Babysitter's Secret... - Sex Stories

Babysitter's Secret...

... thing. As a single father, my number one mission is my kids. They were having a rough time adjusting to the divorce, so I didn't see the need to complicate anything by bringing strange women around. I've got needs, sure, but I sublimated them for the good of the kids. Maybe I was in denial and avoiding dating, but I'd rather spend an evening watching Spongebob than trying to get into someone's pants.

So, cue "Cat". The older man-younger woman/babysitter trope was already a staple in my fantasy arsenal. In the 5 minutes I had alone each day, in the shower, I exercised my thoughts about Cat. She was 19 as we know. About a head shorter than I was. She was lean, and had a cute, soft - somewhat boyish face. That was no problem for me, I liked "handsome" women and tomboys. She was also a snappy, if not provocative dresser. When I'd seen her in the grocery market, she was wearing a short white pleated skirt, black thigh highs, chucks, and a cute top. She had on bubble-gum pink lipstick, and her hair was done in braids. Instant hardon. After our introduction, I would spend my morning shower-time jerking my cock to one fantasy after another about her.

But there was something off about her. I could swear I saw an Adam's Apple, but I wasn't too sure. And in subsequent chance meetings, I noticed that her hands were a bit larger than they should've been for her frame. I reasoned that she was probably still growing, but sexuality being what it is these days, who knows.

The ...

... question started to eat away at me. I was trans and CD friendly. I'd had some strange experiences as a younger man, and I was always looking to replicate them. It was the primary reason why my wife had left me. I confessed to her about my experimentation, and she turned immediately cold. She was convinced I'd "never be completely hers" and eventually seek out gay relationships. I tried to convince her that it was just a period of my life that had no bearing on our marriage. We'd had a good sexual life together. I never disappointed her. So, what was the big deal? But, she left. Doesn't pay to be honest, I guess.

I was starting to become obsessed with Cat. I was thinking about her constantly. I knew a real relationship with her was never going to be possible, but I wanted to push the envelope and see where things could go. I also wanted to figure out what was between her legs.

Around this time, I decided I needed a sexual outlet and started to date. I hired Cat as a baby-sitter on these occasions. I decided that I wasn't going to try and fuck Cat. That'd be just too weird. She was old enough to be my daughter for chrissakes.

So, Cat would come around and sit for my kids. She always had a smile for me. When she'd look at me in the eyes, it never failed to produce a blush. I also had her run errands for me. At $20 an hour, she was eager to help.

On one particular occasion, I couldn't take it anymore. I was going to make a move on Cat, or at least determine "what she was". ...