(A/N: Trigger warning: This is based off the times when age didn't really matter and 16 was the age to have consensual sex. If you don't like that please skip this chapter)

-4 Years ago on some random island-

Shanks was laid back up against a tree while drinking some booze and listening to the wind blow when he caught a glimpse of Natasha following Yassop to an area away from the crew. It was no secret that the 16 year old was entranced by the older male. She basically followed him around like a puppy. Not that he was complaining. What man wouldn't want a younger girl taking an interest in him? Shanks being the curious man he was, followed the pair to the area and was greeted with quite the surprising image.

"It's okie babygirl. Lay back and Daddy will take care of you.~" Yassop was in the act of removing his own clothes while Natasha was already naked and nervously watching him. Shanks could tell the girl was terrified from how much she was shaking. Part of him wanted to go over and stop them but another part of him wanted to watch and see what would happen. Yassop gently embraced Natasha and gave her a steamy kiss which she reciprocated.

He then laid her down on the soft grass and spread her legs. Dragging his calloused fingers down her breasts to her virgin pussy. Gathering her wetness on them, he slid his middle finger inside. Natasha gasped out in surprise as she felt the digit being moved around her tight gummy walls. Noticing her positive reaction to his finger, Yassop proceeded with his ring finger that still had his wedding band on it.

The piece of jewelry now being covered in her wetness and it's coldness providing a new feeling that made the girl shudder. Shanks bit his lip watching the two from a good angle where he could observe and not be caught by any of his crew or the two people only a few feet away from him. "Do you think you can take another babygirl? Remember, the more you take, the better you'll be prepared for my cock.~" Natasha nodded at the man's question and spread her legs wider for him.

Yassop smiled and added his index finger. Once all were covered in her slick, Yassop started to finger-fuck Natasha's tight little pussy. The girl whimpered while making eye contact with the older pirate leaning over her with his large hard cock touching her tummy. Suddenly her eyes widened when his fingers brushed up against that spot inside her. Her breath hitched and small moans emanated from her mouth.

Yassop continued to abuse the spot with his fingers while his other hand found her clit and flicked it gently causing Natasha to jump at the sudden jolt of new pleasure that sparked in her body. Smirking, Yassop leaned his head down to attach his mouth to her clit. Natasha's moans started to get louder and her breathing quickening as she felt the knot in her tummy about to burst. Reaching her hands down to tug on Yassop's hair, Natasha squirmed and whined in pleasure.

The man smirked again and hummed while sucking on her clit while also speeding up his fingers hitting her g-spot harder causing Natasha to cum all over his digits. "D-daddy!~" Shanks continued to watch the couple as one of his hands ran down to his pants rubbed over his hard cock. Now pulling away from her pussy, Yassop removed his fingers from her tiny cunt and licked his fingers clean. Natasha whined feeling the loss of his touch.

The older pirate smiled and laughed as her cute pouting face. "No worries Princess. You're getting the main  event now. Are you ready?" Natasha watched as he lined his large cock up with her entrance and felt the fat tip push at it. Breathing deeply, Natasha looked up at Yassop and nodded. The man leaned over the girl once more to slowly push himself inside her. Natasha immediately wrapped her arms around his neck and shut her eyes tightly. She heard rumors of sex hurting for the first time but good God this was excruciating!

It probably wouldn't have hurt as much if Yassop wasn't so damn big. Once the man had filled her up as much as he could go, Natasha loosened her grip a bit. Yassop bit his lip trying to fight the urge to absolutely wreck Natasha's little cunt. Looking down, he saw the twitching and bleeding of her little pussy. "D-daddy?" Yassop snapped out of his trance to see Natasha's cute blushing face. "Y-you can move now." Hearing this, The man proceeded to do only slow and gentle thrusts. Wanting Natasha to get used to his size and feeling of being filled to the brim.

While this was going on, Shanks was jerking his cock watching the two. The captain desperately trying to stay quiet. God how much he wished it was him fucking her tiny little pussy. His hand followed the pace Yassop kept while fucking Natasha. The girl gripped Yassop's biceps and moaned loudly. Hearing her moans fueled Yassop's ego and caused him to go hard and faster. Natasha's small body rocking along with the thrusts. Her moans getting louder and her grip on Yassop's biceps getting tighter.

Shanks began fisting his cock to the same speed as Yassop's thrusts and blew his load at the same time the two reached their highs. It didn't take long really. Due to all the previous teasing and making out beforehand. The pair both panted heavily and tried to catch their breath while Yassop pulled out of Natasha. His cock being covered in blood and semen. Natasha's pussy wasn't fairing too well either. Still bleeding and pushing out the semen left in her.

"Come on sweetheart. Let's get you cleaned up." Natasha nodded and clung to Yassop as he carried her to the ocean. Leaving Shanks there to plot how he could get Natasha alone for himself.