During and after college, I worked at my neighborhood supermarket. After I graduated, it was a much more miserable experience, but you bond quickly with other employees. One of which, was a middle aged single mom that had some similar interests as me. Those interests included sex.
Off the bat, she wasn’t a cougar. Pear shaped body with a sizeable ass, not bad looking, but not exactly pretty either. She was about 17 years older than me. We shared a love of science fiction and fantasy, so we had that go on when we had smoke breaks together. She also had a really blasé attitude towards sex, and would speak casually about it when brought up.
Eventually, I got a new job, and I promised I’d keep in contact with everyone, which was a lie. She friended me on Facebook, and said to hit her up some time. She then would message me randomly, and it became apparent quickly she wanted to fuck. I always had a thing for older women, and it had been a while, so I thought, hey, why not.
Our schedules eventually fit, and I went to her apartment. She was sharing a place with her dad; he and her son had a room each, while she slept on the pull out couch. We talked for a bit, then started making out. Hands started roaming, clothes came off, and we took turns giving each other oral. I started; she had some stubble down there, which I like. She was really dominant; she pretty much fucked my face. After that, she took my cock, which she had been stroking before, and without teasing it, took it all the way down her throat to the hilt and started sucking. Then, pretty much 10 seconds before I came, the doorbell rang. She went to pick her head up, but I was too far-gone and pushed it down, pleading with her to let me finish. She moaned something that sounded like ok, as I came, the doorbell rang again. We got dressed in a hurry; she answered the door for her sister. I’ve forgotten why she was there, but it seemed like her showing up wasn’t that uncommon. She didn’t take the hint either, you’d think she’d figure out what was going on, the place was too small for us not to have quickly answered the door immediately, there was a big age gap, and most damning, the whole place smelled like pussy. Still, she was going on about this and that, and it became apparent I wasn’t going to have sex. Disappointed, but satisfied to a degree, I went to leave; she walked me to the car. She was bitching about the situation, but we agreed to meet sometime soon.
That didn’t really happen, however. Our schedules were so opposite of one another; the only way we really found a time to make it work was me taking a random day off. Neither of us could get an empty house, so we ended up renting a cheap motel. She pretended she was a hooker when I went to the front desk. They didn’t seem to care; it felt like they saw a lot of that.
We go in the room, make small talk, and start taking off our shoes. We start getting into it, but she shuts me down and says: I’m not on birth control, so either use a condom or pull out. You can cum anywhere on my body except in my hair. If you’re goanna cum on my face, try not to get it in my eyes.” I had never cum on anyone’s face; her seeming ok with it got me that much more excited.
It wasn’t long before we were both naked, genitals in each other’s mouths. Again, she was very forceful, both giving and receiving, she pulled me tight when going down on her, and used a bit more teeth than I would have liked while blowing me, maybe payback for forcing her to swallow before? I eventually put on a condom and fucked her from behind. Now, I don’t know why, but it turned into angry sex quickly. There was hair pulling, biting, scratching, and overall aggressiveness. It was a blast; I never usually got to fuck so intensely. We shifted to her riding me, she grinded on my cock, and finally, I busted with an intensity that felt like a gun going off. It looked like she had gotten off too, her nails were dug deep into my shoulders, and her face had that eyes rolling in the back of her head, mouth agape look. She dismounted, we lay there for a while, lamenting the fact that we couldn’t smoke inside. It wasn’t long before I was hard again, and we continued fucking.
The third time around, I didn’t have a condom on, instead opting to pull out. I was stoked I was going to get to cum on her face, and finally relished the opportunity I thought only happened in porn. Unfortunately not having done this before, I forgot that you couldn’t really control the direction and flow of semen, it kind of goes where it wants. She was lying on her back, I was aiming lower as to not get her eyes, and I was looking to get her cheeks and lips. The first load hit her right on the openings in her nose, instinctively; she breathed in, and inadvertently snorted. She then coughed and sat up real quick, but I was still going, and another shot hit her right on her left eye. She let out a small scream, and lied back down, cursing and coughing. I felt terrible, and get her some tissues, and went to fill up a cup of water from the bathroom sink. At the same time, some dark, evil part of me was thinking it was like hitting the 100-point hole in ski ball, although I obviously didn’t voice that part aloud. She was wiping up, trying to clear her throat, and yelling at me at the same time. She needed a cigarette, so we got dressed and went outside. Nicotine fit subsided; she said she’s pretty sure those were the last holes on her body to be deflowered. I was surprised the ears had been done before, when I asked; she said I wasn’t the only guy with terrible aim. We traded stories a bit, eventually realizing no one had cum in her bellybutton directly before. Knowing what had to be done, after our final tryst, I pulled out and unloaded in the middle of her stomach, hitting her bellybutton. She laughed, yelled seriously? As I lay down beside her. With only about 45 minutes left, we took a shower. No sex, just some making out and cleaning off.
We got dressed, I dropped her off, and unfortunately, that was the first and only time we hooked up. Our schedules were just too different, we tried, but we couldn’t get anything going, and eventually she got a more long-term boyfriend. We kept in contact for a bit, and we’re still friends on Facebook, but that shipped sailed. If only we had more time, there could have been more get togethers, but for what we had, it was a lot of fun.
Source: reddit.com/r/gonewildstories/comments/59putu/mf_sex_with_older_former_coworker
That was a great story! Ahhh, at least you’ll have the memories.