Substitute Skipper

"I can't believe I get only one more session," she said. "This paradigm needs a complete re-think. Who dreamed it up anyway?"

"Maybe you can buy out Amber," I suggested.

"Too late," she said.

We talked lots more, played with each other's body parts, and dozed, but all too soon her phone went off and she said, "Cinderella time." We feverishly started buttoning up her cover-up, which took a lot longer than unbuttoning it. I worked up as she buttoned down. We came out with a button left over and giggled. Finally she gave me a last long kiss and dashed out just before midnight, and on the stroke of two, in walked Amber.

How did I know. The nice thing was that she brought us each a rum punch.

I had been worrying about this moment because I had been repelled by Amber's personality. But now there was no one else was around to compete, and she didn't say much. She was wearing a beach towel which she quickly removed to reveal just a black thong. We sat on the berth reclining against the hull. "Doing OK?" she asked. I said yes, and in fact, between the rum and Amber's quite beautiful body, I felt I might be up to the job. We talked while we drank, with her sitting there topless and in fact, naked except for a couple of strategic square inches. My simian brain noticed that her skin was pink and clear, her breasts shapely and perky. I recalled from earlier that her ass had zero sag. She had little if any pubic hair. She was leaning a boob against my arm. Without an audience to play to, she was almost human. I gathered myself. It helped that she grabbed my cock and went down on me without further discussion.

Unfortunately she opened with a maximum speed bobbing motion rather than anything sensual or creative. I like a more relaxed and teasing approach, but predictably, this wasn't Amber. I was so dismayed that I actually grabbed her head, pulled her off, and gave her some advice disguised as a request: "Can I ask a favor? You are a stunningly sexy girl; you don't need to work so hard. Play with my brain instead." I lay down and asked her to keep eye contact, start slowly around the edges, rub my cock on herself, and tease me a little. A grin to indicate she was having a good time would be enjoyable. Deep-throating could be left for later. "But be sure to stop when I say. I'm not sure how long I can last, with a fox like you on the case." We worked it out and eventually I had to tell her to stop immediately. She licked one drop of precum off my tip and gave me a big grin. Things were going better.

We both got off the berth and stood on the cabin floor. I put my hand on her shoulder to push her down and played around with my cock on her face. She seemed accepting. Then I sat her on the edge of the berth and peeled off her thong. I toyed with her pussy and started to eat her, but she made noises so I stopped, went "Shhh" again, and put a hand over her mouth. She seemed compliant so I recommenced. She arched and squirmed but didn't utter a sound.

Eventually I jumped up on the berth with her, flipped her over, lifted her hips and pushed her shoulders down. She willingly held her ass high while I waited a few beats for dramatic effect and then ran my cock up and down her pussy. She went "uuuuunnnhhh", but quietly, and tried to push back onto me. I pulled back and teased her pussy lips some more. It helped that I wasn't worried about her good opinion, but she seemed to like it anyway. I leaned over and teased her nipples, and then I experimentally gave her a firm slap on the ass. She grunted again but it was more of a moan. With my cock between her legs I reached forward, pinched both nipples and twisted fairly hard. She went "Hhnnnggg!!" with her lips closed. Finally I entered her, and she immediately started a frenzied fucking motion. I grabbed her hips and stopped it, then began a slow but accelerating pace. She came, a little too loudly, but at least I could tell she was trying to be good. After a minute I continued for a long time and eventually she seemed to come again and fell sideways on the berth.

"Again" she said after a minute.

I told her I needed to rest and I tried to sleep, but I could feel her fingers running lightly all over my body. When it was getting light she ran them over my cock, reversed her position and took it in her mouth. I let it happen, but interestingly I started to get hard again. I turned on my back to watch. She moved between my legs so she could maintain eye contact and licked all around the edges of my head. She ran her tongue up and down my shaft. She played my cock around her face. She was an eager learner, but it was effective. When I was completely hard I fucked her for a while, with her on top, and I watched her perky tits vibrate with my strokes. I eventually came. She acted like she did too; maybe she did. But eventually the clock got near six, so we cleaned up and I kissed each of her tits goodbye.

This was going better than I thought. My next worry was All Star, since Becky seemed super-hot and I doubted Lingerie would follow through.

MONDAY

After a nice breakfast of bacon and powdered eggs, we (i.e., my crew!) dropped the mooring and set sail for our next harbor, a more remote and private bay not on the map of suggested anchorages. The wind seemed calm, so I thought we could stay there without rocking too much at night.

As we left the mooring field the girls readied for sunbathing, which was my favorite part of the morning. I thought the Swimsuit of the Day meme might turn out to be a very good thing. Who wouldn't want to one-up Amber? Not Becky; she just repeated her strappy black suit. Not Deirdre; she just repeated her suit from yesterday and gave me one of her lovely smiles when no one else was looking. She really had a fabulous face. Lingerie wore her one-piece again. Amber was sleeping late, a point I'm sure everyone was meant to notice.

Delia. She wasn't a fan of Amber's, but she was competitive and she emerged with another, even narrower ultra-high-waisted string bottom that made her long legs look endless and a top that had little triangles suspended above the chest band, showing top, side and under-boob in large amounts. I mentally named this her "competition suit." Her ribs and abdominal muscles stood out as she moved. Her breasts weren't large for her frame, but they were large in absolute terms and they were the only part of her that, due to minimal capture by her bikini top, jiggled. I loved it. I wondered if she was next.

My suspicions were partly confirmed when she came over, sat beside me at the wheel, and started a conversation - to break the ice, I thought. I had trouble keeping my eyes up and eventually she said, "See anything you like?" I replied, lots. She grinned, bumped her shoulder against me and said there was more to come. I took a chance and said yes, there was plenty to cum on, and she escalated with, "That's fine, stud. I'm open for business." Yeeesh.

Amber made a big show of rising sleepily just before lunch. She came over, gave me a kiss (which I guess was not against the rules), and whispered "Thanks for the lesson." I admit the recollection was arousing.

I was happy to discover that the Swimsuit of the Day competition, having sprung from nothing but Trouble's fertile imagination, was paying big dividends. Since I was usually steering, the girls were in charge of winching in the sails. This was a big, heavy boat, and the loads were significant, so even with powerful winches the act of grinding them -- bending over to rotate the winch handle in wide horizontal circles -- took lots of effort. I was treated to visions of straining glutes and swinging tits every time we tacked. Once the well-endowed Plush popped out of her tiny top. She reflexively glanced at me as she quickly stuffed herself back in, and of course our eyes met. I shook my head, eye-rolled and smiled to signify wonderment, and she ended up smiling back. Later that day she started going topless. Yes, there were nipple bars.

After lunch we went snorkeling, and again I had a hard time taking my eyes off Delia. Also, I had a hard time keeping up with her as she knifed through the water. Lord knows what combination of training and genetics produced that physique, but she was unique in my experience. Eventually she came up behind me and ran her hand up the inside of my leg. I thought it was a shark and jumped. She said she didn't bite. I said, "Too bad!" and she laughed, ran her palm up to my crotch, said "Maybe tonight," and scythed off, grinning evilly.

We climbed back up the swim ladder. While Becky waited her turn she floated on her back, and I was pleased to see her two big floatation devices doing their job.

The sun had been hot and everyone was drinking rum to hydrate. Becky sat next to me in the cockpit, perhaps by prearrangement. I felt the ghostly hand of Deirdre's organizational talents.

Soon Becky's hip was pressed firmly against mine and I was super-conscious that her large, soft, bare left tit was a millimeter from my forearm. Whenever she turned, we connected and the tit squished, and when we parted, it sloshed. Neither of us acknowledged this arrangement. We both acted unaware. We weren't. Her beasts were the size of melons and I bet everyone present was watching out of the corner of an eye.

Then, talking to someone on my left, she half-turned and pressed her left knee against my right knee, making contact the full length of our thighs and parting her legs widely.

I was uncomfortable being assaulted with everyone sitting around, but I felt I shouldn't back down, so I accepted the offer by resting my hand on her knee and casually, unconsciously (hah!) sliding it higher on her leg and further inside her thigh as the conversation went on. Again, neither of us acknowledged the situation, but she increased the pressure against my leg.

Eventually I could slide no higher. So I stopped. She turned to her right to talk to someone else and moved her right knee right, opening her crotch about 90 degrees. Now it was a game. I looked across to where Deirdre was sitting, and she shrugged, eye-rolled with a grin, and mouthed "I warned you." Good grief. I started gently scratching Becky's suit right over her clit with the side of my little fingernail. The material had a definite texture, and the motion produced a small scratching vibration. I waited for her next move. It was slow in coming.

But it came. She slouched down, pushed her hips forward, and exposed more of her crotch. I scratched lower. I didn't see how she could stand it. She finally turned to me and in a perfectly composed manner and with not the hint of a smile, said, "I'm getting hot." This, while I was scratching her pussy in a crowd of people. I de-escalated and said maybe it would be cooler at night. She said, "Great. See you for the late shift. If you're still alive." My sentiments exactly, I said.

Dinner was another grill-out, and we again played cards, this time nickel-dime-quarter poker. I doubt I was the only one considering the implications, since I was probably the least sexually needy one on the boat.

Then it was time for lights out, and I awaited the next visitor. Someone just outside my cabin door whispered, "Just a few minutes," and I realized just how non-soundproofed my cabin was.

Delia strode in a different woman. She was wearing only tiny lace panties and perfume. Her hair was bunched in a harem-girl ponytail right on top of her head. She came in for a kiss. She sat next to me on the edge of the berth and said, "I'm glad you agreed to this crazy arrangement. You're way cute, and being down here in the tropics makes me soooo horny."

I said, "Who are you and what have you done with Delia the jock?"

She said this was the real her. For special occasions.

Suddenly all those muscles and tendons seemed less threatening and more like just a lack of fat. For her height she was light as a feather. She was enthusiastic and ultra hot. As we talked, I casually reached over and ran some fingers up her thigh, then toyed gently with her nipples. She watched, and conversation ceased. I stood in front of her and put one hand over one breast, then the other. A handful each. I reached down inside her panties, between her legs, and she spread them passively. I toyed with her pussy lips while I kissed her. She kissed me back and gave a gentle tug on the top of my swimsuit.

I slipped it off. Somehow she gracefully shook off her panties in a flash. While we were standing I played with her nipples some more and kissed them. She surrounded my face with her breasts and rubbed. I put hands on her shoulders and looked down at my cock, and she got down on her knees and rubbed it with her tits. Then she started to suck me. I imagined I could feel an ultra-fit tongue muscle running up and down my shaft, and I couldn't help grabbing her convenient ponytail and adding a little fucking motion, which she accommodated without complaint. The moment is flashed into my long-term memory.

I was about to burst, so I backed her up to the bed and pushed her down on her back. Her hips were right on the edge. She put her legs in the air and I, still standing, entered her and started stroking. She folded her legs around my back. As I speeded up her tits bounced in rhythm and she made a motion to steady them, but I shook my head, reached under her knees and grabbed her wrists. She grinned her awareness and I pumped harder. They bounced wildly.

I pushed her further onto the berth, turned her and got up with her for a more comfortable conclusion, but when I bent down to kiss her, she gripped me with arms of steel that nearly crushed my ribcage. She pumped back against me, her breathing fast and ragged. We fucked each other at maximum strength for minutes, and eventually, she came. I continued because I was less deprived and slower. Also, because she didn't stop or let go.

After many minutes I was running out of stamina. Not her. We continued for what seemed ages, grunting and bathed in sweat. Her foot banged a wall. I slipped and my ankle hit the aluminum mast, which reverberated throughout the boat. We continued. This was passion to exhaustion. Finally she came again, and I fell on top of her. I couldn't speak.

After about a minute she whispered brightly, "That was fun!" and started running her nails lightly over my back. I was limp, panting, and sweating rivers into the sheets. She sat up. I flipped over and panted on my back for a change. She looked down and said, "If you want to get in shape, I'm your girl." Between pants I wheezed out that a trainer like her would kill me. "What doesn't kill you...!" she said cheerily. "Let me know when you're ready to go!"

After an hour I decided I had expectations to meet, so I laid her down on the bunk, climbed between her legs, and started to eat her. She didn't go for too much teasing. She put both hands on my head and pressed me hard into her snatch. With a struggle I made room for an arm and got two fingers into her slit while I worked over her clit with my lips and tongue. I tried suction and a little nibble, both well-received. Again, her endurance was fantastic. We did this for what seemed like hours, while she made encouraging noises and shivered to indicate enthusiasm. Finally I reached up under her raised legs, grabbed both of her tits, and twisted her nipples a bit. She shuddered for a minute and then relaxed.

The clock approached midnight and I had managed to save myself through sheer fatigue. Delia grabbed her panties and traipsed blithely out the door. Confidence is sexy, I thought!

I flopped and may have gone to sleep, because it was 4 AM before I felt someone slip into bed beside me. "I thought you might need a rest," she said. "Got anything left?" It was Becky, of course. I didn't need to open my eyes because I felt a huge orb resting against my arm.

I said this format is tough, but for her, absolutely. It felt like she was wearing just a tee shirt, and she rested one of her big soft tits on my chest as she thoughtfully stroked my face and head with her fingers. She placed a gentle kiss here and there, and then a big one on my lips. She threw one leg over mine and drew a thigh up to my crotch. "You're a wreck, aren't you?" she said. I said I had just run a couple of marathons but had saved myself for her. She brightened. Reaching down, she started stroking my cock. Which reacted. She stood up. I opened my eyes and peered at her for the first time. Her tee shirt said "TIE ME UP" in block caps within the suitably placed image of a nipple chain.

With a major effort I levered myself up and stood in front of her, grabbed her wrists, and held them behind her back while I kissed her deeply. She was soft as a pillow except for her tongue stud and nipple ornaments. My erection was between her legs. I raised each of her hands to her opposite elbow behind her and said "Don't let go!" She kept them in place while I freed myself to grab her awesome tits.

I mauled her big boobs and kissed her face for a while, and then I pulled the shirt over her head. She had come commando. I played a little with her nipple bars, and kissed and sucked each nipple while she continued to act tied up. She seemed flushed and maybe aroused, so I backed up and put one hand on her pussy. A finger slid into her easily. I ran it back and forth a bit while we stared at each other from a foot apart. She started leaning toward me, so I stopped, got on the berth on my back, held up my cock, and silently invited her to climb on.

The berth was high and her magnificent breasts swayed as she hopped up on it. Then she got on her knees, positioned herself over me, and descend accurately. She repositioned her arms behind her! Then she started flexing her knees to move up and down. Her breasts moved up and down even more, of course, and with her arms folded behind her back they were naturally projected forwards. She worked to stay upright for balance. After a while she was flushed and panting. I think she was enjoying herself, but I know for sure I was in heaven. I let her free her hands, and she put them down next to my shoulders so her tits would hit my face on the downswings. I wouldn't last long like this. I slowed her and we rocked gently for some time. I was marveling at the perfection of her breasts and nipples, her hairless pussy, her fantastic, plush lips.

Those lips! I said, "I want to come somewhere fun."

She immediately got onto the floor, on her knees, and opened her mouth. She resumed holding her elbows behind her back, with a smile. I stood before her, stroking myself while storing another scene in permanent memory. Then I pushed my cock into her mouth and let her operate on it hands-free. She was good, and the tongue stud made it better. I said, ready, and she backed off a shade while I took over. I came big time, only partly in her mouth. She made a move to clear her eyes, but I shook my head and she resumed her hands-tied posture while I hit Ctrl-S again. Then I pulled her up, kissed her hard, and helped her clean up.

She stuck around for kissy face and nipple play until 6, and she said she was glad I took her shirt seriously. She said she was going to bring her toys next time. She kissed me thanks and left at 5:59. In that shirt.

TUESDAY

We sailed off after breakfast on a long trip to a completely unsecluded cove with a resort on the shore. Becky got the Award with a different swimsuit that was even more fetish-y. It was another black number, but with braided leather straps, a thong, and attachment clips and rings in several places. She removed the top and clipped it to a lifeline while we were out at sea.

We picked up a mooring in late afternoon and went ashore to look around. Becky donned her top just as we docked the dinghy, but actually, I thought her bare ass cheeks were just as stimulating. Some of the girls walked the beach, some went to the beachwear boutique, and I watched a game in the bar. We decided to have dinner in the informal restaurant, which looked nice and swimsuit-friendly.