t work unless you can come up with a bet that half believe and half don’t. 

Hers would obviously be — is she a virgin or not? Half are saying yes, half are saying no. 

Someone else’s might be — has he ever had anal sex? Has she ever hooked up — a hook up is defined as nudity or penetration — with another woman? Over/under of 10 for sex partners?

This way the potential virgin girl isn’t singled out and you actually have a pretty fun drinking game to play. 

Everyone wagers $10 or $20 on each bet. 

It’s like never have I ever, but with bets attached. 

“Please keep this anonymous.

This isn’t a question but a verification from Friday’s mailbag. Michael Jordan’s penis is much bigger than LeBron’s. In fact MJ’s genitalia is larger than 99% of the population.

As for how I know, my mom’s friend dated (assistant coach’s name removed in case he was married) back in the day (in hindsight the lady might have been a road piece. I’ll have to check with my mom). He was a super nice guy and took us into the locker room once in the Doug Collins era. As a white boy just entering puberty, it was eye opening. All the guys were big but Jordan dwarfed them all. His baggie shorts suddenly made sense. No matter what LeBron does he will always come up short against Jordan in one category.”

I’d like to say I’m surprised that one of you wrote in to tell us about Michael Jordan’s penis size as it compares to LeBron’s penis size, but I’m honestly not surprised at all. 

Email your questions to

Anonymity is always 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.