Playing with Sister and her Friend

Let me tell you about myself: My name is Jake. I’m 15, 5’11’’ 145lbs with brown hair and green eyes. I happen to have a sister, whom this story is based upon. Her name is Samantha, but everyone just calls her Sam for short. She is 4’9’’ and 9 years old with shoulder-length straight brown hair and brown eyes. We got along okay, but it wasn’t until one weekend that our relationship became inappropriate.

It all started when my mom asked me to babysit Sam for the weekend. She was going on a business trip and would leave Friday afternoon and come back Sunday night. “I’ll watch her” I said, trying to be helpful. “Thanks,” she retorted, “I can always count on you to look after your baby sister. And, for being so helpful, I’ll give you fifty dollars for the job!” (Sweet! Fifty bucks to watch my little sister for a few days.) Fifty bucks was a lot of money to me, and I didn’t mind not hanging out with my friends this weekend because of it.

As mom was doing her last minute packing for her weekend business trip, Sam came bouncing in from playing outside, her ponytail swinging gently as she danced into the house to say goodbye to her mom. However, she wasn’t alone. Her friend from next door joined her. Her name was Holly. She was also 9 but a little shorter than Sam. Her skin was fair, as was her hair, her wavy blond hair swayed passed her shoulders. I first noticed Holly when her family moved in a few months ago. She was cute, but I didn’t think of her as anything more than my kid sister’s friend. (How things would change!)

“Mom?” Sam began, “Holly’s parents are going out too and I was wondering if she could stay with me and Jake until they get back.”

Mom hesitated, “I don’t know about that. I don’t think her parent would allow that.”

Holly perked up, “No, no, really! They said it would be okay. They even gave me fifty dollars to give to you for the trouble!”

“Well, I guess it’s okay with me, as long as it’s okay with you” Mom replied as she turned towards me. Holly and Sam also looked towards me, and soon, I had three pairs of eyes peering at me, waiting for me to respond. I took one look at Holly and Sam’s faces. They were both doing their best “sad puppy dog faces” and their eyes got really big. I really didn’t mind, especially if I was going to get an extra fifty bucks.

“Sure, I don’t mind” I replied.

“Great!” Sam cried, “Let’s go to my room Holly” As they both walked away, I couldn’t help but notice that Holly was developing quite a nice little bubble butt under her yellow sun dress. Sam too was starting to grow, although her ass wasn’t nearly as thick as Holly’s, still nice though for a girl her age. This was the first time that I had thought anything sexually towards the two of them, but it surely wouldn’t be the last.

As mom was heading out the door, she said, “Jake, there’s money for pizza on the fridge. Try not to let the girls get too drunk while I’m gone!” she joked. Something about her words really got me thinking.

As I Headed back into the living room, I noticed that Holly and Sam were both walking around the room.