Chapter 3: The Young Slut Later Known as Kim

The following is the beginning accounts of Kim’s experiences, before she was known as Kim. These are 100% factual and nothing has been elaborated on in an attempt to make the story more exciting. This series is a collection of short stories that can be remembered in most detail and though written in the third person, is all my (Kim’s) experiences up to and including a Scouting trip that helped to push her into being the cock whore she is today. It will be made up of many stories and many chapters covering her life.

This story isn’t suitable for everyone, but it is my younger life, a huge part of me, and what made me who I am today, someone that loves to please you all with pics and vids. Someone who loves to meet strangers, older men, and make them cum.

• Kim will be used in place of my real name because that is who I am today. However, the name Kim didn’t exist until after the camping trip which concludes this series of short stories.

• The other names in the story, have not, been changed. Maybe the participants will see this one day and realize that their friend, now Kim, is still out there and willing to show them what she has learned.
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Prelude to Chapter 3

Kim had struggled in school the past few years. She was always the youngest in her class and people were maturing faster than her. She was struggling to hold any good grades and her teachers were concerned for her.

Kim’s parents made the decision to pull her out of school for a few years and homeschool her. If you don’t know, the homeschool community is pretty big and they have a lot of social activities. Kim began the next few years of her life in that community, still friends with Phil, but not nearly as close as they once were.

Homeschooling led to a lot of life experiences that helped to shape who Kim was and it also led to her being home a lone a lot. Though she was supposed to be studying, she found herself online most of the day, caught only when her parents tried to call her and the phone line was busy with the 56K modem.

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1: Learning Skills and Toys from the Internet

The internet opened Kim up to an entire new world. Now, everyday she spent online, in chat rooms and finding, what she thought was girls, to trade nude pics of themselves. The lesbian rooms were a thing of the past and now she just found herself in any chat room, pretending to be the girls in pics that she found, and luring older men to chat with her. She would always ask for more pics of girls from them but she loved reading what they wrote to her as they jerked off to the pics she sent them.

Kim was really getting good at the dirty talk and she was getting so turned on by pretending she was a girl. She was also learning a lot about sex. Not real sex, but porn sex and to her, that was what real sex was. Her homeschooling education didn’t really have sex education in it, so this is what Kim was learning about sex, and she loved it. She still wasn’t cumming but that was probably a good thing. Instead, there was nothing to stop her from being horny and she would just continue all day long, searching the internet, chatting with old men, and looking at naked girls.

There were a few times that a man would call her out and ask if she was a guy. Usually she would deny it, but sometimes, the conversation felt right to admit it. When she did, the next question always was “how old”, she would always tell the truth there and it almost always turned into an even better conversation than before. These older men, loved her age and loved that she had experience please cocks, they didn’t seem to care that she was a guy as long as she was gonna treat them like she was a girl. These conversations changed her even more than just finding access to porn.

These men were very sexually explicit as they chatted with her and she learned more and more what pleased them. She began to actively “cyber” with them. A term that was new to her but she loved it. She would chat with older men, sometimes pretending to be a girl, sometimes being herself but acting like a girl in the role play fantasy of these men. They would both jerk off, but the men would cum and leave and Kim would look for a new person to chat with, repeating the cycle for hours a day. She was obsessed.

During this period, Kim and Phil saw each other less and less. They didn’t complete stop hanging out but it was def changing and changing quickly. A few years earlier they were meeting up almost every day, now and especially during the school year, it was barely monthly. Kim did take any opportunity to show Phil what she was learning online, though she never admitted to where she was learning these things. Mostly, it was things she knew but she was learning about passion and that was the difference. Instead of licking and sucking on Phil’s balls for a few minutes, she would slowly, passionately lick his ass hole, lightly flicking his balls with her tongue and softly sucking one ball at a time into her mouth.

Kim learned the art of teasing him and would get into the 69 position with him, but not let him do anything but look at her as she worked him. She would suck him, take him close to cumming and then stop sucking and move to licking him again. Kim was taught by her internet men about sloppy blowjobs and began really drooling on his cock, then using her hand to stroke him as her tongue worked his hole. She as taught about deep throating. Though she and Phil had always done deep throat as just part of the routine, she learned about how important it was to keep it down her throat for longer, which was becoming much more of a thing as Phil’s cock was quickly growing and it seemed like with each meeting it went further and further down.

Throat fucking was a new thing that she added to their meets. They had, in the past thrusted their hips up on each other, but it was a non-event with their size and usually was just a joke. But after a long conversation with a man online about it, Kim was ready to try it.

“Stand at the end of the bed” Kim told Phil, both of them in her room, completely naked.

They were home alone again, a common occurrence as Kim was home alone almost daily. It wasn’t a big deal, Phil’s parents were a few houses down the road all the time though it was nice to not have to worry about being walked in on though and both boys had their clothes in a pile on the floor. Phil was starting to get short dark hair growing on him and though it wasn’t as much as Nick had when Kim first experienced it, it was darker and more noticeable. It was also making it more noticeable that Kim still had nothing.

Kim an her slim, completely smooth body lay on her back on the bed. She hung her head upside down off the edge of the bed and looked at Phil, standing there in front of her. His cock was thick and though not as big as Nick’s was the summer before, it was getting there quickly. Kim was almost bashful of her size and lack of hair but that didn’t stop her from what she loved doing.

“Ok, put it in my mouth” Kim said

Phil stepped forward and Kim, upside-down, opened her mouth. He slid into her warm mouth and he took her hands and wrapped them around his upper thighs, pulling him in closer. Phil didn’t need to be told what to do, he too was learning things on his own and knew exactly what this was. He begin to throat fuck her, not very fast at first but in and out he went.

Kim handled it well and was able to take it all the way in and out without gagging. Phil continued, all the way in and all the way out as spit begin to build up quickly in Kim’s mouth. With her hands on the back her his thighs, Phil leaned forward slightly and slid his hands under the small of her back. Here he begin to thrust faster. Kim still handled it but now spit was going everywhere. Thick bridges where falling from his cock and down her face with each pull out and were now dripping onto the carpet below her head.

Suddenly, she gagged. She had never gagged but the repetitive deep trusting was leaving little time to recover and Phil was going as far in as he could. Phil quickly pulled all the way out and a thick glob of spit splattered down her face, running across her eyes and forehead.

“Oh sorry!” Phil said.

“That’s ok, I kind of liked it” Kim replied, laughing

The gagging part wasn’t really what she liked but it caused her hard little cock to twitch and her ass to pucker and all that felt great.

“Your face” Phil said laughing, looking at just how much spit was running down her.

“It feels so funny” Kim said. “Keep going”

Phil didn’t need to be asked again and began to throat fuck her. This time, when she gagged, he would only stop for a second before continuing. She could feel her cock dripping onto her stomach and Phil could see it. He took hold of it and jerked her while thrusting.

Suddenly, the garage door opened. Kim’s room was right above it, a warning that had saved them before. Phil pulled his cock from her mouth, it was soaked but nothing like her face and the wet carpet below her. Kim’s eyes were coated with spit as she grabbed a shirt and tried to wipe herself off. Both boys were trying to clean up and get dressed when they heard the house door to the garage open and Kim’s Mom yell “Hello”. They had made it, dressed and cleaned, but it was close.

Kim’s online experience with these men were totally changing her and she was obsessed with it. Many times she would make up total stories to them and while cybering tell them things she was doing that she really wasn’t but the times that really turned her on were the ones that she was truthful about her experiences and who she was and when the guys were obsessed with that over anything else. It felt as if she didn’t have to be all this fantasy stuff that the men would talk about, just having a young, slut that loved sucking cock and had experience doing it was enough for some of these men and that, was the total turn on for her. That was the case with a much older man that she started talking with.

Bill was in his 60s and met Kim in a chatroom. He was very nice, not forceful and rude like many of the guys on there. Kim immediately felt comfortable talking to him and quickly admitted who she actually was and her age. She didn’t lie to him about her experiences and he was very interested in her life. Bill sent her pictures of girls that he had accumulated, which helped to keep her entertained but in reality, she was just enjoying having such a sexual conversation with an older nice man. He also took a picture of himself both with clothes and naked and sent it to Kim, she loved it. He asked for one in return but Kim had no way of doing that at the time. She had pictures of herself that she was able to scan and send him, but all of them were real pictures and she had no nudes. But Bill didn’t get upset, she would send him pictures from photo albums and he would tell her how cute she was, he loved the pictures and never pushed her for more.

Kim, when she admitted to ppl who she really was, had one lie that she almost always still told, no matter how honest she was being. Almost always, she told people she was experienced in anal. She found the cybering and chatting was so much hotter that way. In reality, Kim had never experienced anal, not, with a guy, objects, or even a finger.

Bill was the exception to this lying rule and as he was asking her things about her experience he said;

“Ever done anything in the butt?”

Kim admitted to him that she hadn’t and that the closest she had come was the grinding that her and Phil had done so many times before.

“Why not” Bill asked

Kim explained that she didn’t know how to start it with Phil. They’re time together was less about experimentation now and more about getting Phil to the point that he would go to the bathroom and jerk off. He didn’t seem nearly as interested in her as he was girls and it was just a weird thing to bring up. She was asked about toys, which she explained she didn’t have any nor did she ever find any in her house.

“Anything can be a toy” Bill said.

Kim remembers that line as it was almost like that was never considered before. She had imagined girls being able to do that in their pussy but it never dawned on her that anything could be a toy in her boi-pussy.

Kim had sent Bill a picture of her in her living room. She wasn’t wearing a shirt in the picture and it was the closest to sexual that she could come up with, but in that picture, sitting on the coffee table was a wooden back scratcher. There was nothing fancy about it. The rounded handle was long and very thin, maybe the width of 2 pens, but, at the end was a red wooden ball. This ball wasn’t big either, but it was bigger than the handle and about the size of a large marble or the diameter of an adults thumb. Bill must have been looking at that picture during this conversation because he said;

“The back scratcher in the picture you sent would work fine”

Kim knew where the back scratcher was but she had no idea how to actually do it. She admitted that she was nervous and that she didn’t really know what she was doing. Bill, still not pressuring her, suggested that she put a little vaseline on the ball and a little on her hole. To lay on her back and relax while she pushed it in. Her stomach had butterflies, she wanted to do it but she was nervous for some reason but this is where Bill put on a little pressure.

“Do it for Daddy” he said, “Tell me how you like it”

It was the middle of the day and Kim was home alone again. She was at the family computer which was downstairs in the “computer room” but she was going to do it. Nervously she found Vaseline in her parents medicine cabinet and went back downstairs to the computer. She stripped down to nothing, her hairless, flawless body on display and her small cock hard. She typed to Bill as she moved step by step, putting a small amount of Vaseline on the ball of the back scratcher before laying on the carpet and putting some on her hole.

Kim was laying on her back, on the floor in front of her computer. She couldn’t talk to Bill anymore but he was sending her pictures to help motivate her. Kim placed the lubed wooden ball against her hole, took a breath and pressed. Just like that, Kim lost her anal virginity to an object. She was surprised how easily it went in and was shocked on how good it felt as it popped in, her hole tightening right back up against the wooden shaft. For a few minutes she moved it in and out, slowly, loving the feeling of it each time it popped in and popped out. After a few minutes she pulled it out and went back to report it to Bill. Kim can’t remember much more of the conversation after that but she had taken a new step.

Kim had now found another way to please herself while she was at home all day. For the next few weeks she would play with that back scratcher almost daily, in all different positions. She put it between the seams of her chair bed and would hover over it, sliding up and down as far as she could go. She would lay on her back with her legs up and she would lay on her stomach with her ass up, all different positions. But now, she was on the hunt for more “toys.”

It didn’t take her long to find all sorts of things. A small circular hotel shampoo bottle, sharpies, a plastic plunger with ribs, and a shower brush with a thick handle all became her usual suspects. The shower brush was her challenge as she wasn’t able to take the handle to its widest part. She was playing so much now that she had to stop using the vaseline in fear that she would run out. She moved to lotions and once again, her favorite, the aloe gel. Looking back on it, her parents must have always wondered why the smell of aloe was always in the house, but they never asked and she just kept playing and playing.

Kim never talked to Bill online again, but that man changed her and she was now fucking her ass with whatever she could almost daily. Soon, she would take that to the next level.

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2: Losing Her True Anal Virginity

The summer was just about over and Kim had barely seen Phil at all. They hadn’t played in months, though she had been incredibly active with herself and her new “toys”. She hadn’t really worked up to anything bigger, though on a few occasions she was able to get the widest part of the shower brush into her. She was loving playing with her ass and on more than a few occasions she was left sore the next day from her self play.

Finally, with only a few days left of summer, Kim and Phil got a change to hangout alone. Phil had been the one that was really starting to dodge her. He was more and more interested in girls and less and less interested in her. He had a “gf” that summer and spent most of the time with her and even when Kim did she him, he never wanted to play. Today was different.

Phil was over Kim’s house and her parents weren’t home. They had made their way to her room, where the hot afternoon sun was shining brightly into her windows. For a few minutes they just talked, but it was clear to Kim that Phil wanted more this time, and she hadn’t wanted it for months. There was no setting the stage, no back story, no role-playing; Kim just put her hand on Phil’s basketball shorts, felt his cock, and started rubbing, looking at him as their conversation stopped.

Within seconds Phil’s cock was getting hard and Kim moved her hand down his pants and slowly started stroking him. Phil responded by reaching out and sliding his hand down Kim’s pants. She too was hard and for a few minutes they just stood there, stroking each other. Phil made the next move. Pulling his hand out of her pants he took hold of her shirt and lifted it up. She had to pull her hand from his pants to let Phil take her shirt off. He dropped it to the floor before removing his shirt. It was Kim’s turn and she reached out, taking Phil’s shorts and underwear in her hand and pulling them down to his ankles, kneeling in front of him as his hard cock popped out and into her face.

Phil stepped from his shorts and now, cock hard in her face, stood in front of Kim with nothing but socks on. His cock was thick, much thicker than hers and thicker then she remembered from the last time. He was growing fast and it surprised her.

“Wow, your huge” She said, looking up at him as he looked down at her

Kim didn’t wait for instruction and for the next few minutes she knelt in front of Phil and worked his cock in and out of her mouth. To this day, she can specifically remember the feeling of how thick he was and how much of a surprise it was to her. She touched herself with her free hand as she continued to suck Phil’s cock, occasionally lifting it up to lick his balls, which had just a little bit of hair on them.

After a few minutes Phil reached down and slightly pulled Kim up, coercing her away from his cock and back to standing in front of him.

“Lay down” he said, pushing her lightly towards the floor.

Kim obeyed and laid down on her back on the floor, the carpet lightly scratching her back. Phil squatted down in between her legs and removed her shorts, tossing them into the clothes pile. Both boys were now naked, hard, and ready to please each other. Phil slid his arms under Kim’s knees and lifted them up, pressing his tongue right into her balls and begin licking her. She was hairless and tight and the feeling of Phil’s tongue made her lightly twitch as he worked around them and down to her boi-pussy. Her ass was still very tight, despite her spending almost every day that summer putting things in there. She hadn’t worked up to anything too big and it wasn’t obvious that she had been playing. Phil pressed his tongue against her hole and then pushed it in slightly before licking around it again.

Kim was loving it but she wanted to suck on Phil too. She reached down and lightly tugged on his arms, pulling him up onto her. Their bodies rubbed each other as he slid up on her. With their cocks touching, they kissed. It was something they didn’t do often but they did today. Their tongues playing with each other for a second as Phil lightly grinded his hips, causing their cocks to grind together. Kim wrapped her legs around Phil and pushed them over to the side, rolling them over and now putting Kim on top. They kissed a few more seconds before Kim spun around on Phil, pushing her ass towards his face and taking hold of his hard cock, putting it in her mouth once again.

Phil worked on Kim while she sucked him. He took his hands and spread her ass apart, burying his tongue deep against her hole. She sucked him, swallowing his cock all the way in her mouth while rubbing his balls with her hand. He would lick her balls but mostly he was spending all his time licking her hole and she loved it. Every time he pushed against it, she deep throated him and for the next 5 minutes or so, they worked each other just like this. Kim was in heaven.

This was everything they had done before and everything Kim had been missing all summer. Sure she was taking more and more care of herself but she missed the feeling of Phil’s cock in her mouth and she desperately missed the feeling of a tongue on her ass. Now she had both and she was loving every second of it. She began to grind her hips slightly, pushing his tongue harder against her as she worked his cock, slobbering all over it as she pushed it all the way in her mouth and took it back out.
Kim suddenly became aware that she could have more. Her cock was throbbing and the feeling of Phil’s cock in her mouth was making her so incredibly horny. She wanted more, she needed more, and for the first time ever, she knew exactly what it was that she wanted to try with him. Kim pulled her ass from Phil’s face and spun around on him, kneeling between his legs and sucked on him a few more strokes before looking up at him. Her lips and chin were wet with spit and a drop dripped from her chin to the carpet.

“I want to try something” she said, looking at Phil

“Ok?” he said looking back down at her

Kim didn’t explain, it was time. Laying on the floor of her room, the boys that had played with each other for years were about to take it further than ever before. Both were still virgins. Kim was hairless, tight balls, small cock, and a pink wet boi-pussy. Phil had some new hair everywhere and his cock was significantly larger and more importantly wider than Kim’s. Kim swished a little extra spit into her mouth and one last time put Phil in her mouth. This time, she didn't suck him, instead, she just dropped the glob of spit right on the tip of Phil’s cock and used her hand to spread it around lightly. Then, she slid her body up so that her knees where next to his hips and her cock was resting above his belly button.

It isn’t clear when Phil realized what was happening but Kim looked directly into his eyes as she reached back and took hold of his cock, still wet from Kim’s spit. They were both hard as Kim lifted Phil’s cock up and pressed it against her virgin hole. Phil moved his hands to her hips and held them there as she worked to figure out how to get him into her. She tried just pressing him in, but she was too tight. She tried holding him against her and pressing back, but Phil winced as she did. Kim licked her hand and rubbed it onto Phil, then licked her fingers and rubbed them against her hole. Then she tried again, lifting his cock and pressing it against her hole. She leaned forward slightly and felt it.

It begin to stretch her out and begin to ever so slightly slide in. It was most certainly not the easy “pop” that was the back scratcher. This was more of the thick handled brush…but thicker and it kept stretching. The tip was in and her open mouth took quick shallow breaths as pressed harder, still eyes locked with Phil’s. Further she pushed but just past the head she pushed a little too far and the pain took over as she jerked forward, Phil’s cock popping back out.

Kim was determined and slid down Phil’s body and put him back in her mouth, inadvertently doing her first ass to mouth but not knowing that was a thing until much later. She sucked him, slobbering on him, and again, licked her fingers and rubbed them on her ass. This time she was quicker and pressed his cock against her hole, opening it up. The tip slid back in and now she made it further down. It was still hurting but not like before as she went further and further, breathing quickly as she did. She pulled back up a bit and slid him back down, a little further this time, before doing it again, a little further.

On this end of summer day, left alone at Kim’s house and on the floor in Kim’s room, both boys lost their virginity to each other. Though at the time, Kim wasn’t thinking that, she was just thinking about trying to keep Phil wet enough to not hurt, as it was starting to hurt again. Kim pulled Phil out of her again put him back in her mouth. This time, Kim distinctly remembers his cock tasting different; it tasted, like her. She let a big glob of drool fall from her mouth and onto his cock as she looked up at him. He was laying in front of Kim’s fish-tank and on the bottom shelf she saw the solution to her problems. The bottle of aloe that she was always using to masturbate.

Straddling Phil, she reached over his head, leaning down and kissing him while grabbing the bottle of aloe from the shelf, recoiling back to kneeling in between his legs. Opening the bottle, the familiar smell of the aloe immediately was present. She squirted a nickel sized amount into her hand and with two fingers on the other hand, she spread it around her palm. With her hand now lubed, she took hold of Phil’s cock and begin stroking it. He immediately began to twitch with pleasure and she knew she had to be careful not to make him cum. With her aloe covered fingers she reached back and smeared it on her now, slightly stretched, boi-pussy. Kim slid back up on Phil, straddling him, leaned forward to kiss him, and took hold of his cock. She once against pressed it against her hole as he put his hands on her hips. She sat up from kissing him and sat back on his cock. This time, it slid right in.

It still hurt, but it wasn’t like before. It was sliding in now and that made it feel so much better and she pushed through this pain, taking quick shallow breaths. Phil was pushing on her hips now and within a few seconds she had him completely inside her. She leaned forward, breathing fast while the pain subsided a bit. She felt full. It was completely different than with the objects she had played with before. All of them were smaller and not only was Phil’s cock bigger, but it didn’t get smaller, it just kept filling her up.

“What does it feel like” Phil spoke the first words to her since she reached down his pants 15 minutes before .

“It’s good. It hurts” she replied still resting her head on his should and not moving.

“What does it feel like for you” she asked

“It feels really good”

Kim pressed her hands into Phil’s chest, sitting back up. A small bridge of precum stretched from her small clit to where it had rested just below Phil’s belly button. There was a feeling that was making her want to move her cock or squeeze her ass tight, when she did, another big drip of precum followed the bridge and created a tiny puddle on Phil. She was now sitting straight up, her knees next Phil, his cock all the way in her and her small hairless cock sticking straight out. She looked at him as she slowly started to move up and down on his cock.

It didn’t hurt anymore. Instead, there was just a feeling of fullness in her. That feeling was hard to describe but she really liked it. Kim was still moving slowly up and down but every time she went down, there was a feeling that made her cock twitch a little and she wanted more of that. Phil was still holding her hips and now he began to slowly push his hips up and down in rhythm with her, effectively speeding up her motion.

Kim was really enjoying the feeling now and she sped up a little bit more. There was now a distinct sound of their bodies coming together along with the sound of the aloe that had dripped down Phil’s shaft. This combined with her short rapid breathing and Phil’s increasingly heavy breathing lead for an erotic scene unfolding on the floor of her room. Their eyes were locked together and Kim wanted to lean forward and kiss Phil, but she couldn’t do both and the pleasure she was feeling was greater than her desire to kiss him.

“stop stop stop” Phil suddenly let out as he dropped his hips to the floor.

Kim didn’t want to stop and kept going but Phil squirmed and lifted her up enough that his cock fell free. His cock popping out of her, especially that quickly, was a totally new feeling and it was incredible. Her small clit twitched hard 2 or 3 times with a big drop of precum falling from her tip and into the puddle that had formed on Phil’s waist, just below his belly button.

“oh my god” Phil breathed heavy as he grabbed his cock, trying to hold back and orgasm.

Kim slid back and knelt between Phil’s legs, watching his cock and slowly stroking hers. She could see the puddle she had created on him and the feeling that she felt in her ass at that moment had her so hot. It had been a minute and Phil had successfully prevented himself from cumming. His head was back and his eyes were closed as he dropped his hand from his cock and to the floor. Kim leaned forward and flicked his balls with her tongue, then licked around the base of his cock and up to the precum puddle on his waist. The taste of aloe was strong but the salty taste of her precum overpowered it as put her lips down on it and slurped the little puddle up. She had tasted pre-cum before, squeezing it out of Phil and herself and she loved the flavor.

“That was really good” Phil said, picking his head up to look at her.

“Will you try it” Kim asked him

Phil was definitely not the bottom that Kim was but they had always done the same things. Though Kim would suck Phil more, he would suck her, so it was logical to ask him, but looking back on it, it wasn’t for him.

“Ok” Phil said, almost nervously as he sat up.

Excitedly, Kim flopped down on her back on the floor next to him. Phil picked up the bottle of aloe and put some in his hand, spreading it around just as Kim had a few minutes earlier. As he knelt in-between Kim’s legs, like she had done early to him, it was very clear just how much thicker he was than her. He took hold of her small cock and rubbed the aloe on it as he spread some on his ass with his fingers.

“That does feel good” Kim said, putting her head back against the carpet.

For a few seconds Phil rubbed Kim’s cock with his aloe covered hand, then, he straddled her, sliding up to her waist and took hold of her cock. He picked it and put it against his ass. Just the sliding between his cheeks felt good with the aloe. Kim felt the tip of her cock press into his hole and slowly spread it open. It was tight, like when they would really suck each other hard. It was like a slow, tight, lubbed hand was sliding down the tip of her cock and it felt really good.

“OH Fuck!” Phil said as he lifted himself up. “That hurt so bad!”

“Go slow” Kim said, wanting the feeling again.

“I don’t think I can” Phil responded

“Please” Kim replied looking at him

Phil lifted her cock up and once again pressed it against his hole. Again, it slowly spread him open and this time he went a little further. Kim didn’t help things however and pushed her hips up, pushing her cock into him. It slide all the way in with little resistance and for a brief second Kim was completely inside Phil.

“OW!” Phil cried out and jumped up grabbing at his ass and pacing around the room completely naked.

“I’m Sorry” Kim said sitting up too

“How were you able to do that?” Phil said to her.

“I don’t know, it didn’t hurt me like that. I actually liked it” Kim replied.

Phil took a seat next to Kim and both boys sat there for a few minutes completely naked. Kim was still stroking her cock and she reached over and took hold of Phil’s. Just the size feeling in her hands was so different, it was surprising that Phil couldn’t take it. Looking back, Kim realizes that he just wasn’t into doing it and thats why. Things were changing between them and as Kim was finding more and more pleasure with cocks and anal play, Phil was finding more and more pleasure in girls.

“Let me do it again to you” Kim said

“No, I need to be going” Phil said.

Kim was incredibly disappointed. She knew Phil didn’t need to go but he had suddenly become uncomfortable. She tried to convince him but it was no use and with her still sitting there naked, Phil dressed himself and said goodbye. Kim’s cock was soft now and in the silence of the room she just sat there. The smell of the aloe filled the room, her ass was sore, and her knees had carpet burns on them. She had just done her first anal, really enjoyed it, and in under 10 minutes, it was over. She wanted to go for longer, try different positions, and spend the afternoon playing with Phil. Instead, she pulled out a few pictures from the internet that she had printed and played with herself.

What Kim didn’t know is that would be the last time she and Phil really played for over a year. They would see each other but never again in a setting like that and though they would play one more time, where Kim got the opportunity to suck on a much larger and developed cock of Phil’s, they would never again do anal. Kim would continue to play with herself and soon she worked up to larger objects, things she was finding all over, and eventually toys. And though her experience with sucking guys wasn’t over, it would be another almost 15 years before Kim worked up the courage to meet a stranger online and finally have her ass fucked again.
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3: Orgasms and Clothes, a Time of Firsts for Kim

Homeschooling was going well for Kim. She got to spend almost everyday at home, alone, for hours at a time and though she had school work to do, she really spent most of her time online. Kim really didn’t see Phil much after their meeting in which they both lost their anal virginity to each other. It wasn’t like they were avoiding each other but Phil had his own friends at school, a girlfriend, and Kim had a group of friends that were homeschooled that she was part of and a church youth group. The problem for Kim was, as they were getting older, she lost her nerve to bring up things like she had done with Phil to new people. Where it seemed normal years ago to bring it up to new people like “Nick”, it now was clearly “gay” and Kim wasn’t willing to risk people saying that about her. So, with Phil out of the picture, Kim suddenly had no one to “play” with and her daily routine was simply a solo act.

There were a lot of other changes happening. Kim was very active in the AOL chatrooms. She figured out how to login under her father’s username and change her account settings so that she had no restrictions. This not only let her access uncensored chats, it let her access websites with all sorts of content. The websites were great but she still loved talking to older men and pretending she was a girl. Reading how they were jerking off and cumming to her made her so horny. She was constantly rubbing her now noticeably growing cock with the aloe lotion, a smell that even today turns her on. She had noticed a small patch of light blonde hair above her cock, something new that also, at the time, made her more horny.

A few years before, in the shower with Phil, he had played with her past the point of squirming and causing her to shoot a stream of pee. It was embarrassing for her and they never did it again, but now, solo, Kim found a new way to do it. Using aloe or spit on her palm, she would hold her cock in one hand and rub the wet palm of her other in circles on the head of her cock. It would invoke that same feeling that Phil had done to her but now, without the embarrassment of someone there, she would go until she squirted. It was watery and nothing like the pictures she would find of cum online. There was no white to it and releasing it didn’t make her any less horny than a few seconds earlier. She was able to do it over and over again, repeating the pleasure multiple times.

Usually, Kim would go through this sitting in the computer room of the first floor of her house. She would squirt against the palm of her hand, splashing it everywhere before taking only a few seconds and doing it again. There were times she did it so often and long that the tip of her cock was sore and red. Occasionally, Kim would lay on the floor and do this, allow it to squirt up her chest and stomach. It would quickly runoff her body and onto the carpet but she would let her fingers run across it, before licking them clean. It was near the consistency of water but tasted incredibly salty, a flavor that would sit on her tongue and make her imagine she was sucking off one of the men she talked to online.

Kim still played with her ass but not nearly as often, putting everything from her fingers to sharpies in. She loved that feeling but it was nothing compared to what she felt months earlier with Phil. Paying with her ass was more of a reminder to her of that day, something that helped her imagination run and run it did. Kim found a routine for her ass play. She found a hairbrush, the handle was in-between the small size of the backscratcher and the larger size of the shower brush. Using her folding chair from pervious stories, she would unfold it, laying it out as a bed and put the head of the brush in-between the seams. Then, using the aloe as lube, she would sit on the brush handle, sliding it in and out of her ass as she bounced up and down. She missed Phil and she would moan his name, pretending it was him she was riding, occasionally leaning forward to kiss a pillow imagining they were still playing. She didn’t know when they would get a chance again, but she was going to be so good at it when they did.

Kim would try larger objects but she herself was tiny for her age (4’6” & 78lbs according a health record she found), and her pink hole was very tight. She was able to more easily put larger objects in than before, like the shower handle, but the problem was keeping it lubed. She was wrapped so tightly around it that after only a few times sliding in and out, it was dry. She enjoyed the feeling of the wider objects in her and she would put them in, stretching her out, but, if she wanted to imagine riding Phil, she needed something smaller, like the hairbrush.

One of her favorite things to do was use the bigger shower brush first, letting it stretch her out while she lay on her stomach on the floor. She would squeeze her ass closed, tightening around the handle and then release the tension. That feeling was one she loved and her cock would leak onto the blanket she was laying on, just like it had that time with Phil. She would do this for a few minutes and then jump up, pull the brush out and bend over in front of the full length mirror she had in her room. Her normally tight little hole would stay open for a second, occasionally a drop of lotion of aloe would fall out before it would quickly tighten back up. She loved seeing that and it would get her ready to ride the smaller hairbrush. She decided that if her and Phil ever played again, she would show him this.

Each of her experiences over the years had shaped her to what she was and what she would become, but one of the most important events happened that Thanksgiving.

Kim’s youth group was going to a shelter in the city to serve Thanksgiving dinner. They also had boxes of donated toys and clothes to give to the people they were going to serve. The boxes needed to be sorted so that the people could go through and pick what they wanted out of them and it was Kim’s job to sort out the clothes. Up until now, she had never really considered wearing women’s clothes. She liked to play “the girl” but she still considered herself a guy.

Kim was sorting through the boxes when she found a purple dress. For whatever reason, this dress stood out to her and it instantly made her horny. Her vivid imagination was quick to build a story with her in the dress, riding Phil and being the “girl” that she always played. It wasn’t a particularly sexy dress but it was far more sexy than anything else that she was going through. Without hesitation, she stuffed the dress into a backpack that she had brought. For the rest of the day she kept that backpack close and found herself repeatedly day dreaming about dressing up for Phil and showing him how good she had gotten at riding. She imagined for the first time making him cum and imagined it all over her dress like she had seen in so many movies.

By the time Kim got home early that evening, she had imagined herself to an incredible level of horniness and couldn’t wait to try on the dress. Even with her parents home, she rushed up to her room, locking the door and stripping down. She pulled the dress over her head and put her arms through the short sleeves. She spun around in front of the mirror. It was long on her, far from a short sexy dress, but it was a dress. Kim pulled the bottom up slightly, making it shorter before bending over in front of the mirror. She still had on underwear and she pulled it up into her ass crack, creating a makeshift thong. It was far from perfect but she found it so sexy.

Kim unfolded her chair bed and lay a green velvety blanket on it, tucking the blanket into the slit that she would stick the hairbrush in or her cock. Keeping the dress on, she slid her underwear off and bent down in front of the mirror. Her hairless pink hole wanted action but she was to horny for that. Instead, she lifted up the dress and lay on the bed, sliding her cock into the slit, soft with the velvet blanket. She spent a few minutes sliding in and out fucking the blanket, but she still wanted more. Kim reached to her nightstand and pulled down a sharpie. She put it in her mouth before pressing against her hole. This use to take a little effort for her, but it was becoming easier and it slid right in and right to the cap where the clip stopped it from going deeper.
With the dress still on and a sharpie in her ass, now Kim felt ready to fuck the velvety slit of the bed again. The sharpie stayed in place as she slid in and out. She had never played with her ass and her cock like this at the same time and she was loving it. She could lay completely down on the bed and raise her hips to fuck the slit while she reached back and moved the sharpie in and out of her hole. She could see herself in her full length mirror and the look of her in a dress doing this was bringing her closer and closer to that feeling she loved.

Suddenly, the squirting feeling was upon her. Normally she would stop to not mess up the blanket, but she couldn’t anymore and just kept going. Breathing heavy she felt her clit begin to squirt and her ass tightening around the sharpie. She closed her eyes as she continued to fuck the slit as long as she could feeling a squirt with every thrust. Finally her thrusts slowed and stopped and she lay there completely breathing heavy, her cock still in the slit and the sharpie still in her ass.
Kim’s cock softened in the slit and she pulled the sharpie from her ass.

“That felt amazing” she thought as she stood up, looked at herself with the dress on before lifting it up over her head and dropping it to the floor. She tossed the sharpie onto her bed and tugged on the green velvet blanket, pulling it from the slit of the mattress to inspect the mess she made. This time her mess was different. It had always been a watery clear liquid but this time it was thicker and there were clear white globs in it. Dressed like a girl, with a sharpie in her ass and fucking the mattress, Kim had actually cum for the first time.

Kim cleaned up her mess and hid the dress in her closet.

The Holiday forced Kim to have to wait a few days before she could play again. It was a torturous time with family staying over and her normal days alone were now filled with visitors. Finally the Thanksgiving weekend passed and Monday brought back a new normal for her.

Homeschooling started again on Monday and just like before her parents were off to work. Kim barely waited five minutes of being alone before she rushed to her room and dug the dress out of her closet. Stripping down to nothing she put the dress back on and examined herself in the mirror. She loved the feeling and look of herself dressed. Her cock quickly got hard and pushed the front of the dress out slightly. Kim felt that didn’t make her look as girly and slid on underwear to tuck it away, but her underwear wasn’t girly either.

In nothing but her new dress, Kim walked from her room and into her parents room. She found herself in her mom’s drawers, something she had really never done before. There was nothing incredible in there, but Kim pulled out a pair of burgundy panties and pulled them on. They were big on her but still fit and she rolled them and pulled them into her ass crack to make them more revealing. She pulled out a padded bra and put it on before stuffing it with socks to make it look more filled out under the dress. She climbed onto the bed in her parents room and admired herself in the mirror over the drawers. She moved around in different positions, getting a look from all angles. Kim went into the closet and pulled out knee high boots. Again, nothing extremely sexy but she had never worn heels before and slid her feet into them. They weren’t very high heels but they still lifted her heels off the ground which stuck her butt out a little further than normal. Immediately she was hooked on the feeling and again admired herself in the mirror. The dress was still too long and Kim found a belt that she used to wrap around her waist, taking up some extra of the dress and finally revealing her panty covered ass when she bent over.

Kim probably looked ridiculous to the standards she has today, but at the time, she found herself so turned on. She walked around the house for hours dressed like that. She even did some of her school work, though she was incredibly distracted. The first time she had to pee was another memorable experience. Instead of pulling the dress up and standing there, she peed like the girl she felt she was. She slid the panties down and lifted the dress; tucked her cock between her legs and sat down. She felt like a girl and loved every second of it. All morning long she did normal routine things but dressed as a girl. Something as small as sitting on a stool but having your ass on the wood felt so good to her. Finally, she couldn’t take it any longer and had to play.
Back to her room she went where she pulled the mattress down and slid the hairbrush in between the folds. She slid off the panties she was wearing and noticed a substantial wet spot were her clitty had been leaking all morning. With a quick lube of the handle, she mounted the mattress and sat back on the brush. It was becoming easier and easier to take this “toy” and within a few seconds she was bouncing up and down on it, looking at herself in the mirror as she did.

“Yes Phil, harder” She whispered, roleplaying as if someone was really there.

Kim wanted to try something bigger. She went and got the shower brush that she had used in the past. It was to tall to let her ride but still dressed, she lubed it up and lay on her back on the mattress, her legs facing the mirror. She lifted her legs revealing her wet hole and pressed the shower brushes handle into her. It was still big and she felt it stretching her out, but it didn’t hurt and she quickly popped the hold fat part of the handle inside her with nothing more than a quick gasp and moan for dramatic effect.
Now, able to watch, she begin to push and pull the brush in and out of her. If she did it slowly she could watch just how big her hole stretched before tightening back up around the narrower part. She still had to re-lube it every few minutes but it was nothing like before where she would only get it in for a few seconds. She was covering it in aloe with each time and began to fuck herself faster with it, moaning and whispering Phil’s name as she did, imagining him holding her legs up and taking her like this.
With this brush, it was much easier to imagine Phil there. It was closer to his size than the little one and the thought of that made her go even faster. She watched it in the mirror as she began to stroke her clit with the hand that she would use to re-lube the brush…which now, didn’t need to be at all as she was really getting stretched out.

Kim popped the entire handle out to look at her hole. It was wet with aloe and remained opened. She ran her fingers across it before sliding her middle and ring finger slightly in, pretending she was a girl fingering her pussy for her boyfriend. She pulled her fingers out and without warning let out an airy fart, something that had never happened while she was doing this before. She couldn’t help but laugh but quickly plugged herself back up with the handle. She closed her eyes, fucked her ass and stroked her clit.

“Yes Phil, it feels so good” she whispered to no one

Kim was nearing orgasm and slowed fucking her ass paying more attention to stroking her little clit. She pulled the handle out just far enough that the widest part was in her ass and stroked harder and harder.

“You are so big” she whispered imaging Phil fucking her while he stroked her.

That was all it took. Suddenly, for only the second time, Kim began to pump cum from her clit. It squirted up her stomach and onto her dress, sliding down onto the mattress and spraying everywhere with each stroke of her cock. The cum that ran down her hand acted like lube which nearly sent her into an immediate another orgasm, this one dry but causing her to shake uncontrollably. She let go of the brush handle and her pulsing boi-pussy tightened around it, shooting it from her ass and onto the ground. She stopped stroking and still shaking regained control over herself.

Kim looked at herself in the mirror. Her ass was just slightly opened still, shiny from the aloe and clearly used. Her cock was soft now but her cum remained on her dress and ran down the sides of her stomach to the mattress. She was still breathing heavy has she looked at the panties bunched on the floor next to her. Laying there, exposed like that, she closed her eyes and fell into a light sleep.

In a matter of a few days Kim had dressed for her first time and had a true orgasm. She had never felt as consistently horny as she was feeling now and daily she would dress up like a girl and parade around the house. She loved the feeling of panties and loved what she looked like with it all on. Though Kim still felt that her purple dress was the sexiest of the clothes she was trying on, she still needed to “borrow” other things like panties, bras, and even stockings.

It was only a month before she lucked out again and during a Christmas Community Service event a game was played to make the best wreaths out of rolled up stockings. This ended her with a few pairs of stockings at the end. They were far from sexy and looking back on it now she can see how ridiculous she looked, but she had her own stockings, something else to dress with all the time.

Unfortunately Phil was basically out of the picture now. They would see each other occasionally but wouldn’t play in any meaningful way for years. She had a new love now and it was dressing and playing with herself. The boy that loved to please his friend had become the girl with a boi-pussy and clitty; Kim.
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4: Friends Who Jerk Off Together, Stay Together

The Winter had come and gone and though Kim wasn’t seeing Phil anymore, she was actively dressing almost daily and on days when she wasn’t she was spending time online in chatrooms trading pics. She was obsessed with wearing that purple dress and had even wore the stockings out a few times, under her pants of course but the thrill was such a turn on. Kim, didn’t have a webcam or digital camera but she did manage to figure out how her dads old 8mm video recorder worked.

Kim starting taking videos of herself dressed and playing. She had no way of sharing them and had no idea how to convert them to digital but she kept a few 8mm tapes in a little safe she had in her closet, along with some of the porn she printed out. As if dressing wasn’t enough, making videos was such a turn on and she imagined she was making them for the men she talked to online. These videos survived for years a reminder to her of what a slut she was.

::: Years later Kim learned to convert them. She found herself watching her old videos while actively making new ones with a digital camera to share. Occasionally those old videos show up in the background of her albums::::

With the Spring weather Kim started to hang out with friends a bit more. Though Phil was rarely seen, she did have friends from the homeschool community and church group she was in. Jon was the one she saw most often. He had basically become her “new best friend”, replacing Phil, even though Jon and her never “Played”. There were a few times she thought about trying to bring it up to him but she was scared now and truth be told, she wasn’t that turned on by him. He was just a good friend.

Kim’s life was full of short, quick events that would eventually define her and on this Spring afternoon, this was no different. Jon was over Kim’s and as usual her parents weren’t home. However, for whatever reason Phil too came over.


:::Kim struggled for a long time to remember the full details of the day but it was just to quick:::

With Phil there, Kim felt more confident in talking about sexual things with Jon and very quickly, the discussion of porn popped up. Jon had really never seen it, at least not to the degree that Phil and Kim had. He was from a much more religious family but this, for whatever reason, he went along with. All 3 boys were in the computer room in Kim’s house. With Phil’s direction, Kim browsed sites and showed Jon pictures and movies of things he had never seen before.

This went on for sometime and obviously all three boys were horny. Phil suggested that all the boys go to different rooms in the house to masturbate. It wasn’t quite like that but it was basically “lets all split up for a little bit”.

“I have printed pictures” Kim exclaimed, “Wait here”

She ran upstairs and opened her little safe, pulling out a stack of printed porn pictures and bringing them back downstairs to the computer room. Kim spread few dozen pictures out onto the floor in front of Jon and Phil. The boys were quick to shuffle through all of it, picking their favorites separating them from the others.

“I will go to the basement” said Phil. “Jon can go up to your room and you go to the bathroom here.”

“I want to go to the basement. If someone comes home I can’t be in the bathroom with the pictures” Kim protested.

Kim had an unfinished basement but there was a couch down there and a bunch of different areas for storage.

“Fine. We can both go to the basement. I will go to the back behind the shelves and you go to the other side” Phil said to an agreeing Kim. “We will all meet back here”

With that Phil stood up and with Kim following went to the basement door. Jon took his stack of pictures and headed upstairs. Kim followed Phil downstairs but instead of going her separate way she stayed close behind him. This was her chance to show him what she had learned over the year.

Phil stopped and turned to her, readying to tell her to go her separate way but Kim didn’t wait for him to say it. She reached out and in one motion pulled his shorts and boxers to his ankles, squatting in front of him as she did. What used to be a day occurrence for them hadn’t happened the entire school year. A lot had changed in that year for Kim and now, inches in front of her face, it was a clear a lot had changed with Phil too.

Phil was much bigger than she remembered and he wasn’t even hard yet but she had waited a year for this and she wasn’t going to wait for an invite. She reached out and took his soft cock into her mouth, swallowing it all down her throat and held it there. Phil put his hands behind her head, lightly holding her in place. Kim felt his cock growing in her throat and it wasn’t long before she couldn’t hold her head there anymore. She slid it back off and admired how much he had grown.

Lengthwise, he wasn’t quite the size of Nick, but thickness, he was as big if not slightly bigger. She put him back in her mouth as he stood at the bottom of the steps of her basement. In and out she worked him, her clit hard and dripping in her pants. He was bigger than the biggest brush handle she had taken and she wasn’t sure how she was going to get him inside her, but she didn’t care, she wanted it.

“Sit on the couch” She said, pushing him lightly towards the couch.

Phil sat down and she knelt between his legs, lifting his shaft up and sucking lightly on his balls. It had been almost a year since she had tasted a cock and she was loving every second of this. It was time for what she really wanted, it was time to ride him.
Kim stood up and slid her pants down to the floor, stepping out of them and pushing Phil’s shoulder, leaning him against the back of the couch.

“I want to show you something” she said to him, stepping forward to straddle him.

Phil knew where this was headed and sat back up putting his hand out and stopping her.

“Not now, not with him here” He said

Kim stood there and tried to make an argument for it but Phil wasn’t having it. Not getting anywhere she tried to convince him to let her suck him again, but he put a stop to that too. Instead, he stood up and suggested that they go to the separate corners of the basement and do what they came here for.

Kim was incredibly disappointed and a pulled her pants up. She went upstairs without jerking off and waited for the boys to come back, which they did a few minutes later. With everyone “done”, it was now pretty awkward and Phil left shortly after. Jon and Kim went back to their normal activities though Kim just couldn’t shake the feeling of disappointment. Kim wouldn’t see Phil the rest of the Spring or Summer.

Jon was a different story though. Kim saw him a few times a week, though never the way she wanted to “see” Phil. However, Jon never looked at porn at his house, so when the urge would finally get so much he couldn’t stand it, he would suggest looking it up when he was over Kim’s and they would do what the did the first time, which was split off into different rooms and do their thing. Kim never felt an urge to follow him like she had Phil that day. In fact, months later, she was still pretty embarrassed by the whole thing. The Jon thing was fun, but there was no benefit to her really. She looked up porn without him and would still dress and play with her ass. With him there, there was none of that, it was just porn and then they go their separate ways for a few minutes.
Then, during that summer, came another one of those quick events that defined her for the rest of her life.
Ben lived within biking distance to Kim’s house. Both Jon and her knew him from Church though they had rarely hung out outside that group. For whatever reason, they hung out today and Ben came over to meet Jon and Kim and her house. Much like the earlier event, the details of how they got to this moment are gone but the 3 boys all found themselves discussing sex, porn and all the things that guys that age do. Unlike Jon before, Ben had actively been looking at porn at his house and getting involved in interesting things.

:::::::::::::::::::::::::::::
On that day, on Kim’s computer, Ben showed both Jon and Kim a Book and Films International video where a woman, with the help of another woman was being very… K9-inky. Ben showed them under the guise of “weird” and both Jon and her went along with it being so weird that they all looked up more videos, which they found on a forum website dedicated to that very thing.
Since this kind of post isn’t allowed here, I won’t go into anymore detail about this part but, it was soon after that Kim joined that forum site and became involved in the activities on there. If you are interested in the stories that involve that and Kim, send a message to receive them in private.
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Ben’s weird additions to the day weren’t the only thing they looked up however. Though Kim found herself extremely turned on by the first video he showed, they looked at much more normal things to, spending about an hour finding good pictures and printing some of them out. It wasn’t long before Ben was included in the jerk off ritual that Jon and Kim had been doing throughout the Summer. The boys broke off to separate rooms, playing with themselves to the printed pictures they had found before meeting up again to pretend everything was normal.

Ben and Kim never talked about the stuff he introduced her too that day and Ben never joined her or Jon again. Kim never forgot about that introduction and she found herself looking up more and more similar things in the coming months and finding it a great addition to the dressing fantasy that she was living out. Jon and her only jerked-off a few more times like that before, for some reason, they just stopped doing it. By the end of that Summer Kim had found herself back to being alone in her porn addiction. She didn’t see Phil anymore, Jon wasn’t interested in looking up porn, and Ben and her never hung out again. She wished that her and Phil would get together but aside from that, she didn’t really mind doing it herself. Maybe it isn’t true that friends who jerk together stay together, but that memory stays there forever.

Alone in her addiction now, Kim found herself adding hours upon hours of her self video collection, something that she would do for a few years to come. She wasn’t always dressed in them but if the collection is watched in order it becomes clear how her kinks progressed, her videography got better, and her skills improved. These 8mm videos cover about a half a decade of her life before she began to make them on a webcam and get them on a computer. They are kept close to her, a reminder to herself how she got to be this way and something she can always get off to watching.