[m] [older F] Mrs. Robinson or: How I Learned to Stop Worrying and Love the Cougars

I realized that the last time I submitted this story I left out a fair bit of the actual juicy sex-stuff, which is why people read these stories anyway, so I’m giving it a redo to try and add more detail to that section if my memory will allow it. Bear with me here.

So, if you’ve read my first story you know that in my first semester of college, I had been frequenting tinder and was lucky enough to lose my virginity to a fellow freshman girl. Meanwhile, I had also been messaging and even had met up with a 37-year-old woman, though at the time I wasn’t entirely sure where it was heading. This story is where it was fucking heading, so strap yourselves in. Also for reference: I am about 5’11”, dark brown hair, brown eyes, I didn’t have a beard at this point in time but kept some stubble, I have a fit body with a decent amount of body hair, and a good-sized cock lengthwise but a very nice amount of girth. Kelsey is about the same height, darker eyes, long blonde hair, slim and toned body, very large breasts, and a great round ass.

The day after I lost my virginity, I heard from Kelsey. She wanted to see each other again since our last meeting ended while we still had much to talk about. We were planning on meeting Friday to go get dinner near her place, and waiting for Friday night to finally arrive was almost too much to bear.

When Friday night finally rolled around, I got in my car and drove over to her place to pick her up. We both were a little dressy as she mentioned that this was a somewhat nice restaurant we’d be going to, so I went with the jeans and button-up shirt look, whereas she wore a skirt and a nice blouse with some kind of jacket over it.

We got to the restaurant and had a valet park my car (it was indeed a classy establishment) and we made our way inside. Luckily for us the wait for a table was not long, and we were even given a table out on a covered patio where we could watch the gray skies turn dark, and for the rain to slowly drizzle down. Not your typical romantic sunset view but stormy skies have always held a warm place in my heart.

We had been chatting back and forth now for a little while, ordering our food and she even ordered a drink or two (I couldn’t, because I was underage. So that added an extra interesting dynamic to an already interesting evening.) After finishing up our food, the topic of what to do after dinner came up. She offered to go back to her place to watch Netflix. Yes, a 37-year-old propositioned me with “Netflix and Chill” before it even became a thing. Astounding.

I agreed, my recent loss of virginity not yet allowing me to pick up on subtle hint that a woman wanted me to dive between the sheets with her, but it still sounded like hanging out with this cool woman would be a nice conclusion to our night. She suggested that we watch a movie that tied into our little dynamic, that being the older woman with a younger man, and she mentioned *The Graduate*. If you’ve never seen *The Graduate* go to a new tab and proceed to watch this titillating film.

Are you back? Pretty weird movie, right? I still didn’t fully grasp that she wanted to fuck me yet. In the back of my mind I was thinking “oh shit maybe she is flirting with me???” but my practically virgin brain was ignorant to such nuance.

I drove us back to her place, which was a fairly nice apartment complex, her’s being a two-bedroom apartment with a very spacious, open living room. She led me into her bedroom, claiming we could watch the movie from the comfort of her bed and I had to grin to myself, realizing I’d soon be lying in bed next to this blonde goddess. Of course, I still didn’t think I’d be fucking her. At least, maybe I didn’t think I’d be fucking her just yet and it’d be a third date type situation.

Because I genuinely did not expect that I’d be fucking her, I didn’t pay attention to any of her cues. I ignored all the factors leading up to this moment since I decided, for some reason, that while she got into bed under the sheets, I should lay on top of the sheets.

For the entire movie.

Yes, you read that right. That really happened. I laid in bed next to a hot blonde cougar that wanted to fuck me for the entire 106 minutes of film about a cougar fucking a young man.

I must be stupid hot, because instead of kicking me out for my foolishness she went on the offense and asked if she could just kiss me already. After that it *finally* kicked in. I was going to fuck this woman.

Our lips pressed against each other tightly, then our bodies followed suit. My hands slid over her sides and up to her breasts, the biggest ones I’d felt at the time, probably have ever felt actually. I was harder than a diamond in a snow storm as the old adage goes. I don’t think I have ever been as hard and ready to fuck as I was in that moment. My 18 year old cock was a ragin’.

She could feel it through my jeans as we rubbed and grinded against one another, and she just gave me this sexy little smirk that almost exploded my heart and my testicles in one go. I laid back and let her move on top of me as she unzipped my jeans and slid them down, rubbing her hand over my underwear covered erection. I was going insane by now, watching her every move as I almost drooled in anticipation.

She held eye contact and hooked her fingers in the waistband of my boxers and pulled them down, revealing my throbbing young cock to her. She held it for a moment before sliding her lips over it and proceeded to wrap her lips around the head and look up at me. That moment is frozen in my mind as one of the hottest things I’ve ever seen.

She gave some decent head, she could’ve sucked on it a little harder but I was loving it anyway. After she sucked my cock for a little while I was aching to be inside of her, and she could tell. I reached down to help her strip off her clothes, as well as what was left of mine until we were both naked. And wow, this woman’s body. If I could show you lovely folks the pictures I would, but I don’t think she’d appreciate it all too much.

With her naked form below me, I couldn’t resist kissing, licking, tasting her body, up and down. I couldn’t get enough. I kissed down to her thighs and sucked on the soft flesh of her inner thigh, just grazing my teeth over her skin while I moved on. I got down to her pussy and all I have to say is that cougar pussy is without a doubt 100% Grade A all American goodness that I can’t recommend highly enough. It is *so choice.* if you have the means, I highly recommend picking one up.

I did what any hot-blooded 18-year-old guy would do when presented with such a fine, smooth specimen. I ate that pussy like my life depended on it. I swirled my tongue over her clit and sucked at it, I slid a finger inside of her surprisingly tight canal and curled up to try and find her G spot. I pulled out all my knowledge, everything I knew on eating pussy from previous relationships. I pulled out all the stops to pleasure this gorgeous woman, and if the grool dripping down my chin and the satisfied cries coming from up by the pillows were any indication: I did just fine.

With both of us worked up past the breaking point, there was only thing left to do. I gripped my cock and moved up towards her, set upon getting inside this woman without hesitation. I moved up and looked in her eyes, pushing my cock head through her dripping wet labia, into her warm and enveloping pussy. I was in heaven. I held her there as she wrapped her legs up around my waist and I started to thrust deep. I didn’t care that I was some 18-year-old college freshman. In that moment, in her bed, I was a fucking god.

I only had that one other experience fucking at this time, so I didn’t know much but I started to thrust fast, pumping away. I didn’t know any better back then so I just…*fucked*. I grabbed her body; squeezing her breasts, holding her waist, she was all mine. I soon learned that I was doing it all wrong, as she’d teach me, but she was moaning for me and begging for it harder. She was letting me have this one, it was all for my pleasure.

I don’t know how much time passed but I felt a stirring in my loins, and in all her years of experience she knew right away what was about to happen. But she held her legs tightly around my waist and begged me to cum inside her. Hearing any woman beg for my cum, in her or on her, is a surefire way to get my cock to fucking explode.

I pumped that cougar pussy full of my cum, I didn’t stop thrusting until I felt my cock go sensitive and my toes curled. We just laid there and looked at each other, then laughed a little and kissed. I pulled out and rolled over on the bed a new man. This felt like it was my real first time, it felt like I had fully shed my virginity. She got up and went to go clean up in the bathroom, so I just laid there smiling like an idiot as I moved to get under the sheets. When she came back we cuddled under the sheets until I was very quickly hard again and she was enthusiastically surprised about that. She said that’s something she loves about younger men, we can keep going and going and going. But this time she told me she wanted to teach me a thing or two.

I like to keep an open mind, so I stayed laying back and she told me to stay on my back as she mounted me. She explained that this felt better for her, and she could cum this way and I think it was this very moment that I learned a very important lesson. Sex is for *both* people. And boy is it better when both people get to cum. She slid my cock inside of her and started to sink down on it, resting her hands on my chest while I held her waist. It was my first time really feeling a woman’s weight on top of me and I was loving it. She began riding me, moving her hips and gyrating them up and down, this new sensation was incredible. On instinct, I moved my hands around and grabbed her ass cheeks, squeezing them in my grip and she moaned extra loud from that. I looked up at her and she let me know to keep doing that, that’s what helps her cum.

And I wanted that. I wanted to make her cum. I *needed* it. She had just given me immense pleasure and I needed to give that back to her. It wasn’t a hard concept for me to finally grasp. So, I lifted my hips slightly and squeezed her ass as she rode me, and before long she was moaning and clamping down on me tightly. She bent down and smothered me with her breasts, rubbing all over my body as her hips bucked and she came for me. I took in her scents, how her hair rubbed in my face and her soft skin, I was one with her in that moment.

After she came, she sat back up with a smile and told me I could fuck her how I like now. So, she got off me and laid back on her back, instructing me to get between her legs again. This time though, it wouldn’t be so simple. She told me how to thrust. She told me how I could manage my thrusts to make it just as pleasurable for the woman, how I could control it. I started to pick up on her tips, slowing down my thrusts and going deeper, holding myself deep inside for a few seconds before sliding out and going back in deep, then switching up with some shallower thrusts and speeding up. One technique she taught me that I still use very much to this day is sliding in all the way so I can feel my pelvic bone push against her clit, then thrust my hips in a manner that I stay inside but grind against her. 100% of the time it gets a fantastic result. Various other methods could be used to prolong the sex and hold off my orgasm, though those took a bit longer to grasp. We did continue to meet for several months, after all. But that first night, this second round when I finally felt myself coming to my edge she asked if I wanted to cum on her and that question always gets a yes out of me. I pulled out and moved up to straddle her chest, desperate to cover those huge breasts of hers. I shot a few thick ropes onto them as she moaned for more, leading in a very satisfying orgasm. The second of very, very, very many she’d give me.

But all good things must come to an end. With that, it was time for me to head back to my dorm. We agreed we were definitely going to meet again, and I was concerned about the fact that I came inside her. She insisted that as an older woman, she knew her body and her cycle so she knew when she would be ovulating. I took her word for it, especially since she said she wanted to meet up whenever she wasn’t ovulating so I could always cum inside her. Also, she just assumed since I wasn’t experienced that I wouldn’t have STDs which while correct was a little foolish on her part. She was regularly tested too though so I knew she was clean after the fact.

This sparked a lasting relationship between a young man with much to learn, and an absolute bombshell cougar eager to teach everything she knew. But there were quite a few interesting developments along the way.

But that…is a story for another day.

Source: reddit.com/r/gonewildstories/comments/60jdmm/m_older_f_mrs_robinson_or_how_i_learned_to_stop