So if you've read my previous 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. Note: this story I'm writing currently, the previous one was written a few months after its events and I just reposted it. So I apologize for any inconsistencies between these two stories, as it has been some time now.
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 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 I believe. It was a bit overcast so it had been somewhat chilly that day, and rainy later on.
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, and still can't because I'm 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 hints 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 mentionedThe Graduate. If you've never seenThe Graduate go to a new tab and proceed to watch this titillating film.
Are you back? Pretty weird movie right?
Now, I like to think that I'm not, nor have I ever been, a fool so after this hint I finally picked up what she was putting down. I drove us back to her place, which was a fairly nice apartment complex, her's being a two bedroom apartment with a nice, 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 laying in bed next to this blonde goddess.
For whatever reason, I like to think a piece of my virginity still clung to me and made me into an awkward idiot that night because for the entirety of the movie she was laying under the sheets and I STAYED ON TOP OF THE SHEETS. THE WHOLE TIME. I still cringe thinking back on that.
Luckily she didn't seem to care, because as the movie ended she turned to be and was a little giggly, asking if she could just kiss me already. I couldn't help but smile and I leaned in to seal the deal.
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. Harder than writing a doctoral thesis on theoretical physics. Harder than trying to beat Sub-Zero in the arcade mortal kombat game, if he was also erect as fuck.
So yeah my 18 year old cock was a ragin'.
She could feel it through my jeans as we rubbed and grinded our bodies 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 literally 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 give me the best blowjob I have ever had in my entire life ever.
Kidding, it wasn't really all that to be honest. Sure she was good, and she could take a lot of it down her throat, but she didn't really apply any pressure when she sucked. But alas, that was the only disappointment in an otherwise flawless night. After she sucked my cock for a little while I was aching to be inside of her. 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, my oh my this woman's body. It was one for the history books I tell you. 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 isso 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, the interwebs, fuckin everything. I pulled out all the stops to pleasure this gorgeous woman, and if the grool dripping down my beard 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 heaved it as if it were the mighty hammer Mjolnir, and I set upon getting inside this woman with every fiber of my being. 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. She hadn't mentioned the word 'condom' and I wasn't about to, there's no way I'd leave this ecstasy. 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 felt like a fucking god.
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 erupt harder than Mt. Vesuvius.
I pumped that cougar pussy full of getting head in car 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. We ended up fucking once more that night, and 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.
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 complications along the way.
And that-is a story for another day.
WolfTango