Cougar on the Roof

(Note: this is part of my weekly series #freeloveFriday, where I bring back my early erotica stories for your enjoyment)

I love live music.

But I hated the guy who was playing at the wine bar.

His repertoire was some weird blend of wannabe scat talking and experimental chords that would have been fine with a college coffee house crowd, but were totally out of place in the wine bar.  It was like somebody gave a jazz-trained chimpanzee an electric guitar.  The sounds coming out of the little amplifier he was using seemed to have no connection to the song he claimed to be singing.

Or least, that’s what the woman sitting next to me said when she asked the bartender how long he’d be playing.  The answer, apparently, was all night.

I grinned into my wine, and she caught the slight smirk and had the grace to look a little embarrassed that somebody had heard her comment.  But she also looked a little pleased at the same time that her bon mot had been appreciated.  She gave me a small wink, and retired to the furthest corner of the lounge, a spot as far away from the little amplifier as possible, now that the guitarist was abusing it his esoteric version of Sea of Love.

I was in this small northern ski town for business, and whenever I stop here I make a point of coming to this particular wine bar.  It makes a change from the mid-level steakhouses I usually eat at when I’m on the road, and there’s usually somebody to talk to about more than just “the game” or Christian AM radio.

People, in fact, like the woman sitting over in the corner.  I saw that she was buried in a book, and I made out just enough of the cover to see that it was something by Colette.  The Ripening Seed, if my college French skills still survived.  She was dressed well, if casually, and she had an air that said she was perfectly comfortable sitting by herself in the middle of a crowd.  She also looked like she was in her mid-forties, and was taking great care of herself.

There’s a certain sensuality about some older women that I’ve always been attracted to, and this woman definitely piqued my interest.  But her body language and her book put something of a barrier between her and the world, plus the music was almost the pure opposite of mood music, and was killing just about any sense of atmosphere in the room.  I let the thought of any flirtation die and focused on making chit-chat with the bartender about the latest wines they were pushing.

There was a 2009 Rombauer Chardonnay that they were featuring for happy hour, which fit my Peyton Co. expense account just fine.  It was better than average, and certainly better than the regular Peyton sales guys were drinking, if they even drank wine.  Most of the guys who who travelled my region were burger-and-beer types, and more power to them.

“From the lady,” the bartender said, interrupting my reverie about the team’s drinking habits.  “It’s from the reserve list.”

Whatever it was, the wine was fantastic.  It sat on my tongue like warm honey and spices, and I raised my glass to the woman in the corner, who I could see in the mirror over the bar.  She smiled, and motioned me over to her.  I joined her at the distant table just as the musician, mercifully, took a break from the twisted chords of Strawberry Fields.

“Oh thank god,” said the mystery woman, “We can actually have a conversation.  I’m Sarah.”  She offered her glass in salute.

“I’m Fred,” I replied, and we clinked glasses and each took a sip.  Sarah motioned to the bartender, who brought over a full bottle of whatever we were drinking.  I caught the date on the label, and saw that it was a few years older than I would have thought.  She caught me looking, and smiled.

“It’s a little older than some people find appealing, but it’s fantastic once you uncork it.”

“It certainly seems that way,” I said, and gave her a grin that let her know I knew that she might be talking about more than the wine.  “I always think that with age comes ripeness and flavor.”  What the hell, I figured, let’s push the innuendo as far as it would go.

“I think,” said Sarah as she topped up our glasses, “We’re going to enjoy our bottle.”

We talked for a bit, about the town (small), her life (divorced, one kid in grad school), my job (regional manager for Peyton, covering four states) and then, at last, her book.

It was by Colette, and it was indeed The Ripening Seed.  I vaguely remembered it as story of first love, a boy and a girl on a seaside vacation.  But Sarah laughed when I told her what I recalled of the story.

“Oh,” she said, leaning closer as if sharing a secret, “Is that how you remember it?”  I saw a secret smile play over her lip as she looked at me over the rim of her glass.  “It’s so much more than that.”

Right as I asked her to remind me what else there was to the story, the musician came back from his break and struck up an acid-trip version of Begin the Beguine.

“Oh, I can’t take any more of this crap.  Come on, I’ll show you what I mean, but not here.”  Sarah grabbed the bottle and pointed at the table, “You get the glasses.”

Bemused, I obeyed her instruction and then followed her out of the main bar, through a smaller seating area and then through a door that led to a set of stairs leading upward.

“Uh, ” I said, “Aren’t they going to mind us going into the staff areas?”

“Hah!” Sarah snorted, the wine starting to affect her volume levels.  “Honey, I own the building.  Got it in the divorce.”


As I followed her up the stairs, I had a chance to admire her ass in the snug jeans she was wearing.  I love older women in tight jeans, there’s just something sexy about a woman who knows what flatters her shape and doesn’t try to dress too young.  A million twenty-somethings would have killed to look that great from behind.

Maybe the wine was going to my head as well, too.

At the top of the stairs, we exited out an access door and stepped out onto the roof.  While not a tall building, it sat in the perfect position to look out over the tiny downtown area and the lake just beyond, where the lights of the shoreside hotel were reflected in the calm water.

I could hear a gentle susurrus of water lapping on the sandy beach, and in the distance, a train whistle blew, although it was too far away to hear the rumble of boxcars yet.

Sarah set the wine down on a small table and I set the glasses next to it.  The table rested against a low wall that ran all the way around the roof to prevent anybody falling off.  It was clear that this area got visitors, and I imagined it as perfect place to watch the annual boat races or the Fourth of July fireworks.  In fact, as I noticed a set of patio furniture with overstuffed cushions and a long divan for sunbathing or sleeping, I felt as if was as if I was looking at somebody’s private deck or backyard, rather than the rooftop of a commercial building.

“Look there,” said Sarah, and pointed.  My gaze followed her raised finger, where I saw a bone white crescent moon hanging low over the hills on the far side of the lake.  She turned toward me, leaning back against the wall and picking up her glass.  “There’s only one thing better than a glass of wine in the moonlight,” she said, the tone of her voice sending heat directly into my groin.

“What’s that?” I asked, stepping closer to her.  She hooked her fingers into my belt and pulled me in even closer.  Snaking one arm around my neck, when her lips met mine I could could taste the wine we had been sharing, and when her tongue darted  into my mouth, I met it with equal energy.

Sarah broke off the kiss just as we both ran out of breath.  Grinning impishly, she said, “The only thing better than a glass of wine in the moonlight is the taste of it on a pretty man’s lips.”  She stepped back to consider me.

And I considered her words.  Pretty?  I think I’ve been called handsome, or good-looking before, but never pretty.  I decided that I didn’t hate it, but was distracted from the whole thought process as she reached up and unbuttoned the blouse she was wearing.

In the dim glow of the lamps that illumined the outside of the building, I saw the swell of her breasts over a black lace bra, and a faintly pale line where her tan ended and softer, whiter skin began.  Teasing me, she inhaled deeply as she stretched her arms over her head, and it was all I could do not to reach out and grab what was so clearly being offered.

“Come here,” she said, as she lowered her arms again and picked up her wine glass.  She swirled a finger in the dark liquor.  “How does it taste?”  Sarah trailed drops of the rich wine across the tops of her breasts, and pulled my head into in to her chest.

Like a baby being offered food, I lapped eagerly at the dark drops that glistened on her skin, my tongue rasping over the lace of her bra.  The musky perfume she wore and the honey smell of the wine made me suck eagerly at her flesh.

Leaning back against the parapet, Sarah moaned and pressed me more firmly against herself.  The lace was damp with wine, and I felt a nipple stiffen against my tongue where I nibbled at it through the silky cloth.

She gasped and tightened her grip on my hair when I drew the nipple in firmly, sucking wetly at it, drawing it tightly between my teeth, tongue moving faster against the fabric that held it captive.

“Mmmm,” I heard her murmur, “How does that taste, baby?”

I released the hard little nub and straightened up.  “Gorgeous.  I want more.”

Sarah laughed, and handed me her wine glass.  I took a sip, and watched her slide her jeans down her legs, and then step out of them.  Her unbuttoned shirt created an exciting interplay of enticing shadows where it draped over the tops of her bare legs, and I could just see the lace of a thong in the dim reflected light of the street lamps.

A wave of her perfume washed over me, and I was struck by how her choice of scent revealed who she was, and matched her so well.  It was not a light or flowery, but instead it was a deep, musky perfume, both mature and powerful without being overwhelming.  And yet, at it’s core, it carried a sexy erotic charge that stiffened my cock immediately.

Sarah gestured at the divan, and I obediently sat down.  I was now looking up at her half-naked, half clothed body.  She knelt, and looking me in the eye, slid her hands along my thighs and undid my belt and the buttons of my fly.  When my erection was freed and the rest of my clothes pulled off and tossed aside, she bent her head forward and lightly kissed the tip of my shaft, sending an electric jolt through my body.

I must have moaned as I reached for her, because she whispered “Shhh, baby, shhh,” and she took ahold of the hand that I had placed on her head, then moved it to one breast as she pushed me backwards onto the cushions.  She moved over me, straddling my chest with her knees on either side of me, sunk into the deep pillows.

I could feel the satiny texture of her thong as she moved down and brushed her sex against me, and it was all I could do not to tear the flimsy cloth aside and plunge myself into the heat I felt coming from between her thighs.

Instead, I found the clasp of her bra, and freed her breasts to the night air and my hands.  I covered them both, the nipples raising against my fingers as I kneaded them gently.  Sarah arched her back, her shirt slipped down off her shoulders and I moved my hands to the finely boned skin there, to pull her both into my kiss and down onto my cock.

Pressure against my chest stopped me, and I saw that Sarah was holding herself back as much as she was slowing me down.  She reached down to where our bodies almost connected, and I felt the cool slipperiness of a lubricated condom as she unrolled it down my shaft.

“Ohhh,” she moaned as she drew her hand away, tracing my length and, at the same time, spreading herself open, “Now…”  Her fingers guided me past the lacy strip of cloth and I was surrounded by the tight and velvety heat of her pussy as she sank onto me, one hand still on my chest for balance.  Once I was deeply inside, her other hand moved to her breast and she cupped herself, kneading and pulling even more firmly than I had been doing, her eyes closed and her mouth open as she pinched her nipple between two knuckles.

Sarah lifted up, and sank down again, her moans now punctuated by higher pitched cries, as each time she seemed to drive me deeper into her body.

Then she put her hands behind her, on my thighs, and I felt my cock press against the slick upper wall of her delicious tunnel.  She thrust against me in short, bucking movements that reached a quick, jerky rhythm, and her cries were now short, high pitched exhalations that reached a breathless crescendo as she finally tensed and quivered.  Her grip on my legs tightened and her nails dug into my skin as she groaned her final release.  The tide inside my own body receded slightly as she stopped moving, and I focused on slowing down my own breathing to keep control.

Still keeping me tightly inside, Sarah straightened up and rested her hands on my chest.  “Mmm, baby, that felt great!”  She locked her gaze on mine, and started to move again, slow and languid thrusts that stroked me from tip to root.

She paused at one point when I was fully buried in her, and I groaned when I felt her inner muscles tighten around me.  She gave a low laugh, “Do you like that, baby?  Do you like having your cock squeezed like that?”  I tried to answer, but could only gasp as she pulsed around me again, the exquisite pressure taking away any words I could have used.

“Feel that, baby?” she asked, tightening and then releasing me in time with her slow thrusting.  I nodded, and she sped up again.

I moved to put my arms around her and draw her down so I could kiss her while we rocked together, but in spite of being smaller than me, she managed to push my hands back down to my sides, pinning me to the cushions of the divan.

“Shhh baby, shhh,” Sarah whispered, as she held me captive inside and out.

Her head dipped forward, and her hair fell over my face as her tempo reached a faster rhythm, her breaths the only sound I could hear as they quickened, and her intense perfume surrounding me as I met her thrust for thrust.

I got lost in the rhythm of her body, and when she came again, I climaxed with her in a heated, pulsing rush that seemed to begin at my toes and pour out in lightning surges.  Sarah slowed, and milked me even more with the sensual muscles she had such exquisite control over, drawing out final spasms even as she sighed and sank down to lie on top of me, finally letting me put my arms around her as we both quieted down and our breathing settled.

I don’t know how long we stayed like that, with the slim crescent moon and it’s companion star watching over us, but I must have dozed briefly, because I was woken by the loud rumble of freight cars as the train passed through town.  I felt experienced fingers circling my softening manhood as Sarah’s weight lifted off me, keeping the condom in place as she drew away.

She stood, and stretched, and I had a few seconds to admire her ripe body before she fixed her underclothes and buttoned up her shirt.  Then she drew her jeans back up over her hips in a languid display that was almost as sexy as watching her take them off.

She poured the last of the wine into one of the glasses, and raised it to me in a toast.  “Baby, that was fantastic!”  Her secret smile was back in place, and she drained the glass and set it back down on the small table.

I stood up, shivering a little in the night air.  “I’m in town for another couple of days,” I said, “How about breakfast tomorrow.”

She considered me for a few moments, then stepped up and gave me a kiss on the cheek.  Long after she left, I could smell her perfume, a strong, mature scent that stayed with me even as I considered her last words, uttered just as she walked away

“How about I call you?”

(This story originally appeared on the website  Sigh-we miss you, O&C!)


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