Babysitter's Secret... - Sex Stories

Babysitter's Secret...

NOTE: I published this story under another Literotica ID: MonkeyWrench00. I'm sharing it here too. (I use this ID for a more feminine persona when I chat. If you see me in the CD chat room here, hmu!)

This piece was inspired by a chat I had with Cutesissytoy! Thanks for the imagination fuel!

This, is a tale as old as time: Single suburban middle-aged man meets hot young girl. Hot young girl babysits for aforementioned man. Middle-aged man fucks young girl, finds out she's a crossdresser, keeps fucking her.

But when it all started, I wasn't aware that any of this was going to go in that direction.

I met Cathy (we'll call her "Cat") shortly after I moved into my new neighborhood. I was recently divorced, but fortunately I was in good enough shape financially, that I could afford a nice new house, in a nice, secluded neighborhood. I had a nice, large lot that kept me at a pleasant distance from my neighbors, there were lots of trees, etc. What more can you ask for?

I was out grocery shopping one day with my kids in tow, and they were brimming with energy. I'd been burning the candles at both ends recently. My wife had taken off with some prick asshole, and the judge awarded me custody. I must've looked beleaguered because the cutest, sweetest girl came up to me and introduced herself while I was rapidly putting back copious amounts of junk food and candy that my kids had taken off the shelves.

"Hi Mr. Carpenter! Looks like you've got your hands full. Need any ...

... help with your kids?" I looked at her quizzically, and she continued, "I'm Cat! I live down the street. My parents are the Findley's." Ah. The Findley's. They had a pretty sweet Tudor. "I go to a local college, so I'm staying with them right now."

"Well Cat, we're just wrapping up here, but if you ever want to do some babysitting, let me know."

She beamed at me, "I'd *love* to." We exchanged contact information, and off I went with my little monsters.

Now, the full impact of this exchange took a little while to settle in. Cat, to put it lightly, was fucking hot. And the fact that she was in college, sent my head spinning. She was legal. Now normally, I don't pursue younger women (especially not that young) and I barely fantasize about them anymore. What's the point? From the perspective of a young woman, I could see myself as a gross older man. Nothing is more pathetic than an older guy who thinks he's going to score with a younger chick. That's Penthouse Forum shit. Doesn't really play in the real world. Besides, younger chicks don't get your jokes or cultural references.

Now - let me clarify - I'm not a "gross" older man. I'm in my early 40's. I exercise. I'm in good shape. I'm still rocking a 34 inch waist, I've got broad shoulders, a square jawline, and all my hair. (Alright, it's thinning just a little. I also have a 10" dick, and no problems getting it up. Women my age dig me, and if I had the time and energy, I'd be knee deep in pussy.

But that was the ...