Good night
The rules of the drinking challenge were simple: Whoever drank the the most zap apple hard ciders before one of them fell unconscious or ended up getting sick won. It was a battle of pure endurance and willpower with no magic, shapeshifting or sabotaging allowed. Once the two agreed to the conditions to play fair, the tiebreaker went underway while the other mares set about dousing the fires and repairing what damage could be immediately fixed thanks to the destructive pillow war, leaving the pair to their own devices after making them swear not to cheat or destroy any more of the castle.
Driven by sheer competitiveness and determination, Chrysalis and Twilight pounded glass after glass with relentless fervor. Only a few glasses in, and the potency of the infamous cider was already taking a toll on them. Their bodies started swaying dangerously, speech gradually getting more slurred and raucous as the dizzying effects started taking hold. The other six mares secretly took bets on how long they could keep this up, capping at an hour max.
Two hours of non-stop drinking later...
“Ah’m gonna… gonna get ya. Then I’m gonna finally beat Sparky!” Chrysalis droned, lazily grasping at the fourth bottle of cider at the edge of the table she laid sprawled out on.
The bottle was barely out of reach for her. Despite being drunk out of her mind, glassy eyes dizzily attempting to stare down the bottle to will it to her, Chrysalis might have been able to move barely enough to grab it were it not for the equally drunk Twilight latched onto her back like a sleepy sloth.
“Nuh-uh, ah’m gonna win. Ya can’t beat th' great 'n powerful Sparky!” Twilight slurred, giggling madly to herself. Any attempt to go after the bottle herself halted as she started rubbing her cheek against Chrysalis’ back. “Dish is so soft. It’s like a… like a thing that’sh soft.”
Chrysalis’ body shifted as she chuckled. “You ish so magical with words.”
“Damn straight! Ah’m like a wizard. Or somethin’.”
“Wha? Nah, you’re too fluffy ta be a lizard. Stay fluffy!”
Twilight gave a weak, playful slap on the back of her head. “Nah, fool! I dun said wizard! Wiz! Erd!”
Chrysalis craned her head to look at Twilight. “Da buck is a wizerd?”
“A wizard is, you know, t-the thing. That’s magical and awesome. Like, Swirl-star the afro awesome!”
Chrysalis gave up her attempts to go after the bottle, resorting to simply staring out into space as she flopped on the table. “Oh dang, I like afros.”
Sighing wistfully, Twilight curled up on Chrysalis’s back, drawing circles on her carapace, “A-a-and that’s why I wanna be like ‘Lestia. She’s got a super cool afro. A-a-and she’s really pretty, and smart, and n-never called me Egghead, and just totally understands me, and… and...” She trailed off, mumbling incoherently.
“Hmph. I never called you Egghead...” Chrysalis muttered bitterly.
“Huh?”
Chrysalis wiggled angrily, albeit uselessly thanks to Twilight’s weight, attempting to grab the bottle again. “Doesn’t matter! Ah’m gonna drink this, and beat you, a-a-and feel good about mahself!” Her hoof suddenly shot into the air triumphantly. “Ah’m gonna make Queen Chrysalis great again!”
“Whatchu talkin’ about, Chryssi?”
“A-ah was the bestesh queen!” Chrysalis bristled, raising her voice. “Everypony thought ah was the knees bees! B-but then you had to come along and ruin everything!”
“O-oh no, I did the t-thing?” Twilight’s eyes began to water, her ears pinning back.
“All the things! The friendships! The kindness! A-and makin’ me feel fuzzy and wanted! Ah don’t want the fuzzies! Fuzzies are for squares!”
Twilight started tearing up, sucking in her lower lip. “But-but-but I love the fuzzies!”
“A-a-and then you started beating me up, you bully!” Chrysalis clenched her eyes, slamming her hoof on the table. Tears threatened to slip through her closed eyelids. “Y-you are just so good at everything, and-and friendly, and everypony loves you! But ah’m just scary bug horse who doesn’t know how to make friends or win games! You win at games, you win at life, you win at things! I’m just a big, scary loser.”
Twilight let out a sharp gasp. She sniffled in a dry sob, and murmured pleadingly, “No, Chryssi, no…”
“LOSER!” Chrysalis slammed her hoof on the table, causing Twilight to wince. “Ah’m always gonna be a loser! Cuz momma told me ah was a predator! And my momma’s momma told her she was a predator, and-and predators are super strong and win at everything! And my momma’s momma’s momma—"
“—But you won today!” Twilight exclaimed, cutting through her tirade. “Ya beat me up real good!”
“Fool!” Chrysalis swung her body around with all the grace of a wrecking ball, forcing them to face each other, and bumping their skulls together with a light bonk. She glared at her hotly, pressing her face against Twilight's snout. “Ah didn’t win nothin’! Ah couldn’t has done no good without your bud-buds!”
“But they be your bud-buds too! Like ah’m your bud-bud!”
“I don’t wanna be scary bug horse who can only win with bud-buds! I wanna be a strong, independant queen, who don’t need no bud-buds! Even if they're super nice and made me feel good, or say stuff like “let’s play again”! Ah dun wanna be weak loser anymore! Ah wanna be a winner!”
Twilight threw her hooves around Chrysalis' shaking withers, and pulled her in tightly, pressing their barrels together. “Ah’m sorry, mah queen! Ah dun messed up by being super scary and I made you saaad!” she wailed. “Ah jush wanted everypony to see how super special awesome ya are! Ah know everypony kinda sorta thinks you're scary bug horse, but ah wanna show ‘em who ya are!”
“Dat I’m a loser?!”
“Stupid Chryssi! Hush!” When Chrysalis opened her mouth to argue back, Twilight lurched forward and angrily nommed Chrysalis’ nose, causing her to yelp. She pressed herself up on her hind hooves until their faces were level, and then a little higher, bearing down on Chrysalis with a stern gaze. “Ya ain’t a loser! You’re, like, the coolest thing ever! Ah have to be on my super duper tippy hooves when playin' with you! Cuz you're smart, and strong, and tricksy! Ah’m strong 'cause you are strong! You are my amazing, bestes rival and beshtest friend!”
“Say whaaa?” Chrysalis drawled out breathlessly.
“Exactly! But ah don’t wanna make you sad! Sometimes, ya drive me crazy, but happy Chryssi is pretty Chryssi! Pretty Chryssi is best Chryssi!” Wearing a goofy smile, Twilight extended her feathery wings and threw them tightly over Chrysalis' neck, cuddling her for all she was worth. “Best Chryssi is mah Chryssi! Mah cool rival friend!”
A lopsided smile found its way onto Chrysalis’ face. She leaned back under Twilight's comforting weight, until her head came to rest on the table. She shifted her head around to nuzzle Twilight's cheek, making the alicorn let out a breathy squeak. Her foreleg reached up, shivering nervelessly, and she simply lay it over Twilight's comfortable back. “Dat. Right dere, is why ya will always be my bestie and rival too. Ah admit, I was scared of ya bud-buds.”
“Huh? Why?”
“Because they be important to ya. And… a-and I didn’t wanna mess up and lose ya cuz I’m scary bug horse.” Chrysalis suddenly glanced to the side, taking particular interest in the texture of the table. “Ah like your friends." Her voice was low, cracking wistfully around the edges. "Ah just wish I was awesome like you so they can like me too.”
“I just said ya were awesome.”
“Ah know. Just… ya know how I get. I didn’t have ta think 'bout feelin’ stuff and makin’ friends till ya came 'round. Ah hate… ah hate feelin’ all nervous ‘n stuff when ah’m under pressure.”
“Dat’s why I trapped mah bud-buds in here with you! Yay friendship prison!”
“Friendship prison is best prison!” The two laughed together. Gradually, they fell into a comfortable silence.
Chrysalis was the first to talk. “Sparky?” she whispered softly.
“Ya?”
“Thank you for being beshtest friend and rival.”
Twilight cooed happily, smiling a soft, peaceful smile. “Awww, I like you too, ya big lovebug," she murmured, nuzzling at Chrysalis' neck.
Suddenly, Chrysalis started spazzing out in horror, throwing Twilight off her barrel as she rolled around and patted herself.
“GAAAH! THE FUZZIES ARE BACK! GET IT OFF! GET IT OFF! GET IT OFF!”
Twilight flailed about in panic, rapidly patting Chrysalis’ body as if trying to put out a fire. “AH’LL SAVE YA, MAH QUEEN! THOSE FUZZIES AIN’T GONNA GETCHA!”
“IT’S GETTIN’ WORSE! SAVE MEH!”
“AH’M SAVING YA! DON’T DIIIIE!”
Outside the entrance of the council room, six pairs of eyes watched the ensuing madness from a safe distance, drinking their own bottles of hard cider while sitting on foldout chairs courtesy of Pinkie Pie. They had long since finished repairing what they could. But rather than go to bed and letting Starlight keep an eye on Chrysalis and Twilight, Starlight suggested they could all stay up and enjoy the sheer entertainment of the drunken duo.
“So girls,” Starlight started after taking a swig, “didn’t I promise the midnight show was going to be amazing?”
“Heck yeah. No way I could miss out on Lovebug and Twi going wild! Totally worth staying up late!” Rainbow laughed.
“Wow, who knew Chrysalis was such a softy? Kinda cute, in a weird way.” Pinkie said.
“I should be more upset that Twilight locked us up here, but I’m kinda glad we got to see those two actin’ cuter than a pair of playful kittens in a catnip field. Never gonna let Chrysalis live this down, though.” Applejack smiled as she took a generous gulp of her family cider.
“I couldn’t agree more, Applejack,” Rarity sighed blissfully. “Although I would rather not have to deal with any more property damage, this has been a most lovely sleepover.”
“U-um, speaking of cute,” Fluttershy began, “am I the only one who thinks they look cute together?”
The group turned their attention towards the council room. Chrysalis ended up flailing on the ground, crying that this was the end for her. Twilight staggered about in a flustered panic, grabbed the last bottle of cider with both hooves, and poured the contents all over Chrysalis to “purge the fuzzies”. When Chrysalis calmed down, gasping in relief, they both took a swig, smiling to themselves.
“I couldn’t agree more. They really do bring out the best in each other.” Starlight giggled.
“Just one question, though.”
All eyes suddenly turned to Rainbow. “So who was the gay pony Chrysalis talked about earlier?”
“You’ve been thinking about that all night, haven’t you?” Rarity asked, smirking.
“H-hey, I just wanna set the record straight, alright? Besides, you girls can’t seriously tell me none of you are curious about who Chrysalis was talking about.”
“I think the answer is pretty clear,” Fluttershy answered sagely as she took a calm sip of her cider. All eyes turned on her.
“Oh yeah? So who’s the mystery mare Chrysalis was talking about?”
Fluttershy smiled as she tipped her drink to the drunken duo, as Chrysalis was nuzzling Twilight’s cheek, thanking her for saving her life from the fuzzies.
“Chrysalis miscounted. There’s actually two.”
The other mares gave each other confused looks at the ambiguous answer. But after a few seconds, they all collectively gasped in awe.
Starlight lifted her drink, tapping it against Fluttershy’s. “I’ll toast to that. To friendship, great sleepovers… and whatever the hay that is.” she said as she nodded her head towards Chrysalis and Twilight, who decided to break out into the world’s goofiest music number, happily singing— more like shouting—about pink fluffy unicorns dancing on rainbows.
The other mares clinked their drinks together and continued to watch over their friends, both old and new.
“To friendship and weirdness.”
What's up, my fellow paladins?
You thought this chapter wouldn't come for at least a month, but it was I, Dio! 
And so, with a heavy heart, the sleepover finally comes to a close.
This chapter hit quite a lot of high notes for me, allowing me to put on display the deeper characters I had in mind for Twilight and Chrysalis. They're just a total joy to write for, and despite having a few hiccups along the way in trying to properly write some chapters, I am super grateful to have made the decision to turn what would have been a one-shot into a multi-chapter short story about friendship and shenanigans.
In general, a lot of this wouldn't be possible without you lovely readers and my helpful proofreaders. When I first wrote Chrysalis's First Royal Meeting, it was simply a funny idea done on a whim. But after receiving so much love and attention on it, I bought into the idea of making a sequel that delved into the humor a bit more and also explored the mane seven and their interactions with Chrysalis. That in itself evolved into a story with undertones about coming out of your shell and taking that step forward into making more friends. Fun morals complimented with questionable and naughty humor. That's my kind of gig! 
So, I know I go on about my proofreaders virtually every chapter, but I cannot stress enough how important Setokaiva and Midnight Quill have been into helping me ensure the quality of work and stability of my sanity. They have been absolutely wonderful friends that provided valuable insight and corrections for the whirlwind of madness that is my initial drafts.
But even more important than that, thank you all for taking time out of your busy day to dabble in my shenanigans and having a wonderful time. At the end of the day, I write this both for myself and for you all to enjoy, and knowing that I'm able to make someone's day, even a little bit, makes the countless hours of slamming my head against the keyboard repeatedly worth every penny of my medical bills.
So enough of my ramblings, I would love to hear from all of you. What do you think of everything that's transpired until this point? Would you all enjoy another sequel, or are content with the story as is? If you want a sequel, what sort of "First" would you want to see Chrysalis do next? What are your thoughts on Twilight's and Chrysalis' character arcs? Whatever it is, leave a comment and let's discuss it!
Until the next adventure, stay classy my paladins! 
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Not only do I want a sequel, I support this ship.
Chrysalis' First Heath's Warming? (Hearth Swarming?)
Chrysalis' First Family Dinner
Chrysalis' First County Fair
Chrysalis' First Summer Sun Celebration
Chrysalis' First Nightmare Night
Chrysalis' First Mission to Spread Friendship
Chrysalis' First Babysitting Job
Chrysalis and the Haunted Mansion
Chrysalis and the Secret of the Clock
Chrysalis at Pirate Cove...
...Wait... I seem to have drifted...
PFUDOR
MOAR SEQUEL PLS OMG!
Excellent fic.
8370838 You, sir, have the best ideas for sequels.
It was quite nice indeed.
Laughing the whole time.
I don't quite know what I was expecting from this chapter, but it definitely wasn't a couple of winos trying to talk about their feelings.
I remain confident that a couple of winos trying to talk about their feelings is way better than anything else I might have expected.
Fluttershy is flexible in her shipping, I see.
“Chrysalis miscounted. There’s actually two.”
Well, Twilight shipping herself with Celestia did make it pretty obvious, yes. Chrysalis probably just didn't count herself because she's not a pony, per se, and thus not a mare. I definitely see her as the type to engage in that kind of technically accurate wordplay.
I enjoyed this story and I wouldn't mind seeing more of this couple as a couple. I'd love to see a sequel but only if you had a good idea for one. I'd hate to see you try to force it just for the sake of a sequel.
Still, there are plenty of places you could take one, like those listed here:
8370838
And don't forget Chrysalis' first Hearts and Hooves Day.
Kind of expected the contest to end with Twilight waking up in bed with either Chrysalis, Celestia, or Chrysalis and Celestia.
Still, hope there is more as I enjoy Twilight's and Chrysalis' interactions with each other.
8371339
you mean "Chrysalis' First Buffet", right?
Chrysalis First Grand Galloping Gala would be good.
Their eloquent conversation was great. Though I kept imagining Thorax watching on and trying to make the earth swallow him whole out of embarrassment.
Why am I certain Pinkie is recording everything on camera?
If love to read more, you write those characters wonderfully.
Hmm... Chrysalis's first Free Buffet, I mean Hearts and Hooves day, Chryssie's first Nightmare Night, Chryssie's first Job Interview, Chryssie's first Kindergarten Teacher Job, Chryssie's first Birds and the Changelings Talk, Chryssie's first Ali-Con, Chryssie Discovers Alicorn Aphrodisiac, Chryssie Visits the Crystal Empire, Chryssie's first Self Defence Class, Chryssie Goes to the Opera, Chryssie Goes to the (Adult) Toy Store, etc.
8370433
AUTOCORREEEEECCCTTT!!!!!!!!!!!!!!
m.quickmeme.com/img/72/7228ef135c2759600e1bfeb42e669160abb8cb9646dc0281719bd4bc088683dd.jpg
8371417
derpicdn.net/img/2014/2/13/550857/large.jpg
Candyass come Heart and hooves day. “Hey Twily, you wouldn’t BELIEVE the cutest pictures I received from your friends the other day that were taken at some sleepover you had at your place some night or other. When am I going to get invited??
”
Heheheh, woooow man. This was some incredible stuff
From start to finish, this was fantastic work well done 
Good show man, good show!
I love you marry me1111
Fucking awesome dude, you have an incredible fic here, now about sequels, just keep them coming forever, ill read them all :D, do one with chrysalis and twilight patents and celestia visiting the hive (the big one and which is a secret brothel, in which twilight patents are secret clients, and celestia toó, and shining and cadance, and the girls, and spike, and everypony else, though not all of them are for sexual services, but twilight doesnt know that ).
This was the best possible note to end this story to
On comments, damn. It's just too much, there's too much that I'd have to comment on, so much of this awesomeness that got mixed in my head. Sorry, I won't be able to help. Just know that you did it right
On a sequel? Well, that's obvious to me!
Chrysalis First Love Confession!
Or
Chrysalis First Date!
There should be a sequel where they fall in love, but not in a mushy way. In a very competitive, passive aggressive, nose noming way.
To friendship and weirdness, indeed.
That was a lot of fun, particularly the Secret Moon and pillow fight chapters. The way the girls eventually opened up a bit to Chrysalis and started working on an actual friendship too was a good development.
I know I'm late, but this was fantastic! Thanks for all the laughs dude.
8371339
I'm Technically correct. "the best kind of correct."
This was just utterly, and totally AMAZING! Every bit just, was so perfect. And your Chryssi and Twi work so damn well together, hell your Chryssi alone is freaking amazing, but how well she plays off Twilight, and all without being a shipping thing. Just.... seriously I was laughing all the way through. Also, I so called the Secret Moon game and who had what! Nice strategy from Rarity and Chryssi.
Also, Chryssi supplying Spike with Playcolt..... all of the YES!
We so need more of these two!
Ending with dancing on Rainbow s... Best story ever.
Sexy. Cute. Thrilling. Sad/Romantic? And...so... sooo funny!
PS. You used chekovs gun this often, mihgt as well going on several reloads...and yet I didn't see it coming. Way to distract like a changeling! Darn smart writing.
Thanks!
oh my god this whole thing was glorious and hilarious
sequel please
anything is fine tbh, lots of people have come up with great ideas.
This is quite fun and humorous.
I love seeing Chrysalis's different side whilst maintaining her edginess.
All hail To Friendship and Weirdness! This sleepover story has really turned out well :)
i just found this , and i swear i haven't been this drawn into a fanfic in years, both the tension and the pace of the story ,combined with the dialogue and the comedy is GOLD .DUDE THIS IS HECKING AMAZING. This is the most fun ive had with a fanfic and i wish it got more recognition
ART
10205851 RIGHT?? ^_^ I keep coming back to it because it's so freaking good!
10287604
i swear ive seen you around i think we hang around the same fics
I can’t stop coming back to this chapter because this has gotta be one of the best stories I’ve read on this entire site. 🤣
This is one of the sweetest, funniest, best-written, most absolutely glorious pile of memes I've ever seen. I didn't even know you could create the same amount of tension in a pillow fight and Secret Moon game as you could in a climactic fight scene. I love this so much <3