Captain and Crew

"You should get out at least once a week. It's good for your...physiology. I'll look after Blondie. Everybody needs some playtime."

Carly looked bemused. "My physiology? That's okay, Mr. Humphries. I've gotten pretty used to this kind of life. I enjoy looking after Blondie."

"We gotta can the Mr. Humphries shit, all right? You're Carly, I'm Johnson. I appreciate the way you look after the boat, but just let me know if you want to get out of here some evening. There's almost always some fun clubs around these fancy marinas."

"I'm not really a club kinda girl," Carly said. "A girl like Ginger...I wouldn't even know what to do in her world."

"How old are you Carly, if you don't mind me asking."

"No, I don't mind. I'm thirty-four. You?"

"Thirty-three. I'll be too old for Gingers before long."

"Are you kidding? With a boat like this you'll have Gingers hanging around when you're eighty."

"God, I hope not," Johnson said. He took a long sip of his coffee. "Can I confess something to you?"

"Sure," Carly said. She wasn't sure why he wanted too, but she wasn't going to say no to her new boss.

"Ginger...and...all of them...leave me feeling like all I've got is money. These mornings, after they leave, I always feel like an adolescent schoolboy who doesn't have a clue."

It was way more of a personal confession than Carly had expected, but she liked it. It was something a friend would say to another friend. She suddenly realized Johnson was lonely. Should I get into this, she wondered? Should I be talking this personally with Blondie's owner?

"I'm guessing Ginger feels the same way," she said.

"Oh, hell no. She was a dynamo. She could teach the class."

Carly tried to hide her shock. Sex! That's what he's talking about! We really really shouldn't go there!

"I guess we shouldn't be taking about this," Johnson said dejectedly. "I just wish a woman would talk to me about it sometime. They all seem afraid to tell me like it is. I hear nothing but how wonderful I am, and I know it's not true. The money screws up everything. You know, I actually hired a hooker one time to teach me what women like. Sad but true."

"You're right, we shouldn't be talking about this," Carly said, but Johnson's sad eyes drew her in. "What makes you think the women are lying to you?"

"Oh, it's easy to tell. If I hear one more fake orgasm I'm just gonna give it all up."

"Whoa!" Carly said quietly. "Yeah, we definitely shouldn't be talking about this."

"Sorry, Carly," Johnson said dejectedly. "You're easy to talk to, but I don't want to make you uncomfortable."

"I thought about going to school for psychology," Carly said. "It's funny, captaining other people's boats involves a lot of that kind of thing."

"Want to take me on as a patient? I could really use a woman's perspective on this."

"About sex, you mean? I don't know. I'm not even used to calling you by your first name yet."

Johnson smiled. It was a sad smile that melted Carly's heart.

"Let's start with the basics," Johnson said, jumping in before Carly could escape. "Does size matter?"

"Holy shit!" Carly said. "We're doing this? I'm talking about sex with my boss?"

"Oh, shit. I forgot about all that sexual harassment stuff. Yeah, we'll can it if you don't like it. We'll never mention it again."

"No, I don't care about any of that. This doesn't feel like that, not that I've ever experienced it or anything."

Johnson wondered if that was because of Carly's plain looks. She wasn't big, but she wasn't curvy either. Her body looked more like a warship than a yacht.

"So, do you want to help me figure this out, or..."

"Sure, if you want," Carly said. "I mean, I'm no expert or anything."

"You're a woman. That gives you all the expertise in the world."

Carly smiled. She liked that a man thought that, even though she knew it wasn't true.

"So...does size matter?" Johnson asked, smirking just enough to be cute.

"No. I mean...it's nice...but, no, a girl can feel plenty good with average."

Carly wondered if she'd said the wrong thing. What if Johnson was smaller than average, or really tiny?

"Well that's good to hear. So, I guess I've just gotta figure out what to do with it."

Carly chuckled. "You're thirty-three years old, I'm pretty sure you know what to do with it."

"Yeah, well, sometimes I wonder," Johnson said. "Why all the fake orgasms? Do all women do that?"

"I couldn't say. I'm guilty though, on at least a few occasions."

Johnson looked surprised. "Really? Do you remember why? Was the guy just...lousy?"

"Maybe once or twice," Carly said. "You just wanna get it over with, you know? But other times, with a nice guy that you care about, you want him to feel good about all the effort he's putting in, even though he might not be...making it happen."

"Good! This is good!" Johnson said, his face brightening. "Tell me more."

Carly chuckled. "I can't believe we're talking about this!"

"I want all your knowledge. Everything you've wanted to tell a guy, tell me."

"Wow," Carly said. "That would be...kind of fascinating. It sounds too risky, though. We really need to maintain a professional relationship."

"Okay, well, you already work for me. Let's just expand your duties and I'll give you a raise."

"Whoa, no, I could never...I don't think I'm that kind of girl. Sorry."

Johnson looked at her quizzically. "You don't think I mean...I'm not talking about anything, like, hands-on. Is that what you're worried about? I was thinking maybe you could guide me somehow. Teach me. Like a book-learning class."

Carly chuckled again. "I'm not sure how that would work, but we can try it I guess. I sure as heck don't have a curriculum. Are you just going to ask me questions?"

"Would you be okay with that? They may get into some...interesting areas."

"Wow. This is a pretty fascinating first breakfast with the boss! I guess we could. I mean I've always been a go-for-it kind of girl. Let's see what happens."

Johnson smiled. Carly was exactly the kind of friend he'd longed for in his adult life.

Carly smiled too. She always loved it when things got a little wacky, and teaching her boss how to give supermodels orgasms was about as wacky as it gets.

—

Johnson didn't waste any time getting started with his master class in sexuality. Carly had windows to clean and chrome to polish, so Johnson rolled up his sleeves and joined her.

"You don't have to help with this," she said. "The only time I'll need you as crew is when we're underway or docking."

"I'd kind of like to," Johnson said. "It'll help me bond with the big girl."

Carly was sure he meant the boat, but it made her wonder what he thought of her own body. She was big boned and sturdy, a result, she always thought, of her mother's Latvian bloodlines.

"You can work that rail there," she said, handing Johnson a rag and some chrome polish. She thought of making a joke about the fist-around-a-pipe motion that he'd be making with his hand, but decided it was too soon for sexual levity.

"Does it really take half an hour for a woman to orgasm? I read that somewhere."

"Wow!" Carly said. She looked around at the other yachts nearby, deciding they were too far away to hear the conversation. "I guess," she said, looking a little amazed at the topic. "It depends, though. Mood, and build-up, and frame of mind all affect things. It can definitely happen really quick, but that's rare. For me at least. Men can just get there real easy, right?"

"Yeah. We have to fight it off. It's a fun fight, though," he smiled.

"I'll bet! The half-an-hour thing, though, that seems like a really long time. Most guys can't even go that long."

"I don't mean just...cocks and fucking," Johnson said. "Are we going to use the vernacular?"

Carly laughed. "Why not. I guess we're goin' for it."

"So, what I read was, even if it's fingers or cunnilingus, it can take that long."

"Cunnilingus. Yikes, is that right out of a textbook?" Carly asked. "Do people really talk like that? 'Hey Mac, where can a guy get a fellatio around here?' "

Johnson laughed. "So what do you call it?"

"Cunnilingus? I don't know. Oral, I guess. I had a friend who always called it eating. "Did he eat you?" she'd ask. I always though that sounded sort of odd."

"You'd be surprised," Johnson said, stroking the shiny chrome rail with his rag. "Lots of girls say that. Eat me. I always though it was kind of hot."

Judging by the hot flash coursing through Carly's body, she thought so too. It didn't help that a smooth, slippery shaft was sliding through her fist. She put her rag down and turned away, pretending to look at a passing boat while she cooled down.

"So, women...talk dirty to you?" she asked, glancing at Johnson as she got back to work.

"Sometimes. I like it. It doesn't happen too often, really, now that I think about it."

"Do you reciprocate?"

"No. I can't say I'm really comfortable in that area."

"Well there's homework assignment number one," Carly said. "If you want to really get a woman going, do that. Make sure it's in line with her personality though."

"How do I know that?"

"Like if it's a one night stand you mean, and you don't have time to get to know her? You're gonna have to start looking for the signals."

"That's part of my problem," he said. "I already feel like I think too much. That's why I feel like I'm stilted. Too much thinking, not enough instinct."

"Yeah, I get it. So, why not try one thing at a time. A little gentle dirty talk and then some oral. Eat her out," Carley smiled. "But do this...when she starts to react, don't stop. Don't change anything. Speed, pressure...hold it steady. If you stop, even for a few seconds, you'll have to start all over. I'm not saying that's not fun, but if you really want a woman to...cum...it's that steady application of what feels just right to her. It won't take a half-an-hour."

Carly shifted her rag to another section of rail. She was amazed at what she had just said. She'd never discussed the real, honest details about sex with a man before. It was exhilarating, but it still made her wonder if she was putting her job in jeopardy.

Johnson was happy, too. He'd always thought the best part of sex was giving a woman pleasure. He felt a little closer to being able to do it.

"You know, you can have a guy back to your cabin any time," he said, "and feel free to use the bar."

"Oh, thanks. That's nice of you say that, but it probably won't happen much."

"Well, just keep it on mind. Life's short, you know?"

"Will Ginger be back?"

"She's...not...really my type."

"Really? Long legs and perfect bodies aren't your type?" Carly chided.

"You'll probably think this is horribly superficial, but...I couldn't get my fingers through her hair. She had about a half a gallon of gel in there."

"Yeah, I noticed that. I guess even perfect girls have flaws."

"Not my Blondie," Johnson said. "I think I'm falling in love with her."

"You're stroking her like you mean it. She may be your first real orgasm."

"Ha ha!" Johnson laughed. "If this boats a rockin', don't bother knockin'!"

Carly laughed. She was starting to realize she'd lucked into a pretty good job.

—

The sound of footsteps late at night on a seemingly unattended eight-million-dollar yacht wasn't something a good captain could ignore, so Carly put down her romance novel, pulled on her robe and went up on deck. Another pair of impossibly long legs and high heels was clicking along the pristine teak. Carly cringed, making a mental note to suggest shoe removal to Johnson in the morning.

"Welcome aboard, Sir," she said. "I'll turn in now. Enjoy your evening."

"Thank you, Carly," Johnson said.

As Carly walked away she heard him tell his guest that she was the captain he had hired, and that she lived way in the back, down by the engines. Carly smiled, thinking it sounded a bit like a dungeon, nothing like the beautiful bright crew quarters she inhabited. As she curled up with her book again she marveled at how easy it seemed to be for Johnson to pick up stunningly beautiful young women. His clothes, shoes and wristwatch all telegraphed his wealth, she guessed, and his nice smile probably sealed the deal with ease. It was such a different world than the one Carly lived in.

Brittany was a wealthy girl herself. The high heels clicking on the deck were a cool three-thousand dollars, and far from her most expensive pair. She was a trust fund baby, just like Johnson, and lived the life proudly.

Johnson was unconcerned with her status. His mind was on the elusive female orgasm, and had been all night. He felt like a predator when he first started talking to Brittany at the club, but then he realized it was all about pleasure between consenting adults. It clouded his mind the whole evening, though. His desire to put some of Carly's suggestions into practice bordered on obsession.

Brittany could sense his eagerness. It didn't take long for her to strip out of her trendy boutique clothes, but Johnson had his work cut out for him — she was a bit numb from two too many apple martinis.

Brittany was a big fan of sixty-nine, and that's where she landed, head to toe on top of Johnson. His arms wrapped around her slender thighs as he went to work, trying to ignore her sweet, suctioning mouth on his throbbing cock.

"Oh yeah, suck my cock, baby," he said, jumping right into the dirty talk.

Brittany loved the words, and she loved the feel of Johnson's warm breath on her pussy when he said them. She sucked him deep when his mouth engulfed her entire pussy.

Johnson's head was spinning with Carly's suggestions. Speed, pressure, hold it steady. When the woman reacts just hold it steady.

Johnson tried to decipher what was going on, but he didn't have a clue. He was in full sensory overload, no different from every other time he was with a sexy woman. He tried to maintain a rhythm with his tongue, and did a pretty good job of it, but Brittany was in a non-orgasmic happy place, content to feel tingly good as she sucked her new boy-toy to completion.

"Mmmmm," she moaned as she sucked the last drops and swallowed.

Fifteen minutes later they were fucking, Brittany riding cowgirl. Johnson didn't know how to handle that situation. He always thought a woman would be able to make herself cum when she was in control like that, but Brittany just rode, and rode, and rode until Johnson was nearly numb. He enjoyed it, there was no question about that — what guy wouldn't with a stunning, willowy blonde bouncing happily in his boner? But she seemed nowhere near an orgasm. Johnson rolled her. Brittany giggled as he spread her knees on the rumpled sheets for some doggy style.

"I want you to cum for me, baby," he said as he slipped his well-fucked cock back inside her. "Tell me how you like it."

Brittany moaned. "Oh, yeah!" she sighed. "You're so deep!"

Johnson knew he wasn't. He wondered if Carly had fed him a line of bull about size not mattering. The first signs of Brittany faking an orgasm didn't help his confidence.

He tried to maintain his speed, his body slap slap slapping against Brittany's fine little ass. "Tell me how you like it," he said breathlessly.

"Just like that!" she said. "Just like that!...Oh yeah!...Oh yeah!...Oh yeah!..."

Brittany's voice swelled to a lovely crescendo, and Johnson finally gave up. He knew it was a pity orgasm. It was nice, and Brittany was nice, but oh how he longed for the real thing.

—

"Eggs?" Carly asked.

"Yes. Thanks, Carly."

"You don't look so good," Carly said, as she cracked two more eggs in her bowl and started beating them with a whisk.

"Oh, thanks a lot!" Johnson smiled.

"I didn't see your friend leave."

"No. I think she wanted to get home before daylight."

Carly made the breakfast in silence, buttering toast and slicing melon as the eggs cooked. She topped up Johnson's coffee before sitting down with him for the morning meal.

"I want you to listen to something," he said. He took his phone from his pocket, touched the screen a few times and set it on the table. The sound of sex broke the morning silence.

"You recorded her?" Carly said, sounding, and looking, surprised.

Johnson didn't say anything. He felt a bit guilty for doing it, but it seemed like a good tool to help him learn. He and Carly sat quietly, listening to the carnal sounds as they forked eggs into their mouths.

"She faked it," Johnson said. "I know she did."

Carly was stunned. She'd just listened to her boss's body slapping fast and loud into a moaning, seemingly orgasmic woman. She didn't know what to think.

"Maybe not. I mean, she sounds really...happy."

"Well, yeah, I mean...we had fun, but...dammit, why didn't she cum? I mean, I really thought I was onto something, with the things you told me."

"It's probably hardest with...intercourse. Did you try oral?"

"Intercourse? It's called fucking Carly. And yeah, she was really into the sixty-nine. I thought for sure that'd be it. I tried to figure out how she was reacting, like you said, and kept really steady. I thought my tongue was gonna fall right out of my mouth."

"And?"

"She made me cum! I guess I need more practice."

"At least you're thinking about the right things. That's the first step."

"I wish you could be there to guide me. Maybe I should hire a hooker and you can be there."

Carly looked surprised again. "What? No, I don't think that's a good idea. I mean, this is all crazy enough. And I'm far from the expert you think I am."

"You're a woman, Carly. You're underestimating how much more you know about female orgasms than the average man."

"I guess, but Jesus...this seems nuts."

"So what do I do?"

"More of the same. Just be in the moment. Pay attention. You'll get there."

—

Carly couldn't get the sound out of her head. She didn't know why. Sex noises were common in the twenty-first century — on television, in the movies, on the internet. Carly wasn't a big porn watcher, but she did watch the occasional bit of 'art porn', the genre that was supposedly targeted toward women. So she was surprised that the poorly recorded sound of Johnson fucking a rich girl had affected her so much. She just couldn't get it out of her head.

Halfway through the day she found herself in her cabin, shorts around her ankles, panties pushed down a few inches. Her fingers furiously rubbed her clit. It felt otherworldly, but she couldn't make herself cum. She gave up before she hurt herself, smirking disappointedly, wondering if she should have faked it.

—

Johnson went out again that night, feeling like he was on a quest. The woman who latched onto him was older, a real estate lawyer traveling on business.

Nicole was the kind of woman who cut loose when she was out of town, away from her husband and kids. It usually involved dinner on the expense account followed by a dance club. Sweaty dirty dancing was her thing, grinding on strange men late into the night. Every once in a while she'd find herself with company in her hotel room. It didn't happen too often, and rarer still were the times she'd gone home with a man.

She hit it off nicely with Johnson. He was a good dancer, and they both worked up a sweaty lather on each other before one last drink at the bar. That's when Nicole found out about Blondie.

"You live onboard?" she asked.

"I do. I've still got my condo, but it's so much nicer to be on the water."

"Show me," she said.

—

"Ohhhh!...Yeeaahh!..." Nicole exclaimed, wearing nothing but her bra in the dim light. "Fuckin' give it to me!"

She was bent over the chart table in Blondie's pilothouse with Johnson behind her, her body absorbing his thrusts with ass jiggling happiness.