Maddie Ch. 01-08

Disclaimer: All persons involved in this story are 18+. This is my first story, so please bear with me.

Chapter One: From A Distance

I was out on my porch looking at my phone, watching the traffic go by. It was 5:30, I knew she would be by anytime now on her way home from soccer practice. Just as I was checking the time again I heard the familiar sound of a bike quietly whirling down the sidewalk. I peered up to watch her on her voyage home, which happened to be right next to my house. Maddie smiled as she rode past my porch and gave me a quick little wave. I waved back and watched her ride into her driveway.

Short denim shorts, concealing her tight little butt leading down to her white legs in blue sneakers. A red t-shirt with a bear on the front of it, that would ride up past the small of her back with every turn of the pedals, revealing just a sneak peak of bright pink underwear. Smooth brown hair in a ponytail bouncing up and down at every bump in the sidewalk.

She leaned her bicycle against the garage and headed inside, with a cute little perky bounce in her step. I couldn't help but fantasize about her little perky breasts and her skinny little body being sweaty all over. All I could think about was ripping her tight little jean shorts off and getting a peek inside those pink little panties. I noticed a large bulge forming in my pants.

Maddie and her family moved in about 5 years ago, and I've developed a large crush on her. She has such a lovely bubbly personality and always a pleasure to talk to. She loves to walk my dogs for me while I'm at work and she even housesits for me sometimes when I'm away. It's all I can do not to think about her all day, I try to behave myself because of the large age difference. Sometimes she'll play just a little flirty and flash me a quick smile, it makes me a bit lightheaded.

It was 7:00, I was sitting by my back window overlooking the yard when I saw Maddie come out of her house. Now she was wearing a pair of tight worn out jeans with no belt and a yellow shirt with spaghetti straps. She went over to their small garden and leaned over to pull some weeds. Again I could see the small of her back and some cute pink fabric sticking up from her butt. It was humid out and the sweat was pouring off her as she pulled weed after weed. She bent over again this time facing my line of sight, I could see she was not wearing a bra and I could see the tops of her small, glistening, sweaty breasts. I found myself unzipping my pants and taking out my penis. I started to rub myself as she used her shirt to wipe the sweat off of her forehead, revealing her cute little belly button. All I wanted to do was bend her over right there, take her sweet little boobs in my hands and press my hard cock against her soft small ass.

I went upstairs to my room, as I was getting ready for bed I noticed a light come on in the room directly across from mine in the neighbor's house. I watch as Maddie goes into her room, she looks tired and ready for sleep. She starts looking through her dresser and eventually pulls out a pair of pajama pants and a tank top. She sets the clothes down on her bed and starts sliding off her sweaty top. It stuck to her as she tried to pull off the tight shirt. First revealing her belly button then reaching the lower parts of her tiny breasts, then I could see her little nipples, they were perfect and I wanted them in my mouth so bad. She finally gets the shirt off and tosses it to the side. Then she starts unbuttoning her jeans. She slowly unzips them and starts to wiggle them down.

As she is pulling the tight jeans off, her pink underwear starts to go with them revealing the top of her tight little butt. She quickly pulls the underwear back up and continues pulling her pants off until they hit the floor. She took her feet out of the pants and kicked them to the side. Now she stood there with only her small pink underwear on and her perky little breasts still glistening with sweat. I felt like I was about to explode as I watched her perfect petite young body stand there. She had slight tan lines around her breasts. She grabs her pajama pants and slips them on concealing her butt and that cute little pair of pink underwear. She grabs her tank top and slides it over her perk, erect, white little breasts. She then turns off her light and I am left to my own imagination.

Chapter 2: Pool Party

On my way home from a long day at work, I kept thinking about the other night and seeing Maddies petite slender body naked for the first time, even if it was from a distance. She has such a perfect little body for a girl her age, all I could think about was kissing her, feeling her tongue in mine while I run my hands down through her hair and on to the top of her back. Kissing her neck while my hands found their way to the small of her back into the waist of her tight jeans, making her moan ever so softly while my erection grows in my pants...

Then I come back to reality and realize it could never happen, it would be taboo, I shouldn't even think about it, it's wrong. I tried to think of other things for the remainder of my ride home.

I pull into my driveway and as I get out of my car I see my neighbor Ray start walking over to greet me. Ray lives two houses down from me, on the other side of Maddie's family's house. Ray was a few years older than me, with a good job and a nice house, and an all around good guy.

"Good afternoon Ray," I said.

"How are we today?" He replied.

"Not too bad, better now that I'm home"

He laughed, "What're you doing this Saturday?"

"I'm not sure yet, probably just working on the house" In all reality I'd probably be binge watching some sitcom, but he didn't have to know that.

"We're having a neighborhood party at my house, we'll have plenty of food, plenty of beer and the pool will be open."

"Maybe I'll swing by, thanks for the invite!"

"You better, all the other neighbors are coming"

"I'll see you there," I said as he walked away giving me a thumbs up.

As I was thinking of who would be there, I started thinking about Maddie and I hoped she would come with her family and maybe she'd even bring her bikini. Now I'm excited, maybe too excited.

I had on a pair of swim trunks and a sleeveless shirt, as I stood at the party making small talk with the neighbors, trying to hide my disappointment that Maddie wasn't here yet. I watched as some of the kids played in the pool and had a couple of beers and one burnt hot dog.

"Hey guys, glad you could make it!" I heard Ray say. I turned to see who showed up and saw Maddie and her mother walk in. I made eye contact with both of them and gave them a little smile and wave as they made their way towards the crowd. Sarah was wearing jeans and a white t-shirt.

Sarah is Maddie's mother, and shares many of the same qualities as Maddie. She's 34 and just as slender as the day she turned 20. Unlike Maddie Sarah has short blonde hair and dark blue eyes, her breasts are slightly larger than Maddies and she maintains a very athletic figure with a nice round butt.

Maddie wore a small pair of denim shorts that hardly covered her butt cheeks, and a white tank top that you could see her bikini sticking through. She said hi to a couple of the neighbors than quickly made her way by the pool. She slid her tank top over her head and revealed her red bikini that had two small straps going over her shoulders and looked like it could fall off at any moment. She then unbuttoned her shorts and started shimmying out of them. She managed to get them off and through them on an empty chair. Her bikini bottoms matched the top and revealed the sides of her white little butt cheeks, when she turned towards me I could see the slight outline of her vagina through the light red fabric.

I could feel myself start to get hard and figured I better hop in the pool so no one would notice. I quickly threw my shirt and phone to the side and made my way in. Maddie at this point was already in and was trying to get people together to play water volleyball. She managed to get enough people together, including me, and we started to play. I managed to get on Maddie's team and had a hard time keeping my eye on the game.

Everytime she jumped to get the ball her buttcheeks rose above the water and then quickly disappeared again, every time giving my boner another length of duration. One time the ball was hit right between the two of us and we both went to get it. As I ran forwards to get it, she moved backwards until we bumped into each other. My semi-hard cock slightly grazed her wet tender butt making her slightly gasp and fall. I quickly grabbed her from tripping over my feet and sort of picked her back up, holding her waist to steady her, I could feel the fabric of her bikini in my hands and her warm soft flesh felt so smooth. She sort of giggled and apologized for bumping into me, and I let her go, running my hand slightly down her hip first.

The game didn't last too much longer after that and we all got out of the pool to dry off. I watched as Maddie walked over to her towel, she was dripping wet with her bikini clinging so tightly to her body, leaving little to the imagination. Her small body was so beautiful in that wet red bikini that my cock was throbbing with pain, I had to excuse myself and head home before anybody noticed. As soon as I got home, I took my cock out and rubbed it with the thoughts of Maddies wet smooth butt rubbing against it still prevalent in my mind.

Chapter 3: Touched

It was Sunday Morning, I had called Maddie up to have her help me paint my kitchen, the house was a mess when I first bought it and have slowly been fixing it up. Maddie likes to do odd jobs and enjoys the money she gets from them, so I decided to have her join me. I told her to dress in old clothes as painting can get very messy and sweaty. I got up early so everything would be set when she got here and we could go straight to painting.

I heard a knock at the door, I quickly combed my hair and straightened my shirt as I made my way to the door. I opened the door to Maddie standing there, eager to help as always, with a big smile on her face.

"Good morning!" She said

"Good morning, Maddie" I Replied, as she walked in past me, giving me a whiff of her fruity shampoo.

She was wearing a pair of faded jeans with a hole about 3 inches down from her waist on the front, and another hole just below her butt on the back. She had her blue sneakers on and white socks, I couldn't help but admire how beautiful her legs looked in those jeans. She wore a plain white T-shirt that barely came down to the top of her jeans. Through the t-shirt I could see she was wearing a purple bra. She had her smooth brown hair in a ponytail that did a cute bounce with every step she took.

My german shepherd Miley, came running up to greet Maddie. She just adores Maddie and the feeling is mutual.

"Miley!" she shouted as she kneeled down to pet the overexcited dog. Her shirt rode up enough to reveal the top of her lacey underwear which happened to match her purple bra. She looked so small and cute down there playing with the dog. I yearned to pick her up and carry her to my bed.

"Ready to start?" I asked,

"Sure am!"

"Okay cool, everythings all set" I said while handing her a paint brush and opening the paint can up. We started painting, one stroke of the brush after another, we made some small talk, and soon were talking about more in depth things.

"All the boys at school are so immature, it makes me not even want to date," she stated.

"Yeah I get that," I replied while slightly smiling to myself.

"I just wish there were more mature boys, I've never even kissed a boy yet!"

"Really?"

"Why does that surprise you?"

"Well you're just such a beautiful young lady, I figured every boy would be trying to kiss you."

Her cheeks became red, she smiled and replied, "Thank you, but I don't think I'm very attractive to guys, none of them ever seem to talk to me."

"Well that's just because there immature and probably intimidated"

"Intimidated?" Her forehead scrunched, looking confused.

"Yeah, look at you, your'e fucking gorgeous, you have beautiful brown hair, sparkling brown eyes and just a angel of a smile."

Her blushing intensified. "What about my body?"

Now I was blushing, "Well you have a very good figure."

She continued to look at me, so I continued, "You have the perfect build, your very petite and cute, trust me you're perfect."

"I wish I had bigger boobs though, mine are so small"

"Your boobs are perfect, trust me, they're nice and perky."

She gave me a big smile, still blushing, and we continued to paint until I looked at my phone and saw it was noon. I asked her if she wanted to go get lunch somewhere, and she said she was starving. So we cleaned up our brushes and headed to go get something to eat.

We went to Subway and each got a sub and sat down to eat. We sat across from each other at a small table. We kept staring into each other's eyes and then she started playing footsie with me, giggling the whole time. She took her foot and ran it up my inner thigh until it reached my crotch and I instinctively tightened my legs around her foot holding it against my semi hard cock. She gave it a soft tap, making my dick throb with excitement. I let her foot go and then ran my foot up the same way up her thigh. She also tightened her grip on my foot and would ot let go. I used the tip of my shoe to rub against her crotch and she gave a soft moan, I continued to rub her crotch softly and she started to squirm and moan. She was getting louder and I decided to stop before people noticed. We finished our meals and left.

On the ride home, I could tell she was turned on. Her face was sweating and she kept rubbing her crotch. We decided we would be done for the day and I dropped her off at home, before she got out she gave me a quick flirtatious smile, then went on into her house. I went home too, and decided I needed to get off before I burst.

Chapter 4: The Sleepover

It was after 10 at night, I was sitting on the couch watching TV, when I heard a knock at the door. I go over and open the door to find Maddie standing there, she was obviously upset and had tears running down her face. She was wearing black shorts, with the waist rolled up to make them shorter, a black tank top with spaghetti straps that clung tightly to little belly and perky nipples.

"What's wrong," I asked as I ushered her inside and onto the couch.

"I was having a sleepover at my friends house and we got into a fight, so I left, and now I can't go home because my mom will be mad at me, and I just didn't know where to go," she said while trying to fight back tears.

"It's okay dear, you can always come here." I smiled at her while rubbing her smooth back through the thin fabric of her tank top.

"Thank you, you're such a good guy"

"So what did you and your friend fight about, if you don't mind me asking?"

"She said I was a loser because I never even kissed a boy before."

"That wasn't very nice of her, you are not a loser, kissing a boy definitely doesn't make you a winner."

"No she's right, no boy would ever want to kiss me." She started to ball uncontrollably.

"That's not true." She turned and looked me in the eyes. Those beautiful brown eyes were mesmerizing, I continued to rub her back, with my hand working its way up to the back of head. She leaned in and I met her mouth with mine, my tongue met with hers and we hed together. My other hand reached on her back, and slowly worked its way down to the waist of her shorts, I ran my fingertips along the top of the smooth fabric of her shorts, then went lower onto her firm butt, I grabbed it with my full palm. She moaned as we continued to kiss. The feeling of the soft fabric of her shorts and her small butt in my hand and my other hand running through her flowing brunette hair. I then took my hand and ran it up the side of her body, inside her shirt. Feeling her skinny body run through my fingers, I reached the bottom of her breasts and rubbed them gently. She moaned even louder this time, pulling away from our kiss.

We stopped and pulled away from each other, she smiled at me, both of us breathing heavily, but knowing it couldn't go any farther. She whispered "Thank you for making me feel special."

I nodded and smiled, "Well if you want to sleep on the couch tonight, you're welcome to."

"That would be great," she eagerly replied. I went upstairs and grabbed some blankets and pillows for her. When I came back downstairs she was on the couch watching tv. I tossed her the blankets and set the pillows down on the couch.

"I hope you'll be comfortable," I said.

"Sure will be!"

"Just make yourself at home, I'm going to go to bed."

"Stay down and watch some tv with me, pleassse," she said while giving me the puppy dog face.

"Okay, but just for a little while." I sat down while she looked for something to watch. After we settled in, she leaned her head on my shoulder and started to nod off. I put my arm around her and held her tightly. She started to fall asleep and eventually her head was laying on my crotch. This made my dick start to get hard, but she didn't seem to notice. I took my hand and ran it down her back to the inside waistband of her shorts. I could feel her smooth underwear, which made my dick fully erect. I picked her up off of me and placed her back on the couch. I covered her up with the blanket and went off to bed. God was she beautiful laying there sound asleep.

Chapter 5: Good Morning

I woke up at 8:30 to the sound of pots and pans clinking and clanking against each other. I arose out of bed, stretched my back and made my way down the stairs. I walked into the kitchen and found Maddie cooking pancakes on the stove.

"Good morning!" She eagerly said.

"Good morning, looks like you've been busy," I replied, looking around at the two plates and sets of utensils on the table.

"Sit down and I'll get you some food."

I sat down and she proceeded to plop three pancakes on my plate, they were delicious. I sat across from her while we ate, she was still wearing the same clothes as the night before, her hair now was a little messed up from sleeping on the couch, but she was just as beautiful as last night, maybe even more.

"Do you mind if I use your shower?" she asked while we were putting dishes away.

"Of course not, go ahead," I said maybe a little too eagerly, thinking about her small wet naked body in my shower. She gave me a quick smile and then joyfully skipped over to the bathroom. I continued to clean up in the kitchen while I heard the water start running in the shower. I could picture her using my soap and rubbing it up and down her smooth skin, if only I was that bar of soap.

I was sitting at the kitchen table when I heard the water stop, soon after Maddie came around the corner in just a tan colored towel. She stood in front of me, still dripping wet, her smooth white legs glistened in the morning light, with her clothes she took off in her hand. She shot me a flirty smile as she walked over to her bag she had brought with her the night before. She kneeled down and looked through it and found a pair of jeans, a blue t-shirt, a small red bra and some matching red underwear, and she walked past me again towards the bathroom.

While she was in the bathroom, I couldn't help myself. I went over to her bag and took out her freshly worn underwear. I put them up to my nose and the beautiful aroma made my dick get hard immediately. I heard her start to open the bathroom door,so I stuck them back in the bag quickly and walked away.

She walked out of the bathroom in her new clothes, with her hair still wet, when she walked by me I could smell her hair conditioner and it sent the blood immediately to my semi hard erection. I was so worked up, when she walked by me I grabbed her small butt in those faded jeans. I used my whole hand and squeezed her right butt cheek, making her eek out in pleasure and surprise. When I let go she turned around quickly and gave me a devilish smile.