Paid Vacation - Cover

Paid Vacation

Copyright© 2005 by Professor James

Chapter 3

Erotica Sex Story: Chapter 3 - 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  

When the alarm sounded at six, Alison required several seconds to recall exactly where she was. But as memory flooded back and she became aware of the bright tropical sun shining in her window she was intensely eager to get on with things. For a second as she recalled the events of the previous evening, everything seemed like a wild dream. Then the remembered the feel of Ken's hard body pressing against her and the excitement of him sliding into her brought back the wonderful reality. Still nude, she leaped from the bed and enthusiastically headed for the shower.

She remained nude while she packed her few belongings into her travel bag and put her brush and comb, her birth control pills, and a couple of other small things into a small belt pack. Finally she retrieved the bathing suit she had washed out the previous afternoon from where it hung drying in the bathroom. Somehow in this island vacationland it didn't seem unusual to leave the room before seven dressed only in a brief bikini. In fact, as she closed her room door, leaving the key inside, and started towards the beachfront coffee shop she saw several others out walking the beach or heading towards other buildings and none of them wore much more than she did. Although the sun was not yet high, the temperature was well into the seventies and Alison knew that in the islands it would soon climb into the low eighties, but not go far enough to be uncomfortable.

The sand felt warm beneath her feet as she crossed the fifty yards or so to where everyone had been the previous afternoon. As she arrived she saw that Sue and Kate were already there with Ken, Joe, and James. She joined them and within a couple of minutes all the others had arrived. The men had already ordered a light breakfast of fruits and breads which began to be served buffet style by the hotel's efficient staff. Before they had finished eating, several other small groups and a couple of individuals had arrived and were eating their own meals. A number of other people could be seen walking on the beach. This place seemed to come alive earlier than Alison had expected.

When everyone had finished James called over one of the hotel waiters. He spoke quietly to him for a second and Alison saw him press a bill into the man's hand as he smiled and nodded. She was then a little surprised to see the man begin to collect the travel bags from the five women and leave with them. "Don't worry," James said. "They'll be stored and ready for you when we get back. The reality was beginning to sink into Alison that she would be leaving for a two week trip with no clothing whatsoever except the few ounces she was currently wearing. The concept both excited and slightly frightened her.

James spoke again. "The boat is over at the hotel pier. It's only a few hundred yards so let's walk over." With that he led the group down the beach towards a long wooden pier running out into the bay. There were several craft, both power and sail, tied up along it, but James went on towards the farthest end. Even though Alison knew the boat was fairly large she was still impressed by the sight of it. The boat, anchored a little way out, looked to be a good sixty feet or more long with a fairly wide beam. Not built for racing, she thought, but it should be stable and certainly could offer enough room. A cockpit was located on a raised portion near the bow and a closed pilot house was above and behind that. This struck Alison as a little strange. She was not a sailor but had spent a little time with smaller craft on Lake Michigan and now thought that the layout of this craft made it necessary for the pilot to look over his shoulder to see the condition of the sail. But then, she thought, it did give a nice clear view forward and with a craft like this it was unlikely that they would be constantly sailing close to the wind. As she had already thought, this was not a racing craft.

There was a small, outboard powered launch with an attendant waiting at the end of the pier to take them out to the boat and everyone was soon aboard. James told them to stay topside. He then went to the cockpit, turned on the blowers, and shortly started the axillary engine. It appeared the boat could be run from either the closed pilot house or the open cockpit. Within five minutes they were slowly heading towards the mouth of the bay. As soon as they rounded the point a couple of the men began to handle the sails like they really knew what they were doing. In only a few minutes James cut the engine and the craft was slicing through the incredibly clear blue water at a fair pace.

For the next half hour everyone was either engaged in trimming the sails or just sat enjoying the sun, sea and breeze and each other's conversation. Then, as the island was dropping low behind them, James locked the sail and engaged what must have been some kind of autopilot. He came aft along with the other men who had been on the sails and joined everyone else in the aft well. A subtle change seemed to come over the men. James began in a tone that seemed more strongly in command, as though it were no longer a gathering of friends, but a situation in which he was clearly in charge. "I think it's time that our 'guests'" - he said the word so to indicate that they were anything but guests - "that our 'guests' learn their proper place." He opened a small storage compartment, brought out a nylon bag, and then turned to face the women. "All right, you wenches, strip."

Alison looked around. Kate, Kelly, and Sue immediately began to unfasten their bikini tops. After a second's hesitation, Alison followed suit and also saw that Barb was removing hers. Within thirty seconds the bottoms had followed and all five women were completely naked. Alison noticed that Kelly and Sue had, as had Kate, completely shaved pubes. James emptied the bag he was holding onto the well floor and Alison saw that it contained sets of padded cuffs. James collected their suits and placed them inside the now empty bag. He stowed the bag back into the compartment and closed a padlock onto the hasp. "You'll have no more need of these for the next two weeks," he said.

The other men now picked up sets of the cuffs and each went to one of the women and fastened the cuffs about their wrists and ankles. The cuffs were padded and soft so that they were not uncomfortable, but fit closely. Metal D rings were securely attached to each cuff. James spoke again. "Since you haven't been out in the sun too much, we're going to limit you so you won't get a burn. In a few minutes we'll take you below for some other 'activity', but first we have something that must be done." He nodded to the others and two men each moved towards Alison and Barb. They firmly took the girls' arms and led them over to a pair of benches, vinyl covered and heavily padded. Each girl was laid on her back and her hands were fastened over her head to the bench legs. Alison's own legs were spread to either side of the bench and tied, completely exposing her. She could see that Barb was similarly arrayed. The other three women then had their hands clipped together behind them, but were left free to watch.

One of the men went below and soon returned with a large plastic bowl. He removed a small, wet hand towel and squeezed out the extra water. As he placed this over Alison's crotch and she felt the hot water, she began to get a pretty good idea of what was coming. The man repeated the procedure with Barb. In a few minutes the man removed the towel from Alison's thick patch of red hair and her guess was confirmed when he began to apply shaving cream. She had noticed that Barb was a natural blonde - or had done a really good dye job - but now guessed that in a minute or two no one would be able to check either of their natural colors. As the razor tugged repeatedly across her sensitive skin, Alison felt the sea breeze began to caress in previously protected places and decided the sensation was a nice one. In just a few minutes both women were as bare in their private regions as they had been as little girls. Ken used the warm water to rinse them and then a towel to pat them dry.

He made an intense inspection, bringing a blush to both Alison and Barb. "Looks good to me," he said, "but maybe we should conduct a quality assurance test." At this the other four men laughed and moved over to the two girls. Ken knelt at Alison's feet and James did the same with Barb. Then suddenly Alison felt the unusual sensation of a wet tongue running up the inside of her leg and across the smooth area which, until a few minutes ago, had been shielded by her course, red thatch. After several seconds of licking, Ken stood and Bob took his place. For ten minutes the men switched off between the two bound women, licking their newly bared pubes and bringing both to a high level of excitement.

At last David stood up and said, "Well, I, for one, want to sample the wench." A murmur of agreement went through the other four men and Bob stood up from where he was busy with his tongue on Barb's bare crotch. Both men pulled off their bathing suits, revealing hard cocks. Alison was already in a high state of excitement and when a man she had met less than a day earlier and only spoken with a little, stood naked before her, lowering himself onto her bare body, she was too turned on to be embarrassed that her friend Kate as well as several others - practically strangers - were watching as she began to be soundly fucked. As David and Bob finished and pulled their shrinking members away, their places were taken by Ken and Joe. And when Ken finished with Barb enjoying her second orgasm, James took his place and drove her to two more.

As Alison lay in the sun, tied naked and exposed with the come of two men running out of her slit, it really began to sink in what this trip was going to be like. And she loved it!

The men remained naked and soon began to release the two bound women. "We don't want our returning captives to feel slighted," David said. "I think we should do something to celebrate the beginning of their new trip." He bent to another compartment and when he stood again, Alison could se that he held a cat of nine tails in his hand. The whip had leather tails about thirty inches long and looked well oiled. The tails blended into the leather wrapping of the sixteen inch handle. As he held up the whip the other men cheered and three of them went to the three girls. The women's hands were unclipped and then they were taken towards the front of the well. Alison had noticed that there were several tall poles rising from the edge of the well and that those along the front and back were connected by cross pieces located about eight feet up from the bottom. She had assumed that this arrangement was probably used to hold a tarp or such in case of weather. Now she saw it was for a different purpose as the three women were led beneath it. Their hands were raised above their heads, spread about two feet apart and then attached to light chains which were attached to rings in the cross piece. Their ankles were spread and the cuffs attached to rings in the deck. Each of the women was now stretched spread eagled with their backs towards the men in the well. Alison and Barb were led to the other end and arranged similarly, facing forward so they could watch Kate, Sue, and Kelly.

Ken and James had also brought out identical whips and now each of the three moved behind the bound women. David swung the whip sharply so the tails landed across Kate's ass. Her cry, more of surprise than pain, mingled with the sound of leather on flesh. It was immediately followed by the combined sounds of two more strokes landing on the other two pairs of bare buttocks.

When Alison had first seen the cat her feelings were mixed: apprehension and excitement. Now as she watched her friend and the other two being flogged she was still a little afraid. Would she be able to take this? Would she have to right away? But she was also surprised by the intense sensation the sight and sound caused. At the first stroke and Kate's cry she felt her own pussy flood with moisture. Now as the whipping continued with harder and harder strokes leaving red lines on the bare flesh and bringing sharp cries from the girls, she found herself squirming against her bonds and trying to squeeze her legs together. When she glanced around at Barb she saw the other woman appeared to be having a similar reaction.

The whipping continued with the men beginning to spread the blows. While they still concentrated on the now red asses, they also landed blows to the backs, legs, and even, Alison was somewhat surprised to see, to the women's fronts, including their bare breasts. Finally the blows ceased and David and James moved behind their two girls and began to fondle their tits from behind. It was obvious from the women's reactions they were enjoying everything, even including the whipping. Instead of playing with Kelly, Ken stepped back and turned to Joe, who was watching intently. In fact, Alison thought with a suppressed giggle, he'd better watch out or he'd get his tongue stepped on. Ken motioned to Joe. "Go ahead, Joe. This is your first trip so you might as well get into the way we run things from the start." Joe didn't need any extra urging and moved up behind Kate and began squeezing her firm breasts as he pressed himself against her hot, red rear.

Ken moved over to Alison and Bob stepped next to Barb. The two men, while continuing to watch the action in front of them, began to tease the two bound women. He rolled Alison's hard nipples between his fingers and thumbs, he let his hands brush over her swollen pussy lips and newly exposed pubes. Finally he used a finger to penetrate her and play with her hard clit. Meanwhile the three men had all entered the hanging women from behind and were holding onto their hips and fucking them in hard, deep strokes. Alison was aware that there seemed to be a woman climaxing constantly, but was so involved with her own arousal that she couldn't have said which ones. Actually before the men stopped each of the five had come at least two times. Kate had had four hard climaxes and was now hanging almost limply.

Finally as the men began to settle Ken said, "You guys had better get these girls below before they get sunburned. I'll take the first watch, but I think I'll keep Alison up here for decoration if you don't mind. I'll run things from the pilot house to keep her out of the sun."

The others agreed and began to release the women from the chains and lead them below. Ken unfastened Alison's wrists and ankles and, taking her wrist in his hand, gently pulled her forward and up the ladder into the pilot house. Here he once more bound her in a standing spread eagle from ceiling and deck rings just to the left of the pilot's chair. He checked the instruments, checked their position on a chart and made a quick survey of the bridge, but left the auto pilot engaged.

At last he moved to stand facing her. He let his hands roam across her firm breasts and then slide down and around to her ass... "Well, is it what you expected so far?" he asked.

Alison's breathing was starting to become faster again as she became aroused, but she managed to say, "I didn't really know what to expect. I still don't. But I'll say I've never been so turned on. I had no idea watching those three get whipped would make me so hot."

Ken laughed. "Just wait until it's you on the receiving end." Alison shuddered but it was with a shiver of excitement. "In fact," Ken went on, "I don't see any real reason to wait." With this he pinched her nipples and then went to one of the compartments behind Alison. When he came back he was holding another leather cat. Alison stared at it like the proverbial small animal mesmerized by a snake. Ken let the tails trail over her bare skin, across her ass, and up across her tits. Alison sucked in her breath as the leather pulled across her hard nipples. Ken continued to drag the whip across her skin and play with her for several minutes.

Suddenly Alison heard a sharp feminine cry from below. This was soon followed by several others, but Alison didn't worry about the other girls. Instead her reaction was to become even more aroused. Finally Ken stepped back and raised the whip. He brought his hand sharply down and Alison sucked in a sharp, deep breath as the leather tails snapped against her taut rear. The blow didn't really hurt, just stung a little. "You remember your safe words OK?" Ken asked. Alison nodded and he landed another blow, slightly harder than the first.

For the next twenty minutes Ken continued a slow flogging. The strokes became progressively harder and he spread them around. The first time the lashes landed on Alison's nipples she let out a loud cry. But she didn't even think of using a safe word. She was becoming more turned on than ever before and was constantly surprised that this stimulation, now definitely becoming painful, had such an effect. Ken brought the tails up between her legs from behind and the lashes landed on her swollen pussy lips, bisecting them, with one striking directly on her clit. She screamed and started to come. As she shook through her orgasm, straining against her bonds, Ken continued to whip her. He eased a little as she came down but continued the assault, soon increasing the strength of the beating once again. And Alison responded and began once more to be aroused. The blows were hard enough that they were leaving red lines and generally bringing cries or screams, but they also drove her higher and higher. Finally Ken gave her several especially hard strokes and then dropped the whip and moved to face her. His long, hard cock touched her pussy lips and then plunged in all the way in a single stroke. Alison was so wet that he met almost no resistance entering, but then as he began to withdraw her muscles clamped down hard trying to hold him inside. He fucked her in deep, hard strokes, his hands running over her hot, sore skin, squeezing her ass and pinching and pulling her nipples. When he came and Alison felt his hot come spurt deeply inside her, she screamed and came again herself.

As he shrank and slipped out of her, Alison felt her juices and his begin to run down the inside of her legs. Tied spread open like that there was nothing she could do about it and she was again surprised that the sensation of this, instead of feeling dirty and icky, turned her on even more. She was definitely discovering a lot of surprising things about her own feelings and reactions.

Ken withdrew and left her hanging there. He moved around her and let his fingers tease her ultra sensitive areas, pinching her swollen nipples and squeezing her clit. He let his fingers trail across her pussy from behind, the juices running over his fingers. He then moved a finger up the crack of her ass and began to gently push against her anus. Alison first clamped down but then realized that she loved this sensation, too. She tried to relax and soon Ken's wet and slick finger began to penetrate her rectum. She had never imagined this could feel so good. He began to work his finger in and out and Alison responded. Ken added his thumb to the play, letting it rub her hard clit. In just a couple of minutes Alison found herself once more climaxing as Ken's thumb and finger pressed into her aroused body.

As she calmed down and Ken pulled his hand away, he said, "You are definitely one hot woman, aren't you? Was this really your first whipping?"

Alison nodded. "I've played spanking games a few times and had a belt used on me, but I've never been whipped before. And before you ask, I loved it! I don't think I would have if it had been a real, severe whipping instead of a play one, but you turned me on like never before in my life."

"Well, you actually came from the whipping alone, so you must have enjoyed it. I expect you are going to enjoy this whole cruise quite a bit."

Alison grinned at him. "I'm sure I will. Now, how about letting me down."

"Nope," Ken said. "I like you where you are. You make a nice decoration. I think I'll just leave you there until someone comes to relieve me at the watch. Besides, I may want to torture that beautiful body of yours some more."

Alison seemed a little surprised and actually turned a little red - or maybe a little more red - at the idea that she would stay here, spread wide and open. This was going to turn out to be a really interesting vacation. Ken checked the instruments again and then came back beside her. He stood next to her looking out at the ocean and casually sliding his hand across her tender ass. Alison could hear the occasional cry or scream from below, but also some sounds that more likely were orgasms. Finally she asked, "Ken, is this boat set up for this kind of play? There seem to be tie points everywhere up here. I haven't seen below decks yet, but I'll bet there are a lot of rings and stuff there too."

Ken laughed. "You're pretty observant. Yes, the boat belongs to a guy we know who has more money than all of us put together. He bought the boat and then completely redid the interior to turn it into a floating BDSM playroom. He and his wife love this kind of stuff and often bring someone else with them on trips for the same sort of games. He lets us use the boat once in a while and, yes, some of us have been guests on cruises with him and his wife. She's pretty hot, too, I'll say, but not even she reacts like you did awhile ago. You'll find a lot more than tie rings below decks. And, by the way, all of us have been on the receiving end of the cat, too. So we do know what it feels like. In general, we like that end of things too, but not as well as having you girls as our captives. So don't expect to get to whip my ass on this cruise." The he looked at her slyly. "Maybe some other time."

Ken continued to tease and play with Alison, keeping her aroused but just below the level of coming. They discussed the boat and sex games in general, but Ken wouldn't tell her exactly what she could expect. "It's usually better as a surprise," he said. At one point he got a couple of clothes pins and put them on her hard nipples. He left them there for fifteen minutes, sometimes tugging or twisting them while continuing to stimulate her with his hands and tongue.

After what must have been a little more than an hour, David appeared with Sue. "OK, I'll take the watch," he said. Why don't you go below and enjoy our captives a little." Then he noticed the red lines still showing on Alison and added, "But I see you have already begun. Well, take her below anyway. I'm sure the others would like to share her." However, his smile took any real callousness from his remark.

Ken released Alison and David moved Sue over and began to fasten her where Alison had been. Sue had small clamps on both of her nipples connected by a light chain and Alison noticed that there were a number of red lines on her body. And when she passed in front, she saw that Sue appeared to have some object embedded in her rear. But the look on Sue's face showed she was enjoying this as much as anyone else.

Ken led Alison down the ladder and then down another to end below deck. There a long, narrow hall - companion way, Alison remembered - led from the base of the ladder on forward and also towards the stern. Alison could see that these ended in larger rooms at the bow and stern and a number of doors opened off the sides. "There are six cabins, including the owner's," Ken explained. "Plus three heads, a galley, and several 'special' compartments. There are also the two large lounges, fore and aft. You'll see them all before too long, but I think the others are aft right now, so let's join them."

Alison's hands had been fastened together in front of her and now Ken pulled them along behind him so she had no choice but to follow him to the rear. She noticed that the companionway was very narrow and that if someone came the other way they would have to turn sideways to pass. Since it looked like the men would be naked most of the time as well as the five women, this, all by itself, might make for some interesting moments during the next two weeks.

Ken led her into a large room at the end of the passage. This was the full width of the boat and had high windows along both sides and across the stern. Leather covered furniture, including several couches, was arranged around the walls, but there were also some not quite so common objects. But what first caught her eye was the sight of Barb and Kate, both hanging from the same point by their wrists and pressed tightly together, front to front. Bob and Joe were each holding a long, leather covered paddle which they were applying at irregular intervals to the already red asses of the two women. On closer inspection Alison saw something else. She couldn't tell exactly what it was, but there seemed to be some object between their legs with an end buried in each of their pussies. Later she was to find that this was a double ended dildo. The two girls were reacting to the paddling with sharp cries but also by grinding their crotches together as much as they could in this position. Off to one side Alison saw Kelly. She was bound, bent over something that looked like a padded leather vaulting horse. She was positioned at one end with her legs spread and ankles bound to the horse legs. She lay along the length of the padded leather with her wrists pulled tightly down to the other set of legs. There was a weighted clamp attached to the nipple Alison could see (and she assumed, correctly, another one on the other side). Her ass was covered with cris-crossing red lines, but what really held Alison's attention was that James had his cock buried deeply, not in her vagina, but in her rear hole and was fucking her in long, slow, deep strokes. Kelly was clearly getting off on this and even cried for him to fuck her harder, just as James stiffened and grabbed her hips, obviously shooting his load deep within the girl's bowels. This seemed to set Kelly off and she began her own climax.

As James started to come down he looked around and saw Ken and Alison. "I see you brought our new member down," he commented. Then looking critically at Alison he added, "And I see you have already given her a sample of the cat. How does she like it."

"You wouldn't believe," Ken replied. "If I didn't know better I'd say she's been doing this stuff for years. She's definitely hot. Just wait until you try her."

The thought suddenly struck Alison that she had not met any of these people except Kate until just about twenty-fours ago and here she was watching one of them get fucked in the ass, another two getting their butts beaten bright red, and Ken was talking about using her for a sex toy as though she wasn't even there. But the thing that surprised her about this thought was that none of it seemed really strange at all. "I guess I've just fallen down the rabbit hole," she thought. "And I really seem to be taking to this Wonderland completely."

James pulled away from Kelly, leaving her bound to the horse, his come dripping from her ass. Ken looked at Kelly's taut bottom and casually said, "I'm really looking forward to fucking Alison's ass, but she says she's never done that before. So I suppose we should wait until tonight and prepare her a little first."

James ran a critical eye over Alison's bare rear. "She does look like her bottom would feel awfully good," he commented. "But you're right. Why don't we start getting her ready for that and then I'll play with her for a little while and you can have Kelly's ass now, if you want. You remember how nice and tight she is there."

"I sure do," Ken replied. "That sounds great. Come on. Help me get Alison ready first. Or would you like to do it?"

"I wouldn't mind that at all," James replied. "Just help me get her in position first." He took Alison's wrists and led her over to a padded leather table and had her stand with her back to one end. He and Ken helped her to sit on the end of the table and then to lie down on her back. Her hands were separated and pulled above her head where they were fastened to the two sides of the table end. The two men then pulled her down the table until her bottom came almost all the way off the padded surface. Two chains were attached to her ankle cuffs and Ken and James each pulled an ankle up and out where they fastened them to ceiling chains. Alison was left stretched on the table, her legs spread four feet apart and pulled tightly towards the ceiling. A wide belt was added to hold her waist down to the table.

"OK, that's got her," Ken said. "I'm going to sample Kelly so go ahead and enjoy Alison." He then walked over to the other bound woman and slapped her hard on her tight bottom. "Hi, Lover," he said. "Ready to get your ass reamed again?"

Kelly twisted around to look at him over her shoulder and smiled. "If you think you can get that thing hard enough to do it, I'm ready to wring you dry, Stud."

Ken laughed. "That kind of talk calls for some punishment, I'm sure. Let's see what I can find here." He turned towards a cabinet against the wall and dug around inside for a few seconds. "Just the thing," he said and returned to Kelly. She couldn't see what he had in his hands and the first thing he did was to remove the two nipple clamps. Kelly cried out at the pain from the returning blood, but Ken made it worse by rubbing and squeezing her crushed nipples. Then he brought around the object he had retrieved from the cabinet. It was a small cat with light weight tails about fourteen inches in length. He swung it experimentally a couple of times and then brought it up from her right side to land across her dangling breast. Kelly screamed at the sting of a leather tail snapping against her hard and sore nipple. Ken repeated the blow, bringing another loud response. He switched to her left side and began to abuse that taut globe also. Before he put down the whip he had delivered a dozen strokes to each of Kelly's breasts and fine red lines largely covered their surfaces.

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