Anonymous Mailbag

Y’all continue to deluge me with great anonymous mailbag stories. There are so many good ones that I’m constantly filing away additional questions to save for future mailbags. Charlotte McKinney, the new Kate Upton, is really proud of all your hard work. 

So here we go.  

“I’ve got a “hypothetical” (notice the quotes) situation for ya.

Say I live with a roommate. And say I leave the apartment one day; the roommate’s still there. Say I come back, maybe five minutes later, because I forgot something. I open the front door (which is still unlocked) and walk in to aforementioned roommate jacking off on the couch, with non-porn TV (like maybe SportsCenter or Friends or Seinfeld) on.

He looks at me, dick in hand, pants around his ankles, and simply says, “Sup?”

What would be the proper response for me in this situation?”

When I was in college one of my roommates walked in and caught me jerking off to Penthouse Letters. (Yeah, I had a strong literary taste in porn. Plus, it was 1999, there was no wifi). 

I was laying on his futon mattress in the corner so it wasn’t like I was sitting on a rolling chair with my legs splayed out facing the doorway. But it was still kind of evident what was going on. 

He immediately said, “Are you jerking off?”

I said, “Yes.”

And then he said, “Put your dick away, I forgot my frisbee.” (Which is maybe the greatest college line ever.)

So I can empathize with your roommate. The fact that he was able to stay totally calm while being caught jerking off is, however, a sign that he should be employed defusing bombs for a living. 

I would probably have checked to see what he was watching — specifying the show would make this story so much better. I would pray it was SportsCenter and I would immediately tell all of our guy friends — and probably some of the girls — that I caught my roommate jerking off to SportsCenter. For the next fifty years every time we walked into a bar or restaurant with SportsCenter on television I would say, “You going to be able to handle yourself with this on the TV?” 

“So, my friend from law school spent her last semester in law school visiting at an expensive private law school in Manhattan while she interned and job searched. It didn’t work out and now she lives in Nashville and is happy as a clam.

While in New York she met this guy–let’s call him Mr. Big–and started dating him. Now, while she described what they did as dating, when she told my friends and I about it, we were pretty unanimous: y’all are not dating; you are his side piece. But she persisted and they “dated” off and on for a number of years now.

Flash forward to the present day. She suddenly starts getting texts from him. Mr. Big buys her and her friend a ticket to visit him for her birthday. Then one night the texts get weird. Super weird. Like “I want to put a baby inside you” weird. Yeah.

So she’s suddenly inspired to do some digging. Well, lo and behold after some good old fashioned Googling, she finds a recent interview Mr. Big did. That article includes a video of him being interviewed. Turns out the guy is an animated talker and waiving his hands while he speaks. Including his left hand. Which has a wedding band on it.

Duh duh duh!

So, then she asks me what to do. I told her to lose his number. She wants to go to meet him for a birthday dinner and confront him about the whole thing.

What’s your/you’re advice, oh great dick-guzzling, butt-chugging, gay Muslim being, one?

p.s. she has made a binding agreement with me to do whatever you advise, so there’s a lot riding on this.”

I would cut him off without the confrontation. The guy’s clearly unstable and has been pretending to be single for years, why continue the relationship now that you’ve caught him? Also, like a lot of people reading this right now, I don’t understand how she wasn’t curious enough about him to Google him aggressively before. Doesn’t every girl have a PhD in Internet sleuthing when it comes to guys she’s dating? Much less guys she’s sleeping with. Didn’t she think it was weird that they never went to his house? Did she ever go to his job or meet his friends out? Was he not on Twitter or Facebook or Instagram? I just don’t see how a married guy could disguise the fact that he was married for YEARS without the girl adopting a degree of willful blindness here. 

My thought — she didn’t really want to know much more about him. Probably because she suspected something wasn’t quite right about their relationship all along. Now, after he flipped out and said he wanted to have a baby with her, she suddenly Googles him and finds out the truth?

I’m just not buying it.

Regardless, they already live in different cities and aren’t seeing each other regularly. Chalk this one up as a loss and move on. There’s no point in the trip and the confrontation. It can only make things worse.    

Anonymous girl writes:

“Last week you asked about how girlfriends would react in the whole puking during roommate sex scenario. While I have never had that happen to me, I have gotten relatively close. I’ve had the same best girlfriend since grade school. I think our relationship is more like ones guys have in that we are always encouraging the other to get drunk, make stupid decisions, and get laid as much as possible.

One night my girlfriend was visiting me in college. Our teams had played that day, so after a mid-day nap we went out that night. We both proceeded to get pretty hammered and naturally I began texting my long-term friend with benefits. After we got home, she passed out and started snoring on the couch in my living room. My FWB came over and we started going at it in my bedroom.

My girlfriend interrupted us not once, but twice that night. The first time, she opens the door to my room (granted the lights were off and it was pretty dark) while I was giving him head and asks me about food. I stopped, answered, she shut the door and I thought I was in the clear.

To get to the bathroom in my apartment you have to walk through the bedroom. I’m on top of my guy and I hear her stumble into my door. I paused, still in the act, and she walks into my room. She was half asleep and drunk, so she couldn’t see anything and clubbed her way through my room to the bathroom.

On her way out of the bathroom, she starts talking to me about some guy she has been seeing back home and proceeds to lay down in my bed. She didn’t realize that there was a guy in my bed, who I was on top of, and she was laying next to him. Please keep in mind, he has it up through all this.

Me: “Hey [Name]. I would love to talk but I am kind of busy right now.”
Her: “What?”
Me: “Kind of getting laid right now.”
Him: “Sup.”
Her: “God damn it [Name]. You’re such a bitch. You could have at least brought me one.”

She then proceeds to leave my room and I finish hooking up with the FWB. It should also be noted that he did petition for a threesome the rest of the night, but did not get his wish. While this isn’t as bad as the puking story, it is pretty funny that she laid in bed with us.”

Every single guy who just finished reading this wants your email address. 

Hello Clay,

“So I’ve been dating this girl for just about 5 months and things have been going great. She’s really chill, fun to hang out with, my friends like her and the sex is satisfying. All in all this girl is a solid outkick. There’s just one small problem, SHE WON’T GIVE BLOW JOBS!

I’ve literally tried everything. I’ve asked her for them, she said no. I’ve asked her why she doesn’t like them and she just says she thinks it’s weird. I’ve gone down on her and she still doesn’t return the favor. I’ve even stooped to the level of “accidentally” putting my penis in the area of her mouth. I just really want a blow job. My ex-girlfriend was the master of blow jobs and every time I want one I think about how awesome her’s were. I don’t know how much longer I can go without the sweet gift of blow jobs. It doesn’t help that my roommate constantly brags about how awesome his girlfriend’s blow jobs are.

Please use your master women skills to help me get her to give me head. It would essentially make this relationship perfect.

Thank you, you big gay muslim. 

Honestly, it sounds like your girlfriend just thinks she’s already married to you. 

Which reminds me of the joke that three different Southern dads — not the fathers of the bride — have told me at weddings. “Why does the bride smile when she walks down the aisle?

Because she’s given her last blow job.”

This is the best Southern dad joke ever. I can’t wait to start breaking this one out in about twenty years. 

The second best Southern dad joke, by the way, is going to take a piss off the side of a boat and saying, “Damn, water’s cold today.”

Gets me every time. 

Anyway, this may sound ridiculous, but you have a real decision to make here — do you like your girlfriend or blow jobs more?

I’m serious. No girl or guy is perfect. There’s always something that you would change about your partner. Hell, most women marry guys not even liking us that much, they’re just convinced they can change us into something they do like. Honestly, you’ve done the mature thing here and directly asked her why she won’t give you blow jobs. She says she thinks it’s weird. So does that mean she thinks 98% of the women in America over the age of twenty are weird too? I don’t think anyone in America actually likes giving blow jobs. Sure, some people pretend to like it, but they’re lying.

Take your girlfriend to see “Fifty Shades of Grey,” this weekend. That’s some wacky, deviant sex for a mass audience. Blow jobs are tame compared to that movie. Maybe she’s into sex swings or bondage. Evidently there are tons of women out there who want to be whipped and tied up with chains. Who knew? If she still refuses to perform blow jobs, and it’s a deal breaker for you, you’ll have to break up with her.

I’ve never heard of someone being broken up with over blow jobs, but I’m sure it happens. I can’t imagine that her girlfriends will have that much sympathy for her — seeing as how they probably give blow jobs too — but we all have our needs. This might be yours.

The really funny part of this is will be if she decides she’s willing to do blow jobs to keep you. That’s true love. 

“My wife would kill me for asking this, but I have to ask anyways. We are getting ready to try for a kid and we have agreed that if we are lucky enough to have one, it will be only one. There will be no second child. I am the last shot at having our family name live on with a boy at this point. I know that it is up to the male as to what the sex of the baby is and there are urban legends on how to accomplish this, but are there any proven theories that increase the likelihood of having a boy while conceiving? Don’t get me wrong, all I want is a healthy and happy baby, but having the family name live on would be a good thing too.”

There are no proven methods to increase your likelihood of having a boy.

So when you have a girl and your family name dies, it will be all your fault.  

“Since we’ve been married, my wife and I have had separate bathrooms. It works out great for us because we only have one kid right now and my wife likes to clean her bathroom more often than I clean mine. We also have a dog. Our dog will sometimes go rummaging through the garbage can in my bathroom because it’s accessible and that’s what dogs do. The problem with this is, the garbage can in my bathroom is where the used condoms go. It turns out, yep, my dog got a taste for used condoms. We know this because we noticed on multiple occasions the used condoms in her poop. This is something my wife and I haven’t been able to tell anyone because no one wants to know that about us and our dog. We have since taken measures so my garbage can isn’t so accessible. This got me thinking, what other items have other people’s dogs eaten/chewed up that they can’t tell other people about? This would be a great subtopic on the Anonymous Mailbag.”

What a sick, perverted fuck of a dog you have. He eats your old condoms? Then he’s going to lick all over your faces. 

Gross. 

There have to be some great dog stories out there though. 

“When I was a junior in high school I had a pretty serious girlfriend who I am actually still dating. One day we thought it would be fun to “sext”. Now, as a high school junior at a Christian high school you can imagine how excited I must have been. We went on and on for about an hour or 2 uttering phrases like, “I want you to sit on my face” or “I want to milk you like a cow” (that one was for me I guess. We didn’t really know what to say). Well, this pure joy turned into horror once my mother got a hold of my cell phone and started going through my text messages. One by one she read, I’m assuming her gagging along the way. Well, once I realized I couldn’t find my phone I came downstairs to the horror of my mom and dad looking at it. They sat me down and MADE ME READ THE MESSAGES OUT LOUD TO BOTH OF THEM. My mom started to cry and my dad started to laugh. I was in our living room reading out dirty messages to my parents. I never left my cell phone out again.”

I don’t even know your mom and I’m laughing thinking about her crying while reading sexting messages from her son.

For some reason this reminds me of a kid I knew in seventh or eighth grade who was really messed up because his mom, who was really religious, told him God would cry if he masturbated. I can’t think of a meaner thing for a mom to tell her 13 year old son. Every time he got an erection he thought he was making God cry.

I’d love to know what that guy does now.

…

Outkick’s mailbag is 100% anonymous. You can email us anything at clay.travis@gmail.com