Most of my cheating experiences were one night stands, women I met on business trips and only saw one time. I have had a few affair partners though. This is the story of one of my local affair partners.
We met on the app Whisper, which truly is a horrible app for many reasons, but it does sometimes work for meeting people. She posted a completely innocent message in the local feed, and I responded. Honestly I don’t even remember what she posted, or how I responded, but we had a very normal non-sexual conversation. She even remarked about how it was unusual for a conversation to keep going without it getting sexual. We had talked about how she was engaged, how I was married, how I was an old man to her (I was 35, she was 23), work, school, my kids, and so on.
We kept chatting, now via Kik, for a few weeks. It took us a while, but we finally exchanged pictures, and she was stunning. A beautiful latina woman, smooth skin, eyes that penetrated your soul. I’m not bad I suppose, but she was a step above my league for sure. She didn’t seem to feel that way though, she got flirty after exchanging pictures. Still, neither of us even suggested anything out of bounds. Yet.
We were chatting one day on Kik, and I could tell she was upset. I asked what’s wrong, and she said her fiance shared a video of her with his friends and she was upset about it. I asked what the video was, and unexpectedly she sent the video – and it was of her sucking his dick and him cumming on her tits. I was shocked for a number of reasons.
First, I consoled her since she was obviously upset. Second, I commented on how her breasts were stunning and matched her overall beauty. Third, her fiance had a small dick, haha. She seemed to enjoy me saying the last part and accused me of looking at too many dicks if I knew he was small. I responded that I’m just comparing him to myself, to which she challenged me to prove it. So I ducked into a bathroom at work, got myself hard, and sent her a pic. She acknowledged I was indeed bigger. I let her know she was welcome to find out in person, but she said she wasn’t a cheater (she knew I had a history of cheating but didn’t hold it against me).
A few days go by, and she admitted to me she masturbated to my dick pic, which turned me on, but she still didn’t want to cheat. I gave her the corny line “eating ain’t cheating and sucking ain’t fucking”. It took her a while to respond, but finally said “well…Mike (her fiance) just left and won’t be home for a while…” I got her address and told my boss I had to run an errand. He didn’t bat an eye.
I knocked on her door and she opened right away. She was shorter than I expected, barely 5 feet tall, but she was even more beautiful in person. She admitted she was nervous, so we chatted for a few minutes to get a better feel for each other. Finally, during a lul in the conversation, I asked if she was ready – and she was. I kissed her, and she lead me to the extra bedroom. We stood and made out, and I groped her sexy body. Her tits were firm, her ass tight. We undressed, and my cock stood at attention for her. She grabbed it and stroked me, then sat down on the bed, laid back, and spread her legs. I didn’t say anything, I simply knelt down on the floor and went to town on her. She was so tight, I could barely fit two fingers in her pussy. I spread her lips and started slow on her clit, all while fingering her and seeking ways to drive her to the edge. It didn’t take long for her to arch her back and moan loudly, then she started to buck on the bed and pull on her nipples while I was focusing on her clit. Her moans let me to believe she was about to cum, and I was right. Her orgasm shook her body, and I could taste the rush of wetness on my mouth.
She fell to the bed and relaxed her body. I stood up, laid down next to her, caressed her tit, and kissed her. She grabed my cock again, then leaned down to suck me off. Her tiny mouth had trouble swallowing all of me, but she focused on my head and used her hands like an expert. She looked up at me, and at that point her eyes piercing me drove me over the edge and I blew my load down the back of her throat.
We laid on the bed, touching and caressing each other, sarcastically talking about how this wasn’t cheating, even though neither of us believed it. She notcied I was getting hard again and asked “are you still horny?”. “of course!” I answered, then she got on her hands and knees and presented her pussy for me and said “then fuck me!” She didn’t have to ask me twice. I pressed my cock against her tight hole and slowly entered her. She was so tight, I almost came immediately, but was able to control myself. I slowly entered and exited her pussy, making her cunt looser and looser with every slow pump. I started to go faster and grabbed a hold of her hair, giving her a firm tug, which she loved. I pulled her into me by her head and heard her gasping with pleasure. I picked up speed and really started fucking her now, one hand on her hip and one with a handful of her beautiful silky black hair. She yelled as she was cumming again, and I wasn’t far behind. I felt her tight pussy clamp around my cock, and that was it for me, I emptied my balls inside her (don’t worry, I had a vasectomy).
We laid down again, and I said “ok, THAT was cheating” which she found to be hilarious. She just breathed deep and said “it sure as fuck was!” I got dressed and headed back to work.
After this, I would come over once or twice a week when there was no danger of getting caught by her fiance. She conveniently lived 5 minutes from my office. Eventually they did get married, and at that point she cut off our affair, though we did keep in touch via kik for a while. She moved to Boston shortly after she got married, and I haven’t been in touch in a good while now, but it certainly was an affair to remember.
Source: reddit.com/r/gonewildstories/comments/al7y8j/mf_sexy_young_local_fwb
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