As I was typing up my last story I remembered another time that I nearly got caught in the back of a vehicle. This story took place maybe 7 or 8 years ago. I was at a point in my marriage where I was really frustrated sexually and had decided I was going to actively look for a Friend With Benefits. I posted an add on Craigslist and basically laid it all out there. Explained my situation, what I was looking for, why I was looking, etc. I got a few hits from that add, and Karli was one of them.
Karli lived in the town just south of where I lived. Her situation was that she was married, but her husband worked a job where he was out of town a lot. While their marriage wasn’t open, she was interested in a boyfriend on the side. I wasn’t exactly looking for a girlfriend, but I wasn’t opposed to this being more than just sex. We chatted off an on for a week or two and had a number of dirty chats in addition to just getting to know each other better. I was enjoying the conversation and the potential sexual partner, but wasn’t entirely convinced I was really into her. We decided we’d like to meet and visit in person and see how that goes, and of course both agreed you can learn a lot from a kiss.
We made plans to meet at a restaurant for lunch one day and see how it goes. While I’m really chatty online, in person, I tend to be much more reserved and a bit of an introvert. I also hesitate to make the first move unless I know the move is welcome. We had a nice lunch, spent a lot of time visiting and talking more about what each of us were looking for, etc. Eventually, our time was running out and I needed to be getting back to work. I walked her back to her SUV, we said goodbye and she got in and drove away.
Immediately I regretted that I hadn’t kissed her. I quickly texted her and told her I’d enjoyed lunch, and added that I had really wanted to get that first kiss, but let my nerves get the better of me. I chimed in that I’d love a second chance if she were willing to come back and let me try again.
She agreed, and a few moments later she was pulling up beside me and I climbed into her SUV in the passenger seat. I leaned over and kissed her. The kiss was warm and sensual and it felt so electric kissing another woman for the first time in a long time. We made out, our tongues dancing and my hands may have done a little bit of exploring as well. It didn’t last long though, because I really did need to get back to work. We parted ways and continued texting, and while we both indicated we were interested in seeing each other again, I was still struggling how into her I really was.
In discussing a second meet up, Karli suggested that this time we meet over the lunch hour, but skip lunch. We weren’t quite ready yet to have sex, but figured a longer time together would be enjoyable and give us an opportunity to explore more. We made arrangements to meet up at a park in town that we figured would be pretty low traffic. Even if it weren’t her SUV had limo tint in the back and didn’t think we’d have any problems.
We met up and she invited me to join her in the back of her SUV, so I climbed in the side door, and joined her on the bench seat in the back. We were both wearing t-shirts and jeans and quickly we were locked in an embrace as we began making out. We were kissing, and my hands were definitely exploring this time. They were running up and down her sides, caressing her back, and eventually my hand made it’s way under her shirt playing with her breast.
About this time we noticed a police office pull into the parking lot where we were at. We both sat up, but continued visiting. The officer drove over to where our vehicles were and sat there for a minute. I’m not sure if they could see anything through the rear window or not. If they could, it was clear we weren’t doing anything at that moment, or maybe they couldn’t see anything and decided to move on. After they left, we went back to making our and my hands were quickly under her shirt again. This time her bra was unclasped, and my hands made their way under her bra feeling her breasts and nipples against the flesh of my hands.
My expedition continued and soon I was undoing the button and zipper on her jeans and slipping a hand down the front of her panties. She was soaking wet and my fingers glided so easily over her clit and into her pussy. I worked her pussy over with my hand as we made out and it wasn’t long before she was telling me that she was cumming. Her moans sounded so good in that moment. She stopped kissing me and pushed my chest indicating she wanted me to lean back. I leaned back against the armrest and watched as she opened my jeans and fished my cock out. She stroked me for a few moments before lowering her head to my lap and taking me into her mouth.
I was in heaven. Her mouth felt so warm around my cock and the sensation of her stroking me with her mouth as she also stroked my shaft with her hand was incredible. I watched as this married woman bobbed her head up and down, my cock disappearing between her lips. I couldn’t hold it for too long and soon I was telling her I was close to cumming. She didn’t skip a beat, just kept the rhythm up and soon my cock was pulsing as my cum spilled into her mouth.
Her mouth never left my cock and she worked me over until I had stopped pulsing. I must have had quite the reaction because when she finally stopped, she asked if I was alright. I just stammered about how amazing the blowjob was. We both straightened back up and went back to chatting and making out. It was getting close to time for me to head back to work and Karli told me she wasn’t to try something. She had me move to the center of the seat, and then climbed onto my lap, straddling me. We made out like that and she was grinding on my lap and I was starting to get hard again. She didn’t do this for long, and climbed off of me, telling me she just wanted to make sure if worked for next time.
I suggested another possible position, and had her move into the middle of the seat. I knelt on the floor in front of her spreading her legs and moved in close to her. We were making out and I was grinding my hard cock directly against her through our clothes. There’s no way she couldn’t feel how hard I was in that moment and I told her if she had been wearing a skirt, I’d be inside of her right then.
We fooled around just a little bit more before I really had to leave. We went our separate ways and despite how good it felt to fool around the attraction still wasn’t quite where I wanted it to be. I struggled with what to do. In some ways everything was going fine, and our conversations were leading toward another meetup, and Karli told me she’d definitely wear a skirt the next time. The opportunity was there, all I needed to do was agree to meet her again and we’d spend another lunch break together, this time fucking each other’s brains out. I decided that wasn’t the right thing to do, and had a hard conversation with her about how I was feeling.
Needless to say that third meet up never happened.
Source: reddit.com/r/gonewildstories/comments/mfdxyg/a_potential_fwb_mf