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.
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'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. (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?"
