Captain and Crew

After a little while Carly needed to break the tension. "She's so petite. I thought you were a leg man."

"Oh," Johnson said. "You're right, she's...not my usual type, I guess."

"Do you...want me to fast-forward?" Carly asked. "Did you want to show me something in particular?"

"No, she's almost done I think," he said, watching the look of ecstasy on his face as Lauren continued with the nice long blowjob.

Carly thought about her own oral skills, or lack thereof, while she watched the cute girl drive Johnson to the brink. Blowjobs had never been Carly's forte. She was okay at it, she thought, but she'd never drawn it out into a long, sensual event the way Lauren was doing. And she'd never had the confidence that a man could get it up again to take things all the way to completion. And then there was the whole cumming in the mouth thing, and the swallowing thing. Carly had never been comfortable with either.

"Is she really good at that, or am I just imagining things," Carly asked, right after Johnson came in Lauren's mouth.

"Really good," Johnson said.

Lauren's giggle rang out through the tinny speaker when Johnson flung her onto the big bed. Her skirt was up and he pulled off her panties with one forceful motion. His mouth went to her pussy and her breathy, staccato moans gave Carly goosebumps.

Based on what she was seeing, Carly wondered why Johnson had any doubts about Lauren. The girl was obviously having a wonderful time, and she seemed plenty sensitive in all the right places. Would a girl like that really fake an orgasm, Carly wondered?

The answer was yes. Lauren went off against Johnson's tongue, looking and sounding beautifully sexy, but Carly had a pretty good feeling it wasn't a real orgasm.

"I think I see what you mean," Carly said.

"Right?" Johnson said. "I get that all the time."

"Maybe...it's your money," Carly said. "I mean, they all know you're a rich guy, right? They probably think if they please you they can be part of your world."

"Maybe."

"Why are you stopping?" Carly asked, critiquing Johnson's actions on the screen. "If you think it's fake you should keep at it. Don't give up. We talked about how it takes time for lots of women."

"Yeah. I guess I wasn't thinking about that. I need to keep that in mind better."

Carly and Johnson watched as the oral session transitioned through a quick strip-down of clothing to some full-on fucking.

"Do you want me to watch this?" Carly asked. She was feeling warm and flush, and a little embarrassed.

"Yeah, there's more. She came like three times. I wasn't sure about any of it."

"Do you need to be?" Carly asked, taking a more psychological approach.

"What do you mean," Johnson asked.

"I'm just wondering why it matters so much. The other night, with Nicole, would you have enjoyed it any more if you'd known she was having real orgasms?"

"Sure. Oh, yeah. Wouldn't you? If you were with a guy and you were doing something to him you thought was really great, something you thought was going to genuinely please him, wouldn't it bother you if he faked a response?"

"Yeah, you're right. It would," Carly said. Her attention focused on Lauren again. The cute girl was on her back with her legs up on Johnson's shoulders. Her tits were gyrating in circles as a good rhythmic fucking rocked the bed. Lauren's vocalizations rose in intensity.

"You're makin' me cum!" she shrieked. "Oh, fuck yeah!"

With that she feigned a meltdown. It was good acting, sexy as hell, but Carly smelled a rat.

"She's good, but, yeah, I see what you mean," Carly said. "I still think you could just go with it though. I mean, she's really sexy, isn't she?"

"Very sexy. But how am I going to have a second date with someone if they're not being truthful with me?"

Carly was astonished. She'd assumed the women were all sexual conquests. Quick pick-ups. She never dreamed Johnson thought of them as dates.

"So this is really important to you," Carly said, giving away her surprise.

Johnson nodded. He didn't know what to say. Things were getting deeply personal.

Carly watched Lauren position herself on her hands and knees. Johnson wasted no time plunging into her, holding her sexy little ass in his hands.

"So, you normally don't see the same woman more than once?" Carly asked.

"No. If I see them again, out at a club or wherever, all I can think about is how I messed up. I'm the guy who couldn't give them an orgasm."

"Wow," Carly said. "That must be...awful. I think you need to start thinking about all of this differently. Nicole, and even Lauren here, they both had lots of fun with you. Just because a woman doesn't have an orgasm doesn't mean she's not having a great time. I told you the other day, I've faked it once in a while. As far as I can remember I still had a great time."

"I don't want to be that guy. The one you had to fake for."

"So, don't give up. After both of Lauren's fakes you just moved on to something else. Remember what I said about persistence? If something you're doing is getting there, as soon as you stop it you need to start all over from scratch. Well, maybe it's not quite that dramatic, but, do you get what I'm saying?"

"Yeah," Johnson said. "I wasn't thinking last night. I dropped the ball."

"You need to get that pressure off of yourself somehow," Carly said. "You're still young, and obviously there's no shortage of women who want to be with you. Relax. You'll get used to the signals women are giving. Don't give up when you see something working. It takes a little time."

"You're awesome, Carly. Thank you so much." Another beautifully acted, sexy as hell fake orgasm ripped out of the monitor's speaker. "I'm surprised you didn't watch this last night. I wouldn't have been able to resist."

"Yeah, well...I thought about it. I'll admit that."

"You know it's okay, right?"Johnson said. "I'll admit something, too — I thought you were watching. I kind of...liked it, that feeling."

Carly's body flushed with heat again. "You did? Is that something you're into?"

"Not that I know of. I mean, this is all new."

"Really! You seem so...relaxed about it."

"That's because of you. I could never sit here and watch this with someone else."

Carly was wondering where things were going. Did Johnson have feelings for her? Was he angling for something physical to go along with her other duties? Her nerves kicked in again and she felt a need to call an end to things.

"Are we done with Lauren?" she asked. "Sorry. That sounded horrible, didn't it."

"You can switch it off. Do you really think she had fun? I hope she did."

"I'm sure of it," Carly said. "I hope you did, too."

"Yeah. I mean, I gotta get over this problem, but yeah, she was great."

"Have patience," Carly said. "Women aren't as complicated as you think. Just...a little different."

—

For the next two days Johnson didn't go out at night. A nice couple stopped by for drinks one night, and the other night he turned in early. Carly fought the temptation to "check in" on him with the security cameras. Her curiosity was powerful, but she knew if she gave in to it she'd have a hard time looking him in the eye the next morning.

The two day respite from her duties as sexual counselor gave her a chance to think about what was going on. It was an odd situation she found herself in, that was for sure. She was glad she was between boyfriends. Carly didn't want a steady man, but she enjoyed a project. Teaching Johnson how women like to be treated and molding him into a skilled lover was a project that seemed worthy, somehow. She wasn't sure why. She wondered if she was deluding herself because the situation was so titillating, but then she remembered the sad look in Johnson's eyes when he talked so honestly about not being able to satisfy a woman. I could show him, Carly thought to herself. We could strip down and go one-on-one, for as many sessions as it takes, until he feels confident. She smiled and shook her head. Yeah, right! And lose my job afterward!

Instead, she broke out her vibrator. She had to wipe the dust off of it — sex just hadn't been on her mind much since she broke up with her most recent boyfriend. After all the talk of faked orgasms she wondered if she'd be able to cum, but the first touch of the buzzing silver tip sent such a jolt through her she knew there was nothing to worry about. It took a few pleasurable minutes, with her mind spinning full of visions of Johnson with Nicole and Lauren. "Damn!" Carly exclaimed, her voice almost all breath as the lovely warm orgasm coursed through her. She breathed deep a few times, pulled up her pants and went back to the engine room for her weekly hydraulic inspection.

Johnson went out the next night, dressed in his 'handsome rich guy' clothes. Two hours later Carly heard the tell-tale clicking of high heeled shoes on deck. She turned on the monitor just in time to see a long legged woman taking them off. Carly was glad Johnson had remembered — high heeled shoes aren't kind to teak decks.

The woman was a stunner. Carly thought she looked similar to Ginger, but with blonde hair and more curves where they counted. Shoes in hand, she took Johnson's arm and he led her into the salon. Carly switched to that camera. It was a first, following Johnson and his guest like a stalker.

She chose to watch in silence. Listening in seemed even more wrong than what she was doing. She was curious what the woman's name was, but it didn't really matter. She watched as Johnson mixed two drinks, and the blonde sprawled out on the couch. It was like a silent movie, and just like in those, Carly had a pretty good idea of what was being said. "This leather is so soft," as the woman ran her hand over the settee cushion. "Do you live here?" as she looked around. "Where do you go? Do you take it to the islands?"

The woman curled her legs against herself and Johnson sat down. He leaned in and kissed her before he handed her a drink. She smiled a pretty smile.

Carly zoomed in. No need to see the whole room, she thought, when she could get a better look at things. The blonde put her drink on the table without taking a sip. It was go time.

Another kiss. Steamy. Hot. Tongues aplenty. The plunging neckline halter top the woman was wearing had ties down the front to hold it closed. Johnson pulled the strings, one at a time as the kiss burned on. A minuscule bra held healthy, natural looking tits, leaving plenty of flesh showing for Johnson to bury his face in.

She wiggled out of the halter and unfastened her black shorts. When they were off of her a tiny black thong was left, and Johnson pulled it aside. Carly had a good look at the woman's eyes, flaring with excitement as Johnson's fingers violated her.

"God I hope she cums," Carly said, whispering to herself in the quiet of her cabin. She felt bad about Johnson's struggle, and hoped the sexy blonde would be the charm.

Most of the talking seemed to be over, so Carly turned up the volume. The salon is a big room, and the camera was some distance away from Johnson and the woman, but with the volume up all the way the eerily muffled noises were unmistakable. The blonde was having fun!

She was a stunning looking creature in her tiny bra and thong. Quickly on her hands and knees next to Johnson, she opened his pants and inhaled his cock. Carly gasped at the technique — Johnson wasn't big, but still, right down the throat!

After a while Johnson pushed her away, his cock still hard and glistening. Carly wondered if he'd masturbated before he went out — he seemed to have his usual remarkable stamina.

When he and the woman were both naked he pushed her down on the soft leather and ate her. Carly was fascinated by her smoothly shaved pussy, with it's big, prominent, darkly pigmented lips. She'd heard a pussy referred to as a flower once before, and the blonde woman's almost looked like one. Johnson seemed to like it — his face was buried in there deep, moving side to side. Carly decided then and there that she needed to start dating again.

Johnson worked hard, but the woman didn't cum. Carly was getting worried. It was a long oral session, the kind of thing that should have at least got her close, but...no cigar. Johnson gave up. He wiped his juicy mouth on his arm. The woman said something Carly couldn't hear. She fumbled for her little purse and pulled something out. Carly assumed it was a condom.

The woman arranged Johnson on his back. She squeezed some lube on his rock-hard cock. She mounted him, reverse cowgirl style, lowering herself slowly, her mouth and eyes open wide. It was a slow process. Carly wondered what was happening. When the stunning blonde leaned back and fingered her own pussy it was unmistakable — Johnson was in her ass!

Carly swallowed hard. She'd heard about anal sex but had never watched that genre of porn. She never watched BDSM, or golden showers, or any of the other things that always seemed so filthy to her, partly because she assumed the participants would be skanky looking degenerates. The blonde riding Johnson was hardly that. She looked incredibly beautiful and sexy, and really happy to have a hard cock way up in her ass.

Carly watched as the ass fucking got underway. The woman's hand was on her wide-spread pussy, working furiously. She wasn't just rubbing one out, her fingers were three knuckles deep in the squish. It was a wild scene — Johnson's hips thrusting upward, the woman's increasingly orgasmic body bouncing and writhing, her hand moving at the speed of a blur. Johnson's muffled moans joined with the blonde's increasingly loud shrieks. Carly wondered if any of the neighboring yachts were aware. She zoomed the camera out and sure enough, just as she thought, Johnson had left all the windows shades open.

Carly zoomed in on the couple just in time. A devilish shriek emanated from the monitor's speaker as the woman came hard, her body reacting differently to Johnson's insistent thrusts, getting limper and less controlled as the big orgasm scrambled her nervous system.

"Fuck!" Carly whispered to herself when it was over. "That was fuckin' real!"

She zoomed in as close as she could on Johnson's face, hoping he knew it too. She was pretty sure he did.

The blonde was breathless, trying to gather her composure. "Did you cum in me baby?" she asked.

"There was no way not too," Johnson said, breathless and happy looking.

"You like my ass?" she asked. "Wanna fuck the rest of me now?

—

Johnson walked into the galley shirtless and barefoot, with wet hair. It was the first time Carly had seen him that casual.

"That smells good," he said, sniffing the peppers and onions Carly was cooking on the stove. "How was your evening? Anything good on TV?"

Carly was momentarily embarrassed, but Johnson looked happy and his eyes were twinkling. "What's her name?" she asked.

"Lisha. You watched?"

"She's not a faker."

"No, she is not," Johnson smiled.

"How often do girls...want it that way?"

Oh, the anal, you mean? Not too often. It seems to be more popular now than it used to be, but...yeah, she was different, wanting it right off the bat like that. She really likes it."

"I'd say she really loves it."

"So, please tell me I wasn't dreaming," Johnson said, "she came all over the place, didn't she?"

"Oh yeah. That girl's orgasmic. That was...quite a show. After her first one it was like there was no stopping her."

Carly wanted to comment on how there was no stopping Johnson either. She hadn't watched people fucking all that often, but Johnson's performance with Lisha was truly impressive.

Carly stirred the sautéing vegetables one last time and poured in the whisked eggs.

"I'll get fat eating all your good cooking," Johnson said, pouring himself a mug of coffee.

"You need your stamina," Carly said. She blushed, wishing she'd said something different.

Johnson smiled. His quest for the elusive female orgasm had driven him to learn to control his own orgasms. He knew he was pretty good when it came to hanging in there, and he was glad Carly had noticed.

When the eggs were cooked she plated them and served them with grapefruit halves and toast. She noticed Johnson's freshly showered scent when she sat down across from him. "Are you going to see her again?"

"Lisha? Oh, I don't know," he said, sounding like he hadn't thought of that before.

"Do you ever?"

Johnson smiled. "Am I a slut? Do you disapprove?"

"No, it's not that. But you've obviously found a girl who has real orgasms, right down to the molecular level, and she's gorgeous to boot. Why not give her a chance?"

"Then I'd never know. Maybe it's just her. Maybe what happened last night had nothing to do with me."

"Oh, that had to do with you. Trust me. You made that girl cum. Eight times if my count was right. That's a new record I think."

"You're good for my confidence, Carly."

"How come you don't use the hot tub with any of your women?"

"I don't know. I guess I never think of it."

"I thought maybe it was because of the neighbors."

"Fuck the neighbors," Johnson said. "Hey, speaking of which, have you met Bill? He's three slips over from us I think, in the champagne-colored Nordhaven. Pretty boat."

"Oh, yeah, I spoke with him the other day."

"He was asking about you. You should work on that," Johnson smiled. "Guys are easy, you know."

"What did he say?" Carly asked, suddenly very interested.

"I think he was wondering if you and I had anything going on."

"Oh my God, do we? I mean...what's this we're doing?"

"You're helping me with my psychological problems," Johnson said, smiling.

"Yeah! Sitting in my dark cabin watching you fuck! That's not normal, Johnson."

"But it's fun, right?"

Johnson spoke the truth. Watching him fuck Lisha five different ways and twice in the ass was a thrill Carly wouldn't soon forget. But would Johnson brag about the cameras and the voyeurism to other men? Would he tell Bill what she'd been up to? Carly was starting to think she didn't care.

—

Johnson took a break from women the next night, staying home in the quiet of his stateroom. Carly looked in on him for a moment. He seemed to be writing an email or something. She turned the monitor off and felt bad about looking.

Carly liked to check the dock lines one last time before turning in for the night, so she went up on deck for a walk around. Bill was passing by the end of the dock, walking his dog.

"Hi, Carly. How are you?" he said.

"Oh, hi," Carly said. "It's Bill, right?

"Yes. And this is Charger. Beautiful night, isn't it?"

"It is." Carly smiled at Bill's kind looking face and the handsome golden retriever on his leash. "Would you like to come aboard for a drink, Bill? I've got it on pretty good authority that drinks are on the house around here."

"I'd love to. Just let me bring Charger home."

"He's welcome."

"Thanks, but his claws need to be clipped. I'd hate to have him scratch up your nice new deck."

Carly watched as Bill walked to his boat. He had a nice ass for a man in his mid-forties. Her whole body tingled a little. She was ready for some excitement.

Bill was back in three minutes, walking at a brisk clip. Carly welcomed him aboard and strolled the deck with him, giving him the lay of the land.

"Beautiful ship," Bill said. "Puts my little boat to shame."

"Are you kidding?" Carly said. "I love your boat. I think the 43 is the perfect size."

After some more chat about the ocean crossing abilities of smaller powerboats, they found themselves at the bar in Blondie's dining area.

"You sure Johnson won't mind? I'd hate to get you in trouble with him."

"Actually, he's been after me to get a social life, and said to treat Blondie like my own. I got lucky with this job. He's a pretty terrific boss."