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Part 4: Met 3rd Woman Online – My First Cougar Date – Something To Think About

My First Cougar Date
Photo: Cougar Life


Part 4: Met 3rd Woman Online – My First Cougar Date – Something To Think About

It was on to the 3rd person who I was to meet online. This was a date I thought about for a while afterwards. I had now experienced my first cougar in real life.  Online dating had become even more interesting. Had I done something really creepy or was this actually something that I could get used to ?

I had now met 2 people and had sex with both on the first dates. I had been making the initial contact to the people I was meeting but I was also getting many unsolicited messages from other women. A woman, who I will call Dee, caught my attention. She was 15 years older than me but looked much younger so we exchanged numbers and we began chatting. I was now talking to my first cougar.

Dee was an architect and actually owned her own firm. A couple Google searches revealed she was the designer of some major projects and quite talented. When we spoke she was very down to earth and hip, didn’t come across like some old lady. She lived about an hour away so it would take about a week before we could finally meet.

I drove to an outdoor bar / restaurant on a lake near where Dee lived. I was thinking I was about to meet a catfish. She looked great, nowhere near her true age. For my first cougar this looked like a good choice. This date was different as she did not seem like someone who was going to start kissing right away but more reserved. We had a couple of drinks and some bar food. The atmosphere on the water was great so we decided to take a walk. The lake was surrounded by a nice man made beach.

We walked holding hands and talking. I decided it was time for the first kiss as we had been together for about 2 hours already. I swung her around and just landed one. She was great and we now had broken the ice. She was a good kisser and this was now looking like great chemistry.  We dropped to the ground and before I knew it we both had our shirts off. This was about as cool as it gets. She suggested that we go back to her house, which doubled as her office. My first cougar had become really sensual.

We drove separately to this gated, what I would call, mansion. WOW, she had quite the home. We went inside to this incredible foyer with vaulted ceilings and etched glass doors. We made our way to her home office which had lots of cool drawings of projects she was working on. She asked if I wanted a drink so I said sure.

We walked to her kitchen, which had a Sub Zero refrigerator and Wolf gas stove to start. She poured herself a glass of wine and I had a light beer. No more than 2 sips in and we were touching again.

We moved to the living room and onto the couch. I just pulled off her pants and left everything on and just went for it. We were like kids in a backseat of a car, still half-dressed having sex. This was quick and great !

We put our clothes back on and just resumed talking like nothing had happened.

The conversation took an interesting turn as she described how she lived in this huge house alone as her kids had all moved out years before. She asked how I felt about moving in with her. This was a first for me.

She then began to touch me and put her head down near my zipper. She began to unzip me so I just pulled my pants down and she began sucking on me. This woman was hard core but it was nice.

Now after getting off for a second time, I told her that we should see each other again and talk more about the possible cohabitation. She agreed.

I drove back home and sent her a thank you / goodnight text. The next day I text her and told her I wanted to think more about our night and we would see each other again soon. My first cougar experience may have landed me in my first second date with the same person.


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