Anna S1 - Fun over the web cam with a stranger.

Anna decide masturbating alone wasn't enough and looked for fun over a random web cam site. The man on the other end gives her s great first experience.

Anna is a cute fourteen year old girl, with a short petite frame, dark red hair and emerald eyes, and by most standards a pretty face. She finally had A cup breasts and couldn't wait for them to be C cups like her mother's. Over the last year her body had gone through changes and with those her interests in sex rose. She became more curious and tried to turn towards porn she discovered her parents put up blockers on their Internet. Those same Internet restrictions didn't extend to her mobile data. She started sneaking onto adult sites at night over mobile being careful to not watch too much and have large data usage on the bill. Something she was questioned about when they first gave her a smart phone.

Tonight was the last day before the new school year, the start of freshman year. She was excited and nervous for what tomorrow would bring. Tonight, Anna was lounging in bed, unable to fall asleep from the anxiety. Nights like this was when she would masturbate, the orgasm often resetting her chaotic thoughts while making her finally feel exhausted. Tapping on her phone she noticed her data use was getting close to the mark when her parents would ask her what she had been up to lately. Letting out a sigh she was back to doom scrolling media staying connected to the wifi. She resorted to her first source of arousal, hot shirtless men online. There were countless videos online she could access with hot muscular men showing off.

Anna climbed out of bed, she was wearing an oversized T-shirt and some sleep shorts. The shorts and white panties underneath were stripped off. She loved letting her smooth pussy out, the two puffy mounds of her labia pressed together. A dark line went from clit to spread into Y at her vagina. It wouldn't be til those puffy lips parted that her pink core and swollen clit could even be seen. From her nightstand she grabbed earbuds before digging into the drawer for a massive marker. It was the only object she had found after googling better ways to masturbate. The information online suggested a dildo but being unable to buy one she looked for alternatives. All sorts of people suggested starting small with a marker or toothbrush handle and working up to bigger things. That was exactly what she had done and was now using this jumbo marker. It had a girth larger than two of her slender fingers and a total length of four inches though only three were ever inserted as she held the cap.

Laying in bed she opened her legs, feet flat on the sheets, knees in the air, back against the head board. Opening an app she got on an account set to follow men making thirst trap content. The feed started with a shirtless man cutting lumber with an axe. The music played in her ears as the rounded end of the marker started to rub into closed lips. Her pussy was like a zipper that never stayed open as the marker ran up and down her slit. The puffy lips parting just to hug closed once more. She watched the video loop for a moment, taking in the way his muscles flexed and then shook as the axe thudded through the log. The marker constantly going up and down and moistening lips.

Swiping to the next video was a man dancing, once more shirtless with tiny shorts letting most of his body be seen. His muscles weren't as defined as the ones but Anna found him attractive. She continued to scroll, the marker proceeded from rubbing against slit to sinking into her wet hole. Tight vaginal canal kept trying to push the gray phallic object out only for it to be pushed back in. Slow methodical movements as she angled the marker to rub against g spot. Browsing videos like this wasn't scratching the itch she had. Her mood was demanding something specific and hot but at the same time wouldn't say what it was. As Anna was swiping through the feed she came upon a guy that would chat with girls over a random webcam site. It was then that her lust finally spoke about what it desired.

Curiosity listened and Anna stopped masturbating to look into a site she could web cam chat with others. While porn sites had been blocked she discovered that places where she could cam chat were not. Without a second thought she followed the bad idea to jump in. The front camera on her phone filled with her face, headboard filling the backdrop. Bare pussy was still uncovered but out of sight with the current view given. Clicking join, the site quickly paired her with someone who saw her and skipped to find someone else. The next person she didn't find attractive and clicked skip. Two more skips and she finally had someone on screen for longer than a few seconds.

“Hi there, what brings a cute girl like you here?” The man on screen had a rich deep voice. Anna tapped on the window expanding his video feed to take up the entire screen. Her own was a tiny square in the top corner that she now ignored. With the image enlarged she was greeted with his shirtless visage. She could see from his belly button and up as his waist was under the edge of the desk she could narrowly see. The backdrop around him appeared to be some kind of home office with a filing cabinet and printer behind him. She couldn't tell how old he was, his short hair had flecks of grey and a well kept beard. It spoke of someone possibly as old as her father, while his defined chest and abs made her think of someone in their twenties. Dark hair on his chest created a line down from pecs to navel.

“Well, Mr handsome I guess I was just looking for something fun before bed. You?” whether it was intended or not her words had a double meaning to him. Looking for fun had been a phrase he used in the past for others to know he was wanting something naughty. Combined with that Anna had no poker face, he knew she was finding him attractive. He assumed she was here for something dirty but wasn't about to scare her off if it was all innocence talking.

“I guess we are looking for the same thing. Do you mind if I ask how old you are?”

“Fourteen, I want to guess you are… 32?” Anna gave a playful smile as she shot out the number. She saw his face light up a little when she mentioned her young age. It didn't set off alarm bells for her as she was horny and had been craving male attention all summer.

“Well, I am more than double your age but I'm actually forty. I hope that is okay.” She had a brief look of surprise at how young he looked for his age. He was in fact around her father's age and for some reason that thought turned her on.

“I don't mind that if you don't. “ Anna had a shy smile, the hand still twirling hair nervously. He bounced a pectoral muscle by flexing, her reaction was instant. A mumbled wow was audible with the way her eyes went wide. Her left hand instinctually went to touch herself as the right kept her face in frame. Puffy lips hugged a finger as it seeked her clit.

“Oh, I don't mind at all.” He gave her another muscle flex dance. This time she let out a pleasure filled groan as watching his body move her finger massaged clit. The endorphins released were too much to contain silently.

“Seems like someone enjoys what they see. Why not let me enjoy seeing more as well. “ The smile he gave made her melt, a nod shaking her head before the words of agreement could be released. Anna pulled her hand away from clit not wanting to let him know she was touching it. She stretched her arm out, camera now showing entire chest and face.

“That is certainly a very cozy look, what's that on the front?” He could only see part of the design printed on the shirt. It was also an excuse to get her to show more. She was happy he took an interest in it and didn't just ask for her to take it off. The man ,before now, asked her to do just that as an opening line, she skipped him for it. That other guy also didn't look nearly as good as the man on screen does now. Anna’s free hand pinched the fabric near her collar bone. Pulling the shirt so it hung flat in the grasp to make the image easier to see. Tilting the camera down she was only looking at him, not paying attention to her own small window feed. The way shit lifted the shirt and tilted the camera to show it off he was blessed with a view of her bare pussy.

“Its got all the characters from an anime I like. The main character is in the middle.” As she held the shirt up for him to view, his gaze was focused down at the juicy lips she had exposed. The grey marker had been abandoned in front of crotch and hinted to him of what she was doing before coming online. Sitting up she saw him leaning in, assuming he wanted a better view of the shirt she smiled. One of his hands went under the desk, the other was leaned on the desktop.

“Oh, it looks cool. Which character is your favorite? “ The question made her think he had some genuine interest but really he used it as an excuse to keep seeing her pussy. The hand under his desk was subtly playing with stiffening cock. Her smooth plump pussy was making his mouth water with thoughts of how good it must taste.

“I like a lot of them but the girl with blue hair is one of my favorites. She is the love interest and uses some cool magic. “ She saw him sit back, no longer leaned in so close to the screen. It had been a minute since the hand was under the desk, she noticed the muscles of that arm flexing. She was curious what was happening as it wasn't just relaxing on his thigh. She finally looked down at her shirt as she was about to mention someone else and noticed her pussy was out. Feeling shocked, her eyes shot back to the screen and noticed they were in view. The hand let go of the shirt and went to hide her slit.

“Oh my god! I'm sorry… I forgot I wasn't wearing anything under this.” She felt embarrassed but saw he was smiling about it.

“Awe it's fine, I was enjoying the view myself. To be honest… I'm sitting here completely naked. My cock got hard after seeing those beautiful lips you have.” No was he afraid she was just an innocent girl. He now assumed she was here to be naughty and he was done beating around the bush. Anna felt flush as he admitted to liking her body and being hard from it. She hadn't gotten male attention like this and it was something she fantasized about all summer. A new wardrobe was purchased for school with dresses and skirts just for that purpose. She avoided tight pants as yoga shorts would always give her terrible camel toe that made her self conscious.

“Do you really like it?” Her thoughts were stuck on his admission. She had desired him to see her pussy but not by accident like that. Since he already saw it and liked it she was feeling more confident about being here.

“Absolutely, I was just fantasizing about how they must taste when licked. you should take that shirt off and join me being naked. If you do that, I'll show what's hiding under this desk.” Anna was this man’s prey and falling quickly into the lustful pit trap he set.

“Would you really like to see my naked body?” The shy expression and action of her fidgeting with hair once more was intoxicating. She was clearly new to all of this and that only made the man all the more interested in her. No one was as fun to teach and groom than as a virgin.

“Oh yeah, for sure! Strip off that shirt and show me what you were doing with that marker you left between your legs. “ Anna was happy to hear those words, a part of her had thought guys wouldn't be interested in her young body. Wordlessly she shifted and set her phone on the night stand. A kickstand on the back of the device allowed him to watch as she pulled the shirt over her head. Like a curtain it rose, allowing pert breasts to greet the audience. The little A cup buds had nickel sized areolas, arousal and cool air hardened their tips. The nipples were like two little gumdrops, standing out from pale flesh with their dark pink hue.

“Isn't that better?” His deep voice muttered directly into her ears, being fully exposed felt both wrong yet right. She had to consciously keep her hands from blocking his view. Legs opening so he could now see fat lips to tits.

“Yeah… Can I see that cock now?” Her voice was soft, feeling shy yet aroused in ways porn never made her feel. He pushed back from the desk and stood up letting his hard cock sway in full view. Pushing the leaver to the deskchair it lifted to its full height. Sitting back down, the massive cock stood straight up, his balls hanging low, resting on the leather seat below naked ass. Near the base she watched his hand wrap around it. He barely reached half way up its length, she realized it was bigger than it appeared.

“It looks so big!” She couldn't help but be surprised, her voice a little louder than expected from the realization. The man just chuckled at the expression her face made.

“It is a little over eight inches long and as thick as a small red bull can. “ Anna had a hard time imagining how something so big would fit or feel inside her virgin hole. The man was slowly rubbing his hand up and down its length, keeping it hard.

“Oh wow, that is way bigger than anything I have ever used. This marker is the biggest I've ever used. I don't have anything in my room that could compare to a cock like that.” She grabbed the marker and held it over her clit, showing just how deep it could go.

“Yeah it is hard to get a good object as an analogy for my cock. Especially if you can't go buy a dildo, I've seen some girls use a cucumber or zucchini before though.” His eyes were fixated on her clit as she started to rub the marker against it. It was rather captivating how her thick lips spit and joined back together as the grey body slid into slit.

“I've never considered something like that before… Do you still like my pussy now that you can see it even better?” she was wishing the marker was his finger. Desperately her body desired the touch of another person. She was still a bit afraid that such a large cock would hurt but she also wanted to try it.

“I love it even more, slap it once for me and let me see how those lips respond. “ Doing as she was told her free hand gave a gentle slap, the sound of fingers clapping into the wet lips aroused him. Fat lips jiggled a moment from impact, their smooth surface glistened from the wet juices in the light.

“Mmm they seem perfect. I bet slapping my cock against those juicy lips would feel good. Let me show you what I use when playing around here?” he started to stand up, hands reaching out and adjusting the camera. Pointing it down his desktop had a sex toy upon it. The waist to top of thigh of a girl made out of silicone. It was a tan color with small open labia, a pink clit, and matching pussy hole. Out of her view was a hole for the ass as well.

“I would replace this with you if I could though. Think you can get your legs open like this?”

“With your help, sure. “ With a little giggle Anna started to move her body to match how the toy spread itself. Knees up high and spread as far apart as she could get them. With thighs open and ready for a man to fill the void her pussy opened. Lips finally separated as she pushed them apart with two fingers. The man on the other side started rubbing his cock on the doll’s clit.

“Now if only you had something to fuck that pussy with that was like my cock. Then as you enjoyed feeling that pussy stretch on a toy I would fuck mine. It would be as close to us fucking as we can get. “ Anna shuddered at that thought while running her middle finger over her pink swollen clit. As he spoke she was trying to think of something she could use. She remembered her mother went shopping for food recently and may have bought some vegetables.

“Well… we may have something I could use. My mom went grocery shopping and often likes to make zucchini and squash. Should I go check?” Anna let out a little moan as it felt good to play with herself. The shyness in her voice from earlier slowly melted away.

“It would be hotter for me if you had something closer to my size to play with.”

“Alright I'll go look then.” Anna hopped out of bed, pert tits jiggled as feet clapped the floor. Picking up the phone she started to head out the room. The guy thought she was just going to go alone quick and come back. Instead she was peeking out her bedroom door, the house was dead silent as it was after midnight. Tip toeing down the hall towards the main part of the house. Coming out the hall to her left was the living room, the kitchen on her right with the dining table on the other side. Between the kitchen and dining area was a door leading to a sunroom and the back yard. Down the other hallway was her parents room at the opposite end of the house, their door was currently shut.

Anna set her phone on the island as she opened the fridge he was able to see her naked ass bathed in its light. As quietly and carefully as she could Anna dug around, finding a zucchini in the vegetable draw. The green food was about to become her new source of pleasure. The rounded end had a nice bulge to it that she guessed was close to the right size. She spun around to show him, holding it up in front of her clit so he could see just how big and deep the object could go.

“What do you think?” Her voice muttered into the mic built into the headphones she wore. He could see the green plant in her small hands, it was certainly good enough. With his own knowledge and experience it looked to be about nine inches long and about as thick as his own cock. The rounded end was the thickest point as it tapered towards the steam but even then it got as narrow as most cocks.

“That will be great. Far better than that tiny marker you were using. It would be so hot to bend you over the counter right now. Do you often walk around the house naked?”

“No, first time.” She kept her answer short and quiet so as to not possibly have her parents notice. She figured they were deep into sleep but the last thing she wanted was for one of them to hear whispers and come out of the closed room. Her room had the bathroom attached so she never had a reason to roam from her room while naked. As she thought about the risk of getting caught here the hotter it was to be naked in the kitchen.

“Wouldn’t it be hot to fuck all over the house? We could go from the counter to the couch and eventually end up in bed. “ Anna found that fantasy incredibly hot, in the glow of the fridge she pointed her ass to the camera. She started to rub the bulbous end of the green phallic object in her wet hole.

“Mmm naughty girl, better pray you don't get caught dirtying dinner with that hot pussy. “ Anna tried to push the zucchini in, its girth was just too much as it started to hurt. Her vaginal entrance barely opened around half its size before she pulled it back and went back to rubbing it on her slit. The hand holding the vegetable was between her legs as the other reached back and pulled cheeks apart. The cold air of the fridge rolling over her body making nipples hard from its bite on naked flesh.

“Slap my cock on those plump lips babe. “ Listening to his demand the green body was held away then came down and bounced off her labia. A wet smack noise seemed to echo through the house but with his voice in her ears she missed it. She smacked her pussy twice more at his suggestion.

“Oh that's so hot. I'm ready to have you watch me fuck this doll as you fuck that zucchini.” Anna had just closed the fridge and was at the end of the island counter when her parents door opened with a pop. In her panic at the noise she dropped to the floor and covered her phone with abs. The sound of a dog’s nails clacked against the floor as the door was fully opened.

“Alright Walter, I'll let you out…” Her father's heavy footsteps made her heart race as the pair passed through the other side of the kitchen and into the sun room. As she heard the back door opening, Anna quietly scrambled into the laundry room. Her bedroom was too far to make it before her father came back into the rest of the house. The laundry room was small, on the left side was shelves with cleaning products, the right side had the washer and dryer. Anna had enough space to hide behind the dryer tucking herself in the corner as the door to the room was left cracked open. She didn't dare risk making it click shut. Taking a headphone out to hear her father better he had walked into the kitchen and was rummaging for a glass. She could see the glow of the kitchen light now on through the small opening.

“Well aint that just hot and poor timing for you. Mmm I would still fuck you as we would try and hide from your parents in the room next door. Just have to stay silent and no one would know.” Anna set the phone on the floor, looking at the man he was rubbing that massive cock on the doll's clit. She couldn't admit that an experience like that was a turn on idea.

“Why not try and get that temporary toy to fit while you're stuck crouched there. Girls have told me it is easier the first time when they squat down on it. “ The man couldn't see how she was biting her lip while thinking it over. The phone's angle and glow only allowed him to see her pussy as she looked down at the device. He urged her one more time before she finally caved. As she held the zucchini under her pussy, legs spread, body crouched against the dryer, it slowly sunk down till she felt it knocking at her entrance. With the earbud off she also heard the water start to pour out the fridge’s dispenser.

“Mmm good girl sit on this thick cock.” The man was now sitting in his chair with the toy in his hands. As she tried to push the zucchini in he would lower the toy down mimicking her movements. She felt a pang of euphoria from how seeing that made her feel. They really were going to act out fucking each other, this wasn't going to just be two people watching the other masturbate. Anna pushed harder, covering her mouth as she felt her tight virgin hole stretch around the moist zucchini. She wanted to moan, cry out, anything to make it feel better as vagina was flaring with pain. The man was uttering encouraging words as he witnessed her tight body finally take the rounded end.

“It may hurt for a moment but I promise, it will get better.” Anna couldn't answer, besides needing to stay silent all her focus was on trying to blot out the pain. She sat there unmoving for a time, her father’s chair groaned as he sat down waiting for the dog to do his business outside. The sounds of him watching videos to pass time broke the silence of the living room. She didn't know how much longer he would be there as she tried to push the zucchini deeper. Vaginal walls were tight, pushing against the large object as her body was rejecting its advance. The stem of the green phallus was on the floor unable to back out as she sat lower.

“That's it, good girl. Sit on this cock…” she was watching him lower the doll upon his erection. It took another minute with her slowly pushing till about eight inches had fit. The tip now pressed into her cervix, as it knocked in deep she almost yelped from the sensation. It didn't hurt but it was like a jolt of electricity shocked her core with intense pleasure. She sat there feeling her body adjust to the object inside it. The pain was slowly melting into pleasure. Her pussy soaking the zucchini in her juices.

“Now try to bounce on it….” His words were more commanding as she gave him more and more control. Wordlessly obeying what he wanted, legs shook as she started to slowly rise. One hand still held the zucchini keeping it planted to the floor as she rose up. A stifled moan rattled teeth as she felt the green beast pushing to leave her body. The pain now gone, only pleasure remained, her pussy hugging it so tight that it squelched a soft wet sound. Her breathing was getting faster as she was slowly lifting up and sinking down on her edible toy. The man copied the motions making it all the better for the two of them. His voice in her ears, closing her eyes it seemed like he was really fucking her.

As she rose up once more, wet hole suckling on its new friend she heard her father getting up. She pulled the zucchini out while intently listening, he went to the door and let Walter back in. The distinct sound of the dog walking on hardwood floors echoing through the house. Walter had gone to his dog bowl to drink as her father went back into bed. Anna poked her head out the laundry room once everything was quiet. Her father left the bedroom door open and Walter went to his dog bed in the living room. With this chance she snuck back into her room, being sure the door didn't click loudly as it shut.

“Shall we continue on the bed?” The man had stopped fucking his doll when he noticed her moving about. Cock left deep in its hole as he awaited her return.

“Yes… just let me get comfortable. “ Placing the phone on her nightstand she got laid down before it. Legs wide she pushed the zucchini in, her pussy was sore from stretching on it earlier but took it without much resistance now.

“i want to fuck you right on this desk like the naughty girl you are. “ She heard the doll’s silicone body heavily slap down on the desk as he dropped it into place. His cock pushing in at the same speed she shoved the zucchini.

“Its your turn to keep up with me…” his words a low growl in her ears made her shudder as he started to slowly thrust. His hips moving gentle at first, the length of his cock disappearing in time with her zucchini. Each time it bumped into her cervix she would moan, a soft release of air mixed with an uh sound. High pitched and full of pure pleasure that only a girl truly enjoying herself could make. His pace increased and now her wet pussy was making noises from the way its walls gripped the thick object. Her lips pursed to keep from moaning loudly that her parents may hear.

“Good girl. Keep taking all this cock. I'm going to fill you with my cum. Leave your pussy stretched and leaking with my seed.” His dirty words spurring her on as the green toy fucked her virgin hole. It took a several minutes to work up to a speed where he was fucking the doll hard. Anna was too tight to keep a similar pace on her end but did her best. The two of them grunting, breathing hard, moaning and watching as they each fucked their respective toys.

Anna had already had multiple orgasms since they started back up in her room. She was surprised he hadn't finished yet as his body kept hammering cock into the doll. His balls slapping, filling her ears with such pleasant sounds. She was nearing her limit though, legs were quivering and pussy gripped the zucchini so hard it was difficult to thrust it. Each stroke was a torrent of pleasure that she both loved and wanted to stop. She never went this far when masturbating, usually one orgasm was enough to satisfy for the night but this was several in a short span. She could feel one last orgasm building, it was going to be a strong one too. Her body already shook from the pleasure she was experiencing, any more intensity and it would certainly break her.

“Almost there, don't stop baby. Keep going, yes… yes! I'm cumming!” The man stopped thrusting as he was cumming. Anna was far behind him, her last orgasm wracked her body. She yanked the zucchini out her used pussy free hand clamping on her mouth to keep the moan in. She went from being leaned back to see the phone as she fucked herself to laid flat. Eyes fluttering as her pussy was gaping open for his viewing pleasure. Her lungs unable to draw in air as her face scrunched, the moan was surprisingly silent till finally her body relaxed. Able to draw in air her lungs filled then released an Oh fucking god.

“Did that feel good?” The man asked as he saw her laying there unmoving.

“Yeah… just… tired now and I don't know if I can move for a little bit. “ Her entire body felt like it was tingling, her pussy now ached. She knew tomorrow would be miserable down there, her tight vagina would be sore from this.

“A big dick and good orgasm can do that for you.” He chuckled while starting to clean up the mess on his own end.

“Get some rest. This was fun. “ He disconnected leaving her there alone till finally the site connected her to someone else automatically.

“Oh fucking hot! Hello there naked princ…” the guy who connected to her was given an eye full. The sudden adrenaline made Anna jump up and disconnect from the site before anyone else saw her. She managed to get up, clean the zucchini and redress before sneaking it back into the fridge. Exhausted and already feeling sore, with the evidence of her deeds covered up she laid in bed. Sleep quickly claimed her as there was no energy left in her body to resist its embrace.

Thanks for reading the reboot of my Anna stories. This all written using my imagination and not based on a true story. If you enjoyed it this leave a comment and a rating!