Introducing your cougar to friends and family
So, I had met an older woman on one of those free casual dating sites. She saw my profile and started chatting me up. At first I wasn’t really sure what to do. She was definitely attractive looking, going by her pictures. But she was also like 40 and I was in my early 20’s, just out of college.
It was at a time in my life when I had my first real job, and I was working a lot, trying to prove myself and my worth to my employer. It was a lot of overtime, a lot of stress, and not enough sleep. You know, sort of like college, but without the parties, and the four day weekends.
I joined a sex dating site for the hell of it. I wasn’t getting out nearly as much as wanted to, and the bar scene was a lot different than hooking up with girls at parties. At parties, these girls knew you. They were basically part of your social circle or your extended social circle.
Girls in bars were way less friendly. They’d all go with their group of friends and they really never left that circle. They might let you strike up a conversation with them and sometimes you’d even get a number, but more often than not nothing came of that.
Suffice it to say it was a much different scene than I was used to. I was having drinks with some of the guys and girls I worked with, but most of them turned in early, and hooking up with coworkers could get messy. Not that I was against messy in principle, but nothing ever seemed to go anywhere. I had a fling with one of the secretaries but that never went anywhere either.
So free casual dating sites seemed like a good option. Of course, most of them are crippled for non-members so I figured what the hell. I’ll pay for full membership and then see where this goes.
A week passed and I was chatting up girls online and it was working out alright. Met up with a few of them for drinks in the evening and we hooked up and it was just what I needed. But then I got propositioned by an older woman on the site. She was in her late 30s and smoking hot. I couldn’t believe my eyes when I was going through her pictures. Was this lady for real?
She wasn’t super old looking or anything. She looked like a MILF porn star and she had bright blue eyes and a gorgeous smile that lit them up when she looked at you. We got to chatting online and I was nervous, actually, and apprehensive. I could tell that turned her on a little bit. She just kept pushing harder for me to meet her for drinks, and finally I gave in.
I had never thought of myself as someone who would be interested in a cougar and cub relationship but I’ll tell you this. She liked to be the one in control but she didn’t mind getting dirty either. She was absolutely voracious in bed and I really couldn’t get enough of her. We started seeing each other more often and I really liked being with her, but I also felt like it would be awkward to try to explain her to coworkers, friends, and especially my parents. I mean, I was practically addicted to bedding this woman, but beyond that we didn’t share much in common.
Anyway, we were on a date at a popular local restaurant when I saw someone approaching our table. It was my parents. There was a moment of shock where my face must have turned red, but I composed myself quickly and explained my date and I were out for dinner and drinks. When my parents asked where we met, I said coyly that we had met online, and she gracefully shook my father’s and mother’s hand and smiled, somehow avoiding embarrassment. There was a moment of awkward silence, but then Irene, my date began to explain that we had seen each other a few times and really enjoyed one another’s company. My mom seemed completely unphased by any of this, even though I was clearly red in the face. She didn’t do anything silly like invite Irene over for dinner or anything. She could kind of sense that it wasn’t the kind of date where we were going to end up picking out furniture and procreating. My dad kind of looked at me bemusedly, and eventually they cordially told us to have a good evening together and enjoy ourselves.
While it was kind of embarrassing introducing my mother to my date who was only slightly younger than she was, we all got over it quickly and Irene and I went home and fucked. Dating a cougar wasn’t so bad after all.