This is a long one with almost 11,500 words. This one I've spent some time on with editing and basically making it as interesting as I can, plus putting a good ending to it. That's the hardest part of writing, where to end them at. I wrote this as being the man in the story itself and that was hard to do. I've written them before in the past and it's harder that you think it is. Anyways, I hope you will enjoy this as much as I enjoyed writing it. :)
Chat Room Babysitter
I couldn’t believe I was staring at a picture on my computer of my 19 year old babysitter's naked pussy.
Leaning back behind my desk in my home office, maximized on my monitor, was a picture of Candy lying on her back nude with her legs spread, and a perfectly shaved, glistening pink pussy pointed at the camera. Wow. I mean – wow!
It was the second of the fifteen pictures that I'd opened. The first pic, file name .ME, had a nice smiling photo of her sitting on the bed wearing a bra and panties. And, of course, not just any bed -- MY BED. Well, my wife's and mine. Stunned at discovering fifteen .JPGs in a folder marked "PICTURES," which of course I hadn't put there myself, I raced to open the picture named PUSSY.JPG. And there was that teenager's cunt.
I closed the photo and hit "OPEN," and looked at the other names of the pics in the folder. TITS. TITS2. FINGERSINSIDE. PUSSYCLOSEUP. ASS1. ASS2. TOPLESS. Holy shit it was a smorgasbord of porn, and our three-door-down neighbor's daughter was the chef.
Clearly, she'd taken the photos in my -- our -- bedroom sometime when the kids were asleep. I couldn't wait to see the rest. There were a particularly enticing couple of them that I opened first -- DILDO1.JPG. And if this miracle wasn't enough, there was a photo of Candy spread on MY bed stuffing her cunt with MY WIFE'S dildo. I mean are you serious? OK, technically, my wife Gina hadn't used her dildo (as far as I knew) for a few years. Honestly, the only action I know it's seen has been the couple of times I brought it to rendezvous with chicks I'd first met on the Internet. But it did my heart proud to see Candy putting it to good, deep, and wet use.
OK, it's not just that I found on my computer Candy’s nude pics of her fucking herself on my bed. You have to know Candy (and, right now, I'm sure you're wishing you did). She's, well, a prude. She always wears loose, baggy sweatshirts or blouses, nothing form-fitting ever, she has thick-rimmed glasses, keeps her hair pulled back behind her head. I swear, until I saw that first nude photo of her, I had no idea she had such above-average proportions -- looks like 34b or 36c chest over maybe a 24 or 26 inch waist, and 34 or 36 inch hips.
(When I pulled up ASS2.JPG, I got to tell yes indeed, it was a nice round butt.)
But her, um, prudishness is perfect. My wife first used her about five years ago, and in the last year since Gina has been staying late at the office for presentations and doing overnight trips to Corporate headquarters, I've had to fend for the kids myself most of the time. Working out of the house helps, but Candy has been making good money playing pseudo-mom for an hour or two each day, or for a few hours when I have to go out too. (Ok, "have to go out" means, have somewhere else to be, you know, get it?)
So, it being late and the kids were asleep, and my wife was on her way home, I raced to pull out my cock and I stroked off to a powerful orgasm staring at Candy's body. I put everything else out of mind and just stared at that young pussy taking a thick dildo and her fingers.