This happened around 7 years ago. I was just venturing out and starting to look for a FWB to deal with a mostly dead bedroom. I’d placed an ad on Craigslist stating honestly my situation and what I was looking for. I suppose the ad was good, because I actually got a small handful of legitimate responses from the ad from various women in the area who were interested in chatting and seeing if maybe we could work something out. Kassy was one of the replies I got. She told me she was married, no kids, and her husband was a truck driver and gone during the week and only home on weekends. I don’t believe he knew she was seeing other men while he was out of town, but she was pretty open that she wasn’t really looking for just a one time thing, but rather she wanted a boyfriend while her husband was out of town.
I wasn’t specifically looking for a one time thing either, but really wanting to find someone that I could have regular meet ups with. Kassy was a little heavier set, pale skin, red hair and green eyes. She was attractive, yet there was something about her that didn’t quite do it for me. However, we got to talking and hit it off pretty good. It sounded like we were pretty much on the same page for what we were after and it didn’t take too long to determine that we’d like to meet. We decided as a first meet, we’d get together for lunch.
Side Note: A number of my meet ups have occurred over the lunch hour. I find it interesting because often when scheduling meet ups we discuss meeting over lunch…but I always have to clarify if we’re meeting to get food, or just meeting over the lunch hour. In this case, we were meeting for food.
I met her at a local restaurant, one she described as one of her favorites. We had a great lunch, spent some time talking and flirting, but the public nature of it made it a bit difficult to really do much more. We had a nice lunch, and as we finished up I walked her back to her car. I let my nerves get the better of me, and basically told her I’d chat with her later, when what I really wanted was to kiss her. She got in her car and drove away, and I texted her that I was instantly regretting not kissing her and if she’d come back I wouldn’t make that mistake again.
She agreed to return and a few minutes later, we were parked in her car making out. We made out for a little bit, and then I was needing to head back to work. We continued to chat for the rest of that day and quickly decided we needed to schedule another lunch date. This time, just meeting over the lunch hour. We picked a park that wasn’t too far from where I worked and decided to meet there. She told me when I got there just to get in the back of her SUV.
So I arrived, parked beside her and climbed in the back door. She was already in the backseat waiting for me. We got comfortable and started making out again. This time our hands were wandering, I was feeling her up, and she was rubbing my cock through my pants. The kissing and groping continued and soon my hands were under her shirt, her bra unsnapped and I was playing with her tits and teasing her nipples. This continued for a bit before I was undoing her pants. My hand quickly found it’s way under hand pants and down the front of her panties where I found a soaking wet pussy waiting for me.
We made out and I fingered her listening to her moans and feeling her squirm against my touches. After a bit she tells me she’s close and I keep fingering her pushing her over the edge. I listened to her moaning, feeling her pussy contracting as she came. After she gathered herself following her orgasm, she had me lay back and proceeded to unzip my pants. She reached into my pants taking my cock into her hand and began to stoke me. Pretty soon she had my cock pulled out of my fly and had positioned herself on the back seat and lowered her head to my lap. Her mouth felt amazing as she took me in and began to give me head.
I watched as she bobbed her head up and down on my cock, relishing the pleasure of her mouth on my cock. She would occasionally look up and make eye contact with me while she was blowing me and I was nearly losing my mind. My wife rarely gave me head and when she does it was only so-so, but this woman was amazing with her mouth. Pretty soon I could feel my balls tighten and the base of my cock began to tingle. I told her I was about to cum and she didn’t skip a beat at all, she just kept working my cock with her mouth and soon I was gushing into her mouth as she took me over the edge.
Kassy continued to suck on my cock swallowing my entire load. It must have been an amazing orgasm because afterward she stopped to ask me if I was ok. Thinking back on it now, I think this may have been the first time I had a woman let me cum in her mouth, and I was hooked. We continued to mess around for a bit, but neither of us were prepared for having sex that day.
We did talk about sex. At one point she had me sit back against the seat and straddled me giving me a lap dance to see if that angle would work for fucking, and I had her trade me places and she laid back and I ground against her from in front of the seat. We were both turned on and I was hard again and commented ot her that had she been wearing a skirt, I would have been so tempted to pull it out and fuck her raw right then.
We finished up and needed to be getting back to work. The whole time we were hanging out though, I kept having that nagging feeling that while I liked what we were doing, and I liked her well enough, I just wasn’t overly attracted to her. As we continued to chat and began exploring options for meeting up again and having sex, I ended up telling her that I didn’t think I wanted to do that and explained why. She was pissed about it, and felt like I had let her on just to see how much I could get from her. In some ways she was right, but at the same time, had that been the case, I don’t know why I would have stopped things before we started having sex.
Pretty much after that she and I quit talking.
Source: reddit.com/r/gonewildstories/comments/ik69i0/putting_on_the_brakes_mf