Paid Vacation - Cover

Paid Vacation

Copyright© 2005 by Professor James

Chapter 5

Erotica Sex Story: Chapter 5 - 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  

Allison had expected this night to be as sexy as the previous one, and her expectations were most definitely met. Bob (and she) had the midnight watch, which left them only two hours to sleep first. They didn't. Allison spent the entire two hours tied on her back with Bob constantly driving her to one orgasm after another with his tongue, his hands, a dildo, and other toys. And once bringing her to a shattering release with his hard cock sliding deeply in and out. When Bob released her just before twelve, they only had time for a quick shower before going topside.

When they arrived on deck Allison saw that James had Sue tied against the cockpit wall, but unlike she had been tied the previous night, Sue was facing the wall, bent forward with her hands tied spread in front of her. Her ass stuck up invitingly, pushed up farther by a couple of cushions under her hips while the tension of her bound arms pulled her breasts flat against the deck. Her bottom appeared to be mostly red with a number of darker stripes and when Alison looked she saw that her legs appeared to be wet with slick paths leading both to her pussy and to her anus. James was standing naked behind her holding a short tailed cat and with his cock still semierect and slick with their juices.

The two men exchanged comments while James released Sue. As he was leading Sue towards the ladder, she turned towards Alison, smiled broadly and winked at her. Alison returned her grin and realized suddenly that despite a stream of orgasms over the previous two hours, she was once again hot and looking forward to more sex. Bob was watching Sue's tight rear as she left and Alison was thinking to herself that she could hardly believe the men's - or her own - sexual appetites. Even two days ago she would never imagined she could be so turned on so much for so long.

She was thinking so hard about this revelation that she almost missed Bob saying, "I think maybe we'll go forward tonight." Bob had remained naked also and now took Alison's bound hands and led her towards the bow. He stopped her in front of the pilot house and in a few seconds Alison realized what he had in mind. In less than a minute she was tightly stretched over the "rape rack" again, bent forward at the waist, her legs spread and tied to the deck, her hands stretched wide and tight in front of her.

Bob spent several minutes teasing her sensitive spots, hardening her nipples and starting her dripping once more. Then he stepped back and picked up a flogger with a number of soft tails about a foot and a half long. For the next half hour he alternated stinging lashes with feathery tickling touches. The whipping wasn't severe but he spread the blows all over her exposed body. By the end of thirty minutes Alison bore marks over her tits, all sides of her thighs, her back, belly, and especially her taut ass.

Finally he laid down the whip and picked up something Alison couldn't see. He moved against her hot buttocks, his hard cock pressing upwards between her legs, but not entering her yet. He reached around and began to pinch and pull at her nipples, rolling them between his fingers and tugging them erratically. Suddenly Alison found out the identity of the items he had picked up as he let the first of the nipple clamps close sharply on her right nipple. This was followed a few seconds later by a similar pain on her left side. He stepped back and once more began to rhythmically whip her ass, somewhat harder this time. When her bottom felt like it was on fire, the beating stopped and Alison felt a slick finger enter her rear hole as Bob's other hand slid over her hot skin. A few seconds later Bob's hard member pressed relentlessly against her tiny opening. Alison forced herself to relax and allowed the hot shaft to bury itself deeply inside her rear. Not that much relaxation was required. She was already so hot and ready that in seconds she was pressing back against his penetrating strokes trying to get him in deeper and deeper.

Alison spent the rest of the watch bent over the rape rack while Bob alternated floggings and other punishments with sexual stimulation. He used his tongue to bring her off twice more and repeatedly worked her up almost to the point of no return before frustrating her. When Joe appeared with a bound Kate for his watch, Alison was stiff and sore, but could hardly wait to get back to Bob's cabin. He didn't disappoint her. Twice more before morning Bob's hard shaft brought satisfaction to them both, once in her hot vagina and once in her mouth during a long and intense sixty-nine. And when she finally woke to sunlight, Bob ate her to three more climaxes before untying her and joining her in the shower.

This day proceeded much like the last except that when afternoon playtime came, Alison found herself the figurehead. For three hours she hung from the angled pole, spray occasionally hitting her bare breasts. Before tying her to the pole, the men had inserted a medium butt plug and a small vibrating egg. These combined with the wind and spray to keep her at a constant sexual edge and when finally she was brought back onto the boat, Alison was more than ready for the two additional hours of sex play which followed.

At one point James lay on his back on the padded part of the deck and pulled her down atop him. As his long cock slid into her hot pussy, Alison was more than ready to ride him hard. But he held her still for a few seconds and suddenly she felt a lubed finger once more poking at her tight rear opening. This was followed a little later by Ken's weight pressing her into a tight sandwich and his hard shaft pushing it's way inside. Alison became lost in the sensations of their combined rhythm and it wasn't until after all three of them had come in hard climaxes that she realized she had just been fucked by two men at the same time as several others - men and women - looked on. Surprisingly, the realization didn't bother her.

Later as she watched, Joe and David pounded into Kate and Sue who were tied spread eagled on their backs. While Joe was nearing his climax, Kelly moved over beside Alison. She put her arm across Alison's shoulders and when Alison turned to look at her, held up a harness of some kind. It took Alison only a couple of seconds to recognize the harness which had held the strap on dildos she had experienced from the receiving end the previous day. She looked a question at Kelly but understanding began to dawn as Kelly started to place the harness around Alison's waist. She hadn't considered this, but found herself standing still as Kelly attached everything and also found herself becoming excited at the idea. By the time Joe pulled out of Kate's wet tunnel, Alison needed only a slight bit of encouragement from Kelly before she stretched over her roommate, pushing the fake cock deeply into Kate's willing body.

For the next several days the trip proceeded along the same lines. Alison could hardly believe the amount and intensity of the sexual activity and was constantly surprised by her own demanding appetite. She spent an evening with each of the men and then began over again with Ken. He kept his word and she spent the entire two hour watch tied tightly with the satin ribbons teasing and tormenting her hot body. Afterwards she was so hot that it was another three hours - and two fuckings and seven orgasms - later before she and Ken dropped into a nearly exhausted sleep.

About noon on the seventh day out the men brought the boat into a protected cove on a small island. They assured the girls that the island was one of many totally uninhabited so they were still free to play their games. The water in the cove was crystal clear and about thirty feet deep at the deepest. Everyone swam in the clear water and finally went ashore to lie in the sun. Sandwiches and cool drinks were brought over from the boat for a picnic lunch which was followed by naps and - surprise! - more sex.

Some time during the afternoon David suggested Scuba diving. It seemed there was plenty of equipment on the boat and Alison quickly discovered that Sue, Kelly, and Barb had all dived for a couple of years or more. Bob looked over at Kate and asked, "Well, what about you, Kate? I know last year you tried it a little and said you were going to take a class. Did you?"

Kate answered, nodding strongly, "I sure did. I still need the dive in open water to finish and get my card, but otherwise I've met all the requirements. And, for that matter, so has Alison. We took the class together."

Kate had talked Alison into taking the classes, but before long Alison had found she really liked the diving. She had been looking forward to summer when she could do the free ascent in open water and become certified. Now she began to wonder if Kate's true reason for the classes had to do with these trips.

Before she could think too much about it, Bob said, "Well, then, you are both in luck. David is a certified dive instructor and can sign you off."

David grinned and added, "That's right. Of course in addition to the free ascent in open water I'll require something else. Before coming up you'll each have to fuck the dive master." This brought several laughs, and David added, "You just think I'm kidding. Wait and see."

They all headed back to the boat and started getting the equipment out of the lockers. While they were getting everything ready, a couple of the men cautioned the girls about what to watch out for. The cove had a sandy bottom and the clear water didn't reveal any of the stinging corals, but they described them anyway. They were also warned about jelly fish and a couple of other things. Each girl would be partnered with one of the men, who, Alison gathered, were frequent divers and experienced in these waters.

As they started to don the equipment, Alison suddenly broke out in giggles. Ken, who was helping her on with her tank, looked questioningly at her. She controlled herself and explained, "In the YMCA pool they kept talking about the freedom of Scuba compared to the old style hard hat diving, but they never hinted at anything this free. In the Y pool, everyone still wore bathing suits."

Ken looked around at the ten totally naked people putting on their tanks, flippers, belts, and masks, but nothing else. "Well," he replied, "I'm sure they have no idea what they're missing."

The three experienced couples splashed into the water and set off exploring the cove. Ken, David, Kate, and Alison stood on the after deck while David explained the procedure. "I'll take Kate down first. We'll go to the bottom - It's about twenty feet here. - and sit down. Not really sit, of course, but settle on the bottom. Kate, you will take off your tank. You can keep the mouth piece while we complete the special requirement." He grinned at her and said, "I was serious. You're going to fuck the divemaster first. Then, when you're ready, take a breath, drop the mouthpiece and release your weight belt. Let yourself rise slowly, exhaling constantly. Remember, go up no faster than your bubbles. And above all, don't hold your breath. All right, are you ready?"

Kate moved over in front of him and put her arms around his neck, pulling him against her. She kissed him deeply and let her hand reach to grasp his hardening cock. When she broke the kiss she said, "Definitely. I'm ready for everything, especially the extra requirements."

David slapped her ass and said, "Well, then, let's go." They slid over the side and Alison watched with Ken as the two dropped down to the floor of the cove. Alison still wasn't sure David was serious about everything, but as she watched, Kate unfastened her tank and began to play with David's cock. David was feeling her tits and stroking her elsewhere. Once Kate lowered her head between David's legs and Alison wondered how she could possibly suck his cock under twenty feet of water. But that wasn't her intention. Instead she inhaled deeply and then let a slow trickle of bubbles out underneath his scrotum so that the rising air tickled and stimulated his cock and balls. The water was quite warm and it looked to Alison like David was hard and erect. This was confirmed when Kate spread her legs and David pulled her down onto his rigid shaft. The couple began to rock against each other and before too long they seemed to convulse and more and more frequent clouds of bubbles were released by each of them. They seemed to settle a little, David still holding her against his lap as their streams of bubbles returned to a more moderate rate. Finally Kate pulled back a little. David nodded and she removed her mouthpiece and began a slow ascent.

David waited a few seconds and then began to ascend about four feet below her. When Kate finally popped her head above water, David was only seconds behind her. As the two climbed back aboard, David said, "Congratulations. You are now a fully certified diver. Not to mention one really nice lay."

Kate turned and smiled at him. "Thank you, sir. But I really think it would be better if you didn't enter that part on my dive card."

David laughed and said, "OK, I guess I'll leave that off. Now, Kate, why don't you just wait here while I check out Alison. But I'm afraid I can't repeat the special certification test quite yet, so Ken, why don't you join us for that part. Thank you can handle it?"

"That sounds fine to me. Handling Alison is one of the nicest things I've done."

"OK," David replied. Turning to Alison, he asked, "Do have any questions? You'll do the same as Kate except you'll be with Ken while I watch. Don't try to come up until your breathing slows to normal and remember to watch your bubbles."

The three of them dropped into the water while Kate leaned against the rail to watch. When they reached the bottom Alison moved facing Ken while David watched from a couple of feet away. Alison had only been diving in the pool and, while this was deeper than she had been before, found nothing frightening in the slightly longer decent. If anything the water was warmer than the pool had been and the protected cove had no more in the way of currents. Besides, even though she was excited by the diving, the prospect of the kinky sex - yes, "kinky" was definitely the right word - was exciting her even more. She unfastened the straps on her tank and pulled them from her shoulders. The tank was still full and sank to the bottom next to her. She held the mouthpiece and reached for Ken. After a little play she tried Kate's technique with the bubbles and received a good response and Ken rose to the occasion, so to speak. Alison had never had a problem using the mouthpiece, removing and replacing it under water, and now she pulled Ken to her, removed her own mouth piece and tugged at his. He got the idea and released it and soon the couple was managing an intense underwater kiss. They broke apart and replaced their mouthpieces. Alison reached down and guided Ken inside as he pulled her down against him. As Kate and David had previously, Alison and Ken were soon rocking against each other nearing their own climaxes. When they came, almost together, they held tightly for a little bit and then, like Kate, Alison pulled back a little, removed her mouthpiece, and dropped her belt. She began to rise with David a few feet below her.

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