Sunday, May 2, 2010

Older Women as Sexual Mentors

I have often imagined what it would be like to be a teenage boy with a sexual appetite that is out of control, trying to get enough verve to ask the girl out at school while masturbating under the bed covers at every opportunity. It seems to me that hormonally-challenged young men have no business running around with girls their own age – at least, not until they’ve found a way to relieve some of the pressure, and learned a little bit about how to harness their energies. Because as we all know, it is common for girls to feel coerced into sex before they are ready – and many of us caved out of the need to be wanted. It’s still going on today. Girls as young as 11 or 12 are giving out blow jobs to boys in order to be cool, and to gain acceptance from their peers.

But I digress. What I mean to be driving at is that many teenage boys could benefit from a channel through which to express their needs, and some practical advice on how to please a lady. And who better to offer that than an older woman?

Movie star Michael Douglas knows about this all too well. Recently, on being interviewed by Elle magazine, he confessed to having been bedded by two friends of his mother’s when he was 16. And since then, pop sensation Justin Bieber (also 16) has revealed a similar wisdom, having come out with his own interest in older women. These are just two examples. That young men (especially major stars) talk so much more easily about this kind of attraction demonstrates one thing for certain – times are changing. It’s not just a Mrs. Robinson phenomena anymore.

There is something that just makes sense about this picture. A woman in her sexual prime has just as much to gain from initiating a young man as he does, and it’s fun for both of them. If boys had the benefit of this experience more often, they would be far more versed in matters of both the heart and sexuality – and that is something we can all gain from. It would be good for their self esteem, and good for the women they end up with.

Now this little liaison I am painting is, of course, distinctly different from that of an older woman – younger man relationship that endures, even if they both work for similar reasons. But I think it deserves to be taken just as seriously. In some Indigenous cultures, women were required to assume a temporary post as a teacher of sexual secrets to young men, as a form of initiation. If receiving this kind of direction were the norm in modern day society, the impact on a young man's growth and maturation would be something to observe indeed.

Just imagine the possibilities.


Andy Donovan said...

Interesting take here Jesse...I often wonder what life would have been like had guys like myself had had this type of experience in our younger less awkward we might have been around the fairer sex. Thanks for sharing, Andy

Jesse Mendes said...

Hey Andy I appreciate your comment! I was hoping to hear from men -- in fact, any men reading this, can you indulge me? Do you agree with Andy? Did you have an experience with an older woman when you were young?

Lise said...

I think its a wonderful idea! I'm in a committed rship but its sort of exciting to be a 'mentor' to a younger man to help him through those stages, we can be so much more understanding, patient and aware of all of those issues instead of two young people fearful of sex, their first time and all the nuances that brings (gods do I remember that!). Having someone who has been there before would take a huge load off, literally and figuratively! Wonderful post Jesse xxx

Anonymous said...

Interesting post, Jesse. As you say, in many cultures, being initiated by an older woman is a rite of passage for young men. Perhaps this idea of learning from an older woman is part of the reason that more and more younger men are openly enjoying the company of older women.

The one thing I'm not sure of is how the women would be viewed by society if this was the norm. Women dating younger men are already frequently portrayed as sexual predators, so even in the context of an adult relationship, it could lead to their being further vilified by the masses.

Do I think young men could benefit - absolutely!
Do I think women would pay the price - unfortunately, yes.


Jesse Mendes said...

Lise, thank you for your thoughts -- nice to know that someone agrees about how this would "take the pressure of", so to speak. Well put.

Jo, as always, I appreciate your thoughts and commentary. I don't agree with you that "women would pay the price" though. Mostly because I believe that in order for "older women as sexual mentors" to be actualized in modern North American culture, sweeping, significant changes would first have to take place in the society at large: namely, how older women are perceived, valued and considered. With those changes in place, it would no longer be an issue.

There is still a great deal of work to do. But I thought perhaps that somewhere to start is in public discussion that encourages young men to come out and talk about their experiences with older women when they were young -- and where that is lacking, the experiences they might have wished they had.

In friendship,


Dave Bartlett said...

Older women with younger men is one thing, (though the opposite situation of an older man with a younger woman often brands the male as a 'dirty old man,') but when you talk about 'boys' I think you should make certain that your readership are aware of the age of the 'boys' you're talking about. Many boys, well under the age of consent are in search of sexual experience and gratification, (I know I was, back in the day)and 'masturbating under the bed covers at every opportunity' is a perfectly acceptable solution to their frustration, but receiving their sexual experience from an 'older woman' is as much paedophilia as any other example and is equally immoral and abhorent. Have fun with your 'younger men' if you can find them, but hands off our kids, whatever their gender.

Jesse Mendes said...

Hi Dave

Your comments are appreciated.

Rest assured, when I talk about teenage boys, I refer not to boys under the age of consent -- I have no interest in promoting, nor do I have any tolerance for, paedophilia, exploitation, or abuse of any kind. I would have thought this was clear in my piece, since I use the expression "teenage boys" and "young men" interchangeably, but I understand your point just the same, and I think it was worth bringing up.

For the record, however: my post refers not to me personally, or some supposed pursuit on my part of teenage boys -- it explores a concept I think our culture might gain from, should times and thinking be different. As well, I don't think my post suggests that "masturbating under the bed covers" is an unacceptable solution to a teenage boy's frustration. It is, without a doubt.

Thank you for taking the time to write, and granting me the opportunity to address this.


Shauny said...

I couldn't agree more with your assessment. There is a lot of confusion among young men when it comes to this type of subject matter. An older, experienced woman who is willing to mentor and guide a young man into adulthood is a wonderful thing. We should be following the example of the indigenous cultures you mentioned. But in today's society, sex is so taboo and is still to this day looked upon with scorn. Males and females are taught to hide their sexuality and to never talk about it. This is why we have so much sexual deviance and perversion in America. In Europe, sex is not that big of a deal in the public forum. Unlike America, France isn't a nation of giggling 10 year olds whenever they see "pee pee parts." In Paris, it wouldn't be strange for two people to use their lunch break for an afternoon rendevouz. Enjoy a glass of wine, make love, have a few smokes, then head back to work. This laissez-faire approach to life is what motivates me to adopt the European approach to sex. I often here Europeans criticize America's attitude towards sex by stating how violent our movies are, but how censored our sex scenes are. Anyway, sorry for my rambling, but I'm just fascinated by this subject. Great writing Jesse, keep up the great work!

Shauny said...

Dave. I think you're paranoid. And older woman with a 16 year old male is not the same if it were the reverse. And that's just the way it is. It doesn't help to take ultra-conservative/religious stances on these things.

Jesse Mendes said...

Hey Shauny

I enjoy your thoughts on the European approach to sex and sexuality very much. I, too, prefer this way of looking at, and living, life. Stay in touch!


Joan Price said...

> Justin Bieber (also 16) has revealed a similar wisdom, having come out with his own interest in older women.

As long as they're not over 40, he says. Clearly he hasn't met women like us yet!

Joan Price

Author of Better Than I Ever Expected: Straight Talk about Sex After Sixty and the upcoming Naked at Our Age: A Straight Talking Guide to Senior Sex.

Join us -- we're talking about ageless sexuality at

Jesse Mendes said...

Hi Joan

Yes -- I tweet about Justin's love of older women regularly! Thanks for the note. Jesse

Nate Shapiro said...

"In some Indigenous cultures, women were required to assume a temporary post as a teacher of sexual secrets to young men, as a form of initiation."

I am just curious where more information can be found on this subject. I am interested in studying rites of passage and I remember seeing a very brief passage on older women acting as sexual mentors to young men in indigenous culture in a magazine article a very long time ago. I cannot seem to find very much information on the web though. Please let me know if you have any good sources. Thanks.

Jessica Mendes said...

Hi Nate

I don't know of any specific resources on this subject -- I learned all about it through a body of oral teachings, as much of Indigenous culture is passed down orally. But you will definitely find some leads by pursuing the concept of the Sacred Whore or the Sacred Prostitute -- your local library, a Google search, or even books related Matriarchal teachings or shamanism. There's tons of stuff out there -- it's all in how you search and what you search for. Use your intuition in following leads, and be wary of charlatans or people out to profit from, or exploit, Indigenous teachings -- there are tons of those out there as well.

Good luck.

Jill Kozak said...

What a fantastic post! I am working on a Sexual Revolution project that is aimed toward trying to make the business of sex more stimulating, positive and sustainable. Throughout the research, we concluded that an idea like this would be a perfect solution to the problems associated with both younger men and older women. It's a great way for younger men to really learn how to treat a woman, while the older woman gets to teach, have fun and play with a younger man!

Do you mind if I cite this post in my research? I would be very interested in including it.

Please let me know. My email is


Jessica Mendes said...

Hi Jill

I love your enthusiasm and am very intrigued by your project. Have written you on your email address to find out more. Thanks for writing.


Anonymous said...

I have a slight confession to make, I am a 17 year old young man and often catch myself fantasizing about older women. I don't speak out about it often because in the U.S sex is largely considered taboo especially with someone that is older and of the opposite sex. From the stand point of a teenage boy, it would boost my self esteem and confidence as a young man if I knew how to handle myself and how to confront a women in general and be less awkward so to speak as well. This is a wonderful concept.

Jessica Mendes said...

You would be surprised how common older women - younger men relationships / liaisons are. The media just hasn't paid much attention, and when they do, it tends to be reduced to stereotypes (like the "cougar" and the "cub").

I am thrilled that you took the time to write and share your experience. I hope you will consider checking out the SeptemberMay dating site when we launch -- dedicated to celebrating authentic older women and the men who love them. Stay in touch. You are not alone in your experience.


Anonymous said...

I was lucky enough to have an older woman as my first sexual partner when I was 17. She was 38. That summer she transformed me from a quite shy boy to a confident young man. I am very greatful for it, and I don't think that could have happened with a girl at my own age. Later, when I was 19, I had sexual relationship with a 46 year old woman for over one year. To this day, I consider these as the best sex partners i've ever had. The intensity and communication was like nothing else.
Partners from different stages in life have fewer expectations from each other, not trying to fit in a role, and thus become more themselves. not afraid of show any kind of emotions whether it is shyness or arousal, just free in every sense!
I think it is completely natural for young men and women twice their age to meet. Maybe there is a good reason why it is often kept as a secret, 'cause its the best sex there is.

Jessica Mendes said...

Dan, this is beautifully put. Would love to connect with you -- perhaps when we launch SeptemberMay, you would consider posting a blog on the subject? Let me know if you'd like to connect -- you can write me at jesseheretic (at) yahoo (dot) com.....Thanks for writing. You are very articulate!

Anonymous said...

I am an older sexual woman and I know beyond a doubt that if a man is too male and isn't receptive to learning the fine art of love making from a woman who knows this art it does no good to teach this skill to the young man. In fact what I have encountered is that most young men are to arregant to think they can actually learn to make love to a woman from a woman any woman. I am a mentor and have had my share of younger men and the majorety of them actually thought they were good lovers and felt insulted when I tryed to share what pleased a woman like me and I am not that kinky so what I had to share was not out of line. Most would rather receive than to give pleasure and that is where they are mistaken. Very few know how to please a woman and if they did the would have the world of women in the palm of their hand giving as well as receiving!!! thank you; The Earth Goddess

Jessica Mendes said...

Hello Earth Goddess,

You are absolutely right -- if a man is not receptive there is no point in trying to teach him. My heart goes out to you that you have had so many of these experiences. I've had a few myself. The best I can tell you is that there are men out there who DO want to be taught; men who appreciate what older women have to offer. In fact we found so many in our research we were astounded. Please look out for SeptemberMay. They are out there, it's just a matter of staying open to having a different kind of experience.

All the best to you,


Anonymous said...

Hi Jesse, thankyou SO much for your blog on this subject. I was having dinner with a friend last night who doesn't really understand my relationship with a much younger man and in conversation she said to me, "but why is he with YOU?" She didn't get it. I wanted to explain it to her so I came looking on the internet for 'older women/younger men' information. I, too, had read about how some tribes initiated their younger men and I was sure this was common in some cultures. Which is when I found your blog. I think I can add weight to your argument...

I am an Australian woman of 54 and have a lover who is 24. This wasn't in my life plan! We met online after I decided that looking for a boyfriend my own age was just not working. I was willing to live without a relationship, but being without sex was, for me, not an option. I'm not a nun!

When he contacted me, I was very wary at first, because he was so much younger than me and I had been mucked around by younger men before, while looking for a 'friend with benefits'. But we have both been amazed that this relationship developed quite quickly from simply meeting up for sex, into real friendship, mentoring, and more.

I consider this to be a mutually beneficial relationship where two people have come together at a time of our lives where we both needed something.

I am learning about men from a beautiful young man who is attractive, funny, articulate, intelligent, and a great communicator. The sex is amazing and always has been (he learned from other older women). I believe we have met for a reason. He appreciates someone who listens, understands, and doesn't judge him at a time in his life when he is searching for his identity in a world that offers so many more options than we had when I was his age.

He also has the freedom to have (safe) sex with other women, no strings. While he has encouraged me to do the same, I don't need other sexual partners, he is enough. We have both expressed how fortunate we are and how grateful we are to have met each other.

To our mutual surprise, we have been seeing each other for over 2 and a half years now. There have been quite a few ups and downs as we negotiated our emotional attachments to each other and it's not a relationship that there seems to be a blueprint out there for, lol, so we have been learning together as we go along. I have been married and in 3 other significant relationships before, but I can say that, between us, this is the most open, honest relationship that I have ever had with a man. I think it's because we both went into it knowing it wasn't a 'forever' relationship so we had nothing to lose by truly being ourselves. I am taking this learning into my future relationships.

My friends know about him, and are mostly extremely understanding and non-judgemental as they can see that I am softer, happier and have changed for the better. He keeps me a secret, which I do understand.

We both know this isn't forever, we are both still searching for our life partners and encouraging and coaching each other, I might add! He wants to get married and have children some day, and I want a man who is closer to me in my stage of life. After all, I have my own house, business, money, am established in my life, and he is just venturing out into the world, going from boy to man.

We have talked about 'when this finishes' and both feel very strongly that we will want to continue as friends. Whether we can or not remains to be seen, but whatever happens, I feel blessed that I have met such a beautiful young man who has enriched my life as I know I have his.

Thankyou for allowing me to share my story,

Jessica Mendes said...


What a beautiful story! I don't know what to say except that I find this *so* inspiring. I am involved with a project I was wondering if I could speak to you about. Would you be open to connecting on regular email?


Anonymous said...

Hi Jess, yes I am happy to email. Please post your email address so I can connect. Tx, Renata

Jessica Mendes said...

Hi Renata

You can reach me at sensorybeing (at) gmail (dot) com

Anonymous said...

She wasn't by any means 'older', but she was older than me and in my young opinion more mature (at least in sexual things... or appeared to be), I was 12 in 7th grade and she 13 in 8th... post-graduation after 1 year of flirting, she pulled out all the stops... she really wanted me to man and be a man for/to her (though I so much a boy in so many ways haha:), she sexy danced for me in the context "you can't dance to a rock song" (she was a 'rocker' chick) and her 'proving me wrong' with a sexy dance, then both of us standing under the staircase with her about to leave her saying "Hell!" after 5 long ass seconds of me wanting her to 'man up, initiate me, and kiss me' haha... she did, probably got turned off after that being the man and woman moment for her, me kind of just sitting and enjoying her doing everything for me... though she really helped me to man up and take the initiative if not the next year.. but in high school. Thanks alexis :) Love you babe :)

Anonymous said...


My names Shawn, I love reading this article and an older mentor is something I'd would love to have, if you're interested email me.

shawndavidcampbell [AT] gmail [.] com

I'm 19 and single ;)

Anonymous said...

I am a 16 year old male and I couldn't agree more with you Jesse. An older woman as a mentor would be just what I need to develop and enhance my sexuality at this stage in my life. I have actually been thinking about this for a while, but felt too embarrassed to express it. It is great to hear that I am not the only one who thinks this would be a good idea! Any suggestions on how I could go about starting that type of relationship safely?

Jessica Mendes said...

Dear Anonymous,

It's good that you reached out, and rest assured you are not alone -- far from it. I have been part of a research project that shows overwhelming interest in older women from younger men -- interest that goes beyond the "cougar" stereotype. The reason you feel embarrassed is because of how the media typically portrays this dynamic -- typically fetishized rather than normalized. It's a shame. I want to be part of changing that but the project I and my colleagues have in mind has been put on hold due to lack of funding.

In any case, you have taken the first step, and that's important. I'm not sure what you mean by "safe" -- if you are talking about STDs then you can go to a health clinic in your area for information, or simply use condoms. And as for inching your way out there, just stay open and follow your intuition. Be yourself. That is the biggest turn on of all. And if you can find the courage to be open with the right person, it may just happen for you. Trust me, there are women out there who would love to assume this role for men who respect and appreciate them. But it all starts with a shift in perspective. You're on your way.


Eager Student said...

Thank you!

This piece has made me feel so much better about my feelings and less guilty about my desires. For a long time, I've fantasized more and more about sexual experiences involving older women. I find women older than myself insatiable and have trouble explaining my interest in them. I could never verbalize my desires anyhow, as no one would understand.

I can't provide an instance or occurrence relative to a shift in attraction from younger to older women. It just happened. Perhaps it was girls my age with huge expectations? Maybe I was made to feel incompetent or under-equipped as most of my "knowledge" came from porn. I was and still am annoyed that there isn't an easy answer to giving women screaming orgasms. I'm inexperienced and not exactly 12 inches...

I'm eager to please. Perhaps even desperate to give women pleasure but I am learning ever so slowly. There aren't exactly bunches of classes with a hands-on approach I can use (or at least not at my local community college).

Thank you for letting me know these types of situations have some hope. I'll keep my fingers crossed and hope that I can somehow meet an understanding woman who will help me become a more mature, refined and capable sexual partner and lover.

Jessica Mendes said...

Hello "Eager Student"

Thanks so much for your note and I'm glad to hear the blog helped. Take heart there are many like you out there, the media just doesn't tend to pay attention. You may also want to look up Cindy Gallop and her TED talk called Make Love Not Porn -- fantastic resource:

Eager Student said...

You're welcome and thanks for that additional reference.

Although I have to believe you telling me that my sentiments are more common than they may seem, I have trouble finding like-minded individuals to share these feelings with.

I suppose I'm not looking hard enough for an older woman/younger man coffee shop haha

Anonymous said...

Jesse, interesting post. The reason I got here was I was looking for a older female mentor for younger and even older women. There is so much misinformation or lack of information that I see in people, mostly the younger females. Where are the older women teaching the younger women how to love their husbands? Where are the older folks teaching the younger folks anything? I've tried to teach my kids and get them ready for life and they've all turned out well. But, I don't think I did a very good job because I got nothing in the line of mentoring from my parents or anybody else for that matter. I got what everybody else got through typical, info from parents, school, church. I'm seeing more and more the value of mentoring from the older to the younger.

Steve L.

Jessica Mendes said...

Steve, thanks so much for your note and apologies for tardy reply -- have been battling some health issues. I just wanted you to know I hear you loud and clear -- Amen! There is so much misinformation out there, and young people are too often being reared by technology and porn and religious dogma that discourages any real education. I couldn't agree with you more. I'd love to be able to do something substantial about this and have great ideas (and even a business plan) but have lacked the funds to make it happen. Thanks for your post though. Was great to receive your comments.

Anonymous said...

Splitting this in two parts as it's too long. **PART 1**

My views(as a very unlucky 29 year old virgin, who will die as one, due to an accident at age 13) on young mens attraction for older women:

Whenever you read peoples opinions on this matter it's always the same old cliche├ęs, "Older women are more confident in themselves" "experienced and more laid back" etc. I'm not saying this isn't true, because it sure tends to be so. But this isn't the reason young men are attracted to them, it's merely a bonus.

First of all, let's just point out the obvious fact that we are attracted to GOOD LOOKING older women. We wouldn't pick an unattractive older woman over a young attractive one. But if the older woman(definition of which would be: someone old enough to be your mother) IS attractive then she has an edge over a young attractive woman.
I will now share my philosophical thoughts from my own "older woman"-attractions during my life:

I have always been attracted to older women, as well as girls in my age of course. But I definitily started to notice a pattern in my late teens; that whenever I was attracted to an older woman - THAT attraction was undeniably stronger compared to my attraction to girls my age. When I was in my late teens, my "attraction peaks" was for women in late 30s early 40s. In my mid 20s - it was for women a little over 40 to a little over 50. And now at age 29 it's for women aged 45 to ~53(55 is my roof and it seems to stay that way).

I have since then thought about why this could be. The first reason is that I find an attractive older woman(who has her attractiveness-peak in that age) MORE physically attractive than her younger counterpart, more luscious and something appealing and sensual about her skin as well as the soft mature, jet sometimes chiseled face(like this 45 year old woman for example ).
It could maybe have some biological reasons that women who peak looks-wise between 40-50 have extra strong genes. Maybe, but that's a weak guess.

But there is a mystery factor as well, something which cannot be explained by mainstream science, and perhaps more uncomfortable and a tad embarrassing to talk about. I have become absolutely certain of this the last months thinking about the subject.
There seems to be some energetic connection(at least from the male part, I can't speak for the older women) or an energetic gravitation which pulls young men to women old enough to be their mothers and make their attractions to such women so very strong. *I must emphasize that this has NOTHING to do with somekind of incestous desire ala Oedipus complex!!*
I have jet to figure out the exact nature of this energetic connection or gravitation, it is in no doubt some very, VERY deep stuff. I have a feeling it might even hold key significance to the whole mystery of human sexuality.

Anonymous said...


Part of what has led me to think of an existance of a "mystery factor" is the fact that the women I have been most attracted to always has been between 20-25 years older than me.
Also, one of my first sexual fantasies, at age six, was a strange one. I had a new friend I had met at preschool and we went to him after school, outside his house was his mother(aged ~35) doing gardening in string bikini(!). I couldn't help but to glance at her before we went in the house to play. That night I fantasised about entering her buttocks and being inside her body(whole me being inside), which made me aroused. Weird story, but I think it might have a connection.
I have also noticed that none of the older women I have been most attracted to have had children. It might be psychological, since I'm not fully comfortable with thinking about a woman who has children(especialy if they're in my age), but in most cases I have learned that the woman has no children AFTER I became attracted to her. I'm thinking there might be that the energetic gravitation is stronger if she has no kids, that it's purer and untouched?

My latest strong attraction for an older woman is this 53 year old who also has no children.
I can't quite describe how attracted I am to her, I'm not in love, don't have a crush, I just find her so enormously attractive. Sensual and beautiful. It's like there is a divineness to the attraction to these older women.

This is the first time I have ever written about my attraction to older women. I have only recently fully admitted to myself that older women is what I'm most attracted to.
I curse my accident daily, as it has ruined my life. It feels horrible knowing I will die without ever experiencing intimacy(sexual, romantic, or just closeness). Especially when I read about other young mens experiences with older women, I envy them so much it gives me terrible anxiety. I know had I never had that accident I could have had that experience as well, I know it would have been so special, so divine... :(

Jessica Mendes said...

Hi "Anonymous"

I appreciate your thoughts and the risk you took in expressing them. I hope you found the experience cathartic and I hope other readers may appreciate your sentiments as well. Not sure what else to say beyond that. Dealing with some serious health issues myself so not a lot of time for long, reflective letters.

I am not sure that cursing an accident is a good way to live -- if you are going to stick around why not find an alternative; an attitude that will bring you more joy? As a person with a disability myself I am empathetic to whatever limitations you might have, but I don't agree that one should just give up on any form of intimacy at all. That said, it is your life. I just hope you can find a way to live it that brings you pleasure, especially important for those who endure extreme hardship. My good will to you -- all the best.