Anonymous Mailbag

It’s Tuesday, time for the anonymous mailbag.

I’m writing this in Denver while my youngest kid takes a nap so let’s get rolling here as fast as we can and hope I can finish before he wakes up.

As always you can send your anonymous mailbag questions to

Here we go:

“My current masturbation protocol is fairly innovative. I use a room chair to take to the bathroom, face the toilet, prop the laptop on the head of the toilet, do my business, and immediately flush the product. No mess afterwards on towels, socks, etc. Everything goes straight into the toilet and the toilet paper is right there for any detailed cleanup. Very eco-friendly I believe as my laundry requirements are now lessened. My buddies classify this as innately psychopathic behavior. What say you?”

I think your friends are correct — this is absolutely psychotic behavior.

Here’s the easy way to think about things like this, if someone caught you doing it, what would they think? Clearly, being caught jerking off is insanely humiliating no matter what the situation is, which is why you’d want to be caught engaging in this behavior in the least controversial way possible.

Imagine your girlfriend comes into the house early, you don’t hear her, and she finds you jerking off. What would be easier to recover from? You laying on your back in bed jerking off looking at porn on your iPhone like 99% of normal dudes or you in the bathroom — with a chair you dragged in there — sitting buck ass naked on the edge of that chair, directly in front of the toilet watching laptop porn balanced precariously on the toilet’s top and treating your body like an amusement park?

No contest, right?

I’d advise that woman to break up with you on the spot because there’s no way this is the most creepy thing you’re into, nope, you’re untrustworthy from this point forward.

Plus, what if, as seems likely, at some point that relationship ends. She tells every girl she knows about your porn habit and before you know it her entire social network knows you as guy who jerks off into the toilet guy. That’s tough to overcome. (No pun intended).

Not to mention the fact that if you ever got unexpectedly startled — or you live in California and there was an earthquake — your laptop could fall into the toilet.

Also, how much of a mess are you creating jerking off that you can’t just use toilet paper and then flush the toilet paper? I think you are drastically overreacting here. (Furthermore, if you’re jerking off on your own clothes you are too uncleanly to date anyway. That’s just gross, abhorrent 14 year old male who just learned how to jerk off behavior).

Finally, if you really don’t want to create a mess because you’re such a clean freak, why not just do it in the shower?

Not only are you potentially a psychopath, but your logic doesn’t even add up here.

I do, however, appreciate the fact that you are attempting to be creative here and expand mankind’s jerk off horizons — especially on the 50th anniversary of the moon landing — but we don’t need a Sir Isaac Newton of jerking off. You don’t have to reinvent the GD wheel to jerk off, Steve Jobs. Mankind has been doing it just find for thousands and thousands of years, just be normal, dude. (JBND is good life advice in general, by the way).

“I’m 40 years old (same as you). Married for 17 years. My wife and I have sex on average about once a week. 

I also masturbate on average once a week and I’m 99% certain she does also.  

We all know sex even in a marriage is a complicated issue involving many factors, however instead of both masturbating once a week (without telling each other) why don’t we just have sex more often?  I feel like this is probably a common issue, dare I say normal? What say you?”

She probably enjoys masturbating because you aren’t involved.

I don’t mean that as an insult, I mean it as a way of pointing out that this way she’s allowed to create sexual pleasure for herself without anyone else involved at all. That is, she doesn’t have to worry about giving you sexual pleasure or potentially faking an orgasm to make you think she’s enjoying your weekly romps. (Or even worse, feeling stressed that she has to have an orgasm or you’re going to be upset with her, which creates additional sex stress for her, making it not very much fun at all.)

If she just masturbates by herself, it’s fast, private, feels good, and probably relieves her stress, which is why, I’d bet, she does it in the first place.

Having said that, there’s nothing wrong with asking her to let you watch her masturbate as a way to spice up your sex life.

She’ll probably say no — again, this is something she enjoys doing privately — but you’ll probably think it’s insanely hot if she says yes. And maybe she will too, which could lead to more sex for the both of you.

Either way, what’s the harm in asking?

Good luck.

“My husband and I recently got married (late 20s/early 30s). Because we met each other at work (where I still work, he is now somewhere else), we invited several of the higher-ups at work we made relationships with over the years. Two in particular were unable to make it, but said they would send gifts and have mentioned sending said gift following the wedding. We never received anything, which isn’t an issue at all. My concern is with the dang thank you notes. Do I let them continue thinking that they sent us something, with the risk that they think we’re ungrateful and didn’t send a proper thank you note? Or do I correct them and say we never received anything, with the risk of sounding like we need a gift?”

I wouldn’t say anything at all.

It’s been my experience that men (and probably lots of women too) — including me — are totally worthless when it comes to wedding gifts. If my wife didn’t buy the wedding gift then you can be certain I didn’t because I’ve never in my life logged on to anyone’s wedding gift registry and ordered anything.

No hyperbole here, I mean this honestly, I have never done it. Which, unless my wife is flawless in the wedding gift department, means we have probably missed giving wedding gifts to people.

I suspect there are many men and women like me.

That’s because every single one of us has a billion things going on every day and it’s just difficult to handle keeping up with relatively insignificant details like giving wedding gifts for weddings we didn’t even attend. Your wedding is a big deal to you, but for anyone outside of your immediate family and best friends it’s, at best, a minor inconvenience.

I also think lots of us have ambitious goals about minor details we’re going to take care of every morning and then the day hits and every day you have things you have to do, things you hope to do, and thinks you’d like to do, but probably aren’t going to do. I’d put buying wedding gifts and responding to emails in the latter categories. I have good intentions on these, but I can’t do everything and so most of the time I don’t get around to them.

For instance, I know my job isn’t necessarily typical, but there are several things that every day I absolutely have to do. As in, I can’t miss doing them because it’s my job to do live events. Here’s a typical work Tuesday for me: do three hours of morning Outkick radio, write and publish the anonymous mailbag, do a half hour of local radio, do a half hour of Outkick the Show, and finish off by doing an hour of TV on Lock It In. Leaving aside whatever prep work is required for any of these live shows or live written content, that means a typical Tuesday sees me doing five hours of live content on radio, local radio, Periscope/Facebook, and TV. Toss in a couple of hours, at least, to write the mailbag and several hours of additional prep for the five hours of live shows and I’m easily at ten hours of live work I have to do before I take care of anything else. This doesn’t even count the fact that I work from home and am trying to be a good dad, which means my kids take precedence over everything else, including time I’d otherwise spend working that they time vacuum up.

So I often neglect basic details that can be put off to another day. (This is why, by the way, my law license is always in danger of getting suspended over not getting my 15 hours of required yearly CLEs done. And I own a damn CLE company.)

Rather than remind me I didn’t do end up sending you a gift — which will honestly make me hate you — I’d advise sending a thank you note even if you didn’t get a gift over a reminder of the gift that didn’t arrive. (If I get a thank you note I just assume my wife took care of it even if we didn’t send a gift.)

So the best decision here, beyond a shadow of a doubt, is just let it go. That’s because your bosses are probably really busy and they generally wanted to send you a gift, but completely forgot about it and didn’t have the time to get it taken care of. The second best option, which is way farther back in my opinion, is to write a thank you note for a gift you didn’t receiver. The worst one, by far, is to remind your bosses they didn’t send you a gift.

“I’ve read your anonymous mailbag since it originated (best read of the week). I never thought my boring life would ever have anything I could submit, until now. I have just checked into a hotel for a work conference. Found a chair at the pool, cracked open a cold beer then I look up and what do I see? There is a lady IN THE POOL breastfeeding. Not off to the side discreetly but IN THE POOL. Fair or foul? What say you?”

This feels like a clear attempt by this lady to create an issue over your breastfeeding intolerance. I think she wants someone to complain and create a stir so she can be the breastfeeding queen bee.

Because it seems to me like she picked literally the most attention-grabbing place in the entire hotel to breastfeed. That is, she could literally be breastfeeding anywhere else in the hotel and creating less attention. She picked the most shocking place on the entire property — a crowded pool — to do it in the most readily apparent way possible.

Based on my experience as a dad, most moms at the pool or the beach who need to breastfeed and don’t want to relocate somewhere private will simply sit in the shade and drape a towel over their kid. This makes sense because it allows them to easily breastfeed without creating a huge stir and it also helps the kid end up taking a nap. Furthermore, it keeps the baby’s delicate skin from getting sunburned.

So I find it hard to believe this is intended to do anything but try and create a scene. I think this lady wants you to complain so she can brand others — potentially including the hotel if they disallow it — intolerant of mothers and breastfeeding. She wants the fight, she wants the attention, she’s intentionally provoking you and others by this behavior.

I asked my wife her thoughts on this since she’s actually breastfed three kids and she had this to say: “I think in today’s society you have to just let it go. Would I be comfortable doing that? No. But if other moms feel comfortable breastfeeding in the pool, whatever, it doesn’t really affect you at all. And if you’re worried about breast milk getting into the pool that’s highly unlikely because of how hard babies have to suck to get it out. Plus, even if it does, it’s sterile, so there isn’t any danger to the pool. Breast milk is one of the cleanest fluids on the planet and some women in third world countries without access to clean water even bathe their babies in it. He should let it go.”

(Note: I have no idea if women in third world countries actually bathe their babies in breast milk, but she claims it’s true and there’s no way I’m researching this online because I feel like it would somehow end in prison time.)

So there you go.

Okay, our youngest kid is waking up from his nap, time for more vacation here.

Hope you guys have a great Tuesday.

And, as always, you can send your anonymous mailbag questions, anonymity guaranteed, to

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.