Amanda | Emily | Rachel | Sonjya | Melissa

I figured I had one last good story to share from those LDR days. Most of my encounters with women were one-night stands that we both talked about before going into them. This one-night stand was different because of the unique circumstances. I still think about it to this day from time to time.

I met Jennifer over Craigslist Personals. She was from the same town I grew up in, which provided a nice connection. She knew I was in an LDR. She had that thicc, curvy body that always works like magic on me. She was married with two kids. Her husband, however, was a drunk, and she shared that he wouldn’t get physical with her or her kids but just be a jerk and break stuff around the house. I empathized with her. She didn’t deserve that sort of behavior, especially around her kids. Jennifer also happened to work in the city I lived in at the time, which was just a few minutes away from my place. We talked a lot, and there was a lot of teasing, but I didn’t want to pressure her, and she was fun just to text with.

One afternoon, she messaged me and said her husband was probably getting drunk that night. She wanted to avoid the headache and was dropping her kids off at a nearby family member. She also gathered what she didn’t want him trashing, especially her acoustic guitar. Then Jennifer asked if she could crash at my place that night. I told her that was perfectly fine, I didn’t think she should have to put up with his shit. I also told her there was no pressure for sex at all. If she needed a good night’s sleep, I’d ensure she got that. Her peace & safety was key.

Jennifer arrived, our first in-person meeting. We had that moment where we hugged and then, while pulling away, caught each other’s eyes and felt it. We kissed. Nothing prolonged or sloppy. Just a soft peck on the lips. We spent the evening hanging out, watching TV, and talking. My main goal was to keep the conversation away from the stress in her life. It was getting late, and she had to work the next morning. I told her I would sleep on the couch, and she could have my bed. Jennifer didn’t miss a beat and said, “I don’t want to be in bed alone.”

She undressed down to a tank top and panties. I was down to my boxers. We lay there talking while pressed close, her thigh draped over my hip. I remember the only light came from the street outside, cutting through the blinds and making a striped pattern on the wall. Jennifer’s skin felt so good against mine, warm & soft. Eventually, we started kissing again. This time, they were much more passionate, lingering, and hungry. I held her ass and pressed myself harder between her thighs. She couldn’t miss how I felt about being in this bed with her. 

Clothes came completely off at this point, tossed to the end of the bed, and some fell onto the floor. My hand played between Jennifer's thighs. I loved how she would gasp when the pleasure on her clit became too much. I tried to go down on her, but she said she didn’t want that. I love eating a girl out, but I don’t push it if she says she doesn’t want it. I told her I could get a condom. She said, “You don’t need to. I have an IUD.”

And that’s the first time I slid my cock into a married woman’s pussy. Jennifer was the first woman I was with that really knew how to work her pussy. I could feel her flexing those muscles on me as I stroked inside. I even told her that her pussy felt incredible, that I could feel her clenching me. She smiled, and I felt her do it even more, working her hips with mine. She had beautiful D cups that jiggled as we worked our bodies back and forth. What I remember most is how fucking great she felt. It wasn’t sportfucking; it was two people just enjoying each other’s company, bodies, and pleasure. 

She came good and hard on me, that beautiful clenching pussy letting me know it. That made me give in, pumping thick warm ropes inside her, my cock twitching as it unloaded everything I had. We stayed like that for a while, me still inside her. She told me she could feel my heartbeat in my cock; it was definitely pulsing. I leaned down and kissed her, which kept me hard, and in one of those rare moments in my life, I never went soft. I softened but got hard again, and we started right back where we started, chasing the next orgasm.

Eventually, we had to sleep. I woke up early. Jennifer laid on her side with her back to me. I kissed her shoulder and just let my hand caress her legs, hips, stomach, and shoulder. She woke up with a satisfied mmm and a soft “Good morning,” I knew her husband probably wasn’t tender with her, but I wanted to ensure I was. We kissed but were interrupted by one of her friends calling her. She made up a story about crashing at a co-worker’s house. The friend apparently knew about the drunk hubby. I teased her pussy while she was on the phone. I think she simultaneously hated it but didn’t want me to stop. I tried to take my hand away after she gave me a look, but Jennifer put hers over mine to make sure I didn’t remove it.

Once she was off the phone, we fucked again. I wanted her to feel my inside for the rest of the day, slowly dripping out. After I put this third load inside her, our time was up. I got dressed with her to walk her out to her car. She got in and leaned down to her open driver’s side window, giving her a long, deep kiss. Touched her cheek and stepped back. She was smiling as she drove away. But this is a one-night stand, after all.

We kept texting for another month, but I got the vibe she was feeling guilty. One of the byproducts of growing up in an evangelical area of the country. Even if you aren’t a true believer, there’s an ambient social pressure to follow their rules. I made sure she knew my place was open to her if she needed another night away. But then the messages thinned out, and we both got busy with our lives.

I’ve been thinking back, and I might have one or two more worth sharing that aren't cheating stories, but I want to mull those over to see how much I remember.