((Author's notes: This is a story I did for a roleplaying character's profile. She was an original character and needed a background. I didn't elaborate on it as much as I could on her profile and her site. Well I got to thinking what IF….And since everyone insists on elaborating on Will and Elizabeth's backgrounds…let's give ol' Jack one of his own. He's a complex character if you watch him carefully so we're going to explain a little bit of that.. Chelsea and Trynity are the oc's and mine. Other oc's abound since Jack is the only canon here at least for now. The others are basically Disney char's and belong to them. Reviews craved. Thanks!))

Aaah. Morning in the Caribbean at Port Williams.

The sun had been up for a couple of hours now and businesses were opening doors and drawing canopies to protect shoppers and visitors as they wandered down the streets. Carts were pushed out to display wares ranging from fruits to cloth to cooking utensils and tools.

The young man ambling down the way, passed by the fruit market where the round old shop keep waved a hello and tossed an apple at him. The young man grinned and waved back, catching the apple and biting into it. More sunshine was about to cover the Port.

Jack Sparrow, Early 20s and a young man knowing where he was placed in this world. He had his father's narrow looks, dark hair and brown eyes. "Dad" was a world traveler and a privateer who set his son to bed with stories of Singapore, the Virgin Islands and the West Indies. Stories of different cultures and exotic isles and beautiful women, and adventures beyond even the boy's dreams of escape. Mother was a merchant that supplied the residents of the port with the exotic spices, fruits and oils in the Spanish Main from all over that her husband had procured.

Growing up, Jack hadn't wanted for much. But then the boy had everything he could possibly imagine. Not caring for money or who had what personal items, he grew up well aware that life was more than numbers on a pound note. His parents had demanded more and had sent him to the finest tutors that Port William had to offer. Jack studied hard and got amazingly good grades, finishing his schooling when he was 17 years old. He had helped his mum in the shop for the last 5 years but the call of the sea was becoming increasingly harder to ignore.

"That's yer father's blood in ya, Jack," his other had reprimanded one night as they sat at dinner and his father was once more regaling his son with the story of how he had outsmarted a dozen cannibals and escaped with barely his life. Jack had begged his father to take him along next trip but the older man refused. His mother had shot her husband a look as if to say "enough" and had turned to her son.

"Ye'll not be talking of going to sea again, Jack. Ye have a future here in Port. And here's where ye'll be stayin', love."

Jack sighed softly knowing that there was no way while his mum was alive he'd ever be on a ship so the young man resolved himself to a life on land.

But this morning was different.

He had left the shop in his mum's care to take a walk and visit a young lady. Long blonde hair and the deepest brown eyes. She was a lady indeed. In fact she lived in the large house up on the hill. You know the one? Behind the white walls and the large iron gates. The one with the red-coated British guards all around. The one where the Governor of Port Royal lived. No, she wasn't a house servant. She was, in fact the governor's daughter. And she was all Jack could think about. Her laugh was like chimes in the breeze. Her voice was like the soft call of a robin. She was never angry or sour. She always had a smile for him and he couldn't love anyone more. Oh! What's her name? Why it's --

"Chelsea!" he called, rounding the corner of a row of stores and seeing her looking at a cart of material. The girl looked up at his voice and the smile only brightened.

"Jack!"

The two met with a hug and Jack slipped an arm around her as he looked at the cart. "Shopping, are we? I didn't think you even knew what to do with things like that." Always teasing her, and she jabbed an elbow into his side playfully as she ran fingers over a bolt of the lilac silk.

"I have been known to sew, Master Sparrow."

Jack took the jab with a soft grunt and then blinked at her answer. Oooh the options were too close here. Either jibe her some more and risk a harder jab or let it go. What to do what to do?

She fairly answered that question without even looking at him. She moved the lilac and found a bolt of yellow butter cream under it. A smile at her find but to him, she said, "Say it and you will find yourself walking alone on the beach after this, sir." Not a look. Not a hint she knew he had been toiling over the idea at all.

Jack smirked and shook his head, a quiet, "You know me far too well, milady. Then no. I will decide against tormenting you further as I would so miss your company on the beach not to mention I would look rather foolish walking and talking to myself."

Chelsea laughed softly and motioned to the merchant that she would take the whole bolt and then turned and led the young man away from the shops towards said beach. She loved him more than anything and would give anything for him. He was the one person in port she trusted and always would.

Which was going to make what she had to tell him devastate them both.

"Jack...we have to talk."

But Jack wasn't ready for 'serious'. And without a word, he bounced away from her and into the shallows of the waves, kicking up some water and a snort at her. "We'll talk later! Now let's just revel in the fact we have all night together! Well...most of the night. Come on, Chel!" And he turned and ran down the beach, stopping about 30 yards away and opening his arms. "Come on, slowpoke! Why so hesitant tonight?"

Chelsea sighed and shook her head, but a small smirk did creep across her lips. He was so sweet. "Jack!! Please!!" And she lifted the hem of her skirts and loped along after him, finally catching up only to have him steal a small peck on the cheek and then watch him whirl and dash away again. "Jaaaaack!!"

But he wasn't listening. In fact he was actually working up the courage for what he actually wanted to see her about today. But she wasn't playing 'right'. So he'd jerk the odds back to his favor! He bounced along backwards in the surf for a moment a full 40 yards away, a wicked smirk and suddenly he fell in a heap.

Chelsea squealed and ran full throttle for him. "Jack!!" Mumbling all the way about men and their idiotic tendencies to show off and inevitably get hurt. Now SHE was at fault because he was showing off for her. MEN. And she was panting as she dropped to her knees in the sand beside him, the shallow waves washing around them both. "Jack! Please...what happened!? Please! Talk to me, sweetheart. Jack...?" and along with the pleading of course went the proverbial hand on his cheek, fingers brushing through his unruly dark hair to brush it away from his face.

Jack cracked one eye open a sliver just enough to see the worry on her face and then a low moan with a mumble, barely actually lips moving to form silent words.

Chelsea frowned and bit her lip for a moment. "J-Jack...love...wha-what is it? What are...Jack??"

A bit louder at the mumble but still no way she could make anything out.

She sighed and shook her head slightly. "I can't h-hear you. What is it you're trying to...Jack? What is it?" And she leaned down closer, putting her ear to his lips to hear what he was saying.

"Marry me."

Blink.

And he slipped one hand behind her neck and pulled her down to place a kiss to her cheek again. "Miss Chelsea. Would you do the honor of marrying this mere merchant?"

Chelsea pulled away but only for a moment to stare at him. And when she got her breath back, she pounced on him, wrapping her arms around his neck, hugging him tight and giving him a chaste kiss, but still...a kiss nonetheless. When she pulled back a moment later, a breathy whisper into his ear, "Yes!! I will. I love you, Jack! More than anything!"

Jack hugged her for a minute more and finally he got to his feet and a sideways look at her. "What did you have to talk about, love?"

Chelsea suddenly felt a knife in her heart but after a moment of thought, the dagger was removed and the smile was back and she shook her head and waved it off. "Nothing, darling. It wasn't important." Jack smiled again and one arm slid around her waist as they headed on down the beach, just being silent for a while and listening to the sounds of the ocean and the gulls.

When Chelsea walked into the mansion that afternoon, she headed for the study where she knew her father was. Even though she had promised Jack she wouldn't say anything before the young man had a chance to announce the engagement, she was met with a single question when she stood in the doorway.

"So I assume you did what I told you and we'll no longer hear of Jack Sparrow's name around this house?"

Chelsea studied her father for a moment as he sat, back to her, in his chair at the desk. The soft scratching of the quill stopped and he sat back, looking up but out the window rather than at his daughter.

He was an old man who had old ideas. Her mother had died when she was 10 but the way Chelsea saw it was that the woman had escaped the Hell on earth that this existence only had to offer. Forced into a loveless marriage by her father to the Governor who was merely a soldier then. There was never any contact between the pair except for the union that produced Chelsea and the entire time she saw her parents together. She never once heard a term of endearment or a kind word. Rather it was always "sir' or "governor".

She didn't lie to him. But she didn't answer, either. And without a word, she turned and left the study and headed up the stairs and into her room.

This was going to be a long night...