(A/N: Okay, this is the chapter that is making me change this story to Mature. A bit of a warning, it gets a bit sexually explicit at the end and the undertones of it are a bit creepy and somewhat triggering. The characters introduced before the explicit stuff will be sort of important later on in the story, so I wouldn't suggest skipping the whole chapter, but if you want to stop reading when it begins after the last scene break, I completely understand! Hope you enjoy!)

Jack and Anne had been together for a couple weeks now and though Jack hated to admit it, he felt like he was in love. They always tried to see each other often if not everyday. They took strolls around town and down the shores of the beaches together, and he brought Anne down to some of the abandoned dungeons and other secret inlets of the island he had never shown to anyone before her. Sometimes she would sneak little gifts through his window even though his bedchamber was stories above ground. He would spend longer hours on chores for some extra pocket money to return the favor as well.

Being young and in love was confusing, even to the one who was famous for being flirtatious and earned great nicknames at parties such as "Magic Fingers Sparrow", and who also "supposedly" drunkenly slept with four brothel girls on his birthday. Even though the last didn't happen, though to his knowledge it did, he felt like a legend. Still...It was his first real relationship and he didn't know what to do.

Speaking of the brothel girls, Jack sat on the couch in the brothel looking to seek help while Teague was doing his usual business upstairs with Lavina. Though the madams had given Jack tips and tricks throughout the years, and many of them proved to be greatly useful, this was the first time Jack had intentionally sought out advice on a more...serious level. Being in a relationship now, he knew he would find himself doing this often.

"Ladies...even though I hate 'the talk', and I'd hate to admit it, but old Jack Sparrow here needs...help," Jack admitted in defeat.

The three madams, Donna, Abigail, and Claire all looked at each other. Claire was the first to speak up.

"Awwww!" she cooed, sitting next to Jack pinching his bright red cheeks, "Jacky-wacky needs our help!"

"Yes, yes. Don't need to rub it in, lassie," Jack lightly pushed Claire off of him.

"What is it that you need our help with, Jack?" Donna asked, kneeling down to his eye level.

"Well, Anne and I have been going out for a couple weeks now, and that's great and all,...but...she invited me over to her house...to sleep over," Jack stated in a slow and serious tone.

All three of the girls gasped. "SLEEPOVER?!"

"Um, yes?"

"Alright, so, you know when a girl asks you to come over to her house to sleep over, it means she wants you in bed with her," Abigail lectured.

"YES, I know! And that's why I came here! I've been stressing out about it ever since she invited me!" Jack cried out a little too loudly.

"Who knows? It may just be an innocent little sleepover," Donna suggested. "But if it does ever happen, just remember what we taught you. It's all about her. Keep it at her pace and make her feel good and you'll do alright. You did great when you did it on your birthday—"

Claire interrupted, "But didn't Te—" Abigail elbowed her side, a little too close to the breast.

Donna glared at Claire who smiled sheepishly, and she turned back to Jack and continued. "Just relax and don't stress out about it too much, aye?"

Jack took a deep breath and gave one of his famous smirks. "I'm ready!"

Jack wandered in the dark through the streets of Shipwreck City. Asher and the rest of the boys had stopped him in his tracks and started a fight, causing Jack lose the map Anne had drawn out for him. He did his best to remember what the map had shown. It had already been a couple hours later than the time he was asked to arrive.

Oh great, he thought. My first time being invited to a lass's house and I'm hours late!

Jack finally arrived to what he thought was her house. He cleared his throat and knocked on the door. Everything was silent for a minute, and then the door creaked open. Anne's face peeked through the door and Jack smiled with relief knowing he had found the right place.

"Jack, you here!" Anne exclaimed, opening the door all the way. "You're hours late! What happened?"

Jack was surprised, yet happy the girl didn't seem angry with him. She seemed more confused and worried if anything.

"Ah, yes—well," Jack stammered, rubbing the scrape on his cheek from the fight. "Flotsam and jetsam, you know. Things happened and I kind of lost the map. But I'm here! Aren't I?"

Anne giggled and pulled him in. Jack expected there to be flowers and lace, and other girly things, but to his surprise, at the same time not too surprising being in Shipwreck Cove after all, it seemed like a dump. Nothing more than a little shack. He didn't expect a girl as proper as she was to live here.

Also to his surprise, two other people were sitting on the couch in front of him. One was a disheveled young man, a few years older than him, and probably Anne too. He had long, messy dark brown hair and a rather gaunt face. His body was slim, but definitely not as scrawny as Jack's. He had dull gray eyes that stared at Jack while he smoked from a pipe. The girl next to him was a bit shorter and had long dirty blonde hair. She looked to have a similar build to Anne, but a bit skinnier. Jack was comforted to know he wasn't going to be alone tonight.

"Jack, these are my housemates, Luke and Eleanor," Anne introduced. "Luke and I were runaways. Not together—he came before me, but Eleanor took him, then me in and we've been quite the team!"

"So you're the laddie yer Anne has been talking about!" Luke said, extending his hand out, in which Jack took.

Jack smirked and glanced at Anne. "So you talk about me to your friends?"

"Ah—err, yes! Good things!" Anne blushed. "Go ahead and take a seat on the couch."

Luke scooted off the couch onto the floor and Eleanor scooted to where Luke sat. Jack promptly sat on the couch. He looked over to Eleanor, who had yet to say a word.

"Err, hello there, lass," Jack greeted. She didn't respond.

"She's a mute, mate," Luke responded.

"Ah," Jack looked down to the small table in front of the couch.

On the table had cards, rum bottles, and tiny little pots filled with ash scattered across. Luke began to gather all the cards together. Anne disappeared and came back with a plate of cookies.

"Who wants...cookies?" Anne announced as she placed the plate onto the table. She then sat on the floor next to the couch where Jack was sitting.

Anne and her friends each took a cookie. Jack stared at the cookies hesitantly, weirded out by the way she said cookies. He mentally shrugged it off and took a couple.

They began to play Tortuga Hold'em Poker. Throughout the game, Jack became thirsty. He didn't want to get up to look for (probably unclean) water, so he looked at the rum bottles on the table in front of him. It may not quench his thirst completely, but it'll help him relax and keep his mind off things. He took one of the bottles from the table, which was surprisingly still at least half full. He was about to put the bottle to his lips when he felt something on his arm that stopped him. He looked over to see it was Anne who had grabbed his arm.

"Are you sure you want to drink that rum after those cookies?" Anne asked.

"Yes,...and?"

"I wouldn't do that if I were you," she warned.

"Pfft! I'll be fine! I'm a big boy!" Jack insisted.

"Okay, fine. Go ahead then if you know what you're doing," Anne let go of his arm and looked back down at her cards.

Jack gave her a weird look for a second and looked at the bottle. He shrugged and took a couple big swigs of rum. He loved the burn as it ran down his throat. He put the bottle back down on the table and continued playing.

After a while as they played, Jack's ability to see his cards decreased as his vision began to grow more and more blurry. He slowly lost his ability to keep his head up and he began to hold his head up with his chin sitting on top of his hand. He knew he was supposed to be drunk after having the rum, but he felt stranger than drunk.

Everything went black, and after a few seconds, he came to to someone calling his name.

"Jack! Jack! It's your turn! Are you okay?" Anne called out waving her hand in front of his face.

"Wait...what are we—" Jack stopped and realized where he was and what he was doing. "Oh, right."

"I told you not to drink that rum after those cookies," Anne scolded. She breathed a sigh of frustration and shook her head.

"W-what was in that rum?" Jack faltered, his speech slurring as he spoke.

"Ye mean what was in those cookies," another voice joined in. It took a few seconds for Jack to realize it was Luke when he slowly turned his head towards him, still keeping his head up with his hand.

"Nice job, Anne!" Luke remarked. "You made yer mate crossfaded!"

Eleanor tried clapping her hands in front of Jack's face, but failed to get a response out of him. Jack barely even noticed there was anything directly in front of his face.

"Ugh! I thought he was going to have one or the other, not both!" Anne defended. "I'm going to get him water."

Anne went to the back to get water. Eleanor rubbed Jack's back as Luke tried to wave his hand in front of his face. He blacked out again for a few seconds and came to when the door started loudly banging. Through his blurry vision, he could see the two in front of him gasp at the banging. With the tankard of water in her hand, Anne slowly walked to the door and opened it.

The lanterns inside revealed a big, burley man. Still a bit young looking, but he was a whole head taller than Jack and his body was packed with muscle. The man pushed Anne out of the way and slowly made his way towards Jack. He plowed through everything in his way, even throwing the little table they were playing poker on to the side. Luke had a look of concern, but still smoked away at his pipe. Eleanor looked especially frightened.

Jack slowly looked up at the man who stood right in front of him. His head lagged as he tried to process what was happening. He then stood up and put his hand out.

"Hello there! Jack Sparrow. Nice to meet you, mate," he felt he sounded loud and confident like his usual self, but in the state he was in, it was probably no more than a murmur. The last thing he saw was a fist coming right toward his face before everything went black again.

Jack woke up again on the couch. The left side of his face felt numb at first as a single tear rolled down his cheek in shock, then the pain slowly started to sink in. He saw three figures looking down at him through his still blurry vision. Still drugged and drunken up, it took a minute to realize where he was and what had happened.

One of the three figures, Anne, was dabbing blood off his face with a wet handkerchief in panic. Eleanor had a horrified and angry expression on her face, nearly panicking as well even though she was still mute. She rocked back and forth and rubbed her hands together in aggravation.

Luke blew a puff of smoke in Jack's face. "You were one lucky lad to come out of this one alive. The man is known for putting people to their deaths with the punches he gives."

"That was Eleanor's brother, and he's well...very protective," Anne explained. "He spied on us through the window, and with you sitting next to her, he thought you two were 'together.'"

"Oh, you should've seen his face when he realized it was Anne screaming at him and beating him up and not his sister," Luke laughed. "He was so scared! Especially when she picked him up and threw him out the door!"

Jack's jaw dropped as he stared at Anne. There was no way someone like Anne could beat up and throw out such a big burly man!

The room began to spin and he felt something come up his throat. "Ughh, I think I'm gonna puke..." Jack croaked.

Anne sprang up and ran around quickly looking through the cabinets. Just as she found an empty bowl and shoved it into Jack's face, he quickly threw up in the bowl.

The girl pulled Jack up, pulling his arm around her shoulders, and carefully walked him to the back of a hall into one of the bedrooms. She then stripped him down to only his shirt and drawers and laid him down on the bed, where she changed and laid down next to him.

A while after Jack fell asleep, he was in the middle of a dream when he couldn't help but feel good. Too good...down there... His body was still paralyzed so he couldn't move or open his eyes. He thought he was having one of those sleep paralysis episodes where a creature would sit on his chest, but this was one of those creatures doing other things...below his waist.

He managed to wiggle his toes and he was suddenly able to finally move his body. He looked down to see something on top of him under the blanket. Jack carefully pulled the blanket off of himself and adjusted his blurry vision. To his shock and horror, it wasn't one of those sleep paralysis creatures down there. It was Anne!

Anne sat on top of his legs with her head near his hips, and his lenght fully in her mouth. His eyes went wide as she proceeded to slowly move up and down.

He gasped so loudly, he almost screamed. Terrified, he quickly pulled himself away from her and shuffled backwards to the headboard. He curled his legs together toward his chest and pulled the blanket on top of himself.

"What in the bloody hell are you doing?" Jack hissed. "Have you ever heard of a thing called—well, I don't know...CONSENT?!"

"I just thought I would make you feel...good," Anne said, starting to slowly crawl towards him.

"I...I lied! I lied about my age! I'm not twenty-three, I just turned sixteen!" Jack confessed, remembering he lied about his age on their first date.

Anne stopped and her eyes widened, fluttering open and closed. Jack expected her to be angry at him for lying, but she then smiled wide. An almost sinister smile that made his skin crawl.

"Even better..." Anne said, continuing to slowly crawl to him. She pulled the blanket off and sat on top of him.

"A-Are you...drunk?" he whimpered. Jack's voice went from shocked to nervous.

With her hand, Anne shoved her boyfriend's lenght into herself. Jack gasped. It somehow felt so...good. He was blacked out when he thought he did it with the madams at the brothel, so he didn't know what to expect. Anne slowly started to move up and down. Jack couldn't help but close his eyes and moan a little...