Substitute Skipper

She said she was aware of some primitive instincts in herself. "Don't guys usually like to be dominant? That's what I read."

I said I guessed some guys had a desire to be in charge but in modern times it wasn't politically correct, so it could conflict with the morals of the smart, self-aware types she would probably want to date.

She nodded. I was beginning to guess what she was really after.

She said, "How about we try it?" She thought some more. "I want a personal demonstration. I'll be your sex slave. Until I decide to stop, of course, and for sex only. It'll be fun!" She looked at me carefully, then put her hands under her dripping breasts and held them up to me. "What do you want to do with me?"

I did a double-take and my modern brain blurted, No way! I respected her too much. But she persisted. "Really! It should turn me on. Use me. Please?"

It occurred to me that she was acing another exam. She could have any guy she wanted. Like some hulking free safety with a 2 o'clock shadow. No, wait, she doesn't relate to that. Beaker, from the Muppets? Maybe if he played free safety. God, this was confusing. Was she making fun of me? Was she even slightly serious? The one thing I knew for sure was that I was looking at her soaked crop-top with water still dripping sporadically off the tips of her nipples onto her crotch. She followed my gaze and opened her knees.

As so often with Liz, my CPU entered an endless loop and my mental BSOD flickered. She rebooted me by kneeling beside me on the cockpit bench, pulling her crop-top up above her boobs, and asking with wide-eyed seriousness, "Is this OK?"

She stood me up and gracefully bent to pull down my trunks. My cock sprang up so hard it almost hit her in the face. Never smiling, she knelt and opened to let me put it in. It looked huge against her small features. As on our first night, her lips seemed stretched as she vacuumed it in. She began to lick and suck, looking for my reaction. Each time I sighed, I could sense the Database of Male Pleasures learning, growing. Soon she was maintaining eye contact, getting deeper and sloppier, trying to deep throat me and drooling on her tits. She either stroked my shaft, held up her tits, or put her hands behind her. She smiled happily, when she could.

Since she wanted my input, I helped her to her feet and turned her to face the bar and dock on shore. I pulled off her shorts, exposing a tiny g-string. I nestled my cock into her ass crack while I rubbed the front of her g-string, which was still damp. She stroked me up and down with her ass and arched her back to kiss me over her shoulder. The faint sounds of reggae and chatter floated over the water, and the shore lights paraded back and forth as the boat swung at its mooring. I started playing with her breasts and nipples. I moved a hand down to her g-string, this time sliding my fingers underneath the fabric and down to her very wet pussy, and I slowly inserted a finger. After a minute she was squirming against my cock. She started to moan.

Hmmm. This wasn't going as planned. Must. Think. Caveman. I slapped her ass, grabbed a handful of hair, and twisted and pushed her until she had to sit, then lie face down, on the cushioned cockpit bench. Then I raised her butt, ripped her g-string down, and entered her. I grabbed her hair again and pulled her head back, full caveman, so that she was trapped against my cock. I slapped her ass lightly with my other hand as I stroked in and out. I don't think she was scared -- we got along too well -- but I wanted to create a non-nerd experience. She had been loud before and she was again, moaning with each pull of her hair, but the wind was sighing in the rigging and I was confident we were alone. And she was really getting into it.

I reached around and grabbed part of a tit. She moaned some more. I let go of her hair and grabbed both tits, pulling toward me on the in-strokes. I could barely get a decent grip -- I could never palm a basketball either - but my brain was exploding. I barely held on, but she did seem to come at least once.

I pulled out, flipped her over and sat astride her. Reaching over to the binnacle, I grabbed the girls' savage tan coconut lotion, squeezed some onto her tits and smeared it around. Then I put my cock between them, and waited. She crushed her tits together for me. My cock completely disappeared unless I pushed all the way forward. I stroked in and out slowly, savoring the look of her boobs and her expression. She was fixated on the head of my cock disappearing between her boobs and then reappearing to point right at her nose. Finally I grabbed her hair again, pulled her head up and shot four or five ropes of cum on her face. She smiled.

"That's the first time anyone has done anything like that to me!" she said. I said I was sure it would happen as much as she wanted. She had only to ask.

We stayed in place companionably for a while, with me massaging her coconuts (which now smelled accordingly), and her stroking my cock with her tits and making a game of trying to capture it in her lips. We agreed caveman was fun but not a staple for people with the burden of a modern brain.

Eventually we saw the gang heading back, still singing and high. We made ourselves presentable. Becky came over with her palms in the back pockets of her skin tight hot pants and her giant boobs projected forward under a light, airy tee. She leaned close and said, "Fun and games tonight! Get your beauty sleep!" I kissed Liz good night, went to my cabin and took her advice.

Four o'clock. The witching hour. So soon! Becky slid silently in and threw a bunch of stuff on the v-berth. By the moonlight slicing through the open foredeck hatch I saw that she had on a light silver chain anchored to her nipple bars at each end. She said, "Fantasy Night. Tie me up and fuck me, please!"

I looked at what she had brought: some line, lube, a vibrator. Did she really find that all this stuff at a beach boutique? I let it pass.

I looked around the cabin and was inspired. I stood her under the hatch and grabbed my belt. I let her worry for a minute, then placed her wrists together in front of her, lassoed them with my belt and passed the loose end down between her palms and back up between her arms. Then I told her to stand on her tiptoes, and I pushed the loose end up through the hatch as far as I could before I dogged it down, trapping the belt. She was suspended on her toes.

She glowed with anticipation. In my opinion, anticipation is the best part. So for a couple of moments I let her semi-dangle there while I admired this plush body with the cantaloupe-size breasts and creaseless ass cheeks. I ran my fingertips over her smooth white skin, everywhere. She didn't like being tickled and tried to shake and squirm her way free. Her tits and ass shook like jello. Then I kissed her for a long time while I played around with her tits and nipple chain. Her heavy breasts were surprisingly firm and springy; holding down the nipple chain yielded a nice rebound when I let go. Then I stood back and toyed with her pussy. She started to breathe roughly. She was trying to stay still, but eventually she started to squirm. So when she was good and wet and sweaty, I knelt down and started to eat her pussy. She thrust her hips forward, opened her legs and stared down at me. At intervals she would roll her head back and stare up through the hatch. I stopped and asked, "More?" She just said "uunnnnnhhhhh" and thrust her hips in my face.

It was at this point that I discovered that she was wearing a jeweled butt plug. Then I discovered that her vibrator could reach her pussy and her butt plug at the same time. She seemed torn between locking her knees together or opening her thighs to the max. After several minutes it was driving her crazy, like I thought she wanted. I could see that she needed to writhe and thrash but also wanted to be quiet and not swing the nipple chain or bang the mast or cabin walls. She was now going "uunnnnnhhhhh" constantly and thrusting her hips in a fucking motion. I loved to watch her round parts in motion.

Eventually I stood and gave her a series of long, full body, standing kisses. She held my stiff cock between her thighs and humped her pussy lips along it. We were both ready.

I let her down but, bowing to her preferences, I tied her arms tightly behind her back. Then I ran the end of the line up around her throat, not dangerously tight but enough to keep her back arched and her breasts pushed out. I lay down on my back and invited her to sit on my face. She needed to get herself up on the berth, which was a watchable struggle in her tied condition. She climbed over me and lowered herself, and I stuck out my tongue so she could center herself. I held her thighs and kept eating her until she was panting. Finally I wriggled forward and positioned my cock under her pussy. She descended on it with enthusiasm and started to fuck me, bounding up and down, breasts and chain flying everywhere, until she came and collapsed. I think she liked it. I know I did. I bet most of our eavesdroppers did too.

FRIDAY

Our last full day. Everyone wore a competition suit, but Becky took the lead by going topless again and strutting her nipple bars, sans chain. They went well with her bondage-themed bottom.

Deirdre had never seriously competed in this event. I found her suits sexy but too tasteful to win any prizes in this group. I was surprised to see her surface in a new one, a dark blue thong with narrow triangles on top and arcs of rhinestones centered on her breasts and box. They said, look here! And here! without being trashy. It went perfectly with the long, thick blonde braid coming high off the back of her head. I wanted to grab it all day. With her beautiful face, I was in heat the whole way to our last anchorage.

We sailed to a harbor nearer the charter base. The sail trimming was especially delightful. I was becoming an experienced letch. Partway there, Deidre sidled over and told me that the crew had granted her the entire night with me as a thank you to us both, me for services rendered and Deirdre for "organizational efforts." I assumed that meant dreaming up the dating system. She said "that too," which I didn't quite get. I tugged gently on her braid and said I was really looking forward to tonight. She grinned and leaned against me. Her boobs almost escaped.

We arrived and dropped the hook. There were few other boats and nothing on shore, which was perfect for us since we were planning a last party aboard. The afternoon was spent swimming, sunning, snorkeling and drinking. Even the skipper got some rest.

At six, we fired up the grill and cooked the last of our provisions. A motion was made to finish up the rum. We sat in the cockpit drinking and singing a few calypso songs. We were pretty wasted.

After sunset, in the cool of the evening, we adjourned to the cabin and got out the cards. As I had anticipated, someone suggested strip. Becky, still topless, complained she was at a disadvantage, but no one seemed sympathetic. We all had only two or three items on anyway, so it seemed the game was going to be short. To lengthen it, we said the winner could pick one person to take off one item. The cards were dealt.

Now, I don't mind a fair game. And I was wearing three items, if you count both flip flops, which I did. But I wasn't thinking clearly. The mob was against me. There was an 84% chance a girl would win each hand, and a 100% chance that the person she selected to take something off was me. It took two rounds for me to get down to only my swimsuit. I won a hand and had Lingerie take off her top, to general acclaim. Then Lingerie won and had me strip naked. Then Becky won and looked at me speculatively.

I was in a bit of an alcoholic fog, so I couldn't do any quick thinking. Becky, though, knew what she wanted. "We want to see you jack off," she declared. "Stand up, though." I looked at the others. It seemed unanimous.

"Don't you dare come, though," said Deirdre.

I stood up. I was half erect already. Becky produced her tube of lube and said they wanted to see me use it. Had this been discussed? Deirdre, with the organizational talents, was grinning an evil grin.

I put on some lube. I was feeling embarrassed. They had all seen me before but now I was on exhibit. I began to understand how it might feel to wear some of the tiny swimsuits they had been flashing at me, and I got harder before I even touched myself. Becky said to stop delaying, I had no choice.

It took about a minute to get a raging hard-on. I had to stop. Becky said, "Wait, we can help." She slid to her knees in front of me. She beckoned to the also topless Liz and patted the spot next to her. Liz, to my astonishment, submissively walked over and knelt beside her. Then, to Liz's apparent surprise, Becky kissed her full on the lips and grabbed her tit. Liz seemed startled but then kissed back, in data-gathering mode, I supposed.

Meanwhile, I was about to pop. Suddenly Deirdre jumped up and said "No you don't!" Becky stood, came over and took the measure of my cock with her outstretched hand. She said, "Very nice. He's all warmed up for you, Deirdre!" Her boobs were swinging right next to my face, Liz was still kneeling topless right in front of me, all the girls were inspecting me, and I was still jacking because, well, you can imagine. Fortunately Deidre grabbed my most outstanding feature and pulled me into the fore cabin.

Inside, she gave me a long, wet kiss with a couple of light strokes thrown in, and then left again, with instructions to "keep yourself warmed up."

Minutes later I heard hooting and clapping in the main cabin and Deirdre walked in, a cartoon version of pure sex, by which I mean thigh-high fishnets, a jeweled g-string and a push-up open cup bra, all black as the night. Even in my muddled state I wondered why she had brought that stuff on the trip. Unusually foresightful, I thought. I let it pass.

Her boobs looked larger now -- outsized, in fact. I was lying on my back and they were pointing right at me. "Still happy to see me!" she observed.

My stiff dick was pointing more or less back at her. "Don't touch me," I said, "and don't point those things at me or I'll shoot you."

"Don't shoot!" she said. "I can't lay down my weapons, but I'll keep my movements nice and slow."

"This is our last night aboard," she continued. "Our last night on these sheets. Also, we seem to have some excess supplies" -- she waved a familiar bottle of lube at me -- "and I thought we should use them up. What if I pour this all over myself before we get started?"

I may have groaned. I said she was now going to be QuadrupleThreat. "Just because I'm responsible doesn't mean I'm good," she said teasingly. And she opened the bottle.

I'd like to report that I watched the next couple of minutes with cool amusement, but my brain was a fireball. She removed her bra and dribbled a little on each tit, then rubbed it in slowly and mashed them around while watching my reaction, and my cock's. Then she pulled the top of her g-string away from her body and dribbled some on her tummy so it ran down into the gap. She shook herself as though it were chilly. Then she poured larger amounts into one hand and rubbed it all over. When she did her ass, she turned around and bent over so I could get the full view.

I still didn't want her to touch me yet for fear of premature thermonuclear explosion, but given all this lotion, I knew my role. I removed her g-string, but not her stockings, which I liked. I placed her on the bed and set about massaging her boobs and pussy while standing over her. I wanted to see whether I could bring her off with just my hands. She closed her eyes. I took my time and kissed her all over, while running my fingertips lightly over her inner pussy lips and clit hood, then inside her, increasingly fast and deep. I lightly pinched and twisted her nipples. She was making agreeable little sounds, but not obviously cumming.

To make use of all that lube I moved her away from the edge and lay down on her, face to face. I could slide my whole body up and down her frictionlessly. I started to stroke while manhandling her slippery tits. Staying on top of her was a problem, though. Having my cock in her at least stabilized my hips, but staying aboard required too much concentration.

So I positioned her at the edge of the berth, facing away, on her knees. She was thoroughly wet as well as shiny and slippery all over. I delayed entering her just to gain some extra time and ran my cock over her pussy lips. This wasn't helping. She said, "We have the morning. Just do me. But I want to see you to come." So I stuck it at her entrance, grabbed her thick braid, and pulled. She slipped onto me easily and started to work herself to and fro. I assisted by pulling her braid, which kept her head up and back arched. With my other hand I reached under her to stroke her slippery boobs and let her nipples graze my palm. She gasped with each stroke to encourage me and eventually gave a little moan and a long shiver. She even orgasmed with class!

I felt the jizz rising. I withdrew, flipped her over and sat astride her, aimed at her tits, and came. It landed randomly on boobs and chest, plus the first hard spurt on her face. "Sorry," I said, but she just smiled that beautiful smile, raised her tits to her mouth and was just barely able to lick the tops clean. We kissed. And kissed.

And then we just talked. And talked. I could talk to her for hours. She was a great, encouraging listener, and I tried to be too.

Eventually she said that the no-relationship rule had started to bother her. It had made sense at the time but now that the trip was ending it seemed harsh. "Since I've been making the rules here, I deleted it right after poker."

"What have you done, woman!" I exclaimed. "Do I now have to keep five girlfriends entertained?"

"I may have forgotten to mention the change to the others," she admitted. "There's been a lot going on, and a lot to think about."

Much later, after peeking out of our cabin to confirm the others had gone to sleep, we crept up on deck and went skinny dipping to clean ourselves off. Then we came back and talked some more. I told her how much I appreciated her making the effort to be sexy for me, and she said she enjoyed turning me on because we were birds of a feather. I had an opening and a decision to make, but I found I had already made it. I asked whether she meant birds of a feather should flock together, and she said that might bear further discussion. Despite the kidding she went straight to the issue and said, seriously, "I wasn't looking for this but I don't want to lose you after this trip."

And in the morning we made love.

SATURDAY

We returned the boat to the charter base more or less unscathed and set about the depressing tasks of packing and dressing for travel in actual clothes. When all was done we patted our boat goodbye and had one last drink while waiting for the airport shuttle. All except Amber, who was orbiting in her crocheted bikini, fishing for stares from middle-aged husbands.

We agreed the voyage had been a great success. I noted it was the fortunate result of an unlikely series of events, and I for one was sorry it would never happen again.

"Oh, I don't know," said Becky. "What about same time next year?"

"I hope my sister isn't going to break her other leg," I ventured. "So I'll be off the boat, but you guys should definitely do it. You'll have a lot of fun."

There were big smiles all around, and some eye-rolls. Everyone looked at Deidre, the organizer extraordinaire.

She gave me her familiar 'you poor guy' look. "You really thought your sister broke her leg?" she asked. "She's been skiing all week with Hans."