Eleanor Thrives

Two years passed by more quickly than Eleanor had thought they would, and it could be said that that was so because of how quickly Eleanor ... or, rather, Elliot ... adapted to life as a privateer. She has rather quickly moved up from being a lowly lookout to being one of the most well-respected members of the crew of the Lady of the Deep, as well as developing a new found talent in swordplay.

She had grown close with the rest of the crew, eclectic band though they may have been, and managed to secure the position of boatswain. It hadn't been easy to keep her true gender a secret; she was starting to develop a more womanly figure, and was having to start extensively cover her chest to prevent it from being noticed. But she had managed it, though not without having to endure some teasing from other members of the ship about her shy nature.

Perhaps the part she got most teased about was how she had never visited a brothel while serving on the Lady. Almost all of the men visited brothels when they landed in a city - even the married ones - and her lack of interest had brought her plenty of jeers. Such as those she was receiving now, as she sat in a tavern in Kingston.

"Come on, Elliot! All this time I've known ya, you've never gone to a brothel. You're gonna blow, you keep it pent up!" Wally said, leaning forward across the table.

Eleanor sighed exasperatedly. "I've told you, Wally - and all of you lot!" She gestured to the rest of the crew sitting around her. "I don't need to visit a brothel! I'm perfectly fine!"

"Bullshit!" Terry shouted, which most of the crew echoed.

"Yeah, come on Elliot! You're not some monk, you need to let it out." Wally said.

"Hey, maybe his problem is he doesn't want no woman? Maybe Elliot want a nice man to diddle!" Carver said to a chorus of laughter. "A pretty boy for the pretty boy!"

"Oh, ha ha, Carver," Eleanor said sarcastically. "You're very funny. But do you, of all people, really want to be making comments about diddling men? I mean, we all know about you and Bart ..." That shut Carver up pretty good, and now it was his turn to get the chorus of mocking laughter. "But if you all must really know, I don't need a whore because I've never had a whore, all right? Self control goes -" She didn't get to finish that last sentence before being cut off by exclamations from the crew.

"Elliot Budding's a virgin?" Somebody said, laughing.

"Oh, we can't have that!" Terry said, picking Eleanor up easily and carrying her away, despite her protests. "We are getting you a whore to fuck right now!" he said to cheers, as he carried Eleanor to the local brothel, her trying to squirm out of his grasp the entire time. But she couldn't, and he carried her into a room and dropped her roughly on the bed. "Stay here," he said, leaving the room and closing the door behind him.

"Shit," she muttered to herself, sitting up on the bed and looking around the room. It was dark, only lit by two red hued candles on either side. Silk covered not just the bed, but was also draped across the walls, with a heavy rug on the floor. It was a nice room, but she really didn't want to stay here. She knew Terry would be back with a prostitute, but that would just lead to the possibility of her secret being discovered. But she knew that now the crew wouldn't rest until they got her to sleep with a prostitute.

Eleanor rested her head on her palms, and was deep in thought when the door reopened. Terry didn't come in, though. Instead it was just a woman with dusky skin, dark hair, and dark eyes who sauntered in, smiling at Eleanor seductively. Eleanor was a bit taken back when she saw that the woman was entirely naked, but couldn't help but look her up and down. The woman was full-figured, with large, firm breasts and wide hips ... she was very pretty, all things considered.

Eleanor started to say, "I apologize for wasting your time, but I must go," but she barely got a word out before the woamn started walking over to her and Eleanor's breath caught in her throat.

"How is it," the whore said in a French accent, tracing a finger down the side of Eleanor's face and to her shoulders. "That you are such a pretty man and yet your companions tell me you are still a virgin?"

"I-I-I don't know ..." Eleanor said nervously as the whore slid onto her lap, her big breasts in front of the young privateer's face. "I'm, uh ... I'm Elliot ... by the way ..." she said awkwardly, trying to make small talk.

"Shhh," the whore said, pressing a finger lightly to Eleanor's full lips. "I am Leonie, mon chéri. And I am going to take you to paradise," she said in a low voice, her soft hand stroking Eleanor's cheek and the scent of her perfume, flowery and sweet, filling Eleanor's nostrils. Her hands still on Eleanor's cheeks, Leonie pulled her in close, and kissed her deeply.

It was Eleanor's first kiss, and she let Leonie lead, following her example as the whore slipped her tongue into Eleanor's mouth. Eleanor slowly placed her hands on Leonie's hips, feeling her soft skin, before Leonie guided them up her stomach and to her breasts. The we so large, but they felt amazing in Eleanor's hands. Eleanor had often felt her own, but Leonie's were so much fuller that it was a world a difference.

And then Leonie's fingers were tracing their way down Eleanor's arms, to her flat belly, and then hooking into Eleanor's trousers. Eleanor didn't even think about what that would mean, captivated as she was kissing Leonie and playing with her breasts, until Leonie broke the kiss.

Then Eleanor realized that her hands were fully in her pants. Leonie smirked at the look of worry that crossed Eleanor's face, and the whore asked, "Your name ... it is not really Elliot, is it?"

"No, my name's Eleanor, not Elliot." She paused and took a deep breath. "You have to keep this a secret," Eleanor said forcefully.

Leonie laughed, and Eleanor had to admit that it was one of the most beautiful laughs she had ever heard. "Relax, mon chéri," She said, caressing Eleanor's face gently. "Keeping secrets is my specialty. But now that I know it," she said, standing up and putting her hands on her hips. "You must remove all of these mannish clothes that you are wearing."

Eleanor smiled and obeyed Leonie, stripping of her clothing until she stood naked in front of the prostitute. Leonie purred approvingly, "You are beautiful, mon chéri. Far too beautiful to be hiding this behind the clothing of a man," she said as she moved back in and kissed Eleanor again. Her hand moved between Eleanor's legs as the kissed, and the two fell onto the bed.

Eleanor was already wet by the time Leonie had started playing with her womanhood, and she only got wetter as the whore started to rub her clit in circles, before sliding in one single finger. Leonie broke the kiss and started moving down Eleanor's body, planting kisses all the way down, starting at her neck. She paused at Eleanor's breasts to suck on her hard nipples, squeezing them as she did so, before continuing until her face hovered in front of Eleanor's dripping wet pussy.

She kept pumping one finger in and out as she looked up into Eleanor's eyes, before starting to lick at Eleanor's clit. One lick was all it took to send Eleanor over the edge, making her cum hard, shaking in pleasure ... but while Leonie withdrew her finger, she didn't stop. No, her face was buried in Eleanor's pussy, her lips covered in the younger woman's juices, and she just kept licking and sucking at the sopping wet pussy in front of her.

She kept going and going, for God only knows how long, and Eleanor came many more times. But eventually, Leonie slid back up Eleanor's body, her breasts resting against Eleanor's. The whore kissed her one last time, allowing Eleanor to taste her own juices on Leonie's tongue, before standing up. "I must go now, mon chéri, but please come visit me again some time. I quite enjoyed pleasing you," And with a wink, Leonie was gone.

Eleanor could only lay back on the bed panting, feeling the wetness between her legs and basking in the pleasure she just experienced. Part of her couldn't believe that that had just happened ... she would never have thought that she would lose her virginity to a woman, let alone a whore. But, here she was, laying in bed at a brothel, having just had an orgasm. She couldn't help but think of what her parents would say, and the thought made laugh to herself. She decided she would leave this part out of her next letter to them.

Still chuckling to herself, Eleanor got up and gather her clothes to put them back on. But she had just set them in a pile on the bed when the door suddenly swung open. Eleanor's eyes widened in a mixture of shock and horror as the people walked in and saw her standing naked, most definitely not a man.