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.
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.
I was able to pull myself away and end the evening.
“You are an extremely beautiful and sexy woman. I’m looking forward to exploring your body. As you got up out of the car, I got a small glimpse of your tattoos. It was a bit of a tease.”
“I like to be a bit of a tease. Your hand on my thigh almost did me in though…”
“I don’t know if I’ll be able to hold back next time.”
The next day he sent me a 3 minute unsolicited video of him stroking himself. Hot, but ugh.
We continued the sexually tense chatting as I headed on a birthday trip with Nerdie to Reno.
“Happy Birthday! Maybe later next week you can unwrap your bday gift. <winking emoji>“
“Thanks for remembering…so sweet! Let me guess…this gift is in your pants??”
“LOL yes maybe I can send you some more teasers in the meantime.”
This round included a full nude in the mirror – face, cock and all!
“I want to lick you all up and down. I’m dying to get a taste. The anticipation is driving me crazy!”
I was losing slight interest – not that I didn’t find him attractive and nice – but the youthful, lack of nuanced approach was softening my dick. Still, I wanted to try him to hopefully erase my previous lackluster cougaring experiences.
“You know I’ve been thinking about you plenty over the past couple of days. I would love to see you tonight.”
“Why don’t you just come over? I’ll have some snacks and drinks handy, but I’ll warn you since I’m moving soon, my apt is pretty sparse…”
“No worries. There’s really only one thing that I’m looking forward to eating tonight. <winking emoji>”
<Eye roll emoji> with hint of cautious optimism??
Yes, we didn’t do much eating and drinking before he pounced. I was into it. I was routing for him.
When the make-out and dry heavy petting became overwhelming, he just stood up, literally threw me over his shoulder and carried me to the bed. Ok, hot.
I was looking forward to a good tongue lashing and that’s exactly where he went first – hooray!
He got going, I was getting comfortable. Closed my eyes to cut off visual sensory so I could appreciate the touch. He worked his way down from my breasts to my inner thighs, kissing, rubbing, licking. The anticipation was now driving me crazy.
He finally settled in between my thighs and roped his arms around my legs for leverage. The first touch of his tongue on my clit sent shivers running through me. Oh the spell will be broken tonight – Cougler is it!
Before I could enjoy my excitement at the upcoming orgasm or even concentrate on getting myself there, it was over. Could I even have counted to 10?
The rest of the evening was fun, way more than New Orleans but my disappointment was on par with Darling Nicky – what a let down. After he ceased focus on me, it was all about him. I did enjoy his hard, hairy bod! I even said so the next day.
“I loved every inch of your hard hairy bod! 😉 So you mentioned there was a girl who really helped you up your kissing game, interested in addl lessons??”
“I’m good with constructive criticism.”
“I just find guys in their 20s rush, and that’s why I’m not interested in second rounds as much as I like to touch and admire. If you are open, I’d like to alter that scenario. If nothing else in my life right now, I’m open and honest…”
“I appreciate your honesty and much rather you tell me the truth than have me keep going about it the wrong way. I promise to be more patient and attentive to you the next time we meet.”
Well, ok, Cougler.
So we picked back up with our sexually charged texts. I got excited again. It would be fun to teach a young buck better tricks. That’s part of what you read about why young men go after older women, right? To get a lesson or two?
But unfortunately life got in the way. He kept trying – would text me when he was in my town, but my interest fizzled. Do I really want to spend the time, patience and energy being a teacher or get some instant gratification in my typical form – not as a Cougar, but rather a sexy Panther!