Anna was done with the life she knew. The normal, steady, unending sameness of it all. Locked within the confines of her Father's estates, the only time she ever left it was when she snuck down into the library and curled into the corner with a book. Those were the highlights of her life, experiencing anything close to the adventures her favorite characters went through was always her greatest dream.
The day of her 19th birthday she finally decided she was done. At the very tick of midnight, having spent the last hour staring impatiently at the hanging clock in her rooms, she jolted up, a burst of energy running through her. This was it, the moment she had been preparing for. She quickly opened her door, smoothly closing it behind her, doing her best to be as quiet as possible. Unable to contain the nervous energy, she sprints down the hallway, hoping her planned distraction would hold everyone's attention during her run for freedom.
As she runs through the corridor's of the only place she ever lived, nothing but the sound of her own heavy breathing in her ears, she finally catches sight of her exit. She slows slightly as she reaches into her pocket, grabbing the key and slamming it into the door, unlocking and opening it haphazardly, adrenaline pumping through her veins. Not bothering to lock it behind her, she drops the key on the floor, taking a second to breath before sprinting one last time.
A feeling of exultation rises within her as the gates get closer to her, running to the spot she spent many weeks working on setting up. She had dug a slight indention into the dirt, just big enough to allow her to wiggle under the gap in the gate, but, she hoped, not a big enough indent for anyone to have noticed. As she forces herself through the hole, her breath catches for a second when she feels a piece of her pants fabric catch on the metal, but it cleanly tears off without touching her skin, and she gets out, stepping outside the property for the first time in her life. Feeling more excited then she could ever put into words, she runs toward her destination, the docks.
Her goal was to manage to join a pirate crew. Quiet voices in the back of her mind told her she was crazy for randomly joining pirates, as all the information she had about them told her they were ruthless, lawless, barbarians, but that was part of the allure. All her life had been orderly, she wanted to live dangerously.
Banishing the voices, she finally reaches the docks, she walks as steadily as she can, keeping as tight a rein on her excitement as she can. She had felt the wind against the bare skin of her ass, after the gate had ripped through the fabric. But she hoped she could use that to her advantage. Slowly approaching the docks, she catches the eyes of a unknown man aboard one of the boats. She beckons to him, forcing her doubt down, acting as confident as she can.
The unknown man makes his way over to her, pushing his way through all the people crowding around the ships. As he gets closer she starts to get intimidated by his size, the massive man wearing a open shirt leaving nothing to the imagination. Forcing herself to keep her mind on the business at hand, she straightens her back, taking a final deep breath before looking the man in the eye.
The man doesn't bother with small talk, leaning his head to her ear, "What did you want?" He mutters, his breath hot against her face.
"Your crew recruiting?" She responds simply, lifting her chin and trying to get eye contact.
"What do you bring to the table?" He responds without missing a beat.
Taking a deep breath, she turns around, her ass rubbing against his crotch, blushing fiercely at herself, forcing herself to remain calm and praying that everything works out as planned.
He doesn't make any visible reaction for a few seconds before he grabs her shoulders roughly, steering her towards an alleyway quickly. She lets him steer her, hoping against hope she doesn't end up regretting her actions.
He quickly finds an abandoned alleyway, pinning her against the wall. "Don't play with me!" He demands, his hand pinning her arm to the wall. She catches a slight bulge in his pants and it relieves her fears of failure... marginally.
"I'm not!" She responds, trying to sound as desperate as possible, easier for her to pull off then she wanted to acknowledge to herself. She gently bucks her hips into him before continuing. "I'd do anything to become a permanent member of your crew!"
"Anything? You mean that literally?"
"Of course!" She responds immediately, trying to be as desirable as possible but not knowing how. "Anything that could possibly be needed!"
"Prove it," He growls into her ear, "Satisfy my urges and I'll make you a permanent member of my crew."
Not believing her ears at so good a deal, she slips her hand down to his pants, his raging boner poking out immediately, desperate for attention. She unbuttons her shirt with her free hand while stroking the tip of his dick with the other. As her breasts flop out, free of their confines, she bucks her body slightly, keeping her large breasts bouncing in his face as she teases the tip of his dick. Not stopping to second guess herself on how all this feels so natural, she slides her hand down his shaft, the throbbing egging her on.
He suddenly takes control, pulling back and grabbing her roughly, bending her over so her ass is exposed to him. Slipping her wet panties aside, he shoves his cock deep into her virgin asshole, not worried about anything but his own pleasure. Pain erupting through Anna's entire body, she collapses against the wall, refusing to fight back as she was willing to do anything for the reward, the reward of the pirate crew. As he thrusts in and out of her, the pain slowly turns into intense pleasure. Desperate moans start to slip out of her lips, the stimulation driving her wild.
He starts to go faster, feeling himself start to get closer to busting inside her asshole, not bothering to tell her how close he was. She starts to get in the motions, moving her hips into his dick as he thrusts, naturally turning into a dick hungry slut. All of a sudden she hears him let out a loud groan as he erupts inside her, shooting extreme amounts of his hot sticky load inside her hole. He pulls out while orgasming, shooting strands of his semen all over her bare back and hair.
She collapses, completely empty of energy, the only thought left in her mind a desperate prayer that he would allow the princess turned desperate slut to be a member of his crew.
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