Playing with Sister and her Friend

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. “Jake” Sam began, “where’s the remote. Holly and I want to watch Hannah Montana.”

“Um, I don’t know. I wasn’t watching out here last. Did you try checking in between the cushions?” After I said this, Sam began digging her arms in between the couch cushions while Holly looked underneath the couch itself. As she did this, her sun dress came up a bit, enough for me to get a peek at her white cotton panties. I stared for a while, hoping Holly or Sam wouldn’t notice me looking. I looked to Sam, who was still searching for the control in the cushions. She was wearing a pink t shirt and baby blue shorts, so I was unable to see much of anything. I don’t know why I was so tantalized by the sight of a 9 year old’s underwear. Eventually, Sam got hold of the remote and turned the T.V. to “Hannah Montana.” The two sat down on the couch while I headed back to my room. I told the girls to stay inside and that if they needed anything, I would be in my room.

It was around 5:00 when I heard Sam call my name. I headed to the living room where I saw Holly and Sam on the couch looking quite bored. “We’re really bored Jake” Sam said. “Could you please do something with us?”

“Why don’t you just watch T.V.?” I replied, “Or play a game?” Although I was somewhat flattered by my kid sister’s asking of me to play with her, I wasn’t exactly an expert on little girl activities.

“We’re sick of T.V. and we don’t have any good games to play!” Sam complained. “Can’t you think of anything for us to do?”

Holly made her sad face again, her round lips curling up to form a cute frown. “Pretty please Jake?” Holly asked in such an innocent voice.

Now, I don’t know what came over me, but I as soon as Holly said that, I started thinking dirty thoughts. Here I had two cute, innocent young girls who would do almost anything that I asked of them. Sure, one was my little sister, but like any teenage boy, I was not going to turn down an opportunity to get some action. The wheels in my head started turning, and finally I thought of something fun we could do.

“Um,” I began, my heart beating faster, “how about a food guessing game?”

“How do you play?” young Holly inquired.

“It’s easy,” I said, “all you have to do is guess the food I put into your mouth. You’ll be blindfolded so you can’t cheat, and if you guess correctly three times, I will give to twenty dollars!” I knew that the twenty bucks would be the icing on the cake, but I was definitely willing to give up twenty dollars to get them to play the game.

“Cool!” Holly exclaimed.

“Okay,” Sam stated, “that does sound like a pretty interesting game.”

I told the girls to take a seat in a chair while I went to my mom’s room to retrieve a pair of her blindfolds she used while she slept. I hurried back, eager to begin the fun. When I returned, Holly and Sam were patiently waiting like good little girls. I put the blind folds on and asked if they could see anything.

“No” they both replied. To make sure they couldn’t see, I flipped them off. When they didn’t respond, I knew they were completely blind. I hurried to the kitchen to gather the first item for our game. I came back with a tray of various foods. I took the first item, a baby carrot, and held it in front of Sam’s face.

“Now before we begin, I have one more rule: you must keep your hands down and cannot use your teeth because that would give it away. Agreed?”

“Agreed! No hands or teeth” Sam responded. Holly asked, “How do we guess then?”

“Well,” I began, “Your just going to have to lick and suck and taste in order to guess.” I told Sam to open her mouth, which she obediently did. I held the carrot steady as she tenderly licked and sucked, her lips gently massaging the vegetable. After about ten seconds, I removed the carrot and asked Sam what she thought it was.

“It’s a carrot!” she exclaimed. “That’s one point for Sam!” I declared.

Next, I took a strawberry and headed for Holly, who already had her mouth open, awaiting her first food. She too took to sucking and licking the fruit with eagerness. I held the strawberry so close to her that I could smell her hair. It only took a few seconds before Holly took a chunk out of the strawberry and declared that it was a strawberry. I gave her a point but reminded her that using her teeth was not allowed.

“Oops,” She giggled, “I just love strawberries.”
My heart was racing as I took chocolate syrup and drizzled a good amount on my finger. I held it in front of Sam and she took my finger into her mouth, sucking and licking my finger. It felt sooooo good as she began twirling her tongue around my finger, eager to receive as much chocolate as possible.

“Mmmmmm” she cooed, “that’s chocolate. You know I love chocolate Jake!”

“That’s right! Alright Holly, your turn.” I said.

I repeated the process with Holly, using my finger covered in peanut butter this time. It took her longer to suck off all the spread, but she eventually got it all. I instantly became hard as Holly began bobbing her head on my finger, sucking and licking as she did so. I gave her a point and prepared for the final round. I reminded the girls that teeth were not allowed. My heart was racing as I second guessed myself. I decided that there was no going back as I slowly unbuttoned my jeans and unzipped my zipper. I readied my five inch dick and headed for my little sister’s mouth. I didn’t bother coating my cock as I figured these girls have never seen a cock, let alone tasted one before. Quietly I crept over to Sam, holding my dick in my hand, slowly pumping it.

“Open your mouth Sam,” I said. Slowly I guided my dick into her open mouth. When it was about half way into her mouth, I told her to begin guessing. Immediately her lips locked onto my cock and began sucking. My cock was engulfed in her tiny, wet, hot mouth. I grabbed her ponytail and guided her into a bobbin motion encouraging her to lick while she sucked. I knew I wouldn’t last long, so after about a minute of her sucking, I removed my dick and asked her what she thought.

“Well,” she began, “I’m not sure what it was. It tasted kind of salty, but the texture was weird. It was hard, yet really soft, and the tip seemed bigger than the rest.” My heart was beating faster now as I knew she was referring to the head. I was glad she didn’t suspect that she just had her big brother’s dick in her mouth, too. “I guess it was a…..banana?”

“No, I’m sorry sis,” I told her, “That was not a banana. Let’s see if holly can guess what it is.”

I moved to Holly who was eagerly waiting with her mouth wide open. My cock got about three-fourths of the way into her mouth, which was quite impressive for a 9 year old. I couldn’t believe how good it felt. Her head slowly bobbed up and down on my cock. I told her to increase her suction as I put my hand on top of her head and ran my fingers through her soft blond hair. I was feeling my impeding orgasm, and I decided to let Holly have a taste.

Quickly removing my cock from Holly’s pretty little mouth, I warned her, “Holly, get ready! This is a two-part clue. Soon, I am going to squirt something into your mouth. I want you to hold it there until I am done, and then I want you to swallow it okay?”

“Okay!” Holly exclaimed, excited to finish her food guess.

“Okay Holly, hold your tongue out and get ready for it!” I furiously jerked my dick and aimed my head for Holly’s pink tongue. I had to bit my lip to keep me from moaning too loud. I watched as the first spurt of thick white cum shot from my piss hole and landed onto the small girl’s tongue. Holly jerked a little at the initial contact, but to her credit held her mouth open for me. I watched as six roped of semen landed on Holly’s tongue. When I was finally done, I quickly pulled my pants up and told Holly to swallow. Holly closed her mouth and I heard a ‘gulp’ as I knew my semen was headed for her belly. I removed both girls’ blind folds and asked Holly what she thought it was.

“I’m not too sure,” she said rubbing her eyes, “it was a little salty and bitter, but strangely sweet. It was really gooey too. I don’t know what it was, but it tasted pretty good!” Holly said with a grin.

“Aww! That’s not fair, I want to try that gooey stuff!” Sam complained

“Sorry sis, those are the rules. It looks like nobody wins the money. But, if you really want to play again, maybe we can play after dinner.” I said with a smile.

“Well, I’d rather just taste that gooey stuff again” Sam said.

“Me too!” Holly proclaimed, “It was strange but it sure was tasty!”

“Okay girls, if you really want some more of that stuff, maybe I will show you how to get it around dinner time.” I knew in my head that this was going to be a very fun beginning to a very naughty weekend.

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