The Cougar Files: Part 1

Two years ago I set out to write a book chronicling what happened when I took advice from self-help dating gurus.  I read seven books on how to get and keep a man and did the best I could to follow that advice.  The books ranged in levels of militancy in terms of how to behave—but mostly they all agreed to avoid having sex with men so they could enjoy the chase.  My lack of success was staggering.

At that time I figured if I wasn’t going to be having sex with the men I was dating (which wasn’t necessarily the case—but I did try), I was going to find men I didn’t want to date and have sex with them.  These Mr. Right Now’s ranged in age from 21-32 and were delightfully horny.  I met them on the “dating” site Cougar 911.

On my very first date with a young man we met for drinks, and I found out almost immediately that the vast majority of the women on the site were not “real.”  The ads were phony so that the guys who clicked on a picture would be transferred to a porn site or site for local prostitutes.  Invariably, the other women who did not fall into those categories were also phonies–they were scams looking for cash.  I didn’t really know how to respond to this information.  Here I was paying good money to be on a site so I could meet young men to fuck and I was the only woman there for that reason?  How could that be?  What did that do to my situation?  Would the guys give up because everyone else was a fake, or would I get all the good ones?

The afternoon I met Boy Toy, we had lunch, played in my pool, had an amazing dinner, and screwed most of the night.  He was handsome, short, classy, away for business half of his life, and lived in a storage unit the other half.  I never visited Boy Toy’s man cave, but I heard he had it decked out with a shower, bed, living space, and room for one of his trucks.  I actually liked the set up because it meant he wasn’t itching to get back “home” and would stay the night or spring for a hotel on occasion.  It also meant he wasn’t spending a lot of money on rent and spent that extra dough on me.

Another favorite Young Gun I met during this time worked his ass off as a chef.   He would get off of work in the middle of the night, come over for a few hours, and then leave.  For all I know, he could have been a bona fide vampire.  Young Gun’s mother was eight years older than me and expected him home at some point in the evening.  This meant that we basically had sex for four hours straight and then Young Gun would get dressed and head home to Mama.  I loved his curly dark hair, chiseled features, and soft mouth.  He was so good looking, in fact, that I couldn’t believe he didn’t have a girlfriend.  “All the girls my age want to get married and have kids.  Besides, who else would put up with my schedule?”

He had a point.

The men I dated with the hope of having a relationship would never have gotten away with sneaking in the middle of the night and sneaking back home again at the crack of dawn.  If I wanted to get serious about a guy, he sure as hell would not be living in a storage unit.  The men I wanted in my day to day world got to take me out for dinner and kiss me gently good night.  After they left for the evening, the young men I met on Cougar 911 would come over, get naked, and roll around in the sheets for a few hours.

While I certainly valued my time with the likes of Boy Toy and Young Gun, I never really wanted anything more from them besides sex.  We would enjoy wine together, go out on the town from time to time, and definitely hang-out, but it never felt like dating.  It wasn’t an arrangement that felt sleazy, either.  We respected our time together, treated each other well, and saw each other regularly for a good portion of a year.  Because we never tried to transform our relationship into anything except for what it was, it was easy keeping it going.  That was not the case for the Mr. Rights I was trying to meet and get to know.

As I read up on the dating advice from self-help dating books, I became more and more discouraged.  How was I ever going to have an authentic relationship with a man if I was behaving like someone completely foreign to who I really was?  If we did get to the point of really liking each other, when was I going to drop the façade and be ME?  What if we decided we were ready for a sexual relationship, and I was emotionally involved with the man, and the sex was horrific?

Both the book I was writing and the books I were reading eventually made it into the trashcan.  The Mr. Right Now’s have moved on, and I am now left to find a better way to have a vibrant sex life and a real, loving relationship with someone I genuinely care about.  It is a lot harder than it sounds.


  1. LOL! At Young Gun’s story, had to be home at a certain time, hahahahaha. Great writing!

  2. He was so sweet. I loved how he and his mother were so close. Once she got remarried (she married her ex-husband’s brother–but that’s another story) and moved out of the house, I never saw Young Gun again. Funny how things like that happen.

  3. Cougar 911? Mind blown. Looking forward to more Cougar Files.

    1. They used to advertise on a local radio station. I couldn’t resist.

  4. I had a few years where I was cougaring it up pretty hard (going as low as 19 years old…). Those dudes sure did get testy when I asked if they had curfews. I wasn’t asking it to mock the fact that they were so young, I was asking it to acknowledge that there was an age difference and show that I was sensitive to their needs!

    But anyway. This was a fun post to read, and obviously brought up memories for me. :D

    1. Have you written about those years by any chance? I’d love to hear about other experiences in the Cougar realm. Thanks!

  5. Thank gawd you put those ‘dating advice’ books in the trash bin where they belong.

    What’s wrong with incorporating all of your ‘selves’?

    The sexual, the practical, the romantic and the wildly funny….sometimes a great fuck can turn into a great date….however, turning that into a relationship is the stuff that I’m sure will give you fodder to write about

    1. Oh Ty! How I wish a man would love all of me. I am a whole lotta woman, you know. The right one will come along one day . . . . and hopefully I won’t scare him off:)

  6. [...] been a while since I’ve added to my Cougar Files here at Off Go the Panties. One of the primary reasons for this is that I’ve pretty much [...]

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