*This is the “first” story of Charlotte’s journey.*
*This is a remake of “Charlotte’s Bet” by “toocold”. If you want to check out the original version, you can discover it on Literotica. This version will reuse parts of the original story. I added a lot of my own ideas, with some smaller edits here and there.*
Charlotte Fairfield would admit, in hindsight, that it had been a reckless bet to make, especially when her friends started to escalate the forfeits. She couldn’t even use the excuse that she was drunk as she was driving home from the party so she hadn’t touched a drop. She’d all the time been pleased with herself – a confident, gorgeous 19-year-old girl with soft, natural blonde hair falling around her shoulders and a slim, gently curved body with long, slender legs, a peachy bottom, and lovely pert 34C breasts. So when she’d declared that she could make any guy at the party cum within five minutes thanks to her blow job skills, she had meant it, even though it had been light-hearted.
What Charlotte did not know was that Jane had other plans. Unaware that Jane did not like her all that much, the blonde girl made her boastful claims, which had brought her into the situation she was now in.
First, Jane called her on her claim, and then it started to escalate. So, here she was, in her friend’s bedroom, waiting for the first of the 12 men, all former classmates, who had been at the party. The deal was simple: One guy would come into the room, one every five minutes. She’d suck them off until they came. Except, if a guy lasted longer than five minutes, the next one would not wait, and so would be allowed to fuck her pussy. And if both those guys lasted another five minutes, the next man in would be up her ass – but Charlotte believed no man could last ten minutes with her beautiful lips around his cock. She laughed off suggestions that she’d discover herself with no spare orifice and told Jane that she would do anything they decided, as this would never happen.
With this once-in-a-lifetime opportunity to humiliate her ‘friend’, Jane had little difficulty convincing the guys at the party to participate. After all, they knew who Charlotte was. Back in the day, Charlotte and Jane had been part of the cheerleading squad of their college, and to get a blowjob from one of them, or maybe even something better made it an easy decision.
Especially when Jane began to tell them of her plan to guarantee a win.
Fitting the theme of ‘school reunion’, Charlotte wore white knee-high socks, a blue pleated skirt, and a white blouse with her old college tie. Sitting on the bed, waiting for the first lucky guy to enter, the young blonde decided to unbutton her blouse. Considering that in the next 60 minutes, she would have to make twelve guys blast their cum down her throat, there was no point in keeping her modesty. Boobs out, pink nipples hard, Charlotte went to her knees, as the first guy entered the room.
## 10:00 pm
Alex was surprised. Seeing his former classmate not only showing off her tits to him but also ready to blow his cock meant that what Jane had told her was true. He got over his shock quite fast, pulling out his rapidly hardening cock, as he approached the former cheerleader who stuck out her tongue, ready to make him cum. In the past, he had heard stories of the cheerleader blowing the basketball and football players, and when she reached out, positioning his hands on her tits as her lips kissed his shaft, Alex began to believe.
Yes, his cute little former classmate was definitely able to make him cum in less than five minutes. Squeezing her tits, something he had wanted to do for a long time, Alex felt how Charlotte took the entirety of his cock into her mouth while using her tongue to play with his balls.
Alex was mindful of the fact that all the guys had the duty to hang on as long as they could, but he fancied her for years and, as he looked down at the lovely teenager in her ill-fitting college uniform, he lost himself in the pleasure and the sensations her sweet mouth was giving him. After just under four minutes, he stopped squeezing her tits long enough to grab her head and twist his fingers in her blonde hair as he came, his prick twitching in her mouth as he fired his spunk. Charlotte twisted her head so that it didn’t go straight down her throat, collecting his salty jizz in her mouth, then swallowing it all down as he pulled out of her. Sitting back on her haunches, she smiled up at him, wickedly.
If she had to be totally honest, Charlotte liked his cock, and the taste of his cum.
## 10:05 pm
Charlotte had thirty seconds to prepare herself before Bob walked in, grinning like a Cheshire cat and already pulling his cock out of his jeans. Without standing on ceremony, he pushed it into her mouth and started to face-fuck her quite roughly. She’d been expecting that – she’d blown him before – and as Charlotte sucked him she played with his balls. Three minutes later, Bob cried out as her mouth again filled with sperm, and again, Charlotte swallowed like a good little cheerleader.
A stupid bet back in the day had given him the opportunity to face-fuck her once, and now a stupid bet had given him a second chance. Both times, she swallowed.
## 10:10 pm
Charlotte was surprised when Chris was next – he was Jane’s boyfriend and she had not expected Jane to send him in. Still, a bet was a bet, and as she took his dick in her mouth, she noticed that something was different. It took longer than ordinary to make Chris fully hard, and not only that, his cock had been quite literally soft when she began to take him in.
Charlotte had to use all her skills, working her tongue and lips on his shaft, playing with his balls, taking him all the way to the back of her mouth, and even taking his balls in. All the while, Chris held her head, grinning at the former cheerleader. Minute after minute passed, and the blonde girl panicked. Looking up at him, her big blue eyes full of worry, she figured that Jane must have blown him before he entered the room. Sure, it wasn’t against the rules, but it was still dirty.
Three minutes in, Chris finally began to get hard, and just as Charlotte started to gain her confidence back, knowing that her blowjob skills were the best in town, the door was slammed open.
## 10:13 pm
“Eh? H-hello?” Quickly pulling her head back, and starting to wank Chris, panic and confusion filled Charlotte’s mind, as she saw the next grinning classmate enter the room, already with his pants down. She had set up her phone to ring every five minutes, so she knew there was no reason for another guy with a hard cock to present himself before her. “Uhm, Daniel?”
Without responding, Dan positioned himself right next to Chris, jacking off while aiming his cock at the young girl. Just as she was trying to process what was happening to her, Daniel blasted several strands of cum straight on Charlotte’s bewildered face, as she continued to wank Chris off. Some smaller spurts and droplets covered her blouse and tie, and as Dan’s cum trickled down her face, nasty and creamy, Charlotte understood their plan. Looking shameful at the two guys, she continued to suck Chris off.
She had to make them cum. A bet was a bet, and bailing out was not an option.
Dan, slightly panting after his cumshot, decided to stay in the room, watching his former classmate he had just used as a cum dump deepthroating Chris’ cock. After all, his own turn was in just under two minutes.
## 10:15 pm
“Ohh, I see! So cute, little Charlotte couldn’t make my boyfriend cum in time?”
The timer rang, and instead of Dan, who was already there, Jane stepped into the room. With a deeply satisfied grin on her face, she watched as her blonde friend sucked Chris’ cock, as deep and as fast as she could.
“You know, darling… I thought you would do better. Guess you are not *that much* of a slut.”
If not for the cock in her mouth, Charlotte would have spat some obscenity at her, maybe even some cum. The blonde girl now knew that Jane set this up, and there was no point in blaming the guys. Of course, they would participate in this debauchery, ravaging the former high college cheerleader they all knew and desired.
Walking up to Chris and giving him a little kiss, Jane smiled as she watched Charlotte’s cum covered face, bobbing back and forth on her boyfriend’s member. “Darling, I am gonna help you out. You don’t mind, right?” Not caring about a response, she winked at Dan, who was already hard again. Stepping behind Charlotte, who was still delivering the best blowjob that she could offer, Jane put one hand on the blonde girl’s back, pushing her down to all fours.
Still continuing to suck Chris off, Charlotte felt how her skirt and panties were pulled down by Jane’s gentle hands, giving Daniel access to his prize. Now, after blasting the lovely teen’s face with a load of thick semen, Dan could raw-dog Charlotte’s sweet tight pussy. He had wanted to fuck her ever since the first time he saw her cheer in a college uniform, and after he had his fun with her, he would pump his cum straight into her womb. But before Charlotte could feel his cock enter her pussy, she had to feel a little slap on her bare ass, and hear Jane’s mocking voice.
”Wow, darling! You look good! You’re even shaved!”
## 10:20 pm
“Oh, Sweety! The timer is ringing!”
Charlotte had closed her eyes. Just seconds after Chris pumped his seed right into her mouth, did Eric enter the bedroom. If not for the muffler she had for the last few minutes, small quiet moans would have escaped the teenager’s lips, as Dan slowly and methodically pumped into her, pushing the girl forward every time he went balls deep into her pussy. Unfortunately, Dan was good at what he was doing, grabbing and massaging her ass cheeks and fucking her in long strokes. It made it difficult to concentrate.
Even worse, Jane had decided to stay in the room to ‘make sure that no cheating would occur’. Her instructions to the boys were clear, and Charlotte could attest to that. With Chris’ cumshot still in her mouth, and the timer ringing, Eric decided to unleash his load all over Charlotte’s face. The sensation of a mouthful of cum, two loads splattered all over her face, and a guy pounding her pussy made the young girl dizzy.
Eyes still closed, Charlotte could hear Jane giggle. Gulping down Chris’ cum, she slowly opened her eyes, mindful of the cum that had just been dumped across her face. What she expected to see was a cock pointing at her face, but instead-
“Hey, you don’t mind that Frank is here, right? You know…” Jane grinned. “He just gotta shoot his load, before he gets his chance. And seeing you, Sweety, makes it that much easier!”
There were two. Eric, who had just cum, quickly stepped up to her, pushing his limp cock into her mouth, while Frank jacked off. Charlotte closed her eyes again. One little spark of hope appeared in her mind. With Dan continuing to pound her pussy relentlessly, her whole body shook from his treatment. There was a chance, at the very least, that she could orgasm herself. Right now, as she was on all fours on the floor, only wearing her white blouse and her knee-high socks, waiting for seven more guys to have their way with her, getting off would be the only good thing that could happen to her in this predicament.
“Oh, oh, Sweety!”
And of course, Jane had to chime in. Not even a minute passed, licking and sucking Eric’s member when Frank, who was busy jacking off to his former classmate, blasted his load onto her face. Charlotte’s left eye was sealed shut by a layer of cum.
If only the guys would cum that fast when they were fucking her.
## 10:25 pm
Jane and Frank both smirked at the young girl.
Charlotte couldn’t believe it. Dan had been fucking the blonde teenager for almost ten minutes, and he showed no signs of stopping. Dropping a load seemed to give him unending stamina, even when pounding the hottest cheerleader in town. And now, he would not only get the chance to fuck the girl of his dreams. Now, she would be fucking him.
“Oh wow, Charlotte! It’s halftime! Your knees must hurt, right?”
With Dan and Eric pulling out, Jane was willing to make sure that the blonde girl was in a proper position to get fucked by three classmates at once. After getting rid of the rest of Charlotte’s clothes, the white cum-drenched blouse, the skirt and panties that were still around her knees, and even her socks, Jane led her to the bed, before asking Dan to lie down. At that point, Charlotte stopped to put up any resistance, and if Jane wanted her to be naked, she might as well be. The guys surely liked it.
Helping Charlotte position herself on top of Dan’s cock, Jane pushed her down onto him, making sure that her tits were in range for him to fondle. Eric pushed his cock back into her mouth, while Frank finally got the chance to deflower Charlotte’s ass.
The blonde girl braced herself. This was the result of making stupid bets, and even though she had done her fair distribute of bets and dares, this was the first time she would be getting assfucked for it. And the cock stretching out her pussy would not make her first time easier.
Spitting on her asshole, Frank positioned his cockhead in front of her tight entrance. Dan and Eric stopped moving, while Charlotte held her breath. She could feel, how Frank pressed his cock against her asshole, the sensation of his cockhead slowly entering her most private area, and it burned. It felt insanely tight, together with Dan’s cock in her pussy. Charlotte was still unable to say anything, as Eric, thoughtful as he was, had decided to hold still as deep inside of her throat as he could. Her lips were kissing his balls, while Frank continued to push into her virgin rectum.
*SLAP*
Small little tears appeared on her face, as she felt a burning sensation on her right ass cheek. And she knew it wasn’t Frank. She could feel his hands holding onto her.
“Come on, Frank!” Jane gently fondled Charlotte’s ass. “Be a bit more nice to her, yeah? She only got like 3 more minutes, okay?” Another slap, this time less loud. “Don’t worry. Look! I know her. She loves it.”
Not needing any more encouragement, Frank decided to go all in. A muffled yelp escaped Charlotte’s muffled mouth, as her ass finally received a proper fucking.
The blonde girl promised herself, to never make another bet with Jane ever again.
## 10:28 pm
Two minutes before his timer rang, Garry entered the bedroom. He almost couldn’t recognize the young girl. Surrounded by guys below, behind, and in front of the nude blonde, he had to watch how she was getting destroyed by three cocks in all of her holes. Half of her blushing face was drenched in white sticky jizz, her whole body was drenched in sweat, and the desperate moans she made, were sounds he had never heard before. When he blasted his load all across her exposed back, Charlotte didn’t even care. She bounced on Dan’s cock like her life depended on it, while Frank and Eric fucked her without restraint, causing her whole body to shake.
This was better than anything he had ever imagined. Better than any wet dream he had ever had. This lovely teenager in front of him was experiencing the result of letting a dozen teenage boys do what they all the time wanted to her. Jane had given them the opportunity, and they were reaping the rewards.
“Oh-Oh GOD!”
Four minutes of triple penetration had passed, and Charlotte was done. A cock balls deep in her formerly virgin ass, another cock inside her pussy, about to push a load into her teenage womb, and a third one blocking her airway. The poor blonde could not handle it, and with small tears escaping her eyes, she let out a muffled scream.
Her former classmates, Dan, Eric, Frank, Garry, and of course Jane, were all able to witness, how Charlotte moaned out her lust. Despite the cock muffler, they all could hear, how the young cheerleader came. Dan felt the inside of her pussy convulsing around his member, while Frank felt a similar sensation with her ass. Charlotte’s body shook, as she felt the most intense orgasm she had ever felt in her young life. An orgasm that, prolonged by the cocks fucking her brains out, was crowned by the sensation of Dan and Frank blasting their loads into their cumming classmate.
It was the first time Charlotte had to feel how her rectum was pumped full with thick creamy semen, and it was also the first time someone pushed their load straight into her pussy. Done with cumming, Charlotte would have sighed if she could.
At least, they both came before the timer rang.
## 10:30 pm
Riding Garry like a good little cheerleader, Charlotte felt almost refreshed. Sure, the sensation of cum dripping out of her asshole, or the fact that she had to ride another cock right after cumming was far from ideal, but she could work with it. Garry was the seventh guy out of twelve.
She was almost able to forget, why she even got into this situation. Well, neither Jane, who was still in the room nor the smell and feel of cum helped her with that. At this point, she didn’t even pay attention if a guy entered the room, or even if they blasted another load on her. She had more essential duties. Even if Henry shot his load all across her tits.
## 10:35 pm
Unfortunately, Charlotte was unable to make the guy in her mouth, or the guy she was riding cum. Henry was big, but his passage into her most private area was lubed, even if it was just a load of cum. Charlotte felt like a ragdoll by now, as the second guy in one hour starting to stretch her asshole. And now, she was getting triple penetrated again. The wondered of giving up popped up in her mind, as she didn’t know how much she could take anymore.
While Henry jackhammered her ass, the young girl tried to evaluate what would be worse. As another orgasm slowly approached, Charlotte tried to make a choice between getting fucked by a dozen guys in an hour or losing a bet to Jane. With her entire body shaking, Charlotte closed her eyes. Jane, after all, was-
“Soo… Sweety? I was just thinking right now, what I should do with you after this is over.” Jane was inches away from Charlotte’s cum covered face. “You know… It’s looking kinda bad for you, don’t you think?”
The boys continued pushing into her, and Charlotte, half-heartedly, tried to ride Garry. Opening one eye, the one not covered by cum, Charlotte looked at Jane’s grinning face.
“You see… Perhaps I just let you go home the way you are. After the guys are all done with you, of course. Your clothes, I will safekeep them for you.”
Charlotte’s eye became as big as a saucer. This was bad. But considering the fact that soon, a second guy was probably about to cum in her ass, she-
“Maybe, I can ask the boys if they want a second round with you, right? Might as well let them have you for the rest of the night.”
The incoming orgasm made it difficult. Too difficult. With the way Charlotte was feeling right now, the second idea was definitely preferable to the first one. She was getting fucked anyway, and she got to keep her clothes. The prospect of orgasming multiple times this evening seemed quite enticing.
“Or… What about doing the same thing as today, but next time I bring a few more guys with me? Maybe our local football team? I am sure many of them there know you.”
Charlotte started to pick up speed. Bouncing faster and faster on Garry’s cock, she realized that this was going in a direction she would never be able to recover from.
“We could also combine the ideas I have had all into one. Yes! That would be perfect!”
With her cum covered tits shaking up and down, the blonde teenager knew that she had to do it. Her mouth, as skilled as she was, was not enough to make the boys cum fast enough. Garry had the chance to experience how a cheerleader was riding his cock with all she got, but he needed more to cum. Sure, this lovely young girl sitting on his member, bouncing up and down like a good little slut, was mind-blowingly hot but-
“We could keep you here until tomorrow, and call the football team, and then after the boys are done with you, let you go home. Doesn’t that sound great, Charlotte?”
The only response was a loud, desperate moan. Jane and the boys had misunderstood. Charlotte wasn’t trying to make the guys cum.
“MHHHHMM!”
Charlotte couldn’t believe it. She couldn’t believe how ruthless Jane could be to her, sending guy after guy into the room, all to watch how Charlotte got gangbanged into submission. The eagerness of all the guys surrounding and defiling her, the copious amounts of semen pumped into her body and drenching her face and tits, the sweat, the grunts, and her own moans, overloaded her brain. She knew all of them, just as they knew her, and the wondered that all the boys she knew from high college had it in them to fuck her brains out without any restraint made it all the more outrageous.
The way they all grinned, groaned, and panted, as they fucked her with all their might, fondled her tits, and even played with her hair when she got facefucked, all made it clear how much Charlotte was the focus of all their thoughts.
Henry, Garry, and even Eric all came. Their combined efforts had broken the young girl, and they could feel it with their cocks deep inside of her. Her orgasmic spasms, her muffled screams, and gasps, and the way she wiggled her ass as she came for the second time pushed all of them over the edge.
Almost drowning in Eric’s cum, the poor blonde felt how another load filled her teenage womb, mixing with the spunk already inside her. When Henry pulled his cock out of her ass, cum flooded out of her gaping asshole. Her rectum was filled with thick nasty cream, her womb was now filled to the brim with burning hot semen, and all Charlotte could taste was male lust.
Charlotte blacked out for a few seconds. Her plan had worked. A girl in the throes of orgasm, as the result of male hunger and desire for her, was the most effective way to make her classmates cum. Henry, even though he already shot a load, only got a chance to fuck her ass for barely four minutes, before he violently came, filling up her rectum.
Now, only Jane and Charlotte were in the room.
It was hard to tell who had won right now. On the one hand, Charlotte only had to please four more guys. On the other, Jane just witnessed what an insane slut Charlotte could be.
The door opened, and Ian entered the room. The poor young girl, the prettiest girl he knew, now with cum pouring out of all three of her tight holes, and panting like she had run a marathon, made him cum almost immediately.
## 10:40 pm
The newly added layer of fresh cum covered her other eye. With the timer ringing, Charlotte opened her mouth, presenting herself to Ian, who had climbed onto the bed. Since his cumshot had made him limp, Ian decided to let the young girl do the work. Despite, or rather because of her messy state, the nude blonde looked beautiful to him, and he had no reason to hurry up.
With slow methodical movements, Charlotte tried her best to make him hard. But the teenager was spent. Seven guys had had their way with her, and the two orgasms Charlotte endured took almost everything from her. Now, she couldn’t even see, and she only knew that she was blowing Ian because of his grunts.
Somewhere in the background, Charlotte could hear Jane whisper. The young blonde grinned, despite the cock in her mouth. Her performance must have outdone even Jane’s wildest expectations. The young girl’s thoughts were interrupted by the sensation of another cumshots blasted all across her face, with almost half of it hitting her hair.
She had no idea whose cum it was.
## 10:45 pm
As she heard the door close again, she knew it was too late. With Ian’s dick still thrusting in her face, she felt Joe sink to the hilt in her slimy cunt, his passage made easy by the sperm of his friends. Charlotte was lost, now, feeling like a rag doll as the third man in the last half an hour energetically fucked her pussy – at least he didn’t seem to be trying to hang on. But then he slowed, settling to a hard, thrusting but slow rhythm, his every thrust shoving her throat onto Ian’s cock, making her choke.
As she got spitroasted again, Charlotte slowly moved her hand towards her clit. If she truly wanted to win, another orgasm was needed. She didn’t even recognize the fact, that the next guy in the gauntlet had just jizzed on her face. In fact, it felt like multiple loads, but maybe they were just cumming a lot.
## 10:50 pm
After quickly switching positions, Charlotte groaned deep in her throat and small little tears rolled down her face as Karl forced his dick up her bottom, leaving her once again with three cocks in her at the same time. His passage was made easier thanks to the ass-fucking she’d already received, but she still could not believe what was happening. She also couldn’t believe that Ian was still in her mouth and hadn’t yet come. Once again, she was out of holes and there was still one classmate to go.
Charlotte couldn’t masturbate. She just couldn’t. Hanging on for her dear life, just trying to get enough oxygen into her lungs was all she could manage. The poor girl began to see stars, and even though she wasn’t able to do anything apart from getting fucked, her next orgasm was just on the horizon.
## 10:55 pm
With Jane also climbing on the bed, Charlotte had to listen to what she said, unable to turn away due to the three guys currently fulfilling their part of the bet.
“So, darling… You hear that?” The timer on Charlotte’s phone rang. “It’s the sound of my victory.”
Charlotte barely heard her, but she could not react as she was quite busy with her current situation. Listening to Jane’s mocking voice, while she was getting gangbanged wasn’t exactly a good time.
“Remember? You said you would do whatever I wanted if you lost. But for now – Just try to enjoy yourself. It’s the best you can get.”
Cumming, while Jane talked to her, was not what Charlotte expected to happen. Now that the bet was lost, the three men in Charlotte had no need to temper their passions, and all started to fuck her in earnest, roughly driving in and out of her until, one after another, they emptied themselves in her, leaving her mouth, pussy, and ass full of spunk. Once they’d left her, Charlotte simply collapsed back onto the bed, physically and mentally exhausted, tears of shame running over her cum-coated cheeks, her sore pussy and ass also leaking from half-a-dozen loads of cum. She could not believe how cruel Jane had turned out to be. Jane had let loose a horde of horny, teenage boys, who used her young exposed body, first to jerk off, then to fuck all sanity out of her.
The guys only did what they were allowed to do. What Charlotte and Jane allowed them to do.
And now, Charlotte had to pay for it.
“You’re right, Lewis. I guess she failed in the bet. That means that you don’t get a go, honey. Or maybe… Maybe you will? Don’t worry – Charlotte said we could have whatever forfeit we wanted, so you’ll definitely get your turn one way or another. But I gotta be honest: She did incredibly well. If not for my little idea, Charlotte would still have a virgin ass!”
*Thank you for reading! If you want to know how the forfeit turned out, you can take a look at my user account!*
NSFW: yes
Had to repost because of “unstated or dubious age”. I hope they were talking about the title since the very first paragraph of the story tells us about Charlotte’s age. And as they are celebrating a school reunion party, it’s also hopefully clear that they’re not kids.