I’m 22 when this all happened. We’ll call her Sally.
I was working at a company as the IT guy when all of a sudden I’m introduced to a new hire, Sally. Man…. was Sally fine, blonde older lady looked like she was in her late 30s, my height, amazing D rack, and a nice bubble butt. Was told I had to train her on some software and the usual deal. When that time came, mid training I notice she has a wedding ring on her finger and thought oh well, as if I had a chance right?
Well as we work together I get her number and we start talking. After a couple months I find out Sally isn’t married, she never was. She lived with her kids dad at that moment. Im not sure how but she ended up confiding in me that she hadn’t had sex in months. She even knew the exact amount of days. She was very unhappy and was just there for her kid.
One day during a company event we started talking dirty and I couldn’t believe it. She was sending me nudes and tit pics and all. I kept thinking this is a setup or something is up because there’s no way this older milf is into me and giving me an opportunity.
We end up agreeing that we’d meet at my apartment during our lunch. And we did! Started touching and kissing, and eventually pulled my pants down. As I whip it out I reach into my pocket and turns out I forgot my condoms! She was pissed, gets dressed and leaves. I hated myself so much. But I got a second chance!
She comes back the next day and we go at it again. I was actually prepared this time and she ended up hopping on top of me and rode me like no tomorrow! She was so wet and tight from not getting any dick for months! We ended with her bent over and me busting all inside the condom. It was the best feeling ever! I went to clean up and she gets her knees and shows me how older women suck dick and it was amazing! This was the beginning to something amazing!
Sorry if the formatting is weird or something. This is my first time sharing and have more stories with Sally if interested!
Source: reddit.com/r/gonewildstories/comments/w9ml4p/helped_a_coworker_in_need_mf