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Wandering Eyes (m/ff, m/f, 1st, pett, mast, sex)

Ace MD · 3299

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Offline Ace MD

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on: January 28, 2020, 02:36:10 AM
This is a work of fiction. The author does not condone any sexual activity among persons under 18 in real life.

 Jake could not believe the situation he was in, never in a million years could he have imagined this. It was like a wet dream, only better, because it was very very real. Jake was standing, somewhat nervously, in the corner of a dark room. The shades were pulled over the window. The door was closed behind him. Two of the prettiest girls he had ever seen were sitting at chairs by a computer screen, a little blue light indicated the webcam was on, and the screens pale glow was the only other source of light for the room. On the screen was what looked like a power point slide with a score on it. And both girls were taking off their pants.

In the dull light of the computer screen, and the specks of slotted light coming from the covered window, Jake watched with rising anticipation. Indeed his penis was rising as well, and his mouth was dry just thinking about being in the room with two girls undressing. Ostensibly the girls had tasked him with watching the door, but Michelle’s parents weren’t home and her little sister had after school care. They sat in their chairs in front of corner that Jake had backed himself into.
Michelle was one of the most popular girls in Stony Creek Middle School, she had pale white skin, dirty blonde shoulder length hair that was dyed light blue and pink at the tips. She had beautiful brown eyes that always had makeup around them, thick eyebrows but thin pink lips. Her body was slender and long. Then there was Lydia. Lydia had dark exotic skin, her eyes slanted just slightly, darker brown hair and eyes, and a more boyish body except for her butt which was rounder than Michelle’s. Her face was plainer than Michelle’s, and unlike Michelle her parents didn’t let her wear makeup.

Both girls, giddily but nervously, pulled down their pants. Lydia slid off her jeans and Michelle dropped her jeggings. They turned around so their panty clad butts faced the computer screen, and shook them at the web camera. But now their faces faced toward Jake. He tried not to stare, he really did, but his eyes caught the girls’. Lydia embarrassingly turned her eyes low so she didn’t have to look at Jake. But Michelle, always confident, noticed him staring and just smiled back.

Moments later the girls were following new instructions, take off their shirts. Jake didn’t think his penis could get any harder and he was sure the girls would notice it even with their backs turned to him, even with the low light of the room. Michelle went first pulling her shirt from the bottom and tossing it off, she wore a thin bra she probably didn’t need. Watching from behind Jake could appreciate the thin straps covering parts of Michelle's milky white, smooth, and skinny back. Then came Lydia who was slower getting her shirt off and even turned her head before she did it to see if Jake was watching.

“Isn’t he supposed to watch the door, not us?” Lydia remarked to Michelle. “Oh no one’s home anyway don’t worry about it” Michelle responded.

So Lydia, begrudgingly removed her shirt too. She had no bra, and almost no breasts to speak of. Michelle turned her head half way to Jake and motioned for him to get a better view. Shyly, Jake hugged the edges of the room until he was parallel to the two girls. They were flashing the screen and Jake stared at the first bare girl chest he had ever seen, correction, the first two!

Jake breathed nervously, his heart pounding, as Lydia and Michelle were once again shaking their backsides but this time they had their hands edging their panties down. Michelle counted to three and the two pulled down their panties. Lydia immediately pulled them back up as if only to flash the webcam but Michelle kept hers down and shook her butt. Jake stated in awe her bottom was an amazing and only came to his senses when he saw Lydia finally pull hers down for good too. One firm milky white bottom next to a darker rounder ass. And what was that, Jake thought, he could see something between Lydia’s thighs just below her butt. It looked like a dark bulge of skin with a line down the middle...was that her pussy?

Jake could only describe the swelling in his pants as borderline painful now. He squirmed and tried to nonchalantly cover himself. But he wanted a better view. Jake inched closer to the girls.

It was like Michelle could read his mind, she had turned around closing her legs together and pointed to something on the screen She giggled and whispered to Lydia and in a moment she was sitting on one of the chairs facing the computer and spreading her legs to flash the camera. Lydia had pulled her panties on and in shock covered her mouth while pointing at Michelle. Michelle had closed her legs almost as quickly but was now telling Lydia to flash the computer too.

Michelle spread her legs again and this time left them open. She placed her fingers just above her vagina mound. Jake was staring in awe, Michelle’s pussy was in plain view, two fat outer lips completely bald, smooth, and the same pristine white of her skin. The outer lips ended in thin lines that moved entrancingly as Michelle amateurly rubbed her fingers above her pussy, occasionally the movement opened them just enough for a glimmer of bright pink to reach Jake’s view.

Michelle finally squeezed her legs shut and started pushing Lydia to spread hers. Lydia bowed to the peer pressure and shot open her legs intending to only quickly flash the screen but as she tried to close them Michelle playfully held them open for the camera. Lydia brought her knees together but then laughed and kept them spread.

Now both girls were sitting on the chairs, topless, their tight little stomachs and mostly flat chests sticking out to extenuate their almost non existent breasts. Both girls had spread their legs wide, touching knees where their two legs were spread in the same direction. Their hairless pussies on brazen display. Jake was mesmerized that one pussy could look so different from another. Lydia's was hairless and smooth too, but he couldn’t see nearly as much, it was like two thick columns of flesh met together at a line...


Jake had been so entranced that it was a shock when he heard Michelle say his name. His heart jumped, as did his cock, and his face turned to meet Michelle’s.

“You have to touch Lydia, it gets us more points.” Michelle repeated.

“What, wait ... why does it have to be me” Lydia complained.

“Because you’ve known him longer, it’d be weird if he did it to me, but you guys are friends, come on Lydia ...”

Jake listened to the two girls talking like he wasn’t there, but he wasn’t complaining. When it was settled he found himself between Lydia’s legs on his knees. She was pushing her hips toward him, toward the camera.

“Move Jake or he can’t see ...” Lydia complained.

Even in this moment, thought Jake, she was still annoyed at him. Jake scooted to the side. He was still going to get to touch her. Jake moved his hand toward Lydia’s pussy and took a deep breath, he slide his fingers up against the two protruding lips trying to find, well he didn’t know what he was trying to find. But he clumsily moved his fingers up and down the two tightly closed lips. Jake couldn’t believe he was touching Lydia, that his fingers were rubbing her vagina. Instantly his head was swimming, he even felt dizzy. It was one of the softest things he had ever felt. And then it was over.

“Ok we got the points, enough.” Lydia pulled back and raised her panties back up.

Jake stood back up and forgot to cover his pants. The bulge near his jeans zipper was unmistakable as it pointed in the direction of his two friends. Lydia pushed Jake back lightly with her hand to move him away from the web camera. Jake’s head was hot and his ears felt clouded, so he missed whatever the girls had said that got both of them laughing. Soon they were pulling their shirts on over their heads, oddly shyer about their tits then their pussies. Then came their pants, but the girls flashed their round bottoms at the camera as they pulled them up.

Then the computer screen changed and new text could now be seen. Michelle opened her eyes and mouth wide, and looked back at Jake.

“Jake you should take out your ... penis” she said.

“Wha... what?”

“It says we get even more points if you take it out and show it.”

Michelle pointed to the screen as even more text came up.

“Oh ... my ... god, you have to do it Lydia.” Michelle said.

“Do what?” Once again Jake felt like an accessory.

“She needs to put it in her mouth.”

It took a bit of convincing, both for Lydia and Jake to agree, but Michelle was stubborn and use to getting her way. Jake was fumbling with his zipper and as soon as it was down his penis stuck straight out. He was embarrassed, he didn’t know if it was big enough, he didn’t know how he measured up to other boys. Not that it mattered, neither did Michelle or Lydia. But four and a half skinny inches stuck out, the few sparse hairs he had just at the base still hidden by his jeans and boxers. Michelle and Jake were both watching intensely as Lydia was inching closer to his penis.

She opened her mouth and engulfed him ... only for an instant, but he felt wet warmth surround his cock. Lydia had not known what she was doing but had taken in his penis in one motion and closed her lips. She had started pulling back from his penis almost as soon as she closed her lips but it had been too late... Jake felt his penis spasming up and down in her mouth, embarrassed he hoped she hadn’t felt it. Jake couldn’t quite call it a full orgasm but he knew he had cum, luckily nothing had ever come out when he masturbated so he prayed Lydia might not have noticed. Jake felt his knees go weak and almost fell over as Lydia pulled her head away with a disgusted look on her face. Michelle helped steady him and laughed before she went back to the pale glow of the computer screen.

Jake, now sitting weakly in one of the computer chairs, was in amazement on how this had happened, after all it had been yesterday when Michelle had approached him...


No question that most of the 8th grade boys loved Michelle, but Jake loved, like ... was in love with ... Lydia. She was his literal girl next door. He had realized it as they were graduating Little Creek elementary that he was head over heels about Lydia. They had been best friends all fifth grade year long, neither having any other really great friends. And it was at the graduating dance that he realized he wanted to dance with Lydia. He had spent the summer pining over her, even as she was away at sleep over camp the entire time.

He had made due all summer with that one memory he so frequently masturbated to. The time he and Lydia had pulled out the sex ed booklets they had been given in class and read them together at her house. Looking at the crudely drawn genitals and descriptions of sex had been the most erotic thing he had done in his short life. Especially as they talked about all the different variations, like the mind blowing concept of oral sex.

But when middle school started, things changed. Their school was one of several that joined to become Stony Creek middle. With all the new kids and going from oldest to youngest, everything was different. Old cliques broke up and new ones expanded. Kids found new friends. And the formerly most popular girl Michelle became one of several popular girls.

Suddenly, shy Lydia and loud Michelle were hanging out together. They were almost opposites, Michelle’s parents let her do whatever, she always had color; in the makeup on her face, in the nail polish on her fingers, even in the tips of her dirty blonde hair. Lydia had strict parents, was better at school, and was much plainer and quieter. Jake loved her just that way. But Lydia was also pretty and by becoming Michelle’s best friend she got much more attention from other boys too.

Jake found out quickly that when Lydia had Michelle in her class she wasn’t sitting next to or talking to him. Eventually Jake got a handle on his new school. He joined basketball in the winter and made his own new friends, all guys of course. And he just came to accept the growing divide between him and Lydia.

At some point, during some math class, Jake was grouped with Lydia and Michelle. It took a little time but the awkwardness of Jake’s and Lydia’s faded friendship was overcome by Michelle's gregariousness. To Jake, it always seemed Michelle facilitated the conversation, as if she was some mediator between him and Lydia. This only served to confuse Jake as to how Lydia was feeling. But the three of them chatted and gossiped, and while Jake always felt a little like the third wheel, it was generally exciting and fun when they had to partner up.

After spring break and the end of their projects, Jake was sure he wouldn’t be speaking to Michelle and Lydia anymore. So it was surprising when Michelle came up to his table during lunch.


“Oh hey Michelle” Jake replied as instantly all of the boys around him stopped talking to observe this rare sight of girl and boy interaction.

“Lydia and I need your help after school tomorrow with something, do you think you could come over?”

“Uhh..” Jake probably needed to check with his Mom, but he couldn’t dare say that. “Yea yea that’s ok.”

“Ok, great.” Michelle smiled, the kind of smile that made most of the boys at school weak to their knees, but Jake's eyes darted to the table she came from where Lydia only peeked her eyes up looking horrified.

As Michelle walked away, probably not even out of earshot, a flood of jabs, pokes, jokes, and chatter erupted among his table. “Oooohhh”. “Michelle likes you.” “Yea boy.” “So lame man, what are you a pussy?” “Jake's not gonna do anything.” “I wouldn’t with her, I heard shes been around the block.” Jake's head, not for the last time this week, was swimming.

Later, Jake worked up the courage to talk to Lydia.
“Hey.” Jake said, approaching Lydia as she was closing her locker. She was hugging her book bag to her chest, wearing tight jeans with a blue textured shirt that fit snugly over her flat chest. She looked so cute to Jake.

Her eyes flashed toward him before turning away while she replied.

“Oh ... hi.”

“What is it that you and Michelle need tomorrow?”

“I can’t believe she asked you, ugh, we don’t really need anything. She just wants to show you this dumb game, I don’t know why.”

“I mean that’s cool, what game?”

“I can’t really explain it. Look you don’t have to come.”

“Of course he does,” came a voice from nowhere. Michelle had showed up, always the center of attention she had a huge toothy grin that only another middle-schooler could love, but boy did they. Jake couldn’t help but notice the lumps showing in her shirt. “... we need a watch out Lydia, come on. Jake your coming right?”


“Ok you two walk to my house.”

“Wait why do we have to walk alone,” Lydia questioned.

“Because my mom is picking me up and I can’t bring anyone home, duh.”

Lydia looked confused.

“I always come over?”

“Yea but not a boy like Jake, and we can’t make Jake walk alone, don’t be a bitch Lydia” Michelle teased.


The walk to Michelle’s with Lydia had been kinda fun. It had reminded Jake of the old times they used to hang out in play grounds and walk around the block in elementary school. But the walk back to their street from Michelle’s, now that was a very, very, different story.

Awkward was a massive understatement. The two walked in dead silence almost all the way to their street. Jake wanted to say something so badly, but he had no idea what to say. He spent the entire walk thinking of the right words, but they would just get stuck somewhere between his belly and his mouth, flooding his body alternatively with warmth and cold nervousness that felt like when he had to take a foul shot during a basketball game.

What do you say to the girl of your dreams? The one whose pussy you finally saw ... and touched!! What do you say to your first girl friend, you know girl who is a friend, not ... “girl friend,” after she had had your penis in her mouth? What could he say? So as they approached the house at the end of the street that bisected their block, knowing full well that Jake had to turn left and Lydia right, Jake only managed to stumble out “that ... that was nice, we should hang out again...” before sprint-walking away completely mortified.
As much as he wanted to wish it away, the awkwardness did not go away the next day at school. During math class, Jake even tried to lean in his chair as far as possible away from Lydia, and they were already sitting several rows from each other. But Michelle, who in her super-social powered form, did not allow little things like paralyzing embarrassment from achieving her goals, came right up to Jake after math class. Usually, Lydia would follow, but she stayed behind at her desk.

“Oh my god... yesterday” Michelle spoke, first excited and loud before dropping to a whisper, “was so much fun, we have to do it again.”

Embarrassment is strong to a middle-schooler, yes, but these words with all their implications touched the strongest part of a developing adolescents brain and Jake could literally feel his penis hardening and struggling to straighten in his confining jeans.

“Uhh, yea sure.”

“That guy probably had no idea how far we’d go, it was soo funny.”

Michelle had a way of putting people at ease with her friendliness, and Jake succumbed to her bubbly and infectious personality.

“Yea we totally called him on it.”

Lydia, unable to pretend to be collecting her things at her desk any longer finally walked over to Jake and Michelle.

“Come on Michelle lets go.”

“We gotta do it again Lydia right?”


“I mean there’s more points we can score, everyone’s game is different, I think we can have even more fun.”

“If Jake's not invited.”

It was like a brick wall had slammed into Jake, he had taken so much of Lydia’s behavior as just because of changing cliques in middle school. Or maybe, he had secretly hoped, because she had a crush on him too. But he just didn’t understand why she was always negging him, especially after she said that.

Lydia walked away but Michelle, looking concerned only for the briefest instance turned back to Jake.

“We’ll work on her, don’t worry.”

As Michelle left, for once running after Lydia, Jake could only once again admire the differences between the two. Lydia, had always been colder, quieter but was his bestest friend. Michelle had never given him the time of day in elementary school, but she was louder, warmer, and full of energy.

Lydia still wearing a plain collard shirt and jeans, but with an ass that shouldn’t be possible on an otherwise still developing teen, walked away. Jake could only think she was perfect, he didn’t need all of Michelle’s flair. But that didn’t mean he couldn’t admire it. Michelle bounded after Lydia, having already made the switch from cool weather jeans to even tighter warm weather khakis colored shorts that cut off just below her non-existent butt. Showing her impossibly long legs with her knobby knees, and terminating in a beautiful V between her milky white thighs. As she walked away he could see the color streaks in her hair tips, the bright and low cut brand name shirt she wore, and could still remember the color she painted around her eyes.

It was after school that Michelle finally caught up with Jake again. Her vibrant eyes flashing at him, the sparkly bright green eye make up, looking freshly applied, catching Jake’s attention immediately. Although, as always it was a hard choice between that unmatchable cute and attention grabbing face or  the bumps that protruded from her shirt. Jake was going to keep it cool, he thought.

“I don’t know what her problem is,” Michelle said, referring to Lydia. “I had fun.”

“Me to.”

“Maybe she like, I dunno, senses something.”


“Like because you guys were friends for so long.”

“She told you that?”


“Yea I don’t know why we aren’t anymore.”

“I can help you.”

“Help me....?”

“Become friends again.”

“Yea that would be great,” Jake exclaimed, realizing he had been a bit too excited. And he knew he was caught, Michelle had a coy smile and was eyeing him.

“So do you like her?”

“What, umm, no...”

“I need the whole story Jake, if you want me to help.”

Jake was defeated, his shoulders slumped.

“Ok tell you what, come over tomorrow and we can talk about it.”


“Oh wait its Friday, can’t do that. But how about Saturday afternoon, my parents will be out and my sister is at her friends.”

“Uhhh ... ok sure.”

And so it was set. What had he gotten himself into, Jake thought. If he only knew...

If you knew Michelle, you knew she expected to get what she wanted. You knew she was probably a vixen in the making. You knew she was a social butterfly but had a softer quieter side that no one got to see, a place where her inexperience and uncertainty could roam free when she would never allow it to be seen by anyone. Somewhere between these disparate personality traits she made plans, plans she expected would go off without a hitch. And why not? She was Michelle of course, this is what she did.

So on a very sunny and lazy Saturday, Jake made ... some excuse ... and got on his bicycle to go over to Michelle’s house. He was greeted by a Michelle still in sweat pants, cute and adorable sweat pants, but sweat pants none the less. Wearing a spaghetti strap top and sans make up. He had never seen Michelle like this before.

“Come in, quickly, before the neighbors see” she spoke pressingly. Jake was urged into the house and directed to remove his shoes. He glanced backward to see Michelle close the door and his bicycle disappearing behind it.

Shortly they were sitting on her living room couch enjoying her house’s air conditioning. Michelle got up to offer Jake a drink, selecting for him a gatorade while grabbing a soda for herself.

“So, tell me the whole story.”

Jake exhaled and felt a shaky cold nervous weight lift off his shoulders. As soon as he began talking he opened a floodgate of words expressing feelings that only an emerging teenager could have. Michelle listened actively, occasionally finishing his sentences or prying for more information. Jake told her about their friendship and his crush on Lydia. He got an excited breath from Michelle when he finally relented and told the sex ed story. And received an “Awwww” when he relayed how he first realized he liked her at the school dance.

Silence was what waited for him at the end of his tale. But only for a moment as Michelle beckoned him up stairs to her room before going into her plan. She always had a plan after all.

“Ok, you two are obviously perfect together and we are gonna make this happen.”


“Oh yea. So I’m gonna talk to her about it...”

“What? No you cant do that.”

“Relax I won’t tell her your inner secrets, I can play it cool, trust me.”

What choice did he have really, thought Jake.

“But you have to listen to me and do exactly what I say.” Michelle added.

“Ok,I guess.”

“Great and first we have to make her jealous.”

“How are we gonna do that?”

“We’re gonna start by hanging out a lot more and making her feel left out of the fun. We can even stay today by playing the game again.”

“Wait ... how’s that going to work?”

“Just trust me.” Replied Michelle. And while Jake didn’t quite get the logic behind it, who argues with Michelle?

Back in Michelle’s family computer room Jake sat, in place of Lydia, in a computer chair beside Michelle who was operating the mouse. She clicked into a video chat room and Jake and her kept skipping all the different people they were matched up with. They were looking for someone playing the game. So they passed little kids, weird looking adults, several screens with just a penis filling the camera, until they finally saw the blocky lettered, solid background, colorful screen of someone hosting the game.

It started innocent enough, the screen suggesting for flashing their stomachs, kissing, or at worst, mooning to earn points. But Michelle didn’t want to wait to pass all the “boring” stuff and she made sure to type that in the chat window. Jake thought they could probably just say it, since the video chat included sound, but somehow typing it seemed to put an imaginary shield in front of them and let them go way further than if they said it aloud.

So it was soon enough that the suggestions told Michelle to flash the web cam. Michelle pulled her shirt up, revealing that today she was not wearing her little bra. It was hard to even describe her breasts as cones, but subtly they rose from her chest in the same milky white color of her skin, until culminating in the softest shade of pink at the nipple. From straight on Jake could barely notice them rising off her chest, but if he looked from the side or above or below the definition was there. Jake's hungry eyes, with his open mouth, and head moving to get a better view was not lost on Michelle who just smirked at him.

“You too.” Michelle said and pointed at the screen.

Jake took a deep breath to calm his nerves and pulled off his shirt. He had the smooth muscular definition only someone developing from childish lines to young teen tightness could have. He was blessed with an unearned six pack on his stomach. Jake didn’t have breasts to rest his shirt on once he lifted it up, so he finished the job and pulled it all the way off. Michelle was pulling her’s back down, and Jake found himself missing her flat smooth stomach as much as those incredible supple boobs.

Michelle and Jake read the next option for points, and Michelle turned to Jake.

“I’ll go first.” Jake was till trying to figure out if her going first meant he touched her or she touched him when she made it very clear. Jake was wearing sports shorts so with little effort she slid her hand down under the hem of his boxers, and fished out his rock hard boy dick. His shaft was smooth, but hot under her fingers. The head of penis was darker colored and was completely engorged. Jake leaned back as Michelle clumsily jerked his dick up and down. Not that her technique mattered, Jake simply couldn’t believe how fast they had gotten here.

“Now you.” Michelle said.

Jake gulped and read the screen again to make sure he understood. He too easily slid his fingers under her sweat pants but he missed getting under her panties. He slid his fingers back and forth a couple times around the silkiness of her underwear before she removed her hand from his cock to assist him getting his fingers under her panties and in the right place. Not that the person on the other side of the webcam would have known whether Jake was doing it for real or not. Jake’s fingers slipped past soft and occasionally wet skin as he maneuvered his fingers up and down, turning his eyes back and forth between the slender hand, with neon pink nails holding his hardness and his own fingers moving inside Michelle’s pants with only his knuckles sticking out of her waste band. Jake tried to picture in his mind what Michelle's pussy looked like and to figure out what part he was touching.

This person playing the game was much more interactive than the first one Jake had attended and was typing away in the chat box to Michelle and Jake. Michelle was reading the chat box while gripping Jake's cock and only occasionally and idly moving it up and down. Jake for his part couldn’t get enough of moving his fingers down Michelle’s pants. It kept getting wetter and wetter and Jake could feel folds of skin but had no idea what his fingers were doing. Michelle finally released her vice grip on Jake's throbbing dick and pointed to the next set of points she was going to earn.

Jake was disappointed as her movement meant he had to pull his fingers out of her pants too, but realized that in a moment he was going to get a better view. As Michelle turned around to drop her sweats and show her backside to the webcam, Jake snuck in a quick lick of his fingers, he always wondered how it would taste but it didn’t taste like much to him but still made his head feel fuzzy.

Michelle had finally turned around in her seat and dropped her sweats halfway down her thighs giving a long look toward the webcam. As she was doing so the chat box revealed he could earn bonus points if he touched her right now. Jake was quickly losing his inhibitions and turned to get a close up look at Michelle’s pussy. Jake stares at her gorgeous round butt cheeks and followed the line between her cheeks down till it no longer separated her butt but now separated two thick smooth chubby lips. Jake was intrigued by the line between her pussy lips and he stared intently as Michelle shook her backside ever so slightly at the computer.

“You have to touch me,” Michelle whispered.

Jake reaches out his fingers, than pulled in all but his index finger. He pushed it forward as it slipped between Michelle’s two thick pussy lips. Jake pushes in but his finger won’t go any further. “Is that it,” Jake thought. Michelle sensing Jake couldn’t find the right place, puts her hand on her ass and spread her cheeks, which had the effect of separating her pussy lips as well. Jake's eyes moved from newly exposed butthole down to her pussy, where the spread lips had broken up the seamless line from her ass to the top of her pussy mound. Jake stared intently at the enticing gap that had stretched apart at the base of her pussy, noticing for the first time a soft shade of pink between the separation of her pussy. Jake's eyes were wide and his mouth seemingly permanently unhinged and open. As he looked down into her hole he could see a deeper shade of red inside and a bit of glistening moisture. This worked like a bulls-eye and having first pulled his finger back, now Jake pushed forward aiming right for the hole that was much lower than he would have thought. Jake watched in slow motion as his index finger entered her pussy. Felt with pure joy her skin wrap around his finger enveloping his digit in warmth. Jake began to pull his finger back and forth mesmerized at watching a part of him go into a part of Michelle. Unseen by the camera or Jake, who could only see her backside, Michelle leaned into her chair and closed her eyes even pushing her bottom in and out in timing with Jake’s finger.

The moment seemed too short but soon enough Michelle was following a new set of directions. Michelle looked wide eyed from the screen back to Jake and whispered in his ear. What he heard immediately made him nervous. But compliantly he laid down on the floor to the side of the chairs. Michelle pulled the webcam from the computer and placed it near Jake on the carpet. Jake pushed down his shorts, immediately revealing his rock hard boy cock which popped out of his shorts and sent droplets of pre-cum across Jake's thigh. This was a landmark moment for Jake, who had never noticed pre-cum before, but was washed away with the oncoming wave of sexual arousal and anticipation.

Michelle rested on her knees beside Jake’s side and brushed her hair behind her ears. She brought her face next to his cock inspecting it closely. Then she opened her lips and began to slide her mouth over his penis. Jake's penis was growing, not just here and now, but maturing and getting bigger. But for now his 4 inches of length and minimal width was just perfect for Michelle to completely engulf his penis as she slid her lips down his cock and reaching the base where only the barest of soft fuzzy hair resided.

Jake pulled his head off the floor, where despite the discomfort to his neck, he was able to witness Michelle moving her lips from just under his penis head to the base. Michelle was taking her time, so unlike Lydia who had seemed revolted at the thought. Jake had been nervous he would come again but found himself able to hold out as he felt incredible wet warmth slide up and down his penis. Followed occasionally by the tickle of Michelle’s tongue.

Jake was sadly interrupted by a soft beep indicating more had been typed by their anonymous friend. Michelle pulled her lips off of his penis, in that one motion almost causing Jake to cum. Jake sat up on his elbows with no idea how much luckier he was about to get.

Michelle came back to Jake and stared at him, “He say’s we can win the game if we put it in.”

“Wha ... what?”

“If I sit on it and put it in we win the game, should we do it?”

Somehow avoiding the term “sex” kept the veneer of fun innocence that this game had never been. Somehow not saying “fuck me” meant they could just try this out with no consequence. Jake gulped, and then nodded. Michelle pulled her sweats all the way off, stepping out of her panties. Jake looked up at this angelic girl, with her dirty blonde hair tipped blue and pink, her disproportionately long smooth legs, and her bare chubby pussy. Then afraid of sensory overload he laid his head back and closed his eyes. Michelle positioned herself over Jake's penis and then sat down. This did not work as easily as Michelle had thought and Jake's penis was now over to the side. Jake murmored discomfort with her weight now sitting on him and his penis, so Michelle tried again this time staying on her knees and holding her weight as she sat down. Jake's penis had come right back to attention and stood stiff and straight, Michelle could feel something hard down there but could not get it to enter her.
Then came the heart pounding noise of a car pulling up to the driveway. Michelle’s eyes opened wide in terror and she jumped up and ran to the window of the room. Jake popped up and clumsily maneuvered next to Michelle his hard penis flopping and getting in the way of his movement.

“Oh my god, you have to go now.” Michelle whispered to him, as if that would prevent them from getting caught.

Jake was already pulling up his pants as Michelle unceremoniously turned off the computer. She directed him down stairs and to the back door, giving him a hug just as he exited. Jake ran and hopped her backyard fence, not looking back until he had passed another house, crossed the road, and was in the backyard of a third house. Jake still needed to grab his bike but needed to wait until some time had passed, and he was no longer at risk of a heart attack. Now that he was catching his breath the thought of what had just down had re-woken his penis. Jake went behind a couple trees and peered around, before taking out his penis for a quick jerk. He absolutely could not wait for that until he got home.

Despite his outdoor relief, by bed time Jake found he couldn’t stop thinking about the days events and how technically his penis was touching Michelle’s vagina. Was he even a virgin anymore, Jake wondered as he rested his head against the wall in his showered. His penis was incredibly stiff and he found himself idly tugging at it. Soon Jake found himself rubbing his cock to a purpose. In his horn crazed mind Jake was trying anything to emulate the sex he had almost had today. Desperately he peeled off the cover to his shower drain and try to fuck the hole. Then came the shampoo as lube, followed by trying to fuck the shampoo bottle. Jake couldn’t stop thinking about Michelle’s beautiful hairless pussy lips, her adorable puckered asshole, and the feel of her mouth engulfing his cock. Finally knocking at the bathroom door indicated he had been in the shower too long and needed to hurry up. Jake was quick to relieve himself the old fashioned way. But had he not been in the shower with water running over his hands, perhaps he would have noticed the subtle change in the texture of the liquid coating his hand and penis. Perhaps he would have felt the beginnings of pre-cum leaking around the tip of his penis head. Today’s events had jump started something inside Jake. Something that could not be stopped and could never be reversed.

Sunday was excruciating. Jake couldn’t stop thinking about the incident with Michelle, and as a consequence his penis was hard most of the day and he was unable to take bathroom breaks long enough from his family to relieve the problem. But it wasn’t just that he almost lost his virginity, he also couldn’t stop thinking about Michelle.

The first time they played the game Michelle hadn’t wanted Jake to touch her, she had directed him to Lydia. Clearly, he thought, she knew then he had a crush on Lydia. And the pretext to them hanging out was to talk about Lydia. But after what just happened Jake was supremely confused. Did Michelle like Jake? Or was this all some game to her? Jake not only had to contend with a frequent erection, but a deep pit in his heart that he hadn’t felt since the summer he realized he was in love with Lydia.

“What to do ... what to do.” Jake thought. Desperately out of his league.

Michelle was the one of the prettiest and most popular girls at school. Jake had thought of himself as a loner until he had joined the basketball team. And he had always wanted Lydia. But Lydia had pushed him away and away, and in all that time Michelle had been smiley, and nice, and wanted to be around him, and she smelled good. Jake wasn’t sure what that had to do with the problem, but he felt it was important.

Jake began formulating an idea, a plan of action for Monday. This resulted around a very strange decision he had made, one that would have seemed unthinkable only a couple weeks ago. Jake took one last deep breath Sunday night before going to sleep, willing himself courage for tomorrow.

At school the next day Jake had B-lined right for Michelle’s locker in the morning, by passing his usual hover point near Lydia’s locker. He approached her locker his heart already beating fast at the sight of her. Michelle's shirt jean shorts, her absurdly long and skinny pale legs, and her just rounding bottom were the focus of Jake's eyes. At least until Michelle turned around to face him. Then he was entranced by the sparkly shade of green painted around her eyes and the smile on her face that was the only thing that could calm his inner anguish.

“Hey” Michelle greeted him.

“Uhh hi, I was Uhh thinking that we should talk again today, like Saturday. You know to figure things out. About Lydia. Right?” Jake tried his well planned excuse.

Michelle eyes him suspiciously in a look so cute it once again melted Jake’s insides

“Hmm, I think you just want to play the game again.” Jake tried to stutter an excuse but failed spectacularly. “We need to see if it makes her jealous. Otherwise you need to be hanging out with Lydia somehow. Stay focused Jake! Besides my mom is gonna be at the house today so we can’t”

Devastation flooded Jake’s body, from deep in his chest to deep in his mind.

“Well maybe another day?”

“I’ll check. Maybe Thursday. My moms keeping me really busy this week.”

Thursday? Thursday?! That was an eternity Jake thought. So caught up in his despair Jake didn’t notice Lydia coming up the hallway.

“Jake you look weird.” Lydia commented before taking the ear of her friend away from Jake.

Jake watched the girls walk away. What had gone wrong. Thought Jake. He spent the day feeling out of sorts. Every tine he saw Michelle his heart skipped a beat and then his penis betrayed him, rising to uncomfortable proportions and requiring clever maneuvering most of the day to remain unnoticed. Jake was somewhere between crying and jacking off. Undecided he wondered if he could escape to the bathroom during class to do... both he guessed.

Despite the school day feeling infinite, Jake eventually found himself in his last class groggy from the emerging spring heat stuffing up the classroom. So he was surprised to find Michelle had somehow found an excuse to enter his class. Did she know it was his class? He wondered. Michelle always found a way to bypass any rule she found inconvenient. His thoughts were answered when as she slipped past him on whatever errand she had concocted up she left a note on his desk.

“Moms taking sis to soccer at 4 u can come then.”

Jake's spirits soared as he read then reread then read the note again. The day’s despair blew away and a juvenile excitement filled Jake. Jake was too entranced after class trying to find Michelle in the halls but her mom must have picked her up already. He brushed by Lydia asking him something. Grunting an answer he could only think about getting to Michelle’s house.

Once on Michelle’s street Jake realized he needed to stay out of sight for another hour. Pacing the street was unproductive and slow. Eventually Jake found a boy with a curbside basketball hoop and played 20 minutes of terrible ball with his mind and penis completely distracted. Ten minutes before he could even knock on Michelle’s door Jake ditched the game unceremoniously and hovered behind bushes across from her house until he saw a car leave the driveway. Eyes looking in both directions Jake sauntered over to Michelle’s front door. Breathing heavily and trying to slow his pulse Jake knocked on the door.

Michelle answered it with a smile her hands seeming to grab his shoulder in slow motion and pulling him in the house. Jake's senses were heightened with his nervousness and he could feel the heavy air brush by him as they moved upstairs, past the computer room they normally hung out in, and into Michelle's bedroom. Michelle motioned for Jake to sit by her, and he did. Sitting next to her, the inches between them felt like no distance at all and he could feel the presence of her body next to his even when he wasn't looking. Michelle sat expectingly for a moment before she decided to start the conversation.
"Sooo...I bet you want to play the game again, but you know we can't my mom will be home too soon." Michelle started.
"No, no, I didn't come here about the game."
"Then what is it?"
"Uhh, well, I thought we could you know finish our conversation from the weekend." Jake managed to stammer.
"Oooh, about Lydia, of course" Michelle replied while giving Jake a sly look. "Yea well I did talk to Lydia today about playing the game this weekend, I mean I didn't tell her how many more points we got and all the new things we did. But she seemed more mad with me than jealous about you. So we might need a new strategy."
"Well about Lydia, I kinda think I don't like her any more..."
Michelle's mouth gaped open, half in a smile and half in dramatic surprise.
"What, Jake! All this work for nothing, come on ... I am trying to help you out here."
"Well I mean, I like somebody else now."
"Ugh your such a boy. Lydia and you are perfect for each other, friends forever .. neighbors .. and your both my friends so it works out great."
Michelle had never called Jake her friend before, but he guessed that is exactly what had happened in the last couple months with their shared math class. The word was a blessing and a curse at the same time.
"Look if this girl is some nasty slut I don't like its not gonna be ok..."
Jake could feel the words he wanted to say rising from his shakey stomach, but they kept getting stuck, first in his chest ....
"Because I think I can get Lydia to like you, she really doesn't like any guys right now, so why not you ..."
Then his throat ...
"And you shouldn't give up, I don't know why she's been so cold but ..."
Then on his tongue...
"Seriously I am one hell of a match maker ..."
"Michelle!" Jake exclaimed, stopping her from talking. Wow, he thought, that was louder than I meant it to be. There is no going back now.
"Uhh its you."
"I uhh .. I like you."
Seconds felt like hours as Michelles face turned from surprise into a huge smile, a smile that instantly relieved Jakes cold body, filling it with nervous warmth.
Michelle pulled Jake in for a huge hug, Jake's spaghetti arms hugged her back. Then he pulled back his face so it was only inches from hers, her gorgeous brown eyes with green sparkly eye shadow staring right at him.
"Jake, I ..."
"I guess, I dunno when, but I think I love you."
Michelle, never hesistent to take what she wanted, immediately moved in for  a kiss. They missed. Jake nervously went to complete their failed transaction, and this time noses brushed but lips did not meet. With his pride and manhood at stake, Jake calmed himself enough to swoop in steadily one last time and kiss Michelle. Their lips met, poking out and pressing against the others. Like two unyielding pyramids of pink flesh they pressed against each other until they needed to breath. Michelle pushed Jake back, pressing his back against her bed and climbed up on him to continue their make out session. Jake  was in heaven. But never  one to leave things as is, Michelle pulled away from their kissing, smiled at Jake, and began to move downward to Jake's mesh sport shorts.
"Wait ... I thought we didn't have time, your ... your mom is coming home?"
"For the game silly, that takes forever. But now that we are going out we don't need a game, we can do whatever we want and do it way quicker. We are going out aren't we?"
Michelle sat up looking at Jake. Jake decided to act fast.
"Michelle will you be my girlfriend?"
"Of course!"
Michelle returned to her previous position and reached a hand into the waistband of Jake's shorts. She felt around for a moment before grabbing his penis and inexpertly moving it around a few times. Jake's face gave away his hope for more. Michelle pulled down Jake's shorts to his knees and his slim almost hairless member stood at attention after whacking his stomach from the pulling of his shorts. Michelle smiled at Jake before once again engulfing his entire penis in her mouth, her lips resting at the bare fuzzy base of cock. Had Michelle been a bit more experienced she'd could have also licked his balls while having his entire penis in his mouth. She began to move her lips up and down Jake's slim shaft. Her saliva mixing with something she had never noticed before, pre-cum drizziling down his penis. The combined wetness hid this development from both Jake and Michelle.
"Oh my god Michelle" Jake moaned.
Michelle was not particulary talented, but it was also unnesscary. She had his entire penis in her mouth at once, and performed an adequate up and down movement, blowing Jake literally as well as his mind, figuratively. Jake pushed his slim hips upward each time Michelle pulled back. He managed to look up at her to watch her beautiful face moving up and down, with her gaze downward toward his penis, he could see her shimmering green eye shadow and he puckard lips. Unceremoniously Michelle pulled her mouth away. Jake was dissapointed but would not be so for long.
"Come on," Michelle said as she began pulling off her shirt, motioning for Jake to do the same. "We don't have long."
"What ..."
"I want to try something, I have been getting myself ready I think we can do this if we do it real quick."
Jake's mind tried to race through the possibilities but only one continuously came to the forefront. "Oh my god, oh my god, we're gonna do it." He thought. Jake's unsteady hands pulled off the rest of his shorts, and followed through with awkwardly pulling his shirt off, getting his head stuck for a couple seconds too long to play off. When he could see again, Michelle was resting on her back on her bed sheets. Her skinny bra was still on, but she was otherwise naked. Her legs were spread and Jake could see with absolutely clarity her pudgy bald pussy lips, peeled back enough to give a strong hint at the pink wetness within.
Jake moved over to her at once, forgetting to remove his socks. Jake had to look closer, he just did. He placed his fingers against her pussy lips and spread them. The view was unforgettable to Jake's impressionable young mind. A chubby bulb of flesh up top, which led downwards into a ring of skin that looked so different from what was on the outside. He had peeled her pussy enough to see a a darker wet redness inside of that ring. Jake moved his hands upward to spots on either side of Michelle's shoulders on the bed, scooting his butt awkwardly because of his hard cock flapping as he moved, right between Michelle's knobby knees. Her smile was as big as it was expectant. Jake had no sense to position his penis, or direct it firmly with his hands, he just laid gently on Michelle and began pushing.
The first couple thrusts hit everywhere but the target. An impatient Michelle finally took matters into her own hands, wrapping her fingers around his penis and putting it exactly where it needed to be. Jake pushed again and was rewarded. His slim cock entered unhindered. He felt a tunnel of warmth and wetness slid around his cock. Jakes instincts took over and he began to thrust at pace equal to his heart rate, in and out, in and out. This young adolescent was losing his virginity to one of the most popular and beautiful skinny little middle-schoolers. Each thrust pushing him as deep as he could go into the soft and soaking freedom of Michelle's pussy. From an overhead view one could have seen his skinny little butt pumping up and down, in and out, tightening and flexing as he barreled into Michelle. Michelle stared at her adorable boyfriend, his face wrapped in ecstasy, his tight chest appearing only for moments between thrusts. She pulled back her knees more to relieve some pressure and set her head back, closing her eyes and trying to find his non-existent rhythm, after her practice sessions since their botched attempt over the weekend, this indeed felt good once she set her mind to finding the pleasure.
Jake peeled back his hips for a moment, realizing the whole experience was flying by. He wanted to see himself enter her. With one hand on his hip, he looked down. His hard cock was buried just partway inside her thick pale pussy lips, now more flushed and engorged than before. He could see wetness coating his shaft. He pulled back slowly, trying to get a close look. Watching just the very base of his purple tip pull out of her, before pushing back in. This slow down of motion feeling teasingly good to Michelle as well as Jake, just gaining a concept of how sex could feel different. These long steady slow strokes into her perfect bite-sized vagina, melting his dick from point of entry to base as he pushed and pulled. Watching her chubby lips completely absorb his stiffness. Looking up from her pussy he could see her pale tight stomach leading toward her almost flat chest with an adorable thin bra covering it. Her face, eyes closed, mouth slightly ajar, was more beautiful then ever. But his eyes were pulled back down to where they met in the middle, watching himself enter her again. This was too much for Jake. He felt a familiar sensation, accompanied by an even more intense boiling deep in his loins. Jake almost fell on her, catching himself just in time.
Their chests pressed against each other, their heat and sweat shared, Jake began to jack-rabbit once more into his young new girlfriend. Warmth and wetness meeting him each time. Less than a dozen fast short strokes took him to a bliss he could compare nothing to it, and a spurting feeling from the tip of his penis simultaneously painful and pleasant. He lurched forward a last time, grunting before falling onto Michelle. Michelle wrapped her arms around him as he shuddered and lay in peace. Eventually, finally, Jake rolled off, his cock plopping out of her, drips of his first cum on the tip and down the shaft, hard but slowly shrinking. Michelle inspected her self...
"Jake, I think you came."
"It was amazing."
"No like there's cum."
Jake looked down first at his cock, then at the little bit of semen oozing from Michelle's still tantalizing pussy.
Michelle laughed.
"I think we're gonna have to get condoms."
"Maybe I can steal some from that joke store at the mall"
The two young lovers lay for a few moments before Michelle reminded Jake he needed to leave before her mother came back.
"I can't wait to see everyone's faces at school. I am so happy we are going out." Michelle told Jake.
"I have the prettiest girlfriend in all of school, I can't believe it." Jake complemented her. "I really really like you Michelle."
"I love you too silly. Took you too long to notice though. I thought you were still into Lydia, I was just trying to help you out. Oh ... Lydia, oh do you think she will care?"
"I dunno but I don't care who knows I love you."
"Except maybe our parents," Michelle giggled. "Wait do you think we could get Lydia to join us? Oh my ... we have to make it happen ..."
Jakes mind was swimming with possibilities as he went home that day. The day he became a young man. The day he got over his little crush and realized he loved Michelle. Jake had no idea how lucky he was. He was well fucked that day, but it did not stop Jake from relieving himself again before dinner, and again in the shower, he couldn't help it, every time he thought about the afternoons events.
« Last Edit: January 30, 2020, 03:43:55 AM by Ace MD »

My stories:
Joys of Porn - A teen shares his hobby with a neighbor.

Wandering Eyes - A boys crush includes him in webcam games.

After Camp - A counselor meets a camper after camp.

Offline cironwalker

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Reply #1 on: January 28, 2020, 03:01:13 PM
This was a great story that I enjoyed very much. It brought back some childhood memories of mine. Thank you for sharing.

Offline Ace MD

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Reply #2 on: January 29, 2020, 09:55:59 PM
Thanks cironwalker! Love hearing feedback and sounds like this story did exactly what it was intended too.

My stories:
Joys of Porn - A teen shares his hobby with a neighbor.

Wandering Eyes - A boys crush includes him in webcam games.

After Camp - A counselor meets a camper after camp.

Offline Uncle Ed

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Reply #3 on: April 25, 2021, 08:43:56 AM
I really like this story.

The evil that men do lives after them; the good is oft interred with their bones. - William Shakespeare

Offline JadeGreen

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Reply #4 on: April 26, 2021, 10:01:00 PM
Great, well written story. It reminded me of a similar situation I had with two girls in my youth, but didn’t go as far (except in my fantasies)