Fair Winds - Cover

Fair Winds

Copyright© 2024 by Rottweiler

Chapter 1: Pirates in the Caribbean

Romantic Sex Story: Chapter 1: Pirates in the Caribbean - The sequel to Still Waters.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Consensual   Drunk/Drugged   Romantic   Fiction   Rags To Riches   BTB   Polygamy/Polyamory   Interracial   Oral Sex   Nudism   Violence  

They sought shelter from the summer storm in a small cove on the south shore of Little Cayman. The 28-foot ‘Leopard’ had a shallow draft but a wider beam so Bobby set a second anchor for added security. With gusting winds up to 45 knots, it was prudent to be extra cautious. With the rigging secured and the dinghy set out with a double tether — there was little to do but wait out the blow inside the comfy cabin.

“Oh God Yes!” Tavia screamed as he buried himself to the hilt within her. She gasped for breath as he began humping her with rapid thrusts of his muscular hips. He held himself above her by planking his arms so he could marvel at her beautiful face and watch her delightfully large breasts bounce in rhythm to their lovemaking. He had just turned sixteen and she was his senior by 8 months. Despite their age gap, he was her hero and most magnificent lover. She had fallen for him two years ago as they were attending sailing and navigation classes at the Neptune Academy. Her skin was typically dark from her Jamaican roots while he had been naturally pale with light blonde — almost white hair. With generous layers of sunscreen and nearly constant exposure to the Caribbean sun, he had developed a bronze tan which still contrasted with her dark mahogany tone.


Despite her age, she was still a virgin when she finally seduced him on his 16th birthday. Their first time was magical and something neither would forget for the rest of their lives. It was a warm summer evening and the Leopard lay at anchor off the shore near the mansion where his family lived. The yellow-orange full moon hung overhead like a giant balloon. They had lain a thick comforter over the trampoline netting that spanned the foredeck between the hulls and reclined side-by-side on pillows staring at the stars that blanketed the night sky. An extra comforter lay at their feet in case it got cold during the night.

Tavia changed out of her typical bikini into a soft fleece nightshirt with matching shorts while Bobby just changed into another pair of shorts. He always felt at ease next to his best friend and the closeness of her warm body, combined with the gentle floral fragrance of her perfume made him feel giddy and lightheaded. He loved it when her soft hair drifted over his face giving him a heady dose of her unique alluring smell. When he sighed aloud, she turned herself to face him and placed her hand on his bare chest while her leg slid over his hard thigh, possessively. Her steel grey eyes glinted in the darkness and he shivered when her breath touched his ear.

“What is it?” she asked softly.

“I just couldn’t imagine this being a more perfect evening,” he replied.

She lifted her face to smile at him, “And what makes this evening so perfect?” Her accent was thick from her Jamaican heritage.

He shrugged and then the memories crept back into his mind from the dark cellar where they had remained buried for so long. His shrug became a shiver, which she took as a chill — pressing herself closer to him. “It’s kinda dumb, but I like being on the water — I enjoy the ocean and I feel at home here, under the stars, because — no matter how alone you feel — they are always there, even when you can’t see them.” His mind drifted back to a younger version of himself sitting alone on the deck of his treehouse, staring up at the night sky. “I always felt safe under the stars. And now I’ve learned to use them to guide me home when all else fails.”

She breathed in deeply through her nose, smelling his skin and hair. She sighed to herself as he continued.

“Being out here on the water, under these stars — with you ... it just feels right,” he admitted wistfully, causing her heart to flutter. “I love...” He stopped and abruptly sat up as a feeling of frustration came over him. Tavia gasped in alarm when he didn’t say what she had been longing to hear. She sat up with him and put her arm around his shoulder.

“Bobby, what’s the matter?” she asked fearfully.

He shook his head sadly. “I hate that word,” he muttered. “It’s such a stupid thing and it doesn’t even mean anything.”

She felt her hopes wither and her heart trembled as she slowly released her grip on him. Tears came unbidden to her and she shuddered tearfully as she drew in a breath. “Love? You think love is stupid?” she nearly sobbed.

He looked back at her in alarm. Then he turned himself to face her, regretting that he caused her pain. “It’s the word, Tia,” he tried to explain, “when I was growing up in that house, it’s all I ever heard from my mom and occasionally my brother and sister ... and my da ... uncle Frank.” He sounded bitter and she could see the tension in his jaw. “But they never once meant it. Only my dad ever meant it truly.”

She leaned toward him and wiped her eyes as she sniffed. “I love you, Bobby,” she whispered. “And that means something to me!”

He could feel the sorrow in her voice and he swallowed uncomfortably. “I believe you. And it is easy for you to say because I think you already know what it means to love someone or something.” His words had the opposite effect as she looked back at him with anguish in her eyes. She started to get up but he stilled her by placing his hand on her knee. “Tia, I don’t want to say I love you when the word doesn’t mean what I feel.”

She sniffed and swallowed with a quiver and she glared back at him. “Then what do you ‘feel’?” she demanded tearfully.

He took a breath and looked down as he considered his words. When he looked back at her she saw that something had changed. The insecurity was gone and she let him take her hand. “What I said earlier about the ocean, and how I feel I belong here — and the stars above us and how they make me feel safe and never alone. And being able to share it all with you. It’s completely perfect and I wouldn’t trade it for anything.” He stopped and took another breath. “The way I feel about you is all of that — and more.”

They sat gazing at each other for a moment in silence. He was surprised when she suddenly reached across and grabbed him in a tight embrace. Her lips found him and she kissed him urgently. He had never kissed a girl before but he instinctively surrendered his mouth to her and found that her taste and warmth caused a rush of emotion to overwhelm his brain. He moaned happily and she hugged him even tighter. Her lips tasted like passionfruit and mint and when her tongue entered his mouth he gasped as the contact shook him to his core. It was like static electricity and he suddenly realized the desperate need to wrap his arms around her and hold her just as urgently. He couldn’t get enough.

At some point, they were lying back on the pillows once more and Tavia had removed her shirt offering her full and perky breasts to him with her dark areolas and rigid nipples. It was an offer he could not have refused if he wanted to and he hungrily attacked them with his mouth and hands, driving her wild with desire and pleasure.

When he instinctively allowed her to guide his attentions lower, he could detect the heady aroma of her sex and he found she had doffed her shorts as well. Her legs parted for him and he found her pubis to be almost completely free of hair as he explored her nether regions. When he kissed her tight labia, she cried out and pushed her pelvis into his face, urging him to probe deeper into her. He ran his tongue and finger along the narrow slit, open her lips to reveal her hot and moist vagina. She was aching for his touch and pulled his hair urgently as she thrashed beneath him. He correctly assumed her moans and sighs were in response to his touching and licking and redoubled his efforts to penetrate her further. Her hymen blocked him and he knew enough to avoid rupturing it. She was even more reactive when he touched her clitoris, so he gave it his full attention for several minutes — licking and sucking it while she gasped and cried out to him, pleading him to continue. When she came it was her first orgasm that wasn’t self-induced. She screamed with pleasure and her body froze up in a convulsive state of euphoria.

“Oh God, Baby! Yes!” she panted as she recovered. “Oh my God! I want you so bad! Come up here!” She pulled him up her body and dug her hand into the waistband of his shorts, finding his throbbing erection and gripping it desperately.

He groaned into her mouth as he felt the thrill of her touch through his entire body. With her free hand, she tugged the shorts below his hips and he helped her slide them down his legs. Then he moaned and his brain shut down to its most basic program of survival. He had to breed and the feeling of his penis rubbing against her hot and slippery mons drove him crazy with desire.

She wailed hungrily at the feeling of his hardness pressing against her. “Oh, baby! Please! Put it in me now!” she begged him as she heaved her groin firmly against him. It proved to be more difficult than either of them thought as he pressed his head against her vaginal lips and met the tight resistance of her maidenhood. He grunted and held himself tightly against her and she cried out in pain as he began stretching her further open. “God! Just do it!” she cried. “Do it, baby!”

He felt conflicted by his overwhelming need to take her and the fear that he was hurting her. But his desire won out and he forced himself deeper into her with a groan. She screamed as her hymen tore apart but pulled him by his hips as she pushed up against him, completing the plunge until he was completely inside her. She wrapped her legs around his and held onto him tightly as she panted away the shock of losing her virginity.

“Don’t move!” she hissed through her clenched teeth. “Just stay like that ... for a moment.”

He felt her pelvic muscles twitch and seize around the girth of his cock as he held it firmly within her. Then he sensed her relaxing and she lessoned her grip around his body. “Oh my God!” she sighed and lifted her face to kiss him again. “Okay, please be gentle and slow,” she added, encouraging him to begin slowly pushing himself in and out of her tight channel. He tried to contain his urges. Occasionally she would hiss again and have him stop where he was for a second until the cramping tearing pain subsided once more.

Suddenly he felt his scrotum energize and he gasped as he began ejaculating inside her. He hissed out loud and groaned as he tried to resist shoving himself into her as hard as he could. “I’m sorry!” he cried and grunted with each spasm as his sperm squirted out of him. “I can’t...”

“Shhh. It’s okay baby,” she replied soothingly. “Just let it go and enjoy it. Give it to me!” she panted as she felt his warm seed squirt into her between the pulses of his erection. “Oh my God, it feels so good!”

Later they lay beside each other gasping for breath as they marveled at the sensations they had just experienced and shared.


Once again, they lay gasping beside one another but this time it was inside the warm cabin, safely sheltered from the seasonal storm that raged outside. Occasionally they felt the boat surge and sway and rock gently as a squall burst around them. The rain sounded like a thousand tiny hammers pelting the hull and cabin around them.

“I love this,” Tavia murmured happily into his neck as she held him beneath the warm comforter.

He smiled in the dark. “Mmm, me too.”

An occasional flash of lightning would invade the confines of the dark cabin followed by an immediate blast of thunder as the storm rolled over them. Subconsciously Bobby assessed the security of their double anchors, by the feel of how the catamaran rode the small waves that drove through the protected cove. They fell into an easy slumber as the waves rocked them gently to sleep.

When the sun crept over the horizon it shone in the forward portals lighting the small cabin brightly.

“You know, I had misgivings about catamarans at first but I have to admit that the Leopard is growing on me,” he said with a yawn. He sat up and stretched causing a draft of colder air to blow under the covers. Tai pulled the comforter tighter around her with a moan and poked him.

“Don’t be bashing my baby!” she muttered as she tried to recapture the warmth. Tavia Ashanti was the only child of a widowed marine biologist and professor at the Center for Marine Sciences at the University of the West Indies in Kingstown. Professor Ashanti was a quiet and brilliant Australian scientist who became solely driven toward academia after the death of his beloved Jamaican wife, to cancer. Tavia was 13 at the time of her mother’s death and she suffered greatly from the loss. Not only did she lose her best friend and confidant but the effect on her father drove him further from her.

She found herself isolated and on her own at a young age. Her father didn’t abandon her in the physical sense. But he became emotionally distant and the only way she could interact with him was by following in his steps, studying marine biology. When she opted to further her maritime studies, he purchased the Leopard and showed her how to handle it. The boat was a 26-foot Simpson Formula One fast cruiser and was easily handled by a single person. By fifteen, she had sailed all over the Caribbean on many solo excursions. Her pedigree assured her early enrollment into the Neptune Academy where she met Bobby.

They bonded instantly not only because they were the youngest cadets but also the most gifted. When they weren’t involved in their studies or underway on distance voyages, they met aboard the Leopard where he practiced his sailing, handling, and navigation skills under her expert eye. He soon proved her better in practically everything to do with sailing and ocean-going, but it was not something he lorded over. She adored his youthful energy and curious streak for adventure and knowledge. Tavia was not unaware of her feminine charms and modest endowment, and she fended off the sexual advances of many male admirers over time. Despite Bobby’s innocent naivete, she found herself attracted to him in a very like fashion though she resisted the urge to treat him differently than the close friend that he had become.

“I wasn’t bashing her Tai,” he replied modestly, “I have to admit that the design has grown on me. It is very well suited for the open waters around us.”

“Daddy grew up on the waters of Western Australia before he moved to Jamaica and met my mother. He lived on a version very much like this one, so he was sold on the craft when he decided to buy her for me.”

It was a solid design at that. The twin fiberglass hulls were connected by a solid main deck on which the cockpit and cabin sat. Under sail, she was sleek and fast and handled with surprising agility. When sailing was not an option or just not desired, she had twin 20-horsepower Yanmar diesel engines. She was also outfitted with a state-of-the-art SIMRAD multifunction navigation and piloting system.

“I can’t wait to be done with my classes at UCI,” Bobby sighed, “I would love to work with your dad on the Heritage Project.” He referred to a joint venture for the preservation of shark habitats. It was a collaborative project shared by several island nations and commonwealths including Grand Cayman, Jamaica, the Bahamas, Turks and Caicos, and Haiti.

“You just want to get a free pass to go cage diving,” she replied rubbing against him. It galled him to no end that he was disqualified from the one thing he wanted to do most of all — simply because he was a minor. The number of achievements under his belt was staggering for his age. His ‘uncle’ Kurt was a certified flight instructor and had been teaching him how to fly. He owned a Pipistrel Panthera that he bought from Slovenia and shipped to the GC. He also owned a larger Cessna 210 which he chartered, and an experimental SeaMax Light amphibian. So far Bobby had only logged hours in the Panthera but was intending to make his first solo flight soon. The running joke at home was that he was qualified to pilot a small freighter, operate a Dive Charter off of the Celtic Dreamer — the fifty-foot sailing dive boat owned by his dad, and fly a small single-engine plane. Yet he was too young to drive a car.

They were suddenly disrupted from their musing by a sharp change in the pitch of the boat. The starboard hull dipped ever so slightly in a manner that alerted them both that somebody had just boarded the Leopard! Bobby slid quickly out of the berth and grabbed his shorts as hushed voices came from outside the cabin. The sun rising over the bow foiled any view into the aft cabin portholes, but the shadow of at least one figure could be seen in the pilot house. Bobby looked out quickly enough to recognize that the intruder carried a rifle with a curved magazine jutting from beneath it. He turned back to Tavia in alarm and whispered, “Pirates” in her ear. She slipped from the bed and began pulling her clothes on while he quietly bolted the latch that secured the hatch into the cabin.

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