Even though it’s been about two years since we last had sex, in a round about way the affair is still alive. We still chat regularly and given the opportunity we’d end up having sex again. Oddly, she has been my longest sexual partner, and I guess emotional relationship.
I have no intention of breaking up their marriage, I never had. I care too much for both of them to do so. I also have a feeling that my buddy knows as well. We just never talk about it.
He and I used to work together; he started at the same company I was at about two years after I did, so I was tasked with training him. We hit it off and that first day after service we had a beer after wards. Talked sports, the job and everything else. He had just married about 6 weeks earlier, his high school sweetheart.
Over the years we would hang out more and more each time, celebrated milestone birthdays, and milestones in general. Every time getting closer and closer as friends, and confiding more in each other.
I have always had an exhibitionist streak, and as time went by discussing sex became natural. Not part of every conversation, but definitely not out of the norm.
It was a night where him and I were shooting some pool and just discussing plans for our futures, etc. My ex had been out with friends, but her evening got cut short but she wasn’t ready to head home. She texted to say she was joining us, not an issue. Of course she was dressed to be out with friends, wearing a zip up dress that showed her figure, and was a dangerously short for pool, but great for getting free drinks at any bar.
My ex went to get a round of drinks and my buddy commented on her looks, it was the first time he did something like that, but her dress, plus the alcohol made it roll off his tongue. Honestly, I didn’t care and I agreed with him. When he went to the restroom, I told her what he had said. She took this as an opportunity to flaunt her ass when she was up to shoot. She later mentioned that she wasn’t aware that the bottom of her ass was showing, and we could also see her thong from our angle (we were seated slightly below the pool table, so our line of sight was looking up to her). As the night wound down and we were walking out, my ex was walking slightly in front of us, and I took the opportunity to smack her in the ass. He took this as an invitation and smoked her other side. My ex and I got home, and immediately began to make out, fucking her on the couch, just pulling her panties to the side and cumming on her dress.
Next day my buddy was apologetic, blaming the alcohol, etc. I told him not to worry, and that as far as I knew, my ex was cool with it. One thing my buddy was not aware of was that my ex, whom I had known since high school but only started dating a few years later (at this time we were 24 or so and we had been dating for a couple of years. We weren’t living together, but she spent most time at my place if I wasn’t at work), had been involved in a couple of threesomes. Both spontaneous, both with friends from her university.
Over the next few months my ex would try to initiate something, often suggesting spin the bottle or strip poker when we were all together. I could tell that my buddy hadn’t told his wife because he would always nervously chuckle. Eventually my ex gave up trying and we went life as normal
The box was open a few months later. Finals prevented my ex from coming out to celebrate a co workers birthday, but my buddy and his wife were both there. She was sitting on his lap and they were enough out of the way that she could grind on him and give him a private grind while in a crowded bar. I caught a glimpse of them and raised my beer to him, giving him a thumbs up of sorts. He waved me over, and she kept slowly and sensually grinding on him. Music was loud, so I had to lean over to hear him. Her face was maybe two inches away from me, and we looked at each other while I leaned in to listed to my buddy.
“I want you to kiss my wife”‘ he said. Not demanding, but asking…
I asked him if he was sure, he said he was. I asked her if she was ok with it and she said she was. It was a light kiss, a peck with some lip nibbling, nothing too involved. It was a little awkward as she was still sitting on his lap, but it was also tender.
The rest of the night went as they normally go, and on the way out the bar I checked with my buddy, making sure he was all good. He assured me he was.
Over the next year or so nothing happened, I started noticing her more when we went out. She is very undertone sexy. Not exotic by any means, but still a good looking woman. She’s 5’4”, light brown skin, brown eyes, long black hair (down to her waist), B sized perky always hard nipples breast, with toned legs and a nice round ass. She also wore dresses a lot, which I always found very sexy. By now they had a kid, so she carried a little extra padding, but she was far from fat.
I came home from work one night, and at the time I was taking an online class so I signed on to work on whatever assignment I was working on, and I noticed that she was logged into messenger. She sent a message, something to do with burning the midnight oil, etc. I commented the same for her. She was working on some project or something. We chatted about life and what not, and how lately she hadn’t been out much. With their kid and no one else in town it was difficult, etc. The next day I logged on again, and there she was. This became a nightly thing, which later I found out we were both looking forward to. My class didn’t really demand that much attention and her project had been completed for sometime. Also, at this time my buddy had picked up partying a little harder than I cared to keep up with, so she was often alone at night for a few hours. We eventually moved the chats to text, during times I knew my buddy was at work and we always seemed to have something to do when it was getting close to him coming home.
The fortune would have the four of us out celebrating a birthday and both of our ladies were dressed to the nines. Short dresses, heels, the works. We ended up in a neighborhood bar and the crowd was already winding down. We picked a table off the general floor and we continued to chat. We knew about our private chats, but tried to act as if we were catching up. With a few on him, my buddy asked if he could kiss my ex to which we both agreed. After they exchanged a kiss and his hands wondered onto my ex’s breast (she is a DD, natural and at this time still very well in their place). I asked him if it was ok if I did the same with his wife. He said yes as long as everyone was cool. We had been waiting for this opportunity and here it was. We tried not to over do it, so we kept it semi brief. When we broke away from each other we noticed that my buddy and my ex were full on making out. He was trying to grab her breast, but her dress was too tight up top, and she was rubbing him over his pants. We took this as a sign that it was ok to do the same, so as she sat at the bar stool, I spread her legs and continued to kiss her, while running my hand up her dress and rubbing the outline of her pussy with the back of my hand.
A server caught our attention so we all broke it off. I had to go to use the restroom and so did she (we did not plan it and nothing happened), but when we came back he was gone. My ex said that they had returned to making out, he stopped and walked off. We all assumed he had gotten cold feet and was upset. We drove her to their house, it was an awkward drive as we all apologized to each other.
On the drive home, my ex told me that she though he had came while she was rubbing him thru his pants. I didn’t really thought that was the case, we went home and fucked as soon as we walked in.
Next day I called him over and over, he finally texted me, said he remembered very little and that he was cool. He started avoiding my ex, unless he had been drinking, etc.
The next time I texted her she said that he was fine, but it was probably best we stopped our chat sessions. I asked her why, to this point they had been flirtatious, but nothing direct or that we couldn’t explain away. She said that “we knew what we were doing…” Rather than playing stupid I asked her, if we could guarantee that no one would know, would she want to go further? Up to this point she had been shy-ish and coy, but after some back and forth she admitted she would.
Over the next few weeks we discussed how to make it happen and we finally settled on meeting at a hotel. We had four hours and we used every single last minute.
When she walked in she was wearing a green tunic dress and golden gladiator sandals. We kissed and I ran my hands under her dress to find her bare ass. I removed her dress to find a matching pair of leopard print bra and thong panties.
I took my time exploring her body, kissing down her neck as my hands explored her body. I took off her bra, but purposely left on her panties. My mouth eventually found its way there and I kissed along the panty line, eventually slipping a finger under her panties to flick her clit. Hooked my finger around her panties and pulled them down. There she slayed, naked except for the bracelets she was wearing and her wedding ring. I was still dressed at this point, so I removed my shirt and pants, my dick was already semi hard, so I motioned for her to help me with my underwear. She was perceptive to being given direction, and as my semi hard dick sprung out she gasped a little. I pushed her back onto the bed and resumed kissing up my way to her wet pussy with it’s dark patch landing strip just above her pussy lips.
I ate her out for a while, playing with her breast while I did so. She later complimented me on my pussy eating skill.
I kneeled between her legs, asking rubbing my dick against her pussy lips and her clit. I asked her if she was sure, she said yes. We had already discussed that I would have to wear a condom as she wasn’t on the pill, so I rolled one on. I told her that I needed her to guide me into her to be sure. She reached out with her right hand to grab my hard dick but I grabbed a hold of it and pressed it against her soft stomach. She had to use her left hand. Nothing was spoken, but the sight of her hand with her wedding ring on it holding my hard dick was something else. I leaned forward and let her guide me in. We did it missionary that first time, adjusting to each other. Her tight pussy wrapping around my dick, kissing and me feeling up her body. As I felt getting close, I pulled out to buy time and went to eating her out again. After a while, she mentioned that she had a really hard time getting off and would always take things into her own hands. I knew what I had to do.
After we made out for a little longer, and I felt like I was ready I asked her if we could try something. She said anything. I position the sofa chair to look at the floor to ceiling window in the hotel, I asked her to sit on my lap, reverse cowgirl with her feet on my knees. She had never tried this position. As she worked herself up and down I reached around and played with her clit and pussy lips. Not two minutes later she dug her nails into my legs and had her first orgasm with a guy. It turns out my buddy had been not the most attentive to her needs.
I kept edging myself, preventing myself form cumming that night. Like I said we used every minute of the four hours I had her for. I did not cum that day, not with her anyway. But it was a worthy investment.
Source: reddit.com/r/gonewildstories/comments/tyd0ax/the_start_of_a_10_year_affair_mf_very_long
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