[MF] Rendezvous With a Cougar (39) that I (26) Met Online (with pictures)

This story occurred in early 2016. It involves me meeting up with an older married woman I met through Craigslist for some of the most thrilling sex I have ever had.

I was 26 years old at the time and had just finished grad school and was working at a summer internship with plans to move in a month to start a new job in a different city. My then-girlfriend and I recently broke up over a petty fight and I wasn’t keen on looking for a new relationship, especially with only about a month left before I moved away. However, I did want someone to fool around with, if possible.

It seemed like a long shot, but I created a few posts on Craiglist seeking a no strings attached hookup with each post centered around a different fantasy or activity that turned me on. One of the posts was searching for a woman to watch me masturbate or mutually masturbate together; it has always been a turn on for me to finish in front of a partner. Unsurprisingly, I got myriad responses from bots and dudes. With the sheer volume of “m4w” posts online, I figured I had a snowball’s chance in hell at finding a sane, attractive woman through such a seedy medium. However, fortune was soon to favor me.

I got an email at work one day from what seemed like a real person, or at the very least a bot that could pass the Turing Test or Voight-Kampff Machine. From the initial emails we exchanged I learned that she was a married woman in her late 30’s whose sex life was in a real slump; she and her older husband had a good marriage but he had a heart condition and they hadn’t had sex in nearly a year. To fill this void (no pun intended), she had turned to erotic fiction, porn, and toys. Those things sated her appetite for a time, but she wanted more. The idea stripping down and pleasuring herself in front of a stranger doing similarly was alluring to her. She had never cheated on her husband and that doing something like this was like putting her toe in the Rubicon before deciding whether to ford it or not. From her emails I gleaned that she was nervous and giggly but very turned on by the idea of us meeting up.

To my chagrin, I never learned her name; she always signed off her with “M”. The last time we met she asked if I wanted to know her name and I said no because I had seen something like that in a movie, Last Tango in Paris, and thought it was hot to never even exchange names. For the purposes of this story I will refer to her as Megan because Mildred is a not quite as titilating of a name. Anyways…

We agreed that discretion was paramount and therefore agreed to meet up that weekend at a Starbuck’s inside a nearby department store to ensure that we were both comfortable and that there was physical chemistry between us before potentially heading back to my apartment. In the meantime, we sent sexts throughout the day. Megan sent me pictures that gave me arduous, throbbing erections while at work. https://imgur.com/zryWPwe. I sent her pictures too. https://imgur.com/Gpby22h.

I arrived at the coffee shop Saturday afternoon several minutes early and anxiously waited for her. I had seen her body before, but not her face. Megan told me she would be in blue jeans, a black jacket, and those white converse all-star shoes that came back into style. She kept reiterating that if I didn’t find her attractive we could call the whole thing off, no feelings hurt. This didn’t make much sense because when I saw her walk by there was no doubt in my mind that I found her extremely attractive. She had a toned body from spending her days playing tennis, slightly curly blonde hair, a pretty face, and nervous smile. The next few moments are a blur, but we instantly agreed there was a mutual attraction, exited the store, and Megan followed me back to my place.

The giddiness and sexual tension in the elevator ride up to my apartment were palpable. We worked in the same profession, although Megan retired after she got married. This gave us some icebreaking conversation, but I could tell we were both eager to fool around as soon we got inside. As soon as the door was shut we immediately began kissing and pressing our bodies against one another. We began tearing off each other’s clothing in a frenzied haste. Soon we were both standing in the middle of my apartment completely naked with her nipples protruding like joysticks and my cock throbbing to the point it was almost painful. https://imgur.com/uvXP8UN

I’ve read enough stories on this subreddit to know that this is the part where I humbly shoehorn some mention about my penis being 8” long and, like everyone else who posts here, on the extreme end of the bell curve. I’m not that gifted but at that moment my dick was about an 8 on the Mohs Hardness Scale. https://imgur.com/jeH8Y1J

Our plan was to strip naked and watch each other masturbate. The best laid plans of mine and Megan’s often go awry. Megan grabbed my cock like Lenny holding a puppy, dropped to her knees and sucked me with more force and vigor than I had ever experienced. https://imgur.com/tqUtyze. I exchanged the favor and soon we were on the floor with my head between her legs, my tongue circling her clit, and my fingers massaging inside her. When she came she wrapped her legs around my head and pulled my hair so frantically that it almost caused me to cum as well. https://imgur.com/vgvkgik

It went unspoken, but we both knew that we were going to fuck each other that night. Megan laid back on my couch as I fingered her intensely, wet succulent sounds being made with each stroke. She was dripping from her pussy down to her legs. Whether she acquired it from reading erotic literature, watching porn, or just some innate kink, Megan loved to be called dirty names and for me to say the filthiest things I wanted to do to her. Two weeks prior, I never would’ve imagined there would be a 39-year old woman with a professional degree, completely naked in my apartment, getting fucked by me while I tell her that I wanted to drown her in my cum or that I would turn her into a humidor like Bill Clinton did to Monica Lewinsky. The dirty talk was somewhat uncomfortable and kinda degrading for me do to her, so I tried to couch it in humor.

What happened next shocked me. Megan asked me to film us fucking on my phone; she wanted to be able to watch it again and again. I immediately assented and grabbed my phone. She bent over my couch with her ass sticking up as I pummeled her from behind capturing the sights and sounds of our ecstasy. https://imgur.com/LcoqJAS. We took a breather after we exhausted ourselves. Per Megan’s request, I tied a scarf around her neck and lead this gorgeous naked woman, 13 years older than me, crawling on her hands and knees, towards my bedroom.

Once in bed, we fucked like two horny freshman who had years of pent-up sexual urges that were unfettered and came bursting free. Almost every fantasy Megan had cultivated while reading those god-awful romance novels was explored that night. https://imgur.com/o3GYFIM Megan was euphoric lying on her stomach while I was on top of her, holding her hands down, thrusting inside her, biting her ear, and whispering to her how bad she was for making me so uncontrollably horny all week. https://imgur.com/bv87uLm

I had been edging for what felt like an hour and I finally could not last any longer. I told Megan I was going to cum and she was elated. She asked me to cover her with my cum and I did. Megan laid on her back while I straddled above her stroking myself while looking at her eager face below, her eyes enthralled by my dick. It took only a few seconds of me looking down and her squeezing her boobs together for me to cum. It felt like that scene in The Two Towers when the Ents break the dam at Isengard and release the river. In reality, it wasn’t quite as thematic as that, but her breasts were soon coated by several ropes of my seed. https://imgur.com/A5VQwGU. We were both shuddering with ecstasy before the post-coital relief washed over us. https://imgur.com/QdfbYEz

Reality kicked in and we both quickly cleaned up so she could be on her way home to relieve the babysitter. It may be divisive for someone else to read this, but I didn’t feel pangs of guilt that she was married. I could sympathize with her not having sex in almost a year and it sounded like that part of her otherwise happy marriage had died out. If this was the release she needed to keep things on an even keel, then so be it.

We only met up one other time. It was pretty similar to the first time, and some of the attached pictures are from our second rendezvous. For a few months after I moved town, we would exchange emails and sexts. I would send her the pictures and videos she wanted us to film, we talked about meeting up again, but it never came to fruition. One day I got an error while emailing her notifying me that the account had been deleted. Since I never got her name, I had no way to figure out who she really was to try and discreetly get in touch with her again. Like that, she had vanished into the ether as if Thanos snapped his fingers. I hope you enjoyed this story as it’s one of the few stories I have that might warrant posting to this subreddit!

Source: reddit.com/r/gonewildstories/comments/8wp2b5/mf_rendezvous_with_a_cougar_39_that_i_26_met