One day in February, Gwen was sleeping in one morning until she hears someone whisper,
"Psst! Gwen!"
Gwen groaned and asked in her sleep,
"What?"
"Happy Birthday!" A familiar voice said.
"Oh, that's nice." Gwen said as she tried to go back to sleep.
"Get up silly!"
The voice said as Gwen felt the covers pull off of her, getting her attention.
Gwen wakes up and realizes her sister Rose was standing right in her room.
"Rose, what are you doing here?" Gwen asked, trying to stay awake.
"Did you forget it's your birthday today sis?" Rose asked with a smile.
"Oh right! It is my birthday today! Oh, I'm 19 today!"
"And wait 'til you see what I have in store for you!" Rose said excitedly.
Gwen smiled and said,
"Can't wait sis!"
Gwen gets ready for her special day, wears a new pink dress along with the amethyst brooch Ms. Chalice gave her. Rose takes Gwen downstairs and outside and walk along the dirt road. Just then, Gwen is suddenly shaking uncontrollably and Rose fearfully asked,
"Gwen? Are you okay?!"
Gwen's eyes suddenly glowed blue.
"I am fine dear sister. I'm just gonna ask someone else to join us for our fun girl's day together."
Gwen said in a monotone voice, acting like she's being controlled against her will.
Rose looked at Gwen puzzled and asked,
"Gwen? What's going on with you? You look like you've been…"
Rose was about to finish when to her shock, she sees a ghost stick out of Gwen's chest and said,
"Possessed? That's right sister! Boo!" Ms. Chalice said, giving Rose quite a scare.
Ms. Chalice laughed as she exited Gwen's body and transformed back to her living form. Gwen has a brief headache, regains control of herself and scolds Ms. Chalice,
"Chalice! I thought I told you not to possess me!"
"Aw come on girlfriend, I just wanted to wish you a Happy Birthday!" Ms. Chalice said, acting innocent.
"Thanks."
"I heard through the grape vine it's your birthday today, so I thought I'd join you two for a special girls day out!"
Ms. Chalice said as she wrapped her arms around Rose and Gwen. Rose was unsure at first Ms. Chalice took notice of Rose's pregnant belly and asked,
"Oh wow, you're gonna be a momma soon?"
"Yeah, with twins. We're getting closer." Rose answered.
"Aw, babies are cute!" Ms. Chalice said with a cute face.
"Yeah, I'm gonna be an aunt Chalice." Gwen said
"That's great girlfriend. Now, whaddya say we get going? The three of us ladies?" Ms. Chalice said as she held Gwen and Rose's hands.
The trio head into Inkwell City and head to the movies to watch a new movie. Meanwhile, back at the cottage, Elder Kettle, the cups, William, Edgar and Margarine are helping set up the surprise birthday party they planned while Rose kept Gwen distracted. Cuphead and Mugman argue about where they should hang the 'Happy Birthday Gwen' sign."
"Over here!" Cuphead yelled.
"No, over there!" Mugman yelled back.
"Over here!" Cuphead yelled.
"Over there!" Mugman yelled back.
Edgar loses patience and sternly asked,
"Will you two knock it off?!"
Both cups stopped bickering.
"Sorry daddy-o. It's just the banner will look perfect over here." Cuphead protested.
"No Cuphead, it'll look perfect over there!" Mugman argued.
"Over here!" Cuphead yelled.
"Over there!" Mugman yelled back.
"Hey! I said 'knock it off'!" Edger scolded the cups as he wrapped his arms around them, breaking them up.
"Now, the quicker we get this party setup, the faster we're going to be ready for Gwen and Rose when they get back. So, let's all try to get along for a few hours. Okay Cuphead?"
"Okay, fine." Cuphead said with a disappointed look.
"Okay Mugman?" Edgar asked.
"Yes, sir." Mugman answered, also disappointed.
"Good." Edgar said as he stood up and went over to Margarine to continue setting up the table to place the birthday cake.
Edgar sighed and said,
"Man, those boys are harder to control than our girls were when they were their age."
"They're just boys dears. You know my twin sister Mildred and I had our share of fights too when we were little." Margarine pointed out.
"I know but, how does Elder Kettle deal with those two?" Edgar asked.
"Welcome to my life." Said Elder Kettle as he was putting up balloons.
Meanwhile, Gwen, Rose and Ms. Chalice head on over to the art museum to look at the new works of art displayed. Afterwards, they head on over to Inkwell Pier and ride some rides (except for Rose due to her pregnancy). On their way back, Ms. Chalice noticed the Carnevil and said,
"Ooh, the carnival! Let's check it out girls!" Ms. Chalice said excitedly.
Both sisters looked shocked and Gwen tries to warn her,
"Uh Chalice, there's something you should know!"
But Ms. Chalice was already making her way into the Carnevil and started playing games for prizes. Gwen and Rose follow her inside the carnival and Ms. Chalice holds up a giant plush kitty cat she already won.
"Here ya are girlfriend! I won you the grand prize! Happy birthday!"
Gwen and Rose were both shocked. Gwen took the prize from Ms. Chalice and said,
"Gee, thanks Chalice."
"Hey look sis! A photo booth!" Rose pointed to a photo booth.
Both sisters squealed and both got inside while Ms. Chalice went to play more games to win herself some toys. Rose pays the money in the coin slot and both sisters take four pictures. Two copies of the photo strips print out and each sister keeps one.
Unknown to the sisters, the Devil was spying on the sisters at his Carnevil through his underground telescope and asked,
"Hmm. Those two are having a sister's day together, huh?"
Henchman walks in with a cup of tea and said,
"Duh, I don't know if you know this boss, but it's actually Gwen's birthday today. Rose is taking her out while their parents have a surprise party waiting for her when they get home."
The Devil's eyes popped and gasped.
"Oh, my goodness! It is her birthday today! I gotta get her something! But what?" The Devil asked frantically.
"Uh, maybe you could take her out after her party without her family and friends knowing? You know? Dinner, dancing, or a trip to the destination of her choice?" Henchman suggested.
"Hmm, maybe. Perhaps I'll take her somewhere she's always wanted to see in the human world. But where?" The Devil pondered.
"Duh, that's a great idea boss! But remember, wait 'til after her party to take her to that place without her family and friends knowing."
"Yes, yes. Thank you Henchman." The Devil said as he leaves to prepare to visit Gwen later.
Meanwhile, Gwen, Rose and Ms. Chalice were walking back to the cottage and laughing while holding hands.
"Oh man, that was a really fun day!" Gwen said, carrying her giant plush kitty present.
"Yeah, you are quite a charmer and dancer Chalice." Rose complimented.
"Oh yeah Rosie! You are quite the big sister Gweny told me about." Ms. Chalice answered.
Rose smiled at Ms. Chalice as they were approaching the gate. They go inside the cottage when all of a sudden, everyone jumps out and yell,
"SURPRISE!"
Gwen is shocked and said,
"Wow! You guys didn't have to!"
"We wanted to Gwen." Rose said with a smile.
Cuphead and Mugman grab Gwen's hands and pull her up to the large red-velvet birthday cake. Everyone sang 'Happy Birthday' to Gwen, she blew out the 19 candles and everyone had a slice of cake, Gwen opened presents and everyone socialized. After the party, everyone leaves to go home back to the human world. Gwen thanked Elder Kettle and the cups for a wonderful birthday. Gwen goes upstairs to bed, opens her door and closes it.
"Happy Birthday my beautiful flower." A familiar voice said.
Gwen gasped, turned around and saw the Devil standing against her room divider with a smile. Gwen attempted to leave her room, only to realize the door was locked. Gwen looked for her butterfly and potted flower, only to realize they were fast asleep.
"Oh, don't worry, I put a little sleeping spell on them. They'll wake up later." The Devil explained.
Gwen armed herself with her ink pen and asked,
"What do you want? If this is another kidnapping attempt, I'm not going with you."
"Relax dear, this is no kidnapping attempt. I just remembered it was your birthday and I was wondering if you'd like to go out with me? Just name the place you always wanted to go and I'll take you there." The Devil offered.
Gwen is suspicious at first, but she decided to go along with it since she knew he always had a trick or two up his sleeve. And it was her birthday too.
"Hmm, okay fine. But any tricks on my birthday and you're gonna get it big time!" Gwen warned.
"Alright, alright. Now, tell me. Where have you always wanted to go in the human world but you never could?" The Devil asked.
Gwen thought for a moment, then she got an idea. Gwen gestured the Devil to come to her. He approaches her and she whispered her idea in his ear. The Devil smiled sinisterly and said,
"Perfect!"
The Devil wrapped his arm around her, tapped his pitchfork and both disappeared. In the human world, they both appeared in a land called Italy in a city called Rome. The Devil quickly makes himself a trench coat, shoes and a tall hat to disguise himself from the humans. Gwen is in awe of the sights of Rome. She and the Devil tour around and visit the Coliseum, the Vatican Museum, the Sistine Chapel, the Trevi Fountain and the Patheon. Afterwards, they both have dinner at a fancy restaurant.
"So, how are you enjoying your present?" The Devil asked as he sipped some red wine.
Gwen sipped some of her first red wine, looked up and said,
"Oh, it's amazing! I've always dreamed of coming here! This place is very famous for their artwork."
"Well, I'm glad you love it. You deserve the best." The Devil said with a wink.
Gwen shuddered, but kept her cool since he was treating her on her birthday and being careful at the same time. Just then, a human waiter brings them a large plate of spaghetti and meatballs with a side of breadsticks.
"Ecco i tuoi spaghetti e polpette con contorno di grissini. Buon appetito!" The waiter said in Italian.
"Grazie." Gwen thanked him in Italian.
The waiter bowed and walked away.
"Wow, you speak Italian?" The Devil asked.
"No, but I learned a few words." Gwen answered as she was eating.
The Devil decided to try something. He grabs a piece of spaghetti Gwen was eating and put it in his mouth and puckered his lips. He leaned closer to her face as Gwen was eating the spaghetti until she suddenly realized he was trying to kiss her again. With quick thinking, she bites the spaghetti, barely avoiding touching his lips and… SLAP!
The Devil winced in pain, trying to avoid attention from other humans.
"Why I oughta…!" Gwen whispered angrily.
"I'm sorry! I couldn't help it." The Devil apologized as he held his face where she hit him hard.
"I thought you promised me no tricks!" Gwen scolded.
The Devil sighed and started eating the spaghetti and meatballs while Gwen ate until she was almost full. Later, the same waiter brings over a big slice of tiramisu for dessert. After that, it was time for Gwen to go home. Gwen thanked the Devil for the night out to Rome and that she will escort herself home since she clearly didn't trust the Devil. She tapped her ink pen and disappeared back to her bedroom. She changed into her night gown, put on her invisible sweater and went to bed just in case.
Some time had passed in the two worlds. One afternoon, Gwen was finishing up her sketches at work, clocks out and heads back to the cottage. Gwen learned from Elder Kettle that the cups went with Ms. Chalice to play with their baseball in the woods. Gwen walks away from the cottage to find her three best friends. But she comes across Porkrind's Emporium and noticed a broken window.
"Uh oh. I hope my friends didn't do that." Gwen said to herself.
Gwen took a deep breath, walked up to the door and said.
"You can do this. I know he's a penny-pinching grump. Just be nice." Gwen reminded herself.
Gwen opens the door and noticed a customer she sometimes saw at the shop was laying on the floor unconscious.
"Did you deliver that package?" Porkrind called.
"Uh… what package?" Gwen asked, confused.
Porkrind looked up from his book and realized Gwen was at the door.
"Oh, it's you kid. What do you want?" He asked rudely.
Gwen took a deep breath, walked up to Porkrind and asked,
"Hey Porkrind, you seen my friends around?"
"Yeah, they broke my window, knocked Jerry out cold. So now, they gotta work off the debt!" Porkrind rudely explained.
"Oh… yeesh." Gwen said as she noticed the broken window and Porkrind hanging on to their baseball.
"Where did they go?" Gwen asked.
"They're making a delivery to the Fly Trap before closing time or else I'm selling the ball!" Porkrind answered.
Gwen's eyes popped, realizing the two frogs were still mad at her friends.
"Well, uh thanks Porkrind. I better go help them. Those two frogs I temporarily worked for and training under still wanna kill my friends." Gwen said.
She was about to leave until Porkrind reached for her shoulder to stop her.
"Don't worry kid. I gave them disguises and fake names. Besides they gotta work off the debt, not you!"
Gwen looked at him unamused. Just then, Jerry started to wake up and struggled to stand up.
"You okay Jerry?" Gwen asked.
"Well, well. Look at that. Sleeping Beauty decided to wake up." Porkrind said sarcastically.
Gwen looked Jerry as he regained consciousness.
"Sundown. Exploding shoes. The delivery." Jerry said wearily.
"Delivery's taken care of." Said Porkrind.
"Oh. Phew. In that case, I bid you a fond adieu." Jerry snickered as he turned to leave.
"Wait, did you say 'exploding shoes?'" Asked Porkrind, now concerned.
"Yeah, in the box. Sparkly dancing shoes. At sundown, they go… KABOOM!" Jerry explained and cackled.
"Well, see you both later." Jerry said, opened the door and left.
Gwen stood there in shock, realizing her best friends were delivering the exploding shoes to Ribby and Croaks. While Porkrind was thinking to himself, Gwen tries to sneak away and leave the shop to warn her friends. But just as she was about to slip out the open door, Porkrind closes it to stop her from leaving.
"Uh oh." Gwen quickly said as she knew she was in trouble.
Porkrind grabs her hand, pulls her back to the counter.
"Porkrind, what are you doing?" Gwen asked, feeling nervous.
"You've seen and heard too much kid. Now, you gotta keep your trap shut!" Porkrind scolded her.
"What do you mean? You sent them on another suicide mission! I also know it was you who sent them to Mt. Eruptus for that delicate package!" Gwen reminded him.
"Didn't they tell you I meant Mt. Eruptus Cleaners?! Not the actual Mt. Eruptus!" Porkrind corrected her.
"Oh wait, that's right. I forgot." Gwen remembered that part.
"Now, use that magic doohickey of yours and fix the window!" Porkrind ordered her.
"Okay, but what's in it for me? I could magically fix this and still blurt out what's in that package to my friends." Gwen reminded him.
Porkrind groaned, held up a kit and said,
"Fine! Do it and you get this free art supply kit!"
"Deal!" Gwen said and got to work restoring the window.
Porkrind grumbled to himself while he sat back in his chair and opened his horse-racing book and keeping an eye on Gwen. As Gwen was magically fixing the window, Porkrind started to feel guilty for sending her friends to deliver the exploding shoes. He tries to turn on the radio to the horse-racing channel to distract him but he is constantly reminded of the exploding shoes and the cups being killed.
After some time had passed, Gwen finished fixing the window and turned around and saw the guilt building up in Porkrind. Gwen never saw that side of Porkrind before and smiled.
"Aw, you care about them, don't you?" Gwen said as she folded her arms.
"No kid! It's just that…" Porkrind tried to deny it.
Gwen giggled as he cringed and finally lost it and groaned.
"Come on kid! We gotta stop them!" Porkrind shouted.
He jumps over the counter, grabbed Gwen's hand and opened the door. Only to realize the three cups returned with the package.
"Guys! You're alive!" Gwen said happily as Porkrind released her hand and let her join them.
"Hi Porkrind." All three said sadly.
"Give me that! Take this and GET OUT OF HERE!" Porkrind shouted.
The three cups gasped happily as Cuphead took the baseball.
"Gee, thanks, Porkrind!" All three said.
"I said git!" Porkrind scolded.
The three run away as fast as they could.
"As for you kid…" Porkrind turned his attention to Gwen.
He holds up the art supply kit and forcefully gives it to her.
"Here! Take it and GET OUT!" Porkrind shouted at her.
"Gee, thanks, Porkrind!" Gwen said smugly.
"I SAID GIT!" Porkrind shouted.
Gwen runs away as fast as she could to catch up with her friends. A few seconds later, Gwen heard an explosion and saw that Porkrind's shop was blown to smithereens by the exploding shoes. Gwen laughed as she walked away with her friends.
Meanwhile down in the depths of Hell, the Devil was flossing his bathroom until he heard the explosion and a piece of the ground fell down.
"What is going on up there?" The Devil asked.
He grabs his telescope to investigate, he sees the exploded shop and a burnt-up Porkrind.
"I hate those cups." Porkrind said.
"Cups?" The Devil asked and looked over to see Gwen walking with her three best friends walking happily together.
"All's well that ends well, eh fellas?" Ms. Chalice asked happily.
"You said it!" Cuphead answered.
"And how!" Mugman added.
"Eh, girlfriend?" Ms. Chalice asked Gwen as she jumped up on her shoulders.
"Yeah, girl! He got what he deserved and I got this free art supply kit!" Gwen laughed as Ms. Chalice hugged Gwen's head.
"Well, well, well. Hello again, Ms. Chalice. Friends with those two are we? And best friends with my beautiful flower are we? This will come in very useful indeed!" The Devil said and laughed evilly. Just then they hear Margarine call,
"Gwen!"
The Devil looked in his telescope again and saw Margarine running up to Gwen and the cups.
"Gwen there you are! I've been looking everywhere for you!" Margarine said, running out of breath.
"Mama, what's wrong?" Gwen asked, concerned.
"It's your sister Rose! She's gone into labor! It's time!"
Gwen and the cups gasped.
"Rose is having her babies?!"
"Yes! We need to get to the hospital now! Your father's waiting in the car! Let's go!"
Margarine said quickly and grabbed Gwen's hand and ran for the door portal with the three cups tagging along.
"This I gotta see!" Ms. Chalice said as they were running to the cottage to reach the door portal.
"Well, well, well. Rosy Cheeks is having more than one baby right now huh? This I gotta see!"
The Devil said evilly.
He puts away his telescope goes up to his magic mirror, taps it and watches Gwen, her parents and the three cups riding in the car in the human world to the hospital in downtown Boston.
They arrive at the hospital and were instructed to wait in the waiting room. The cups play with some toys while Gwen sketches in her sketchbook. After an hour, a nurse comes out and announced,
"The twins are born and ready. You're all welcome to come in."
They all go into the birthing room and see William at the beside with Rose holding two sleeping newborn babies in both her arms. Gwen and her parents go up to Rose and look at the little girl and boy. Gwen had tears in her eyes and said,
"They're beautiful. What are their names?"
"Emma Jane Smith and Jack Thomas Smith." Rose answered.
"Emma and Jack." Cuphead and Mugman said in unison.
"Aw, cute names sister!" Ms. Chalice said.
"May we dear?" Margarine asked, gesturing to hold the infants.
Rose nodded and Margarine lifts Emma and Edgar lifts Jack in both their arms.
"Hello little Emma." Margarine said with tears in her eyes.
Edgar looked at Jack and smiled.
"I may not have gotten a son, but I have a grandson now." Edgar said.
Cuphead and Mugman watch the grandparents meeting their grandchildren.
"Uh momma, can we hold them?" Asked Mugman.
"Alright, but mind their heads boys."
Margarine told the cups as she hands Emma to Mugman and Edgar hands Jack to Cuphead.
"Aw!"
All three cups said together. Mugman looked at Emma as she opened her eyes and stared at him. Mugman smiled and said in baby-talk,
"Hello Emma, my name is Mugman. I'm a best friend of your auntie."
Emma smiled at Mugman as he gently tapped her nose and said,
"Boop!"
Jack opened his eyes and stared at Cuphead holding him. Cuphead looked at Jack and said in baby-talk,
"Hey there Jack. I'm Cuphead. Your auntie is our best friend."
Jack smiled at Cuphead as he gently tapped on Jack's nose and said,
"Boop!"
Ms. Chalice takes both twins from the cups and said,
"Hey there little ones. Your auntie and I are girlfriends!"
Emma and Jack stared at Ms. Chalice and smiled.
"Chalice, let Gwen meet her niece and nephew." Edgar told Ms. Chalice.
"Okay daddy-o." Ms. Chalice said.
She hands the twins to Gwen and she sits down in a chair and says to them,
"Hi Emma. Hi Jack. I'm your Aunt Gwen. No one will ever harm you both as long as I'm around. I promise you."
Emma and Jack smile at Gwen, then they start crying.
"Oh, I think they're hungry." Said Rose.
Gwen gets up and hands the twins back to Rose. Gwen hugs William and said,
"I'm so happy for you both."
"Thanks Gwen." William replied.
"Well, we should let them tend to the children. Come along Gwen, Cuphead, Ms. Chalice and Mugman."
Edgar said as he grabbed his coat.
"Yes dearest daddy-o." All three cups said at once.
Gwen hugs Rose and quietly says,
"See ya!"
Gwen leaves with her parents and the cups and head back home. Gwen and the cups return back to the Inkwell Isles and back to the cottage.
Meanwhile the Devil watched everything that happened with Henchman next to him.
"So, Rosy Cheeks had twins eh? A girl and a boy?" The Devil asked.
Henchman had a few tears in his eyes and said,
"Aw, Rose had twins. They're so cute I just wanna hold and cuddle them!"
"Yes, they are cute Henchman. And I believe those two new arrivals could be… useful to me." The Devil said evilly.
Henchman gasped.
"B-But boss! You said you had no interest in babies! You don't even like children!" Henchman protested.
"I know I said that. But change of plans, Ms. Chalice and the newborn twins are the key to finally getting both cup's souls and to marry Gwen once and for all!" The Devil explained his evil intentions.
"Aw jeez." Henchman said worryingly as the Devil laughed evilly.
