Springfield Hilton Plaza
It was three hours into the the prom before the band started playing slow dancing music as Milhouse danced with Sherri for the first dance and later Terri and Lisa was about to ask for a dance before later tonight where he would be on the fourth floor with an each room occupied by a Milf however he could see that Laura wanted her dance for the night as she approached him oozing sensuality wearing a black super-hot cut out mini dress.
Laura: Don't forget your dance with me handsome! *Who got real close when they slow danced before she guided his hand to her thigh on her right side were he noticed another key card before hearing* See you tonight lover.
It was then that Milhouse noticed he would have an entirely different dance card full tonight when he noticed the others Milfs smirking at him.
Meanwhile with Jessica Lovejoy it was an entirely different case as she was watching Lisa eying Bart and her dancing wondering if she was going to finally admit she's bisexual or if she was looking at Bart before smirking at an idea she saw on a YouTube Video involving a Halloween party in Quahog that Involved a tubby Guy who dressed like Optimus Prime and Cat girl who she knew would later become one of the most hottest WWE Divas to come from the female Luchador ranks. When she noticed Bart's Wandering eye toward Cookie Kwan and that girl in the Cut out Mini dress it made her smirk at the thought of what she wanted to do next.
Jessica: *thinks to herself while looking toward Lisa* so you ask me out and look at girls Bart I'll make this a night you won't forget. *Then she whispered into Bart's ear* Hey Bart how about you head upstairs to room 419 and we could really have a party especially since I'm leaving for LA after graduation I really want to give you something to remember me by..
Bart: So you're finally standing up to your father without collateral damage *Remembering when she blamed him for stealing money from the church which Rev. Lovejoy never apologized for.* So what's your plan this time taping me having sex with you and sending it to your father to show you're not your daddy's little girl?
Jessica: Why Bart that's a wonderful idea just remember to keep the lights off and let me do all the work. *she purred into his ear* I'm so looking forward to seeing how well hung you are*she said before letting her leg move between his before saying* Somebody likes the idea.
When the dance was over she watched Bart leave the Ballroom not knowing he would run into Elizabeth Hover who took him into the Coatroom still wearing her Catering uniform which consisted of a white shirt black vest and miniskirt which shown she was also wearing a garter belt and tiger printed thong when she lifted it up for Bart to see.
Bart didn't have to be told what to do and a little detour never hurt.
Back at the party Lisa was watching Milhouse with hunger and jealousy in her eyes as he was dancing with Ruth Powers before she noticed Jessica Lovejoy standing beside her.
Jessica: Hey Lisa thanks again for giving the Cheerleading squad a chance to setup this party.
Lisa: You're welcome but why aren't you dancing with Bart?
Jessica: He busy at the moment but that's not why I came over to see you. *Hands her a key card with the room number on it* Milhouse told me to give this to you and asked for you to wait upstairs in Room 419 and he also wanted you to keep the room dark.
Lisa *looks at the card key* Thanks Jessica if it wasn't for the fact you're a total bitch for leading my brother on I think we could have been great friends.
Jessica: Thanks and coming from that party you and the twins crashed changed you for the better. *thinking the word submissive cunt while smiling at her knowing what would occur tonight.* Have fun trying to get into Harvard.
Lisa: Have fun being my brother's one night stands. *walking away*
At first Jessica Lovejoy felt some pang of pity for pulling this prank on Lisa but after that comment she felt none at all and would enjoy reclaiming the SB card from the hidden camera later.
In the Coatroom Bart was finding out how Liz earned the title of Springfield High's blowjob queen as he was getting sloppy deep throated by Lisa's former teacher before he shot another load of his cum into her mouth.
Bart: Damn if I knew you could do this I would have requested you as a private tutor.
Liz: *Stroking his cock between her tits* But you'll still need a leg up on your algebra Bart and I'd be happy to give you a few pointers over the summer between work hours. *Slick his cock which starts twitching before he shoots his cum on her face and tits before she takes some of if off her face and lick it.* Oh I see that your little head agrees with the arrangements.
Bart: Well your arrangements were very convincing.
Liz: I know now don't you have hotel room to go to.
Bart: How do you know that? *Liz just held up the Card key marked 419* Oh yeah must have fell out my pocket.
Liz: Here you may want this one later. *Hands her another key card marked 403* Meet me after your fun I want to taste her flavor of your freshly mixed juices as I suck your dick.
Bart: Will do Liz. (Leaves the room)
When he's out of sight Liz smirks before picking up her phone.
Liz: Hey Jessica your lover boy been stalled long enough for your just remember your deal. ((Then hangs up her phone before going back to work))
In room 419
Bart entered the room and could see the pink panties that were left the floor along with the silhouette of the girl who was lying on the bed fingering her with legs spread open waiting for him. He smiled as he closed the door and locked it behind him before walking to the foot of the bed and crawling between her legs as he moved the girls hand which was covered in her juices he partook in tasking before allowing his probing tongue to let his date know she was in for the night of her life.
While Lisa was enjoying the probing tongue of who she though was milhouse and gave a throaty moan as she pushed his head deeper between her legs before she had to cum and then he stopped it was then she felt thick member enter and throb in her hungry and locked her legs around his waist and was pushing him into her that seemed to feel so good to her as she tightened up her pussy before feeling him kiss her.
Bart was kissing who he though was Jessica but when he put his dick in her pussy is tightened up real quick to the point he was about to cum but moved lower to one of her tits before he began sucking on them before hearing something that would shake him to his core.
Lisa: Oh yes fuck me Milhouse
Hearing that Bart cut on the light and could see he was still balls deep in his sister who had blindfold and tied herself to the bed.
While he was upset about being tricked by Jessica into fucking his little sister he couldn't stop she was a beast and wasn't letting go and surprised him when she ripped out of the bonds before pushing him on his back and riddling him with abandon before taking off her blindfold and looking down at Bart who though she was going to kill him only to smirk down at him.
Lisa: Bart where have you been hiding this thick cock if I knew you had this I would never had hit you there. *Held his face while bouncing on his cock before before she kiss him again* did you always want me big bro or did you just think it was Jessica?
Bart: I thought it was Jessica and if I knew you were going to be like this I would have done this sooner. *Still fucking Lisa, but now he was holding on to her ass.* you can't stop can't you Slutty my slutty little sister.
Lisa: Nope and now I get to enjoy my big brother's cock as he's breeding me like his personal whore but tell me who has the better rack me or Jessica?
Bart: You Lisa, and to tell you the truth I sometimes did walk into the bathroom on purpose just to see your luscious tits and wonderful ass.
Lisa: Good to admit the truth isn't it, now since you said I have a wonderful ass how does it compare to Jessica's who who has the more spankable ass between us me or the flat chested cunt who tricked us both.
Bart: You of course Lisa *Slaps Lisa ass and felt her tighten her pussy * and I'm going to enjoy spanking it for now own.
Lisa : Oh Bart you say the most naughty things but now comes the most important question Big brother who the better Fuck in bed me or that wannabe bad girl of a skank whore who tricked us *tighten her pussy as she rides him faster.*
Bart: Lisa not that I really mind but why are you badmouthing Jessica so much?
Lisa: Because I always hated how she treated you, and now that I finally have you it's such a turn on and let's be honest this just proves that Jessica doesn't really deserve you if she willing to pull a fucked up stunt like this. *still tightening up with each thrust* Now tell me who's the better whore your younger nerd of a sister who riding your pole with abandon or the skank who though a little incest would stop our fun together.
Bart had to admit hearing Lisa talking dirty and badmouthing Jessica made his dick harder before shooting a large load deep inside her womb as she gave off a throaty moan as she savored the victory of stealing her brother away from Jessica Lovejoy hoping that her mistresses would be proud of her especially their mother who never liked her after framing him for stealing from the church.
She also made note to remove Sim cards from all the hidden cameras she found after they were done because both she and Bart were going to need reminders of this night and the night to come especially when she starts attending college.
She knew her horndog of a brother would keep busy with a few one night stands he would have a recording to remember this night of forbidden lust between them.
She started to wonder how her wonderful Master was doing with his conquest.
After the party was winding down the twins didn't waste any time waiting for awards or taking pictures with classmates. They wanted Milhouse's cock and didn't slouch about getting him on the elevator and striping him of his pants before kneeling at his feet and took turns deep throating him before they stopped at the fourth floor and headed to Room 401 no words were said between them as their bodies did most of the talking before he put the two girls on top of each other as he took turns fucking them to the point they were kissing each other and letting him use their bodies as he wished before he left them to rest..
In room 403 Edna was already being eaten out by Liz who had a vibrator already stirring her pussy before he removed it and replaced it with something larger before he got it slick enough to stick it in her ass making the former elementary teacher moan and rutt with abandon before shooting a load in both holes before moving on to Edna's sexy body who he picked up and started fucking her while standing up until them moved near a wall as he continued to dominate her with the same vigor as he did Liz and the Twins Sherri and Terri before she passed out in a violent orgasm and left her on the bed to sleep.
Milhouse had one more room to visit before Cookie's and Marge and the Powers...
Helen Lovejoy's and he was looking forward to it...
As soon as he entered Helens room she wasted no time in pouncing him...
Wow Helen you're ready to go!
Helen: Well of course I am sweaty Reverend doesn't even touch me anymore and tell me and when I remind him I have needs he brushes me off by saying I should read the bible and pray over relieving my urges or he tells me that I should set a better example for Jessica since she'll be graduating soon so fuck yeah I need sex and if Kurt won't tend to my personal needs then you can take his place filling my horny pussy with cock!
Milhouse: Don't worry I'll be happy to help you with your needs.
? Me too Milhouse. *Jessica Lovejoy stepping out of the shadows still fingering herself from watching*
Helen: Jessica how did you? *Shocked from seeing her daughter*
Jessica: Well I followed you and Milhouse and up here and convinced the maid this was your room and she let me in, but I never expected my mother who has high morals to be such a slutty whore of a cougar or bagging Milhouse before I could or the fact he sporting such a lovely cock. *She said walking over to them* I don't know if i get upset or proud to be more your daughter that daddy's little girl.
Helen: Well we'll talk about that later but right now I have to know if you're going to tell your father?
Milhouse: Yeah besides I though you would be banging Bart right now anyway.
Jessica: Well to answer your question Mother I'm not going to tell day anything as for my date he currently putting that boner of his to someone who needed it more. *Smirks at Milhouse as she got in a chair and started fingering herself and asked with a moan* Now are you going to finish pleasing my mother because I want you to fuck me too.
Helen: Sure as soon as you tell me the truth about your real choice for college because I saw the UCLA booklet and kept quiet about the the tickets.
Jessica: Wow mom I guess I couldn't fool you I had no intention of going to that Christian college in Arkansas I want to get away from dad he's too controlling and the fact I had to hide my sextoys with Dusty McCormick there was no way in help I was going to tell dad about the change in schools until the check he signed was cashed.
Helen: Oh I already knew that dear you're my little girl now sit back and enjoy the show because I'll be watching you next. *She said before she turned milhouse over with surprising strength before lowering herself back into him and started to ride him with abandon as she said.* Oh yesssss I'm finally free to a naughty whore without judgement from my daughter or limp-dicked husband. *Helen screamed out while Jessica was watching and fingering herself to her mother's rhythmic fucking *
Jessica: Damn all this time I thought I was a bad girl I not even close. *Thinking to herself*
When it was Cookie Kwan's turn she was on the bathroom enjoying herself in the Jacuzzi as she was fingering herself moaning to the combination of pleasure she was feeling from her fingers and the bubble jets before looking to see Milhouse in the doorway.
Cookie: Oh you done with other girls now and ready for me? *About to step out of the tub.*
Milhouse: Of course my tigress we both deserve something much kinkier than a bedroom don't you think?
Cookie: I could think of a few ideas. *smirks at the idea before asking* did you bring your Hank Hardcore gear with you?"
Milhouse: What do you have in mind?
Milhouse only watched as Cookie only smiled at him letting him know he'd like it
Marge and Ruth Powers were talking at a table outside by the pool as the students were enjoying the after party celebration of their prom leaving them still as chaperones since both were listed as Lifeguards. As a Laura went to order their drinks from the bar both Ruth and her got the chance to finally talk again.
Ruth: So Detective Simpson how's working on the force?
Marge: I'm enjoying it I don't know why I let Homer talk me into quitting the first time? *She giggled at how much power she had and the perks of the job* Not only that but my job pay is more than his ever could and I'm already being asked to replace Wiggum as chief of police.
Ruth: That good to hear Marge but you know Homer is going to be an idiot about it and demand you quit.
Marge: I'm already planning to throw him out after the Kids graduation and while Lisa is heading to Harvard and Bart is heading to France again with Maggie. Me and my sisters planned something out just to make sure Homer doesn't try to make me look bad and ruin my job.
Selma: Yeah our little sister shouldn't have to sneak around enjoying what Homer refusing to give her at night.
Patty: I'm just surprised it took so long and he doesn't mind sharing either.
Ruth: so he fucked another pair of twins before he fucked Terri and Sherry... interesting.
Patty and Selma would make a note to meet them later before hearing the moaning of someone on the fourth floor balcony which made them look up to see Cookie Kwan enjoying herself as a unknown guy who features were hidden from view was doing her from behind as the crowd below them cheered.
Cookie's voice: Oh yes hank punish my kinky pussy with your wicked rod. *while moaning as she was getting her pussy pounded.*
Marge, Ruth and Laura who finally returned with their drinks already knew it was Milhouse giving Cookie such a pounding and would be making notes to have him do the same thing or something else of that nature to them later when it was their turn before he made his way to college. However unknown to Marge and Ruth they would be getting their chance to do that sooner than the thought as Laura already had a talk with Patty and Selma along with Liz and Edna, after convincing the hotel manager to agree to let them use the hotel next week do a porn called M.I.L.F. Hotel which wasn't very hard since Liz was very convincing underneath his desk.
Epilogue.
Springfield changed after Prom Night for some people more than others...
Marge Simpson worked her way up the ranks of the Springfield Police Department from Chief of Detectives to Chief of Police after her divorce from Homer was finalized after she had proof of him having an affair with Lurleen lumpkin seen that a good chance to get a clean divorce. It also dint hurt that Patty and Selma set him up by paying for his room at the hotel he stayed stay in...
And he was none the wiser since it was his kind of hotel which had Wide screen TV's and his favorite food including Hot Wings.
However he didn't know that it had a special reputation that would allow the lawyer hired for Marge by Lindsey Naegle helped either since she called Lurleen who didn't have any trouble drugging his drink or featuring him in a sex tape with them as the stars with homer never being the wiser.
After His the Divorce from Marge he was now living with Lurleen apartment and was enjoying himself thinking his troubles were behind him only to come into work one day to find out he was fired from the Nuclear Power Plant a month after Burns death when supervisor hired by the new owner of the plant's was allowed to look for people that would have to be laid off due to being seen as an insurance risk to the plant by following the guidelines of Wayland Smithers' will with the reason being that Smithers nor Burns didn't want Springfield to become the next Chernobyl because he went to sleep on the job. He would later leave Springfield as Lurleen's manager co-manager with Lindsey who had a unique relationship as they lived in Nevada.
After Milhouse left to travel the world without telling Lisa, The now submissive Simpson daughter started clinging to Bart after they couldn't stop so they keep having Incest after the prom and didn't hesitate to live with him in his new home giving to him in Burns' last will and testament which surprised them both.
Maggie became a Rock star with incredible histories and now she is more than happy.
As Luann Van Houten she almost had a heart attack after discovering His son was a pornstar, she discovered the hard way when he for the first time did one porn movie showing his real face, who would know that Milhouse Van houten her son was a pornstar, but his dad was more Proud then anyone to see his son getting all the ladies and getting pay for that.
After Helen Lovejoy decided she had enough of her Husband neglecting her and decided to drug him and handcuff him to a chair so she could show him a sex video of all her moments with Jessica bonding as they had sex with Milhouse before they kick him out only for him to die of a heart attack an hour later.
Edna and Hoover still are catering making Milhouse cakes with the real size he got they call it the Big van houten, and sometimes they use the cakes for other things besides eat.
Sherri and Terri Still Have Milhouse Number in their cellphones and sometimes are called for porn movies in their disguise personas, the money sure is good for their studies and life.
Cookie signed Milhouse as his partner in Real Estate and even lived together enjoying the friends and business partners with benefits until Ms. Kwan told him she would be pregnant with a daughter.
He would later hear that Marge was also pregnant with his child due to the fun they had at the Christmas party in the guest room at Bart's Mansion, boy that sure was the most intense Christmas they have in that room, they would enjoy telling him that him and Cookie that their daughter would soon have a half-brother to play with.