Author: runnerCO

[M]y [F]irst time fucking my Co-Worker

So this happened around the same time as my first story post here. I’m 24, living in Boston, and on my first serious job after college. 

For the first six months of knowing this girl, we were kinda flirty buddies at work. Talked open about our personal lives, dating, failed dates, etc. We did a ton of activities that would make you think I was friend zoned, but I think that was part of her attraction to me. She was a cute girl and I didn’t get bottled up around her. 

She was also in long distance relationships. Kinda off and on from the time i knew her. When this first encounter happened, I think she had been single for about a month or two, so it kinda made sense something was building up. 

Anyways, here’s how it happened. 

It’s her 24th birthday and a bunch of coworkers go out for drinks to celebrate. She picks the spot and it’s close to her place. I live in a different part of the city, but not more than a 15min cab ride.  Read more »

[M]y [F]irst time with an “older” lady.

This was my first encounter with a cougar back when I was 22. I was in college, the middle of my senior year, and I was fresh out of a LD relationship. 

For my last year of college I decided to skip the roommate thing, so I lived alone. Kinda near the downtown area where all the best bars are. 

Anyways, it’s starts around midnight. I’m walking home from the bars alone. On my walk home I stop off in a good drunk food spot. As I entered, I noticed a group of giggling women. I can tell they aren’t college kids, but it’s not like they are my moms age. I’m guessing early 30s.

As I get my food and walk out, one of them follows me and starts to chat. She’s cute. A little thick, curly hair, tan, and def a bit older. I can tell she’s had a few too, but I dont care. So did I and we are drunk flirting. She asks “arent ya gonna eat that” and I say that I am, my place is just 2 blocks away. Before I can finish, she asks if I have anything to drink. I say I do and she invites herself over.  Read more »

[M]y second time with cougar [F]

This is a success story from a few years back. It was my second time with a cougar, but it was the largest age difference. 

I’m not much of a writer so bear with me. 

I was 24 and living in Boston. I was single and living alone and decided to give OK Cupid a shot. After a few days of no success, i changed the age range to 40-60. I’ve always been into older women. My first experience was when I was in college and i was hooked. 

Anyways, I started to get a few matches and there was one woman who i really hit it off with. We chatted for a bit and exchanged numbers. She was in her lower 50s. Short hair, in average shape. She sent me a hot bathing suit photo showing off her large breasts. 

We realized we lived in the same neighborhood and thats how things got fast tracked. She asked if I wanted to come over for some drinks and maybe some weed – but i knew what she was really asking. So she asked me if I wanted to call her to get directions, so i did. I was trembling as the phone rang. Then i heard her voice. It was such a turn on. She told me to come over in an hour, so quickly got ready.  Read more »