Substitute Skipper

Lingerie Liz still hadn't had any time alone with me. I figured she might be next, but she was the quietest of the girls, and in case she did show, I wanted a chance to get to know her better. I worried she was stressing about my expectations for this bizarre arrangement, so I wanted a chance to assure her she could just come in and nap -- an idea that was beginning to appeal to me too, despite her walking orgasm of a body. I expected her either to sit with me at dinner or to take a pass on the sex option for the evening. But Deirdre came over late in the day and whispered that Liz wanted a date, but in the morning, so she, Deidre, as first in the second rotation, had been elected to see me this evening. She asked if I was up to it. I said I was hot for her but a talking date would be OK too.

Dinner was great because we never went back to the boat and all the girls were in their swimsuits. I had a hard time locating my mouth with the fork. We all drank too much and got slightly crazy. I bet it was pretty amusing watching us get in the small dinghy and try to find our boat in the darkened mooring field. Only Trouble fell in, and evidently she thought it was hilarious. After the long sail, the sun and the 150 proof rum, I fell on my berth and instantly went into a kind of sugar coma.

Deirdre came into my cabin a little after the appointed hour and lay down with me on the berth. She said nothing but rubbed my back. Eventually she mentioned she wouldn't blame me if I wanted some time off. She gave me the "you poor thing" look, but with a slight smile on that gorgeous face that may have indicated imperfect sincerity. We talked nonstop for an hour or two. All the while, though, she was wearing a t-shirt that said "JUST DO ME!" in case I was undecided. Somehow I managed to, and we languorously did what I can only describe as actually making love, trailing fingers all over each other, kissing, and attending to each other's wishes. I said she was irresistible and I could lie there with her forever. It was idyllic. We were both annoyed to have to part. "I can't really count this as purely recreational sex," I said. "There seems to be too much affection and respect involved. I'm still owed another visit." She said she'd see what she could do.

But I had another date scheduled.

I was wakened in the dark by a gentle touch. I reached for the light but before I could get to it a hand pulled me gently out of bed. I was still naked, I realized; not the way to greet a conflicted young lady. This one didn't seem to need a greeting. She pulled me right through my cabin door. I gestured to my naked body, but I could see Liz was naked too, except for a short, diaphanous negligee. Her entire porn star body was on display. I was instantly aroused. She pulled me quietly up the companionway and out into the cockpit, then onto the foredeck under the stars. A few lights shone on other boats, but all were distant. Silence filled the air. A light breeze skimmed my skin and the ripples in the water lapped at the hull. She had laid a cockpit bench cushion out on the flat part of the foredeck. She stood on it and turned to face me. By moonlight I saw her fantastic tits swing and settle as she turned. She took my head in her hands and kissed me slowly. I felt her chest against mine. She said not a word. I started to talk but she put a finger to my lips.

"Take me," she said.

Perhaps I had underestimated her.

She was shorter than me. I grabbed her, lifted her, hugged her to me and kissed her hard. Her breasts spread out all over my chest. I put a hand under her ass and crushed her crotch against my cock. She ground it around hungrily by hooking her legs behind my ass. I knelt and dropped her down on the cushion. She was fingering herself and holding my cock and pulling me down. I whisked the nightie off over her head. Twenty seconds after we first kissed, she was ready and I obliged. She grabbed my ass and pulled me in hard.

This was a total fantasy. It was a blur but I recall her breasts heaving around in wild abandon. I tried to grab one and it far exceeded a handful. I put my hands around her tiny waist and my fingers almost met. At one point I remember her ass held up to me patiently. At another I held her by the shoulders and she sucked me willingly, her lips stretched tight around my cock. I recall her sighs, whimpers, groans, and finally loud moans, and a woman's voice from another boat calling "Can I come over?" At the end, I finally popped out from between her lips and came on her tits while she held them up for me. We lay together naked on the cushion, kissing, licking, pinching, rubbing, flicking and grabbing, until the sun started its rise. Not a word was said.

When the light finally became too bright, she kissed me and walked unconcernedly back into the boat, naked and trailing her nightie. I followed quickly. I had no clothes either.

WEDNESDAY

At breakfast there was no mention of noises in the night, a tribute, I thought, to everyone's respect for Liz. She said little and didn't talk to me. She did hand me the first cup of coffee.

We decided to sail to a distant and lightly populated island, a trip that would require some real sailing and navigation. We cast off early in order to arrive while the sun was still high and the reef system surrounding the harbor would be visible through the water.

Soon a new bathing suit came out. I have to give Amber credit for daring; she herself announced she wasn't taking any chance on losing Swimsuit of the Day. She had bought herself a crocheted black micro thong thing with dangling ties on each side of her waist and between her breasts. It contrasted strongly against her pinkish skin. She was stunning and very, very hot.

Eventually, once we were on the high seas, Liz did come over to talk. She hoped I liked the sex; she had tried to make it as pure as possible. I said I absolutely loved it and that she had the hottest body ever. She shifted uncomfortably, but finally said she had put some thought into it. She was almost 2 years younger than the rest and felt inexperienced, in part because her brain and her body weren't in sync when it came to dating and she had learned to share herself sparingly. Her figure attracted the wrong kind of guys and daunted the other nerds. She was constantly fending off dumb, over-confident jocks. I asked how she was able to graduate with the others this Spring, and after a pause she admitted she had started college early, finished in three years and got part way through a doctorate in microbiology. But she said please not to spread that around outside this group; she was afraid it would give people the wrong idea. She also said she wanted our next session to focus on sex ed. A true nerd, with a Rolls Royce body.

We wended out way through the reefs with the aid of some buoys and a smartphone and dropped the hook in a small harbor with one other boat. The next dry land was Spain. The island was barely inhabited, but it did have a small beachside bar and grill for us yachties. We snorkeled on the reef, walked the beach, and watched for the green flash as the sun dropped below the horizon. Then it was time to fire up the grill and pour some drinks.

I expected Amber or Becky that evening and frankly I was looking forward to Becky's little kinks, but I recognized my error when Delia sat next to me at dinner in the cockpit wearing only a cut off t-shirt and the bottom of her tiny 'competition' bikini. She had revived the harem ponytail on the top of her head, which boded well. The last time I had grabbed that ponytail was etched in my memory. The breeze was cool and no one could fail to notice the bumps swinging around under her shirt as she chatted and laughed, but only I felt the heat of her arm and leg against mine.

After dinner she invited me to go for a walk on the beach. We dinghied ashore, tied up at the dinghy dock, and hiked toward the fading light. No one was near. Delia suddenly took her shirt off and tucked it under the side of her bikini bottom. I looked at her questioningly and she gave me a grin. "I just like the feeling." She wiggled like she had a chill. "It's a turn on." We walked on and I could see her scoping the area for other beachgoers, but no one came near. I said that being topless probably wasn't a crime here, and there probably wasn't a cop on the island anyway. I think that disappointed her.

She asked whether I wanted to go for a jog. I was conflicted. The sights could be hot but I wouldn't be able to keep up to see them. I agreed but warned her I'd quit early. She ran gracefully and joyfully but fast. After the first few minutes I ran out of gas, so I said "see you later" and she waved and ran on until she was a dot on the still-golden horizon. She returned and ran by me like a shot, skimming the ground, did a hockey stop in the sand and bounced back to me radiating pleasure. We walked back to the dingy dock chatting about other things. I detected no shortness of breath.

Just a little farther down the beach was the open-air beach bar. I asked if she wanted a drink, and we strolled over. It was almost dark. She reached for her shirt, but I put my hand on hers to stop her. She got the idea and we peered into the bar. It was dimly lit with colored bulbs. The floor was concrete. Reggae trickled from an antique speaker. The bartender was sleeping. I put my hand behind her back and pushed her in while she peered around every corner.

She sat with her back to the bartender, across a low table from me. I was planning to look at her tits but was struck by her legs again -- the flawless thighs and shapely calves, the flexing cords and tendons. She opened her knees a fraction, and I was reminded how small this bikini was. Her breasts were in perfect proportion, as all of her was.

She said, "Ahem, I'm up here."

I said, "But some of your best parts are right there," and I motioned to her chest just as the bartender walked up.

She jumped and started to raise an arm, but realizing that would only be humiliating she instead leaned back and asked for a rum punch. To his credit, the bartender acted as nonchalant as any guy can in that situation, but he couldn't tear his eyes off her minimally-clad body. When he went back to the bar she looked at me and grinned. She put one ankle on her other knee, which separated her legs even further. The crotch of her competition suit did not, I noticed, even begin to reach from thigh to thigh. She didn't redirect my gaze, and she didn't adjust when the rum drinks arrived. They were really strong, with barely any fruit juice.

A group of locals eventually came in. They sat across the room from us, but Delia was beginning to get some looks. I wasn't too worried -- she could probably protect me if necessary. Or if nothing else, she could outrun them all by miles. But I suggested we leave.

It was dark. She stopped just outside the lighted area, leaned against a palm tree, and tapped my shoulder. I settled into her arms and we shared a long. passionate kiss. She said, "That was pretty exciting. What's wrong with me?" I ad-libbed something about our little kinks being what gave us pleasure. She asked how much pleasure I wanted and kissed me again while I thought that over. We both looked around carefully.

As we kissed I scuffed out a depression in the sand to stand in and told her to remove her bikini bottoms. She complied. I grabbed her hard torso and quickly turned her away from me, toward the bar. Then I held her to me while I played with her breasts from behind with one hand and stroked her pussy with the other. We could see the bartender serving drinks inside, but it was brighter in the bar and I doubted he could see us where we stood. She tilted her head back on my shoulder and seemed to be warming up fast. Eventually I guided my cock into her and pulled her elbows back so I could hold her arms behind her. That left her breasts flopping while I pumped into her, and she started to gasp a little. "Quiet!" I said. She nodded. I hooked one forearm under both her elbows and reached my free hand around to play with her tits. Then I moved it down to stroke her clit. We were now making squishy noises and the bartender looked up just longer than briefly. He may or may not have seen us in the evening gloom. It was hard to tell, but we were hot and we continued. Finally she grunted more loudly and moaned, and, I think, came. We scampered back to the dingy dock.

We were feeling our way in the dark. The dock was lit by a solitary bulb that dropped a dim cone of light on the weathered planks. I started to climb into the dingy, but she held me back. "This is a fantasy," she said in a whisper. She led me directly under the light and faced me. By standing on my feet, she was able to insert me. Arms around each other, we humped slowly while the tethered dinghies bumped gently at the dock and waves sloshed around under the planks. Somewhere, a fish jumped. We were alone in the universe.

She wrapped her arms around my neck and her legs around me. Holding her ass I was able to fuck her much harder. She seemed light as a feather. I released one hand to grab her ponytail, pulled her head back, and really went at it. The warm evening breezes swirled around us as we came. Then she kissed me hard.

We rowed the dingy back to the yacht, laughing all the way. I kissed her goodnight and tried to get some sleep. But at two o'clock on the dot, I was awakened by Trouble in her new crocheted bikini. She ran her lips all over me to little effect, snuggled up real close, and breathed in my ear, "I want to do anal."

"No you don't," I said.

She pushed out her bottom lip in a manufactured pout and said that her sorority sisters always asked if she'd done it. Of course she always said 'yes' but she wasn't sure they believed her. I asked, "Have they done it?" They say so, she said. "Do you believe them?" She wasn't sure. "Then I think you are in the perfect sorority," I said. "You have so much in common." The logic was lost on her. Also the irony.

"Possibly you have mistaken us for a couple of porn stars," I said. "I'm an exhausted grad student. You are a bright young collegian. I'm not going to try this a 2 AM." That seemed to put her off, but I was troubled that I almost liked the idea of ass-fucking her because she could be so annoying. Instead, to prevent further debate I said I had an idea, and I kissed her.

One kiss lead to another and pretty soon her lips were wrapped around my cock, while I lay on my back staring at the stars though the foredeck hatch. This was actually quite nice. Her cute little ass with the thong cord rocked with her efforts, there were quiet slurping sounds, and I was hard again despite myself. I pulled her top down and outwards so it was pushing her tits up rather than hiding them, and I let her continue for several more minutes, occasionally pushing in and occasionally reaching down for a twist of her nipple. I tried slapping her tit sideways and she said "Ohhh!" with pleasure and resumed sucking. I thought she felt this was sophisticated, so I did it some more.

Finally my conscience was bothering me enough that I felt I ought to fuck her. I pulled her up and roughly pulled off her bottoms. I slowly started to finger her, looking right in her eyes to judge the effect. She stared back and gave me some feedback by how hard she was squeezing my cock. After she was good and wet and I was good and hard, I rolled her onto her back and started slowly and teasingly fucking her, missionary. I braced myself on extended arms so I could continue to monitor her reactions. She was starting to mouth-breathe. I didn't know if it was real, but I took the moment to lie down on her, capture her left hand with mine and hold it over her head. I turned her partly on her side, moistened my right middle finger, slid it behind her, and felt around for her asshole. I pressed against it. She whimpered some more, so I worked my finger in up to the first knuckle and moved it around. She seemed to like that too, so I pressed and wiggled until I was in up to my second knuckle. I couldn't reach any further, so I ramped up the humping. Almost immediately she emitted a series of breathy "Aaah, aaaaahhhh" sounds, louder and louder. I had to clamp my left hand over her mouth. I could tell from her eyes that she was smiling. There was nothing that girl didn't like. She came, or gave that appearance, and briefly lay still. I wasn't sure what Miss Manners would say to do with my finger, but she quickly opened her eyes and said, "Stay in." We kissed, I moved my finger experimentally, and we gradually resumed fucking. It took her only a minute to climax, and then she rolled over, stuck her small pink ass in the air, and said, "Are you sure?"

I said I was and slapped her tight, pink ass pretty hard a few times. She said "Ohhh" each time, then wiggled her ass some more, but I fell on my side. I was exhausted. "You could give a girl a complex," she said. I told her she didn't need one.

THURSDAY

We set sail for an island with several small beach bars that featured music in the evening. Lingerie Liz got the Award in a walk just by wearing a bikini. The bottom was extra small and low riding with minimal cheek coverage, but in all fairness, the top couldn't be; that just wouldn't work structurally. She still showed oceans of bulging top-boob that sloshed around whenever she moved. She had to be careful winching in the sails, but she finally seemed at ease.

The mooring field was not well protected, so we arrived early, securing a mooring close to shore that would be easy for a bunch of drunks to find in the dark. We changed, dinghied ashore and started the party in late afternoon.

In a pattern I could now recognize, Liz sat next to me and we had an extremely interesting conversation about her research, gene editing, and the impossibility of paying for all the life-saving things doctors were learning to do. Despite the fascinating discussion, I just happened to notice she was wearing ultra-low rise Daisy Dukes and a blousey crop top with nothing underneath. Well, that's not well put. There were a couple of large, heavy things ranging around under there. They contrasted exquisitely with her bare, ultra-small waist, and I could hardly wait to get my hands on them. Neither could most of the other guys in the bar, I noticed.

We'd been at the bar for a couple of hours. The music was great but the sun was setting and the crowd got thicker and noisier. We could hardly hear each other. Liz came and sat in my lap. "Much better," she said. I agreed, but I now had a close-up of those spectacular tits, and I started to get hard. I was certain she could feel it. After just a little more conversation, she asked innocently whether I might want to go back to the boat a little early so we could be by ourselves. I said fine in the half-strangled voice I use whenever a lingerie model asks to be alone with me. But I pointed out that we only had one dinghy. "Let's swim!" she said.

She went over to Deirdre and whispered something. Deirdre gave me a worried look, but Liz hugged my arm and pressed herself to me. We stumbled out into the twilight and walked slowly to the dock. I was wearing my swim suit so I just dropped my shirt and shoes in our dinghy and dived in. Liz surfaced right next to me. We slowly swam to the boat and hauled ourselves up the swimming ladder at the stern. Liz's exertions were attractive to watch; her top was plastered to her body and now totally transparent. She would have won any wet t-shirt contest on the planet. We sat side-by-side in the cockpit to catch our breath and dry off.

"What do guys really find sexually attractive?" she asked, always the academic. I said I was sure the answer varied and I could only answer for me, but that in general it probably came down to satisfying some not-very-modern instincts for healthy, fertile reproduction partners. As a matter of evolutionary psychology, that was to be expected. Also, though, the modern male ego seems to require some boosting, since men can feel disadvantaged by an attractive woman's ability to trigger and frustrate a guy's sex drive so easily. So sexual enthusiasm was always a turn-on for me.