Chapter 3
by 
Raljo
What's next?
Author Character Guide
This chapter is primarily for people who want to contribute to the Billy storyline, so that they can easily find which characters currently exist without having to search through a hundred chapters, and so that people can contribute even if they haven't read everything there is to read. These descriptions are brief and in less detail than some of the chapters' descriptions may be, for the purpose of making this guide less dense to read. Some example chapters are linked for each character, to allow you to read further about the ones which interest you. These chapters are usually either the beginning of a thread focused on that character, or otherwise relevant turning points that the character might have along different threads.
This guide may not be perfect, but I'll do my best to keep it updated and relevant. Any suggestions on things to improve are welcome!
New readers, feel free to look at this page, but please don't be overwhelmed by it! This is not in any way required knowledge, and the best way to experience the story is probably to just pick a path and start reading. Don't feel as though you have to deeply study any of this before you can start reading, almost all of the story was written and read without this guide existing at all. You don't have to do any homework before jumping in.
Authors, feel free to stick to this "canon" whenever possible, but also feel free to break from it if you feel like you want to. We're all just having fun here, and I'm not going to be strict on how you're allowed to have fun. If you make a new chapter that contradicts something here, that's totally allowed and welcomed. I won't be adding information from such chapters onto this page, and those chapters will just sort of exist as their own sort of offshoot-universe, however please don't feel limited or pressured by this! Again, we're all just having fun, and stressing over whether or not your new character will make it onto this page, or whether or not you got the characterization right, takes that fun away. This guide is to help people write chapters easier if they want to use it, not to make it harder for people to write the chapters that they want to write.
For quick use of this guide, use command+f (or ctrl+f on windows) to search the page for the character you want to learn about.
--- Billy (19 y/o school champion boxer) ---
One of the most promising young boxers in history, Billy has the potential to become the greatest of all time - something else he has, is a knockout fetish. Having never been knocked out before, or even having lost a boxing match, he decides to finally experience his first knockout in the safety of his own home by letting his sexy mother Heather (see below) defeat him. Without her knowledge, he makes her a pair of blue loaded gloves to give her an extra edge in their "match", after teaching her the basics of the sport for an hour. Then, he drops his guard, and lets her put him down. Being knocked out by his newbie mom changed their dynamic in a way he didn't predict, and he starts to lose control of his future as his mom and those gloves begin to take him down again and again.
Billy is an athletic stud, and the object of desire for many of the girls at his school. Up until the start of the story, however, his **** focus on boxing has left him a virgin - albeit a handsome, muscular, charming, and confident one. Most women would agree that his dick is perfect in size and shape, though his endurance may come into question depending on the chapter. In particular, he has a weakness for big-breasted milfs. A collection of all chapters featuring outright sex are listed at the very bottom of this guide.
Billy is somewhat arrogant, but his arrogance is backed up by his skills. He is not an inherently unkind person, though his rivalry with his little sister Anna (see below) can sometimes become a bit heated. Being repeatedly knocked out and defeated at the thing he considers himself best at simultaneously makes him extremely frustrated and extremely horny. He battles between wanting to prove their mocking insults wrong, and wanting to go and jerk off to them.
The more he's knocked out, the more easy it becomes to knock him out again... If he ever hopes to make something out of his immense boxing potential, he needs to avoid women with an unfair advantage strapped to their female fists. Unfortunately, it's not exactly up to him anymore...
Billy is academically average, though this is largely from a lack of effort. He is not dumb, he just doesn't get good grades. His elected language subject is Spanish, and his teacher is the busty Senorita Valeria (see "The Teachers of the School" below).
Primary path:
Billy loses the first mother/son boxing match ( the perfect starting point for new readers )
--- Heather (Billy's mother) ---
The single mother of two children, Billy (see above) and Anna (see below). The father of her children is intentionally never mentioned, and does not appear to have been important in any of the three's lives. Heather is financially very well off, and has a history as something of a college slut back in her younger years. A gorgeous, full-bodied goddess with large milk truck tits, Heather has matured into a lovely, well-liked member of the community - though her days of fucking the daylights out of men are long behind her.
As a mother, she is very proud of both of her children's accomplishments - but when a pair of secretly loaded gloves allow her to defeat her son at the sport he was supposed to be undefeated at, something inside her changes. One "lucky" win turns into two, and then three. Over time, the caring, compassionate milf becomes more dominant, more dismissive of Billy's talents, and more willing to indulge herself in her little power trips. After all, as far as she knows, it's her own natural talents that allow her to knock out the star athlete her son had become. She's always been successful at everything she's ever attempted, and becoming a better boxer than Billy in only a few hours is just another example of this.
The magnificent bombshell is very proud of her fantastic wins over her son, and even more proud when it seems that she is the only one who's able to defeat him at all - let alone knock him the fuck out. It makes her feels powerful, it makes her feel young, and it makes her feel fucking horny. By the end, Heather may find herself provoking Billy into fights with teases and taunts, then mocking his muscular, **** body after yet another easy win. Any chance of mercy, or feeling bad for him, is quickly eliminated by the arrogant, frustrated attitude he always has after waking up. If he can't admit that he lost fair and square, why should she feel bad about going a bit far with his defeats? He's basically asking for it. And she's just so damn good at it. God, she loves how it makes her feel.
If only Billy could somehow get a win against his mom, or steal those gloves back, maybe things could go back to normal... But Heather is having far too much fun to let that happen without a fight.
Primary paths/chapters:
Billy loses the first mother/son boxing match
Heather knocks Billy out in his own bed, for his bad attitude
Heather punishes Billy for mistreating Anna
Billy tries to come to terms with his new reality after many, MANY knockouts
Heather titfucks an **** Billy
Heather gives Billy more punishment than he can take
Heather wants more training (alternate no-Anna path)
Billy finally manages to knock Heather out
--- Anna (Billy's little sister) ---
Anna is Billy's 18-year-old younger sister, and lifelong rival. Anna is everything Billy (see above) isn't - reserved, awkward, nerdy, academically intelligent. She's always seen her big brother as someone who had it easy in life, and was frequently upset when his boxing accomplishments were put on the same level as her academic ones. The sexually-repressed model student receives top grades across every class, and frequently butts heads with Billy, despite their supportive mother Heather (see above) trying to give them both the attention they deserve.
Anna is away on a school trip to France when the story begins, and depending on the path, usually returns soon after Billy has been thoroughly KO'd by their mother - not that Anna herself knows this, of course. Though Heather may try to coax her children into having a boxing match or two, without explicitly revealing her recent victories over Billy, and Anna may inherit those secretly loaded gloves for those matches. Knocking him out with those, to her own immense surprise, is usually what kickstarts a path focused on Anna.
Should Anna ever find herself in a position of power over Billy, it would certainly go to her head, and she would indulge in this power as much as possible. A lifetime of feeling inadequate next to her popular stud athlete of a big bro would be all the motivation she needed to rub in his defeats, and maybe even indulge in a few more than he could take. With her scientific mind, if she ever found the slightest weakness in her older brother, she might even be able to turn it into a more permanent one. The boost to her confidence alone would make it all worth it - even without the added joy of seeing the big bad Billy brought to his knees by her nerdy brain and female fists. She already believes herself to be his superior, and becoming his superior even in boxing would be so much fun for her. If there was some way to turn herself into a specialized Billy-killer, or to drain his champion toughness, she would be sure to take it.
Anna has had a longtime secret crush on Billy's best friend Matthew (see below). She has a similar, albeit less romantic and more carnal, secret crush on the school's head cheerleader Sophie (see below). While Anna would want to date Matthew if only she could find the confidence to ask, she would also privately very much like to see Sophie topless - or in her most daring dreams, become the object of Sophie's desire, instead of Billy.
Anna is almost fluent in French. Her French teacher is Monsieur Dumas (see "The Teachers of the School" below).
Primary paths/chapters:
Billy's sister returns from her trip overseas
Anna knocks Billy out for the first time
Anna tests her "skills" against Matthew
Anna mocks Billy for getting knocked out by her
Anna starts weakening Billy's toughness with multiple KO's
--- Judy (Billy's aunt) ---
Heather's sister, and Billy's aunt. Her two daughers, Miranda and Rachel (see below), are listed below. Judy, like Heather (see above), is a gorgeous, goddess-bodied, financially well-off single mother. She's always admired her nephew's incredible boxing skills and accomplishments, but when she hears about how her sister was able to knock him out not once, but twice, she can't help but take those spare gloves and try him out for herself. Though Aunt Judy has a strange problem - whenever she's sober, she floods Billy with heartfelt apologies and loving care, but whenever she's drunk on red wine, the dominant boxer milf comes back out to put that little boy in his place.
Aunt Judy has no understanding of boxing whatsoever, and as such she typically has no doubt that she can dom the fuck out of Billy (see above). Her confidence can be truly staggering. Even while sober, the busty wine aunt doesn't think of her wins as flukes, or illegitimate - she just feels too bad for him to rub them in, or challenge him for another boxing match he'll surely lose.
Primary paths/chapters:
Billy's Aunt finds out about his defeats
A drunken Judy fights Billy, with surprising results
A drunken Judy has her second match with Billy, a few days later
Aunt Judy is housesitting for Heather, after repeated knockouts of Billy
--- Miranda (Billy's little cousin) ---
Miranda was first created by Stargazer234
The same age as Anna (see above), Miranda is shy and not very talkative. Both very similar and both very intelligent, Anna and Miranda have something of an academic rivalry, and the two don't get on very well. Large family dinners often have their respective mothers, Heather and Judy (see above), listing their accomplishments while the two stare each down from across the table, battling in the only quiet way they're able to. Miranda's primary subject of interest is history, though she excels at them all.
Billy (see above), on the other hand, sees Miranda as one of his favorite family members. Without the same "sibling rivalry" element that he has with Anna, Billy is able to enjoy Miranda's company without feeling threatened, because his talents lie in different fields to her own. Miranda is quietly fond of Billy, herself, as he is one of the few members of the family who will take the time to talk to her and listen to her. All the same, she does secretly harbor some quiet feelings of jealousy towards him, for the same reasons that Anna does. She feels that her academic achievements are too easily overshadowed by his boxing ones. Being the cousin of a prodigy undefeated boxing champion will do that. As much as she appreciates Billy as a person, she doesn't so much like what he represents - and she would love to take him down a peg, and show everyone that he's not as impressive as they all seem to think he is.
Miranda's relationship with her mother Judy is a good one. Judy is always looking for a possible method of getting Miranda out of her shell, and to feel more confident about herself. Who knows, maybe Judy will spot an opportunity some day.
Primary paths/chapters:
Miranda visits Billy, not knowing that Judy just defeated him
Miranda visits Billy, not knowing that his mom just ko'd him for the third time
--- Rachel (Billy's other little cousin) ---
Rachel is Miranda's polar opposite (see above), an outgoing tomboy who loves to play soccer and sometimes gets into fights with school bullies. Rachel has always idolized Billy (see above), and loves hearing stories about his boxing matches and escapades as the school club champion. Even better is when she actually gets to see one of his fights in person. In many ways, she considers her cousin to be totally unbreakable. Billy is essentially her hero. She wouldn't even be able to picture him losing a boxing match, ever, to anyone. Rachel loves it whenever he and Heather (see above) come over to visit, and as the only other athlete in the family, Billy is the relative she relates to the most.
Despite their differences, Rachel and Miranda are fairly close, though they can't relate to each other all that much and therefore don't have much to talk about.
Primary paths/chapters:
Rachel and Miranda see their mom, Judy, knock Billy out from afar
--- Coach Lucy (Billy's main coach) ---
A fit 33-year old former professional boxer, Coach Lucy knows her stuff. Her professional record was a not-too-shabby 38 wins and 6 losses, only two of which came by knockout. Though other boxers might have more "pretty" records, Coach Lucy prides herself on always having fought the best opponent available, and not a single one of her 44 professional fights were set up to pad her record.
She coaches the school boxing club alongside two men named Henry and David (see "The Teachers of the School" below), and though she is not officially the Head Coach, she is often the one in charge as she is by far the most competent of the three - perhaps even one of the most competent coaches active right now, not just because of her own boxing skills, but also her ability to teach others and spot the smallest details. She sees **** potential in Billy (see above), already believing that even at his young age there are some within the world's top 10 that he could put up a good fight against. With the right guidance, she believes he could become the greatest boxer to ever live - which is why she's pushed the school to give the boxing club more funding, more members, and more advertising. Even with all of her skills, trying her hardest, she is unable to beat Billy in a boxing match - though she is still able to give him excellent, peerless advice and training. Coach Lucy is talented, experienced, and an amazing teacher.
When she notices something is off with her club's champion Billy, she confronts him, and eventually learns how his mother has been knocking him out cold. However, she does not know that Billy has given Heather (see above) a pair of loaded gloves that allow her to win the fights, nor does she believe that Billy is simply being outskilled as Heather does. Instead, Billy convinces her that he is faking. That he began to teach his mom boxing skills, pretended to get knocked out as a joke, and then upon seeing her overjoyed reaction at her apparently rapid progress, that he continued pretending to get knocked out by her every single time they sparred. Lucy has made it her own personal quest to make Billy stop this charade, and to get Heather to realize that none of it was ever real. Except, of course, that it is all real - thanks to those unfair loaded gloves.
Primary paths/chapters:
Boxing Coach Lucy notices Billy acting strange, then sees him get ko'd by his mom for the first time
--- Matthew (Billy's best friend and fellow boxer) ---
Matthew was first created by Crushedone
Matthew is an extremely skilled boxer, though not quite as good as Billy (see above), or quite as physically large as Billy. Matthew is a close friend and favorite training partner of Billy, and is the only other member at the club who can **** the undefeated champion to pay attention during their matches. He has a slight crush on Anna (see above), Billy's younger sister, but has no idea that she feels the same way about him.
Primary paths/chapters:
Billy's mom and sister use Matthew to figure out how good they really are
--- Kristen (Anna's best friend) ---
The most popular girl in Anna's grade (see above), Kristen is an unlikely friend for the shy young nerd. Drop-dead gorgeous with curves for days, Kristen has known Anna since the first grade, and as such is well-known by both Heather and Billy (see above) as well. Anna frequently helps Kristen with her studies, since she isn't the brightest, and Anna is always welcome at Kristen's table even if the other girls there might not want her there. Like Billy, almost everyone in the school would know who Kristen is, and if she says somebody's welcome at her table, then nobody is going to oppose her. Anna's self-consciousness makes her rarely take up this opportunity, but she appreciates it nonetheless.
The busty, long-legged girl has recently cultivated a substantial following on TikTok, thanks in part to her incredibly body and thick ass, and as such she has been learning new skills to make her content on. Gymnastics, painting, all sorts of things. A visit to Anna's house might inspire her to ask for Billy's help to make a series of boxing TikToks... The shocking result of which may just skyrocket her online career.
Primary paths/chapters:
--- Sophie (Head Cheerleader) ---
Sophie is a rich, busty, beautiful, blonde, and a very talented cheerleader. She's a bit of a nympho, frequently fucking the male students of the school, and rumors are that Sophie give bare-breasted titfucks in the school bathroom for cash. The ones she's taken to bed, no matter how athletic they might have been to begin with, are frequently put out of commission for days by her overpowering sex drive and expert-level pussy. Her mother is Bianca (see "The Moms of the School" below), and she has a twin sister named Amelia (see below).
Sophie could have any boy in the school that she wanted as her boyfriend, but her sights are firmly set on the unattainable Billy (see above). He was the one boy that Sophie actually wanted to date, as well as fuck. Her obsession with Billy is part of what fuels her sexual escapades, trying to fill up her desire for him with as many other dicks as it takes. Should the two ever actually meet in the bed, it is impossible to say whether Sophie will finally be sated by his amazing, prodigal, champion dick, or if she would overwhelm and slay the champion with as much ease as she did his classmates.
Though she has not yet approached Billy directly about her desires, she has considered many possible methods. Perhaps she should join his boxing club? Or perhaps she could arrange for his younger sister Anna (see above) to set the meeting up for her? Regardless, even until that day when they might end up together, Sophie will be thinking fondly of Billy and defending his honor any time it comes into question.
Primary paths/chapters:
Anna is interrupted by a group of cheerleaders
--- Selena ---
Selena is the daughter of Karen (see "The Moms of the School" below). She is somewhat socially inept, due to her mother's helicopter parenting and the lack of friends that came to her because of it - no child was "good enough" for Karen's perfect little girl. As such, Selena is a spoiled and entitled, but socially awkward young girl who is always excited to have company.
When Billy (see above) is **** to teach Selena how to box, under threat of Karen releasing pictures of him knocked out on the floor, Selena develops something of a little crush on Billy. Despite being 19, it's the first time she's ever had any real one-on-one time with a boy. Her warped, isolated princess lifestyle perspective manifests this crush in a very unique way. Selena becomes obsessed with the idea of knocking him out, and specifically of hearing him snore. She calls Billy "sensei".
Primary paths/chapters:
--- Amelia ---
Amelia is the busty and gorgeous blonde truant who, despite being a member of the boxing club, never bothers to show up. She’s very popular, but her popularity is slightly limited by her not caring very much about it - making her far more liked than most, but not quite as popular as her twin sister Sophie, the Head Cheerleader (see above).
She never cared much for the boxing club to begin with, but after making a mistake that got her accidentally knocked out by Billy (see above), she was too humiliated to even pretend to care. She’ll occasionally show up to the club, but most of the time she’ll skip it to hang out with her friends - and even when she does show up, she isn’t much of a participant.
Amelia isn’t the sort to go around telling her family she loves them and taking them into big hugs, which makes her an anomaly with a sister like Sophie and a mother like Bianca (see "The Moms of the School" below), but she still loves them both very much, and participates in family conversations.
One such family conversation has Amelia hear that Billy just got knocked out by her own mother Bianca - first by her fists, then by her tits - and while Amelia doesn’t believe the story, thinking that her bimboish mom must have misunderstood something, she still think it’s a pretty fucking hilarious thought. Amelia decides to start spreading the rumor of his KO loss to Bianca around the school. After all, who could it hurt? Besides Billy, of course. But what was he going to do about it? Confront her head-on? Well, actually…
Amelia learns about Billy’s humiliation
--- The Moms of the School ---
When Billy (see above) agrees to help his Coach Lucy (see above) out by running a boxing seminar for her, to show some concerned mothers of the school that the club is a safe and rewarding place for their daughters to join, things go poorly for him. But depending on the path, the avatar of his downfall may take one of many forms.
Bianca: a bubbly, cheerful, ditzy bimbo with an incredibly impressive bust. Her twin daughters are Sophie, the Head Cheerleader (see above) and Amelia (see above). Though technically Sophie, as head cheerleader, is already in one sports club, her interest in Billy has led to both her and her mother attending the respective parent/student boxing club seminars. Bianca is a kind and warm woman, but her ditziness comes too with a degree of cluelessness that can lead to unpredictable outcomes.
Karen: a snooty, obnoxious, busty bitch who hates being told what to do. Karen is not happy about being **** to attend this seminar, and even less happy that her perfect daughter Selena (see above) now has to join a sport. She is looking for any opportunity she has to undermine or destabilize the school's authority - and at this seminar, that means undermining Billy. Outside of this event, Karen is especially envious of Billy's mother Heather (see above), as she is loved by all and seems to be living the perfect life, while Karen is largely disliked by those around her thanks to her bitchy attitude - though few will say it to her face.
Rae: a 39-year-old former pro boxer who retired to focus on motherhood at the young age of 28, Rae has kept herself in excellent shape, and most of her boxing skills are still sharp. She is somewhat bitter about never having become a champion, despite floating around the top of her weight class' rankings for most of her career. Never quite being able to get the belt has left her feeling like she was never adequately celebrated for her skills. For years, she has also been unable to shake the shocking realization she had early in her training days, when she discovered that even the best professional female boxer seems to be unable to do anything against even an average male amateur. When a groggy, post-KO Billy starts making little mistakes in teaching his boxing seminar, Rae steps up, and begins to see it as an opportunity to not only prove that she hasn't lost her skills, but also finally get over that mental block of never being able to beat a man, by beating this young athletic prodigy - and for the first time, defeating a champion. Surely she would be celebrated then. After all, so many moms of the school will be watching.
Tanya: a sexy helicopter mom, Tanya is holding a secret vendetta against Billy after her knocked out her perfect, sweet son Sam in a boxing match. After a few weeks stewing over the “injustice”, reading the school website praising Billy as a skilful prodigy, she’s had enough. She attends the seminar with a pair of homemade Loaded Gloves, to avenge her precious Sammy.
--- The Girls of the School ---
When Billy (see above) agrees to help his Coach Lucy out (see above) by running a boxing seminar for her to introduce some prospect club members to the world of boxing, things go poorly for him. Since the school has introduced a new rule that all students must participate in a sport, these girls range from athletic tomboys and adventurous girls actually interested in boxing, to shy nerds and popular pretty princesses who are only there because they have to be.
Jade: (I have not published this branch quite yet, and will fill in the description once I do. No spoilers!)
--- The Teachers of the School ---
Aside from Billy's main coach Lucy (listed above), the school has many other faculty members who have come up across the stories.
Monsieur Dumas: Anna's French teacher, in his early forties.
Monsieur Dumas was first created by mlg3789
Senorita Valeria: Billy's Spanish teacher. She finds it annoying how little he pays attention in class, and how little respect he seems to have for it. Busty and beautiful, with mocha skin and long, silky black hair.
Coach David: an arrogant musclehead, once a great boxer, but held back as a coach by his impatience and anger issues.
Coach Henry: enthusiastic, but inexperienced, having never been a professional boxer himself.
Senorita Valeria breast smothers Billy ****
Anna is caught on her phone in Dumas' class
--- Other Cheerleaders of the School ---
Sally and Daisy were first created by peep
Besides Sophie, the Head Cheerleader (see above), there are plenty of other cheerleaders at Billy's school. Being the popular, attractive, muscular boy that he is, many of them have just as much of a crush on him as their queen bee does.
Sally: a surprisingly timid girl for a cheerleader, Sally once thought that she could become a boxer, only to have her dreams stopped short by a one-punch knockout from Billy himself (see above). She's not too bright, not too confident, and a bit of a follower, but the right opportunity could see her earn some surprising achievements.
Daisy: something of a Billy fangirl, Daisy is your typical busty bimbo shortstack mean girl. Curvy and thick, she's the sure runner-up to Head Cheerleader just behind Sophie. Her closest friend is Sally (see directly above), but Daisy isn't very nice to her, and generally uses her more as an assistant sheep than a close equal. She likes the power and control of it. Her ultimate goal, similar to Sophie (see above), is to seduce Billy (see above) - the one man she couldn't conquer. Her desire for Billy is powered by nothing other than the fact he seems unobtainable, though of course his impressive physique and massive popularity help as well. Unlike Sophie, however, Daisy has repeatedly tried to seduce him already, without any success. While Billy may be interested in dating Sophie should she ever make her intentions clear, Billy isn't willing to waste time on someone like Daisy. She's too needy, high-maintenance, and mean. But under the right circumstances, Daisy might just find herself with the legendary Billy under her thumb at last, taking the unobtainable boy for herself right out from under Sophie's nose - the ultimate victory for this bitchy, busty, controlling cheerleader mean girl.
A weakened Billy foolishly teases Sally
Daisy discovers Billy and Sally in the aftermath
Sally knocks Billy out, and gives his sleeping body a standing thighjob
--- Other Boxers of the School ---
There are plenty of members of Billy’s Boxing club, both past and present, who may have a run in with the resident champion.
Carly: A prideful feminist, Carly joined the boxing club to prove that girls could fight just as well as boys. Suffering defeat after dominant defeat made her give up that idea. Now she trains kickboxing at a different gym, but occasionally Carly still pokes her head into Billy’s home turf.
Carly was first created by mlg3789
Carly does better than she should while sparring Billy
Sam: A male member of the boxing club who challenged Billy to a fight a few weeks before the story begins, in which he was knocked out by the champion. His mother is Tanya (see “The Moms of the School” above), and while Sam doesn’t mind the bruised ego and public KO, his mother may never forgive Billy.
--- Chapters of Outright Sex ---
Though not a character, it may be useful for some people to have a list of these chapters for the sake of keeping Billy consistent, so here they are. There are plenty of chapters with things like titfucks, facefucks, handjobs, blowjobs or masturbation, but these are the chapters in which Billy directly loses his virginity, or otherwise fucks/gets fucked by a woman.
Billy’s dick knocks his mom out
