The half-elf stepped down below deck, finding the captain’s quarters at the rear of the ship. There, she found Des in her rainbow panties and a matching bra. She turned back and adjusted her glasses upon seeing Gwyn there.
”I’m glad you’re here, Gwyn,” she said. “I have two important tasks for you.”
”Yes, ma’am! What’s the first one?”
”First, I want you to spank me.” Gwyn blinked. “I have two different types of pirates, those who strike, and those who stay behind to be stricken. I want to see which one you are.”
Gwyn had to blush, but gave it some thought. Then she had a brilliant idea. “How about I spank you first and you spank me afterwards?”
Des stood there vaguely impressed before bending over her captain’s desk. “Well?”
Gwyn didnt need any more encouragement. She gingerly gripped the nerdy captain’s panties and gave a soft tug, gently stretching it and seeing how far it will go. Once they reached her mid-back she let go, grabbing a nearby paddle hanging from the doorknob.
Without any warning, she swung, and it slapped Des’ booty with a loud clap! Des gasped, her eyes shutting in euphoria as the spanking continued. Gwyn didn’t have much experience on the giving end of a spanking, but she certainly wasn’t sloppy about it either. Within ten minutes, the pirate leader had an ass as red as her newest recruit’s. She stood up slowly, rubbing over her stinging behind and taking the paddle from Gwyn moaning lowly.
”Your booty’s plenty paddled already, so I’ll try and go easy on you,” said Des cheekily.
Gwyn couldn’t help but squeal from the first of these “easy” spanks, her rosy red rump jiggling from each smack of the paddle. They both different definitions of easy since Des slowly and methodically sent a hard smack of the paddle onto her jiggling behind.
Her red rear was just starting to fade but now returned in force, the color of cherries almost. Tears were springing from Gwyn’s eyes but she couldn’t deny the pleasure she was getting from this. She didn’t know how long she had been paddled for, but felt it wasn’t long enough once it was done.
”That felt pretty good,” she sighed, not leaning back up. “So, my... my next assignment?”
”We’re going to intercept a Wu-Qen ship bringing in gold this evening,” she said. “Wanna help us raid it?”
The half-elf thought it through, deciding that such swashbuckling adventure would befit her new life as a pirate. And if they lost? Well not much of a big deal to her. “Alright let’s do it!” she exclaimed excitedly, causing Des to chuckle at her enthusiasm.
“Alright we strike tomorrow, best get a good night’s rest Gwyn but don’t forget to acquaint yourself with the rest of the crew. You’ll be with Frolin’s crew.”
Gwyn nodded and left, opening the doors to the rest of the deck. She swiftly found Frolin by the bow smacking the rump of another half-elf, this one sporting purple hair and a green bra and granny panties. The princess turned and waved to Gwyn.
”Hey, Des tells me I’ll be working with you tomorrow,” she said.
”It’ll be a pleasure having your company, Gwyn! This here is Croc, named as such for the crocodile tears she used to spill during her spankings.”
”I-I never cried!” the half-elf, Croc, tried protesting. “Maybe I teared up a little, but no crying!”
The next few smacks sent her way caused the half elf to squeak and indeed her tears did come but she held in her cries. Huffing Frolin let her up, the half elf quickly escaping down below the decks rubbing her rear.
“Huh guess she got tougher, how about you Gwyn? Care for a spanking?” Gwyn shyly shook her head,
“Not this time Frolin, I think i had enough for today.” Gwyn turned around and showcased her still red rear. Nodding Frolin snorted before slapping her rump, causing the half elf to yelp in surprise.
Gwyn found an open room, setting her bag down and stripping to her undies for bed. She gave a little shriek as she was hoisted into the air by her undies, finding that an Orc was holding her waistband.
”The name’s Groll,” she greeted. “This is usually where I sleep.” She then laughed and hung Gwyn’s panties from a coat hook. “But it’s okay if you sleep there for tonight.”
Groll then stripped down to her undergarments, a plain black bra and granny panties, then climbed into bed. Gwyn simply swayed around a little, surprised to find herself feeling drowsy despite her wedgie.
Choice 1: Gwyn goes to sleep and the next day begins with the raid.
Choice 2: Gwyn is uneasy during her sleep. Restless she tries to clear her mind walking the deck at night after escaping her wedgie.
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