It was late summer, and I was attending my ex-roommate’s wedding on a quaint island not too far away from the city. She was a heartthrob to most men, so there were quite a number of them as her guests at this all-night affair. I, too, was lucky enough to have no trouble picking up or getting hit on. Dressed in a sharp black suit with heels, I was thirty and single – and tonight was going to be my first experience as a cougar.
A well-dressed, cocky smart aleck – who had taken advantage of the free bar – had become the beacon of my attention that evening. He was about five years older than I and was behaving like a jackass. I found it alluring at the time, as he became a challenge for me over the course of the night. Our flirtatious verbal jousting indicated there was something to be had between us. It was definitely a love/hate dance we were performing around each other. And as the drink filled him up more and more, his attitude grew with it. When I retreated back to my time-out corner, I settled down with Mr. Cock’s little brother. He was sweet, kind-eyed, and lovely to talk to. He put a little warmth back into my heart after I got knocked down by this beacon of love/hate. I would recover, then get back into the ring.
By the end of the night, Mr. Cock had me turned in so many directions, I wasn’t sure if we were going home with one another or going to punch each other out. It was now the last ferry to the city, and I was certainly getting on it. With enough of my own alcohol-driven attitude in place and feeling rather defeated as I was no step closer to taking my sparring partner home, I planted my two feet onto the boat, turned around and made sure to get in one last slag. I’m not sure how he did it, but he managed to whisk me away from the all-night challenge in one fell swoop, and all of a sudden I was locking-lips with Little Brother.
I was all worked up with such incredible sexual tension, so the kiss came with a great relief. We fit each other so perfectly, that I wondered how I had glossed over this cutie pie all night. He was into me – really into me. And I could tell he wanted to impress and please me.
We got off the boat and headed to the busy main road to get a cab. We stumbled over each other crossing the street, excited for the moment we could kiss again. He turned me around and pushed me up against the wall of the underpass. Due to the many cars casting their headlights on us by default, we were in plain view. This young man was already getting me high from his kissing and touching, when he decided to move one step further. Uncovering me from the spotlight of the cars, he unzipped my pants, and went down on me under the bridge. With my tiny white panties peeking out underneath my blazer and my smooth, tanned thighs beaming through, cars honked. I laughed and covered my face. I was enjoying it all. I had never been with anyone so sexually overt in public. And it just kept getting better.
We found our cab and not too far away from my home; it was just enough time for him to slip his hands into my pants and feel how wet I still was for him. When we got onto my porch and barely through the front door, we started fucking. We fucked in the hallway, in the living room, on the kitchen table, then down into the basement guest bathroom. We tried taking a shower, but ended up having more sex and yanking down the shower curtain as a result. We ran naked two floors up and into my bedroom. How much longer we lasted, I’m unsure of. But it was amazing.
The next morning, I cracked open my eyes to look at the young man who was in my bed. I truly had my first cub and first double-take: he was only eighteen.
At the beginning of summer 2013, I had seen a very attractive younger man enter the bar I was dancing at. We had locked eyes a couple of times throughout the night, and I wondered if I had known him. He sidled up to me and asked how I was doing. We both quickly realized who each other was. It was thirteen years after that experience, and he was just as cute. We were both very happy to have met again. I told him he was the best one night stand I’d ever had, thanked him, and continued on.
Cubs: What about your first time with an older woman? We’d love to hear about it in the comments below.