Anonymous Mailbag

Charlotte McKinney, Kliff Kingsbury

It’s time for the most popular weekly article on the Internet — anonymous mailbag Tuesday. 

As always, send your emails, anonymity guaranteed, to clay.travis@gmail.com

Here we go:

“Greetings oh wise one. I am in desperate need of your help here. Some quick background: I am a 41 year old male who greatly outkicked his coverage and am married to a very beautiful 31 year old. We have 2 young boys and have maintained a pretty solid sex life and have jokingly, for the most part, talked about a threesome one day. With another female of course.

About 6 months ago, while planning our annual pilgrimage to Vegas, I half heartedly suggested that this trip to Vegas would be a perfect opportunity to have this fantasy realized. Much to my surprise, she was interested. Very interested. She went as far as checking the Vegas backpage ads for female “companionship” and picked a few that she would call up when we get there. I was in shock. This was going to happen and we have the same great tastes in women.

After a couple of weeks of continuing to plan this one night (or hour, 30 minutes, whatever) of ecstacy, the talk has died down. Her interest has gone from definitely to “let’s see what the alcohol says” to probably not.

Clay, the trip is in less than 2 weeks and I’m in full panic mode! I’m not pushing the issue because I do enjoy my martial bliss, but I want so badly for this to happen. I feel my time in life is running out for this type of thing and think it’s basically now or never. How can I possibly get her back on board?”

Alcohol in Vegas. 

If she initially liked the idea — and even did research on the girls she wanted to pick — then when the two of you get to Vegas my bet is she’ll loosen back up and her inhibitions may melt away. 

But I wouldn’t bring it up again until you’ve been drinking in Vegas.

My bet is that at some point as she planned the event the spontaneity and excitement of a decision like this, which is a major part of the fantasy, got bogged down by the complexities of staging the actual fantasy and her contemplation about what the morning after the fantasy might be like. What makes fantasies often fun is the fact that they aren’t rooted in reality. Once the reality sets in the fantasy and excitement can sometimes dissipate.

Wait for the trip to happen and go drinking. Then bring it up again. You already know this, but women decide everything in sexual relationships. So she’ll either be into it or not. I don’t think there’s much you can do to make it happen. It’s on her.

Good luck.  

Also, as an aside, I feel like this is probably the hottest fantasy that an average married woman would consider. Go to Vegas and pay a stranger to hook up with you and your husband. You never have to see the girl again and it’s hot as hell. And every single straight guy on earth love this idea.

Yes, even your husband, who you’re asking about this right now and he’s pretending he doesn’t really like the idea because he thinks you’re trying to trap him.     

“My fiancé and I live across the country from her family right now. The understanding has always been that once we got closer to marriage we would move back across the country to be near her family (my parents are divorced and not in the picture). All good to this point – but here’s the catch. She wants to live with her parents at their massive house for up to a year when we move back (both pre and post marriage) to save money when we move back, and also give us time to find “the right house.” Her parents house isnt extravagant by any means, but it IS a big place and we would have the upstairs to ourselves.

My buddies are divided into two camps: the ones who say to be a man and sack up and rent or buy right away, and those who think we should definitely do it because they are freeloading pieces of shit. First off, her parents are great and are almost retired, so they’re usually gone on vacation. Second, she and I are late twenties and both work good jobs (and will when we move back). Finally, we are moving to [large metro area in the NE], where a place in a good part of town costs at a minimum 2,000 a month, so we could save substantial cash.

What say ye, gay muslim? Should I bite the bullet and move in with her folks for a bit? Or is my pride worth $24k (minimum amount we would pay for rent?)”

I’m not going to immediately dismiss this as absurd, but I think this ultimately comes down to what you and your fiancee’s relationship is like with your in-laws. Do you really get along well with them? Because a year is a long time to essentially have roommates.

Also, how nice is the place — the nicer it is the easier the call is because if the house is huge you can just convince yourself that you live on your own — and do you want to ever have friends over? If you live at someone else’s house you can’t really have people over to hang out with you, that’s pretty weird.  

And here’s my final question — how much nicer of a place are you really going to buy with the extra $24k? If both of you have good jobs, you should have no problem getting a mortgage. Right now mortgage interest rates are insanely low and you’ll be financing the vast majority of your home. So what we’re really talking about here is the downpayment. 

Do you have no savings at all otherwise? If so, then you need to save to buy a place and living with the in-laws makes sense. But if you already know what your budget is based on your dual incomes — let’s say you can spend up to $350k — and already have enough for a downpayment on a home then all you’re really doing is saving to have a smaller mortgage. And thirty year mortgages last so long that there isn’t much of a difference in your monthly playment.  

For instance, let’s say you have $50k saved to buy a place now and you add $25k to the downpayment after living at your in-law’s for a year. That’s great, but it doesn’t change your mortgage payment that much. Your mortgage on a thirty year when you borrow $300k is $1400 a month. Your mortgage when you borrow $275k is $1300 a month. Your life is pretty much the same either way. (Especially when you consider the mortgage interest deduction which means you end up saving even less.)

So, to answer your question, I think this only makes sense financially if you don’t have the money to put a downpayment on a place already and have to save up. If you do have the money for a downpayment then go ahead and buy a place and live on your own. Not entirely for your own pride — although that’s part of it — but also because the financial benefit isn’t that substantial.   

“I’ve been married 5 yrs to a woman I adore who’s wonderful, 5′-5”, 105-110 lbs, and with a personality that would trump if she wasn’t physically amazing. That said, we’ve had, well, no goalie blocking the net so to speak, our entire marriage.  We got engaged 5 weeks after meeting, and married 4 months later. We have enjoyed the time to splurge our earnings on ourselves, but clocks are ticking and we want kids. Problem is, we’ve tried the “natural family planning” routine for about 6 months or so, but no go.

All that said, is making babies that difficult, and where would you point those looking to bring kids into this silly PC Bromini world? We both love our cocktails after work and an occasional tobacco break.  I feel like part of it is a mix between having a 30-yr old’s sperm that probably swims a bit slower, and part we both like to have out fun and enjoy the fruits of our labor. Is there an answer is taking, say, 3-6 months of no alcohol/tobacco to potentially make a lil guy/girl?  Or do we head to a fertility clinic where I’m surely forced into the awkward room where I have to deposit into a cup?  

You’ve made 3 babies, and make wicked sense, so curious what you suggest.”

First, I’m not an expert on fertility so you should actually consult someone who is an expert on fertility, but most girls who get pregnant drink alcohol long before they know they’re pregnant. (In fact, if alcohol killed babies like 90% of us would never be born.) We had no issues getting pregnant — probably because unlike with you my massive penis penetrated far enough into her to ensure pregnancy — but I know lots of couples do have pregnancy issues. 

If you’ve only been trying for six months, I wouldn’t get checked yet, especially if your wife came off birth control just before she pulled the goalie. But once you hit a year, I’d think about doing it for sure. 

We had a series on awkward fertility clinic stories on the anoymous mailbag a while back, but the most important thing for you to know is that this is the only time in your life that your wife — and other women — will be encouraging you to jerk off. 

So at least you’ve got that going for you. 

“I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.”

If a couple chose to have “Showgirls” sex in a public pool with balconies overhanging the pool they wanted you to watch. 

You had no obligation to keep quiet. Honestly, I think jerking off on your porch while you watch them is even in play here. Especially if the girl is hot. They’re begging for the attention.   

It’s not like if your chair squeaked that they were going to suddenly think, “Wait, people might see us if we have public sex! in a public pool inside an apartment complex!”

“I’m 38 and recently divorced after 15 years of marriage and 2 kids. Dated several women, and of course, slept with several women before meeting one that I really enjoyed being with and spending time with. She’s younger than me by about 5 years and has two kids… And is very very attractive, I’m dating “up” without a doubt.

After a little time together, I discovered that this woman truly enjoys and wants to have more sex than me! Thank God! I had no idea such a woman existed.

However, this leads to the story…

I’m a rather tall, sizeable man. And I’m very proportional in dick size. No I don’t have some huge dick that you might see on porn, but I’ve always gotten good reviews and compliments on my size and feel confident that I am above average (been with over 25 women, not just a few, so I believe that is enough opinions to justify an above average to large dick size rating). Now, back to current girlfriend. I sometimes have to travel for work and may be gone for over a week and that is to long for her to go without the “D” as she puts it.

So she ordered a dildo for these times. As soon as she sent me a screenshot I was like WTF? She orders this 9″ (length is one thing but the damn girth on this thing) dildo that would make a grown horse jealous! She gets it and I have never felt so small in my life as when I saw it! She says she’s returning it because it’s too big… But you guessed it, it hasn’t been returned and ain’t in the package anymore. Said she tried it and it’s too big… But now I kinda want to see her try to ride this thing.

Now this is the problem… How will I feel if I watch her with this thing? What if she enjoys it a lot? The damn girth on this thing is crazy! I’m dating up so will this give me a complex? I’m already feeling like I’m probably not the biggest she’s ever had, which is unusual for me. So what do I do? Get her to pull it out one day, ask her to throw it away, or do nothing?

Hoping someone with a small dick and subpar looks like yourself can give some helpful advice.”

Were you present when your two children were born? Did you watch the delivery process? If so, it should have cured all your fantasies of ever fully satisfying a woman. A baby came out of her vagina. Get over your dick size.

You know what’s more important than a huge dick? Confidence. (And money). Every woman reading this right now would rather marry a millionaire with a four inch dick than a guy who makes $30k a year with a ten inch dick.

So tell her to break it out and enjoy the show. (Then cry quietly after she falls asleep as you think about the massive penises of her prior boyfriends). 

“I am a die hard Cavs fan and my girlfriend has adopted Golden State/Steph Curry as her favorite team/player cause she doesn’t want me to be happy.

Since these teams are both in the NBA Finals, we have decided to make a bet on the series.

If the Cavs win, I finally get to have anal sex with her. This would also be my first time ever having anal sex with a chick.

My girlfriend will only accept the bet if I agree to let her use a strap-on on me if the Warriors win.

Is this bet too risky or is the juice worth the squeeze?”

“This would also be my first time ever having anal sex with a chick.”

So you’re just out there banging dudes all the time, huh?

Proofread, bro. 

Anyway, I hope you didn’t make this bet. It was awful to begin with since the Warriors were a prohibitive favorite entering the series and you’re risking much more than her. Now that the Cavs are down 2-0 there’s like a 99% chance — unless the Cavs win four out of the next five games over a team that is 86-15 on the year — that your girlfriend is going to sodomize you. 

On the positive side, at least you’ll be ready for prison. 

Send your anonymous mailbag questions to clay.travis@gmail.com

I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.
I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.
I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.
I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.
I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.
I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.
I just got home from a long day of work and decided to sit on my balcony with a couple beers at my apartment complex. My balcony is on the 3rd floor right next to the pool. At first everything is great, I am just relaxing drinking a beer. About ten minutes in a couple wades into the pool for a little nighttime swim, or so I think. I crack open beer number two and to my surprise I hear sounds of some pretty extreme sexing happening. When I looked down at the pool it was like I was watching that scene from Showgirls where A.C Slater’s girlfriend was riding that dude from Twin Peaks. The water was splashing so hard I thought I was watching an amusement park ride. The only problem was that I was about to crap myself. Instead of getting up from my squeaky furniture and fearing that I might ruin this couples fun, I stayed in my chair as silent as I could be until they finished their happy time (which was about 10-15 minutes longer than I was anticipating). The second they were done I got up and ran to the bathroom. My question is, did I do the right thing by not cock blocking a random couples fun or should I have immediately went to the bathroom? Thanks, love your work.

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.