A/N: Forgive me...this has got to be the naughtiest thing I've ever wrote...but it would not leave my mind. It's working under the asumption I have that Bootstrap won't survive the third movie...

Mr. Turner's Last Night as a Bachelor

ONESHOT! DON'T OWN A THING. POST POTC3

The night before Will finally marries Elizabeth, he asks Jack to explain to him...the birds and the bees...

Will couldn't stop thinking about his father. He really hadn't stopped thinking about Bootstrap Bill since they returned from their recent adventurers. Now Jack finally had his Pearl and his freedom, and tomorrow Will would have Elizabeth...as his wife.

They were docked in Tortuga harbor. Elizabeth was fast asleep in Jack's cabin, Jack taking a hammock with the crew. But Will could not sleep. He was nervous, anxious and a little bit scared. He had just faced un-dead pirates, Davy Jones, dark magic, and the EIC, but the notion of failing one woman terrified him. They had been through so much together in the last two years...but one thing still eluded him. And it was embarrassing.

As if on cue, Captain Jack Sparrow swaggered on deck, a bottle of rum in hand. It was then Will got the craziest idea. Jack came to his side and said to him, handing off the rum,

"William! There you are! Thought we'd partake in a toast to your upcoming nuptials!" Will smiled at him and pulled out the cork,

"Thanks Jack..." To Jack's surprise, Will upended the bottle and took a few good long swallows. Raising his bushy black eyebrow, Jack quipped dryly,

"Least one of you two learned not to waste good rum..." Will took the bottle from his lips, and glupped down the cool but burning liquid,

"I just realized I need to talk to you about something and I needed an extra bit of liquid courage."

"Talk to me? Didn't we square that business with the kiss and Elizabeth?" Jack asked slightly afraid.

"We did...but...Jack...my father is gone for good...Gone before I could ask him..." Will started. Jack rolled his eyes and laughed,

"Come on Will! Out with it!" Will looked Jack straight in the eye and said,

"Before I could ask him how a man and woman...spend their wedding night together." Jack's eyes were wide, stunned really. Finally he nodded and smiled nervously before licking his lips and saying not looking Will in the eye,

"Ah! Oh...um...Didn't...Shouldn't you have already had this little talk with your former master, the blacksmith?"

"Mr. Brown? No...he was too drunk to even teach me smithing let alone try to mentor me at anything else." Will replied. Jack threw up his hands and muttered,

"Oh course! Why make my life easy?" Jack thought a minute or two, casting annoyed glances at Will, before smiling and snapping his fingers. He pointed to Will and asked,

"What about your future father-in-law, eh? After all you've been through all this business once before last year with weddings and all. Surely he sat you down and..."

"Governor Swann? Jack, the man could barely make small talk with me. Can you imagine him trying to tell me how to ...you know...with his daughter?" Will asked with a laugh. Jack drummed his fingers on the Pearl's railing,

"Aye I can...that can't be normal..."

"Jack...you were good friends with my father...I consider you my best friend. And even though we've had a confusing and mistrustful relationship along the way, I know I only want the man I respect and look up to more in this life to explain to me how to be a man...and all it involves." Will said sincerely. Jack looked blankly at Will a second before asking,

"How close were you with Norrington?"

"Jack..." groaned Will. Jack held up his hands in placation,

"Okay, okay, you win! I give...(sigh!) Come over here..." Jack led Will to where two short crates sat on the deck waiting to be taken down to the hold. They settled down, Jack with his hands on his knees trying to find a proper place to begin. Then he nodded his head to the side and asked Will,

"So how much about the sacred act itself DO you know about?" Will tried to look informed and worldly, as if he knew what he spoke of,

"Well...I know it involves a bed...taking...one's...clothes off...kissing...holding..."

"You have no ruddy clue do you?" Jack asked dryly. Will winced and replied,

"Not really no..." Jack nodded,

"Ah! Of course..." Jack thought a few moments more. Then he nodded to himself and turned slightly to address Will, "Will...half of the act itself...is intinct really, it will come naturally."

"Really? What if I screw up?" asked Will.

"You sure you don't want to talk to Gibbs? 'CauseI can go down and fetch him if you..." Jack started thumbing towards the ladder leading down to the lower decks.

"Jack..."

"Okay, alright...first...you take your...um...hey...ohh...and then you...move your...Ahh-hemm!...And then you..."Jack stopped scolding himself for not getting the words out. He should have done this ten minutes ago without hesitation. After all, he was Captain Jack Sparrow. Ladies loved him...and slapped him...But looking at his young friend's expectant face, he knew now was not the time for bad jokes and stories about one night stands. The lad was about to marry and he was looking for the real thing, not the substitution. Jack wished at times he was in his boots. Suddenly, the answer came to him,

"You and Elizabeth have used your tongues when kissing, yes?"

"Yes...recently..." Will admitted with a slight blush. Jack smiled knowingly and told him,

"Same concept...different body parts. Savvy?" Will nodded with realization,

"Oh..." Then he furrowed his brow and asked, "But...what about..." He leaned in and whispered in his friend's ear. Jack's eyes drew together in confusion. He leaned back when Will pulled away and asked ,

"You can do that?"