Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag even though it’s the Tuesday after Christmas.
Yep, no days off for the anonymous mailbag.
Send your questions to, anonymity guaranteed.
I’m presently writing this from a Detroit, Michigan area hotel room where it is literallly zero degrees outside. Also, I have my nine, seven and two year olds running around me like wild banshees waiting for me to finish the mailbag so we can leave for the day and go watch some kid’s movie and go to the mall.
Yeah, awesome day coming.
“You’re the expert on all things male and I’ve got a question only you can answer. 
I was going through my storage room and found a box from college, this box had a lot of junk in it but also had one interesting item, my laptop from college.
Now in college I had two insanely hot girlfriends. Both of them were pretty damn sexy and pretty wild. While going through this computer I realized I had stored some naked photos of both of them on it and despite the computer being super old (circa 2007) and slow I was able to find the photos on a “hidden” file. 
I’m now married (to a different hot wife) and am 30+ years old with a kid.  Sex life is good but you never know when that may change. 
So my question is, do I keep this computer around and use it when I need it? Should I feel bad that I’ve got these pics and am excited I found them? Do I risk my wife finding the pics? Is it wrong of me to keep these pics for my spank bank? Am I risking her being super upset if she finds them? Do I transfer them to a new storage device so that I don’t lose them if the computer ever crashed? 
My wife was a freak in college so I can imagine she’s got pics like this floating around on one of her exes computer too sooo what do you think?”
Let’s apply the golden jerk off rule here — would you be upset if some guy who used to date your wife kept her naked pictures from college and occasionally jerks off to them even though he’s married to someone else now?
It sounds like your answer is no.
So I think based on the golden jerk off rule — jerk off only as you would be comfortable with others jerking off too — you keep the pictures and use them when you need a little bit of extra spice to your jerk off life.
Chances are your wife will not find your golden jerk off rule argument acceptable.
This means you have to leave the laptop effectively where you found it and she can never see you using it for any reason. If, for instance, you suddenly start protecting the old laptop or moving it to a more prominent place then your wife might get suspicious and wonder what’s going on. That way if by some chance she ever finds the old laptop and accesses the pictures on it because it turns out your wife is a computer sleuthing genius when it comes down to what you’re jerking off to then you can just play dumb and pretend you didn’t even know the pictures were still on there.
“What? That old thing? There are naked pictures on it? I had no idea.”
Now eventually you’re going to start worrying — what happens if my old laptop dies and those old pictures disappear forever. That’s why you have a really risky move you could make here — email yourself the pictures from the old laptop and store them in your private email account in a folder you don’t think your wife will ever find.
Whatever you do, clearly, and I can’t believe I have to say this, don’t share the photos or, god forbid, let them go up online somewhere.
And remember to always apply the golden jerk off rule to all facets of your sexual life.
“Holidays are approaching and with that comes family staying together.  Lucky for me my wife’s family has chosen to stay with us, at our house.  Now, my house is a very comfortable 4BR 3BA 3000 sqft house that fits my wife and 3 kids with no problem 51 weeks/year. But for the next week we are looking at squeezing in an additional 5 adults and 8 kids.  My wife and her sisters have come up with a very complicated plan involving air mattresses, sleeping bags, and floor space. They feel it’s better to be together, 24 hours a day it seems, and are apparently unfamiliar with the concept of hotels.   For my own sanity and personal space I am strongly considering going to hotel on my own.  This seems fraught with consequences on my end, mostly in the bedroom over the next few weeks, but I wonder if it’s worth it.  
It seems like a no brainer to me that they SHOULD stay at a hotel, but since they refuse, how big of an asshole move is it for me to disappear to a hotel?  Hope this makes the mailbag this week, I might have reservations to make.”
I am so pro-hotel when it comes to visiting family that I don’t understand how everyone doesn’t make this decision.
For instance, we are at a Michigan hotel right now while we visit my wife’s relatives.
Why are we in a Michigan hotel instead of staying with my wife’s relatives? Because I’m anti-stay in someone else’s house guy. This sometimes drives my wife crazy, but she’s just given up on arguing with me about it.
We just got to Michigan yesterday and my wife wanted to stay at her brother and sister in law’s house, but that house will be a goddamn zoo. Right now there are three kids at my wife’s brother’s house and another family visiting with their kid.
All in a four bedroom house with three cats. (I’m allergic to cats).
My wife wanted to stay there and I was like, FUCK NO!
Because inevitably I’d get the bed the cats sleep on and be using a pillow covered in fur and I’d literally be near death in the middle of the night because I couldn’t breathe. Plus, you can’t jerk off or have sex, it’s like being in sexual prison for a week. And god forbid you do decide to jerk off, inevitably an eight year old comes walking in while you’re treating your body like an amusement park and next thing you know you’re a sexual deviant and your eight year old niece or nephew is scarred for life.
It’s just intolerable.
As if that weren’t enough the kids would never go to sleep — the only thing worse than your own kids is your own kids with other people’s kids at bed time — and you can’t ever escape, it’s like you’re a perpetual prisoner in someone else’s home. Plus, and this is the kicker, once you get to the house you can’t leave no matter how bad it is because then you’re insulting their hospitality.
So I think it’s important to set this precedent early in your marital relationship — YOU ALWAYS GO TO A HOTEL UNLESS IT’S HER PARENTS OR YOUR PARENTS AND THEY HAVE A BIG HOUSE. (Or someone in your family gets elected President and you can stay in the White House or you are related to European nobility and someone has a castle.) Basically, the only exception I will allow here is if someone in your family lives in a holy fuck mansion. A “holy fuck mansion” is a house you pull up in front of and immediately say, “Holy fuck.”
Her family may think it’s weird initially when you don’t want to stay in their house, but before long you’re stay in hotel guy and it’s just part of who you are. (My wife was going to stay at her brother’s house with our kids before I realized I was off the radio the rest of this week and could travel up to Michigan and then I immediately told her to book a hotel room. Then she just told her family I was coming and they were like, “Okay, Clay’s a hotel guy, we get it.”)
As for your situation, you’re fucked. You can’t check your own self into a hotel no matter how miserable you are because it’s your home and your family and it’s clear you are effectively saying, “I hate all of you, leave.”
Here’s what I would have done if I were you in the days leading up to Christmas — book a hotel room for your visiting family. Find a hotel with an indoor pool and make it seem like the reason you booked that hotel was so the kids would have access to the indoor pool. Then, boom, you’ve cleaned out the house and you seem like a good guy.
 Honestly, I still think you could pull this off. Get on your phone right now and find a hotel nearby with an indoor pool and book a room there. If you really want to lay it on thick, book a suite. That way you become a hero. Everyone will think you’re being selfless, but you’re actually being selfish.
That’s the best kind of Christmas gift possible.
“Hoping you can set me or my co-workers straight on an internal debate we’ve been having. Last week I was on an important phone call in my office, with the door closed. In the middle of my call, a coworker knocks on my door (there is no window to my office so they can’t see me) and then after I don’t answer, they just walk in. Of course when they see me on the phone they just excuse themselves and walk out, right? Nope. They try to ask me a question and when I ignore them they start writing a note on my desk. With all of this going on, it threw me off my game for about 10 seconds and I probably sounded like an idiot to the person on the other side of the call. 
It doesn’t end there. About five minutes later, another person does the exact same thing, asking the exact same question. Both of them wanted me to join them in an ongoing meeting, which I was never originally invited to. 
So my question is, am I overacting thinking it’s unprofessional to just walk into someone’s office when the door is closed? If you knock, and and you are not invited to come in, is that not rude to just walk in anyway? Is it worse that the second person did the same thing knowing the first person told them I was on a call? Everybody in the meeting had their cell phones or a computer, so they could have easily texted or emailed me to join them when I was done with my call.” 
I’m sympathetic because my wife only asks me questions while I’m on the phone.
It’s like she waits until the exact minute when I’m engrossed in a serious phone conversation to demand the answer to something that isn’t very important. Or that she absolutely needs to call me while I’m on the radio. The other morning I was on the radio and she called me four straight times and I sent her to voicemail three straight times because she’s buzzing in while I’m a guest on another radio show.
I never send my wife straight to voicemail so you’d think she wouldn’t call me four straight times.
If you haven’t ever been the guest on a radio show when your phone is beeping with another call while you’re on the air it’s pretty damn distracting. When it happens four times in a row, it’s nearly impossible to manage.
Worst of all my wife used to call me while I was on the air during my afternoon radio show. (She’s never awake during my morning show now.) I’d be talking on the radio and I’d look down and my phone would be buzzing and I’d eventually call her back and point out that I was literally on the radio while she was calling. Sometimes she’d be like, “No, you weren’t, it’s on commercial.” As if I do nothing else during commercial breaks but sit around and return calls during the four minute breather between live segments.
And the question she would have would never matter at all.
Anyway, back to your question, I think it’s kind of weird to shut the door for a phone conversation. If you do this all the time your co-workers may have come to realize that you aren’t really doing anything important and are just on the phone. They may also think you’re on a conference call and not actively engaged in a call.
It seems to me the only real reason to shut the door to your office would be because you’re having a private meeting with someone and don’t want the conversation to be audible to anyone else.
So I don’t fault them for walking in even after knocking, but I do think they should write you a note instead of trying to talk with you.
I bet if I asked them why they did this their answer would be that you are “excessively shuts his door in the office guy.”
Also, how is there no way for anyone to see into your office? That’s crazy. Do you work in a broom closet?
“My wife and I are in our 40’s, together 20 years, very happily married with great careers and 2 great kids.  I’ve always been faithful and I’m fairly confident that my wife has too.  Sex life is very solid (3+ times a week) and occasionally a little kinky – toys and such. 
Sometimes when we’re in a particularly hot session after a night out, one of us will start some dirty talk and we end up talking about bringing a third or another couple into the bed.  It’s come up multiple times while we’re having sex and gets us both off on it but the only comment made the next day might be about what great sex it was, not about actually doing anything we’ve talked about.  
So, we’re headed to a party location (think Vegas, New Orleans, Miami) for a few days around New Years Eve and I’m wondering if the time is right to act on it.  I think we might enjoy the occasional walk on the wild side with another person or couple. And I’ll clarify the “other person” before you assume – yes, I’m open to it being a girl obviously or a guy (no gay stuff!) and us double-teaming my wife. 
I don’t know about flat out asking my wife if she’s down to actually do something while we’re on vacation because she’s a bit shy until the alcohol gets flowing and then she’s pretty wild.  If the wife isn’t agreeable I would immediately cease and desist as I’m not going to force the issue since our relationship and sex life is already great. Therefore I’m thinking the options are as follows. A) Do nothing and maintain the status quo. B) see if we can organically meet someone or a couple to pick up. C) post or respond to an add on Craigslist, tell them my wife doesn’t know and see if she bites on the randomly meeting a couple that hits on us in a bar or D) get drunk and see if she wants to check out one of the swinger clubs in that town.  I don’t have any desire to try this on our home turf – don’t want to take a chance on seeing someone we know. 
What say ye?  Other options?”
I think you’ve broken down the options pretty well here.
The big question is this — how much is potential sexual reality and how much is just sexual fantasy for your wife? That is, is your wife actually interested in following through on the fantasies the two of you are discussing? It’s clear that you are, but your wife may just consider this to be talk.
I’d suggest getting her drunk and posing the questions right after you finish sex next time. (Don’t pose it during sex because it might kill the fantasy. Have the good sex and then discuss it after while you’re both in a good mood).  Is this something she’s really interested in or just enjoys fantasizing about?
As for your options, b. requires no work at all on your behalf since it happens organically. So I think that’s fine regardless. And d. is fine too since you’re giving her the option to decide whether to check out a swinger’s club in town. The only one I wouldn’t do is set up c. That requires quite a bit of work on your part and I think if you get on Craig’s List she should be involved too.
I’d also add an additional option, go to Vegas and pay for a hooker.
That totally puts it in the fantasy realm and you never have to worry about seeing this hooker again. Plus, it’s Vegas and it’s like regular rules don’t apply there. Nor do you have to worry about feelings getting involved or next day awkwardness. You pay her and she leaves. (I’d also start with a girl over a guy. The girl is much less intrusive and women are often comfortable with other women.)
I think that’s a good way to put the proverbial toe in the water.
Good luck.
Send your questions to, anonymity guaranteed.
And happy holidays.

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.