Ruby was her name. Her mom must have known how sweet those ruby red lips would be 19 years later. She was working as a babysitter needing money to finish her travel to Hollywood. One Hollywood agency had promised her modeling work if she could get there. I was doubtful but she sure believed it.
I had enjoyed fucking our last babysitter Kelly for months. Kelly was a cute little brunette teen with decent titties and the tightest little cunny. At least it was before I gave it the daily stretching. Now Kelly was pregnant and gone for a few months and we needed a new babysitter.
Ruby, a real beauty showed up at the door. She had come out from New Orleans and was staying in the apartments near town with her older sister. Only 19, with a portfolio of pictures and plans to be famous she was working her way to the Hollywood lights. She ran out of cash and was stuck in this small town. Then sent her to us for daycare.
After she arrived I skipped work early every day just to stare out the window as she walked by the pool. She was a tall beautiful young woman. She stood 5 foot 9 with an amazing natural set of breasts. Her hair and makeup were always perfect and she walked tall and proud like a model. My cock would get hard watching. I had to find a way to play with those tits. My dream was to breed her just once before she left.
Ruby wasn't dumb like Kelly. She was smart with big dreams. I really didn't expect to seduce her. I knew a 35 year old man with two kids would not be her ideal "fling." Girls like her were usually working on advancing their careers fucking a producer or rich exec, not fucking a small town married man. I needed a plan, one that would appeal to her.
I was watching her by the pool while she worked the phone. I knew she was working on getting back on the road so it was time to make my move. Sitting down by her I looked into her beautiful brown eyes and her long dark brown hair while I struck up a conversation.
She had been dating some college jock while in high school. Since she left him she's had no boyfriends. That meant weeks not getting laid. Most important though Ruby was worried her dreams were disappearing along with the modeling job waiting for her. Stuck in this town, with little hope, she wasn't even old enough to be a cocktail server.
"No modeling jobs here?" I asked, knowing the answer.
"There's nothing here," she said, dejected.
"Too bad, I know you'd really do well in Hollywood. You're very beautiful," I said knowing all women liked hearing praise. "Any photographer would pay good money for a shoot with you."
"Not around here," she said, "no modeling work in this place. I was hoping to at least add some pictures to my portfolio."
"Well," I said, "I do some photography, I could pay you and maybe give you some shots for your portfolio."
She was quiet. Then asked, "Like how much?"
"Well," I said, making my first move, "I'd like some photos for my private viewing. Maybe 500 bucks for some nudes?"
I knew what $500 meant to a girl making 60 bucks a day babysitting. $500 could get her to Hollywood. She acted hesitant.
"I'm sorry," I said, "I didn't meant to..."
"Oh no, no, no problem,... I'll do it,..... yeah, I mean for $500 I'm in." She was seeing her ticket to Hollywood. Phase one of my plan had been a perfect success.
That Saturday my wife left at around 3 that afternoon to her mothers. Ruby came over shortly after that. She had her modeling case with makeup for the shoot. A friend lent me a real quality camera and I practiced all morning so I wouldn't look too amateur. Of course I had to promise him some copies.
Our first plan was some swimsuit shots. She loved to pose. I poured some nice wine and we went through a lot of film.
It was getting dark so I suggested some nudes in the pool house. I had been waiting for her to take off her suit so I could feast my eyes on her beautiful breasts.
"Let's get some shots without the suit," I said as we entered the pool house.
"I wanted to ask," she said, "you are going to pay me today, aren't you?"
"Oh yes," I said and I reached in the drawer for the envelope. I had it stuffed with cash and she watched closely as I counted five hundreds off. I made sure she saw there were plenty more in the envelope.
"Thank you," she said smiling and all bubbly and put them in her case. I fumbled with the lights to act professional then I stopped to watch her undress.