Babysitting Amanda

Every night after my first experience with Amanda, I found myself jacking off to memories of her. She was the first person I had ever done anything sexual with, and I was desperate to see her again and allow things between us to continue.

Let me introduce myself. My name Jake and I am 16 years old. I was your classic horny teenage guy. My hair is dark black, which goes well with my brown eyes. I’ve always been slightly fit, never working out yet somehow keeping myself in shape through basic exercise. I’ve never managed to have a steady girlfriend, so often I fantasized to thoughts of the busty girls from around my school. All that changed when I met Amanda. After my experiences with her, images of her sexy, then 14 year old body filled my mind every time I masturbated. I must have cum literally gallons in the months after we meet, always looking forward to a time when we would see each other again.

The opportunity came during a phone call from Amanda’s mother. She had found herself in need of a babysitter one day, and Amanda mentioned me. She got my phone number from Tom’s parents and asked me to babysit both Amanda and her younger sister, Becky, who was twelve As soon as she mentioned Amanda’s name, I was on board with the idea and canceled all other plans for that day. I would again be needed overnight- from 10 am Monday to 6:30 pm Tuesday. It turns out that her mom was attending a business meeting until late and would sleep in her office. Not that I was complaining.

At exactly 9:55 am Monday I got to their house, just down the street from Tom’s. I knocked, and Amanda’s mom soon answered. She was a plain sort of woman in her 40s. Her hair was brown, unlike Amanda, who was blond. She quickly ushered me in and briefed me. The girls were allowed to go to the playground, but could not leave my sight. They could have friends over- however many I was comfortable with in the yard but only two inside. Both girls were to bath that night, but Amanda could take a shower while Becky took a bath. Considering the fact that I was a guy, she said that Becky would be more comfortable if Amanda bathed her. “No problem” I said. “I understand”. After giving me a list of emergency numbers, she left me there and went to her bedroom to wash up. Amanda, who had been watching the whole exchange, seemed to float over into my arms. She snuggled her head onto my shoulder and said “I’m so glad you’re here, our old babysitter wasn’t nearly so hot.” Smiling, I turned to her and whispered “I think about you every night, I’m so glad to see you again.” She smiled, a gesture that warmed the very depths of my heart and existence. I kissed her then, a soft but passionate kiss on her soft lips. We held each other for a few more seconds, but broke apart at the sound of footsteps. Becky walked in. Like her mother, she had shoulder length brown hair. Her eyes were a soft blue, and she wore a baggy T-shirt over a pair of hand-me-down blue jeans. Seeing me, she drew back slightly. “Its ok Becky”, Amanda said with a helpful-big-sister sort of smile. “Jake here is cool”. I gave Becky a small, friendly smile, and was glad when she smiled back. Amanda’s mom reappeared, and after addressing her daughters and wishing us a good night, turned out the door and left. As I heard her car pull away, I asked Amanda what the girls normally did at that time. She suggested the playground, and I agreed. Becky had to change into a tighter shirt that wouldn’t flop down on her easily, and we were off. At the playground, several of the neighborhood boys recognized me from Toms and waved. They didn’t dare come over and talk, lest their parents suspect something. I kept a close eye on Becky the entire time, while Amanda went over to her own friends. I recognized Jessica and Katy and waved. Giggling, they waved back and returned to their activities. Becky climbed up onto a squat pair of monkey bars, and I stayed near in case she fell. After climbing across once, she began to horse around on the bars, pulling herself up on top. Locking her legs tight around the bar, she let her chest fall down towards the ground until she was hanging upside down. She looked silly for a moment, until her shirt billowed down and covered her face. She wore nothing underneath it, and her young, flat chest was exposed to the world. I scrambled over and picked her up. She let go off the bars and proceeded to pout as a set her down. I told her: “You can climb up again, but you’ll have to tuck your shirt in first”. I demonstrated how, and she did so before climbing back up into the same position. Becky played on the bars until about 12, when I decided it was time for lunch and a nap. Gathering Amanda from her gaggle of friends and a disappointed Becky from the monkey bars, I took them both home and fixed sandwiches. Afterwards I had to put Becky to bed. Needless to say she did not go quietly.