The Dad and The Sitter Pt. 01

(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?

Me: Yes, but not everything. It just looked like you were sucking his cock. Were you?

Her: Yes.

Me: Did you guys fuck?

Her: No we just made out. We never had sex.

Me: Is that why he broke up with you?

Her: Yeah. Basically.

Me: Are you a virgin still?

Her: No, I had sex with a guy last summer. We did it a few times.

Me: Why didn't you want to fuck your boyfriend?

Her: I don't know. I guess wasn't into him really.

Me: So you just suck guys cocks?

Her: Yeah I guess so.

Me: How many guys have you given head?

Her: Four.

Me: What if I wanted you to suck MY cock?

The line had really been fucking crossed now. She stared back at me thinking about my question, a little bit shocked by it, but she wasn't jumping out of the pool and running home yet to tell her parents. "Yeah, I think I would" she replied. My cock had never been harder in my entire life. "Let's go in the pool house." She swam over to the edge and I leered at her perfect ass as she exited the pool. I followed behind her. My cock pointing straight up to the heavens.

We went into the pool house and I shut the door behind us. "Do you wanna see what you do to me?" I asked. She nodded. With that, I slid my trunks off and let them drop to my ankles. My thick hard cock sprang free, just hanging there for her to look at. I grabbed it and stroked it a few times and then told her to touch it. I replaced my hand with hers and i leaned in and kissed her while she stroked me. I sat down on the loveseat and had her stand in front of me. I reached for the little ties of the sides of her bikini bottoms and undid them and watched her little bottoms fall free, showing off her smoothly shaved little pussy. I put a hand between her legs and she was wet and hot. I asked her if her boyfriend ate her pussy for her? She said no. I leaned my face forward and grabbed her ass with both hands and pulled her towards me and started licking her sweet little cunt. She moaned "Oh fuck". I was enjoying her taste but this wasn't what I wanted right now. I stopped licking and then leaned back in the loveseat and told her to sit beside me. We kissed while I played with her pussy and felt on her little tits. I told her to show me how she sucks cock. She leaned into my lap and put her lips around my shaft and slowly let is it slide into her mouth. Fucking hell, this was heaven. She sucked me really slow but used lots of tongue, and eventually she got my whole cock down her throat. As she sucked my cock, I fingered her cunt and even teased her asshole a little bit with my thumb. She stopped for a second when I slid my thumb all the way into her ass, but I told her to get back to sucking and she did as I said. I continued to thumb fuck her ass which sped up her oral efforts. I knew I was about to cum and warned her, but she kept going faster and faster, even as I started to thrust my hips up and began to facefuck her. I came harder than I could ever remember and she swallowed it all. I sat there absolutely spent with my thumb still in her ass as she kissed my cock and my stomach. I told her how good she was and how much I wanted to do everything with her. We kissed for a little bit until I reminded her I needed to go check on my youngest again. I got dressed and went into the house and left her to get her self together.

There was no going back now. I'd just changed everything. This was just the beginning.