Sleeping With A Man 20 Years Older Than Me – Here’s Exactly What To Expect

10 key points you should be aware of before giving him the green light

Have you found someone older to whom you are attracted? I can relate; older guys are sexy if you ask me. There is something with that knowing twinkle in their eyes. You might be wondering if you should jump into the deep end and sleep with him? In this article, I tell you about sleeping with a man 20 years older than you, so you know what to expect. This way, you can make an informed decision.

My story

I have slept with my fair share of older men. I like the combination between experience and playfulness. I’m a sucker for that rugged charm.

There are a lot of upsides to sleeping with an older man. Oftentimes they are generous and interesting. They have depths to their personality and they also show a lot of gratitude when you grace their bedsheets.  

Not all older men are the same

I will make a lot of generalizations in this list. The truth is, of course, that all older men are different.

Some of them have lots of experience when it comes to sex and what it takes to satisfy a woman. But you can also be older and inexperienced.

They all have their unique baggage

Some older men have a long marriage behind them, whilst others have been single for most of their lives. There are older men who are diehard players and there are older men who are practically virgins.

Unless you try, you can never know exactly which version you will get. But let’s jump in and find out everything you can expect when you are thinking of sleeping with a man 20 years older than you.

1. Older men are more confident

Older me are not plagued by the same insecurities as younger guys. You would think that they would feel a bit insecure and self-conscious, sleeping with someone 20 years younger. But that has not been my experience.

On the contrary, older men know who they are and what they want. This knowledge gives them a quiet confidence that’s very alluring.

They value your presence and the youthful charm you bring to the interaction.

They are consistent

Most older guys will not play games or act out on their insecurities. They know a woman’s attention is something valuable and not something they can take for granted. But they also know that life goes on if they don’t get you.

This confidence will come across in how they approach sex. I have found older men to be confident around their bodies, my body and a lot of various sexual activities.

Sleeping with a man 20 years older than you will also give your confidence a boost since you see how naturally he approaches sex.

2. Older men are more open to your suggestions

Young guys sometimes take your suggestions as criticism of their performance. They can be surprisingly narrow-minded in how they express their sexuality.

They have been around when it comes to making a woman fulfilled

Most older men have enough experience to know that every woman is unique and that they have to consider her likes and dislikes to be able to satisfy her. I have found older men to welcome any kind of input I have.

Do take the lead from time to time

Surprisingly enough, older men are eager to learn when it comes to new bedroom skills. So don’t be afraid to throw out instructions. You can learn an old dog new tricks

To get some ideas on what to order from this very mature menu, check out our article 13 things guys like in bed but won’t ask for.

3. Older men like to take things slower

A lot of young guys have simply watched too much porn.

They think a quick foreplay and a long forceful penetration are the main features of amazing sex.

Every older guy who has been in a couple of long-term relationships knows this is far from the truth. He will have had plenty of women telling him to slow things down. He will have taken notes and over the years, his skills have matured just like a fine wine.

I would say this is one of the biggest advantages of sleeping with a man 20 years older than you.

Expect an older man to take his time

Most older guys work with a slow build-up. They are usually good at dishing out oral sex, and they have a couple of tricks up their sleeve.

Every older man I have slept with has surprised me with a couple of things I hadn’t experienced before. An older man is also more likely to want to savor every second he spends with your naked body.  

4. Older men are more interested in different variations

You would think an older guy would be interested in ordering the same dish he has always eaten.

That is not the case, according to my humble opinion. When you have been practicing sex for more than 20 years, you do develop a lust for different variations.

A normal short missionary session is not as exciting for an older guy as it would be for a younger guy. After all, he has done that 1000 times.

He wants to experiment

Most older men require something new and unexpected to fully awaken their sexuality.

Luckily most older men know this, and they will try and surprise both you and themselves. I have only one thing to say; enjoy the ride.

Also, if you want to drive him wild with desire, check out our guide on How to create sexual tension with a man.

5. Older men are more likely to have a very particular kind of kink

I don’t know if a kink is something that gets developed over a lifetime or if older guys are just more open to confessing about their particular kink.

But all the older men I have slept with have had a very specific kink. One guy liked to have sex in semi-public places, another preferred anal sex, and a third liked to be tied up and spanked.

Older men are more comfortable talking about their desire

Most younger guys might be too ashamed to ask you for whatever their heart desire, but not so with my older guys.

Or maybe I’m just so open that it inspires all these older men to come clean to me?

There was also the older man who really liked all kinds of rain clothes… I wore wellies and a heavy rain jacket… He even got a hard-on from umbrellas, I kid you not.

6. Older men are not so sensitive to body hair (and other very natural parts of your body)

I feel a lot of younger guys have unrealistic expectations of what a woman really looks like. They are turned off by a bit of unexpected hair or a rough patch of skin. They might expect you to be fit, skinny and smooth.

Older guys know what real women look like

Older guys, on the other hand, have seen enough of life to appreciate you for who you really are. They will ask about your scar and take you in, the whole of you, with both their eyes and their hands.

After all, some of them were around in the 70s when a huge bush was the norm rather than the exception.

7. Older men will be appreciative of you just being you

When you dish out sexy time to someone 20 years older, you are doing something unexpected. Most older men will appreciate this and show a reasonable amount of gratitude.

Their gratefulness usually comes in the form of a greater willingness to satisfy you and ask you for what you need.

Don’t be afraid to tell him exactly what you need

Do take advantage of the opportunity and ask him to satisfy those hidden parts of you. Be wild and be free. Your older guy will appreciate your playfulness, spontaneity and youthful fire.

8. Older men are more stubborn

After reading all the positive things, I have to say about sleeping with a man 20 years older than me, you might be ready to give him a call and dive right into the action.

So let’s come back to a fair and balanced perspective and go through some negative points.

I do find older men unnecessarily stubborn. They usually have a schedule and most of them don’t like too much spontaneity. They might have kids and an ex-spouse to take care of.

Are you prepared to deal with the logistics?

Sexually they are usually pretty open, but not even sex is just about sex. There is still a lot of logistics surrounding the shagging, and I have found older men to be very set in the ways when it comes to how and when a good hook-up should take place.

If your older guy is someone you don’t only see as a potential lover but consider for a relationship, I recommend our guide Pros and Cons of Dating an Older Man.

He might not be a genie of spontaneity

You might have to lure him away from his routine to be able to enjoy all that forbidden fruit. Older men often have a very exact idea of how things should be done. They are not so willing to just go with the punches as a younger guy would be

9. Older men will not be as hard as you are used to

This has to be said. You will never know there are so many ways to be a bit soft in that department unless you start sleeping with a man 20 years older than you.

It takes a lot longer time for him to get a nice hard erection. Once he gets it, the hard-on can be a bit fickle and demand a certain kind of upkeep. You might be diving down below the belt every 5 minutes to try and get things going with the help of oral sex.

The recovery period is much longer

He can also be less than rock-hard during the penetration itself. Not to mention that it sometimes takes hours (or days) before he is ready to go again once orgasm is reached.

I have slept with young guys who pretty much have a constant erection and need about 20 minutes to recoup before they are ready again.

Expect no such miracles with an older guy. Accept him for what he is. Even a guy in his 40s will not be as unbelievably hard as someone in their 20s.

10. Not wanting as much sex

So a lot of young guys are initiating sex like it is their last day on earth and the survival of the human race are resting on their shoulder.

With an older man, you don’t get this eagerness. Most likely, his penis has seen the inside of enough vaginas (or the same vagina for decades) that the need to have any competition with himself has worn off.

Older men are more about quality than quantity.

You might not get it as often as you would want

If sex is something you like to order on a daily basis, be prepared for your older guy not to be able to keep up. Especially not in the long run. Older men and their precious penis do need time to recover.

A Final note

I’m all for sleeping with older men. They are usually a sweet fountain of sexual wisdom and unexpected technique. Give him a chance and your vagina will thank you for the chance to have a new experience.