How big is his junk? How long can he last in bed? Is he a good kisser? How many times can he make my toes curl? Can he make my toes fall off completely? 

Who needs toes as long as the sex is effing amazing? Am I right ladies? As part of the last post of the 10 challenges of loving executive men series I’m going to share some sex tips with you that I promise you won’t find anywhere else.
 
But let me start by being real, honest and downright human with you for a sec. Have you ever felt pressure to look a certain way? C’mon, don’t lie. If you have an Instagram account, the answer to that question is a hard yes. Have you ever felt pressure to perform sexually? With all the rap lyrics about “b*tch needs to ride good dick” and female porn stars that men expose themselves to as willingly as Trump exposes America to a nuclear attack, how could you not feel pressure to perform sexually?

I’m going to let you in on a secret that you will absolutely not hear anywhere else. 

Ready?
 
Men feel just as much pressure to perform sexually as we do.
 
There are a million articles out there that offer sex tips to him about what he should do to make his baby maker bigger or last longer. The one thing none of them talk about is what he should do to make sure he’s on the same page as you. There are a number of things to consider before getting to the part where you rip off each other’s clothes, like what both your expectations and boundaries are or how experienced each of you is in the art of (insert your sexual flavour). Unfortunately, mainstream media has taught men, executives included, that… 
 
a) he needs to be better than the rest at sex, because for men, obviously everything is a competition;
b) it’s okay to “figure it out” with as many women as it takes (this is how fuck boys are made by the way and executives come in that variety as well) and;
c) if he can’t figure it out then that will become the reputation he will wear literally forever.
 
We allow men to form and live by the above attitudes. Then we work hard to fight things like rape culture and sexual abuse in Hollywood. It doesn’t make any sense because it’s all so counterintuitive.  

I want to change the way we talk about sex.

I want to change the way men perceive expectations of themselves when it comes to sex. And it starts with women like you and me, women who love ambitious men who eventually end up having a platform from which to influence change. You know that saying, there is a strong woman behind every successful man? Well, this is how it’s done. With you and me right here.

I want to start by offering some food for thought:

Hockey players and basketball players start practicing their craft at the same age that an accountant first learns how to do math. People who are amazing at certain skills have yeaaarrrssss of practice. Why do we hold men to a different standard when it comes to sex? Why do we expect them to be automagically perfect at sex?
 
Sex is about so much more than the physical exchange that takes place between two people. Where a person comes from, what they’ve experienced, and how they perceive the world all shape how they have and enjoy sex. I’ve had so many conversations with executive men about their sexual insecurities. This includes friends and exes. You might be wondering how I got any man – executives no less – to be vulnerable about physical intimacy. It takes coming to the table with no judgements, open ears and an open heart. Being compassionate and appreciating that sex can be a completely foreign and scary thing for someone who has limited experience can go a long way. It takes having the conversations our parents never had with us because their parents didn’t have them with them either.

Before I share my 5 sex tips with you, I need to give you a bit of context. I’m going to tell you two stories, one about Chad and one about Tony. 

Chad is a senior executive at a very large company. His resume looks great, as it should, because Chad was a quiet nerd growing up. His extracurricular activities as a kid involved his parents taking him to the library. He’d bring home a stack of books every weekend and reading these was on top of doing homework and getting the straight A’s he was expected to earn. When he was in high school, he’d help his immigrant parents keep their business finances in order. Most 16 year olds were experimenting with drugs and physical intimacy, but Chad was figuring out how his parents could pay the least amount of taxes. 
 
Chad is also an only child. Being a social butterfly or a team player was never Chad’s forte, as I’m sure you can put together. Getting into corporate management means being a team player, so imagine how tough it must’ve been for him to earn all those promotions. Chad has busted his ass to earn his success. Because all of his focus went towards mastering not being socially awkward in the workplace, Chad didn’t have time for women. Now that he wants to make time for women, he worries that when he finds one, he won’t know how to what to do her. I don’t blame him.

Tony, on the other hand, also from an immigrant family, has siblings and was a bit of a badass growing up.

Always getting into trouble, experimenting with drugs, getting arrested, acting like he’s the shit. You know the deal. Tony is also an executive. No, he’s not a mob boss. He’s one of those guys who turned his life around at just the right moment. Today, Tony runs a national professional services firm. 
 
The interesting thing about Tony is that he used his tough guy persona to avoid girls growing up. He was the guy who’d be an asshole to girls in high school, not just to seem attractive, but to literally keep them as far away as possible. Then in university, he fooled around with as many girls as he could for bragging rights, but never gave up his V card for fear of becoming a teenage parent.
 
One of the biggest issues is that guys don’t have healthy conversations about their feelings for girls growing up or how they should act on them. They had no positive examples to follow when their teenage hormones were raging and when their sexual intentions needed to be appropriately categorized as healthy vs unhealthy ones. The only examples they had were Disney, Hollywood/Bollywood and porn.

Now tell me, how healthy is a man’s sexual perception going to be if his sexual diet consists of Disney as a child, mixed with Hollywood/Bollywood’s interpretation of physical intimacy and porn as a young adult? 

 Chad is a friend and Tony is an ex of mine. Tony was a virgin the first time we were intimate, which happened about 6 months into our relationship. I didn’t learn this until a year after that first time. He was 29 at the time. 29 is late, by North American standards, for a man to lose his virginity. He said that when he was in university, he came close to going all the way with a girl. He really liked her, but their future together was uncertain and he wanted to wait for the right person because he wanted his first time to be meaningful. Had he ever told his friends this, I’m sure they would’ve ridiculed him. 
 
He explained that by the time he was in his senior year in university, he didn’t have time for girls because his course load was so heavy. He was also working part-time to pay tuition. Then he got busy with launching his career and before he knew it, he was 29 and still a virgin. It made him apprehensive about dating and that’s why he hadn’t been in a serious long-term relationship before. Unfortunately, he shared this with me well after he had led me to believe that he was very experienced in the sexy time department. Probably because like his friends, he initially thought I’d make fun of him. 

Ladies, you’d be surprised at how many successful men there are who have limited sexual experience.

Don’t get me wrong, there are plenty of fuck boy executives out there too who can’t have enough side chicks. But there are also guys like Tony who feel like they have to bring a certain amount of sexual experience to the table in order to be desirable. Sweet guys like Chad feel the pressure too. 
 
So, here are 5 sex tips that will be sure to make sex a comfortable and pleasurable experience for you and him instead of making it a mediocre experience for you and a traumatizing one for him:

1. Share your sexual experience without bragging or being intimidating.

We women are often expected to downplay our sexual experience out of fear of being called a slut. My advice is don’t downplay shit. Own your truth, girl! And besides that, being honest is the only way to set the bar where it belongs. Just don’t do it in a sexually suggestive manner. You know, where you bat your fake eyelashes and bite your matte red lips. Yeah, get rid of that until you know he’s comfortable with meeting your sexual expectations because he’ll find that intimidating. The goal here is not to turn him on. It’s to ensure he doesn’t run away thinking he won’t be able to deliver the goods. Have a nice clear heart to heart conversation with him.

2. Don’t expect him to meet or beat expectations.

I mean of course you want him to totally beat the hell out of your expectations over and over and over again 5 times a day. Who doesn’t? But again, if you start even hinting at having expectations, he will shut down or implode. Think of Sheldon from the Big Bang Theory every time Amy gets even slightly hot and bothered. Or think of Richard Hendricks from Silicon Valley in season 4, episode 6, where he has the most awkward sex to ever make its’ way into scripted television. I mean, seriously, it took 4 whole entire seasons. But, it’s because that’s how it is in real life. You’ll have to tell your man, using very direct words, that you have no expectations and you’ll need to really sell it. Hold his hand, comfort him, make him buy it. And then get yourself on board with the fact that he will not meet or beat your sexual expectations. There, there, big girls don’t cry. This is temporary.

3. Learn about his sexual experience.

Ask him questions about his sexual experience without interrogating him. This means that your questions should feel like he’s having a conversation. That means you’ll have to carefully craft your questions so that they build on each other. For example, start him off easy by asking him how many women he’s dated. Then ask him how many of those were long term relationships. If he’s smart, and most executives are as far as I’m told, he’ll ask you what your definition of “long term” is. See? Conversation. If his answer is a number other than zero, it’s safe to ask how far he ventured sexually in that long-term relationship. Preface the question with “you don’t have to answer that if you don’t feel comfortable”. He might break a sweat or squirm before answering honestly. If he is honest, then he gets the benefit of you not having any expectations. If he’s anything but honest, then girl, throw tip number 2 out the damn window.

4. Ask him where it hurts.

Not literally, but you know how a doctor asks you to tell her where it hurts? Same deal. Ask him what he’s not comfortable with sexually, what he doesn’t think he’s good at, where he thinks he could use a bit more practice and what he’d like to try. Even go as far as asking him if he has any apprehensions about sex if he’s never had it before. You’re not a mind reader. You won’t know if you don’t ask him and getting this information is vital to successfully executing tip number 5. Remember, always be genuine and never force him to give you information that he doesn’t feel comfortable sharing. If you do, he’ll lie and you don’t want that.

5. Help him grow.

He may not meet or beat your expectations right of the bat. Even very few experienced men do. But with open lines of communication about both of your sexual expectations, he will quickly figure it out. It also doesn’t hurt to show him and tell him exactly what you want him to do for you. Books are a good place to start. This one is good to start with, and so is this one, and this one. With books, you want to make sure you read them along with him or before he does so that you can highlight exactly what in the book excites you vs what doesn’t work for you. Another thing you can try doing is send him “how-to” videos in a sext and say something like “Wanna add a new skill to your resume? I vote for this one”. The other obvious option is to study porn together. I will add some fine print here and caution that normal people are often not capable of having porn star sex, whether you’re a man or woman. Porn stars are athletes. Literally. The flexibility, stamina and all those super uncomfortable positions…don’t try it at home kids.
 
The best part about men who are sexually inexperienced is that you get to mold them to your sexual preferences. The downside is that it takes patience, time, effort and maybe a few fireworks that never quite explode. Play up the positives. Comfort him when it comes to the negatives and I promise you, you’ll build an unbreakable bond.
 
Let me know how it goes….but spare me the details, kay?
 
xo
 
-M

P.S. I love you and also…

When I was doing research to suggest some helpful books for you to read as part of this post, I entered the search term “VIRGIN MAN” in Amazon. What came up only validated everything I’ve said in this article. An endless list of erotic fiction where virgin women are glamourized sat before me. Page 2, page 3, page 4….page 15. Eventually I got tired looking for anything that even touched on the topic of male virginity because nothing showed up. I hope it was just that I didn’t look hard enough and we as a society don’t literally have a problem where we shame virgin men into becoming undercover or real fuck boys.

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