Jake Wesson had grown up sailing and diving and was a master diver and dive instructor by the time he turned eighteen. His father had rented a boat and took the family on a two week trip through the Caribbean. Jake's favorite memories were for that trip. He was trying to decide whether to get out of the Navy after six years as a SEAL. He decided to rent a sailboat out of the US Virgin Islands and invited his family to go along. Everyone declined except Glenna, his sister. She had been coped up a the law office working on real estate law, handling closings and property management issues. Glenna wrote articles for a local real estate investment association and for a trade magazine. She had also recently broken up with her long time boyfriend, Phil, who had moved to Seattle. She saw the trip as a chance to escape and jumped at the opportunity.
Jake left Norfolk on a Space A flight to Puerto Rico on Military Assistance Command (MAC) flight. It was free for military personnel to fly and Jake liked free things. Puerto Rico was night and day difference from the cold, dreary winter of Norfolk and Jake was glad he had traveled in baggy cargo shorts and a loose fitting, button up, short sleeve shirt. From Puerto Rico, he hopped a small charter plane to the Virgin Islands and checked out the boat.
It was a sleek forty foot boat with a single mast and beautiful white hull and sails. He checked in with the rental company and verified his credentials as a sailor and mapped out a route to take. From there it was time to wait on Glenna to arrive.
He hadn't seen his sister in three years preferring to stay on the Atlantic side of the United States and not return home. Their parents had died shortly after he graduated from BUD/s and he wasn't on good footing with Bill, his older brother by six years. Bill had taken over the family business and thought Jake was a traitor for striking out and doing his own thing. Bill had graduated from auctioneering school and settled in working and eventually married his high school sweetheart. They had two children by the time Jake was a junior in college.
Glenna stepped off the plane, walked the short distance to the terminal and was soaked with sweat. She was glad for the air conditioning and fanned herself with a magazine. She spotted her brother immediately and threw her arms around him.
"Let me look at you!" She cried pushing him back a step. She took in the six foot tall frame and the bulging, rippling muscles. His dark hair was cut short and his green eyes danced. His smile was devastating and it captivated many women's attention, hers among them.
Jake let his eyes roam her body. She was lean with a generous swell to her bosom and long legs on her five foot eight body. Her straight blonde hair fell below her shoulders and her own green eyes sparkled with enthusiasm and life.
They retrieved her luggage and struck out for the boat. After getting her settled, she changed into shorts and a bikini top. Jake was able to get an even better look at his sister.
Her stomach was flat and toned, well defined under taut, tan skin. Her D cup breasts practically spilled from her bikini top and her legs were lean and well defined. Jake let out a low whistle and shook his head.
"What?" She said self-consciously.
"If you weren't my sister, I'd be hitting on you."
"Same here, stud." He was without his shirt and his stomach rippled with a hint of six pack abs. His shoulders were broad and powerful and his arms thick and round like a professional wrestler. She always thought her brother was handsome but after seeing him for the first time in three years, she found him downright sexy.
"I brought some supplies on board earlier. Why don't you look them over and they we can pick up whatever you want in the morning? Right now, I'm starving, lets get something to eat and more importantly, I need a drink."
"I'm see you already started." She motioned to the bag with four empty beer bottles in it.
"I needed something to do while I was waiting for you."
"Let's go, I could use a drink myself."
They found a little restaurant and dined on seafood fresh from the ocean and drank Red Strip beer. From there, they found a bar on the beach and drank margaritas and Coronas well into the night. One of the bartenders leaned across the bar and told them what a nice couple then made.
Glenna blushed and was about to spill the truth when Jake leaned over and planted a kiss on her cheek and told the man thanks. Her stomach did flip flops and her cheeks turned a crimson red.
Early the next morning, Glenna awoke to the rolling of the boat as it plunged through the waves. When she came up on deck, Jake had the boat under full sail and tacking south again towards the island of Dominica. It had rained and there was a slight chill in the air. Jake was dressed in cargo pants and a light long sleeve t-shirt. Glenna rubbed her shoulders and settled in beside Jake on the cushioned bench. She propped her long legs on the wheel housing and wrapped her arms in her sweat shirt.
They sailed for most of the day before dropping anchor on the south side of Dominica. Jake lowered the small boat and they rode into town and ate hamburgers washed down with cold beer. After they ate, they explored the town and made plans for hiking and kayaking the next day.
When they returned to the boat, Jake went snorkeling again and Glenna lay out on the deck. Jake returned in about an hour and slipped up on the boat. Stealth and cunning were engrained traits from SEAL training and Jake used his powers to climb the ladder and creep across the deck without disturbing his sister. She was topless, lying on her stomach with a skimpy thong bikini bottom exposing her firm, well shaped buttocks. Jake ran his hand over his hair and then flung the water onto Glenna's back. She startled, turning to see what had caused the water to fall on her.
Jake was laughing at his sister's plight. She was mad but laughed when she saw him and rolled over to expose her large breasts. Jake's heart skipped a beat as he looked at the large brown auroras and hard nipples. His cock leapt in his shorts.
"I don't know about you but I'm pretty hot." She raised her legs and slipped off the thong. Jake got a glimpse of her well shaven pussy before she stood and dove headfirst into the water. She surfaced and taunted him.
"What's the matter Jakie? You don't want to go skinny dipping with me anymore?"
It wasn't the first time they had been skinny dipping together but the last time they had, was when Jake was ten and she was twelve. He had no idea about sex and certainly didn't find his sister sexy then, now was a different story. He shrugged, stood and stripped off his shorts before joining her in the water. They played, tried to dunk each other and flirted. Jake couldn't hide his hard on and after a while didn't worry about it any more.
Glenna climbed back on the boat and stretched out on the deck. Jake joined her and they lay side by side drying off. Glenna let out a long sigh and rolled on her side, snuggling up to Jake. She rested her head on his shoulder. Out of habit, Jake kissed her on the forehead and ran his hand up and down his sister's side from the firm rise of her ass to the dip if her side and up to her rib cage. Her skin was warm and smooth and his cock was hard again.
Jake wondered how far Glenna would let him go after all she snuggled up to him and they were naked.
Glenna herself wondered how far Jake would go. She wondered how far she would let him go. She wondered how far she would let herself go. Right now she was enjoying being close to a man. Since Phil left nine months ago, she hadn't been on a date and when Jake called about the sailing trip, she jumped at the chance to get away from home. She nestled her head and felt her brother's warm lips on her forehead again. His hand felt good stroking her skin and she was warm and content. Glenna opened her eyes and looked down Jake's stomach at his erect penis. It was throbbing and standing away from his belly. Her legs rubbed together involuntarily scratching the itch of her pussy.
Jake saw her legs rub together and knew the tell tale sign of a horny pussy. He ran his hand up to her shoulder and then trailed his finger tips along the outer edge of her breast. He wanted desperately to roll her over and take her but he knew that she was delicate and needed to be seduced.
His hand moved down to her ass and gently cupped her cheek in his hand. He squeezed it and then ran his finger along the crack of her cheeks before rubbing the small triangle where her back and cheeks meet. She let a small moan escape from her lips and Jake rolled her onto her back. He rose up on one arm and ran his hand along her stomach and down her leg. Her pussy lips were round and swollen begging to be licked and fucked but Jake wanted to wait, to drag out the seduction and make her beg for him. She was his sister and sex was a taboo subject between siblings. Here on a boat in the Caribbean, it didn't seem to matter.
Glenna moaned and readied herself for him to mount her and satisfy himself. Phil had rarely engaged in foreplay and was always eager to satisfy himself before her. Glenna rarely had an orgasm and after they had sex, she often finished the job when she was alone.
Jake kissed her stomach from her breasts to her mound and then down the inside of her left thigh. His hand rubbed the inside of her knee and then he kissed up her thigh again. His lips almost touched her pussy lips and could taste the juices soaking her skin.
She moaned when he moved away and kissed up her belly again. He had shifted so he was over her, his mouth was devouring her body. His hand lifted her breast and he kissed underneath it where the breast meets her ribs. She moaned again.
Her loins felt like they were going to explode and she wanted to feel him deep inside of her. Feel his lips on her nipples that ached from being so hard. Never in her life had she been so aroused. She hoped she could find a man that would satisfy her and pay as much attention to her as her brother. His tongue was drawing circles on her breast getting smaller and smaller converging on her nipple. His penis was rubbing against her thigh and occasionally the head bumped her pussy causing her to jolt and gasp.
He moved forward and drug his cock and balls across her stomach and sat up. He never touched her nipples with his tongue and that seemed to infuriate her. He was teasing her and her body needed release and satisfaction.
She looked at his cock. It was bigger than any she had seen. It was eight inches long and thick, the head oozed pre-cum and the balls and skin around the shaft were shaved smooth. What hair remained was trimmed very short. Her hand wrapped around the thick shaft and Jake let out a moan. That first touch always sent a jolt through his body and was a sense of relief from the dull ache. Glenna stroked his length and her fingernails tickled his ball sack. Her finger wiped away the pre-cum and she licked it from her finger tasting her brother's seed.
He bent over and kissed her forehead and down her neck. His body slid back down and his cock rested against her thigh. She lifted her hips to position his cock head and he shifted his body with hers making the length of his shaft run along her wet lips. She let out a loud moan and begged him to put it inside of her.
Jake gave her a wicked grin and kissed down her shoulder to her breast and then gently flicked her nipple with his tongue. She moaned thrusting her tit into his open mouth. He devoured it greedily sucking on her nipple kneading her other tit with his hand. She was moaning and groaning loudly now, her hips bucking into his and her body ached for release.
"Please, Jake, please make me cum."
He arched his hips and used his hand to rub his cock head along the length of her lips and around her clit. Her hips were bucking and thrusting as he stroked her clit. He moved the cock lower and the head slipped gently into her pussy. She gasped as he slid his cock deep inside if her.
Glenna had never felt her pussy stretch so wide and with each stroke of Jake's cock, her body trembled. A few strokes later and she went rigid feeling the built up passion release from her body in one of the most intense orgasms she had ever experienced.
She was disappointed because she came so early. Never in her life had she cum more than once and she wanted to last for her brother. He wasn't disappointed because he kept stroking looking to satisfy his own needs now that she had cum. His movements caught her off guard and she could feel the heat building once again. She moaned and groaned thrusting her hips to find the right position to release her pussy from the tension and eventually, she felt the crushing wave of orgasm wash over her.
Jake reached under her and grabbed her ass pulling her up against him and captured her legs straight underneath his making her pussy even tighter. He stroked again and again into her tightness feeling her body react and listening to the satisfied moans of his sister.
Glenna felt the intense friction of his cock in her pussy with her legs straight and his hand on her ass felt incredible. Jake was groaning from exertion and feeling his orgasm building inside his balls. Glenna came again under his menstruations and then she felt him pull out. She let out a dissatisfied moan and felt him rub his cock against her mound as thick, ropey spurts of cum covered her from her tits to her pussy. It pooled in her belly button as Jake stroked against her and caught his breath. Eventually, he rolled off her and they held each other close.
The rest of the trip was spent naked whenever they were away from other people. They made love often but they enjoyed each other's company even more, cuddling, fondling and kissing.