Paid Vacation
Copyright© 2005 by Professor James
Chapter 4
Erotica Sex Story: Chapter 4 - Two roommates, grad students, join three other young women and five men on a sail boat for a most unusual vacation - two weeks as BDSM playmates. Three of the girls have been on a similar trip, but Allison and one other girl find out just what they have gotten themselves into - and find they love it.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual BDSM MaleDom Spanking Group Sex Oral Sex Anal Sex
The five women once more prepared a meal, this time a hearty stew and warm French bread. When everything was ready, the men, still wearing bathing suits, came into the forward dining area and sat down while the girls waited along one side.
Once they were seated, Alison had expected them to call the girls to sit between them as they had at lunch. But James suddenly stood up again. "This year," he began, "we're going to start a little different tradition. We will expect you women to dress for dinner each night."
All of the girls looked at each other. The three returning women, especially, looked confused. They all knew that the only clothing they had on the boat were the bikinis and these were locked away. James came over to them and they noticed he had a small box in one hand. "What we have in mind for you to wear are these," he said. Bob stood and came over to join him. They reached into the box and each removed a sterling silver chain with a silver oval pendant hanging from the middle. It looked like a necklace until Alison noticed that instead of a standard necklace clasp, each end of the chain was a small, plastic covered clamp.
James took the chain he had over to Kate, who was standing next to Alison. Alison could now see that the oval had Kate's name engraved on it and, when it turned, she saw the other side bore an engraving of two crossed cats of nine tails. Bob carried his over to Sue. All of the women were looking down at the chains as James and Bob showed them how they were to be worn. James leaned forwards and brought his mouth to Kate's left nipple. He licked at it twice and then sucked hard on the small brown nub. Kate sucked in her breath and Alison saw her other nipple harden even as James removed his mouth to reveal a left nipple, hard and standing out from her breast. He repeated his actions with her right tit. Then he applied one of the silver clamps to each, leaving the sterling oval hanging slightly below and between the two taut globes.
Bob had done pretty much the same with Sue and now the two men repeated their actions with the other three girls. When all were adorned James said, "We expect you to wear these each night for dinner. They should be on when we come down and remain there until we have finished the meal. The two men then returned to their seats and indicated that the women were now to join them.
Throughout the meal Alison was continually conscious of the clamps on her tits. But she also noticed that the silver chains and ovals were a beautiful addition to the female bodies. Their pressure kept the nipples hard and sticking out and the contrast with the smooth skin looked extremely sexy. "Maybe we should keep on wearing these when we get home and start a new fashion," Alison thought.
When the meal was over, the women were told to leave the chains in place and to clean things up. The men remained at the table and one of them brought out a deck a cards. As the girls returned things to the galley and washed the dishes, they heard the sound of a poker game in progress. When they had finished and returned to the dining longue, James called a halt. He began, "As three of you know we usually each have one of you for the night. We're still planning on doing that. This time, however, we thought it might be interesting, that instead of just drawing numbers to match people up for the first night, if we tried something different. So we will. Barb, why don't you come over here?"
Barb moved over beside him. James put cuffs back around her wrists and then attached them to two ceiling chains, raising her onto her toes and spreading her arms about three feet apart. He lifted the oval and gave a couple of light tugs on the chain. First looking down at the oval and then turning back to the table he said, "the prize for the first round tonight is, Barb. Five card draw, nothing wild."
He returned to his place at the table and sat down. David began to deal cards. They played with two rounds in which to draw cards and when the final showdown came, David had a straight and rose to claim his prize. He first unchained her hands only to refasten them behind her back and then, while Barb stood by, brought over Alison, fastened on her cuffs, and bound her up on her toes as Barb had been. Then he removed the clips from Barb's nipples, bringing gasps and a couple of moans, and led her over to the side to watch.
When Alison had time to consider things later she decided that the card game was an inspiration. While she knew that all the girls would be shared by all the men, and while she, and she was sure everyone else, was attracted to each of the guys, there was still bound to be some with more attraction than the rest for each. She had found that she loved sex with each of the five, but Ken seemed to excite her a little extra. And she thought he might feel the same way. If companions had been selected at random, there would be only one chance in five that a guy would end up with a particular girl. And while no one would really mind, a guy might prefer to have the first night with a particular woman. However, if they simply stated their preference it was always possible that a conflict might arise. Worse, someone might feel slighted. But with the card game, if a man wasn't after the particular girl offered during any one round, he could easily throw away any good cards and be pretty sure of losing that round. On the other hand, if he did want that particular girl, he could play his best and if two guys wanted the same woman, well, chance would probably decide it. In any case no one ever had to know if someone was trying to win or not.
As the cards were dealt, Alison watched every move. She hung from her chains and was intensely aware of the silver clamps attached to her nipples and the heavy sterling oval hanging below her breasts. The whole idea of these guys playing cards for her was an incredible turn on. She felt like a slave on the block and her pussy began to flood. She watched as the first five cards were dealt to the four remaining players. From where she was hanging she could just see a little over Ken's and James' shoulders. She could tell that James held four red cards and one black and she thought all the red ones might be hearts. Ken had a three of clubs, but she couldn't tell what else.
After the deal, the players each asked for cards. James called for two and discarded his black card and one of the red ones. Maybe it was a diamond after all. Alison saw that he drew another heart and another card she couldn't see. Ken asked for three cards. Alison was somewhat disappointed because she thought this probably meant he didn't have much of a hand. She had been hoping a little that she would be his for the night. She could only see one of the cards he got in this round and it was a three of diamonds. At least he had a pair. The other two players each took two cards and Alison had no idea what they held.
Alison was feeling the strain in her arms as the third round started. James took one card and it looked like it made a flush to Alison. Now she expected to be his for the evening. Then Ken called for two cards and she couldn't she what he got at all. Bob asked for one and Joe wanted two. Now she waited to see what everyone had, but she expected there was little chance of anyone beating a flush. Joe laid his cards down face up with only a pair of Jacks. Bob had a pair of twos and a pair of fives. James slapped down his flush with a wide grin and turned expectantly towards Ken. Ken placed three cards down, an eight of clubs, the three of diamonds and the three of spades. "I drew these, so I had a pair," he said, and James leaned back smiling. Then Ken went on, "And I have this other pair I was dealt." He laid down his last two cards and Alison, as well as everyone else, saw they were the three of clubs and the three of hearts. Four of a kind! Alison felt a sudden surge of heat between her legs and realized she felt pretty good that Ken had won her.
James had looked a little surprised when Ken had won, but didn't seem to be really disappointed. "After all," Alison thought, "none of us are bad and he'll have plenty of time with each of us in the next two weeks." Ken released her, bound her hands behind her back and then stretched Sue in her place.
The results of the rest of the rounds were that Joe won Sue, Bob won Kelly, and James ended up with Kate. The men placed the silver chains in a cloth-lined drawer in the room and made sure each girl knew where they were. Then they spent the next half hour teasing and playing with their bound captives, driving them to an incredible level of arousal, but not allowing them the relief of orgasm. Finally, as the men released the girls, Ken whispered to Alison, "That's just to make you ready for tonight. I intend to get full value from you, so you can count on being well worn by morning." His words made Alison even wetter and she squeezed her legs tightly together in response.
When they were free, James announced that they would have a couple of hours of free time. Every one headed topside to enjoy the warm evening. Running lights were on and a light breeze kept them moving at a slow but steady pace. The girls returned to the after deck where they had lain in the sun earlier. Alison had noticed that the area seemed to be covered with a large vinyl pad so it was comfortable to lie on. Probably comfortable for other activities, she thought. As they settled down to look up at the emerging stars, the men gathered in the well just forward of them. The deck where the women were lying was illuminated with a soft glow from the boat's lights and the men sat where they could watch the naked girls. "These guys sure have one track minds," Alison thought. Then she realized she herself had thought of nothing else but sex since getting on board. "Great track to be on," she murmured to herself just loud enough that Kate overheard.
"What was that?" she asked.
"Nothing," Alison quickly said. Then she added, "Do you still want to put on a show for the guys?"
"I'm definitely ready if you are," she replied. With this she leaned on her elbow beside Alison, who was lying on her back, and began to let her hand slide across Alison's breasts.
Alison was shocked by how Kate's touch sent an almost electric charge through her system. This felt hot! She sucked in her breath and reached up with her own hand to slide over Kate's taut globes and back and forth across her hard nipples. This felt as good as Kate's own actions and Alison forgot any apprehension she had had about girl-girl play. By the time Kate lowered her mouth towards Alison's already hard nipples, all five of the men were watching the pair intently. When Kate lifted her head from Alison's breasts, Alison pulled her down on top of her sweating body, feeling their tits slide over each other and using her hands to pull Kate's mouth to hers for her first ever girl-girl French kiss. The two continued to kiss, lick, and fondle for some time, even fingering each other. Finally they ended in a sixty-nine, each with her mouth clamped tightly to the other woman's pussy. When they finally came in noisy climaxes, the men applauded and they lay back to recover. In a couple of minutes the sounds of more play came to them and Alison looked over to see Sue and Barb beginning to engage in their own games. Kelly moved over beside the two women and used her own hands and tongue on both Sue and Barb. Once again when they came they were answered by applause from the watching men.
At last all the women settled down and Alison was surprised when she suddenly woke, realizing that the warm air and the rocking of the boat had actually put her to sleep. She looked around at Kate who was starting to sit up. "Welcome back," Kate teased. "It's almost nine, so why don't we go grab a quick shower and then I think the guys have a little something planned before the night watches start."
The two headed below and Alison saw that the other three girls had already disappeared. She and Kate quickly showered and then headed back to the aft longue where they could hear some music. As they entered the large area they saw that the lighting was just strong enough to see their way around and was provided by several flickering candles in red glass holders spaced around the walls. All five men were there along with the other three women. Kelly, Barb and Sue each had their cuffs back on and their wrists clipped together behind them. Their "owners" for the night, now also naked, were each slow dancing with them, holding them close with a lot of rubbing and feeling going on. As they stepped into the room, Ken and James moved beside them and soon Kate and Alison had their own hands bound behind them and had joined the others in what Alison had decided was some of the sexiest foreplay she had ever imagined.
By the time the first watch approached, Alison felt wet to her knees from her own juices and the feel of Ken's hard cock against her while they danced had taken her to a level of arousal she had never thought possible. As Joe, along with a bound and squirming Sue, headed topside for the first watch, the other four couples each moved towards their own cabins.
Ken led a very aroused Alison into the forward cabin on the port side. As he closed the door behind them, Alison looked around the small room. Besides the two oversized bunks there were a couple of chairs and two sets of small lockers and one larger storage area like a closet. Otherwise there was only a small area of floor space between the door and the beds.
Ken turned towards Alison and pulled her against him for a long, deep French kiss which left both of them short of breath. "I think it's time to make use of that wonderful body of yours," he said as he led Alison over to the lower bunk.
Ken pulled down the one light blanket, leaving the bed covered with a smooth, finely woven cotton sheet. He helped Alison to climb onto the bed and kneel facing the head. He then unfastened her cuffs and told her to lie down. She started to roll onto her back and he stopped her. "No. Face down." Alison complied and realized that he was probably going to breech her virgin rear opening. Both looking forward to this experience and still somewhat scared, Alison stretched her arms above her head in response to Ken's tugs and soon found them anchored to the corners at the head of the bunk. Ken confirmed her guess when he placed a pillow under her hips, raising her ass into the air. Finally he spread her legs and tied her ankles to the other two corners.
Alison was now stretched tightly, her ass and soaking pussy elevated. She was very aware of the butt plug which was still in place. Ken began to slide his hands all over her body, up the insides of her legs, around her breasts, between her legs. Several times he gave sharp taps to the base of the anal plug, causing a surge of lust to burn through her. Then he stood and got something from one of the lockers. Alison looked over her shoulder and saw that he had a tawse, a three inch wide strap of heavy leather attached to the end of a twelve inch handle. The strap was slightly over a foot long and the end split into three separate tails. He raised his arm and brought the strap down in a hard slashing blow across her unprotected bare bottom. Alison let loose a loud scream. It had felt like a red hot piece of iron had struck her ass. Before she could completely get her breath back, Ken struck again at a slightly different angle. Again her response was a loud cry. Three more times the strap rose and fell, each time bringing forth a cry from the bound girl.
Finally Ken stopped and began to rub his hand lightly over the hot and red abused area. He let his other hand tweak her nipples and dragged his fingernails along other sensitive areas of flesh. He took hold of the anal plug and began to twist it back and forth and finally to ease it out. Alison's muscles had been clamped around the narrow neck of the device for several hours and when Ken began to pull, they tried to keep the plug inside. But he pulled with a steady and increasing pressure until the wide area of the plug began to stretch her tight ring and, with a sharp, burning pain the plug popped free, leaving behind a strange empty feeling. But Ken did not leave her empty for long. Almost immediately a Vaseline covered finger penetrated her rear and began to twist and pull in and out, spreading the lube around her rear entrance. This action began to make Alison even hotter, a feat she would have thought impossible thirty seconds earlier.
Ken continued for a full minute and then removed his finger. Before Alison could look around the tawse once again struck her bare ass. She screamed once more, but somehow the intense pain of the strapping was driving her even higher. Ken delivered another five blows, each feeling like a searing brand across her tender flesh. Then once more he stopped. This time Alison felt a large dildo pushing into her pussy. As the length of the plastic intruder slid up her wet tunnel, Alison nearly came. But she was distracted by Ken's finger once more beginning to explore her rear hole. Again he rubbed lube into her for half a minute and then again withdrew only to bring back the tawse for another five searing blows, each eliciting a scream from the bound girl.
Then Ken put down the strap and climbed onto the bed between Alison's stretched legs. Within seconds she felt the head of his lubed cock begin to press against her stretched ring. By now Alison had practically forgotten any fear or apprehension she had about anal sex. She was so hot she just wanted him to plunge all the way inside her and she didn't care exactly how he did it. However, Ken was able to control himself and stopped with only the head of his cock inside her. Suddenly, as Ken reached a switch, Alison felt the big plastic cock in her pussy begin to vibrate. At the same time Ken began to push against the tight muscles of her ass. Pulled taut as she was there was nothing she could do to oppose or aid the action, but her excitement made her intensely aware of a million sensations. Although the sheet was of the smoothest and highest quality cotton available, Alison was sure she could feel each individual thread as they slid over her swollen and hard nipples. It seemed that each of Ken's course hairs left its own impression on her sore and double sensitive rear. But mostly she was aware of the million sensations as Ken's wide cock split her anus. It felt as if she were being split in two, but it also felt hotter than any sex she had ever experienced. When Ken's seven inches was finally as deep as it could go, he held steady for what seemed forever to Alison but what was really only about a minute. Then he slowly began to pull out. Alison's internal muscles clamped down to hold him inside but at the same time she was driven to plead, "Fuck me. Fuck me hard... and deep... hard and fast. Fuck my ass, Ken, as hard as you can."
Ken pushed in and out, increasing the speed of his penetration. He did not, however, "fuck her as hard and deep as he could". Not yet. This would have caused her real pain and Ken was experienced enough to know that it would be better to gradually increase the action. But he didn't take very long and within less than a minute he was sending his entire length as deeply as it would go into Alisons tight rear. Alison had started to come the instant Ken's shaft sank to it's full depth the first time. Then she came again. And again. As she started into her fourth orgasm, Ken could hold back no longer and pushed especially hard, beginning his own climax. Alison felt several waves of hot come being released deeply inside her bowels as she strained against her bonds. Ken collapsed on top of her, his shaft still buried deeply inside her bottom.
After a few seconds Ken started to pull himself off of Alison, but she stopped him. "No, please Ken. I want to feel you inside me and feel your weight on top. Just lie there far a few minutes, please." Ken relaxed and let his weight crush her once more. His hands began to roam, touching all her sensitive spots. Finally, as his cock softened, he rolled off of the young woman. He leaned forward and loosened the bonds stretching her, but left her still anchored in a spread eagle form on the bed. He gently removed the pillow from beneath her hips and casually began to stroke her hot and sweating form.
Alison yawned and, somewhat embarrassed, said, "I'm sorry. I feel absolutely like jello. I've never come like that before and it seems to have really drained me. Ken, that was wonderful! It was like all the orgasms I've ever had, rolled into one."
Ken smiled and let his hand slide across her shoulders and back and on down over her hot and red ass. "You did seem to like it. But, you're right. We'd better get some sleep. Remember I've got the two till four watch. And you'll be going with me." With that, he set a small alarm and turned off the small room light.
Alison awoke to the sound of the alarm just as Ken reached over and turned it off. Surprisingly, even though she had only slept two and a half hours or so, she felt rested and she was startled to notice, once again aroused and horny. This trip was turning out to be a lot more than she had expected, and she had expected quite a bit. She felt Ken's fingers lightly stroke her flanks and thighs, the sides of her breasts, and the round, sore globes of her ass. As his hand slid across her bottom, she still felt the hot lines raised by the strap, but the pain was largely gone, leaving only a pleasant soreness most places. His fingers continued to investigate her secret crevices and she responded by trying to squeeze her legs together and breathing faster. She was still held fast by her bonds and this frustration added to her arousal.
Finally Ken released her ankles from their cuffs and then her wrists. As she rolled over he pulled her hard against his body for a passionate French kiss. When they broke apart Alison was ready to continue, but Ken said, "Come on. We'd better grab a quick shower in the head and get topside for the watch."
A frustrated Alison followed Ken the short distance down the companionway to the head and went inside. Ken immediately went over to the toilet and relieved himself. This reminded Alison that she, too, desperately needed relief, and when Ken finished she lowered the seat and sat down. Sitting, she became aware that her muscles - especially those around her anus - had been stretched and mistreated, but again it was only a pleasant ache. After she had wiped herself and joined Ken in the shower stall it suddenly came to her that she had just shared a bathroom with a man. Alison was certainly no prude, but never before in her life had she used a toilet with a man in the same room and certainly never with both of them completely naked. But what really surprised her was that she felt no embarrassment at all: everything had just seemed natural.
She and Ken quickly showered and dried off. They headed back down the companionway where they stopped at their cabin long enough for Ken to get his bathing suit and to put the cuffs back on Alison's wrists and ankles. Then they headed topside where Bob and Kelly were waiting patiently. Well, Bob was waiting patiently. Kelly had no choice as she was tied in a tight standing spread eagle to two poles near the back of the cockpit. There was a set of chained clamps attached to her nipples and Alison could see some darker marks - which were probably a deep red - on her taut ass. Alison could also see a number of other marks which were probably the result of a flogging as well and it looked like vibrators buried deeply inside both her pussy and ass.
"How was the watch?" Ken asked as he and Alison climbed down into the cockpit.
"Calm," Bob said, "except that this wench needed a little discipline. Now, I think, I can take her below and finish up what she has coming." As he said this he tugged on the chain between Kelly's nipples, bringing a sharp intake of breath and additional squirms from the hot and bound woman. "Go ahead," Ken laughed. "I'm sure Alison is ready for some night air to cool her hot ass. It's already gotten a little workout tonight."
Bob laughed and began releasing Kelly from her bonds. He left the vibrators and clamps in place and fastened her hands together in front. With a slap on her ass to start her along, they headed towards the ladder. It seemed to Alison that Kelly was wiggling her tail a little more than was natural in open invitation to the man following close behind her.
Ken led Alison over to the poles where Kelly had just been and soon she found herself stretched much as the other girl was when they had first come up. But Ken made no move to add clamps or vibrators. He just pulled her bindings tight so that she had almost no freedom of movement and then went to check the instruments. "Actually," he commented over his shoulder to her, "the watch pretty well keeps itself. The autopilot handles the boat and the radar will sound an alarm if anything shows up within a mile. So that leaves me pretty well free to do whatever I want with you."
The night air was slightly cool and Alison felt a few goose bumps breakout on her exposed body. She also found the breeze rather stimulating, but then everything seemed to be stimulating today. Ever since they had sailed this morning - yesterday morning, she corrected herself - the entire boat reeked with the sights, sounds, and smells of sex. And she couldn't believe how much she loved it. A day ago she barely knew these people. Now she had spent the last eighteen hours or so completely naked and had had sex with most of them. It had been a day of unbelievable firsts. Besides her first time at being naked for this long and her first time not being alone when she used the toilet, she had had her first real whipping. She had had her first sexual experiences with a woman, both as an observer and as a participant. And she had had anal sex for the first time. And, she realized, she had loved all of it.
As she was thinking about these things, the breeze had been gusting a little, the cool air teasing her bare breasts and pussy. Despite her recent shower, she could feel her juices leaking down her leg. Her nipples hardened in the cool night breeze and became incredibly sensitive. For that matter she could feel her hardened clit sticking out as the teasing breeze helped bring her to a strong level of arousal. Then she saw that Ken was getting something from a locker and making his way back to where she was tied. As she looked down she saw that what he had clutched in his hand was a dozen or so satin ribbons. She stared as he tied these to a pole. Then he moved the pole into a bracket and adjusted it so that the breeze made the ribbon ends constantly tickle and tease her sensitive areas, including her pussy lips, her clit, and both hard nipples. Then he sat down to watch as her breathing increased and she began to struggle against her bonds to find some relief from the constant stimulation.
For the next half hour Alison strained to handle the simple, yet devastating, torture. She felt that she could hardly stand the stimulation, yet there was nothing she could do about it. Well, almost nothing. Before the half hour was over, she had come three more times.
Throughout all of this, Ken had watched her struggle and enjoyed the sight of her restrained body. After her third climax. Alison hung exhausted in her bonds, too tired to do more than twist and squirm slightly in a hopeless attempt to avoid the relentless stimulation of the blowing ribbons on her overly sensitive body. Ken saw that she was nearing the end of her endurance of this particular teasing and, at last, stood and removed the ribbons. "Seems you liked that. Maybe when you're a little more used to it I'll keep it up for the full watch."
Alison cringed at the thought of two full hours of that delightful, yet terrible, stimulation. Ken went on. "But for now I think maybe a different form of stimulation is in order." With this he picked up a cat with eighteen inch soft suede lashes, each about three quarters of an inch wide. He held the instrument by the foot long wooden handle as Alison stared at it intently. He moved behind her and brought the whip down, lightly stroking her ass. The blow wasn't really hard and the soft leather felt more like a teasing caress than punishment. He repeated the blows, landing one light stroke after another on her ass, her tits, her pussy, the inside of her thighs. He brought the whip up under handed and let the tails slap against her open pussy lips. As he continued, the blows increased in strength until soon Alison was feeling a painful sting with each. Still, they aroused more than punished. Each time the leather fell across her sensitive clit, Alison sharply sucked in her breath and strained against her bonds. The blows continued to increase in strength and soon were bringing repeated cries from the bound woman. But she also found herself on the edge of coming again. Finally a particularly hard swing directly onto her clit brought a scream and Alison began to contort uncontrollably in the beginning of another orgasm. Ken instantly reversed the whip and began to push the smoothly polished wooden handle into her dripping pussy. Alison cried out again and squeezed hard with her internal muscles, clamping the wooden shaft tightly inside her hot tunnel.
Ken stepped back and watched her diminishing contractions until once again she hung limply. Then he stepped forward and bent to suck hard on each of her nipples. Alison shuddered and gave out with a loud groan at the stimulation. "I don't think I can take any more," she cried.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.