A/N: now we're starting to get to the reason I wanted to set this in the 20s: it was the time of the flappers. For some reason I like that, and thought it would be good to have in this story. I'm not entirely sure of the full workings of a debutante ball, so I've missed bits out and made the remains a bit like a Cinderella-type ball, mostly just talking and dancing

I've also decided to go with the names for Jim Dear and Darling from pre-production, which were Jim and Elizabeth Brown. Also, the son's going to be called Jim Jr… this basically comes from reading the Lady and the Tramp wiki

Sorry for any mistakes, by the way. I'm just finishing this off at about two in the morning, but I'll go back and check everything over soon, hopefully as I write the third chapter

Kjspirit23: Thanks so much. I'm really proud of it

Little-Angel-02: Thanks! Hope this is soon enough

Zerocchi: I'm sorry *cries in a corner*


Chapter Two: The Debutante Ball

"Jim Dear, I just wish you'd let me tell her," Lady heard her mother say through the open window, as she came up the path to the house.

"I know Darling," her father said, "but she caught me getting off the phone to Aunt Sarah. She figured it out."

"She's such a clever girl," Mother said proudly. "I just hope her baby brother or sister will be as smart as she is."

"Oh, I'm sure he will be, Darling," Father said wistfully. Lady knew her father had always secretly wanted a son, although he loved her very much. He had mentioned once, when she asked, that babies weren't easy to take care of, so the possibility of having a son must be why he had agreed to try for another one.

"I wouldn't mind so much, Jim Dear, but did you have to tell Aunt Sarah today? What if she suddenly decides to come over? This is Lady's special day, and I don't want Sarah to ruin it for her."

Finally Lady decided she'd had enough of listening in. "I won't let her, mother!" she called in through the window. Coming into the house, she added, "Don't excite yourself too much, mother. Not in your condition."

Mother rolled her eyes playfully and said, "Come on, Lady. We'll go to a boutique and pick out a gown for you to wear tonight."


Tramp sat on a box by the back entrance of a cafe. He and Champ had run an errand for the owner after meeting Lady and Missy in the park, and in return they'd been offered anything they wanted from the menu. Champ lay at Tramp's feet, gnawing on a bone, as Tramp ate lunch.

"Maybe I should get Pige something," Tramp thought aloud. "But what would you get a girl like her, huh, boy?"

Champ sighed as if to say he was already tired of the conversation.

"You've been talking about this girl you met since you got here," commented the son of the cafe's owner, a large, English, dark-skinned boy about Tramp's age. An English bulldog, the family dog, hung around his feet, hoping for some food to fall on the floor. Because of his size, strength and dog, Tramp and his friends often called the boy Bull.

"I can't help it," Tramp replied. "She's something special, Bull. She really is."

Bull sighed. Tramp's one weakness was girls, and he'd seen Tramp thinking about a pretty girl he'd just met before, but this time seemed slightly different. Maybe he was imagining things, or maybe Tramp just liked this girl more than the others. It could just be that this girl – whose name Tramp hadn't actually mentioned yet, considering it probably wasn't Pige – also had a dog, whereas the women Tramp usually went after didn't have dogs. Bull didn't know.

"Look, matey," Bull said, "you're the girl expert. Besides that, I don't even know this girl's name. If you want my advice, don't ask me for help."

"Who should I ask then?"

Bull blinked. Tramp was… stuck. It looked like Tramp had no idea what to do. He was debating out loud if he was supposed to get Pige, whoever she was, flowers the next time they met, or if he should wait before he did that.

This was a first.

Maybe he really liked this girl.

"You should ask Peg," Bull said at last.


Peg was a girl Tramp had been with in the past, and possibly the only close female friend he actually had. She was clever, but she still worked in a boutique. Peg had thick, white-blonde hair, half-lidded blue eyes and a sweet voice. She was also part of a fairly new trend called the flappers, a trend which was growing as young women became more independent.

Much to Tramp's dismay, this had meant cutting her long, beautiful hair short, although on the plus side flappers tended to wear skirts which reached their knees, rather than their ankles, and were generally quite liberal and rebellious, wanting to have fun while they were still young.

Peg was standing outside the boutique where she worked, smoking a cigarette while she took a short break, when she spotted Tramp approaching. "Hiya, handsome," she said, winking. "What brings you here? Come to try on a dress?"

Tramp rolled his eyes at her. "I need some advice."

"You?"

"Crazy as it sounds. Listen…" Tramp told her all about a girl he'd met, a beauty from the upper class side of town who he'd met when Champ and the girl's dog had accidentally tied them together. He explained that he didn't know if he should do anything for her, didn't know anything about her, except that her name was Lady and she'd agreed to see him again.

"Lady?" Peg asked slowly. "Brown hair, brown eyes, and the dog is a little golden cocker that goes everywhere with her?"

Tramp's eyes lit up. "That's her! You've seen her?"

"Yeah, Lady Brown. Her mother comes into the shop sometimes," Peg explained. "You really want my help, don't you?"

Tramp nodded, and Peg studied him carefully. She still liked Tramp – but then again, everybody did; he was just so likeable – and she wanted to help him, but she didn't know if she should. Not if Tramp was just gonna set up Lady Brown for a fall. She'd never really talked to the girl, but she was sweet, and Peg liked her.

So did Tramp, apparently. He seemed desperate, and sincere. "Alright," Peg sighed, "I gotta go back in now. Show up during my lunch break and I'll help you out."

Tramp hugged Peg in appreciation and he and Champ trotted off to find a way to pass the time until then. Peg turned to go back in, her brain working quickly. Elizabeth and Lady Brown had an appointment in the boutique any minute. Maybe she could talk to Lady about Tramp and figure out some way to help.

"Mind if I take the Browns?" Peg asked her boss, who agreed. A few minutes later, the women in question turned up, and Peg went up to greet them, telling them she'd take care of Lady today.

"We're after a gown," Elizabeth – Lady's mother – told her, "for the debutante ball tonight."

"Any particular colour?" Peg asked.

"Blue," Lady said immediately, "to match my new necklace, please."

Peg nodded and led her to where the blue gowns were kept. "Beautiful necklace," she said.

"Thank you. It's my birthday present," Lady replied, blushing slightly. Kid must not be used to compliments, Peg thought. They began to go through the gowns, Peg holding them up against Lady to see which ones suited her, and Peg decided she could ask about Tramp. Elizabeth wasn't there to overhear, after all.

"Friend of mine says he knows you," she said casually, placing a hideous dress (one which even Lady would struggle to make beautiful. Why did they even have something like that in stock, anyway?) back on the rail.

"Oh, I doubt it," Lady said. "I don't really know anyone who…"

"Who isn't upper class? No shame in it, dearie," Peg said, holding up a much nicer dress, which she draped over one arm so Lady could try it on. "You must have an easier life than the rest of us."

Lady looked down, unsure how to answer. Peg decided to get off the subject and back on track.

"This guy says he met you today," she added. "Goes by the street name Tramp. Dark hair, blue eyes, about this tall, scruffy but a real looker. Sound familiar?"

Lady's eyes had snapped back up at the name 'Tramp', and she was smiling now, as Peg draped another gown over her arm. "Yes," she said, "we did meet today."

Peg smiled knowingly, trying not to look sad or patronising, when she saw the look in Lady's eye. She'd seen it before, and this was why she wanted to talk to Lady before helping Tramp. She didn't want the poor kid to get hurt. Then again, there was something about the way Tramp had looked when he was talking about Lady; something different to the look on his face before. The expression from all those other times was a look Peg and Tramp's other friends were used to, having seen it so many times before. They would all know something was off this time.

"Let's go try these on," Peg said, leading Lady to the dressing room. As she began helping Lady into the first of the three gowns she'd selected, she said, "What did you think of him?"

"Of who – oh, you mean Tramp?" Lady said. She smiled slightly. "I thought he was… to be honest, I don't know many other people. I'd say he seemed different from the other boys I know, but I only really know two, and they're older than me."

"Oh, he'll be different from your friends, alright," Peg said, not meaning it harshly. "He'll be different from everything you know, I think. I assume you've had a sheltered life, and Tramp… well, he's pretty much always been a street kid."

"I can believe that," said Lady. They paused the conversation as she gave a small twirl and looked herself over in the mirror. Then Peg began to help Lady into the second gown.

"Looking forward to your debutante party?" Peg asked conversationally.

"I think so," Lady said. "But I'll hardly know anybody there, apart from Jock and Trusty – the two gentleman friends I mentioned earlier."

"Well, that's the point of these things," Peg said. "You get to socialise with people your own age. You get forced to do it, but you get to do it."

"I suppose so," Lady said.

They settled on the strapless dress Peg had chosen, which tied at the hip with a sash and almost exactly matched the shade of blue from Lady's necklace.

"It's beautiful," Lady said breathlessly. "Thank you for picking it out for me."

"No problem, dearie," Peg replied, smiling. Lady seemed to have something which seemed to make people like her.

Tramp was a little late turning up to Peg's lunch break, and to say that she wasn't pleased with him was, for once, not an understatement. Today, she was just mildly annoyed.

"I swear," she threatened before Tramp could even greet her, "that if you dare hurt that girl, I'll kill you. That's no exaggeration, Tramp. She's a sweet kid, and to be honest, she deserves better than the likes of you." Peg sighed. "But… she seems to like you, and I said I'd help. Get your butt in here; I need to get you a suit."

Not waiting for him to answer, Peg grabbed him by the collar and dragged him into the boutique.


"That has to be the most beautiful necklace I've ever seen!" a young woman, older than Lady by about a year, gushed. She called the others over to coo and dote over Lady, too.

There were six of them in all: the young woman, a friend of hers, and three people Lady didn't know. They were all older than Lady, apart from one girl who would not be seventeen for another six months, and Lady stuck close to this girl, because they were both on their own and nervous. The girl was called Dorothy, and had golden hair, green eyes and the most adorable freckles.

"How are you feeling?" Dorothy asked. Lady's stomach had twisted with nerves, causing her to feel relatively ill, but she swallowed hard and smiled anyway.

"Terrified," she said honestly. Dorothy nodded

"Me too. I've barely been out of the house before. I just hope the ball doesn't last too long."

"The sooner it begins, the sooner it can finish," Lady said, glancing at the clock again.

It had originally been planned as just Lady's party, of course, but her mother had friends whose daughters were also ready to enter society, and so it became a debutante ball for six young girls. It was being held in the enormous dining hall of a large mansion, although the young ladies were waiting upstairs. They would descend the staircase like something out of a fairytale, one at a time. They would meet and talk to new people, and dance with young men, and hopefully each would find themselves a suitor.

A butler poked his head around the door, said, "We're ready for you now," and left again. All six girls swallowed, then lined up and began to leave the room they were in, shaking hands and wishing each other good luck as though it were the last time they would see one another. The band played beautiful music as they descended the staircase.

A young man was twirling Lady past the windows of the dining hall when her eyes fell upon a flash of white. The man was a good dancer, but he was rather dull, and she had been looking anywhere but at him anyway, because the looks he kept giving her were making her very uncomfortable. When she caught the brief flash of white from outside, while in mid-spin, Lady surprised herself by thinking, That's Peg, isn't it?

The second the song ended, she excused herself and dashed over to the French windows, sneaking outside while nobody was looking.

Peg gave her a proud smile. "You look beautiful, dearie," she sighed happily.

"Thank you," Lady replied. "I feel rather beautiful, too."

Before Lady could ask what Peg was doing here, the door behind her opened and Dorothy stepped part way out. "The party's inside, Lady, although I can understand why you wanted to get away from Robert," she teased. Then her eyes fell on Peg. "Oh… who is…?"

"Dorothy, this is Peg," Lady explained quickly. "I won't be out here too much longer. Could you cover for me?"

Dorothy nodded and re-entered the mansion.

"Cute kid," Peg commented. The knee-length dress she wore had clearly snagged on something as she snuck onto the grounds, but she didn't seem to care too much.

"I suppose," Lady said. "But Peg, whatever are you doing here?"

"Somebody wanted to see you again," Peg said, winking.

At first Lady didn't understand. Then a young man with dark hair and blue eyes stepped out from behind a hedge, and Lady's jaw almost dropped. This couldn't be Tramp, could it? His hair was smoothed back, and he wore a suit. He looked handsome, but Lady couldn't help but feel a little disappointed. The scruffy look had given him a certain charm which he lost when he cleaned up.

"Hiya, Pige," he winked, flashing Lady a toothy grin. "Mind if I have this dance?"

"Not at all," Lady replied, taking his outstretched hand as a new song started. The band was playing loud enough for them to hear it.

"I think I'll give you two kids some privacy," Peg said, sneaking off to who-knew-where.

Tramp took Lady by the hand, placing his other hand gently on her waist, and they began to dance.

"So this is how high society does parties, huh?" Tramp said, half-commenting and half-questioning.

"It must be," Lady replied.

"Must be really exciting."

"Oh, yes," Lady said, hinting at the sarcasm she felt. "Nothing to do but talk, dance and eat. All my favourite pastimes."

"I wouldn't object to that."

"No, I'm sure you wouldn't. But the young man I was just dancing with was a frightful bore. People expect a young woman to find a suitor at these parties, but I just don't know how I'll manage that. The young men n there are just awful."

"Even your two gentleman friends?"

"Oh, they aren't too bad. They've been eating, mostly."

Tramp spun Lady around and smiled. "The best thing to do at parties."

"So far it seems to be," Lady said. Tramp pulled a face.

"You've never been to a party, huh?"

"Not before tonight, no."

"You should check out a real party some time, Pige," Tramp laughed boyishly. "Come see how the lower classes manage."

"I'm sure a person isn't bored stiff by the conversation at any of the parties you'd go to," Lady said teasingly.

"Definitely not," Tramp said. Suddenly he pulled her closer, and Lady was reminded just slightly of how he had held her earlier, when Missy had tied the two of them together. Had it really been the same day? It felt like such a long time ago.

"Is this how you treat all young ladies you've just met?" she asked jokingly.

"Just the special ones," Tramp said, winking again, his grin widening.

For a moment, Lady thought Tramp wanted to kiss her, but then the song ended and her let go of her waist. The two of them took a small step back from one another, their hands lingering before letting go, and Tramp said, "You'd better be going back to your party. Don't wanna be gone for too long, Pige."

As she gazed into Tramp's bright eyes, a thought occurred to Lady that she had enjoyed herself more with Tramp, someone entirely out of her standing in the class system, than she had done with any of the other young men at the ball put together. She offered him a grin of her own.

"Say, Tramp," she said cheekily, "would it be wrong if I asked you to come see me again some time? Or am I too good for a poor little street boy like you?"

Tramp cocked an eyebrow in surprise. "You want to hang out with a couple of dirty little orphaned street boys like me and Champ?" he asked.

"I don't think I would object," Lady replied. "You could take me too one of your parties."

"I'd have to get Peg to teach you the latest dance moves."

"I don't mind. I like Peg."

"Are you sure?" Tramp asked, but Lady would not be dissuaded.

"Of course I am."

"In that case," Tramp said, "I think that's a brilliant idea, Pige."

They grinned at each other for a moment, before Tramp opened the French window, holding the door to allow Lady to get back to her party.