Paid Vacation Pt. 01

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.

"Now, Wench, maybe that will teach you not to smart off at me." He moved behind her and wet his finger. He began to tease her stretched anus and soon was pushing the digit deeply inside and twisting it back and forth. Kelly was loving this treatment and wiggled her ass as much as her bonds allowed to get deeper penetration. Finally Ken withdrew his finger and replaced it with the head of his large, hard cock.. Slowly he pressed towards her, driving his stiff shaft into her already stretched rear passage. He pressed his entire length into her and then held it there. The look on Kelly's face was indescribable, but definitely a happy one. Then Ken began to slowly move out and back in again and within a few strokes, Kelly was encouraging him to fuck harder and faster.

From where she was bound on the table, Alison watched the other girl. "It looks like it really turns her on," she thought. "I want to try it, but I'm still afraid it will hurt too much." Then her attention was diverted as James, who had been playing casually with her tits as he also watched Ken and Kelly, began to let his fingers start to roam lower. He stroked her bare pubes and her swollen pussy lips. His finger penetrated and began to work in and out. Suddenly he pulled his finger free and replaced it with his mouth. He began to lick her slit, letting his tongue swirl around her protruding clit and sometimes plunge inside her wet slit. She began to climb higher and higher from this treatment when she suddenly felt something cool and slick at her puckered rear opening. She instinctively tried to clamp down, but with her legs spread taut and wide she couldn't do much about it. Then the feeling resolved itself into James' finger which seemed to be covered with Vaseline. He relentlessly continued his slow assault and soon began to press this finger against her opening. It slipped inside and Alison tried to relax her muscles. James worked his finger in and out, a couple of times removing it all the way to return with additional lubricant. He pressed inside as deeply as he could and spread the slick stuff with a twisting, in and out motion. During all this his mouth never left her pussy and soon Alison was on the verge of coming again. The now exciting sensation at her ass was only adding to her arousal. But before she came the finger was removed. She soon felt another object, rounded and smooth, began to press where the finger had been. It felt as if the object was tapered, getting larger along its length and each push brought the intruder in a little deeper, stretching her to the point of pain, but never past it. Then the smooth shaft would withdraw only to return again, with a twisting motion and a relentless pressure, each time a little deeper. James began to suck on her clit and to press even more firmly on the object. Just as Alison felt she was about to split apart if he pushed it any more, he sucked particularly hard on her swollen nub, starting her into a shattering climax. At the same time he gave the object a harder shove and suddenly Alison felt it pop inside and her ring of muscle clamped down to find a smaller shaft still blocking her rear. But this was small enough that it caused no pain and anyway she was completely overpowered with her orgasm.

When she began to settle down again, she noticed that the object, whatever it was, produced a full feeling which was not at all unpleasant. James was looking down at her and smiling. "You like that, don't you?" he asked.

Alison smiled back. "It does feel pretty good, even if hurt going in. What is it?"

"It's a butt plug," James replied. "Just a second." He left and returned in just a few seconds holding up an object for Alison to see. The object was about six inches long, roughly cylindrical in shape, but tapering from a small, rounded end to a larger bump most of the way along the shaft. The large area, about an inch and a quarter in diameter, quickly tapered again to a thin, half inch, area and then flared back out again to a broad, flat region. The flare was obviously to keep the object from going all the way inside and Alison decided that this was probably what she had seen in Sue's rear up in the pilot house.