A Boating Gang-Bang

Until this morning, it had not been a good week for Jack Palmer, Attorney at law. Increasingly urgent demands for overdue alimony from his bitch, ex-wife found their way almost daily to his small, two roomed office. One of his few clients was threatening to take her business elsewhere if he did not soon produce some results on the impending case against her wayward husband and, as usual, Cindy his secretary and general nemesis, argued with him over insignificant matters such as unpaid telephone and power bills. Although he couldn't complain too much about Cindy.

Ah, the lovely Cindy, he thought. She might be a bitch at times, but she ran his office with a diligence to be proud of - plus she had one extremely redeeming factor: her husband. The sap hadn't touched her in over a year and this had left the way clear for Palmer to sample the delights of her glorious body on regular occasions. He felt a stirring in his loins as he recalled their activities the previous evening before leaving the office. Cindy's breasts were wonderful and, after he had pleasured her sweet pussy with his tongue as she sat open legged and pantyless on his desk, she had allowed him to slide his extremely hard tool between those spectacular mounds of warm flesh until.....but Palmer couldn't think about that now. The post that morning had delivered a very pleasant surprise from his uncle that had brightened up his day and immediately dulled the alcohol induced headache obtained late the night before at Big Joe's Bar and Grill.

Palmer had been working for his uncle Tony for the past eleven months now; laundering his money and receiving a healthy cut for himself. For years he had dreamed of walking away from his declining business and marital problems, buying a boat and just bumming around the islands. He had calculated that he needed in excess of a million to do this and the confirmation of this latest money wire now made his dream possible. He called his bank and checked the balance of his secret account. Quickly put through to the manager, he was politely informed that he currently had in excess of one million, two hundred and fifty thousand with the funds that they had received that morning. Palmer thanked the manager and replaced the receiver. It was now or never, he thought. The time to leave had come at last! He thought about how much he would miss his life here in the city. The answer came quickly: Not much! He did have reservations about leaving Cindy however and, not for the first time wondered about asking her to join him - it would be good to have her aboard and the thought of continued indulgence of her charms sent another tingle through his loins. But Cindy was a city girl at heart and he knew that she would have trouble adjusting to the life he had planned. Anyway, she had never shown any signs of wishing to leave her old man and Palmer doubted that she would have agreed to his request.

It was 9am now. Cindy would not be in for another hour. It wasn't the way he would have wanted to do it, but writing her a note, currently seemed the best idea. Stuffing two thousand into the envelope for expenses along with the note and another two thousand for herself, he left the hand printed envelope on her desk and walked out on his life forever.

Cindy arrived that morning to an empty office. This was not unusual, Jack often slept off a hangover until late in the morning, but this particular morning the place seemed a little too quiet, a little too still. She didn't notice the letter until after pouring herself a coffee and lighting her first Marlboro of the day. Cup in hand, she sat behind her old wooden desk and drew deeply on the cigarette. The envelope, bearing her name in Jack's handwriting appeared through a cloud of blue smoke. It was not until she had completed reading the second paragraph that her boss' intentions became clear.

"Shit, Jack!" she said out loud "I never thought you'd actually do it!" She completed the letter and re-read it. There was no doubt. He was gone and she was out of work! She felt happy for him but a little angry that he had not confided in her. Oh, how she wished he had asked her to join him. They had a volatile relationship, she knew, but the thought of losing his lovely big cock was almost too much to bear. Sex between them had been fantastic. A little adventurous maybe: they had done things in the small office that she had never even dreamed of - even in the days when her husband was interested. She was smiling as the thoughts span though her mind but a small tear rolled down her cheek and splashed onto the page she had just finished reading - a tear of happiness for Jack, or a tear for a lost lover? She couldn't tell.

Six weeks later saw Jack Palmer, ex-Attorney at law, sitting outside a harbour cafe sipping cold beer straight from the bottle. His recently purchased boat, a forty foot Bermudan rig, had run into a few problems just off the coast of this island, the name of which currently escaped him. Not major problems, but bad enough to have to put into shore and arrange for repairs. The dark skinned owner of Rick's Yacht Maintenance had assured him that, after receiving the parts that were required from the mainland, his boat - Anna Free - would be ready to sail in a day or so. Jack didn't mind too much. A shore break was due anyway and it allowed him time to sample some of the local beer and stock up on provisions.

The bar was less than crowded: a few locals sat around drinking tea or beer, playing Chess and smoking potent smelling cigarettes. Jack had not smoked for over ten years, but since starting his new life he had missed the constant aroma of Cindy's Marlboro's that used to hang thick in the air of his old office and had bought a carton on a whim before leaving. He had found the taste and smell somehow comforting and, as he lit up now, he closed his eyes and though of his ex-secretary. He had not been laid since setting sail six weeks ago and it had not been difficult in that time to summon up an image of Cindy in his mind. This time he had her on her knees in the classic "doggy" position. Her bottom was tilted delightfully upwards and she accentuated his daydream by wiggling the rounded cheeks at him tantalizingly. His eyes screwed tighter shut and he could almost feel the contours of her soft skin as his hands passed over her body. Her breasts, her arms, down across her back and over her ass, massaging the ....

"Hello! You don't look like a local." Palmer heard the friendly voice close to him. It was one of the very few English speaking voices that he could hear around him and so assumed it was directed at him. His daydream broken, Jack reluctantly opened his eyes and stubbed out the half smoked Marlboro. He looked up and squinted into the bright afternoon sun.

"Sorry to disturb you but we saw you come in a few days ago. Yours is the Anna Free, right?" The voice was male and sounded as if it came from Jack's part of the world - or at least close. As his eyes adjusted, Jack could now make out the man standing in front of him. Actually it was a couple, but the woman, attired in a light, wrap-around dress that he could almost see right through, had not spoken yet.

"Do you mind if we join you?"

As Jack posed no objections to the man's request, the three sat together and ordered more beer. Jack had been right about the accent. John, as he had introduced himself, and May, his wife, had lived less than a hundred miles from Jack's old office. Apparently, John had lived there all his life, but his wife was of oriental descent. Jack had little time to look at his male companion, his whole attention was taken up by May. Although petite, the wrap-around dress did little to disguise an exquisitely curved figure. Her high breasts were unfettered by a bra and he could clearly see the dark, cherry red buds of her nipples through the thin fabric. The hem was high enough to afford him a spectacular view of her slender legs and she wore open-toe sandals that revealed nail polish to match that of her slim fingers. Jack was captivated.

The trio talked well into the evening. Jack discovered that he and John had quite a lot in common - they had both been lawyers in a previous life and both were just mooching around the islands- and the conversation flowed easily. As more and more beer passed Jack's lips and began to loosen his tongue, he heard himself ask the couple if the would like to accompany him to the next island when his boat was ready.

John smiled at him. "That would be wonderful, Jack, but you hardly know us. Are you sure?"

"Yeah, why not!" Jack slurred as yet another beer was deposited on the table by a very happy bar owner. "It's only to the next island. Two day's, right?"

"That's very kind of you, Jack," said May with a sweet smile, "We would love to join you for a few days!"

The following day Jack found the "Anna Free" ready and waiting to sail. After counting out the unfamiliar bank notes to Rick of Rick's Yacht Maintenance, he climbed aboard and, head pounding with hangover pain, started to make ready to leave. He wondered if John and May would show up. There had been a lot of talk last night and he seemed to remember very little. He knew that he had asked the couple to join him, but now regretted it slightly. He was used to his own company but he had to admit a distraction in the form of the beautiful May, would be most welcome. The tide left at four that afternoon and, with or without his new friends, Jack intended to sail on it.

They arrived at three thirty. Jack had finished his preparations almost an hour before and was sitting on deck sipping his first beer of the day.

"Hello there!" called John cheerfully as he and his wife wandered up the dock.

Jack waved back but again his eyes were on May. The wrap-around dress of the night before had been replaced by a light, yellow skirt and bikini top. The late afternoon sun still burned brightly, low in the sky behind her and Jack could see right through the skirt. He strained his eyes as they approached, but try as he might, he could detect no sign of a panty line! Had this wonderful looking woman arrived to board his boat without underwear? The thought stirred an almost forgotten feelings in his pants as he helped them both aboard.

After showing John and May to the forward cabin - the only space large enough to house a small double bunk - Jack cast off. The late afternoon was still warm and, shirtless with knee length shorts and barefoot, he piloted his craft expertly out of the small harbour and into the ocean. After setting the sails and settling the boat into a long, meandering tack, more beer flowed. The three friends laughed and joked as Jack taught John the basics of boat control under sail. John learned fast and was soon the boat was speeding with full sail under his sole direction.

By nine that evening, Jack felt happy enough and drunk enough to allow John full control of the craft while he, Jack, slipped into his bunk for a couple of hours sleep. The sound of the calm waters lapping at the hull always had a mesmerising effect on him and, within a few minutes he drifted off to thoughts of May and Cindy. His dreams were wild and vivid, alternating between Cindy's voluptuous figure and May's petite body in a variety of situations with himself as the central theme running through them all. His own dream body reacted perfectly to both women and had them screaming their pleasure as he rode them both deeply and fiercely.

At nine thirty that evening Jack woke with an aching erection. He shook his head as he climbed out of the single bunk as if trying, reluctantly, to rid his mind of the still vivid dream. This would never do, he thought. He'd only met the couple the night before and already he was fantasizing about fucking the guy's wife! The stars were bright and the moon shone down, bathing the still ocean in an eerie half light as Jack climbed silently up through the deck hatch. He could hear sounds coming from the wheel house of the boat and could see the silhouetted figures of John and May inside. As he neared them, his bare feet making no sound on the deck, he was suddenly aware that, whilst John was still in control of the boat, his beautiful wife was moaning in what could only be described as ecstatic tones.

Keeping low and out of sight, Jack crept closer. His mind screamed to him of the virtues of personal privacy, but he couldn't help but follow his erection. Cautiously he peeked in though the wheel house window. He saw John first: one hand still on the wheel but with the fingers of the other firmly planted between his wife's legs. May was completely naked. Her arms were tied with cord to beams on the wheel house ceiling and her ankles were secured likewise to the floor with her slender, olive skinned legs set well apart. Jack was close enough to hear wet, squelching sounds as John's fingers thrust hard in and out of his wife's body. By the sounds of her constant moaning, being restrained in this way was obviously not something that May objected to in the least. In fact quite the reverse. Her head was back, her long, black hair falling in sweat dampened tresses down her back as she shook and trembled her way through a shattering multiple orgasm.

As May's moans and gasps began to subside, Jack looked back towards John. He hadn't noticed before, but John's large, erect cock was sticking out through the open fly of his shorts. As Jack continued his voyeuristic adventure, he saw May's attention was also drawn towards her husband's inflamed appendage but, tied as she was, she could do nothing but look.

"Mmmm...oh, let me suck you, baby," she moaned as she writhed in her bonds. "Let me suck on that big, juicy dick!"

But John was having none of it, he was the one in control. He called the shots. Taking his time he checked his course and set the automatic steering before turning back to his squirming wife. Jack watched him rub his cock swiftly a few times, ensuring that it was at full attention. He moved in front of May and turned her body. Jack almost let out a cry of disappointment as he lost sight of her beautiful frontage but caught himself just in time. His hand was inside his own shorts now. He couldn't help it, the sight of these two was proving too much for him. If he couldn't have her, he was going to jerk off watching her butt while her husband fucked her!

Jack felt the head of his cock and squeezed gently. Mmmmm, he almost sighed out loud as a blob of pre-cum appeared at the tip and glistened in the moonlight.

"Aahhhhhhhhhhh" May moaned again deeply as John pushed his tool into her wet pussy. Jack gasped and held his cock as he watched. This time he had gasped audibly and cursed himself as John looked over his wife's shoulder straight at him. Damn! Jack thought, busted! But John showed no signs of stopping what he had started. Jack saw a smile creep over his face and then whisper into May's ear. In a second, may's head twisted round to also look at Jack. She too smiled and then spoke.

"Don't waste it in your hand, Jack," she said as if she were doing little more than buying a morning paper. "Come on in and join us!"

Jack thought about checking his watch to make sure it wasn't his birthday! But his legs had already decided to move him into the cramped area of the wheel house.

"Hi Jack!" smiled John, his cock still buried inside his wife's vagina, "How about a sandwich? You know, it's May's favourite. Come on buddy, you've been eyeing her up from the first moment you saw her. Now's you big chance! It's not the first time I've shared her you know."

"Y..y..you mean..do her in ......." stammered Jack hardly believing what his new friend was telling him and half wondering if he were still asleep and dreaming.

"That's right, my friend....put it in her ass. She will love you for ever if you do her hard and fast!"

"God, Jack. Yes do it. Do my ass while John fucks my pussy. Mmmmm...oh yes...I want you both in me!"

With so much encouragement, Jack could hardly refuse even in the most unlikely event of him wanting to. Manoeuvring himself up behind May he felt his exposed prick squash against her soft buttocks. He gasped at the touch and as John lunged into her once again from the front, he lost his balance momentarily and fell back against the wall. John and May laughed, not unkindly, but Jack bristled with embarrassment nonetheless. Picking himself up, he was determined to put up a good performance. Yanking his shorts down to his ankles he held his throbbing member in his hand. No need to rub it as John had done - it was already engorged and throbbing wildly. He spat into his hand and coated his glans with the produced saliva. Not the sort of thing that he was happy to do, but with a lack of any sort of lubricant, it was the best he could come up with.

May and John were both moaning deeply as they fucked. May's butt was just inches from Jack's prick now, but with the movement caused by John's thrusts, it was difficult for Jack to keep her still. Visions of Cindy, on the floor of his old office, her bottom in the air just waiting for him to drill her tiny hole, filled his mind as he stabbed his tool at May's ass. The first attempt missed and produced another giggle from the heavily panting oriental. Another try. This time he aimed straight. May gasped out loud as his cock speared her back opening and then screamed in ecstasy and pain as he entered her anal tunnel.

Jack was wired. High on life and sex. He butt-fucked her hard and fast as John began to do likewise with her pussy.

"Mmmmm, go on Jack. Ream her ass while I fuck her wet cunt!" he cried through gritted teeth. Jack could tell that his friend was close to cumming.

"Oh, yes....your wife's ass is so tight, man." he replied, getting into the part. "I'm gonna coat he with my cum soon!"

"Ahhh..yeah, me too Jack. I'm almost there!" May was caught as the filling in the sandwich. Both holes being banged hard and fast left her all but breathless. Her words came in strangled gasps.

"Not..in..me..guys.......On..me..please.....I..want ..to ...feel...your..cum...on...me!"

That seemed to settle it. Both men knew they were close and May was cumming in an almost continuous orgasm as John pulled out of her pussy with an audible "squish" and quickly untied the ropes binding her wrists to the ceiling. May almost fell forward and Jack felt the exquisite sensation of his cock slipping out of her asshole. She landed in a heap on the floor where John stood over her and started to jerk his foreskin back and forward. His lips curled back into a semi snarl as he feverishly worked his cock.

"C'mon Jack. Let's give her what she wants!"

Jack was on the point of cumming anyway, and knelt down beside May's face as he began jerking himself off. A few swift strokes was all he could cope with and, with a shout of triumph, his balls succumbed and yielded their contents directly onto May's face and chest. Her husband followed suite quickly and spurts of semen from a different direction flew through the air and splashed down onto the oriental girl's hot skin. The two men came and came covering May with their sticky issue from her head to her belly. Her breasts and nipples were awash with the fluid and more pooled in her navel. The dark, neatly trimmed hair on her pubic mound was streaked and jism trickled between her open labia. Once the two men had recovered enough strength to maintain an erection, they treated May to yet another round, switching places many times with Jack, this time, emptying the contents of his balls between the sweet mounds of her tanned breasts.

By the time they had reached land, early the following morning, all three were exhausted. John and Jack had taken it in turns to nap between fucks, but May had refused sleep, claiming that she was willing and ready to take either or both of them at any time and in any hole. Jack had to agree, she was true to her word. They must have fucked her for six solid hours. Mainly, they took her when she was tied up - which was how she seemed to prefer it - occasionally releasing her hands or feet only so that she could pleasure them with fingers or toes. Jack thought it the perfect situation, and as they anchored close to the next unnamed island, he looked forward to many more sessions with his new friends.