The time a Cougar taught me anal sex [M][F]

There’s something exhilarating about meeting a stranger for intimacy. I’m not insinuating that the connotation reflects outright debauchery, but my cock always stirs at the thought of becoming acquainted with the newness. I had been using Tinder on/off for a few years, but for the most part, to no avail. I’d fallen into the typical trap of seeing the same ladies on the online dating app, but unfortunately, used the device as more of a way to pass the time as opposed to landing critical hits. I came to understand that my awkward, goofy attitude just didn’t compute into Tinder’s algorithm the way I had hoped it would. Let’s face it: I loved posting pictures of my cat and I, I was still in school trying to finish my second degree, and my hobbies included video games, playing guitar, and Magic: the Gathering. I stood 5’ 10” on a good day, topped with a mop of hair, the color of which was a cross between blonde and brunette as if they had gotten into a street brawl and my color was the messy aftermath, and I had packed on some pounds after discovering craft beer tasted very good. I still had my wide shouldered frame but had a slight pudge above my waist that hadn’t existed 2 years prior. To wrap up my background, I was single at the time of this story, and had been for close to 2 years. Coincidence lent heavily against me, no pun intended.

I had always had an incredible fascination with older woman. I had dared to try reaching out through various ads on Craigslist prior to Tinder, which had marginal success. No matter what digital platform you use these days, I feel as though a large amount of connecting depends on luck and comfort. If I had a feeling I was not connecting with another, there was no chance I thought I’d be able to in person. Strange as it sounds, I prefer to interact via physical appearance rather than direct message. I learned growing up that my way of attracting potential partners was not from my speech, but everything else. At heart, I’m a goofball who loved to show my affections through nonverbal means, especially physical touch. To my dismay as I aged, slowly but surely, the world around me grew to accept a new form of communication that involved punching letters together to string a word and send it to a satellite. The fickleness of it all led me to believe I had been blessed by the graces of heaven, hell, whatever you want to believe in, the day I matched with her.

Her name was Elizabeth. It was a Monday night, and I was on second shift that day, essentially 3-11pm. It was about 8pm, and I had some down time, so I thought what the hell? Let’s message her to see if she really was her age. I started with a corny pickup line, something light hearted and funny, though the exact message escapes me at the moment. Almost immediately I got a response back from her, but there was a hint of sexuality laced in her words. I decided I was young (23 at the time) and the opportunity to flirt with her was hanging like fruit from the tree of knowledge; I couldn’t resist the temptation. Her wit matched my humor, and we were off to the races. Within 4 messages back and forth, we had exchanged phone numbers and agreed to make plans to meet the next night. Unfortunately for me, I worked until 11pm once again the following day. Let me tell you, the next 24 hours was torture, but luck favors the patient (instead of bold), and soon enough I was clocking out and driving to the hotel she was staying at.

While I was driving to her rendezvous, let me fill in the details about Elizabeth. She was 48 years old, stood about 5’3”, nice B cup breasts, a cute butt, brunette hair just past her shoulders, and had gone through a divorce with her former wife a year or two prior. They had shared custody of two girls. In short, not only was my attractive Tinder match a milf, but she was an openly bisexual milf. I arrived at her location after breaking a few speeding laws, but paused before opening my car door in the parking lot. Was I about to go through with this? Yes, with one final conviction, yes I was.

I got out of my car, and nearly ran up to the elevator once inside. Elizabeth had given me the room number she was staying in, and I just about stormed down her hallway in pursuit of her threshold. I knocked politely at her door, and she greeted me coyly with a glass of wine in her hand. She was wearing a robe after a long day at the conference, but once we locked eyes, energy seemed to flow between us. We greeted each other and that was the most conversation we had for the next 15 minutes. I set her glass down and took her small frame in my arms. She was mine, and she knew it. Our lips found each other like the plus and minus ends of two magnets, and we barely left room to breathe. We were primal, each needing more and more of the other until we reached a point of emotional climax mirrored by our bodies entwined in the entryway. Thankfully, we had the wherewithal to close the door prior to our start; my apologies for you voyeur types. I had her in my arms, pinned against the wall, and with each breath, inched further down to her panties. She had on her robe, and underneath, a loose night shirt and boy shorts. On my first journey down to her nethers, I tugged at her boy shorts aggressively to expose the cutest puffed out pussy I had ever seen. Her moans invited me to explore her every inch of labia, every inch of her sex, in an effort to enjoy her first cub experience. She was not ashamed of exclaiming her pleasure during our lovemaking.

My tongue teased at her slit, gliding back and forth across which was met with shivers across her body as a result. Elizabeth was a very toned and petite woman, much thinner than my typical average. She quivered as I began to circle the tip of my tongue around her clit, shouting for me to go faster and not let up. Her urgency made me quite excited, and the heat of her sex radiated from pussy unto my face. I kept thinking I had died and gone to my hedonistic heaven the way Elizabeth reacted to my efforts. Her juices tasted like nectar of the gods and intermixed with my own spit to create a very wet pussy. I had to fuck her.

We moved away from the door and tried having sex with her leaning over a counter. Despite the sexual atmosphere, I couldn’t quite get the angle right whatsoever. (oh yeah, for those interested, I’m about 7 ½ inches long, and look similar to the picture on the back of trojan ecstasy condoms if you need a visual). I have had positioning problems in the past, and don’t have any shame admitting that. After a few unsuccessful attempts, I growled in frustration. Elizabeth, being the understanding caregiver, took my hand and guided me onto her bed. She laid on her back, spread her legs wide to reveal her glistening pussy in all its glory and said simply: “Fuck. Me.” It was all the invitation I needed. While I was pretty disappointed at our first attempt, the switch to missionary did make the motion slightly easier due to my familiarity. I lubricated my cock and gently eased my head inside her vagina. She was burning so hot inside and I felt my cock twitch in agonizing heat as she teased with her kegal muscles. I couldn’t take it anymore, as my brain kept repeating the line fuck her like an animal, and soon my cock was pounding her pussy into the mattress. Elizabeth was screaming my name over and over, to go harder, faster, whatever the rest of the line from Daft Punk’s song was, and I knew I wasn’t going to be able to last much longer. I knew she loved to be creamed inside, so I didn’t let up as my cock began to explode. Thankfully, I could feel the inner walls of her vagina contract around my cock, and could tell she was cumming as well. At this point, I was laying almost entirely on top of her, using only my glutes to drive my cock harder into her. We were two silly teenagers discovering sex for the first time, and goddamn, did it feel good. Once our orgasms subsided, we lay there on her bed, my cum leaking out of her pussy and talked sweet nothings to each other for a little bit. We understood the nature of our entanglement, and were in no rush to retreat, so to speak.

During our conversation, my fingers glided up and down her naked legs, making extra sure I brushed against her mound every so often. When the brush strokes began to increase in number, she took the hint and motioned for me to lie flat on my back. It seemed she wanted to take control of our second round.

I laid supine on my back and awaited her. She decided to tease me a bit by starting with a few light kisses on my lips, then my chest, and lethargically followed the same pattern all the way to my cock. At this point, I was semi-hard and eagerly asked for her mouth to reach its final destination. While she was apt to tease, she was in no mood to deny my request. Her mouth engulfed my member, sinking down past the head and applying suction that would make a vacuum cleaner blush. She held my head in her mouth a moment longer, then proceeded to give me one of the sloppiest blowjobs of my life. Her head bobbed up and down my shaft, making sure to apply suction as she drew up. She rarely stopped to breathe, as I could only assume she had learned to inhale through her nose. Despite her previous history of married lesbian life, I was happily surprised that she could suck cock better than I had experienced in a long time. Her tongue performed wonders, licking my frenulum in a light and sensitive touch which drove me bonkers on the receiving end. She sucked me off like a champ and brought my cock back to life from the proverbial death-post-orgasm. Once my rod was nice and hard, she sank down on top of me, flooding my dick with another round of her heat. She rode me like an expert ranch hand does a bull in the ring, except for the twisted nuts part thankfully. She grinded, she pounded, she fucked me and all I could hear was the chorus line of Closer by Nine Inch Nails echoing “I wanna fuck you like an animal/I wanna feel you from the inside.” Eventually, she grew too tired to bounce on my cock, so I motioned for her to lean on me (when you’re not strong…) so I could pick up the pace myself. We fucked like that for what seemed like an hour when it was probably 5 minutes until I felt another wave of pleasure skyrocketing me to the moon again. Her pussy clamped on my cock again, and she shudders indicated yet another wave of climaxes was at hand. She flopped down beside me covered in sweat and her legs doused in cum leaking out, proceeding to nestle into the crook of my collarbone.

Time passed slowly. I began thinking maybe I could ask Elizabeth about one sexual act I had been dying to try for the longest time. I gently got up and asked her politely if she liked anal sex. I had never experienced what it was like to fuck a woman’s ass properly, as most partners I’d been with either A) Didn’t like it whatsoever, or B) Were too afraid of trying to fit my cock inside their ass. I’m not exactly massive, but I am thicker closer to my head which could easily come across as intimidating to any first timer. Thankfully, Elizabeth surprised me again that night and told me she normally doesn’t have anal sex the first time she meets someone. BUT for me, she was open to trying my cock on for size in her ass. I grew giddy with excitement, like a child given their first cookie; I was about to have anal sex for the first time, with a bisexual milf who adored my body. I couldn’t believe my luck nor my ears.

We settled on the other bed in her room, and I started out by giving her a proper rim job to open up her rosebud. She tasted sweet, a mixture of leaked juices from her pussy and my leaking cum, and I couldn’t help myself from tonguing her hole more and more. While I teased her ass open, she went to town teasing my cock hard with her own spit. My cock didn’t take long to grow in her expert hands, as she then guided my cock to her willing asshole. We started with missionary position, but soon found it difficult to fit inside. Before I could drown in despair, my foxy minx told me she wanted to try doggie since it provided the most maneuverability. She got in position, with her head bent down and her ass staring up, begging for my cock to enter. We had to start out slow, as she hadn’t had anal sex in a while, much less with someone my size. We took our time once I was inside, listening to her orders of how far she was comfortable taking me. I was too excited to pass up the opportunity, and her sphincters clenched my cock tighter with each thrust. I kept applying more spit to my cock to encourage a smoother ride. My vixen became more comfortable with my size, and soon was pleading that I fuck her harder in her ass. She was no stranger to yelling out my name at this point, and was eager asking me to fuck her ass harder and harder. Who was I to deny her the pleasure? I began to ram my cock inside of this beautiful milf with abandon I did not know I was capable of. A wise man once said, with great power comes great responsibility, and I had lost sight of the last part of the phrase. Unfortunately, our anal sex didn’t last as long as her ass was so tight I could barely hold off my orgasm. Her rosebud took hold of my cock like an anaconda does its prey and squeezed every last drop of my cum into her ass.

I pulled out and nonchalantly offered a shower together to clean up the mess we had made of ourselves. She happily agreed it was for the best we clean, especially following our venture into the once taboo of anal. We cleaned each other off, shared a few passionate kisses, and dried ourselves off before sharing a night cap. We rested for a time, chatting about the future, what my plans were, what her life had been like married, and things she wanted to accomplish. I learned a lot about Elizabeth that night. In a word, my experience was surreal. We fell asleep shortly after, and awoke to my alarm going off, indicating I needed to leave for work 4 hours after falling asleep in her hotel room. We agreed, it was an emotionally sexual experience, I her first cub, and she, my perfect milf.

Source: reddit.com/r/gonewildstories/comments/908lu6/the_time_a_cougar_taught_me_anal_sex_mf

3 comments

  1. She was incredibly patient with me, and I seriously appreciated her every instruction.

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