Captain Coo's Cruises

Author's Note: This is a five part story and, although each part might be read without reading the others, reading all parts gives a little better understanding of the whole story. I wish to express my profound thanks to Literotica's most gracious (and lovely) Copperbutterfly for her time and effort in editing these stories to make them more enjoyable reading.

*

The Wednesday after my most memorable cruise with Eleanor DuPort brought no business so I was back on deck Thursday morning swabbing an already clean deck when toward eleven o'clock I received a hail from the pier.

"Ahoy, the Lady A. Are you the captain?"

Again it was the voice of a lady, although this one was taller and appeared to be older than Ellie ... probably early sixties, I would guess. She was dressed nearly the same as Ellie had been, in shorts, blouse over tank top, deck shoes and straw hat, although her hat was much broader brimmed than Ellie's had been. When she took off the hat to address me, her silver hair flowed out from under the hat, blowing in the light breeze.

"Yes, ma'am, I am Captain Cook," I responded.

"Is your boat available today for a day cruise?"

"Yes, ma'am, it sure is," I replied.

"All right to come aboard?"

"Yes, ma'am. Here, let me help you," and I extended my hand to steady her.

"I'm Trudi Rockefeller," she offered.

"I'm Tom Cook, ma'am. Will anyone else be joining us today?"

She laughed. "Oh, no, my husband's far to busy to bother with a little of' outing with his wife. He won't be home from work until sundown."

When she was on board, I gave her the scenic tour of the boat. She picked one of the forward deck chairs to settle in and watch the beginning of our cruise.

"What kind of cruise did you have in mind?"

"Well, I'd like to sail up the coast a ways, then maybe out to sea for a while and whatever it takes to bring us back. And I hope to see as pretty a sunset as Ellie DuPont saw Tuesday."

"Oh? You know Ellie?"

"Ah, yes, she's my good friend."

"Would you like something to drink before we start?"

"How about a cup of coffee with a dollop of gin?"

"Coming right up."

I hurried below and prepared the drink, took it to her and then went to the pilot station to prepare and set the cruise plan.We would follow the coastline to the east by northeast on the slowest leg for about five hours, turn southeast for a run of nearly two hours and then sail the fastest leg back to the west-southwest in around four hours, giving us a good view of the sunset.

After making sure she was settled in, I cast off and backed out of the slip, then we motored through the harbor and out into open water. Once we were clear, I set the sails and killed the engines, just for the thrill of it, before I set the autopilot on. After making sure all the electronics were working, I went fore to see if the lady needed anything.

As I came around the mainmast, I was surprised. She had removed her blouse, shorts and tank top in favor of a bikini ... at least the bikini bottom. Her rather bulbous and somewhat sloping breasts were uncovered, a condition they seemed to be used to considering her overall tan.

She caught my reaction and said "I hope you're not offended, Captain. I like to expose my body to a lot of sunlight."

"No ... no, ma'am, I'm certainly not offended. Surprised, maybe, startled yes, ecstatic, absolutely but offended ... no, ma'am."

"Good. But, Captain, I do need some help."

"Yes, ma'am. What can I do?"

"Would you rub some of this sunscreen on my backside?"

She got up and went to one of the mats amid-deck and lay face down, handing me a bottle of lotion. I knelt beside her and squeezed some of it around her shoulders and upper back, then smeared it up to her hairline, down along each arm and along her back and sides. My hands rubbed against her breasts, mashed out to her sides as she lay on them. When my fingers rubbed circles around the soft flesh, she made no sign of recognition. I moved on to her middle and lower back, covering all the flesh that I could reach.

When I was beginning to wonder what she wanted me to do next, she raised her middle, pushed the bikini bottom down and worked it off her feet. "Please cover it all, Captain" she spoke into the mat.

I thought, "What better way to do this than from behind her;" so I shifted so that I was straddling her lower legs, then poured lotion on her bottom and backs of her thighs. I leaned into the task of rubbing it into her skin with both hands, loving the feeling of a woman's soft flesh under me. She may have been soft in one way but it was not because she was out of shape ... I could feel the muscles in her legs, probably a jogger or maybe a tennis player.

I started to move further down but her voice stopped me. "Captain, I don't want to burn any part of me. That means you have to cover it all. You know what I mean, don't you?"

"Yes, ma'am," I replied cautiously.

Again I poured a thin stream of lotion around her buttocks and then concentrated on spreading it ... by spreading her globes and covering all surfaces. I smeared the sweet smelling lubricant right up into her anal valley, only to hear her moan sensuously. Moving on around, I covered her upper thighs more generously, frequently letting my fingers touch the puffy outer lips of her pussy, eliciting more and more soft moans.

On impulse I poured another gob of lotion in my right hand. Spreading her buttocks with my left hand, I spread the goo over the centermost part of her puckered opening and began rubbing it hard. In just a couple of minutes, she tossed her head back and groaned, "Yes, baby, do it!"

Retracting all but the middle finger of my right hand, I pushed that one into her opening, working it back and forth, in and out until the opening became softer and let more of my finger enter until it was all inside. Her bottom was squirming back and forth as she urged me "yes, honey, I love it!!!"

A few more strokes and she was urging, "Fuck me, please."

She reached behind her and spread her buttocks with both hands. I doffed my clothes and smeared a gob of the lotion on my throbbing spear, then poised with it at her opening. As I slowly pushed, the opening gradually accepted the purple arrow.

I paused for a moment to let her recover but she hissed "Come on, sugar, fill me up."

I began using progressively longer strokes until my crotch pressed against her broad bottom. I rested my lower weight on her ass, propped myself on my elbows and wormed my hands under her breasts. Then flexing my cock inside her bowels, I massaged her tits for a long time while I kissed up and down her neck, first one side and then the other. Before I finished, she was moaning and wiggling her ass and bobbing her head back and forth as she muttered encouraging words. I tried to hold back but felt my balls contract and suddenly I was shooting a load of hot jism into Trudi's bowels. As I was emptying the last of it into her, she grunted that she was cumming and began shaking like a leaf in a fall wind.

Ungentlemanly though it may have been, I collapsed on her, empty and spent, still kissing her and now squeezing her tightly in my arms. She replied by frequently flexing her anus on my deflating member. Finally it plopped out of her and I rolled off to the side, weary but very happy.

A few minutes later, she twisted so that her upper body was lying on my chest. After a few more hugs and kisses, she said "Gawd, that was good. How did you know?"

"Know what?"

"That I loved to be fucked in the ass."

"Oh, I didn't, but I sure hoped you did. I liked the way you reacted to me rubbing in the lotion and ... well, I just couldn't help myself."

"Good. I'm glad, 'cause it sure did wonders for me!"

She laughed but there was a bitter sound to it. "I wish I could make my husband understand how good it can be. He thinks it's dirty and won't touch me there. We did it once, maybe 35 years ago, and he couldn't wait to get into the shower. Now he ... he hardly ever wants to have sex."

"Ouch. That's too bad."

She giggled. "Yeah, it is. Life is so much more fun if you get fucked every so often. Come on, sugar, let's go get a shower. Ya never know when we might want to do something else."

She tweaked my flaccid penis and then hurried down the steps and disappeared into the main salon. She seemed to have a bounce in her step that hadn't been there before.

We used the shower off the master bedroom since it was tub-sized and large enough for the two of us. I started soaping her back and shoulders, but she grabbed the bar and said "Me, first."

She began rubbing the soap all over my chest and stomach but, while my cock anticipated her attention, she ignored it and turned me sideways so she could soap my back with one hand. When she got down to my rear, she soaped both cheeks well and then began rubbing her fingers into my anal valley. She withdrew her hand to rub the soap bar again and when her hand returned to my body, her middle finger unerringly went right up my anus.

I could feel her fingertip against my prostate gland and my legs almost folded up from the pleasure. My cock, which had been semi-erect, went completely rigid. After her finger had probed for a few seconds, her left hand found my scrotum and gave it a serious massage before moving up to my shaft. For the next several minutes, her left hand stroked and twisted and pulled on my cock while the finger up my ass teased and poked and prodded. I had to lean against the wall for support.

And then it ended! With me standing there facing a wall, my cock spurting long strings of white sticky cum while her hand roamed up and down my shaft, finally engulfing my balls once more and carefully milking them of every last drop while she cooed as if she had cum herself.

I tried to grab her, wanted to somehow return the favor but she fended off my hands, saying "Uh, uh. I just always wanted to see if I could do that to a guy but never had a chance. Let's finish the shower and get back on deck, okay?"

"Sure. Whatever you want," I replied.

She laughed. "You'd better not say that so quick. You never know what I might want."

On the way back topside, Trudi rummaged through my galley fridge. I offered to cook for her anything she would like but she didn't want anything like that. She surprised me by selecting some things and making a rather hefty sandwich for both of us while I picked up a couple of canned drinks for us.

Trudi asked me to sit with her on the foredeck and enjoy the sea breeze. So we passed another hour watching the waves, some distant activity on shore occasionally, and twice flaunting her exposed breasts at passing fishermen, who got a charge out of seeing a big pair of hooters in the sunlight.

By the time we turned south-southeast into the second leg, we had both had enough direct sun and moved into the shade of the bimini, which let us enjoy the breezes without all the heat. Sprawled on a couple of padded benches, we talked ... mostly she talked and I listened. She told me that, although she had come from a wealthy family, her marriage had been arranged with the Rockefeller family for social reasons and she'd had little to say about it.

Nevertheless she had come to love her husband and they seemed to have a pretty good marriage for a while, although she thought he was a little more formal with her than he needed to be. She had a wide variety of acquaintances for social get-togethers but really very few friends. In fact she thought that her only true friends were Ellie DuPont, Martha Gettys, and Claire Davis. Although there was a disparity in their ages, she said that they bonded because of common interests and compatible attitudes.

Trudi told me that, as the years passed, she and her husband simply drifted apart. While living together, they did virtually nothing together except attend social functions. Trudi and her friends gathered frequently for card games and friendship, mostly the friendship because they all fell into the same category as Trudi ... stranded from their spouses, who were primarily married to work and their fortunes. Only occasional short outings that passed as vacations interrupted their routine.

As she talked, she had almost absentmindedly slumped on the bench, eventually putting a foot over the arm at the end of the bench. Her right hand drifted down between her legs and she almost imperceptibly began to rub her mound. I watched and listened as she talked until I could stand it no more.

In one step, I crossed the gap between us, lifted the leg dangling on the floor to my shoulder, and replaced her fingers with my mouth. I started kissing all up and down her thighs and into the depths of her dripping wet pussy. Within a few minutes she was almost as wet as the seas we were sailing through and in a few minutes more she was gushing fresh cum as she clamped her thighs onto the side of my head.

When she was breathing a little calmer, I pulled Trudi and the cushions off the bench onto the deck. Lifting her unresisting legs to my shoulders, I guided my spear to her sloppy opening and pushed slowly. The soft tender flesh parted easily as my shaft buried itself to the hilt in her love tunnel. She offered me her big titties, holding them upright with both hands, to massage and tweak while I pumped her pussy.

I worked her legs around in different positions and her facial expressions rewarded me for my efforts. Three times, Trudi gritted her teeth, stiffened up like a board and quaked through waves of pleasure as an orgasm overtook her. Just after the third one, my nuts seemed to grow, then pulled up toward my body cavity and began shooting hot sticky sperm into her velvety sheath. It was an exquisite feeling as shot after shot passed between us.

When my balls were empty, Trudi pulled me down on top of her and said, "Oh, honey, this has been one of the best days of my life. You are so-o-o sweet." We spent the next few minutes swapping spit.

With the change of course onto the third leg and some overhead cloud cover, we went back to the sundeck for a while. Being in an open sea with only the sound of the wind in the sails and the occasional slap of the sheets makes for a very relaxing time.

Trudi probed me for information about my background so I told her about growing up around the water all my life while my father worked trying to run a commercial fishing fleet of three boats. It was hard work and I helped when I got big enough. Even when I went to college at a local school, I worked part time as an outfitter after classes, working each afternoon to ready the boats for their early morning departures the next day, repairing equipment as needed, and generally making myself useful.

We went into the galley, where at her request I whipped up a big bowl of chef's salad and we ate as she continued asking me questions.

I learned to love the sea at a very early age but also learned a healthy respect for it. During my high school years, my brother and an uncle were making a harbor crossing in the protected waters of the bay when a squall caught them unprepared and capsized the boat they were in. They both were entangled in the netting they had used that morning and were in the process of stowing but drowned before they were able to free themselves.

Still I considered myself fortunate to be able to make a living on the sea. I loved how it could take you anywhere you wanted to go, provide food to eat and, with the proper preparation, water to drink. It could challenge your skills and provide the most relaxing atmosphere imaginable. It would warm you up and then cool you down. It was, to me, a complete world.

As time passed, I kept noticing Trudi squirming around trying to get comfortable, but mostly I noticed her broad round bottom and felt myself growing hard again. With sunset about an hour away, I got to thinking about having another piece of her.

I didn't ask but went over and straddled her legs. With a hand under her waist, I lifted her to her knees, spread her legs so I could kneel between hers and began working my now-stiff probe up between the soft outer lips to her hidden temple. She was moist and it didn't take much effort to slip my cock into her pussy.

Trudi laid her face sideways on her crossed arms and said "Ummm, honey, that's nice."

It's amazing how little ol' six foot waves can make for movement between a man and a woman so connected. I held her hips and as the boat crested each wave, Trudi seemed to be pulled forward as I was pushed back, pulling my cock part way out of her. As the boat slide down the shallow trough, she was pushed back while I was driven forward, forcing the root of my tuber against her soft receptive twat. It took no effort on the part of either of us, although I couldn't help but reach out from time to time and massage a handful of her oh-so-lovable hooters.

The first streaks of sunset were showing in the west when my balls emptied. It had been a long and slow fuck but very rewarding and satisfying. We lay side by side and watched most of the rest of the sunset, although I got up and went to the pilot station as we neared the mouth of the harbor. I wanted to monitor our progress and safety.

Meanwhile Trudi went below and dressed before bringing me my shorts. Then she stood close to my side while I took control at the harbor mouth, lowered the sails and fired up the engines for the trek across the harbor to the marina.

When I came back onboard after tying up to the deck cleats, Trudi called me into the salon. She handed me an envelope and said, "I think this will cover the cruise and I must say it is money well spent. I feel great, honey. Oh, there is one thing though. I was wondering if ... maybe ... you would like one more piece of my ass before I go ...?!?"

We were soon naked again on the bed, her on her back with her knees nearly touching the sides of her face as my ever-ready dong pierced the tight opening between her buns. Trudi had said she loved anal sex and she proved it, cumming in just a few minutes and then helping me change our position. We rolled both her legs to her left without ever removing my rod from her ass. A few minutes later she was howling about cumming again.

After that I rolled her again until she was on her knees, her face flat on the mattress. As I plunged into her over and over, I remember thinking to my regret her tight little opening had become more slick. The opening was less tight as I fucked her and she kept relaxing the muscle around the opening. She came again and I rolled her to her right side, straddling her bottom leg while extending the other to her front.

In a few minutes she began moaning "ohgawdyes ... ohgawdyes ... ohgawdyes" and then she climaxed again. I rolled her over on her back again and worked her legs like a bicycle rider. In a few minutes I felt my own orgasm approaching and tried to hold it back until she came once more but it was a futile effort. I shot my load of cum into her rectum, feeling the wonder of a fantastic release ... and then Trudi topped it off by cumming one last time.

She was still a little rubbery-legged as she came to the gangway to leave. I reached out to steady her and started to kiss her but she stopped me. "My chauffeur is in the parking lot and I don't want to give him any more to talk about. Will you save the same time for me next week?"

I shook her hand, all I could do under the circumstances, and said "Yes, ma'am, any time you want."

"Well, then, book me for Thursdays this season. I'll call if I can't make it. Oh, and Captain? Don't be surprised to see those other friends I mentioned. The way Ellie talked about you, we all wanted to meet you. And now that I have, you'll get my recommendation."

"Thank you, ma'am. I appreciate that."

"It's worth it, Captain. You run a tight ship."