Things I’ve Learned Sleeping With Older Men

Older men remained an unexplored territory until my mid twenties. Dating in 2018 can be challenging especially in New York City. Nowadays Tinder, Bumble, and Hinge are the modern dater’s new go-to tool. These applications have marginalized sex and its casualties. It’s developed into a normalized hookup culture. Single Manhattanites have turned the dating scene into a numbers game.

Young unattached women and men have generated a sexual revolution where relationships are clichés, dating is outdated, and the idea of commitment is comical. One female twentysomething* explains the phenomenon thus: “It’s that there’s this weird gray area. People still want to be in relationships, but they don’t want to be settling.” I concur. Yet, it is socially acceptable for both men and women to indulge in casual sex on a weekly basis with various partners.

So, why is having sex with a man twice your age still considered taboo ?

I genuinely find this bizarre, and not only because I come from Europe, where having older partners has been acceptable for centuries. Of course, sex is a different experience with every partner you have it with. As I grew older, I had a variety of sexual experiences, and I’ve learned one thing to be true in the last few months which I originally thought was a myth: Sex with an older man is more enjoyable than with a man my own age.

I did not make it my mission to share this story with you. It happened by chance. My very first encounter was with a man twice my age, and I was very rational after it happened: older men haven’t grown up in an era of porn where aggressive making out is standard; they kiss and touch you like men you see in classic movies.

My first romantic encounter with an older man was electric. He was refined, intelligent, cultured, and intuitive— a true man. He was everything that boys my age weren’t. Initially, I thought he was the only one to have these impressive traits. However, I quickly realized he wasn’t the only one. A few months later, I met another man unexpectedly at a bar on the Upper West Side.

And, much to my amazement, he was just as refined, cultured, and intelligent. Spending time with them was exhilarating. I’ve never had much confidence and I always second-guessed myself. So needless to say when they took me to bed, at first I was nervous and apprehensive. However, as soon as I got naked they found a way to make me feel relaxed and comfortable.

And so, I am here to officially announce that the most unforgettable, mind-blowing sex I’ve ever had was with men twenty to thirty years older than my vintage. As a matter of fact, the first time I ever had an orgasm during sex was with a man twice my age, and it kept happening with most older chaps after that.

This did not happen because I was choosing men who were gifted at knockin’ my socks off, but rather because they were simply more experienced and knew more about the female body. I can only speak from my past experiences; this might not be true for every older man, and I cannot affirm that this applies for older women. It has simply been the case for me.

Most of my friends had the same frowning expression on their faces when they found out I was dating men twenty to thirty years older than me. A friend once said with one eyebrow raised, “Older men kiss funny, have saggy balls, and wrinkly arses, what is there to like about that ?”

I laughed. And answered:

Honey, older men haven’t grown up in an era of porn where aggressive making out is common, they kiss, and touch you like gentlemen you see in movies. Older men are much more passionate, giving, and obsessed with making you come first.

Most of them are confident in their performance and they want to please you — the sex is steamy and mind-friggin-blowing, whereas men, or should I say boys in their mid twenties are still on the search for the elusive clitoris.

Thanks to these thrilling sexual love affairs, I’ve learned many things about myself and life in general, which is why I wanted to share them with you today. Here are a few reasons why having sex with older men will turn your frown upside-down.

1. They have a vested interest in the female body

Admit it! Guys in their mid twenties and early thirties have no idea what the f**k they are doing when it comes to the female body. It usually goes like “Hey, hi nice to meet you, let me just poke around down here — uh, hmm, err — is it time for sex yet?”

They are clueless about how the female body responds to different touches and stimulation. Guys in their mid twenties aren’t confident in their own skin, hence their focus tends to shift to “how many gold medals they’ve won in the Olympian “dick-a-thon”.Men with more experience under their belt know what works and what doesn’t.

They don’t sit there and ask, “What happens if I press this button?” Yes, younger guys may be more adventurous and acrobatic, however older men know how to use their sexual strength to give you phenomenal sex. Their technique is different, they understand that there is more to the female body than her boobs and clitoris. All of my sexual love affairs with these old chaps were unique.

2. You’re comfortable with them

Older and well established silver foxes have had the opportunity in their life to date the swimsuit models and bombshell actresses — been there, done that. They are not so attached to physical traits as younger guys are. They embrace your flaws because they know there is more to it. Older men are so secure that you don’t worry about those four extra pounds that you haven’t been able to lose.

They are in awe at every inch of you.This easiness makes it an incredible experience sexually. Because all of the men I’ve been with have been so secure with themselves, I felt very settled in myself around them. I was aroused by a simple stare, a caress in between my thighs or even a soft kiss. My pulse and breathing would quicken and my skin would become flushed.

3. They understand the importance of foreplay

Out of my 26 years on this fine planet, I have spent 25 of them orgasm-less having average sex with below average partners that cared very little for my fresh, peach-looking vagina. Most of my partners were terrible at oral sex but required me to be better than that girl they saw on porn tube channels. Beginners tend to skip the foreplay, the sensitive touching and licking.

I know, I was almost married to a guy like that. My first real foreplay was with a woman, and I climaxed like never before. It was amazing, my entire body shivered as her tongue caressed my inner thighs. With her, I just let myself go and accepted the attraction and trusted the feelings I had, and we had life-changing sex as a result of that.

Plus, we were both straight or simply bi-curious, but there we were, having awesome sex, which made it even hotter. With experience, men finally understand that it takes a women extra time to get to that level of arousal which will ultimately lead her to orgasm. Consequently, all of their attention is focused on pleasing you — AKA, the way it should be!

4. Constructive sexual feedback

Again, because an older man has probably been married before or at least been in a long term relationship, he knows how to communicate in a constructive way. He expresses himself in a way that makes him a better partner. A good communicator goes hand in hand with a good listener.

You may be surprised by how an older man is a way better listener than any young guy that you’ve dated. In this case, he can handle your honesty and isn’t afraid of the idea of you giving him constructive sexual feedback and — hot diggity dog! — he is definitely not afraid of your sex toy!

Can you believe it? Some younger men get frustrated when you whisper, “Please, don’t do that,” or “Do you wanna try my vibrator?” An older man wants to hear what makes you climax and he won’t get his feathers ruffled if he’s not doing something the way you want him to. An older man gets aroused when you take the lead.

5. They’re romantic in every sense of the word

Ladies, Romance with a capital “R” is not dead. Older men understand that it’s what happens before and also after that builds up desirability and creates the magic of sex. It’s not all about sexual intercourse — it’s about the small gestures and details. Dates with older men are first class every time.

For instance, I have been seeing this man on and off for a few months, and each time I feel extremely excited. Whether he’s flying me out to some exotic location or taking me to a lavish dinner in a beautiful dress and killer designer heels. I am aware that this is not an actual relationship but rather something mutually beneficial.

As soon as I step out of the elevator on the 48th floor overseeing Central Park, he greets me with my favorite tequila on the rocks and wraps his arms around me. He is enamoured with every inch of me and it feels amazing.

These men have set the bar very high for me. The romance and conversations are stimulating, deep, and sometimes erotic. This isn’t something most guys my age can achieve. These sexual love affairs have changed my perception of dating.

Suddenly, bumble coffee dates didn’t seem as electrifying as talking about business ventures in front of a fireplace with a glass of 2014 Gevrey Chambertin. This experience has taught me how to feel sexy, confident, and overall wanted. All of these men have created a world of exceptions, and consequently I learned how a man should always make me feel.

So ladies, give the older man a try. A date. Dinner. A sexual encounter. I can almost guarantee that he will rock your world. Set aside the younger boys, and their reindeer games. Try a real man, ladies… we all know that’s not easy to find.

Endless Feels Amateur writer, essayist and poet of love, avid dreamer, and lunatic with a seething brain Endless Feels

Endless Feels

Endless FeelsAmateur writer, essayist and poet of love, avid dreamer, and lunatic with a seething brain.

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