Anonymous Mailbag

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It’s Tuesday, time for the anonymous mailbag. 

Let’s roll. 

“My wife is in an old high school friend’s wedding in a couple of weeks. She picked up her bridesmaid dress last Saturday and included were a pair of white thongs that had “bridesmaid” written on them. When she asked her friend about them the friend said they would be taking pictures with their dresses pulled up showing the thongs. Apparently this is a trend now. My wife said she was not at all comfortable doing this. However her friend told her she had to and no one else had a problem with it. I really dont have a problem with it but my wife wants me to step in and say she can not do it. Should I intervene or let my wife sort this out on her own?”

The world just keeps getting better. 

So now bridesmaids are getting their pictures taken together lifting their dresses while showing matching thongs? Is this a real trend? I’ve never heard of this before, but god bless women. How did this trend even start? (The answer is clearly with the hottest collection of sorority bridesmaids on the planet. After taking the picture they celebrated with a lesbian orgy.)  

To answer your question, you can’t forbid your wife from doing this because then you become the creepy, overprotective husband in the eyes of all of her friends. You don’t have a problem with it. If your wife does, she has to make her own decision here. Don’t intervene.  

By the way, how long until the groom is jerking off to this wedding photo of all the bridesmaids asses? What if he gets caught doing this?

“I have a sister-in-law/masturbation dilemma.

Last summer I took the wife and kids to the coast for the weekend. We brought along my sister-in-law, who has been divorced three times but is currently between guys. So it was kind of a charity case, except she’s actually pretty fun: she likes to drink and she’s reasonably attractive (think Courtney Cox but shorter with bigger boobs).

On Saturday morning the entire crew headed out for shopping and lunch. I didn’t go, for reasons that require no explanation. My pursuit of other options led me to my sister-in-law’s room. When she unexpectedly returned, that’s where she found me, holding one of her bras in my right hand (36 DD — I looked….) and polishing the trophy with my left hand. The ensuing conversation was brief and mostly one-sided: “What the hell are you doing? Get out of here!”

I spent the rest of the weekend trying to avoid her and hoping all would be forgotten. But in the following months she has raised the incident several times, asking what I was doing, why I was in her room, and what I’m doing to address my masturbation “problem.” She sometimes alludes to telling my wife about the incident so that I will “get the help I need.”

So what to do? I can preemptively tell my wife. But I don’t think that would go well. There’s the embarrassing details, of course. Worse, however, is that my wife has always been jealous of her younger, hotter sister. Another option is to do nothing and hope that my sister-in-law will keep this between us and won’t choose to blow up my marriage. A third possibility is that my sister-in-law is actually getting some titillation out of talking to me about masturbating and she’s just toying with me, so to speak. If you can pull yourself away from the golf course and the mosque, maybe you can help.”

Eliminate the third option from your mind. 

There is no woman on earth who would be titillated by coming home to find a man masturbating while holding her bra in his non- masturbating hand. Only a man would even think that a woman could find this titillating. Here’s an easy test for you — ask yourself, would this be creepy if a girl saw George Clooney doing it? If the answer’s yes, then you’re really doing something creepy. 

What a mess. 

I’ve never been the kind of guy who gets turned on by women’s underwear — without the women inside — but I guess this isn’t that uncommon. So to each his own. I won’t judge your sexual perversions so long as kids aren’t involved.

I don’t even know how you address this with her. I think it’s almost so awkward that she’s afraid to tell her sister, your wife. So I think that’s an empty threat. The next time it comes up I would just apologize to her and say that you are getting help for your attraction to women’s underwear. If she presses you for what kind of help, just say that you’re going to counseling. 

Good luck.  

“One of my best friends from college is making moves on my younger sister. They’re going out on a date soon. He hasn’t discussed this with me at all.

Now he’s a good dude, but I know his sexual history and let’s just say that he’s had way more partners than I’d want the guy dating my sister to have had. He’s a good guy, but not the guy I want my sister to date. What do I do?” 

I think the answer here is pretty simple: Your only play here is total disclosure to your sister. Tell her everything you know about your friend and his past “relationships.” Once you tell her everything then it’s on her to make a decision about whether she wants to be involved with him.

I don’t think think you owe him anything because — HELLO, IT’S YOUR LITTLE SISTER!

He’s the asshole who has to pick his friend’s sister to date. (She must be really hot). Tell her everything. Then you can tell him that you told her everything. 

Pray she’s smart enough to pick someone else.  

“Spent a great night drinking on a business trip to Vegas….passed out in my hotel room and woke up in the middle of the night (around 4am) to use the restroom. Instead of walking into the bathroom, ended up in the hallway….in my boxers….with no room key. Took a while to shake the cobwebs to realize where I was. The only place to get a replacement room key is at the front desk. Jump on the elevator down to the lobby assuming it will be dead at this time of night. The doors open and there is a huge crowd waiting to get on the elevator. I’m standing there in my boxers….so I just ran. I found a service elevator and took it back to my floor and see the phone next to the elevator to ring security to let me back in my room. This has to happen to others…right?” 

Yeah, I’ve actually thought about this happening to me because I’m on the road by myself quite a bit. It has to happen a decent amount of times, right?If you’re at a hotel that’s nice enough to have a phone by the elevator you just call down and explain the situation. Sure, a couple of people might see you in your underwear, but you just shrug and explain what happened. If there was no phone I’d just own it and walk down in my underwear. What else can you do? 

Now the really awful situation would be if you got locked out of your hotel room naked and there’s no phone on your floor. I’ve actually thought about that happening too. What should you do? The best option is to try and find the service closet on your floor and grab a sheet or towel. Next best option is room service outside another room. There are sometimes sheets on the tables there. Worst case scenario you could grab a napkin or tray and cover your groin. If there’s no room service, no phone on the floor, and no service closet then I think you’re really screwed and you have to go down naked.

Someone reading the anonymous mailbag has to have gotten locked out of their hotel room naked before, right? What did you do? 

“A few years ago in Corpus Christi, Texas, where I was living at the time, my gay guy friend comes over on a Saturday night. We were gonna hit the bars. He pulls a little party bag out of his pocket which may have contained some cocaine. He says try some of this! I say ok buddy! So I go in the bathroom and do a couple of lines.

When I come out, he’s got his dick out masturbating to the local weatherman Alan Holt! I was shocked to say the least! Alan Holt is not even that cute. So, I’m like WTF!? Dude! Put that away! But he’s really going at it! He must have pre-gamed quite alot before coming over. He does not even care or stop! I didn’t know what to do, so I called a cab driver that I knew and said “oh look! Your cab is here!” and hustled him out the door!”

All I could think to do after I read this story was look up local weatherman Alan Holt. 

Here’s his Facebook page. 

If you were gay would you jerk off to this guy?

Keep the anonymous mailbag questions combing. 

Total anonymity guaranteed. Email me at 

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.