Sailing We Will Go - Cover

Sailing We Will Go

by Caesar

Copyright© 1999 by Caesar

Erotica Sex Story: A sailing trip means a chance to rekindle the marital fires for the husband, and revenge for the wife.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Cheating   MaleDom   Group Sex   Anal Sex   .

Copyright© 1995-2003

"There was a young sailor from Brighton
Who remarked to his girl, 'You're a tight one.'
She replied, 'Pon my soul,
You're in the wrong hole;
There's plenty of room in the right one.'"
-author unknown


The slight westerly breeze promised a wonderful start to a week of sailing. The six-year-old sloops sails caught the wind only moments after leaving the breakwater. The forty-eight-foot ship creaked as the wind pressed it to starboard and the few remaining unsecured items fell about below deck. Cold west-coast water washed over the side as the sleek craft came about to take full advantage of the strong breeze. It was a sailors wind.

May sat back in the cockpit on the port side where it was still relatively dry and watched her handsome husband pilot the craft expertly. Next to her, Susan, her best friend, clapped with happiness as the winds strength could be felt throughout the metal hull even while her inept husband followed the commands of the ship's pilot and captain, May's husband. The ship needed a crew, after all.

"Make fast those lines, Rob." May ignored the direction where her husband was pointing and just enjoyed the sight of him, a tall, strong, handsome man who had captured her heart and soul twelve years ago, from the short, black, slightly graying hair that caused him to look distinguished instead of old to the thick wide hands that could be gentle or strong, as he wished, and even the thick sturdy legs, which had caught the seas dance to become a part of the boat. There had not been many times in the recent years that May had sat thus, simply enjoying the sight of her husband. She could feel her strong emotions cause her sex to tingle with a familiar anticipation.

"With this wind, we'll reach the cove ahead of schedule." He spoke to no-one, or perhaps to the boat, his pride and joy for the last few years. Susan happily laughed and grabbed May's arm to share her joy at the wonderful news. Nothing at that moment would have been bad news, so enthralled with this new environment was Susan. May's husband looked at the giggling woman, then to his wife, a private smile passing to her. It promised a rekindling of the marital fires.

The cool wind and her husband's smile caused May's nipples to show her own anticipation and press outwards. Even while she looked into his deep blue eyes, she felt a simultaneous lust and hate for John, the man she married.


"God, I love it out here!" Susan continued to look out the slit window towards the coast, only a few hundred feet from the anchored ship, doing more talking than work; she had whipped the same bowl clean for almost two minutes. "I wish it could always be like this." She had said the same thing numerous times since the men went topside for a drink and talk.

May was polite. "Yes, it is gorgeous." Her best friend wasn't overly intelligent, nor was she street-wise, but Susan was the only remaining friend her husband had allowed May to have. With the last of the dishes washed, and May's job finished, she sat back to watch her friend slowly dry the remainder.

Susan was voluptuous, curvy, top heavy, whereas May was tiny, strong, and boyish. The two women were opposites, physically as well as mentally. The men had always looked at Susan, ever since they first met as teenagers. Susan was the classical blonde bomb shell, May the brunette bookworm, both attractive, perhaps May more so, yet initially Susan had always caught the boys' eyes first.

"I'm glad we were able to finally come out here to spend time with you guys." Susan so happy she was about to cry, with May's smile as her only response. "Things have been a bit rocky for everyone the last few months..."

To interrupt, as well as to get the weight of the next question off of her soul, May blurted out. "When did you last sleep with my husband?" It was spoken quietly but seemed to reverberate about the cabin. Susan lost her lively colouring and paled as she spun about to devote more quality time to the wet dishes.

After some awkward moments came the murmur, "I told you that was over with." May's silence seemed to weigh upon the shoulders of her best friend. "Almost six months ago," she finally answered. John had told May it had been over a year since his affair with his wife's best friend.

May knew the both of them were lying.

"You never told Rob?" Susan shook her head. This was the truth - May knew the overweight balding man had a temper, especially when he was drinking, and that her best friend was deathly afraid of it. May took a few steps and stood behind Susan, one hand coming to rest upon a soft shoulder almost to reassure the unfaithful woman.

"I hope Rob never finds out." Even while she said this, May's free hand snaked up the leg of Susan's shorts to find its way beneath her panties. Before the tall blonde even realized the extent of her friend's actions, the hand found its way to the natural crack between the wide soft buttocks. A single finger traced downwards then pressed inwards, forcing itself into the tight anal opening. May whispered, "Did he ever fuck you here?"

Attempting to escape the sudden violation of her person, Susan pressed forwards, her waist crushed against the counter and her torso almost bent fully over the stacked dishes. The blond realized it was useless to attempt escape, at least without her husband finding all out. More than anything else, Susan was shocked at her normally docile and warm friend's actions. Even the last question had not registered yet.

May roughly forced the finger deeper until the middle digit was almost completely immersed inside the warm dry hole. Susan grunted and whimpered as her friend pulled upwards, forcing the blond to her toes.

"Well?"

The tiny woman felt the sudden power that she held over her best friend, the surge of adrenaline that coursed through her veins. Her original plan was to question the last time her partner was unfaithful, not to assault her only remaining teenage friend. Yet when Susan had spun about, May knew. She knew they were still lovers and the two lying adulterers could not even get their stories straight. Something snapped and that cute saucy bottom that May had envied and that often taunted her, flaunted the sexy curves that had obviously attracted her husband. Without even thinking, she had rushed forwards and at that moment did not even know what the next few seconds held for either of them. She did know that she had agreed to this cruise only to confirm her suspicions.

"Yes! Yes, a couple of times." Sobbing, Susan clenched her body, allowing May to control the next move. "I'm so sorry, May. Really!" Obviously the blond was using a familiar voice to calm her best friend, a voice that May had never heard used on herself before, yet had been used on Rob often enough.

But May was not to be dissuaded. "Yes, I can see why John liked to fuck your ass. It's so round and cute." The hand that had been on the shoulder came down to pull the loose fabric of the shorts to the side, allowing May to view her hand upon much of the white buttock. "If I had a cock, I'd fuck you right now, too." To her own surprise, she meant it.

Once, May had agreed to anal sex with her husband, something she had always thought of as dirty. The single experience was disappointing, and painful. She never again tried, though knew of John's continued attraction to a youthful bottom.

There were a few awkward seconds before May asked, "When did you last fuck my husband?"

Perhaps Susan's will power had already crumpled by the sudden personality change in her best friend, and she quickly answered the question. "Wednesday, at lunch." May believed her, yet was surprised at the recentness.

She jerked her submerged finger. "Did he fuck your ass then?" Susan shook her head. "How did John fuck you?"

"The usual... Ouch!" May had moved her free hand up under the loose woolen pullover to grasp a full breast and tweaked her breast friend's thick nipple. She blurted out, "He likes me to suck him then bend over his desk." The bra was roughly pulled to the side, just enough for the nipple to poke out. May experimented with the touch of the rough hard point seconds before she pinched it viciously, knowing the pain would shoot through her best friend's body even as her nails bit deeply into the skin. Susan barely contained a scream and bit her lip instead.

"You're a whore, Susan!" was May's cold remark.

The larger woman was biting her bottom lip, almost to the point of drawing blood. May had known her friend was not too intelligent, and could see how men could be attracted to her physical beauty as well as her seeming mental dullness.

There was no longer any plan. Originally, it was just to find out the truth behind her husband's infidelity, but her actions had gone way beyond that. Disgusted at the buxom blond as well as her own actions, May rapidly withdrew her finger from the tight anus and quickly retreated back to the couch about the table.

Susan stood for a long while, grasping the counter in her hand while breathing rapidly. May watched in disdain - Susan hadn't even corrected her clothing. A white buttock and a pale breast still hung out. Finally, when Susan forced back her sob then began to correct herself, May interrupted her actions.

"Come here, slut." May had waited until the woman was again composed before speaking, and used a calm forceful voice.

Susan turned about and came towards her best friend, but could not look upon her.

"On your knees!" This time, May used more force in her voice.

Susan did as she was commanded. May realized her husband probably used the big-boobed blond very often in this role - she was a natural submissive and had a way about her that men must love to take advantage of her.

May slowly pulled her loose summer skirt up her long thin legs, her knees moving apart. Susan could not look upon her friend, nor did she even glance up at the tanned thighs that she always envied. Instead, she looked to the floor and began to shiver, though it was not cold. Finally, when the skirt was about May's waist and her knees widely spread, the smaller woman reached between her thighs and pulled the white cotton panty to the side of her crotch, exposing her sex.

"Eat me, slut." It was spoken so calmly, so gently that even May was surprised at the power she felt. Yet she was more surprised when Susan didn't even hesitate before leaning down to press her face against the near-hairless crotch before her. Unseen, a wet hot tongue gently trailed upwards from the anus to the top of her sexual gully and pressure button, her clitoris. Again and again the tongue continued the same path, while taking longer and longer each time at the top of the trail.

Grasping the mane of blond hair in a single hand, May gasped out in surprise - surprised that her best friend was following her directives, surprised that the use of *this* power was so easy, surprised that the tongue felt so good. Continuously, the tongue and lips continued to lick and flick gently, causing a delightful response.

May had never before felt the tongue of another woman. A male tongue was an infrequent visitor to that area, yet the expert technique of this woman was obvious. A woman knew how to please a woman, even one that was coerced into the act.

Seconds became blurred, then turned into minutes. The mouth worked relentlessly until the sexual heat of May's loins became a boiling torrent. The small dark woman held the blond head in both hands, pulling it inwards, unintentionally attempting to get the face inside her. One leg was placed upon the shoulder of the hard-working, voluptuous blonde, the other up onto the table.

May lost track of time as her desire exploded with a climax. Her body felt the wonderful feeling that radiated from her sex. The orgasm flowed freely, causing a her vagina to act like a fountain. Though May hadn't thought of it then, she would soon realize the orgasm given to her by Susan was better than any that her husband gave her. The biggest contributor to this fact, though, was the power she held over her friend.

The hazy mind of May began to return, with the gentle rock and creak of the sailboat, the light sound of Mozart on the deck, lips on her neck and a body pressed against her. She realized Susan was humping her naked thigh, squatting down over it while pressing her large breasts to May's. The small dark-haired woman took several deep breaths, gaining her strength back. Susan's crotch was bare and was rubbing a six-inch length of May's tanned, smooth leg, the skirt lifted up and the panties obviously discarded. While she relaxed, the larger woman above her began to pant harshly, her body sweating and wiggling frantically. Susan sighed and clenched as her own orgasm ran through her body and out of her wet cunt.

May pushed the tired woman off of her leg and onto her knees before her. Most of her anger had been drained from her body by the orgasm she had just experienced, though her heart pounded at the diabolical plan she was forming - a plan in need of the subservient help of her slutty friend.

Susan was kneeling between her friend's thighs, face to face, breast to breast; the sweaty vagina juice covered face radiated and shone. May leaned forward, taking the scared, tired face between her hands, licking slowly. Lapping much of the wet skin, May enjoyed the taste and feeling the juices gave her. She realized Susan was surprised, as well as turned on, by the simple action.

When it was finished, several moments later, May said, "Thank you, Susan." Her friend had a tear of regret and happiness forming. "I want your promise that you will do as I ask on this trip?"

Looking a little surprised, Susan replied with a simple, "Yes." She remembered the strong woman who shoved a finger up her butt. It was not the woman she had been friends with, but a stranger. One that was not totally unappealing.

"Good. Now go get cleaned up. The boys will be down soon." Susan tiredly got up and found her way to the fore cabin. May headed aft to take her own advice, and clean the encounters evidence from her body.


The boat was anchored with a stern line to shore near an islet that May's husband passingly referred to as "his" place. The gentle rocking and sway of the ship, as well as the active day, caused a deep drowsiness to dull the wife's senses.

May watched her handsome husband get ready for bed. He had left the door to the head open as he washed his face in the stainless steel basin. The water cascaded about his day-old beard as well as bead the tanned face that May had always found extremely handsome. As she silently lay there, waiting for her husband, the extreme range of emotions that flushed through her soul was the only thing that kept her awake. May felt a flush of heat to her loins remembering the feel of the tongue between her legs. The same tongue her husband had frequently enjoyed. Perhaps it was the transition of power that caused the vagina to tingle, or the feeling of control over another person that wet the sexual folds of the middle-aged lady.

In any case, the man May loved and hated was also the object of her immediate desire. In a dreamy state, the small woman barely noticed a hand casually cupping and squeezing the mound between her legs. Her own hand lent to the desire that flushed though her body.

Bare-chested, John could see his wife's reflection in the mirror as she watched him. The promise that this cruise would help light the marital fires seemed inspired as he watched his wife's own hand stroll across her crotch. Bringing Susan had been even more inspired, he thought.

Without a word, John turned off the dull light in the head, leaving only the moonlight through the open ports to light the room. Standing at the foot of the waist-high bed, facing his wife, he leisurely took off the rest of his clothing. Both of May's hands were now busy, one at her breast, the other over her sex while her eyes hungrily took in the sight of her handsome husband.

After the last piece of clothing was left upon the floor, John stood straight, facing his wife, his left hand finding and cupping his cock. May focused her eyes on this sight and became more aggressive in her own pleasure. The silk jockeys were quickly pulled aside and her fingers found the folds of her own sex wet and ready.

"God, you are beautiful, babe!" May sighed and her breathing became laboured after those words escaped from her husband's mouth. She flicked her clitoris gently from side to side as she wondered if those same words were spoken to Susan less than a week ago. "Spread your legs wider, baby, let me it all." She followed his directions unconsciously. What would John look like with the thick blond hair of her best friend bobbing up and down before him?

Perhaps John would ask her to suck him before pressing her over the edge of the bed to fuck, just as he did with the slut sleeping in the fore cabin? May fantasized about Susan's wet, warm tongue as it licked and sucked that hard cock her husband loved so much. Thinking these thoughts and knowing that that relationship was now in her hands got her very "hot".

Only moments later, John climbed into bed next to his sleepy wife. His strong hands easily removed the loose lingerie that barely covered his wife's sexy body. May felt his kisses as he rolled over above her, his hard cock finding its way to the familiar spot that they had both enjoyed over the years.

John spoke even as he finally entered her, "God! You're so wet!" The cock quickly submerged and ground deep inside the love channel. Without wasting time, nor with any preliminaries, John began a frantic pounding.

Other than breathing heavy, May had yet to make a sound. The quick and rough treatment that her husband was used to with her seemed to destroy the fantasy that the wife was earlier imagining, though that was partially her own fault, as their sex life in recent years was less than desirable - and in the last few months, it was almost non-existent.

"So fucking wet!" Again and again the cock drove deeply into her sex while the heavy hard body above her grunted and trembled with exertion. May knew her husband could last a long time without some stimulation from her, and though the idea repulsed her, she knew it had to be done. In a way, it also allowed her to control the situation, to hold all the cards in this marital bonding.

John was roughly kissing his wife's neck when she whispered into his ear, "God, you're so hard, baby!" She raked one of her clawed hands down his back, leaving a trail from her long nails. "Fuck me, babe, fuck me good!" Her tongue flicked his ear lobe. "Come on, baby, faster." She felt his hands force her knees further back almost to his shoulders. "Put your finger in me... in my bum."

This caused him to lose his rhythm and he pulled up to look into his wife's eyes. She spoke directly at him, "Finger my asshole, darling!" It had always been his fantasy as well as a fetish of his that she usually stopped cold. Anything to do with her bottom hole was off limits, barring that single time her coerced her into doing it. One strong large hand slid down her thigh to roll past her smooth buttock. Without hesitation a finger suddenly touched the hard muscle of her anus before pressing firmly into her.

There was a slight pain as the finger forced itself in, but it had its desired effect. Her husband was grunting with his activity, the finger up his wife's ass heightening his enjoyment. May bit her lip from the pain, then began to drive her hips upwards to meet her husband's thrust of both finger and cock. Effectively she was being fucked in both holes. She knew her husband was close to completion, while she was getting turned off by the whole affair.

To get to the climax of this session, May whispered, "Come on my ass, baby! Let me roll over - shoot on my bum."

John loved to watch his own pearl-coloured sperm drip upon his wife's skin, a fetish that he was not often able to enjoy. That, and the offered pleasure of his wife's gorgeous bottom was almost too much for the middle-aged man. He passed off this exuberance on his wife's part to the effort they both promised before stepping onto the ship.

Quickly he knelt up and watched as his enthusiastic wife rolled and turned to her knees. She quickly positioned herself with her round bottom raised high, giving him the perfect view of her two enjoyable holes.

The first touch May felt was the return of the thick finger to her anus, but this time John forced it deeply into her. All the way to the knuckle it drove, evidence that her anus was lubricated by her earlier self-enjoyment as well as the loosening that John had caused. Again and again, the finger fucked her ass; she controlled the urge to turn about and rake her hubby's eyes with her nails. A few moments later, she felt him slapping his cock against her taut buttock, preparing for his release.

This is what John loved, his beautiful wife allowing herself to be pleasured in the method that he wished. He pumped his cock faster as he felt the familiar tingle deep in his gut, even before the tightening of his balls forewarned him of his release. He wanted to shoot his come on the breadth of her bum, and even between her cheeks.

The hot sperm fell onto her sweaty skin, and May silently laughed as an idea floated into her brain. As her husband rubbed his softening cock across her bottom, rubbing in his sperm, she knew what she had to do next.


John felt the hardness between his legs and attempted to orient himself from his slumber. He was upon his boat, his pride and joy, and had fallen asleep after an enjoyable session of love making with his wife. He realized the hardness was enveloped by warm moistness that could only be a mouth, his wife's mouth. A soft tongue slid along the underside of his cock and over the head. May was working hard to please him, and John realized he was right not to leave her months ago. "Hummmm... !"

The mouth came off him for a second. "Morning, darling."

His eyes were not even open yet, but he knew he had slept in from the brightness beyond his eyelids. His desire for his wife rose considerably the more his faculties returned. "Sit on my cock, May." It was barely a whisper as his mouth was dry and hoarse.

Again the mouth came up from only a second. "I want you to come in my mouth." She returned to her work. After years of learning her husband's body, she knew the places to use her tongue to the greatest effect, the way he liked his balls to be squeezed. And the sloppy sucking sounds that came from her was music to his ears, she knew. "I love your cock, John, I could eat you forever." This and the knowledge that her husband hadn't shot his load into her mouth since the first months of their marriage should be enough of a catalyst to allow her to finish him quickly.

She was right.

John's sperm was soon spurting deep into her mouth while she didn't allow a single drop to escape and swallowed loudly. The orgasm, though smaller than last night's, was still powerful enough to exhaust the middle-aged man again.

When his cock was flaccid, May crawled upwards and into his strong arms, all the while her hand gently manipulating the soft member. Her come-smelling breath could be felt against John's neck and he moaned pleasantly. "That was wonderful, bunny." Bunny was his pet name for her. "I hope we didn't wake up Susan and Rob?" He smiled, proud of his performance as well as the events of the last few hours.

"I have something to confess, John."

He didn't like the sound of that; he froze. Was her confession why she was willing to put out the extra sexual effort for his pleasure?

"Susan and I made love yesterday." She smiled inwardly, knowing her gamble would work.

John felt his guts turn, then return to normal after hearing the words his wife had spoken. It took a few seconds for him to realize exactly what she said had meant. Then, instead of anger, he felt desire. A mental picture of his pretty wife and his mistress having sex caused his tired cock to jerk in response. It was like some fantasy, something he never thought could ever happen, yet the thought was certainly enjoyable.

Realizing his wife must be fearful of his response, and had proved her willingness to prove her love to him, he forced his voice to be stern. "How did this happen?"

Even though his voice hinted at anger, May felt her husband's cock twitch from the thoughts running through his head and she knew she had him according to plan. She whispered, "I don't know. I think it was mutual, and it just happened!" She sobbed. "I'm sorry, baby! It will never happen again."

Not wanting to push his anger too far, he pulled back some. "Did you enjoy it?" She only sobbed louder as a response, reflecting an affirmative. "Tell me what happened?"

May took a few deep breaths. "We were just talking and I kissed her, as a friend. And before I knew it we were frenching and feeling each other up. She took the initiative and ate me out." His cock began to grow. "I was too tired to do the same and Susan humped my leg until she came too." May hid her face in his shoulder, attempting to hide the smile that was creeping onto her face.

There was silence for many minutes as John considered the words of his wife. The more he told himself he should be mad, the more he was turned on by the image of Susan's blond mane between his wife's thin thighs. His middle-aged cock stood proudly at attention, even though it had only released its flood moments before.

John considered what he should do next. How could he tell his wife how much the thought of her and Susan fucking turned him on? Yet she was sobbing against him, and he wanted to use her feelings to better his situation. Her leg had arched up and came down over his torso, and as he thought of what to do his wife slowly rolled upon him. He smiled when he figured her guilt was so great she was willing to do anything he wanted, as long as he played his cards right. Perhaps he would even get to fuck her in the ass again. Or a more exciting idea was watching his wife and his mistress lick each other before joining in.

May felt the hardness between her thighs and wiggled expertly downwards to impale herself onto him. This time she desired the hard pole inside her. She was going to enjoy this fuck. Perhaps it was the feeling of power she felt over her husband, and yesterday over Susan, that was bringing on this surge of sexual need. Still hiding her face, while pretending to sob infrequently, May felt the rock-hard cock slide deeply into her.


Susan awoke with the sharp pain from her vagina as it was being pierced. Someone had lifted up her nightgown and was now pressing something into her.

Rob held his wife against him as he felt his cock enter her dry hole. Facing sideways, away from him, with her knees lifted up gave him great access to her sex. Usually he was an "on top" kind of guy, a conservative lover who demanded sex whenever he felt in the proper mood. His wife's mood didn't matter. Yet, this morning, he was wakened by the sound from the stern cabin. The sounds of fucking.

He could hear the whimpers and cries of desire from May as his buddy properly fucked her. There was also a slight rocking to the boat, irregular and too fast to be waves, as the two of them coupled only forty feet away. It was natural that Rob was attracted to the tiny, pretty, quiet woman, and had always fantasized what it would be like to have her legs wrapped about his waist instead of his wife's.

The buxom blond was very attractive, yet Rob was tired of her. He felt like a strong, handsome man who deserved a woman like May, not the big-breasted, dumb wife he ended up with.

Susan realized where she was and who she was with. Considering her on-going affair with John and the recent entanglement with May and her own limited intellect, it was a feat to figure who was behind her while the haze of sleep still controlled her senses.

Anything sexual turned Susan on, and soon even this intrusion excited and lubricated her sex which allowed faster and easier penetration by her husband. And though Rob didn't like her to make too much noise, she could not help panting loudly. It was a treat for her to have sex with her husband in any other position other than the classical missionary, and this turned her on.

Yet what turned her on more were the thoughts running through her head brought on by the sounds of enjoyment in the rear cabin. Her lover was having sex with his wife, the sounds of that coupling easily discernible. And she could bring up the image of May's wet vagina and pussy that she intimately knew, and of the familiar cock. In her mind, Susan was back there with the two of her friends, watching and waiting for her turn. Her fantasy enabled her cunt to dampen considerably, and even heighten Rob's enjoyment.

Only a few moments after entering his wife, his orgasm exploded from his cock, which ended his wife's fantasy and enjoyment. "Morning, Rob", she whispered, surprised he had lasted as long as he did.


The weather that morning was perfect to continue sailing, yet turned ugly in the afternoon. The wind went up a few notches as did the sea state. Sailing up the Strait of Georgia, John made the decision to run back to shoreward and find another cove to wait out the weather.

 
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