High Seas Adventures

Thursday:

Jake was sitting alone in his office staring at his computer screen. The monitor was showing the general weather for the Bahamas Islands. His nautical charts were laid out in front of him, faint pencil lines of previous trips criss-crossing the paper. He was the President of High Seas Adventures, a charter company that catered mainly to wealthy clients. Captaining a charter sailboat had been his dream since he was a young boy, but after 10 years of taking people to the same areas, showing them the same sights, and giving the same speeches over and over he was getting tired. He still enjoyed his job still loved the wind in his face and harnessing the power of nature to move him around the world, but the people were getting to him.

"Skipper, we've got a new reservation for this next week." His assistant, Tina, was poking her head through the door. Jake looked up.

"Huh? Were you saying something?" He shook his head side to side, clearing out the clutter that was causing him to stare into space.

Tina sighed. "Yes." She walked over to his desk, and dropped a manila folder on top of the charts. "We just got a new ten day reservation for next week. On the Wanderlust."

The Wanderlust was a 57 foot Beneteau sloop that Jake had bought the previous summer. It was perfect for medium length trips and large parties. It had all of the new equipment, and it was his new pride and joy. It's not that he didn't love his other 3 ships; they were like his children. But Wanderlust was the favorite.

"Great." He picked up the folder and opened it up. "Second honeymoon again?"

"No, it's worse than that. Apparently daddy is buying some college girl a trip for her and her friends for spring break."

Jake rolled his eyes. He'd done these trips a few times before. The last one had ended badly. The girls had gotten riotously drunk, and one had fallen overboard. Then, they insisted that he accompany them to the clubs to scare away any 'Uggos' that might approach them. He had worked hard to be a respected sailor, and he resented having to be a babysitter. He looked at Tina. "I hate you for this."

"Yeah, yeah, but we all got bills to pay." With that, she turned around and went back to her desk in the lobby of their office.

Saturday:

Dawn was breaking in the marina. Jake was making the final preparations for the voyage. He checked all of the sails and rigging, making sure that everything was in order. He went over his Coast Guard checklist for all the required items. Then he went below and checked the galley. He normally cooked for his guests, and this trip would be no exception. The refrigerator was fully stocked with food and beverages. He'd even stocked the liquor cabinet and verified that he had plenty of mixers. He knew college girls really just wanted to drink, so he might as well accept it.

Sitting in the cockpit, he looked at his watch. 8:15 am. He looked up just in time to see a duffel bag flying at him. It hit him squarely in the chest and knocked him backwards.

"Mornin' Skip. Need anything?" Jake sat up to see Ray jump from the dock to the deck. Ray was one of his regular mates for the Caribbean runs. A good kid of 23, he was still in school, but he always skipped class to come on trips. He was a good navigator, and so Jake overlooked his cavalier attitude...most of the time.

"Hi Ray. Grab me a Coke from below?"

"You got it." Ray went below to stow his gear and grab drinks for the two crewmembers.

They sat there drinking their caffeine and chatting about life for a solid half hour before Jake saw a limo pull up to the end of the dock. The driver got out and opened the rear door. One by one four young women stepped out and stood in the sunlight, looking around. The driver went back to the trunk to gather the luggage.

"Oh, Skipper, we sure know how to reel in the good stuff." Ray's eyes were about to pop out of his head.

"Easy Ray. You're a professional. Go help them with their bags, will ya?" Ray jumped up and ran full out to the top of the dock.

A few minutes later, Ray began to lead the foursome down the ramp toward the Wanderlust. When they had reached the boat, Jake stood up and stepped onto the dock.

"Good morning ladies. I trust you had a good journey here. Let me first say, welcome to the Wanderlust. I'm Captain Tucker, but you can call me Jake. You've already met my First Mate Ray Faccio. You can just leave your bags on the dock there; Ray and I will get them in a minute. Now just step aboard, and we'll get you all settled."

Jake took a step backwards so that he had one foot on the boat and one on the dock. He reached out his hand for the first girl, who he assumed to be the one whose father had paid for the trip. "And who might you be, miss?"

"I'm Allison MacDougal, I arranged this trip. These are my friends." She took his hand gently and stepped onto the boat. Allison had soft hands, Jake noticed. She had a nice touch. She was good looking, too, and she knew it. She was medium height, about 5'5" with breasts to match her frame. But what Jake noticed most was her shoulder length red hair, blowing about some in the morning breeze. She stepped beyond him into the cockpit. "We're glad to be getting away this week."

"Nice to meet you Allison." He reached his hand for the next girl, a shorter, heavier, brunette.

"I'm Rachel. Rachel Jones." She took his hand and jumped next to Allison.

"Amy Reynolds," the shorter blond said, grabbing his wrist as she bounded past him.

"Kate Thatcher, Captain." Kate was also blond, but taller than Amy.

All four women were now standing there, looking back at Jake. "Ok ladies, follow me." Jake went below into the galley. The girls followed him, one-by-one.

"Ok, the crew quarters are back here, across from the galley. Or the kitchen, if you will." Jake opened a door to reveal a set of bunk beds. The boat had three very nice staterooms and this room was meant for the workers. But since these people were paying him, Jake always slept in here. Besides, he only used the room to sleep in, anyway. "Up forward, we have the Master Stateroom, and the Master Head is on the left."

Rachel giggled when he said 'head'. Jake, looking ahead, rolled his eyes and then continued.

"At the aft end, we have two additional staterooms each with their own head. All of the staterooms have double beds. The couch in the salon also turns into a bed if nobody wants to share." He looked back at the girls expectantly.

Allison spoke first. "Well, I'll sleep up front. You guys can fight it out for the other two rooms."

"Called it!" said Rachel and Kate, almost simultaneously.

"Fuck it all." Amy said, "I'll sleep on the couch."

"No, you can share with me." Rachel spoke up. "It'll be fine. I don't bite."

"Ok, well that's all settled then." Jake clapped his hands. "I'll go help Ray with your bags.

Back on deck, Jake and Ray brought the luggage on board, and stowed it in the girl's rooms. When they got back up topside, they girls were sitting next to the control wheel, not sure what to do.

Jake took control. "Well, that's all done. Why don't you all go get settled in and put your things away while we get us going."

All four girls smiled, and slowly worked their way below decks.

Ray manned the mooring lines, and Jake started the engine. They slowly motored out of the slip, and into the Intracoastal Waterway. They had been going for about 15 minutes, when they finally came to the open ocean opening, and they passed through the drawbridge into the waiting sea. 10 minutes after that, Jake ordered the sails raised and the motor cut and they were off.

The sound of the wind was blowing in Jake's ears when he saw Allison come back up top. He could see she had put her pretty red hair up into a ponytail. As she got farther up the ladder, he also saw that she had changed into a bikini. And this bikini did not cover much. She stood in the bright sun for a second, long enough for him to get an eyeful. He knew she was young, but she looked great. Her tits were a great size for her petite body, a full B cup, and the triangle of fabric did them every bit of justice. Her fair skin was slightly freckled, and his eyes fell down her perky breasts to her toned midsection, and onto the string of her bottom piece. She was gorgeous. Immediately, she turned around, and went forward to get some sun. Rachel and Amy came up next. Rachel was the shortest girl, barely over 5 feet tall, and slightly out of shape. None of the girls were fat, but she was just built that way. Her body type did provide her with some great assets though, with beautiful D cup tits that almost overpowered her figure. Her short brown hair was now hidden under a sun hat. Kate provided a funny dichotomy to Rachel, being the tallest girl. Jake guessed 5'7" and with long blond hair that came down below her shoulder blades, almost touching her ass. Amy was by far the smallest of the four. She was taller than Rachel, but much more petite. Probably only 95 pounds soaking wet, she had no ass and barely any tits, which she tried to hide with a larger bikini top.

Jake watched lustfully as the girls slathered sunscreen on each other and laid down on the foredeck to catch some sun. Jake glanced down at the GPS, and adjusted his course slightly. They were getting a good wind, and were making almost 6 knots through the water. He was becoming painfully aware of the growing erection in his shorts, and he was trying not to make it too obvious. He'd gotten into trouble once before for messing around on a trip once, and he wasn't keen on getting on the bad side of a rich father.

The girls sat soaking up the sun and casually chatting for the next hour or so while Jake kept them heading Eastward toward the Bahamas. Shortly after Noon, Ray announced that lunch had been prepared. The girls all jumped up and went below. Jake set the autopilot, and went below himself. They were far away from anything now, and the ship could steer herself for a while he had a sandwich.

When he got down to the salon, only Ray was sitting there. Jake looked at him and raised his eyebrows quizzically. Ray jerked his head toward the master stateroom, and Jake saw Allison emerge now covered in a sundress. The others joined them soon after.

"So, Allison, are you all celebrating something?" Jake looked at the young woman sitting cross from him.

"No, we just wanted to get away for a while. Classes are out this week, and I'd never been truly away from everything before. I thought this would be fun." She winked at Jake, a gesture that shocked him slightly. He shrugged it off.

"So you all go to the same school?"

Rachel spoke up. "Yeah, up in Indiana. It's just not the same to do spring break up there." The other three laughed.

The rest of the afternoon went by quickly. The girls got more sun, did some reading, complained of boredom, and finally sat in the salon watching the satellite TV.

When dinner came, the girls had some wine and a great meal that Jake prepared then fell asleep early from exhaustion.

Sunday:

It was after 10 when the girls finally got up. Amy went up top to get a look at where they were, and was surprised that they were at anchor. Ray was sitting behind the control wheel and looking through the storage cabinets when he saw her looking around.

"Good morning Amy. Welcome to the islands."

"How the hell did we get here?" She asked, somewhat confused.

"The Captain and I sailed in shifts through the night. It's a bad first day, but we get here a lot faster. That's why we didn't drink last night with dinner."

"Oh, you must be tired." She walked over to where he was rooting around. "What are you looking for?"

"Well, I took some catnaps." He grinned. "Ah, found it." Ray pulled out a mesh bag with several masks in it.

"Are we going diving?" Amy was excited.

"Well, snorkeling. We don't normally bring dive tanks unless someone requests them and they're already certified divers."

"Awesome. I'm going to go get everyone else." Amy turned back and went to wake her friends.

Within a half hour, all four women were back in skimpy bathing suits, and Ray was helping them pick out snorkel equipment. Jake, having just woken up, stumbled up on deck. Spotting four young half-naked women brought him back to full consciousness. It also came close to bringing him to full hardness. Allison jumped in first, followed by Kate, Rachel and then Amy. They were happily splashing each other in between stints looking at "Nemo."

Jake sat on the side of the boat, his feet in the water, resting his eyes, and trying to gather his thoughts. He heard the girls whispering about something, but it didn't register with him. A few minutes later Kate climbed up the swim ladder, and stood next to him, dripping seawater onto the fiberglass below her feet. Some of it was splashing onto Jake, and he opened his eyes. Kate was standing behind him, and he wasn't sure why.

"Sorry Captain, but a dare's a dare." Too late it dawned on him. Kate reached down and pushed him into the water. Although the water temperature was close to 80 degrees, it still shocked him to plunge in. Jake somersaulted underwater to get his bearings, and swam back to the surface. He grabbed the swim ladder, half annoyed, half really pissed, and stared at Kate.

"Oh, shit." Kate said when he got up two rungs of the ladder. Before he got all the way up, she dove back into the water, and swam a few yards from the boat.

Jake yanked himself up the last few feet into dry air. He felt somewhat funny, like he was missing something. He looked down and saw his naked penis where his shorts had just been. He whipped around, searching for them frantically. Too late, he realized that he was now facing four young and gorgeous women. He looked up slowly to see all four staring not at his face but directly at his dick. He was mortified. He started to cover himself with his hand, but just then the boat rocked slightly and he had to stabilize himself with both hands.

Rachel and Allison both saw him step out stark naked. Before he had realized it, they spun Amy around to see the show. Unfortunately for Kate, she missed the first act, having dove for her freedom. Allison was staring intently at his package. She had seen dicks before, of course, but only on boys and never on a man. Jake was bigger than her last boyfriend, and he was still soft, no doubt from the water. She stuck two fingers in her mouth and whistled.

"VERY nice Captain. I think you have an eel attacking you." The other girls giggled.

Jake was embarrassed. He put his hands in front of him, covering up somewhat. Of course, he knew he should be more embarrassed, but the thought of four hot women staring at him was strangely arousing. While he didn't have the confidence to flaunt himself, he didn't do a very good job hiding it.

"Sorry ladies, I seem to have lost my shorts." He smiled. "You don't see them anywhere, do you?" He was trying his best to be debonair.

"Well, let me see." Allison shouted as she swam toward the boat. Throwing her snorkel gear on the swim platform, she climbed the ladder and stood next to Jake. "Nope, I don't see anything. But I feel bad that you lost them. Tell you what..." She reached back and untied her top at the neck, letting gravity expose her breasts. "I'll make it even for you."

Jake was starting to get more aroused. He could feel his dick twitching behind his hand, starting to fill with blood. Allison pulled the top off completely, and flung it into the boat.

"Well, that's a nice thought Allison, but that's fine, really." Jake was still worried about some sort of lawsuit for exposing himself to a customer.

"Well, I also had a nice thought." Allison said, much quieter than she had been previously. "I think those girls need to see what a real man looks like. Will you let me show them?"

Jake swallowed. He wasn't sure where she was going with this. "What did you want me to do?" He cracked out finally. I have no idea why I am so nervous. I've been with my share of women before. Though, never this good looking, and never with three more watching me.

"Just move your hand." Allison took his hand and pushed it aside. Jake's semi-hard cock flopped downward. At full capacity, he was just shy of 8", and he was 5.5" when soft. He was more of a grower than a shower, but he knew he was still above average. Standing to his left, she moved her left hand across his stomach, gently grazing her nails against his skin. The light touch made his prick jump again. When she got to the base, she cupped her hand around the shaft.

"Allison..." Jake started to say something.

"Shhhhh. A dare's a dare, and we decided that this boat is our Vegas. What happens here, stays here." She gently moved her hand down the shaft until her small fingers found the head. She stroked his dick gently until he was fully erect. Her other hand moved down to his balls, and began rubbing circles on them. His prick was rock hard, and throbbing with every stroke.

Jake looked into the water, now keenly aware of six eyes focused on his package. It was only then that he heard the slap of wet fabric on fiberglass. His head shot left and he saw 3 bikini tops hit the swim platform. He looked back, and saw movement underwater. The bottoms came aboard next, and the brunette and two remaining blonds were now naked above the reef. Allison pushed him back slightly, until the backs of his knees were touching the bench. Jake sat without thinking, and Allison smiled. Now free from any concerns, Jake reached his hand out to caress her skin. His left hand moved around her side, and rested just above the fabric of her bottoms. His right hand rose up to above her belly button. Allison was rubbing more intently now, not hard, but with a purpose. He moved his right hand to jest below her left tit, afraid to go further. He was in an unwritten rule territory, and he didn't know where her line was. It was taking every ounce of self-control he had in his body not to grab her perfect tits. As if she sensed his trepidation, she removed her hand from his balls, and used it to guide his hand onto her nipple. As Jake slowly moved his fingers over her mounds, Allison went back to rubbing her hands on his pole. She was crouching over him now, and she began to kneel beside him. His left hand slid up her back, and her wet hair fell onto it. His hand stayed still, and she lowered her face into it. "Now, where do you think I should go next?" She looked him directly in the eyes. Jake pulled her head slowly toward his crotch, until her ruby lips were closing in on his completely engorged cock. Allison took it the rest of the way and parted her lips, taking his manhood into her mouth. "Ohh." Jake let out the breath he had been holding. It had been too long since a woman had sucked his dick, and now he was living in fantasyland. Allison's mouth moved up and down his hard cock, sucking in as she moved up. It had only been a short minute when his body caught up with his brain. "I'm going to come." Allison pulled her head back, and he shot his hot load over the side and into the Caribbean.

"So, when's lunch?" Allison was grinning from ear-to-ear, and trying her best to be cavalier.

"Shit, I need a minute." Jake sat back and took a deep breath. His penis was softening now, and his head was clearing.

Rachel, Kate, and Amy swam back to the platform. They climbed up the ladder one at a time, gave Jake a smile, then stepped over the swim platform, and back into the boat. Jake looked, and they had all left their swimsuits. He reached behind him for one of the towels he had put out for the swimmers. Wrapping it around his waist, he started back toward the cockpit.

He got to the top of the stairs just in time to see Ray's expression as he turned to see four nude nubiles standing in front of him. Ray almost dropped the platter he was carrying, but regained his composure quickly. Jake went toward him and helped him finish making the sandwiches for lunch. Ray got drinks for everyone, and they sat at the table to eat. After one sandwich and three margaritas, Rachel started to get chatty.