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Plundering Her Pirate Booty

Category: Anal Sex
02.10.2024
BadFairGoodInterestingSuper Total 0 votes
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So much preparation, planning, work on the venue and time spent on the costume. Elise and her best friend Thuy loved themed parties and would host one every chance they got. Last year’s combined birthday bash was a gothic theme. The guests that came put in the effort and Elise and Thuy quickly realized that if a person was willing to dress up, they were willing to have fun. A “Hippy Barbeque” followed that summer, but it was time once again for the girls to celebrate their birthdays together. Thuy thought up the idea of a “Pimps n Hos” theme and ran it by Elise.

“Do you think it’ll scare too many people away?” she queried. “I was thinking we could do it as a sort of play on words. The girls could be a Ho, Ho, Ho or even a Yo, Ho, Ho. The more creative, the better. I’m thinking of going as the Ho-stess!”

“Let’s give it a go, go, go!” Elise responded and started planning her costume. Both searched for a while before finally deciding. Thuy found a sexy Alice in Wonderland costume that she could modify to suit a Ho-stess. Elise found an all-in-one Pirate Wench costume that was sexy without being too risqué. For the final touch, Elise scored some high heeled pirate boots. It was time for the venue.

Thuy’s house was spacious and convenient and had ample parking. On the eve of the party, she and Elise strung lights and organized the snacks and bar areas. All that was left was putting on their costumes.

Thuy was a beautiful Vietnamese girl who grew up in the states. She had a great sense for fashion and although she was gorgeous, she never took herself too seriously. The Alice costume transformed into the perfect Ho-stess costume and she wore opaque white knee high stockings and black platform Mary Janes to complete the look.

Elise stood at about 5’10” and had dark hair and eyes. She had long legs that retained their shape and tone from years as a dancer. Her pirate costume was low cut in the front and super short in the length. She wore thigh high fishnets, a sash around her neck, a lace trimmed pirate hat and her super sexy boots.

There were lots of people and enthusiastic “Happy Birthday” wishes. So why wasn’t Elise having any fun? She was drinking bloody Mary’s and making her rounds. The conversations were nothing new. She wished something interesting would happen. Anything.

The music was loud and the party guests were well on their way to inebriation. She was feeling buzzed but wasn’t her usual “life of the party” self. She was distracted.

It had been a very long time since she remembered feeling this “attracted” to someone. Either she had gotten too picky as she aged, or the male population was just getting less and less appealing. And this area of the country seemed to be teeming with a sort of “grain fed” breed which didn’t appeal to her in the least. Even if she found one who interested her, he’d open his mouth and the twang would serve to kill any emerging arousals she may be feeling.

She shouldn’t allow herself to want. “Behave,” she’d tell herself constantly. Boredom was the enemy, it washed over her in waves and for the last 4 years, she’d been drowning in it. She got back into working with a new career and was really enjoying the change as well as the momentum she had gained. So how could this guy have blindsided her? She’d seen his picture on the company website and instantly recognized that he was different. Now he “appealed” to her. Thick hair, mostly gray, blue eyes, nice smile…hmmmm.

But when she met him, his indifference put her in her place. He was fit and handsome and sarcastic and aloof. Nothing phased him. And she wondered if she could get his pulse up? She wondered if she could get him up? His usual expression was serious and skeptical. But his face changed, lit up, when he smiled and she decided to do everything she could to make him. Each time he’d talk to her it seemed like he was giving her a hard time. He had a quick wit and although she fumbled over her words more than usual, she wouldn’t have it any other way. He was interesting. The more she saw him, the more she wanted him. He tested the waters at work but she held her tongue. Finally she had the chance to have a drink with him between appointments. She was excited and nervous at the same time. The professional wall came down a bit. She had to scurry away at a clients phone call but she looked forward to talking to him again. “This could be a problem….” she found herself saying over and over.

The next chance she had, she met him for a drink again. “One” beer turned into 3 and her words flowed a little too freely. Well, at least the elephant was out of the room. No more wondering. She made it clear that she’d enjoy getting to know him in “that” way and although he tried pretty hard to convince her that he wasn’t so harmless, she still had her doubts. She’d even invited him to her party though she knew he wouldn’t come.

As her fellow party host appeared to introduce her to a new guest, her focus returned to the party. She smiled, chatted briefly and then headed to the kitchen to refill her drink. As she mixed her next Bloody Mary, she looked out the kitchen window and saw someone in the backyard sitting in a chair by the fire pit. He was alone and wasn’t wearing a costume. The dancing flames barely lit his features in the late night darkness but she could tell he had light hair, maybe even gray. Her pulse quickened. She turned to look to the living room and noticed only a couple of guests lounging and talking. Most everyone else had made their way to the front porch to smoke.

She approached cautiously, almost as if she were afraid he was a figment of her imagination and might vanish when she got close enough. He sat there motionless. When she was within a few feet of him, his eyes looked up at her and he calmly said, “Well, it’s about time.”

She glanced around again then held out her hand. “Come with me,” she told him. He followed her to a corridor between the house and the garage. The only light that washed down on them softly was from the party lights suspended above. She sort of positioned him up against the wall and took her pirate hat off.

He’d seen her a hundred times but tonight she looked different. Her eyes were darkly lined and smoky and her lips were a deep red. Her costume was very short. Her spike heeled boots made her legs seem even longer than they already were. Black fishnet stockings disappeared under her red ruffled crinoline but he knew they were thigh highs and couldn’t wait to see where they ended. As he was looking her over, he felt her hand softly grab the back of his head. Without another word, she pulled his lips to her mouth. Her lips were soft and although they looked to be average in size, when she kissed them, they felt enormous. He could smell her drink and her skin. He liked the smell of her, not perfume-y but clean and slightly sweet.

She started kissing him a little harder now and he could feel the pent up passion that simmered for him. He opened his mouth a little and felt her tongue slip inside. He pushed his tongue back between her lips and felt her suck on the tip of it. His cock stirred in his pants and he could feel it begin to harden. Both of her hands were caressing the back of his head now and she was really getting into kissing him. He wondered what her mouth would feel like on his shaft and figured if she had half the enthusiasm “down there” that she was having “up here”, he’d be cumming sooner than he planned.

He reached forward and put his hands on her waist. He pulled her hips towards him. Her breasts mashed up against his chest and he pulled her against his now raging hard on. His hands found her ass and gave it a rough squeeze. As much as her costume turned him on, its usefulness was waning. His hands worked their way up her body and to the back of her neck where he grabbed a handful of her dark hair and pulled. His mouth found her exposed neck and as he brushed her skin with his lips, he heard her let out a little moan – she liked being handled this way. She was breathing harder now as he worked his way down from her neck to her cleavage. Her skin was warm and soft and he released her head and pushed both of her breasts up until they were spilling over the top of her costume.

He found the zipper and in an instant, it seemed, had the bodice unzipped and off her shoulders. It fell to the ground, taking the crinoline with it. She took a step out of it with one foot and kicked it to the side with the other. In the faint light he could see her – black lace push-up bra, lace thong, garter belt and fishnet thigh highs with red bows at the top. He ran his hands all over her and she came towards him and began kissing his neck. Her fingers started unbuttoning his shirt. She got it open quickly and brought her mouth to his chest. She licked at his nipples and when they hardened, she took one into her mouth, sucking on it and biting it just hard enough to give him a slight twinge of pain. While her mouth played, her hands were working on his belt and pants. Next thing he knew, she was on her knees in front of him. She liked the taste of his skin and now wanted to taste his sex. A drop of pre-cum sparkled on the tip of his cock when it sprang forth from his pants. She slowly licked at it and savored the taste of him. He looked down and watched as she started to gently stroke his cock with one of her hands. The other hand rubbed up his stomach to his chest. After she teased him for a little while with kisses and flicks of her tongue, she finally swirled her tongue around the head of his now rigid member and then took all of him into her mouth. He could feel her lips wrapped around his shaft and her tongue stroking the most sensitive underside of it. Her hand squeezed the base and he closed his eyes for a moment as he felt his dick sliding down the back of her throat. She was hungry for him and he knew it. She was enjoying the feel and the taste of him and she could feel the wetness between her legs. She had never had a problem getting thoroughly wet when she was with someone she was really into. And she was into this guy for sure.

He let out a muffled groan when she started licking and sucking his balls. When her mouth returned to the length of him, her hand moved from his chest to a soft sort of caressing of his sack. She sucked and sucked him. She found a rhythm he liked and he let her know that if she kept it up, she was going to get a mouthful of cum. His hips pushed into her and she loved the anticipation. The pre-cum that was now leaking from his dick was driving her on. She stood up and kissed him quickly and roughly so he could taste himself mingled with her mouth. She took his hand and guided it between her legs. He could feel her warmth and dampness through the lace, but when she pulled it to one side, her wetness coated his fingers. He liked knowing that she was hot for him. He slid two fingers into her wet pussy. She squirmed and then moaned her approval into his mouth as she kissed him. He brought his slicked fingers to his mouth for a taste. She tasted divine and before he could even suck all of her juice off his fingers, she covered his mouth with hers.

She wasn’t sure how much longer she could wait. His fingers in her pussy were driving her wild. He slid his fingers inside her again and she grinded into him for some satisfaction for her now aching insides. She wanted him deep inside her. But first, she wanted to feel him explode in her mouth. So when he withdrew his fingers to taste her sweetness, she disappeared and he felt her mouth again around his cock. He was sucking his fingers, she was sucking his cock. She found the rhythm that pleased him again. He put his hand on the back of her head and pushed her mouth deep onto him. He was going to cum and she knew it, she wanted it desperately. “I’m gonna cum in your mouth…” he told her and she sucked a little harder. She hungered for it and he wasn’t going to disappoint. She felt his balls begin to tighten as she messaged them. His hips pushed into her as his cock began to pump his cum deep in her mouth and throat. He was trying to be quiet, but it felt so fucking good. He came in buckets and yet she devoured every drop. When he finally finished, he was still semi hard in her mouth. He grabbed her face with both hands and stood her up to face him.

She was tall but in her 5″ boots, she was taller than him. He looked at her face and saw the satisfaction she felt from pleasing him. But she was ready for some release herself and he was ready to make her cum. He reached behind her back and had her bra unfastened in a snap. He almost ripped it off of her. He was ready to play with her full breasts and he quickly and roughly grabbed them in his strong hands. He squeezed them and mashed them together and rolled one of her light pink nipples between his fingers. He sucked the other nipple as he mashed his face into her tits. She grabbed his head and pushed her body against his – grinding her hips into him. He pushed his thigh between her legs and felt her rub on it a bit. She was hot and bothered and needed him to satisfy her. He spun her around and kicked her feet wide apart. He bent her forward and put her hands and face against the wall with her back arched towards him.

He knelt behind her and rubbed his hands up the back of her thighs, over her garter belts and then over the curve of her round ass. Leaning forward, he held his mouth an inch from her pussy. He pulled her thong to the side and breathed in her scent. Her pussy was shaved smooth with a small neatly trimmed patch above her slit and it glistened with her own wetness. He breathed a little warm breath on her skin to tease her. As she looked back over her shoulder with a wanting look, she pushed her hips back towards him. He playfully smacked her ass cheek and heard her let out a faint whimper. He squeezed the orbs of her ass and pulled her apart. He licked up at her slit with his tongue – she tasted better at the source. She was wet and tasty so he got to work. He stretched his tongue forward to lap at her clit and the moisture there. He flicked his tongue on her ass and then slid his fingers into her dripping pussy. Each time he’d touch her clit, he could swear it was more swollen and she’d buck and flinch if he rubbed it too hard. While he was eating her out, his dick had sprung back to life. And while he wasn’t certain he could cum again so soon, he wanted to see her pussy wrapped around his cock when she came.

She was close. “I want to ride you, I’ve got to feel you inside me” she told him and when he stood up, his cock was at full attention. He positioned the head at her wet opening.

“Wait…” he heard her say, “just like that, don’t move.” she told him.

He waited with his hands on his hips and watched as she slowly slid back onto him.

“Fuck yes…”was all he could say.

He watched in the dim light as the head of his organ spit her open. She was wet, very wet.

Her juicy pussy lips enveloped him. She used her arms to push and stretch her body back and onto his ever hardening shaft. After a couple of short, slow strokes she pushed herself back onto him roughly and he was buried in her.

“Yessss,” she purred. Gone was the doe-eyed girl he first met at the office. Maybe she was new to real estate, but she wasn’t new to this.

She swiveled and grinded her hips, she worked her body; it felt like she was milking his dick. She had control of the muscles lining her pussy walls and she tighten them and release them as she rode him. He wanted to grab her and fuck her dizzy but she was enjoying herself and he was too. He figured she liked to drive sometimes – and he liked the way she drove.

He saw one of her hands disappear and he knew she was stroking herself because when he was deep inside her, she’d reach to stroke the underside of his balls. “Grab my hips.” he finally heard her say. So he did.

“Now fuck me hard…” she ordered and so he did.

He slammed his hips into her with no mercy. “I am gonna cum soooo hard…” he heard her whisper so he kept up the assault. He didn’t know how loud she might get so he reached a hand around her face and covered her mouth. The other hand he placed at the small of her back to brace himself as he pounded her. This turned her on even more. She moaned in his hand as she came. Hearing her loose herself and feeling her insides spasm around his dick sent him over the edge. Months of pent up passion pinnacled and wave after wave of ecstasy radiated from her core. Just as she finished riding out her pleasure, he gave warning for what was building from his loins.

“Do you want me to fill that pussy?” he asked. “I’m gonna cum, baby!” he promised with a little more urgency. His second orgasm was just as intense as the first and he reached forward and roughly grabbed a breast in each hand as he pummeled her pussy. His head buzzed and his breaths were short and fast as he came deep inside her.

He pushed into her hot passage until every drop left him and filled her. Exhausted, he leaned forward onto her back as his racing heart slowed and his breathing returned to normal. His slightly softened member slid out of her drenched passage. She was breathing heavy and the tension in her body released.

He could feel her legs quivering and so knelt down and took a long lick at her oozing slit. His cum had started to drip out of her well lubricated pussy. He covered her pink puffy lips with his mouth and licked and sucked at it. She twitched occasionally as she felt the jolt of his skilled tongue on her now ultra sensitive pleasure button. When his mouth had filled with the mixture of his and her juices he stood up.

She spun around, almost reading his mind. This time it was he who pulled her face to his and he kissed her deeply as they passed the product of their sex back and forth between their mouths. It was salty yet sweet and she moaned into his mouth as she selfishly swallowed it all. She liked a man whose boundaries were as thin and broad as hers. Her instincts were right and the chemistry dangerous.

With the edge of their desire now softened, he kissed her more slowly and took the time to explore the erogenous areas of her neck. He liked the soft curves of her body and ran his hands all over her ass, stomach and full breasts. Her skin was fair with freckles and very soft to his touch. With his mouth on hers again, his left hand tweaked her small pink nipple and his right sought out her clit. It was still slippery and he felt another drop of wetness at her opening. He coated his finger and slowly circled her clitoris.

“Are you ready for round II?” he asked her.

“It’ll take me a while.” she told him. She had a recovery period as well.

“I’ll make you cum in less than 5.” he added with confidence and a hint of arrogance.

“Quite confident, are we?” she teased.

“Just results oriented.” he assured her with a sly grin.

His confidence (and arrogance) were a huge turn on and as she pondered his bold statement, he pushed her back against the wall and knelt on the ground in front of her. He loved these pirate boots she wore. They had her “pink parts” at just the right height. His face was level with her well trimmed mound and he looked up at her face with a devilish smile. She ran her hands through his thick hair and guided his mouth to her pussy lips. She rested her head back on the wall and closed her eyes and she felt his hand lifting her left leg up and over his shoulder.

It was her experience that few men really knew how to eat a woman out. She’d run into those overly enthusiastic types who watched too much porn and treated their tongue like a jack hammer and would nearly numb her clitoris. Then there were the guys who acted like they had just put down a step by step manual – they were robotic and less than inspired. But from the second that this guy stroked her, she knew that he wanted to please. He’d paid attention and she suspected he had pleased many lucky women. He ate her pussy like he was making out with it; softly with probing tongue thrusts and firm but gentle stimulation of her pleasure center.

She more than enjoyed the sensation and thought she may be able to hold out for longer than the 5 minutes he promised, but then his hands ran up the sides of her torso and found her breasts. He squeezed and massaged them. She loved the combination of sensations. Then he started to pinch her nipples; softly at first and then increasing in pressure until she felt a slight twinge of pain. Pleasure and pain was her magic combination. His face was buried in her pussy now and she held her own leg up to allow his strong hands to reach and play with her breasts. He alternated between sucking her pussy lips and clit and flicking his tongue over them.

It was more than she could resist. And for a moment, she didn’t care if he won this round. She was ready to throw out the white flag. She’d surrender to him anytime. The sensation in between her legs was a combination of pleasure and a sort of cool burning. He had teased and tortured her at work and although she felt consumed with letting him pleasure her, something told her that he got off on it as much as she did. And that is why her next orgasm was almost more than she could physically stand. The intensity made her want to cry out so loudly but she mustered all her resolve and kept her lips pressed together. Her arms searched out the solidity of the wall to steady her while everything else seemed to turn to jelly. His mouth was locked on her pussy lips and sucked the orgasm right out of her. She let out an almost guttural moan that surprised even her. Next came the ultra sensitivity in her clit so she instinctively grabbed his head to get a reprieve.

He looked up at her and his ear to ear grin told her that he enjoyed his victory immensely. She smiled at him and softly ran her hands through his hair. He could tell she was exhausted but he wasn’t through with her yet. All night he had thought about plundering her Pirate Booty and he wasn’t about to stop now.

He took her by the hand and guided her to a bench nearby. Her legs were shaking. He sat and pulled her onto his lap so she was straddling him. She wanted to taste herself on his lips again. They tasted heavenly mixed together. He stroked her soaked pussy opening and smeared it on her nipples. He sucked it off one while lubricating the other. He enjoyed kneading her breasts in his hands and pushing them together roughly.

“You tired?” he asked.

“No, just relaxed.” she assured him.

He reached around her and started to squeeze her ass cheeks in his hands. She kissed him and gave him an approving moan when his middle finger started circling her rosebud. The combination of sweat, cum and pussy juices had made her slick and the tip of his finger pushed against the tight opening then slid inside. He heard her catch her breath and so he paused for a moment but he felt her kiss him a little more intensely and he knew she wanted it as much as he did.

“Do you have anything left?” he asked her.

“Do you?” she asked in amazement.

“Always.” he told her.

“I have to taste that ass, my sweet.” he told her with a smack on her right ass cheek.

“By all means…” her voice trailed off.

He stood her up and guided her to her knees on the bench. Grasping the back of the bench, she looked over her shoulder in time to watch him disappear behind her. He was on his knees and helped push her knees apart a bit so she was spread wide in front of him. He licked her slit all the way up to her lower back. His tongue was so soft and warm and felt so good on her well used nether region. He wasted no time and his tongue was probing and licking her tight pink opening. His hands reached under her legs and up her stomach to her chest. He grabbed a breast in each hand and used them to leverage his tongue thrusts in her ass. He wished his tongue was six inches long. He wanted to taste all of her, deep inside her. She was clean and sweet and he knew she had prepared herself for him.

He wanted to devour her, he sucked at her and nibbled and even bit down lightly at times on the fleshy parts of her ass. His cock was awake and he stroked it as he ate her. He slid a couple of fingers inside her wet pussy and used her juices to coat his shaft. He pulled and tugged on his now rigid member while he ate her. She tasted fantastic and he imagined splitting her tight hole open. He stood up and positioned the head of his cock at her pussy and his thumb at her ass opening. Simultaneously he penetrated her. She looked back at him and he saw that familiar look in her eye. She was massaging her own breast and tweaking the nipple. She was ready.

When he withdrew his cock it glistened with her wetness. Her ass had adjusted to the thickness of his thumb but he wondered if that would be enough. He couldn’t wait any longer to ponder the idea. He slid his thumb out and pushed the head of his cock at her opening. She reached back and pulled her ass cheek for him. She arched her back and craned her neck to see but she couldn’t. She wanted to see him push into her. He pushed forward slowly to give her time to adjust. The head popped inside her tight hot hole. She winced and pleaded, “Slowly.”

He wanted to go slowly but the sensation got the best of him. Holding back took all he had but soon she relaxed and started pushing herself back onto him until he was buried balls deep inside of her.

“I want to feel every inch of you.” she purred. He could see the sweat glistening on her back.

He made long slow strokes into her. His muscles flexed and his eyes feasted on the view of her rosebud stretched around his veined shaft. It was hot and yet soft and amazing. Her breathing was heavy and she arched her back to him. She was sex to him, she oozed it. He put his hands on her hips, her smooth skin was on fire under his touch. He was ready to ream her, he wanted to release all the tension which had again built up deep in his loins. He was just getting ready to tell her he couldn’t hold back much longer when she spoke.

“Give it to me hard, really hard.” she said between heaving breaths.

“Oh, fuck yes…” he heard himself say without thinking.

She reached between her legs with one hand and braced herself on the bench with the other. She wanted satisfaction so badly. Her ass ached and yet felt intensely pleasurable at the same time. He was the perfect size for her and his long slow strokes had taken her to the edge of the cliff. She was ready to jump and he was ready to pump. The assault began. She stroked her clit roughly this time and pushed back against his thrusts. His hips slammed against her ass and his entire body tensed until the moment when all his desire bubbled up again. She was quickening and lost herself in the rapture of the moment. Theirs was a violent kind of dance. She told him she was coming and he could feel her tight passage tightening even more around his rod. He could feel it building in his stomach this time. And when he erupted, it sent shock waves through every fiber of his body. He grabbed her everywhere, her hips, shoulders, thighs, everywhere he could to experience the amazing sensation of cumming deep into her ass. He pumped gobs of cum deep inside her and then collapsed over her.

She was oozing his cum when he left the party that night. She had tried to redress and join the remaining guests, but found a quiet place in a back bedroom where she curled up and went to sleep.

The next morning her friend Thuy woke her up and asked, “What happened to you last night?”

She just rolled her eyes and smiled.

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