Something along the lines where somebody like a friend, cousin, mom's friends son... comes over and stays at the house for a longer period of time. Like a summer vacation or his parents go to a foreign country to work for a while. The son and this friend/cousin get along great as he is preferably his age or younger. Well what the son doesn't know is that this friend has a huge crush on his mom and wants to do her. The son is oblivious to all of their flirting and doesn't notice anything going on around the house. For instance during one night this friend goes to his moms room because he is scared of thunder. Or when his mom says he needs to go to the store because the friend doesn't feel good. Or when he comes come and he hears voices from his moms room and goes to check and his mom opens the door in just her night gown (silk, see through), and says the friend needed to lie down for a bit. The son just accepts it as he doesn't think anything will happen between them. Well thing keep progressing and the mom starts changing too. At first at the beginning she would dress like a proper mom, but as thing go this friends way she would wear less and less clothes. The dad should also be in the picture somehow. Perhaps as a traveling director or something which keeps him out of the house for longer periods of time. As the dad would also be keen on this friend and would tell his son to be more like him. Anyway this friend and mom would get bolder and bolder and would start having sex all over the house as they would be turned on not by humiliating the son but by the chance of being caught by him. The friend would keep pushing the boundaries until one day they would get caught. The son would freak out but mom and friend would have a plan. Perhaps the son did something bad, like he broke something or stole something. So they blackmail him to keep quiet to his dad unless he wants to go to military school or something. From then on mom and friend start having sex in front of him even though mom doesn't want it at first but grows to like the freedom of doing all over the house at any time. When dad comes home the son has to run interference so that they can fuck.  It ends with the friend/cousin going back home while the son wows to do the same to him one day.

I like to see a story that doesn't start out as a "bullying" story but slowly turns into one.

A happily married couple with a son and a daughter.  The mother is at a school event of some sort for her son and ends up meeting and being charmed by a student in the school that's a year or two older than the son.  The son and this student don't have any sort of preexisting relationship.  They're aware of each other but not in the same circles.  Ultimately the mother runs into this student a few more times and ends up being seduced.

It turns into a bit of a cuckold story as she's fucking her new "boyfriend" behind her husband's back. 

Proceeds this way for a while and they start fucking at her house when no one else is home.  The "bully" convinces the mom that they should try to fuck in every room of the house.

They ultimately get to the sons room and the bully realizes he's turned on by dominating the son by fucking his mom right in his own bed.  He pulls out and cums all over the son's desk and belongings.  The mother is a bit annoyed by that but doesn't make a big deal of it.

This is the point where the bully hatches the plan to have the mother be his accomplice in "bullying" the son.  The wrinkle is that (at least at first), they're just doing mean things to him without him knowing who's responsible.

This could set up a whole series of "pranks" they play on him that would gradually ramp up in intensity and meanness.

Things like:

 - Bully fucks the mother with various items belong to the son. Basically anything that will fit in her pussy or ass ends up inside of her at some point.  Maybe the son wins a medal or some other kind of prize for winning a chess competition and the mother steals it and hides it up her ass all day while the son is freaking out looking for it.  There would be a scene where the mom is trying to "help" him find it but the medal is up her ass and the ribbon for it is just slightly visible above the waist of her pants

- The mother and the bully log on to the son's social media and cause some kind of havoc for him that way (note:  this is stolen from one of my favorite scenes in Conflicted)

- The mother sets some sort of "trap" or something that would cause the son to fall and maybe hurt himself a little.  Before setting the trap she hid a camera so they could record the fall.  They watch it on the TV later in the sons room while fucking on his bed.

- The mother installs some kind of spyware on the son's computer and they use it to control and record his webcam and ultimately get a video of him naked and jerking off to porn.  It might take a while, but the mother ultimately decides to upload it somewhere on the web so others can see.  She wrestles with the idea of uploading to a place where his classmates would be guaranteed to see.

- And so on....

I have no idea how it should end.  That's always the tricky part, I think.  The son would have to find out in some spectacular fashion I'd imagine,

Also not sure if I'd want to mother to ultimately corrupt the little sister for her help in bullying the son, or have her start doing mean things to the sister as well.

My ideal story has the mother pretending to be sweet and caring towards the son, but secretly enjoys it when he is beaten or humiliated. Up to and including seducing the bully, not to get him to stop, but to get him to send her videos of the crap he does to the son. It culminates in inviting the bully over to have him do his thing to the son while she eggs the bully on. Afterwards, they force the son to watch as they have sex in front of him.

My ideal plot would be a story from the point of view of the son's friend: you could tell it in a way that describes every step from flirting into the fucking of his friend's mom, in first person. The kinky thing for me would be that this lucky guy would feel guilty and think about his friendship every time he puts his penis inside this friend's mom holes (mouth would be so hot). You could write about his reflections on betrayal and loyalty, yet he won't hesitate on giving a facial to his friend's mom.

The mom could be separated or divorced, very scorned and open to new experiences, and adventurous woman. Beautiful, but not a supermodel.

For me it would be really hot if the son's friend becomes more evil every time, forgets about his friendship and even plots a threesome with his friend's worse enemy (or cousin, or another friend...)

The cuckold-son must be naive, a guy who believes in loyalty, pretty normal kind of guy. Clueless, completely, about whats happening to his mom. 

The story could escalate by developing a kind of cuckold-hotwife relationship between this lucky guy and his friend's mom, sharing her with classmates, immigrants, neighbors, soccer/basketball teammates, etc.

I leave the scenarios to you, but there are several: birthdays, trips, graduations, and so on.

If you like, we can chat on email about this, and other plots. I hope this helps

sent you my discord to talk in depth about this

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I have no idea how it should end.  That's always the tricky part, I think.  The son would have to find out in some spectacular fashion I'd imagine,

Also not sure if I'd want to mother to ultimately corrupt the little sister for her help in bullying the son, or have her start doing mean things to the sister as well.

Somehow missed this post before I made mine earlier.

I have the same issue. My brain tends to get fixated on 'drugging his birthday cake' and then handcuffing him to a chair, or tying him to the bed or whatever while he is passed out. But there has to be a better way.

Oh, and the sister/daughter? She joins in on the fun. 100%. Hell, given how little sisters tend to be, Mom might need to reign her in rather than corrupt her.

But yeah, having the sister on 'team evil' would probably help such a story. It deprives the son of an ally. It concentrates their efforts rather than diluting them (3 people have 1 target vs 2 people with 2 targets). It opens up more scenarios/opportunities for things to happen to the son/brother.

I don't have a preferred setting, but I like extreme scenarios. Plots where the bully and/or the mother would feed of the son's humiliation and go further down on him, or when the bully ruins mom's life just to laugh at the son. I don't like to bind my fantasy with realistic scenarios. I know some of them are fucked up and would the bully and/or the mother in deep trouble (maybe jail) in real life.

Here are some bad fantasies, read at your own risk:
1) Mom hoes around, maybe does porn, but this doesn't affect her career  or social life Instead, all of the fallout of it would go on the son alone
2) Bully ruins mom's life, gets her fired from her job, ostracised from her friends, maybe get her pregnant, just to fuck with the son
3) Bully fucks son, with the blessing or encouragement of mom
4) Teacher mom has sex with the entire school to humiliate the son
5) Bully goes to fuck every woman in son's life (mom, sister, aunt, boss, cousin...etc)
6) Religious mom warns son not think about girls at all, and beats him if she suspects that he does, yet she fucks his bully like a cheap whore
7) Bully manipulates mom to make her neglect her son, physically and emotionally, maybe outright disowns him
Bully leaves mom, who can't find one to satisfy her needs and forces her son to fuck her
9) Mom fucks son, not because she loves him or because he's hot, but rather to humiliate him and remind him that he'll never get a girl

Edit: Other fucked up fantasies
10) Son has a small cock, and mom bullies him herself and works to deny him sex at all (or at least having children) so he wouldn't pass the small dick genes, even encouraging his girlfriends (or wives) to cheat on him
11) Mom makes her son go through total sex change so he'd literally be bully's bitch

Oh, and the sister/daughter? She joins in on the fun. 100%. Hell, given how little sisters tend to be, Mom might need to reign her in rather than corrupt her.

But yeah, having the sister on 'team evil' would probably help such a story. It deprives the son of an ally. It concentrates their efforts rather than diluting them (3 people have 1 target vs 2 people with 2 targets). It opens up more scenarios/opportunities for things to happen to the son/brother.

Okay, you've convinced me    Little sis is on team evil.

I like your point about how little sisters can be.  Maybe the mom and bully have to convince a bit at first, but then she goes completely off the deep end.  Really life-threatening stuff.  Maybe she uses the spycams to know when he's jerking off and gets him swatted - the police break in and he's completely completely naked with his dick in his hand.  I dunno.  Just spitballing here....

Since I enjoy cruel women in my porn ... here is another scenario I'd love to read/watch:

The mother decides that son's girlfriend deserves a better man than her son. Mom then fucks son's bully as GF (maybe son too) watches to show her what a real man is like. Ends with  son forced to watch bully fuck GF, either with Mom joining in for a threesome, or she is belittling and degrading the son while they both watch.

That would be a great idea for a story on its own, and maybe also as a sequel to one of these. Part 1 is typical, a young man watches his mom fall in love with a bully and torment him, then Part 2 takes place years later, maybe a decade or more. The son is fully grown, has escaped from his mother / bully and built his own life, and after the humiliation of his youth finally finds the confidence to start dating again. That's when his mother tracks him down, and introduces his new gf to his old bully. Just spitballing, but I do like the idea of a guy suffering through the same ordeal over and over at different parts of his life