It was Christmas Eve once again in the two worlds and Gwen was once again magically preparing her cabin for her family to spend Christmas together. After settling her family into the cabin, Gwen was out with her fiancé Clarence for Christmas shopping at the mall before it closed early.

After shopping, the couple head back to his apartment to wrap presents.

"Can you believe it's our first Christmas together honey?" Gwen asked.

"Yeah. It is." Clarence answered sadly.

Gwen is concerned for Clarence since she's noticed he didn't look excited for Christmas.

"Clarence, is everything okay?" Gwen asked.

"Totally. What makes you say that?" Clarence answered in denial.

"You seem to not be looking forward to the holiday. What's wrong?" Gwen asked.

Clarence gave a heavy sigh.

"You really wanna know?" Clarence asked.

Gwen nodded.

"Fine. I'll tell you. Christmas was very difficult for me growing up." Clarence revealed.

"Oh…" Gwen said, remembering he grew up in an orphanage.

"You see, every year at Christmas, we barely got any presents and we had no one to celebrate with. It didn't make it better when I was on the streets for a while." Clarence explained his lonely past.

Gwen's heart sank, feeling awful for Clarence never having a real Christmas.

"I'm so sorry." Gwen said, feeling empathetic.

"Thanks. But it's fine. I just don't know if I'll ever get into Christmas like you and the cups." Clarence said.

"Clarence, that's all in the past now. You're here with us. We're your family now." Gwen reminded him.

"I know and I'm grateful. But it's just hard to let it go." Clarence said sadly as he got up and went up to his room.

Gwen is heartbroken and decided she wanted to do something for him to make this year the best Christmas he's ever had. She magically finishes wrapping up the presents, brings them back to the cabin and places them under the tree.

Just then she hears the door open.

"Hiya Gwen!" Cuphead and Mugman called.

Gwen giggled at the cups.

"Hey guys." Gwen answered.

"There's fresh snow! Let's go sledding!" Cuphead said excitedly.

"I got the sled for us!" Mugman added as he dragged a sled.

"Okay, okay guys. I'm coming." Gwen said as she magically dresses herself warm.

Gwen joins the cups outside in the snow and teleports them to the top of a large hill. Both cups get on the sled while Gwen sits behind them.

"Ready fellas?" Gwen asked.

"Yeah! Yeah! Yeah!" Both cups answered excitedly.

Gwen gives a little shove and the trio sledded down the mountain.

"WHOOO!" The trio yelled out.

The sled slid down to the bottom of the hill and the three all laughed.

"That was awesome!" Cuphead exclaimed.

"Let's do that again!" Mugman added.

"Okay!" Gwen agreed.

She teleports themselves back to the top of the hill and they keep sledding for a while until they get tired out.

"Okay, I think we've done enough sledding. We should head on back." Gwen said, feeling tired.

"Same here." Mugman agreed.

They head back to the cottage and rest up. Gwen thought for a moment and got an idea of how to give Clarence the best Christmas ever. She noticed the cups napping on the floor and decided to sneak off. Gwen goes upstairs to her bedroom and decided to teleport somewhere.

But suddenly as she teleported…

"SURPRISE!" Both cups exclaimed and jump on her shoulders.

Gwen reappeared outside Santa's workshop in the North Pole with two unexpected stowaways.

"Ugh! Guys! What are you doing?!" Gwen scolded.

"We knew you were up to something!" Mugman said.

"I can't believe it! This is the North Pole!" Cuphead said excitedly.

"And that means…" Mugman said.

"SANTA CLAUS!" Both cups yelled excitedly.

"Guys! Calm down! I know this is exciting, but I gotta ask Santa something." Gwen explained.

"What are you gonna ask him?" Cuphead asked.

"I'm gonna ask him if he could give Clarence the best Christmas ever so he'd be happy for once around this holiday." Gwen answered.

"But Gwen, you can give him the best Christmas." Mugman pointed out.

"Well, I tried to cheer him up, but nothing worked. So, I thought if anyone knew about bringing joy and happiness, it was Santa." Gwen said.

"Oh… okay." Both cups said, now understanding.

"Thanks guys. Now stay close to me guys. I'll do the talking." Gwen instructed.

Gwen knocked on the door. A little elf opens the door.

"Hi there. Is Santa here?" Gwen asked.

"Yes, please come in! Santa needs your help!" The little elf said.

"What's wrong?" Gwen asked.

"There's been a robbery! Come on!" The elf exclaimed.

Gwen and the cups go inside the workshop and to their shock, they find all the presents and toys gone. The elf leads Gwen and the cups to Santa's office. They find Santa sitting at his desk upset over all the presents stolen.

"Santa! Gwen is here!" The elf said.

Santa looked up and saw Gwen with the cups.

"Wonderful! Bring her here!" Santa ordered.

Gwen and the cups follow the elf to Santa's desk. The elf leaves the office and closes the door.

"Ho ho ho Gwen! You've come at a dire time!" Santa said.

"What happened here?" Gwen asked.

"We don't know how it happened, but someone stole all the presents! If we don't get them back, it'll be a giftless Christmas." Santa sadly explained.

Both cups gasp in horror.

"No presents?!" Both cups said and both started crying.

"Hey, hey calm down guys. We'll get them back." Gwen assured them.

Both cups stop crying.

"We will?" Cuphead asked.

"Yes Gwen. We need your help to find out who stole all the presents and save Christmas." Santa said.

"Maybe we should start by looking for clues. See if the thief left anything behind." Gwen suggested.

"To the scene of the crime!" Mugman declared.

Gwen and the cups start searching around the workshop for clues. Just then, Gwen notices something odd. She notices some footprints leading outside. She follows them outside and the tracks led to reindeer stalls. Gwen opens the stalls and checks the reindeer but finds no presents inside.

Just then, she notices a little young reindeer calf scared and huddled in a corner and a group of reindeer calves are bullying him. Feeling sympathy, Gwen shoos the other reindeer calves away and slowly goes to the frightened reindeer calf.

"Hey, it's okay. Shh. I'm not gonna hurt you." Gwen gently said.

Gwen magically makes a handful of grass and sticks her hand out.

The reindeer calf looked at Gwen and sniffed the grass. The reindeer calf slowly approached Gwen's hand and ate the grass.

"Aw good boy." Gwen said as she petted him.

Suddenly, Gwen noticed something odd about the reindeer calf. She noticed his nose was red colored unlike the other reindeer's noses were black.

"Oh, I see your nose is red. Is that why they're picking on you?" Gwen asked.

The reindeer calf nodded sadly.

"I think it's cute." Gwen complimented.

The little reindeer smiled and licked Gwen's face.

"Aw thank you…" Gwen said and noticed the reindeer's collar revealing the reindeer calf's name: Rudolph.

"…Rudolph." Gwen finished.

"Gwen, it's nice you made a new friend, but can we get back to finding the stolen presents?" Cuphead asked impatiently.

"Oh, right, right." Gwen remembered and got up and searches the stalls with Rudolph tagging along.

Just then, Rudolph sniffed something odd. He gestures Gwen to look at what he was sniffing at.

"What is it boy?" Gwen asked.

She looked and saw a small pile of black fur.

"Hey guys! Rudolph found something!" Gwen called.

Cuphead and Mugman approach Gwen and notice the black fur pile.

Mugman look one good look and sniffed, to his disgust.

"This looks and smells familiar. Only one person I know of has this type of fur." Mugman said.

"Wait, you don't think it was…?" Cuphead was about to ask until it finally clicked.

"THE DEVIL!" The trio exclaimed.

"I think we need to pay that jerk a visit!" Cuphead said angrily.

"Yeah, and Gwen'll teach him another lesson!" Mugman added.

"Now, now guys. We'll check around the underworld to see if he has the presents or not. For now, the Devil is our prime suspect." Gwen assured them as she placed the fur in her pocket.

"Okay then." Mugman agreed.

The cups gather around Gwen, and she teleports themselves to Hell. They appear in her prison bedroom once again but to their shock, they find Rudolph had stowaway with them.

"Oh no, not again!" Gwen grumbled.

Rudolph excitedly wanted to help Gwen.

"Look Rudolph, we gotta get you home! It's too dangerous here!" Gwen whispered.

Rudolph licked her face, insisting he wanted to help.

"Okay, okay you can help! But you gotta keep quiet!" Gwen instructed.

Rudolph nodded.

"Let's go." Gwen said to the cups and Rudolph.

The group stick their heads out of the door to make sure the coast is clear. To make doubly sure, Gwen shapeshifted into her ghost form and searches the area. When nobody is around, Gwen rejoins the group.

"Okay, all clear!" Gwen whispered.

Gwen, the cups and Rudolph exit her bedroom and start searching around the fiery underworld. Cuphead checks behind the tapestries, Mugman checks the elevator and Gwen checks around the Devil's bedroom. But they couldn't find the presents anywhere.

"Any luck guys?" Gwen asked the cups.

"Nope." Cuphead said.

"Uh-uh." Mugman said.

"Okay, maybe the Devil didn't do this. We should head on back. Maybe there's something we missed." Gwen said.

But before Gwen could teleport out of Hell, they are suddenly wrapped in ropes and are levitated in the air. They hear a familiar evil laughter echoing.

"Well, well, well. Looks like there are a few rats poking their noses where they shouldn't!" The Devil echoed.

"Where are the presents?!" Cuphead angrily asked.

"What presents?" The Devil asked as he walked into the throne room.

"Don't play dumb with us! All the presents Santa's delivering to all the nice kids! We know you stole them!" Mugman angrily answered.

"Stolen presents? What are you talking about? I don't have any presents!" The Devil asked impatiently.

"Then how do you explain this piece of evidence we found at the crime scene?!" Gwen asked as she managed to snag the pile of fur from her pocket and dropped it down to the Devil.

The Devil took one look, realizing it was indeed his fur.

"This is crazy! Who would be stupid enough to steal my fur?!" The Devil angrily asked.

"Where are the presents?!" Gwen asked, losing patience.

"I told you! I don't have them! In fact, I didn't do it!" The Devil snapped as he blew fire.

Just then, they hear a noise, the group turned around and saw Rudolph trying to pull a tassel next to the throne. He pulls it, and the throne spins around. To everyone's shock, they find all the presents behind the throne.

"AHA!" The trio exclaimed.

"So, it was you!" Cuphead said.

"You're the thief!" Mugman added.

"WHAT?!" The Devil exclaimed in shock, seeing all the presents behind his throne.

"This is ridiculous! I didn't put those there!" The Devil exclaimed angrily.

"Then how do you explain all the presents behind your throne?!" Gwen asked impatiently.

"I don't know! Someone put them there! I think someone's trying to frame me!" The Devil angrily guessed.

"Can you prove it?" Gwen asked.

"Yes, I can prove it! You want me to show you proof?!" The Devil asked.

"If what you're saying is true, then yes! Show me proof!" Gwen answered.

"UGH! Fine!" The Devil frustratingly agrees and drops the group to the floor.

"OOF!" The cups exclaimed.

The group is untied and follows the Devil to his magic mirror.

"Show them what I was doing while the presents were stolen and brought to me!" The Devil ordered his mirror.

The mirror shows a vision of the Devil singing in the shower 'Deck the Halls' and is singing in an embarrassing-like way. Gwen and the cups laugh hysterically at the Devil, to his anger.

"ENOUGH! NOW FOCUS!" The Devil yelled.

The trio stopped laughing and looked at the mirror. It showed someone small wearing an elf hat snatching a pile of fur from the bathroom, magically hiding the presents behind the throne and magically disappeared back to the North Pole and placed the fur in the reindeer stall.

"Wait, is that one of Santa's elves?" Cuphead asked.

"Sure, looks like it." Mugman agreed.

Gwen realizes the Devil was telling the truth.

"Oh, boy. I can't believe I'm saying this but…" Gwen hesitantly said.

"Go on my beautiful flower, say it!" The Devil ordered.

"Well… I don't wanna admit it, but I-I think he was… telling the truth." Gwen shamefully admitted.

"Thank you, Gwen. Now let's go catch the real culprit." The Devil said.

"Ooh! Boss, can I come too?" Henchman asked as he ran in the throne room.

"Ugh, fine." The Devil reluctantly agreed.

Henchman squealed excitedly as the Devil teleports the group back to the North Pole into Santa's workshop along with the presents. The elves are startled to see the Devil again as Santa comes down the stairs.

"You found the presents! Well done!" Santa congratulated Gwen and the cups.

"Santa, the Devil didn't do this! One of your elves stole all the presents and tried to frame him!" Gwen explained.

All the elves gasped including Santa.

"What?!" Santa exclaimed.

Santa turned to his elves.

"Who is responsible for all of this? And be honest!" Santa warned.

Just then, Rudolph headbutted an elf carrying a bag full of magical supplies and some of the Devil's fur.

"Wait a minute! Here's the real criminal!" The Devil said as he grabbed the elf by his shoulders and lifted him up to Santa.

"Elf number 13! How could you?" Santa asked shockingly.

"Why?! I'm so sick and tired of making toys and singing that stupid song! So, I thought I'd feel better by making everyone miserable and framing the Devil since he is the evil one! I would've gotten away with it if it weren't for that meddling human kid and cups! And that freak baby reindeer!" Elf number 13 angrily confessed.

"You should be ashamed of yourself! I'm sorry you don't like making toys, but this isn't the answer!" Gwen scolded.

"Now, how should we punish him?" The Devil asked evilly.

"I have a suitable punishment in mind." Santa said, having an idea.

"Oh no…" Elf number 13 said nervously.

"For the crime of stealing all the presents and trying to frame the Devil, you are hereby demoted to cleaning the reindeer stalls!" Santa announced the punishment.

"B-b-b-but they are smelly and messy!" Elf number 13 complained.

"Then I suggest you get started!" Santa said and tossed him a bucket and a rake.

Elf number 13 groaned as the Devil put him down and a few elves escort him to the reindeer stalls to get started.

All the elves cheer for the group. The Devil wrapped his arms around Gwen and the cups, to their annoyance.

"Well, now that we have all the presents returned, let's get ready for Christmas!" Santa announced.

"Yay!" All the elves cheered.

Rudolph leapt into Gwen's arms and gave her kisses.

"Aw, thanks Rudolph." Gwen thanked.

"Whoo! We did it Cuphead!" Mugman said.

"Yeah, now we'll be able to get our presents!" Cuphead said.

"Yes, guys but first, I gotta talk to Santa." Gwen reminded them.

"Oh yeah!" Both cups said.

"What are you asking for Santa this year?" The Devil asked.

"How is that any of your business?" Gwen asked sternly.

"Hey, you blindly blamed me for a crime I didn't commit. So, I want retribution!" The Devil reminded her.

"Fine! I'm gonna ask Santa to give Clarence the best Christmas ever so he'd stop being sad around Christmastime since he was always alone with nothing." Gwen hesitantly answered.

"Oh. How touching." The Devil said sarcastically.

"Now, if you'll excuse me." Gwen said and walked upstairs to Santa's office.

Gwen enters his office and approaches his desk.

"Santa? I know what I want for Christmas this year." Gwen said.

"Ho ho ho. What is it dear child?" Santa asked.

"Well, is it possible you could give my fiancé Clarence Hopewell the best Christmas ever because he grew up in an orphanage his whole life and never had a good and happy Christmas. So, can you help him?" Gwen asked.

"Aw, ho ho ho. You want me to help him? He was always a good boy even though his caretakers never showed him any love. But he already has what he needs to give him the best Christmas ever." Santa told her.

"What's that?" Gwen asked, feeling confused.

Santa grabbed a mirror and showed her reflection, making Gwen realize something.

"What? Are you saying I can give him the best Christmas ever? But I already tried that, he didn't care for them." Gwen said sadly.

"Are you sure about that?" Santa asked.

"What do you mean?" Gwen asked.

Santa grabbed a snowball and made it glow like a crystal ball and showed her what Clarence was doing. She saw him holding a present with his name on it from herself and gave a smile. He also grabs a present with her name on it from Clarence himself. Gwen realized Santa was proving a point.

"Oh, he does care for Christmas now because of me. I am his best gift he's ever gotten." Gwen realized.

"That is correct my child. You are the best gift he ever received." Santa confirmed her theory.

Gwen smiled and had a few tears in her eyes.

"Aww!" Both cups said.

Gwen turned around and saw the cups and Rudolph happy for her.

Just then, an elf came running in the office.

"Santa! We got a problem!" The elf yelled.

"What's wrong Elf number 3?" Santa asked.

"There's a snowstorm blowing and it's too foggy for the reindeer to see!" Elf number 3 explained.

"We need some kind of powerful light to help us see through the storm! If it were possible on any of the reindeer!" Santa said fearfully.

Just then, Gwen got an idea and looked at Rudolph.

"Here's a little gift for helping me. So, you can help others too on Christmas." Gwen said as she magically enhanced Rudolph's nose.

To Rudolph's shock, his nose started glowing bright red, startling everyone.

"Wow, what a bright nose Rudolph has!" Santa said in amazement.

Santa knelt to Rudolph and Gwen.

"Rudolph, with your nose so bright, won't guide my sleigh tonight?" Santa asked.

Rudolph thought for a moment, then he happily nodded.

Santa has Rudolph join the other eight reindeer as the elves put reins on Rudolph at the head of the team.

The elves load Santa's sleigh with all the toys in his bag and Santa prepares to take off delivering presents.

"Wow, that was genius Gwen!" Cuphead complimented.

"Thank you. Who knows, maybe they'll write a poem, or a song, or even a cartoon about Rudolph." Gwen guessed.

"I can see that happening." Mugman agreed.

Just then, Elf number 13 comes running in exhausted and tired from working in the reindeer stalls.

"Okay! I finished! Can I go home now?!" Elf number 13 angrily asked.

"Hmm…" Santa said until the Devil interrupted.

"Actually Santa, can I punish him next? I'm not gonna let him get away with what he did to me." The Devil asked.

"Very well, Devil. Just return him when he's done." Santa agreed.

"Wonderful!" The Devil happily said.

Gwen knelt to Rudolph and gave him a kiss.

"You help Santa deliver those presents, okay buddy?" Gwen asked.

Rudolph happily nodded and licked her face.

"Good boy Rudolph. Maybe you'll go down in history for this." Gwen said.

She rejoins her cup brothers as Santa gets into his sleigh. The Devil teleports the group back to Hell. The Devil magically dresses Elf number 13 in a French maid outfit.

"For trying to frame me, you get to spend Christmas cleaning my beloved realm!" The Devil announced his punishment.

A cleaning cart with supplies magically rolls in.

"Now, get to work! Chop chop!" The Devil ordered.

Elf number 13 quickly grabbed the cart and gets straight to work.

"Duh, I'll keep an eye on him boss." Henchman assured his boss.

"Wonderful!" The Devil said happily.

Henchman goes to keep an eye on Elf number 13.

"Well, we should go. My family's waiting for us." Gwen said as she was about to leave with the cups.

But the Devil placed his hand on her shoulder.

"Not so fast my beautiful flower. You're not off the hook yet." The Devil said.

"Why?" Gwen asked.

"Because I still want penance from you for blindly blaming me!" The Devil sternly answered.

"Well, what do you want?" Gwen asked, losing patience.

"Well, just because it's almost Christmas, I'll give you two choices. You could either join that idiot elf cleaning my beloved realm." The Devil answered.

"And the second choice…?" Gwen nervously asked.

The Devil raised a mistletoe and waved it. Gwen nearly throws up again, remembering last year when she lost a bet to the Devil and had to give him a kiss.

"EW!" Both cups exclaimed.

"No way Gwen's ever gonna kiss you!" Cuphead argued.

"Yeah, she would never!" Mugman added.

"You mean… she never told you about last year?" The Devil asked.

"Huh? What do you mean by that?" Cuphead asked.

"Why don't you ask her?" The Devil asked, knowing they wouldn't believe him.

Both cups turned to Gwen.

"Gwen? You didn't actually…?" Mugman nervously asked.

Gwen facepalmed in embarrassment.

"Oh no… you didn't." Cuphead said, figuring it out.

Gwen nervously nodded.

"Last year before Clarence came along." Gwen shamefully came clean.

"Why? Why did you do it?" Mugman asked.

"Because I lost a stupid bet to him! Okay?!" Gwen snapped.

Both cups stood in shock.

"What bet?" Cuphead asked.

"I bet him he couldn't get on Santa's nice list last Christmas, but he somehow succeeded. And he said if he won, I had to give him a kiss!" Gwen finally admitted as she cringed.

Both cups gasped.

"Gwen, what were you thinking?!" Mugman scolded.

"Yeah! I'm the impulsive one!" Cuphead agreed.

"It was stupid! I know! I'm sorry I kept this from you guys!" Gwen apologized.

"Well, we've all done stupid things. I should know." Cuphead said after thinking about it.

"Guys, you're my best friends. And as my best friends, you promise me you'll never ever speak a word about this to anyone?" Gwen asked and held out her pinky.

Cuphead and Mugman looked at each other and both felt empathy for her. They reach their pinkies to Gwen's and wrapped around each other's.

"We promise." Both cups said.

"Okay, enough of the sentimental hogwash. Let's go Gwen. Make your choice!" The Devil said, losing patience.

Gwen stood up and faced the Devil.

"We should look away." Mugman suggested.

"Yeah, good idea." Cuphead agreed.

Both cups turn around to avoid watching Gwen. Henchman flew above them and held the mistletoe. The Devil held Gwen once again, puckered his lips and leaned towards her. Gwen shuddered and said to herself,

"Just a little kiss. Just a little kiss... again."

Gwen took a deep breath, stood on her toes and once again kissed the Devil. Henchman had tears in his eyes, feeling happy for his boss once again. After 5 seconds, they stopped kissing. The Devil whispered in her ear,

"An excellent choice."

Gwen wiped her lips, once again feeling embarrassed. She knelt to her knees and held her head in shame. Both cups come up to her and comfort her.

"Gwen, we should go." Cuphead suggested.

"Yeah, our family's waiting for us." Mugman added.

"Okay guys. But promise me we never speak a word of this to anyone." Gwen reminded them.

"We promise." Both cups agreed.

Gwen teleports themselves out of Hell and return to the cabin, where the family was waiting for them.

"There you three are. Dinner is ready!" Margarine said.

"Coming mama!" Gwen said.

"Oh boy!" Both cups exclaimed.

They join Gwen's parents, Elder Kettle, Clarence, Rose, William, Emma and Jack at the dinner table and eat dinner together. Gwen and Clarence head upstairs to bed. Gwen feels guilty for being forced to give the Devil a kiss again.

"Hey, Gwen?" Clarence asked.

"Yeah?" Gwen asked.

"I'm sorry for my behavior earlier. It's just I never had a good Christmas all my life. And you were right, I do have a family now. And you know what the best gift I've ever gotten was?" Clarence asked.

"No, what?" Gwen asked.

"It's you. You're the real gift." Clarence answered.

Gwen smiled and gave him a kiss. Both humans went to sleep together.

The next morning was Christmas Day. Gwen and Clarence join the family downstairs when they all wake up to an amazing surprise. They find a truckload of presents for the family. Elder Kettle and the cups enter the cabin to join Gwen and her family when they are also shocked to find a whole room full of presents.

"What… what's all this?" William asked.

Gwen realized Santa granted her wish to give Clarence a wonderful Christmas.

"I… I don't know." Rose said.

Clarence stood in awe of all the presents he was never given in all his years.

"Merry Christmas Clarence." Gwen whispered.

"Gwen? You did this?" Clarence asked.

"Well, I did ask for help from a friend." Gwen admitted.

Clarence had a few tears and kissed his fiancé.

"Thank you." Clarence thanked.

Gwen felt joy in her heart, giving someone a wonderful Christmas.

"Come on everybody! Those presents ain't gonna open themselves!" Cuphead yelled excitedly.

"Yeah, let's go!" Mugman agreed.

Everyone gathered their presents with their names on them and opened their presents together.

Later, Gwen showed Clarence her favorite things to do at Christmas. She takes him with the cups and once again go sledding. Later, they go around and sing Christmas carols for some locals. Finally, they dance with each other at their Christmas Party at the cabin.

Gwen was happy to give Clarence a wonderful Christmas as well as enjoying her second Christmas with her families in the Inkwell Isles.