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Ask A Cougar: When to Have Sex With a “Cub”

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There comes a time in every woman’s life when she has to ask herself, does it really matter how long after the first date you wait before having sex with a guy? A question that brings me to another question from a reader calling herself, “Jaguar.” Jaguar was annoyed at having been left hanging in the last post (http://seasonedsex.com/older-woman-younger-men/) and asks, “How long should a cougar wait before having sex with a new cub?”

Good grief, is that really a question? Even when I was a younger woman, I never paid attention to the three-date rule (you know, wait three dates before jumping into bed). In fact, it’s a saintly day if I abide by the three-minute rule. Bill Maher had his “New Rules” and I have my, “SeasonedSex Rules.” Here’s the first one. Regardless of timing, if his penis looks hard and feels hard, it’s probably worth sitting on. I know, I’m bad but you’re allowed to be when people start calling you an “older woman” (that’s SeasonedSex Rule No. 2).

So, I’m joking. I’m not that bad. In fact, I waited over a year before I had sex with my cub, Michael. His youthfulness exuberance initially threw me off my game. But then the sexual chemistry would keep sneaking up on me, pulling me back in like a magnet. Michael eventually become the accidental cub. What I mean by that is I consciously decided to unconsciously have sex with him, which is easier to manage than it seems. A few martinis are all you need.

Now don’t get me wrong here, I’m not an advocate of drunken sex. I’ve only done that about 712 times in my life. But it does open up one’s perspective. And if it doesn’t ease the nerves. And, I was nervous.

Michael had asked me out on a dinner date via a text message with some business people he knows. Can you believe it? A text message! It was a first for me and it went something like:

Michael: cum dinner fri?
Pamela: who, where?
Michael: scotts. 8.
Pamela: you and me?
Michael: other people too
Pamela: is this a date?
Michael: yes
Pamela: will I be your date?
Michael: yes
Pamela: oh. LOL. ok

I don’t know why I put the, LOL. I must have just learned what it meant and wanted to seem cool.

Add a Comment8 Comments

After loosing my husband and became a widow. Out of being really lonesome. I met my current boyfriend he was 26 and I was 42 but then I looked 29. Anyway we have been together for nearly 9 years. We often get along, we have gone through so much together, good and bad and after HD lost his Mom, he has gone through a lot. He drifted away from us' suddenly without knowing he was seeing another woman. I was in shock heartbroken miserably stressed having anxiety attacks which I never did before. He told her all the bad stuff and left out all the good. This was just last year so he's 36 and she is sort of the same. She manipulated him about me just wanting him as my toy boy' when we not only lived together and had a true relationship. A marriage in my book!!! She made everything that was between he and I dirty as if I was taking advantage of him. He and her seemed to be all about sex. It has just killed all we had. Well ghat lasted maybe 5 months and we are back together again. But it hasn't been easy to say the least. I am still attractive and I am fun go be around, smart and loving, I would do anything for him. But I can't get passed what he did. He didn't even bother to say goodbye or to work out through our problems. Would I do it again znd fall for a younger man?. I don't think so. Maturity plays a big roll in my life now. I don't have time to waste with bullshit people. I am very active, music travel and I want a man that can be parallel to me. Don't get me wrong. I love Tom very much and will forever. Everyday is something, some days he feels good other is another story. Out sex life was good before he met this witch. After getting back together has been off and on.. he says get loves me but not all is about sex. I don't want just sex. I want intimacy love to make love.. sex you can get anywhere... I miss that connection... I feel greatly sad that he and I lost ourselves and all because of his escapades..... Don't falk for a younger man... they get tired of you and you are left picking up the pieces of your heart. It doesn't work like older men/younger women. That's a different deal....

May 12, 2017 - 5:09pm
EmpowHER Guest

I think you are a wonderful lady, and I would be proud to call you a friend.

May 12, 2017 - 5:03am
EmpowHER Guest

I'm so happy for you :) It sounds like you really enjoy him.. :) I wish I had the same luck and met a lovely cougar to share my body with as well :)

May 8, 2017 - 10:58am
EmpowHER Guest

I kinda got a kick out of the show. I'm 50 now. When I was 19 years old a very attractive woman 32 and I became friends. Looking back now my moral compass was all screwed up. We were friends for close to a year before something clicked and we kissed. It was obvious that she had not a lot of experience with French kissing but things began to smooth out. She was married and had a 9 year old son and while we talked it was also obvious that her sexual experience was limited to her husband of 14 years. I never pressed for anything physical and I always waited for her to make the move. I learned she had never experienced receiving oral sex and had tried to give it but her husband was not interested. She acted like a curious teenager with extended foreplay experimenting with a few things but because she was married I avoided the intercourse issue. I even felt bad for her husband when she told me that my penis was at least three inches larger and much thicker than his. Finally one night she decided it was time to saddle up and did the cowgirl thing. I was as shocked as I was surprised and she was the only woman I have ever been with who loved the missionary position because she could roll and raise her pelvis in tempo with my own thrusting. She was on the pill so we never worried about a condom. It was a great summertime fling but I met a girl in college the next semester and things faded away. She's still married to the same man up in Iowa and I wish them the best because I'm sure she learned to take charge. My wife has received the benefits of my prior experience. Cougars are find when one is 18 but after a guy turns about 25 the wonder factor is over it just becomes a woman who is older than he is.

May 26, 2009 - 5:44pm

Yes, it's beyond confusing, it's downright bizarre. I didn't see the show but my husband and I were talking about it today.... we were trying to figure out why the label "cougar" has been so popular and why it's even a big deal in our culture if a woman dates a younger man. I put in my two cents that maybe there's this somewhat positive aspect about it where as women become more upwardly mobile, independent and have the means to obtain things they need/want for themselves, they will have relationships with younger men who can't afford certain things and look up to and respect these women - it becomes a maternal/aphrodisiac kind of thing, not unlike the 18-25 year old young women who are always seeking out older, more established men... much of the motivation is about being parented, in a way; feeling safe with someone who knows more, has more power, more confidence, more money.

But the whole thing about the woman having to be super rich and super fab and super gorgeous is pretty nauseating... it gets back to people just using one another instead of people connecting and loving and enjoying one another. It's this vapid, sanctioned sort of prostituting oneself for "love" which, in fact, is quite empty and quite unloving in so many ways.

But in the long run I have to feel it is somewhat encouraging that we even get to have some kind of voice and image in the mainstream that sees aging women as hot. I mean - YEA!

April 17, 2009 - 5:27pm
EmpowHER Guest
Anonymous (reply to Aimee Boyle)

Or men; I have been "courted" by a younger man, and this has made me feel so good that I feel half my age, so Go Cougars!

May 12, 2017 - 4:58am
EmpowHER Guest

Thank you, Aimee. Glad you got a laugh out of it. I'm of such a mixed mind with this whole cougar thing. Last night TVLand aired the premier of The Cougar, modeled after the Bachelor. They start off talking about how they want to blow away the double standard and then proceed to describe how she just closed a $48M deal (cougars = sugar mamas) and every few seconds, they cut away to a close up of her kissing or walking into the bedroom or walking out of the bedroom (cougars = sexual predators). At the same time, they claim she's looking for true love, a real relationship. I guess they figure they're going to alienate too many women if they just work the sexual predator angle. It's confusing. It's screwy in fact how weird people get about the sexuality of older people. Sex is ageless but we're all so conditioned to think sexiness is a feature of youth end of story. Pamela, seasonedsex.com

April 16, 2009 - 5:19pm

You're so funny! I love your article! It's really bizarre that this "cougar" title is being thrown around everywhere. As annoying as it is, I have to feel positively about it; it wasn't so long ago that an older woman with a younger man was not only far from being "hot" it would have seemed downright absurd. We may have strange and uncomfortable buzz words for things but the fact of the matter is, it's pretty liberating to be considered an attractive, appealing and desirable woman to men of any and all ages (within appropriate boundaries, of course).
I agree with you that if you're chemistry is bubbling there's little to no reason to stick to some arbitrary set of dating and sex rules. However, I appreciate their existence because I think women have been devastated over and over again by insensitive men who led them on to believe they wanted relationships when they only wanted casual sex. In order to protect yourself somewhat, it makes sense; but if you're not feeling particularly vulnerable or at risk in terms of wanting something he doesn't or falling in love when he won't then by all means - ride 'em, cowgirl!

Also - I love that you had this "moment" in your article about him spanking you and your not noticing the cellulite jiggle - that's the epitome of good sex and I think what a lot of men crave as well - that We LOSE OUR INSECURITIES and just enjoy, enjoy, enjoy...

Thanks for this!

April 16, 2009 - 5:00pm
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