(the girl in this story is 18 years old)
When I'd met her, she was just a kid. She was the daughter of one of my wife's coworkers. We hired her to babysit our children from the time they got home from school until we got home from work. It was 4 days a week (mon-thurs) plus the occasional weekend night when the wife and I went on a date or had a work function. I was typically the first parent home, and so I usually had the most one on one interaction with her. She was a cute girl: tall for her age (almost 5'10"), with long legs, small breasts, a perfect teenaged ass, and just the most beautiful smile. I felt like such a fucking creep. I WAS A FUCKING CREEP.
She and I always had pretty open conversations whenever we had our time alone. She liked talking about her life and I liked listening and reminiscing on my own youth, before I got married and became a middle aged father of 2. Nothing truly inappropriate ever happened between us...not until her senior year. That's when SHE got a boyfriend and I got VERY jealous.
She asked me one afternoon if it was okay to invite her boyfriend over to swim in our pool. We had always let her use it and were fine with her bringing over a friend or two, but she'd never brought a boy. I said that was fine, as long as she promised not to get too distracted and still watched the kids. I guess I wasn't really prepared for what I was gonna feel like when I saw her with him.
I came home from work and they were in the pool together. She was playing with the youngest in the shallow end while her boyfriend was doing cannonballs with my oldest. When they got out of the pool, I was shocked how skimpy her bikini was. Normally she wore a one piece, but on this day she had a bikini with those little tie things on the sides, it wasn't quiet a thong but it showed off most of her ass. I caught him giving her butt a squeeze while they were drying off. When they left, they sat in his car for a really long time. He had parked on the street at the end or our dead end road. It was a pretty secluded spot as far as places in a neighborhood went. From my kitchen I could see them though. Not enough to tell exactly what was going on in his car, but enough to tell that her head was in his lap. Jealously and desire filled my mind and my cock.
A few weeks after that I came home to find her swimming alone in the pool. My youngest was watching Wall-E for the 800th time and my oldest was apparently at his friend's house. I checked on the youngest and made him a snack and then went out to the pool to let the sitter know I was home and that it was okay for her to leave. She asked if she could swim a little longer and i said sure as long as i could join her. I put on some trunks in the pool house and saw her clothes in a pile. Some jean shorts, a band shirt, her bra, and a tiny little white thong. It made my cock twitch.
I got in the pool and we swam and chatted. Eventually the subject of her boyfriend came up and she said they weren't dating anymore. He had broken up with her and was dating a different girl in her friend group. I told her he was a fucking idiot to dump her and how there's no way i would have broken up with a girl as hot as her when I was in school. "You think I'm hot?" She teased. I got stone serious and said "No. I think you're absolutely beautiful and I was honestly really jealous of him." Welp, i had officially crossed the line. I was expecting her to freakout but she didn't. Instead the electricity in our conversation changed. She wanted to know more details about my jealousy. I said i saw him grabbing her ass in that little bikini. She asked "You like my ass?" I said I loved it. And then told her I saw them in the car making out and it looked like she was giving him head.
Our Conversation went like this:
Her: Oh my god, you could see us?
