This tale starts about six years ago when Steve began working at a very exclusive boarding school. He worked there for a couple months before he met a little angel named Maddie. She was the daughter of a woman who also worked for the school. When he met her she was in the fourth grade. He was working during the Winter break and all of the students were on vacation. He was listening to music while working and she popped her head into my office looking to see if someone was there. "Hi!" she said as she brought her scooter into my office and let it fall to the ground. "My name is Maddie! Are you Steve?"

"My mom sent me to ask if you could watch me for a little while. She has a lunch date and won't be back until 3:00."

"Sure I can do that. But I'm working. Can you keep yourself busy?" I said looking her over. She was a thin girl and long brown hair. She was wearing red shorts and a white tank top that snuggly fit on her showing her undeveloped chest.

"Sure!" She said as she grabbed her scooter and started off back into the direction she came. I knew her mom well. She was named Barb and she was the Principal's assistant. I went back to work and started thinking about Sadie and her Mom. About an hour later she came back much like she did before, letting the scooter fall as she entered. "Steve I'm bored," she said.

"Oh yeah?" I said. "I'm kind of busy but what do you want to do?"

"I dunno!" she said. "Can we play a game on your computer?" She went around the side of the desk and climbed in his lap and grabbed the mouse.

"Maddie, now I said I'm busy," he said. She had her ass on top of his cock and was wiggling around trying to find her favorite game site on his computer.

"Oh, come on Steve. My daddy always loves it when I sit on his lap and play video games. He says it makes him feel good when I do." She said.

"Oh yeah?" Steve replied. She didn't stop wiggling her butt. He looked down and her tight shorts were riding up her ass as she sat on him. She found the website and started playing a game where she dressed the girl and did her makeup. She was quite busy and she never stopped wiggling her butt on his crotch.

He felt himself getting aroused and said, "OK Maddie. You really need to get off my lap now sweetie. I'm getting uncomfortable."

"I'll say," she said as she looked over her right shoulder at him and continued grinding on his now hardening cock. My Daddy's thingy gets hard when I play on his lap like this too!" She said with a slight giggle. Steve didn't know what to do. Here he was with a cute nine-year- old beauty sitting on his lap masturbating him with her ass practically dry humping him. She dropped her hands down to the armrests of the chair and ground harder. His cock was almost fully erect now and the girl was rubbing his cock all the way up and down her butt crack.

Steve rolled his head back and groaned, as he was feeling really good now letting the little girl rub him off through his pants.

"Maddie, sweetie... I really need you to stop now!" He said as she continued humping him. "Something's going to happen."

"Are you going to cum Steve?" she asked as she turned and stopped. "I like it when Daddy cums in my mouth. Will you take it out and cum in my mouth Steve?"

"Oh god!" Steve said as he came in his pants right there. Maddie giggled again as she rubbed his cock again with her ass as she realized he let go in his pants.

Steve groaned as he came. Maddie smiled as she finished pleasuring the man with her body. "Did that feel good?" she asked as she stopped riding him.

"Yes sweetie. It felt great. Do you and your Daddy play games like this?" he asked.

"I'm not supposed to say. But we have a lot of fun," she replied.

"So, did you cum in your pants? It's such a waste! I love cum! You should have waited and put it in my mouth!" She said happily.

"Maybe next time Maddie," he answered.

"That's a deal! Maybe I'll come by your office again and we can play some more!" she said.

Maddie hopped off his lap and picked up her scooter and scooted out of the room. "Bye!" she yelled as she went out of sight. He smiled. He could not believe what just happened. Not only did the girl masturbate him to an orgasm she implied much more experience. He went to the men's room and cleaned up. He was a mess! He splattered his underwear completely covered in cum. He was sure they were a total loss so he stepped out of his pants, dropped his boxers and put his pants back on.

He continued his work as he returned to his office. About an hour later Barb came to his room and knocked on the door. "Are you free?" She asked.

Steve got nervous. Barb was Middies' mom. He got scared now. "Sure," he said.

"Maddie just told me what she did and I have to tell you I'm sorry." She said as she sat in the chair next to his desk. "Maddie is a very special little girl. She is quite advanced in many areas, as you may know. She seduced her Daddy about six months ago. He had her for a weekend and she did the same thing she did to you. Soon she was sucking his cock every night and every morning when she stayed with her Daddy on a visit. She told me after she started with her Daddy and soon she seduced me. She woke me up one morning. She had crawled into my bed and started sucking my nipples then before I woke up she was licking my pussy under the covers. Before I knew it I came in her mouth and she knew she had me."

"Wow." He said to the woman. "I don't know what to say!"

"I just want you to know that we are okay with it and it's not your fault. She is quite the minx. I was also asked to find out if you could watch her tonight?" She asked. "I have a date tonight and Maddie wants to go to your house instead of going to her normal babysitter. She thinks you guys would have more fun!"

"Sure!" Steve said. He was amazed. Here was this woman he knew for years and she was giving him the OK to have sexual play with her nine-year-old daughter. "What are the rules?" he asked.

"Just don't fuck her. Her Daddy is saving her cherry for a special occasion," she finished as she stood up and walked to the door. "Okay? Oh but I just mean her pussy. Her Daddy says she's really good and loves to get it in the ass!"

Steve was shocked again.