Paid Vacation - Cover

Paid Vacation

Copyright© 2005 by Professor James

Chapter 8

Erotica Sex Story: Chapter 8 - 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  

In deference to the heavy activity with Max and Elsa the men went easy on the girls the rest of the day. That's not to say that there was any lack of sexual activity. However, they held off on whipping and other painful stimulation. They girls were still often bound, teased and taken a number of times, but only occasionally had to endure a spanking or nipple clips or such torments.

But despite the heavy activity on the island, by the next morning none of the women was still really sore and all were more than willing for some more fun. After the free time following lunch James made an announcement. "We have two new comers..."

"All of them have certainly been coming," one of the other men quipped.

When the laughter died James continued, "As I was saying, we have two new comers. You others remember from last year - and, Sue, you remember from two years ago also - we have a special little celebration for first timers. So, in that tradition, we're designating today as 'Alison's Day' and tomorrow as 'Barb's Day.' Barb and Alison looked uncertainly at each other as the others erupted in loud cheers. James went on. "What this means is that from now until tomorrow morning, Alison, you will be the center of activity. So why don't we all go to the aft cabin and begin."

Everyone moved below decks and along the companionway to the stern. As they entered the playroom, James and Ken led Alison over to where the padded leather vaulting horse had been placed in the center. Ken leaned close to her and whispered in her ear, "Just go with it. You'll love it." She smiled back at him as he and James began to bind her ankles to the legs at one end of the horse.

Soon she found herself, legs spread apart and strapped to the legs of the horse, bent forward along its length. As James tightened a leather belt around her waist the leather of the vault quickly warmed against her bare skin where her belly and breasts were pressed against it. She expected she would probably have her hands stretched to the legs at the other end of the horse and then be whipped, but was soon surprised when James placed cuffs on her wrists, but bound them together. He then raised her wrists toward the ceiling where he attached them to a short chain. The other end of the chain was anchored to the ceiling somewhere directly over her back, so she was soon pulled up in a tight arch, held by the belt at the waist and pulled up and back by her bound wrists.

"All right," James said. "Let's see what we can do for her." With that he and Ken each began to tease a nipple as the others quickly moved around her and began to touch and tease where ever they could reach. With a total of eighteen hands and nine mouths - not to mention the rest of nine totally bare bodies - Alison felt like she was being stimulated everywhere. Fingers danced over her sensitive skin; mouths sucked at her tits; tongues licked her everywhere, especially up and down her open slit and even around and into her anus. Within five minutes with two people sucking her nipples, others squeezing her tits, a mouth - she couldn't tell if it was male or female - sucking her hard clit, and another tongue pushed into her rear she came and came hard.

But nothing changed. Everyone continued to stimulate her. She soon was coming again. And again. For forty minutes the constant stimulation continued: nine pairs of hands, nine mouths and tongues, occasional touches of cock and tits. With each orgasm her skin seemed more sensitive and she could hardly stand the exquisite pleasure. When she was nearly exhausted James slowed the attentions. As Alison lay - or more correctly, hung - in her stretched position, the hands retreated and she was lowered for a few minutes rest.

But soon Bob and David came forward once again and pulled her bound wrists back up to the chain, arching and stretching her. Alison tensed, expecting them to begin toying with her body once more, but instead they stepped back. Then her head suddenly jerked up as a cat struck her across her ass. Soon there were nine whips tormenting her, the women swinging theirs with at least as much enthusiasm as the men. Blows landed on her taut bottom, her thighs and back, and around onto her breasts and exposed belly. Tightly stretched as she was, Alison couldn't do more than jerk hard against her bonds at the stinging blows. This whipping was nothing like she had suffered on the island, but the constant barrage of the leather lashes was again beginning to bring her near climax.

Then the lashing stopped and Kate and Kelly approached her from either side. As Alison looked from Kelly over to Kate she suddenly saw that each had a nipple clamp in her hand and Alison groaned in anticipation before either woman let her device close tightly over Alison's nipple. The two girls tugged on the clamps to make sure they were well settled and as they stepped back, James and Joe moved up and added small lead weights and set them swinging. As they retreated the lashings began once more. This time Alison did come. And as she shook in orgasm, the bouncing weights added to her already overstimulated condition.

As soon as she began to come down she expected to be allowed to rest a little again. But instead Ken moved behind her bound form and she felt his hard cock begin to push into her soaked pussy. As he moved slowly - oh, so slowly - in and out, Barb and Sue moved beside her and began to play with her dangling tit clamps. Joe moved around in front and stepped up on something so that his cock was directly in front of her mouth. Alison had opened her mouth and begun to lick at the hard member when she felt another tongue - later she found it was Kate - begin to lath her clit.

When the two men came, two more took their place: Bob at her mouth and James behind her where he pressed his hard shaft against her tight rear opening. His cock was covered with lube and soon Alison felt the long tool sliding into her rectum even as Bob began to spurt down her throat. Ken joined the fun with his mouth sucking her clit and his hands roaming her stretched body. Then Ken replaced Bob and she began to suck him as another mouth began to work on her pussy. When James shot his load into her rear he was replaced almost immediately by another penetrating shaft, but this one was plastic and attached to a very feminine pair of legs which Alison felt press against her sore buttocks as the plastic shaft was pushed into her distended bottom. For over two hours the sexual assault continued with short breaks. A couple of times Alison was lowered and allowed to rest a little, but most often her "rest" consisted of additional whippings and other torments. At the end of the time she felt exhausted, sore everywhere, stretched beyond belief, and had cum dripping from every hole.

Finally she was untied. As Kate and Kelly helped her to straighten up, James said, "Why don't you two help Alison get cleaned up and then take her to one of the cabins for a nap. After all, she still has a lot of her day left."

Alison looked up at him, startled. Surely they couldn't keep this kind of stuff up at that level much longer. James smiled at her. "I should explain. I said it was 'Alison's Day' until tomorrow. However, we'll let you sleep a while this afternoon. I'm sure you'll need it. In fact the other girls can take care of making and cleaning up dinner. After dinner everyone will have a little free time, as usual, and then we'll come back here for a few more games. Then tonight, Alison, you get to stand watch with everyone."

Alison groaned as the others grinned at her. James continued, "That means you'll be spending the night topside. I believe David would normally have had you tonight, but I think he and Bob will be sharing Kate. Everyone will have a watch, as usual, but you will be available for all of them to play with. I think you'll agree it's going to be quite a night."

The two other women helped Alison to the head and to shower. She needed help as she was about to fall asleep standing up. Then they took her to one of the cabins. Just before Alison closed her eyes, Kate asked, "Having fun?" Alison looked at her and smiled, but couldn't seem to manage an answer. "Well, I think I felt about the same way last year. But that night - The Night of the Watches - was one of the hottest of the whole trip. You'll love it."

Kelly added, "Kate's right. Last year at the end of 'Kelly's Day' I was sore, exhausted, stretched like you wouldn't believe, but I couldn't get the grin off my face. You'll see." Alison smiled in response, but her eyes shut almost immediately.

As they left the cabin Kate said, "We'd better get topside. I'm sure the guys want to play with us and I don't want Sue and Barb getting all the attention."

Kelly laughed. "No, me either. But remember they'll be saving things for Alison, so I wouldn't count on as much sex as torture. But that's pretty hot, too." Grinning, the two made their way up the ladder to find Barb and Sue tied to the rape racks getting their asses reddened with leather paddles. Soon Kate and Kelly were bound front to front, hanging by their wrists, as two of the men lashed their bottoms with cats.

Sometime later Allison was awakened by Kelly gently shaking her shoulder. "Supper time," she said.

Allison blinked. She slowly sat up and amazed herself by finding she wasn't really tired at all and - almost impossible to believe - actually looking forward to the night and even feeling horny. "I'm not sure I'm hungry," she told Kelly. Then she grinned and added, "At least not for food."

Kelly laughed and replied, "Well, you'd better eat some anyway. You're going to need your strength." She handed Alison her silver nipple chain and Allison noticed that Kelly was already wearing hers. "Better make a quick trip to the head. Dinner is just about ready."

A couple of minutes later Kelly and Alison entered the forward cabin to find everyone else there and food being served. Alison was greeted by a number of ribald comments and a few touches from the men. She took her place and found she had the honor of being first to be served. As they ate the meal, Alison tried to get some idea of what would be coming, but everyone refrained from saying anything useful while implying a variety of coming stimulations and punishments.

When the meal was finished Alison was allowed to remove her chain and accompany the men topside while the other four girls cleared up. On deck a couple of the men kissed her, but no one started anything. Instead they spent the time talking just as she might have expected under more normal circumstances. Or maybe this was normal. Except for the fact that she was naked. A few minutes later the other four women appeared on deck and the men let her join them, resting on the forward part of the boat.

The next two hours passed quietly but Alison found herself actually becoming excited by the prospect of the activities to come. She knew she was going to be stimulated more than ever before, even if not exactly how, and she expected a lot of it might hurt and leave her sore. Still she found herself wet as she thought about it and thought to herself how two weeks ago she could never have imagined this in her wildest dreams. And, she thought, she had had some pretty wild dreams at times.

By eight thirty when the men called the women to come below, Alison was more than eager. This time when they entered the forward cabin, the men had moved the padded table into the center. Alison was placed on it on her back, her waist near one end, and then had her legs lifted high and wide. Her ankle cuffs were attached to ceiling chains, bringing her legs vertical and spreading her feet a yard apart. Her wrists were pulled back and anchored to the other end of the table and a waist belt held her down on the leather top.

Alison realized this position opened her up, exposing her pussy and anus as well as making her bottom available for spanking or whipping. But rather than fearing this she found she was looking forward to it. Of course she knew that any whipping, while it would undoubtedly hurt, would not cause any real harm. Otherwise she surly would have been afraid, but Alison looked at all of this as an exciting game. And the game started almost immediately as James brought a wood paddle against her exposed ass with a loud slap. All five of the men gave her several swats each using several different kinds of paddles. Then the women started. When Sue landed her last swat, Alison looked up, her eyes streaming tears, but her breath coming in excited gasps and a wide smile on her face. Sue leaned over and licked her tongue across Alison's red ass and on into her dripping slit. As she moved her tongue up Alison began to strain and tremble and when she reached the bound woman's clit and sucked hard on the excited nub, Alison exploded into orgasm, straining against her bonds.

They let her recover for less than a minute and then two male mouths clamped onto her nipples while a hard cock penetrated her wet core. Over the next hour she was taken by each of the men and each of the women. She lost track of the number of penetrations of her pussy and ass and the number of cocks and pussies presented to her mouth. She was whipped with several cats again, tickled until she was gasping for breath, and had her breasts and nipples manipulated until she thought they were too sensitive to touch. She came a dozen times or more.

When it was time for the first watch, Allison was released and Kate and Kelly once again led her in for a quick shower. As soon as she was dry, Kelly and James escorted her topside for the first watch.

Alison spent the next two hours stretched in a standing spread eagle at the edge of the cockpit. She had her tits whipped with a suede flogger. Vibrators were used in both of her holes. Kelly spent nearly twenty-five minutes tickling her with a large feather while she was impaled with James' cock deeply embedded in her rear.

When the watch finally ended at midnight, Alison had come several more times and already felt stretched, sore and tired - but very, very happy. As Joe and Barb came up for the next watch, Alison noticed that Barb's bottom was marked with red lines, probably from a cat. And she looked frustrated. When she came near Alison, she whispered, "Joe's been saving himself up for you, so I haven't been laid and I'm horny as hell." She grinned at Alison. "So I may just take it out on you, girl." She let her hands grasp Alison's breasts and kissed her full on the lips."

Alison responded to the kiss and as Joe came up behind her he said, "Now, now. We can't have that yet." He pulled Barb back slightly and then placed her front to front with Alison and tied her in a tight spread eagle against the other woman... Then he spent twenty-minutes working them both over with a cat. Sometime after the first couple of minutes he stopped and inserted a double ended dildo into the two women. Before he quit both women had come several times.

He released them and let Alison stretch for a minute. Then she was retied on her back, arms and legs spread. Barb squatted over Alison's mouth facing her feet. Joe lay on top of Alison, pushing his member inside her, his head lying between Barb's legs. While the bound woman licked and sucked at Barb, Joe slowly fucked her. He'd withdraw nearly all the way and then slowly push himself back inside. Alison realized he must have tremendous control as he took a full thirty seconds on the inward stroke. And then just as long again on the withdrawal. And he kept it up. For more than twenty minutes he slowly fucked her. Barb came a couple of times but kept Alison's tongue and mouth busy. When Joe finally began to lose his restraint, Alison was so sensitive she screamed and began to come on his first fast, deep thrust.

Alison spent the next half hour stretched upright once again with the wind driven ribbons Ken had used on her the first night teasing her nipples and pussy. Joe and Barb also spent a lot of it teasing her, tickling with fingers and feathers. Barb worked a dildo into her rear and occasionally started it vibrating whenever she thought Alison could use a little extra stimulation.

Near the end of the watch, Alison was released and allowed a trip to the head along with a quick shower. When she returned the next watch was just starting with Bob and Kate. David also came with them and Alison remembered the two were sharing Kate for the night. What she found was that really David, Bob, and Kate were sharing her for the next four hours.

During these two watches Alison was subjected to a nearly non-stop stream of stimulation: paddlings, whipping, tickling, as well as vibrators and dildos and sex of every imaginable form. At one point she was stretched atop David while Bob fucked her ass and Kate helped where ever possible. Then everyone switched and she found David's cock in her mouth, Bob's in her pussy, and Kate pounding into her stretched rectum with a strapon. Before the second of the two watches ended, the four had tried at least two other arrangements.

Once again Alison was given a short break to go to the head and shower and then the last watch started with Ken and Sue. By now it was dawn and Alison was exhausted. But she was given no rest. Ken tied her to one of the rape racks and ravished her pussy before changing to her rear hole, all the while Sue was on the deck below her, licking and sucking at her nipples and pussy. When Ken finally came, Sue donned a strapon and started on Alison's pussy from behind while Ken alternated teasing and tormenting Alison's breasts. Before the watch ended, Alison received another working over with a couple of cats and then Ken took her again, this time in her pussy while Sue fucked her rear hole.

As eight o'clock came, Alison was nearly asleep and almost becoming numb to stimulation of any type. But she felt totally satisfied. Kelly, who was up early after having had the first watch, came topside and helped Sue take Alison below. After a shower during which Alison nearly fell asleep standing up, they helped her into a bunk and then went forward to join some of the men for breakfast.

Several hours later Alison woke and started to get up. She groaned slightly and realized she felt sore everywhere. Her tits ached, her pussy lips were swollen, she felt stretched both front and rear, and her ass, legs, and most everywhere else still registered where the paddles, straps and whips had fallen so many times. But she also felt wonderfully - what? - LAID, she finally decided. Yes, she'd loved every minute of it. Even if she didn't think she could have taken much more. She moved slowly towards the head, her muscles feeling better by the second, and realized she hadn't stopped smiling since she had opened her eyes. In fact, she was almost laughing. She decided that despite everything she had never felt so good.

When Alison finished in the head she went topside where she found everyone else in "free time." Everyone greeted her and a number made cracks about the grin on her face as well as the gingerly way she was walking. She gave each of the men a long kiss and then joined the four girls where she also kissed each of them.

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