Harmless Cougar Fantasy

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All rights reserved. No part of this document may be reproduced without permission from the author. This is a work of fiction. Any resemblance to real people is strictly coincidental. If you aren’t at least 18 years of age, don’t read this… blah, blah, blah.


‘So there I was, with my tongue up this chick’s ass… She was looking back at me like, “Do I know you?”… I was looking back at her like, “Does it matter?” You know how boring those bank lines get.’ – Andrew Dice Clay

That bit always did make me smile. And smile I did as I slowly sank my cock into Hanna’s upturned ass. She hissed a bit. I held my position, with just the head of my cock trapped my her sphincter.

“No, don’t stop, Joe. a deal is a deal.” she panted. “Just go slow. You’re enjoying this, aren’t you?”

I barked a quick laugh, then seized the twin globes of her asscheeks. Gripping and squeezing them, I thrust my cock another inch in.

“Hell yes, I’m enjoying this!” I glanced at a nearby stopwatch. “And I intend to keep on enjoying it for the next hour.”

Have you ever had your dick in a girl’s ass? Have you ever had your dick in a woman’s ass? How about a sexy, mature one 10 years your senior? Have you ever ass-fucked a hot cougar, not because she was particularly into anal sex, but really, really wanted to make your day? You should try it. It’s…. invigorating, to say the least. How did I find myself in such an enjoyable and not-very-normal situation? What’s up with the stopwatch? What deal? Let me back up and explain…

I’m a thirty-something male middle school teacher. I’m in reasonably good shape. I’m married with the requisite 2.5 kids. (fraction from my first marriage.) The thing about middle school teachers it this: we’re all crazy. Ask any teacher, elementary, high-school or middle school… they’ll tell you. The other thing about teachers in general is this: most of them are women. Many of my friends at work are female. This occasionally causes me problems with my beautiful wife. It has also gotten me into trouble in the past. But, it does offer good fodder for the occasional fantasy. Actually, I’ve probably got a fantasy about every cute female co-worker I have. This is one. Did it happen? Nope. Could it have? I’d say yes… that’s what makes fantasy so interesting. It’s the lure of possibilities.

Hanna was in her forties. She taught girls P.E. She was still very fit and shapely. Her ample breasts were only starting to sag. Thighs and buttocks were just starting to lose their battle with age and cellulite. She played tennis regularly and kept her body as firm as possible. Her shoulder length brunette hair was only beginning to show grey. She refused to color it. Hanna said she’d earned each and every grey hair. She was divorced with a cute high-school aged daughter who had occasionally baby-sat my kids. (Wait, don’t go there. The daughter is cute, but very much a minor. Stay on story here!) Hanna didn’t date… kinda hard to meet guys when you teach13 year old girls. She was devoted to her daughter and either spent time with her, or was working. (P.E. coaches put in a lot of time at athletic events and functions.)

Hanna and I were friends. We’d talk over fifteen minute lunches. We’d commiserate about things at school and what-not. Being a handy guy, she’d occasionally asked me to stop by her house and help with a few maintenance problems. This graduated into me doing some routine manly chores for her. Before long, I found myself at the top of an extension ladder, hanging Christmas lights on her second story. It became a running joke of how much she ‘owed me’ and that her tab was getting huge. Her being an attractive woman, and me being a horny guy, I’d make backhanded suggestions of ways she could clear her debt. I was never graphic, but did say dinner and a movie would work for me if her daughter would keep the kids.

These suggestions were gently rebuffed. I suppose my being married kept her from doing anything inappropriate by way of payment, but it didn’t stop her from using my free labor. Women. Go figure.

Anyway, a time rolled around when my wife was out of town for a week on business. I loudly lamented to Hanna that I’d be without good cooking or entertainment. casino oyna (Not completely true… I’m the chef at our house.) Hanna got a thoughtful look and invited me to dinner with the kids the following night. The next day at work, I told her the grandparents had asked for the kids, so I’d be coming alone. (This was a bit of a fib… I’d been on the phone the day before, angling for overnight care.) She’s smiled and said it’d would just be the two of us, as her daughter was at her dad’s this week. And if would I pick of a box of wine, she’d handle the rest. Dinner would be at seven.

“So. Does this make us even?” Hanna asked as she began clearing the dinner plates.

I got up to help her. “Not even close.”

“I didn’t think so.”

We’d put all the dishes in the sink. I refilled her wine glass and handed it to her. We leaned against opposite counters and regarded each other for a moment or two.

“It’s not that I don’t want to do anything with you… it’s just well, you’re married and I’d feel guilty and I don’t want to screw up our friendship either.”

“Not much of a friendship if only you benefit from our efforts.” I pointed out.

“Ouch. Okay, your right. I do owe you something. But how do with do this and not get caught? Or in too deep? Or all the baggage that comes with sleeping with someone… I really don’t want to be the other woman, here.”

I reached over and picked up her digital stopwatch off the counter, and began playing with it.

“How much time have I spent over here? I mean roughly? How many hours have I put in doing things over here for you?” I asked.

Hanna took sip of her wine and thought about it for a bit. She silently ticked off various jobs on first one hand, then began adding finger from the hand holding her wine glass.

“I don’t know. Seven? Eight?”

“About that.” I agreed. I held up her stopwatch with 8 hours punched into the countdown display. I held it out for her to see.

“Here’s what I suggest. I’ve been at your beck and call for 8 hours. You give me your time as payment for my time. Just as I did all the little things you couldn’t or wouldn’t do… all the dirty or difficult jobs you didn’t want to hire a professional for… you do everything I want for 8 hours. What do you think?”

“Whoa. Wait a minute. You want me to do anything you want for 8 hours? Be your sex slave or something?”

“Why not? It keeps things simple. A simple business arrangement. Your time for my time.”

“Yeah, but I’m not asking you to do any kinky sexual acts, just clean my gutters and stuff.” she said, draining her wineglass.

“Who said I’d ask you to do something kinky?” I asked.

Hanna just looked at me. It occurred to me then that all of my backhanded comments had been heard. Heard and ignored, not just missed entirely.

“So, is your time more valuable than mine?” I asked her, refilling her glass. This was at least her fourth of the evening.

“In this, yes!” she said defiantly, but with a smile. Obviously she was agreeing to the idea, we were now just negotiating details.

“Okay, fine. Two for one.” I tweeked the stopwatch display and showed her four hours. “Satisfied?”

“Four hours… I do whatever you want. Just business. Nothing else changes, no one finds out.” She took a deep breath and looked me in the eye. “Okay.”

“Then get over here and kiss me.”

“Nope.” she said, taking another drink of wine.

“Why the hell not? Are we saying no kisses or something?”

“Nope. You just have to start the countdown first.”


A little while later, I came up for air. I was lying back on her couch with my shirt open, jeans unzipped and shoes off. She was

straddling my lap with her arms on my shoulders. Her shirt was also open and I had been nuzzling her neck and breasts through their lacy confinement. Her skirt had ridden up and her lace clad pussy was barely visible as she ground it into my crotch. My hands roamed up her thighs and traced the curves of her ass.

“I just realized that you’re stalling.” I accused her.

At first she looked hurt, then broke into a broad grin. “Can’t blame a girl for trying.” She began to grind small slot oyna circles with her hips. My cock was straining to get out of its boxer and denim prison.

“I’m going to stop the clock and figure out a way to tie you up so I can get exactly what I want from you.” Her eyes widened at the word ‘tie’. I’m not sure if from fear or excitement.

“What. Exactly. Do. You. Want?” She asked, punctuating each word with a kiss to my forehead, nose, lips, chin and chest.

“Keep going. I want you naked or to be inside you in the next thirty seconds. Otherwise, I will figure a way to tie you down and then maybe I’ll spank you as I fuck y-uhhhh!” I lost my ability to articulate just then as she had sucked my entire cock into her mouth. I could feel my cockhead bumping the back of her throat. She had wasted no time at my threatened ultimatum in climbing down off my lap and kneeling at my feet, freeing my rigid penis and re-trapping it in her mouth.

Hanna then dropped her shoulders and straighted her neck out, burying her nose in my pubic hair as she took my cock halfway down her throat. Without thinking, I grabbed the back of her head and began making short thrusting movements with my pelvis. She steadied herself with her hands on my spread thighs, her nails digging in slightly, but she didn’t resist the control I was taking. After about thirty seconds of intense throat-to-penile pleasure, she pulled off. Gasping a bit for air.

“Nice to know I can still do that. I forgot how much fun that is.” she said with a smirk.

“Let me tell, you. I was enjoying it. More please.” I guided her back down onto my hard-on. For the next five minutes or so, she licked and sucked, fellating me with great skill, but without the extraordinary depth she had demonstrated at first. Getting impatient and feeling my balls begin to tighten, I again ran my fingers into her hair and urged her to go deeper. She immediately took me as deep as I could go, sensing my urgency.

My feet were planted and my shoulders half buried in the couch as my ass was completely off the cushions, cock lodged deeply in this lovely creature’s throat. It didn’t take me but a few moments before I erupted, cumming down Hanna’s gullet. I could feel her throat work to swallow, massaging my now satisfied prick. I released my grip on the sides of her head and sank back down into the couch cushions. She continued to kneel, resting her head on my thigh. She let out a small burp, then laughed.

“Excuse me.” she said with a giggle. She reached over and regarded the stopwatch. Three hours and twenty minutes remained.

I stroked her hair. “That was wonderful. Thank you. I’d almost consider us even just with that and go home.” She looked up quickly at that comment. Her expression was one of brief fear and desperation. I realized that while I was temporarily satisfied, I’d done nothing help her with her ‘needs’.

“But don’t you worry. A deal is a deal. We’ve still got three hours or more that I get to use and abuse your body. Besides, I want to see what kind of noises you make when you come. And what you taste like. And how much you wiggle when you are tied up and spanked. And…”

She swatted my thigh and silenced me by quickly rising to kiss me.

“Make me cum, and you can do whatever you want to me.” she whispered.

With that, I took her by the hand and lead her to her bedroom. There, I stripped her naked, kissing as I went and laid her out spread eagle on the bed. It usually takes me a good twenty to thirty minutes to regain a good erection after such a performance. I spent the time exploring her clit with my tongue and her G-spot with my fingers, not quite giving her her wish, but very much building her anticipation.


Which brings me to now…. you remember- cock sliding into ass. As it turns out, my oral and manual manipulations did the trick. By the time I sank my newly invigorated cock into Hannah’s hot, wet pussy, she went off on me. A dozen or two strokes put her over the edge into orgasmic bliss. I continued to pump her for a good five minutes, until she begged me to slow down, near exhausted by multiple and near continuous orgasms. I suppose when you’ve had a dry spell for months, if canlı casino siteleri not years, a hard cock is a really good thing to have. Lucky her.

She may have been near comatose in her bliss, but I was only getting started. (Once resuscitated, I take a while getting to my second orgasm, see?) I flipped her over on the bed onto her knees and elbows. Settling in behind her, I gripped her hips and again sank my dick into her. A change in the ‘angle of attack’ creates new sensations.. Within a few dozen strokes she was panting and crying out again in pleasure with every thrust. After a number of reps with this particular exercise routine, I began to feel that familiar itch of a nearing orgasm. I pulled out with a wet ‘plop’.

“What is it baby?” she mumbled, her face in the sheets, her elbows no longer supporting her front half … only her ass was sticking up the air.

“How much time do I have?” I asked, eyeing my target.

“I don’t know, an hour or so… why? What do you want?”

“I’m close to cumming. I want your ass.” I said, hoping she was enjoying herself enough for me to do this.

She paused, obviously weighing her decision.

“Okay. Just start really slow.”

So I placed my rigid cock, slick with our juices and aided with a measure of my own saliva, at the entrance of her ass. Gently I leaned forward, trying not to use the rapid motion of my hips, but instead the slow weight of my whole body. Her sphincter held a moment, it backing up a bit into her body as my cockhead pressed it. Then, as if by magic, it opened up and accepted the intruder. My cock sank in past the head. Hannah took a deep, rapid breath. Then let out a hiss. I froze, neither pushing in, nor pulling out. Marveling at the unique sensation of a ring of pressure squeezing me just past my cock head.

“No, don’t stop, Joe. a deal is a deal.” she panted. “Just go slow. You’re enjoying this, aren’t you?”

I barked a quick laugh, then seized the twin globes of her asscheeks. Gripping and squeezing them, I thrust my cock another inch in.

“Hell yes, I’m enjoying this!” I glanced at a nearby stopwatch. “And I intend to keep on enjoying it for the next hour.”

An idle threat. I humped and hammered at her ass for at most two minutes more, slowly pushing her propped-up form flat. Her legs spread, my hands on her shoulders, pinning her in place with my cock in her ass. I came with a loud long growl. While I don’t think Hannah came from my buggering her ass, I certainly did.

After a moment or two lying atop her with my dick slowly wilting, I eased out of her ass and rolled off.

Hanna gingerly got up and made a bee-line for the bathroom. I called behind her. “Want me to stop the clock?”

“No, give me a couple of minutes, then you can join me.” she replied, as I heard her start the shower and close the door to the seperate cubby with the toilet.

I gave her at least three minutes, then joined her in the shower. Her hair was slicked back, water sluicing off her impressive breasts. She met me with a kiss and a soapy scrubby. After a number of rounds of kisses and you-wash-me and I’ll-wash-you, we ended up sitting on the floor, her back to me and my arms around her. The warm water cascaded down, not quite getting in our faces.

“How much time do we have left?” She asked.

“Oh, maybe fifteen minutes.”

“Good.” she said, sliding from my arms and turning around. “I don’t want you to think you’re getting cheated of your time.” With that, she lowered her lips to my flaccid cock and began to nibble and suck me. She also wasn’t without some tricks. When I was slow to stand at attention, she slid a soapy finger up my ass and gently massaged my prostate as she continuted her oral ministrations. Good thing P.E. teachers keep their nails short. I’ve had faster, harder, and kinkier blowjobs, but never had I had one that was totally focused on gently and patiently coaxing an orgasm from me.

When she swallowed and looked up at me with a smile, all I could say was, “Thank you.”

Drying off and dressing, me in my clothes, her in PJs, took the last minutes of the stopwatch. She showed me to the door, thanking me for the wine. I thanked her for the meal and her time. She kissed me on the cheek, before opening the door to the outside world, and said something to me that I’ll have to think about.

“You know, next month I’m going to have a number of odd jobs to do around the house… interested?”

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