The Cougar Chronicles, Part I: The Bar Hook-Up (M/F) | 2016

My first semester of graduate school was probably far and away my most sexually adventurous one. Before a lost weekend with Belle, and before a summer fling with Paige, came a thrill ride of lust and learning.

Jen was a non traditional student, finishing out her graduate program as I was starting mine. The 38 year old, raven haired woman encompassed many of my innate schoolboy fantasies. When she showed up on the first day of our teaching workshop to help the newbies, a part of me certainly wished she was open to a few extra curricular lessons.

When she arrived on the first day she exemplified that kind of adult put togetherness that was inherently sexy; and for her that was all icing on an incredibly driven, athletic cake. Jen was no stranger to openly discussing her own views on the horrors of growing old; she'd explain how she railed against aging by going on 5 AM runs every weekday.

So you can imagine how taut and strong her legs looked under the cover of black slacks. And her ass...god damn. She had a white button up on top, which complimented her classy ensemble. Her tits budded tightly against the material, and while they were small, I still could only imagine burying my face against her mature chest.

Like these things often happen, my admittedly hungry eyeing of her happened over the course of the day with sideways glances and sublte looks. Potentially the most dangerous of these ended with a settling of held eye contact...Jen had the most beautiful almond colored eyes.

Couple all of that with a rapier wit and a sound mind, and I was pretty fucking smitten. But, while I felt pretty good about getting things going with girls my age, the fact that she was a little bit less than twice my age was a pretty intimidating factor. Oh, and she was married.

But that all started to change one October weekend. As per usual, the teaching staff pilgrimed to a townie bar to knock back pitchers of beer and unwind after another busy week. Jen wasn't always able to get away from her husband, but she managed to kick up some free time, and joined us for our bender.

Normally I played pool with Justin and Claire. Justin was a pretty lanky dude, Claire was a curvy redhead who was his...okay I never really paid TOO much attention to whatever they were, but they definitely weren't Facebook official. But they certainly hung out a lot. Anyway, I abandoned the almost couple to sit at the bar with Jen, appropriately, at least for that night, serving as her shoulder to cry (vent?) on.

"Marriage sucks," she mused in between sips of beer.

"Sounds like a bittersweet problem," I led with a bit of self deprecation, "at least you get to crawl in bed with someone." I nudged her elbow with mine.

"You're so naive," she shot back, downing her beer, "besides, these days all we do is crawl...no sprinting, just slow, steady, boring crawling,"

She might have been mixing metaphors, which would make sense given our academic background. Regardless, I inched a bit closer.

"Still...better than sleeping alone,"

"Not exactly," she motioned for another beer while shifting in her seat. "Once you get that first bit of physical contact, you're left aching for more."

I tossed the barkeep a couple of dollars, wanting to focus on a clear mind for the foreseeable future.

"I'll keep that fear in mind for whenever I end up finding someone. Happy wife, happy life, right?"

We both giggled, a lull sneaking into the air. Every so often we'd both toss our hands in the direction of the pool table that Justin and Claire were at. Every so often they'd toss a few verbal jabs at each other. Maybe there was trouble in paradise...or really, purgatory, given their nameless nature. At some point in time during our surveillance, our knees started to angle against each other. And I felt a bit of electricity.

Shortly after, Claire ended up bending over pretty much in front of our field of vision, her heart shaped ass ever so sublty swaying back and forth. Suddenly, I felt Jen's fingers dig into my arm.

"I've done so many things to make him more happy...," she took another pull, "all this running, I added squats...I even shaved...in places." Jen, surprisingly, blushed at the level of sexuality she was starting to explore with me.

My feelings started to cocktail...or maybe dovetail, in separate directions. On one hand, those images were absolutely turning me on, but on the other, I sort of commiserated with where she was coming from. I pulled my knee away and steadied my gaze on the wood of the bar.

"You know, I don't know too much about super lengthy relationships, but I gotta believe if that level of compatability isn't there...something is up with one of the partners," I turned towards Jen, settling a hand over hers, "Jen...you're fucking beautiful. And I mean that right now, in the most selfless way. I couldn't imagine any world where a guy doesn't fall absolutely head over heels in lov-lust with you. Y'all should be having marathons in your bedroom every night."

Throughout all of this, my heart was racing and my cock was stirring just a little bit.

"Thanks...for all of that," she slowly said.

I realized far too late that I had leaned forward in her direction, but thankfully, she was doing the same. Our eyes alternated glances towards each others' lips, but after an incredibly pregnant pause, she deftly pulled her hand out from under mine, and smoothed out the top of her jeans.

"You know...Claire talks about you a lot,"

I was pretty speechless, because I guess in my span of pining after Jen, I hadn't tried to build up anything with our redhead coworker.

"She's recently been obsessing over your sweater vests...which I think are pretty sexy myself. And she loves the way you command a room," Jen's eyes lit up, as a smile began to grow wide across her beautiful face, "and she was just talking about how Justin isn't forward enough."

I knew what I had to do.

Slinking out of my chair, everything else was like smooth clockwork.

I settled in near Claire, who was set up for another seductively bent-over shot. As I placed a hand on her back, I felt her shiver beneath me.

"Hey stranger," she said as she stood up, pivoting in my direction. Since most of the night I had been watching her from behind, I hadn't noticed that she had such a perfectly low cut black shirt. That, and the handfuls of breasts they contained, were nearly pressed up against my torso. Claire's green eyes settled up in my direction, as she bit her lip.

"Do you want to get out of here?" I breathed.

To be honest, I was sort of flying by the seat of my pants, and I learned later that Claire and Jen had set up this very thing, but that night was a solid introduction to a sexy semester.

Claire and I wrapped arms around each other as we adventured to her apartment two blocks away, laughing and reciting old jokes we didn't even know we both knew. We swapped stories over shitty students, and if she hadn't pressed me against a wall and kissed right outside her door, I would have forgotten what I was even doing.

But the strawberry taste of her lip gloss and the way she bit my lip when she pulled away flipped a switch in my mind, and as she started to unlock her door, my hands found her hips and I ground against her from behind, kneeling a bit to kiss at the back and sides of her neck.

She giggled and moaned, kicking open the door and pulling me by one of my hands in. She settled back onto a table and I slithered in between her thick thighs. Our lips crashed against each other again, before I pulled her hair back to assault her neck. My cock had hardened pretty quickly against my own jeans, and our hips were quickly grinding into each other.

"I have condoms...fuck...in my bedroom," she breathed out as I kissed down to the tops of her breasts.

"Lead the way," I growled after tearing off her shirt. A simple purple bra encased the heavy breasts, and I looked forward to the near future where I would rip it off and orally assault that chest.

We made out, bouncing between walls, before she crawled onto her bed and grabbed a condom from her night stand. I slapped her ass from behind, and kissed the small of her back, sliding a hand up to undo her bra.

I slapped her hand away when she offered me the protection.

"I'm busy," I snarked, sliding my hands around the front of her jeans and inching those down as well, followed by my eager kisses. A black thong was all that was left between me and everything I wanted in that moment. I pawed and kissed at the globes of her ass, while she worked herself out of her jeans, nibbling every so often.

Bringing my hand up, I pressed a thumb against her asshole, sliding it down against her pussy from behind, smiling as she moaned out. Claire was exactly where she wanted, moaning and cussing against a pillow, shaking her heavy ass against my touch. I paused for a brief second to peel off my shirt, pulling her hips back against my clothed member.

Sliding my hands up to massage her tits, I ever so slowly pumped my hips dryly against her thong covered cunt, and before long she was whimpering and pressing back against me. I kissed her spine, adventuring back down to pull of the thong, following that up with kisses as well.

Claire desperately pressed her sopping cunt back against my face, and I eager lapped at the slightly hairy lips, working a tongue deeper into the folds as I slapped and grabbed at her ass. I ran my thumb around the outside of her asshole, as she wiggled and shuddered against me more and more.

"Oh God, please fuck me!" she tossed the condom back in my direction, and I smiled as I bridged up to give her what she needed. Sliding my jeans and boxers off, I bit open the condom wrapper and rolled the rubber down my thick, throbbing length. Wrapping my hand around the lower end of my shaft, I teasingly drummed my tan cock head on the small of her back. The flares of Claire's red hair gave way to her emerald greens, as she bit her lip and gave me a pleading glance.

I obliged her, sinking my cock into her warm cunt. We settled into a fast groove pretty quickly, as I bundled her hair with one hand and spanked her with another. The feeling of rough, emotionless sex was absolutely something I needed in that moment, and I threw my own groans into the mix as her redhaired pussy clenched with pleasure.

Claire's ass slapped against me strongly, echoing the spanks I was giving her. Before long I couldn't take anymore, and I quickly picked up as much speed as possible, digging my nails into her skin as I slammed heartily with finality, sliding out as my cum burst into the condom.

That was the one and only time Claire and I hooked up. But we were decent enough friends through it all. My emotions just laid elsewhere...