Breaking Her In, Again

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Brooke goes dark in the islands.
8.1k words
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It's odd how vision can deceive. Just inches from her extremely moist pussy, Brooke could clearly see the head of the black beast close, but not touching her, yet. Her inflamed outer lips glistened with a combination of sweat and natural lubrication. As the moved closer still, she swore she could feel the walls of her cunt stretching to accommodate this behemoth. Brooke imagined the front profile of the massive black cock actually pushing air out of its way as it neared her fleshy flower.

Brooke was laying on her back, watching the dark, muscular invader inch closer. From her angle it looked as if the outer edges of the coal black thug would completely cover her outer vaginal lips. Even though she wasn't scared, Brooke could feel her heartbeat racing. Brooke related the aggressive, high pitched sound of a sport motorcycle, ratcheting up through its gears, to the quickening beating in her chest.

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Brooke and Jim thoroughly enjoyed the few vacations they could put together each year. Typically, they and the kids would get way during the summer, when school was in break. Getaways would generally be a kid friendly destination like that "magical place in Orlando," or something similar. Keeping up with 2 young ones, especially while traveling, is less vacation and more Entertainment Director. Luckily, between the two of them, Brooke and Jim could divide and concur. While everyone usually had a great time, Brooke and Jim were typically not any more rested than when they had embarked on their journey.

When school was in session, Brooke and Jim would steal away for a week or so. Luckily, Jim's parents would happily come down and stay with the grandkids while he and Brooke snuck off to someplace much less kid centric.

Cold weather destinations were at the bottom of the list for either of them. Brook and Jim preferred beach destinations with sand, surf, dining and warm sea breezes. Brooke liked to bake her lithe body in the sun. Jim preferred to get wet, enjoying diving, sailboarding and deep-sea fishing. They both loved to sail; as many of their individual tastes could be accommodated using the sailboat as a central theme.

This year, Jim surprised Brooke with a week long sailing charter in the British Virgin Islands. They would fly into St. Thomas; then take the ferry over to Tortola to pick up their boat. Having owned boats in the past, Jim was an experienced sailor. Brooke had been with him long enough to know her way around a sailboat as well.

This trip would be just Brooke and Jim on a 41' Beneteau sloop. With all of the electronic conveniences these days, the raising or unfurling of sails was almost effortless. Once course was set, the autopilot would be engaged for hands free sailing. With slight course corrections during the day, the effort to move the boat from place to place was minimal.

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The midnight black, one eyed demon lightly touched Brooke's pussy. The moment skin met skin, she felt like she was being electrocuted. The combination of sexual energy, excitement and emotion crashed into her being.

The width of the black phallus seemed almost comical. However, there was nothing funny about this moment. The invader had made contact; now seeking to breach her fleshy petals. Brooke felt pressure, ever increasing on the outside of her pussy. However, she did not feel the usual yielding of flesh as when Jim pressed himself inside. Rather, she felt like someone, or something, was trying to push her whole body forward using just her moist cunt as the focal point.

Brooke reached down, extending her arms fully. She grabbed the edge of the elevated bed platform with her fingers pointing down. This would hold her body in place while the thick black intruder attempted to press into her. Maintaining a firm grip on the platform edge, she realized her body was slowly starting to yield to the intrusion. Slowly, constantly, the pressure pushing her body up the bed was replaced by her moist entry yielding. Her inner lips exposed, Brooke could feel the conically large black head trying to enter her body. Yielding lips, gave way to stretching skin, to the beginnings of pain. Just as the stretching of her opening began to transition to pain, Brooke felt the pressure easing, the dark as coal beast withdrawing.

A slow rhythm ensued. The black helmeted soldier would advance and withdraw; advance and withdraw. Skin to skin touch never ceased. The advance would always be just to the point where pain initiated; then it would ease. Brooke was shocked at the patience and persistence of the soldier's owner. Just as she was getting used to the rhythm of the advance and retreat, the advance pressed farther than last and stopped. Pressure, increasing and constant, pressed her inner lips outward.

"Now's the time Missus," he whispered in her ear. His sweaty lips grazed the edges of her ear. His shoulder length, black dreadlocks, created a little tent over her head. His words, accompanied by the English accent sang to her, easing her fears of impalement and pain.

Brooke stared into his eyes, "I don't think I can take it."

"Just think of it as your first time again, beautiful lady. It will hurt a bit at first but, in the end, you will crave the feeling. I'm finishing the job the first man that took you started." His wide, perfectly straight, white toothed smile, glowed back at her in her darkened dreadlock tent.

Brooke felt the warmth of his face as it approached hers. His warm, thick lips lightly brushed hers. Heads canted at the correct angle, both of their tongues sought out the other, meeting in the middle. A gentle tongue tug-of-war ensued; each pushing into the other's mouth, then retreating. Brooke felt her muscles relaxing, almost as if she had consumed a muscle relaxer. Her legs opened farther, now lifting to circle his sweaty torso. Just as she was about to tell him to breach her resistance, his tongue consumed every inch of her mouth. It filled her mouth, almost uncomfortably. She felt his left hand slide up her ribcage, casually brushing her soft, natural breast on the left. Quickly, he latched on to her nipple twisting it mercilessly. Tongue filled mouth, painfully cruel nipple twist, all gave way to the white flash of pain bleaching her consciousness.

The third day into the trip, their destination was the bay on Jost Van Dyke. Foxy's Bar was a must stop when hopping from island to island. It was so popular, the bay, and its limited anchorage spots, filled up quickly. Since it was one of the few destinations where you would likely have to set anchor, an early arrival was required to secure a decent spot. Many of the other destinations had buoys that could simply be snagged; tying off the boat securely. When anchoring at this location, skipper of the boat had to ensure two things. A proper hold on the bottom and sufficient clearance, from other boats swinging on their anchor axis during the changing tide, were both required.

Around 12:30 that day Brook and Jim started to see the island on the horizon. Winds were fair, seas were calm and the forecast for the next 2 days made no mention of degrading conditions.

By 2:00 p.m., they had dropped all sail and were cautiously motoring toward their preferred anchor drop. Jim couldn't help but marvel how delicious Brook looked, standing on the bow of the boat, giving directions with her hands in the air. Her tiny red bikini did nothing to hide her exaggerated chest. For a 50+ years old woman, her ass, while not a young adult's, was still scrumptious by any standard. Standing on the bow of the boat, making animated gestures with her arms, she put on quite a show with all the other boat crews that had already arrived.

Brooke signaled for the shift to neutral. She was judging the remaining forward energy the boat would have before it stopped. Jim started counting after putting the transmission into neutral. At the 30 second mark, and just as his own foot was making involuntary muscle movements, Brooke kicked out the stop on the anchor winch. Seconds later, the telltale splash of the anchor entering the water signaled Jim to start counting again. At the 20 second mark, Jim saw the anchor rode stop paying out over the side. Gloved hands in place, Brooke lightly touch the rope, testing for a firm set. Jim put the transmission in reverse. The boat started to slowly reverse course, more anchor rode paying out as he backed up. Calculating mentally, at the appropriate time, Jim signaled to Brooke to tie off the rope. After it was complete, Jim reversed again to ensure the anchor set. When he put shifted back to neutral, he signaled Brooke to test the anchor hold. Brooke bent over at the waist, reaching all the way down to the taught rope. The cheeks of her ass started to reveal themselves as she picked up the rope, testing the set. While not necessary, Brooke performed a series of overly exaggerated squats, seemingly testing the holding power of the anchor. Knowing ¾ of that dance on the bow of the boat was unnecessary, Brooke knew Jim would be watching her salacious performance.

Brooke dropped the rope and signaled for Jim to cut the engine. The engine noise, the vibration throughout the boat, all ceased to exist. Immediately replacing that manufactured engine noise was the delicate lapping of waves on the side of the boat and the breeze blowing through the rigging.

"Looks good up here," Brooke declared.

Jim smiled, right hand thumb up indicating "Looks great from back here as well." As he said this, his hand reached up to pull up his sunglasses and he said, "the only way this could look any better is if my crew was naked." Jim smiled as his eyes crawled over Brooke, starting from her toes, ending at her nose.

Being old salts at the game, Brooke and Jim proceeded to secure the boat. They threw out the hull bumpers, coiled and hung all the ropes, called the restaurant on the VHF for reservations and proceeded below decks to mix up the first round of cocktails. Around 3:00, Brooke and Jim were enjoying their first Rum Punch of the day. Jim queued some classic Bob Marley on the stereo. Just before the music started the two lavished in the silence of the moment, broken only by the waves on the boat and the far off drone of other boats coming in to anchor. If you've never been on a sailboat, when the engine in on, there is virtually no escaping the noise. It is virtually impossible to have a conversation between those in the fore and aft of the boat. However, to all other boats, the noise is barely noticeable.

About ½ of the boats at anchor had varying amounts of crew either moving about or mirroring Brooke and Jim's languid actions. The other ½ were either catching a nap before the night's activities or had already gone ashore to start partying.

The couple took in the beautiful scenery surrounding them. The sea was aqua blue and crystal clear. Standing on the deck of the boat, you could easily see 20 feet straight down. The sun was just starting its slow decent. This is a show that repeated itself each night. Around 7:30, the last bright rays would tuck below the surrounding island hills. All the boats at anchor followed the same choreographed dance, slow circling their anchor points. Most of the boats at anchor were owned by various charter groups. These were clean, white, well manicured vessels. The occasional local craft was interspersed amongst the sea of pristine boats. These were easy to spot, not quite as white, usually showing much more wear and age than the charter boats.

As their boat rotated with the rest of the pack at anchor, Brooke and Jim noticed a local had snuck in, unbeknownst to them. This was a much older Hunter 30'. The once brilliant white hull was weathered and oxidized. While it looked seaworthy, the old girl clearly had many miles on her. The sail covers, while intact, appeared weathered; the edges cracking from exposure. All of the hatches were open, but there was nobody visible.

Around 3:45, the first cocktail was about spent. Jim offered to make the next round, gathering glasses and heading below. While he was below decks, the boats in the bay danced around their anchor points again. The weathered Hunter 30 came back into Brooke's line of sight.

Hands on the back of her head, Brooke's legs were stretched out in front of her. She watched as a shadow, in the shape of a man, exited from below decks on the weathered boat. The distance was not a factor but the color of the man was. He was the darkest black man Brooke has ever seen. He had shoulder length black dreadlocks, which hid his facial features.

Brooke let out a surprised gasp. "Fuck," she yelled.

Her short but neatly manicured fingernails raked across the top part of his ass. She couldn't be sure but, she guessed he'd be feeling that when he hit the salt water again. Brooke reflexively tried to scoot out from underneath his grasp. However, with her legs wide around his torso, his left hand still firmly gripping her nipple and his right hand under head, across her shoulders; she had nowhere to go.

"Take it out, take it out right now"

"No lady, you need to breathe and relax, breathe and relax, you'll stretch out soon enough," he coached her. He released her left nipple. Shifting his head down, the dreadlock curtain brushed across her face. He began to gently lave and tickle her nipple with the tip of his tongue.

Brooke was breathing at a runner's pace. What was mostly pain had degraded to maybe a 4 on the 1 to 10 Scale. She was concerned she might hyperventilate if she had to keep this up much longer.

"That's right, keep breathing," he continued to sooth her.

Ever so slowly, the coal black thug started to muscle its way into her canal. One quarter of an inch in and back, in and back, the rhythm continued to cycle. Every 5th or 6th time, another quarter inch was taken in victory.

Level 4 pain continued to ease, downgrading to uncomfortable. However, due to the consistency of his stroke, Brooke was able to relax sufficiently to allow the intrusion without panic.

His mouth left her nipple, his lips again covering her own. The pink, extremely soft yet firm tongue snaked into her mouth. He aggressively sought the farthest reaches of her mouth, trying to take her mind off his campaign to completely fill her being.

Very slowly, while still very full, uncomfortable yielded to slightly pleasurable. Brooke continued to be shrouded in the dreadlock curtain. She could feel her body start to give over to pleasure, moisture starting to again release itself in her pussy.

"It's the widest thing that has ever been inside me," she declared in between tongue assaults. "I don't think my pussy will ever be the same, please keep being easy." Brooke let go of her first moan since the invasion escape her lips.

"Holy shit it's big, oh shit, fuck," Brooke continued her expletive laced rant.

By now, the black invader had gained about 4 inches depth. Slowly, methodically, the parry and thrust continued. Brooke moved her hands up to his shoulders. She tried to lift very carefully, her fingernails now raked ever so slowly from his shoulder blades. If she wasn't drawing blood, he would look like he'd been on the losing end of a cougar battle. Brooke smiled at the Cougar analogy. Although she was the one getting roughed up, she was definitely playing the Cougar role.

"How is that lady, you starting to relax," he whispered to her?

"I think you're going to ruin me for my husband," she whispered back.

"I told you, just like the first time lady. We just finish the job the first man didn't," his brilliant white smile almost blinding her.

Brooke's breathing was now converting to that of passion, not panic. Although a rare occurrence, when she looked between them, she could see that her pussy was creaming his thick black bludgeon.

Six or so inches in, Brooke recognized the familiar beginnings of her first orgasm. Her hips were starting to involuntarily rise up to meet his thrusts. Continuing to watch his black cock assault her poor pussy, she guessed he had 6 inches in and at least 4 more still had yet to cross her threshold.

Sweat started to ooze from every one of Brooke's pores. "That's it baby," she encouraged. "Assault me with it, make it your pussy. Come on, push it until it gets uncomfortable again. Take it from me, stretch it you black fucker," she aggressively whispered.

Unrelenting, the black invader continue to push in, like the Allied invasion of Europe in World War II. Each moment brought a new wave of invader to bear on the insides of her restrictive vagina. Lifting his body off her, bringing his pelvis backward, she could see the bulge of his cock coming and going below her navel. Brooke's first orgasm crashed her being like the knockout punch in a title boxing match.

This time, rather than searing pain, Brooke's vision was impaired by the throws of her orgasm. His aggressive stroking finally yielded her full impalement on the black mamba. Their pelvises meeting together was greeted with the largest squirt Brooke had ever experienced. The thin sheets covering the boat's upholstery were now soaked with mostly Brooke's ejaculatory fluids.

"You did it, you finished what the first guy started," Brooke gasped in her post orgasmic bliss."

"Yes lady, we've finally won the battle. Now it's time to start the campaign," his wide toothy grin shined back at her.

While Jim was banging around below decks, making the next round of cocktails, Brooke watched, transfixed on the shadow man and his boat anchored nearby. Slowly rising out of the cabin, Brooke could see only the pair of board shorts shadow man was wearing. From the distance, Brooke could not see the depth of detail on his rippled torso however, she could see that he clearly was fit. There was still enough sun to see the sweat, caused by the tropical climate, forming a brilliant sheen on his dark frame.

He appeared to be about 6'4 and a lean 200 lbs. He slowly looked around, taking stock of the surrounding, anchored fleet. As his vision crossed the anchorage, he spotted a lady sitting on a beautiful boat nearby. She appeared to be staring his way. Due to the sun at her back, he could not see the details of her features. However, he could clearly see the small red bikini she was wearing and the sunglasses shielding her eyes.

He moved to the front of boat, stepping surely and swiftly with practiced steps. Starting at the bow, he reached down to check the anchor line. Ensuring it was secure, he walked back down the middle of the boat; fenders over the side, sail resting properly in its housing in the "lazy jacks", boom secured and jib lines properly cinched. He stopped back in the cockpit, looking back again at the red bikini.

From his vantage point there seemed to be quite a bit of cleavage being restrained by the 2 small patches of red fabric. He stared back for a moment; frame erect, standing on the top of the cabin. Standing tall, he flashed a brilliant toothy grin, making a grand waving motion toward the red bikini.

As Brooke watched, she saw the board shorted shadow staring back at her. All of a sudden, he simultaneously waived and flashed a gleaming smile her way. Being under the canopy of the bimini top, Brooke was not sure how much of her he could see. Brooke stood up, ducked under the end of the bimini, standing confidently on the side of her own boat. Hanging on to the edge of the framed top with one hand, she turned slightly, offering a dazzling profile of her 34G tits. Brooke waived back with a broad side to side stroke. She hoped the vigorous wave she tendered back was enough to cause her red triangled display to shake. Having exchanged sailor pleasantries, Brooke ducked back under the bimini top, resuming her reclined position in the cockpit.