Since 2015 I knew I liked older men, but a year later I was still just at the beginning of my personal sexual revolution. The dating app world was my oyster and I wanted at least a dozen to try with mignonette, lemon and all the fixin's! My previous sexual experiences up until then were pretty plain, not all vanilla, but age appropriate, monogamous-focused, it takes two-kind of stuff. So as I embarked on my exploration, I felt a few trips to Cougar Town was imperative.
I first rode in to Cougar Town while I was in culinary school - this was 2014. I fancied this tall, troubled gent from New Orleans. I'm at absolute sucker for a Southern accent. He had been stationed in Iraq as an 18 YO fresh out of high school. He was in the cool crowd at culinary school and we barely talked except when necessary during class. When everyone would hang out in the evenings, he definitely got the shittiest. Lots and lots of Jameson. I admired and was empathetic from afar.
One night deep into the drinking evening with the class, I was talking to his best friend. He and I had not been seeing eye to eye in class - that's the polite way of putting it anyway. After our little tiff where I'm pretty sure I told him he was a fucking dick, I can't actually recall how or why I mentioned I had a wee little crush on his friend. The next thing I recall is New Orleans sitting on a bar stool, me standing next to him and him with his arm wrapped around my waist.
After the bar closed at 2AM, I went back to his - a room he was renting in a house where the owner was asleep. We were both clearly inebriated, but then he started smoking weed.
When we came back in to his room, I was talking off my boots when, standing in front of me, he threw a pillow on the floor and without a word, starting taking of his pants. I obliged, I mean what a gentleman - so thoughtful of him to put a pillow on the floor to comfort my knees why I swallow his dick!
After that night, we went back to not talking to each other.
I took a two-year hiatus from cougaring. Until Darling Nicky - see Part I and Part II.
Left disappointed again, I moved on to the next town with hopes of better sites...AND pleasure.
Then when a 29 YO (I am nearly 41 YO at the time) messaged me about a year later on whatever dating app I was on then, I said WTF, maybe third time will lead to an orgasm??
Cougler was first generation Jordanian, short, light-skinned, broad chested and thick with muscles and dark hair. His parents owned a casual restaurant in a town about 30 minutes away and as a traditional family, they all lived together in the apartment upstairs. He helped them out on the busy weekends, but M-F drove about an hour away to work at a big Bay Area company HQ.
A drop of young drama commenced.
"I'm here, but I'll be waiting outside. I just noticed by ex bf brother is working the bar. Rather not see him."
We chose another bar and I actually had a great time. As we drank margaritas, he taught me about tequilas and his family history from Jordan. I was intellectually stimulated! Amazing and so fucking hot! But one rule I still have not broken is no sex or coming home with or inviting home on a first date (well...see Prison Dyke - Part I and Part II). I walked to the bar, so I let him drive me home (also kind of a no-no).
But with all that brain activity going on in my head, I know my pussy was not far behind.
We parked outside my apartment for a make-out sesh. His lips were big, soft, wet and he kept his tongue in check. Leaning over the console, he put his hand on my thigh over my jeans and inched closer, gripping firmer.
Torturous!
I was able to pull myself away and end the evening.
