Paid Vacation Pt. 02

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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.

Ken stood and looked directly into her eyes. "Oh, I think you can," he said, and let his hand slide down her bare back and across her tender ass. As his fingers caressed along her crack and ran lightly over her anus, he added, "In fact, I haven't even begun here." Alison groaned again, but soon Ken was working a well lubed finger in and out of her tight rear and she was responding. When she neared another climax, Ken slowly pulled the whip handle from her pussy and knelt to place his tongue between her legs instead. He spent the next twenty minutes or so eating her to several more climaxes.

This time Alison could barely lift her head and even Ken's nibbling and sucking at her nipples failed to bring more than a few new groans. Ken saw that she was nearing exhaustion and released her from her bonds. As he removed the ropes, Alison nearly fell to the deck and would have had not Ken caught her against him. "I guess I'd better let you rest a little," he said, "but we do have a half hour left on the watch." With this he helped her to sit on the edge of the cockpit. The well was just deep enough that when standing the edge came to about the middle of Alison's thighs. Ken stood her with her back towards the edge, facing into the cockpit, and then fastened her ankles to the walls of the well, about two feet apart. He then laid a couple of cushions behind her and had her lie back onto them. This placed her buttocks against the edge and raised her pubes. Finally he bound her hands to the deck out beyond her head. When he was finished, Alison was lying stretched tightly on her back, bent back at her waist with her pussy raised and opened between her spread legs.

For the next half hour Ken and Alison talked quietly with Ken occasionally stroking her bound body. By the end of the time the young woman was beginning to become aroused once more and Ken, who hadn't come at all yet, was sporting a long, hard cock. Finally Ken moved between Alison's legs and slowly began to push his erect member into her wet and waiting slit. He slowly pushed himself as deeply inside her as he could and then froze. Alison responded and her internal muscles began to clinch and squeeze him. Then Ken began to move in and out, but slowly, oh so slowly. He would bury himself as far as possible, freeze in position for several seconds and then begin a long, slow withdrawal until just the head of his large cock was still inserted. Then he would begin again. He was beginning to have trouble holding himself back and Alison was pulling desperately against her bonds when suddenly James' voice startled them. "I see you're not quite finished with your watch. Want any help?"

Ken and Alison turned and saw James with a naked Kate, her hands bound behind her, standing just above the cockpit. Breathing a little hard and fast Ken replied, "I think I can handle it, but feel free to watch."

James laughed. "Oh, I will. If you don't want my help would you like Kate to give Alison something to do?"

"That might be interesting," Ken replied. "Go ahead." James then led the bound Kate around until she was standing just beyond Alison's head. He helped her to kneel and position herself with her knees on either side of Alison's head. He indicated to Kate that she was to start and watched as she lowered her pussy against her roommate's mouth. Alison didn't need any extra urging and began immediately to use her tongue. For the next several minutes James watched as Ken fucked the bound girl, his movements becoming faster and faster and Alison ate Kate to two orgasms before starting one of her own in response to Ken finally going over the top himself.

When the three began to calm down, James clapped and helped Kate up once more. Ken stood and then released Alison from her bonds. As James began binding Kate tightly against one of the poles in the cockpit, Ken and Alison headed below. They stopped in the head again for a quick shower and then returned to their cabin. Alison later only remembered Ken once more binding her face up on the bed and then she dropped off into a deep and relaxed sleep.

When she opened her eyes again there was sunshine streaming through the porthole and she could hear some voices elsewhere in the boat. She looked around and saw Ken, leaning on his elbow, looking back at her. "What time is it?" she asked.

Ken looked around at the small clock by the bed. "About ten. No one gets up really early unless they had an early watch, but, then, no one will stay in bed later than about eleven either. We'll get up and find some breakfast soon, but first..." He bent over her and sucked her right nipple into his mouth, rolling it around and stroking it with his tongue. Within seconds Alison was becoming hot and arched her back to help him. In another couple of minutes she was straining against him as he plunged in and out of her. When he came Alison was only seconds behind him.

The two showered and went forward, stopping in the galley to dig out some fresh fruit and breads. As they entered the forward longue Alison saw that Joe and Sue and Bob and Kelly were already seated and eating their breakfast. Everyone seemed relaxed and it suddenly dawned on Alison that this would have seemed pretty odd even a day ago: Six of them, all stark naked, all knowing what type of games had been played overnight, sitting together eating and talking as if it were typical. "Well, maybe here in Wonderland it is typical," Alison thought to herself. Then she smiled inwardly and mentally added that she seemed to be very fond of this strange Wonderland herself.

While they were finishing they were joined by the remaining two couples for a short time until all the men decided to go topside. "Free time until after lunch," James called as they left.

Kelly looked over at Alison and asked, "Well, did you find out if you liked taking it up the ass last night?"

Alison blushed, which in her present state of undress, was an interesting sight. Then she thought, "What the hell, we all know what we're here for." She answered, "As a mater of fact I found that I loved it. I never imagined anal sex could be so hot."

"I told you so," Sue grinned. "There's nothing to compare with it."

Emboldened, Alison asked, "Sue, I saw that early yesterday afternoon they had a plug stretching your rear, also. Was last night your first time, too?"

Sue laughed deeply. "No, not at all. In fact I've loved anal sex for a long time. This is my third cruise with these guys. The first year was my first experience with the back door - and I loved it then, but when I came back last year the guys all commented about how tight I was, just like I was a virgin all over again. What I didn't mention is that I do regular exercises to keep my ass nice and tight. I mean inside. Girls who have too much anal sex and don't watch it can get stretched a lot and I didn't want that to happen. So part of my regular workout included tightening my back hole. This year the guys just wanted to loosen me up a little first. They also know it turns me on to wear a plug."

Alison was fascinated. "You mean there are exercises to keep you tight there? You'll have to show them to me because after last night I don't think I ever want to give up taking it in the rear."

"It is hot, isn't it?" Sue replied. Then she added, "At least with guys who are careful and take it easy. These guys are great but you will want to watch out who you try this with. But, sure, sometime I'll show you my workout routine."

The girls chatted for awhile, mostly about sex, the men, and the cruise. Barb and Alison were curious about what they might expect for the rest of the time and the other three gave them a few hints, but left most to their imagination, knowing from their own experiences that it would be hotter that way. Once Barb mentioned that she had heard two of the guys talking about a figurehead and wondered if anyone else knew what that was all about. Kelly, Sue, and Kate exchanged glances and then Kelly said, "Let's just say that the figurehead leads the boat." Kate and Sue giggled and Alison and Barb looked at each other, confused, but let it drop at that.

After a little bit the girls went topside and spent the next hour sun bathing until it was time to get some lunch together. Then after eating, everyone went topside again and they spent another half hour dozing in the sunshine. Finally James stood up and called to everyone. "I think maybe it's time for some fun and games, don't you?" He was met with cheers from the men and interested looks from the women. He went on, "I think the first order of business is to find a figurehead for this afternoon. Since we have two new members I suggest we let Barb have the honor today and Alison tomorrow."

Again the men enthusiastically agreed and were joined by the three remaining women. James took Barb by the arm and led her towards the bow, followed by the rest. As he went to a locker and began to remove some stuff, two of the other men unlashed a wooden pole which was hinged near the prow of the boat and laid back along the deck. They lifted the pole into an upright position and moved Barb so that her back was towards it and her face towards the bow. The pole was perhaps ten feet long and about six inches across. A small stool was brought over and Barb stood on it. Her wrists were fitted with heavy, padded leather cuffs and she was directed to raise her hands over her head where one of the men quickly lashed them to the end of the pole. James returned with a coil of soft rope and a couple of pieces of leather. The thick pieces of leather were used as padding as the girl was tightly bound to the pole at several points: above and below her elbows, her upper arms, above and below her breasts, her waist, three places on her thighs and below her knees and at her ankles. The padding and soft rope allowed tight binding without really hurting and by the time they were finished Barb - and Alison - had guessed what was coming. The pole was rotated on its hinge and soon it was leaning out from the bow at about a fifty or sixty degree angle. Barb, now bound to the underside of the pole, hung out over the water and did, indeed, look a lot like the carved figureheads that used to grace sailing ships. She was bound so that she could barely move, but there was enough rope and padding to prevent any real pain as she hung out over the water, occasionally being splashed by the salt spray, and looking out at the waves, her taut breasts projecting forward. Loud cheers demonstrated the approval of the men.