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Maddy's Chat Buddy

Summary:

Maddy's an 8 year old girl who finds herself chatting with a perverted older man online. What starts out as an innocent enough chat, quickly devolves into Maddy getting in over her head. Some men only want one thing but this one wants every depraved pleasure that he can squeeze out of the young, naive girl.

Notes:

Hey, all! This is my first writing experience on here so we'll see where this goes. There is a bit of a slow build-up to the more hardcore action but there is plenty more to come as I get the time to write. I'm very much so an amateur writer so let me know if it's difficult to read or if I need to revise my past stuff.

Hopefully the chat-log style isn't too strange for you all. I thought that it would be kind of a fun style to employ but it does end somewhere in the 3rd chapter. Sorry if it's an awkward read until then. I want to give a heads up that this story is going to get dark and depraved. This is purely for fantasy purposes and I don't endorse this behavior in real life.

(I want to give a quick thanks to all of you who have read my content. And especially those who have given kudos and left messages. I appreciate all of you and hope you found the content to be interesting. Your reactions have fueled me to keep the story going.)

Chapter Text

Madison laid comfortably along the sheets of her bed on that warm summer night. The eight year old girl scrolling on her phone before bedtime. The house around her was fully silent since the rest of her family were already asleep. Only the chorus of crickets chirping outside her opened window would add any kind of background noise to the scene. The fresh nighttime air would waft through the window filling the room with the scent of fresh cut grass and a hint of her mother’s flower garden out back.

She wore a simple t-shirt that was a bit baggier. It was her favorite shirt to wear to sleep because it was so airy underneath. Below that, she wore a clean pair of her short running shorts. Her bare feet are all tangled up in her quilt towards the bottom of her bed.

With no other action happening in the house, Madison had resorted to opening the ChatBack app, hoping that any of her friends might be online to chat. But every one of her friends seemed to be offline as the small list of contacts in the chat window were all grayed out. Usually her best friend Tori would be online during this time of night but she must have been busy with something else.

Madison was tired of watching videos online and was really hoping for some personal interaction. Even at her young age, it was quite apparent that she was a social butterfly. The young girl typically taking an interest in sports and school events but since summer had come around, none of that was going on. While her parents would allow her to stay the night with friends every now and then, she wasn’t getting the level of social interaction that she typically craved.

Minutes went by and she stared at the app’s home screen hoping for someone to get on and cure her boredom but nothing changed. The longer that she laid there, wriggling on top of her sheets in boredom, the more her thumb began to hang over the ‘Random Stranger’ chat button. She had never used the feature before. In fact, her parents made it clear that she wasn’t to talk to strangers on the app when she asked to download it. Her mom lifted the child safety settings on her phone to enable the app with this promise in place because she was so persistent on wanting to use it to chat with her school friends.

The feature would match her up with another local user to ‘make friends’ with over the chat app. She bit her lip, wondering if she should open that door. Her parents would likely never find out and she was bored out of her mind. It could be fun to chat with a random person for a short time before she finally turned the lights off for the night. Seriously though…. her parents would never know.

In a rush of defiance brought on by crippling boredom, she finally tapped down with her thumb and allowed the app to match her with someone to talk with for the night. A loading icon blinked along the screen for a few seconds before the new chat window popped up on the phone.

*Stranger: Hello! :) How are you tonight?
*Maddy: Good. U?
*Stranger: I’m good. Is that you in your profile pic?

The profile picture was of her from earlier that summer. Her mom had taken it of her while they were on the beach at her uncle’s cabin. The cute brunette girl with her sparkling brown eyes and lightly bronzed, sun kissed skin. Her face having the faint showing of freckles that always appeared in the summer months when the sun seemed to bring them out. She had a cute little, soft blue bikini that was framed out by a pink hemmed outline. Her childish body held barely any curves in the bathing suit. But for her age she was already showing signs of being a girl blessed by natural beauty. Even if a bit stringy in nature with her long legs and torso.

*Maddy: Ya. That’s me in the pic.
*Stranger: Nice!
*Stranger: How old are you?
*Maddy: I just turned 8 last month
*Stranger: Nice!
*Maddy: U?

His profile picture was just the default that showed when you first created an account on the app….. a silhouette of a person with a gray background. There was really nothing to give any information on who she was talking to.

*Stranger: I’m 49
*Maddy: Oh
*Stranger: Is that okay?

This app was more geared for the younger generation and Maddy had never really expected an adult to be on it. She could never see her own dad or mom downloading the app. She just figured that she was talking to another kid.

*Maddy: Ya
*Maddy: Ur like
*Maddy: Twice the age of my dad lol

This was a bit of an exaggeration. Her dad had gotten her mom pregnant right out of highschool. But she wasn’t too far off from the truth.

*Stranger: Oh sorry lol
*Maddy: No worries!
*Stranger: You’re really pretty for your age!
*Maddy: thx
*Stranger: What are you up to tonight?
*Maddy: Bored
*Stranger: Well hopefully I can change that! >:P
*Stranger: Do you usually talk to older men on here?
*Maddy: No
*Maddy: My mom would kill me if she knew I was talking to u lol
*Stranger: lol
*Stranger: Parents can be silly!
*Maddy: Ya lol
*Stranger: Where are your parents now?
*Maddy: bed
*Stranger: Are you alone?
*Maddy: Ya
*Stranger: Nice!
*Stranger: What do you like doing?
*Maddy: Soccer. Doing walks and runs with friends.
*Maddy: Mostly just hanging out.
*Stranger: Cool
*Stranger: You look like you keep nice and fit
*Stranger: Like in your profile pic
*Stranger: You look sexy in that bikini

Maddy had never been called sexy before. She wasn’t even entirely sure of what the word meant. She knew that it was more like an adult term for beautiful. The compliment felt a bit polarizing to her at first but it did send a quick strange tingle between her legs at being described as that adult word.

*Maddy: thx
*Stranger: Sorry lol
*Stranger: I hope that’s okay to say?
*Stranger: That I think you’re sexy…
*Maddy: Sure lol
*Stranger: So your parents are asleep?
*Maddy: Ya
*Stranger: Do you ever like to do naughty things when they aren’t looking?

The 8 year old girl rolled against the sheets in bed as she flipped herself around. What was he asking? Sometimes she might sneak a cookie out of her dad’s snack drawer or something but she wondered why the stranger would care about any of that.

*Maddy: idk lol
*Stranger: Hmm lol
*Stranger: You look like you’d be naughty
*Maddy: Wut?
*Stranger: Never mind lol
*Stranger: Do you like boys?
*Maddy: I guess
*Stranger: Do you have a boyfriend?
*Maddy: No
*Maddy: My friend Tori does
*Maddy: Mom says I’m too young for that
*Stranger: Have you ever seen a penis?
*Maddy: No lol
*Stranger: Can I send you a picture of mine?
*Maddy: Wut?
*Stranger: I want to show you my penis
*Maddy: idk
*Maddy: I guess

She had never really seen a penis before. There was a slight curiosity. She knew that boys had different parts in their pants but she hadn’t quite had the full sex talk with her parents yet. There was a bit of anxiety running through her, knowing that her parents wouldn’t approve of this chat. It was just stacking on top of the previous disregard for their rules. It took a moment but the picture loaded into the chat. There on her screen was the image of a long, erect penis jutting out from a dense bush of pubic hair.

It was a bit of a shock to see. She didn’t think that penises got that big. How did they fit in boys pants? The erection was thick and veiny and topped with an umbrella like tip that flared out with a purplish hue. Curly dark hairs spanning the lower half of the shaft as the skin glistened of light perspiration in the amateur shot of the male sex. It was kind of gross to her at first glance as her face scrunched up at the sight but she felt another quick tingle between her legs as she looked at the pornographic image.

*Stranger: Do you like it?
*Maddy: idk
*Stranger: Would you want to suck on it?
*Maddy: Wut?
*Maddy: Gross lol
*Stranger: No. You’d like it! It’s fun.
*Maddy: rly?
*Stranger: Definitely
*Maddy: Is it suppose to be that big?
*Stranger: It’s not always that big lol
*Stranger: It gets bigger when I see a sexy girl
*Stranger: Your profile pic made mine get big lol
*Maddy: Oh ok
*Stranger: Can you send me a pic?
*Maddy: Of me?
*Stranger: Yes
*Stranger: Can you take off your shirt and send me a pic of you topless?
*Maddy: y?
*Stranger: Because I think you’re sexy
*Stranger: I want to see a picture of your boobs lol
*Maddy: I don’t have any boobs yet lol
*Stranger: That’s okay!
*Stranger: I still want to see
*Stranger: pls?

Maddy’s parents had been very adamant even from a young age that no strangers should ever touch certain parts of her body. They had pulled her aside a few times to have the talk about how strangers should never touch her private areas including her chest. She had to assume that showing these things was also frowned upon by the house rules. It felt very naughty sharing a picture of what was normally under her clothing.

But the thought of sharing her first nude also sent an even stronger ripple of satisfying tingling through her young vagina. And it didn’t seem as bad as doing something like this in real life. This guy couldn’t do anything from over chat. And it was just a picture. As awkward as this conversation was getting…. there was a part of her that found it magnetizing.

*Maddy: Just a pic of my chest?
*Stranger: Yes
*Stranger: And face too pls

Her young mind battled with itself for a moment. She didn’t want to slide too far past her parent’s boundaries but she was also intrigued by where this was going. She had never done anything like this before. Her young pussy was tingling the more she thought about it. Finally, her fingers curled to the bottom hemming of her bedtime shirt and she peeled the top up to her armpits. Just high enough so that her pink girlish nipples would show from under the rolled up shirt.

Switching her phone to the camera mode, she aimed it so that her slender childish torso, flat chest dotted with two perfect little nipples and her smiling face were in the shot. Her upper body was sun kissed from earlier that summer other than the perfectly pale areas around her nipples where her bikini top had protected and the lines of it’s straps. Snapping a picture of her practically topless with her pink bed sheets acting as a backdrop behind her. She hit send and the nude photo popped up into chat.

*Maddy: Like that?
*Stranger: Yes
*Stranger: Fuck!
*Stranger: You look so pretty with your shirt pulled up like that!
*Maddy: thx
*Stranger: I love your tits
*Stranger: I wish that I could touch them
*Maddy: lol
*Maddy: like I said
*Maddy: no boobs
*Maddy: mom says I’ll get them soon tho
*Stranger: No worries
*Stranger: I think that you’re sexier than most girls are who have boobs
*Maddy: rly?
*Stranger: Definitely!
*Stranger: I’m jerking off to your pic
*Stranger: I wish that I could finish on your chest
*Maddy: Wut?
*Stranger: Can you send me another pic?
*Maddy: idk
*Stranger: Can you take a picture of your butt hole and send it to me?
*Maddy: Wut?
*Maddy: My butt hole?

The young girl’s eyebrows furrowed at the request. Who would want a picture of another person’s butt hole? That just seemed strange. Was he joking or pranking her? Sending a pic of her bare chest seemed innocent enough but this request was a bit too odd for her comfort.

*Stranger: If you want
*Stranger: I’d like to see how tight it is
*Maddy: idk
*Maddy: I might need to go to bed for the night
*Stranger: Aww
*Maddy: sry
*Stranger: Before you go. Can you accept my friend request?
*Stranger: I want to talk to you more sometime

A notification popped up on her screen for the new friend request. Madison eyed it up, unsure of how to respond. Her mom wouldn’t approve of her making friends with a stranger but it was kind of fun chatting with him…. even if it was a bit weird or different. Her thumb tapped the ‘Accept’ button before she thought too long on it though.

*Stranger: Thank you!
*Stranger: Have a nice night, Maddy!
*Maddy: U 2

With that, Maddy tapped to log out of the app and then placed the phone off to the side, along her pillow. Before she could work at getting too comfy for the night, she noticed something that she hadn’t noticed during the chat. There was a sticky wetness in her panties. There’s no way that she peed herself? Reaching down and pulling at the elastic waistband of her gym shorts. Her thumb opened her shorts and panties up so that she could see the clear sticky fluids stringing between her sweet bald cunny and the materials inside.

Her cute little hand reaching underneath to touch the newly found fluids. Pulling out, the stringing cunt juices webbed between her fingers. It didn’t look like pee. It was just wet and slimy. There wasn’t time for a shower tonight but feeling self conscious, she slipped out of her soiled panties and tucked them into a drawer so that her parents wouldn’t find them. Pulling out a fresh pair and pulling them up into place before settling back into bed. That was odd.

Rolling over to one side, she closed her eyes and began to attempt to retreat to her dreams. The process was interrupted by a notification being sent to her phone. She reached for the phone and clicked on the notification. Her chat with the stranger opened back up to a new photo that he shared in their chat. It was another picture of his penis but this time there was a thick creamy substance drooling down his shaft and matting his pubes. His large hand being held out for the photo to see that the same creamy, pearly substance is filling his palm.

*Stranger: Your nude pic made me make a big mess lol
*Stranger: Thanks again!
*Maddy: My pic?
*Stranger: Yup
*Maddy: Wut is that?
*Maddy: The white stuff…
*Stranger: Cum
*Stranger: We can talk about it later
*Stranger: Have a good night!
**Stranger Left Chat**

The stranger’s icon went gray, signaling that he had logged out for the night. Madison didn’t understand how her picture could make that big of a mess. She sat staring at the lewd image of the man’s orgasmic results trying to figure out what he meant. There was clearly a lot that she didn’t know about yet and the man kept her curiosity running. Even as she closed the chat again and put her phone away for a second time, she laid there in bed trying to figure out what that last string of messages meant. Her wonderment still trailed off into shut eye and dreams soon enough though.