Private Tales Dating Dangerously

A private roleplay only for those invited by the first writer

Smiling One

Heartbreaker and Life Taker
Banned
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1,036
Character Biography
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Little Portshaw is a forgotten finishing village located near the shores of Arethril. It’s home to about 250 people most of them are fishermen who spend most of their time out at sea, giving the village a sense of emptiness. It was a poor village full of hardworking people scrapping by. Willis though felt right at home, it was a good place where travelers who didn’t wish to be found can disappear to. Not that he was on the run or anything, but it was nice to have a place to go and be alone away from civilization.

The villagers despite not having much, paid generously for Willis to get rid of any near by Owlbears, small Goblin raiders and Giant Spiders lurking near the village boarders. Those creatures were a monster hunters bread and butter and Wills managed to make some good coin slaying them. But a chance to rest and earning coin was not the main reason why Willis stayed here. It was because of a woman he met a while back: a pretty barmaiden who worked for the only tavern in village. She was free spirited, curious and loved the sea just like Willis. In many ways she was just like him.

Eryn Pere is a one of a kind woman, who eagerly listens to every story that Willis had during his travels. No matter exaggerated it was, Eyrn ate it up and expressed her desire to go with him one day. On the promise that Willis leaves and comes back for her. There was always a catch when
It came to women. Something Willis had a lot of experience with.

For now, the two enjoyed each other’s company. Fucking and exploring around the village and of course Willis enjoying Eryns sexy dresses. He now knew where Eryn spent her coin. Today they were going on another date, this time traveling away from the village. Eryn has never been far away from Little Portshaw and she was eager to get started.
 
She was excited to say the least. She felt like she's only known Willis for a short time, but already he's shown her more wonders than she could even imagine. She didn't even mind the danger at times, because Willis proved himself as a perfect protector when going on their outings.

She clung to him arm in arm as she walked beside him, smiling contentedly as they strolled along. Before Willis came along she was the tavern whore, making coin on the side to share with her boss. But now she has been subdued. She is now Willis's whore and would give herself to no other.

She didn't know what was in store for today, but she felt ready with Willis by her side.
 
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Willis smirked when Eryn looped her arm around his as she began practically dragging him out of the tavern. “Well good morning to you my lovely barmaiden,” Willis said stumbling after Eryn. “I see you’re eager to get going.”

Admittedly after the last date went horribly for the two of them, Willis was very hesitant in having the next date be outside of the village. Eryn on the other hand was very confident in Willis’ abilities to protect her stating that she will always feel safe around him. It was sweet, but Willis just doesn’t feel like the hero Eryn makes him out to be.

Eryn hadn’t slept with any other man ever since she started dating Willis, this caused some tension between the men and Willis but Eyrn did say that she was his whore and wouldn’t sleep with anyone else. It was a bold statement to make given that many men already sharpening the pitch forks to run Willis out of town.

“So today’s date,” Willis said opening the door and basking in the suns rays. “We’re going to a forest clearing I found in my travels. I see you’re dressed particularly sexy today.” He winked.
 
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She smiled and let go of his arm to skip in front of him and spin, letting her skirt billow around her and revealing her legs in her calf high strapped sandles. She walked backwards on the road in front of him with her hands behind her back. Her top was casual and rural looking. A blouse with a sleeveless vest tucked into a belt, but all but the last three buttons were undone, leaving a good portion of her bosom and cleavage exposed and open for his viewing pleasure.
"I'm glad you like it. But I wonder, would you still want me if I didn't dress as a slut all the time?"
She quirked her eyebrow at him and gave him one of her teasing smiles.
 
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Willis smiled when Eryn began to spin around in her reveling blouse. She moved with such grace, Eryn would've made for a great dancer in the troupes or better yet in the theatre. Willis loved it whenever Eryn dressed sexy it was a promise that she made to him that she would always dress in revealing clothing when they get the opportunity to date. Willis obviously didn't mind but Eyrn seemed to question whether or not that he would still want her.

"That's absurd!" Willis laughed picking Eryn in a bridal and spinning her around. "I would want you even if you decided to dress in a burlap sack. I mean given how beautiful you are Eryn, you'd make that burlap sack look good."

Willis knew that Eryn was teasing she was welcomed to dress into anything she wanted but Willis did prefer that she showed some skin every now and then. The two went into the forest, it was full of birds singing up in the sky and deer feeding on to the grass. Willis held Eryn close as he set her down. "So Eryn," Willis asked. "This is the first time you've been to the forest, you afraid?"
 
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Ah, Willis was definitely a smooth talker. A burlap sack indeed, she would hardly be caught dead in a burlap sack, though any situation she could think of herself dying in would probably end her up in a burlap sack.
As he carried her like the most lovable sack of potatoes in the world she giggled, his strength was a security blanket, and when he set her down in the forest and asked if she were scared she shook her head, staring up into his eyes.
"I can't be afraid with you. I've got the top monster hunter in Arethil wrapped around my little finger. I'm as safe as a baby in her mothers arms."

She stood up on her tippy toes with her hands on his chest and licked the tip of his nose playfully.
 
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Willis raised his eyebrows in shock but then smirked. Eryn always seems to find unexpected ways to pleasure him. Part of him wondered if the forest was safe, Willis did take care of the two Owlbears who injured one of the fishermen who drunkenly wondered into the forest. There were also a pack of Goblins who planned on stealing valuables from the tavern. They weren't using their heads so Willis took them off, still years of traveling on the road had taught Willis that forests can be the most unpredictable place in the world. With disease, wild animals and bandits prowling about.

He still remains astonished that Eryn has so much faith in him. There were times that Willis failed to protect Eryn like back in the cave where she was harassed by the bandits and carried off deep into the caves. Willis thought that Eryn would never trust him again but here she was declaring that she was safe around him. Willis smiled and kissed Eryn's neck squeezing her exposed breast while did so.

"I'm just saying as long as you're safe and happy. I'm happy." Willis said. "Now come on! You said you wanted to explore? Well let's go!"
 
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She sighed into his lips before moving back. It took a huge push of will power to not pull him under the shade of a tree and ride him right then and there. But she managed to pull herself away and fall in step beside him, looping her arm around his elbow while trying to match his longer stride.
The events of the cave were still fresh in her memory, but she was doing her best to be as strong as Willis. She tried not to let him see her jump at every shadow or sound of movement in the underbrush.
Even when they laid together in bed she would cling to him and bury her face in him to hide herself from her fears. Often she would drive him to ride her senseless or until she passed out just so the nightmares wouldn't plague her.

She walked beside him and just looked ahead, holding his arm tightly while she tried to control her breathing. She was never one for hiding from her fears, which is why she agreed to this date... But it wasn't easy as her heart pounded in her chest at every single unseen creature that went bump in the underbrush.
 
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Willis knew that Eyrn was still affected by the events surrounding their last date. Though Eryn smiled around Willis, dressed sexy and continued to bartend as though nothing happened, Willis could easily tell that the red headed barmaid was shaken from being taken away from Willis, feeling useless whenever Willis engaged in combat. Every night when they were in bed, Eryn would cling on to Willis like a child holding on to their mother. The young man was aware that Eryn wanted to offer Willis more than just her body but doesn't know what.

It was then that he decided that Eryn will learn to defend herself. She liked to call herself "Willis' whore" something that amused him but at the same time realized that if Eryn wanted to travel with Willis, then she'll need to be more than "his whore". Besides there were a few high tier brothels at Elbion where whores were taught to defend themselves. Specifically the brothel called the Maiden's Mashup located in the richer area of the residential district.

After the undead attack on Elbion a few hundred years ago, the brothel owner: Atheriel had decided that her ladies needed to learn some combat skills. Atheriel hired some Elbion knights to teach her ladies about self defense in exchange for free nights with the whores. Today, some of the ladies in the Maiden's Mashup were just as skilled as the average Monster Hunter people who go there often make sure that they don't rip off the prostitutes or force themselves onto them.

The sounds of water crashing signaled Willis that they were close to the location. Gripping Eyrn's hand, Willis smiled. "Do you trust me?" he smiled. "Because this date is going to be different, I'm going to teach how to defend yourself Eryn."

Brushing away the tree branches, Willis saw the clearing full of birds swimming in the water. It was perfect for their training, far enough and secluded so no one can bother them and at the same time, it's not too far from Eryn's home. "Welcome to our training arena!" The young man grinned. "You say that you're my whore right Eryn? Well if you want to travel with me you'll need to learn some techniques."
 
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He'll teach her how to defend herself? She took a deep breath and sighed. Finally, she wouldn't have to be afraid if she could simply have more confidence in herself.
She followed him into the beautiful oasis, and the sight took her breath away. She looked around at the serene scene around her, twirling in the grass as she took it all in.
"It's beautiful Willis! I can't believe I've never been here before!"

She ran back to his arms and kissed him before pulling away, a wide smile on her face, "Alright. What do I do first?"
 
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Willis found the grotto on his way back to Little Portshaw after taking on a contract killing Owlbears from another small village. Eyrn loved waterfalls, she would often drag Willis to the local river after a night of fucking and the two of them would just observe the water cascading down the jagged cliffs. Eryn was enthralled though Willis turned away. All he was going to say was that he had a long history of waterfalls though he did not tell Eryn that.

"I'm surprised given how you like to explore outside Little Portshaw," Willis kissed back while rubbing her nose. "My little whore," he winked.

Now to business, Willis was going to teach Eryn the bare basics of defending herself. He didn't want her to go deep into combat but at least it'll buy Eyrn some time while she runs away from danger. "So Eryn," Willis said approaching the barmaiden. "Let's say some big drunk guy looms over you while you are serving drinks. He wants to sleep with you but you refuse so the guy grabs you by the collar."

Willis placed his calloused hands around Eryn's collar holding it up. "So the first thing to do Eryn," Willis said. "Is to relax and breathe, always keep a clear mind in a fight no matter what. Check the scene around you to see if you can use anything to your advantage but if there isn't any. One thing you can do is to take your arms in the gap between where I'm holding you and wretch off the my grip as hard as you can."

The young man smiled. "Try it out." he said.
 
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Whenever he called her his little whore it always gave her a sense of belonging, she was his and that could never be questioned. But sometimes it also felt a little derogatory, like she was the scum on the bottom of societies shoe. Whenever he said it he made it sound like a compliment, but she couldn't help a little sinking feeling in her chest.

Still, she was happy enough to let it go as he took her collar and held her up in a tough guy grab. She took his advice and took a deep breath to calm down and focus... Mostly because him grabbing her like that got her really aroused and now wasn't the time to interrupt the lesson before it's even begun.

"Okay..."
She followed his instructions and attempted to wrench his hands off her clothing but failed to dislodge his fingers from the material, though she did succeed in grabbing his wrists and pulling them down which ultimately pulled the front of her shirt open almost dangerously.
"Oops! Don't think that's supposed to happen if I don't want the brute to sleep with me!"
 
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Eyrn would always call Willis his whore and that she wouldn't fuck anyone but him. The young man smiled, the two of them a Monster Hunter and a Barmaid considered to be the dregs of society. Once considered a glorious organization now and days, Monster Hunters were considered to be depraved or crazy given the level of violence that comes with their work and as for Barmaids such as Eryn? Well there was a reason why Bardmaids were popular people lay with.

The young woman focused and attempted to escape from his grip. Willis didn't account of the amount of force that Eyrn used to pull him down. He landed near her already exposed cleavage which caused him to nearly blush. "Well that's okay!" Willis said immediately pulling himself away from Eyrn's chest. "I mean men are often attracted to busty barmaids. You can use this as an opportunity, you want to fight pretty or do you want to hit and run? When an enemy is distracted always aim for where they're most vulnerable at!"

Willis hoped that Eryn knew where to aim for.
 
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Eryn chuckled and rolled her eyes.
"Men!"
She aimed a kick between his legs but purposely didn't let it connect, then she simulated gouging his eyes by pushing back on his brow with her fingertips.
She feigned offense with a little huff and pout as she pulled her blouse closed.

Her eyes danced with a mischievous glint.
"What if the man is already on me and between my legs? I can't really kick him in such a position."
 
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Willis shrugged while Eryn rolled her eyes. "What can I say?" he smirked. "We men are all bravado except when we lay eyes on a barmaid's cleavage," Willis winked staring at the Eyrn's exposed breasts she really knows how dress provocatively. The young man instinctively held his arm up the instant that he saw Eryn attempt to kick him in the groin. Willis then smiled when he realized that Eyrn held back. "Nice feint," was something he was about to say until he saw Eyrn about to gouge his eyes out.

"Ah shit!" Willis attempted to guard himself but even that was a feint as well. "Ah deception!" Willis said. "You are really good at faking an attack. The use of subversion is a useful tool in combat you can trick your opponent into defending an area leaving them open for your true target."

The young man ruffled her red hair as he frowned for a bit. "Well," he said. "You can do what you just did gouge out his eyes." Willis placed Eyrn down to the ground gently and was pinning her down by her blouse. "Now try to get me off you," he said. "Look for weaknesses in my attack and use it to your advantage."
 
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She couldn't help but get a little hot underneath his weight. It was true, when she attempted to kick or stomp him with her heals the strikes were ineffective without anything behind them and nothing to hit.
She was starting to breath a little harder as she attempted to buck his weight off her with her hips, but still to no effect. She bit her lip from the thrill her efforts gave her and probably him as she pushed herself against him. Finally she tried going for the eyes again, careful not to actually gouge him, and she focused on trying to move his head off to the side and thus hoping his body would follow his head.
 
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Willis could hardly feel Eyrn's strikes, she was fast and good at faking attacks but she lacked strength. Eryn continued to use pragmatic tactics going for Willis' eyes while attempting to move his head from the side. It was enough force to have Willis get off of her and rolled away. "Good," Willis said getting up. "You're fast and resourceful but you lack strength it's important that you always try to remain calm though and think on your feet."
 
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She was a mix of elated at successfully dislodging him, and disappointed that he was no longer between her legs. She rolled over and got to her knees while he critiqued her technique.
She looked at her smooth arms and dainty hands. She wasn't built for strength, being a whore the men generally wanted something soft, manipulatable, pretty, and responsive.

She had never really thought about it before, but her body was built for being used sexually, physical attractiveness took priority over physical strength.
But how could she defend herself then? It could take years for her to build up the kind of strength needed to move a full grown man around, but should that mean she was helpless until then?
She shook her head to herself. No, she had to be able to do something the way she is now.
She could use her speed and resourcefulness until she had enough strength to utilize.

Another idea occurred to her and another mischievous glint flashed in her eyes.
"I think I see... but nobody has held me down by my shirt before. Normally they pin my wrists to the ground and take me that way. How does one escape from that?"
 
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Willis frowned remembering the time his mother pinned him to the ground while she beat him up. As painful as that memory was, it was the time that the boy grew a spine and actually defended himself. During her drug induced beatdowns, his mother grabbed the boy by the wrists however he used her momentum and briefly pushed her back. "Wait they forced themselves on you?" Willis asked raising an eyebrow.

He shook his head. "Well in anycase," he said. "When they grab you by the wrists," the young man held one of Eryn's wrist. "You want to use my momentum to keep me off balance. A common misconception amongst people is that they think strength is everything. That's not true. You have other advantages Eryn, looks, speed and deception which are major assets. In your case you just need a little guile."

The young man then smiled holding Eyrn's wrists. "Now try it," he said.
 
She shook her head and chuckled.
"No, they didn't force themselves on me, they just liked being in control."
She let herself be pinned as he climbed on top of her again.
She experimented with trying to move her wrists up or down but she couldn't budge his hold on her.
She squirmed around a bit more trying to understand what he meant about using his momentum, he was simply pinning her down and didn't give her any momentum to work with.

But then she got an idea. His weight was forward to pin down her wrists, so that put less of his weight holding down her hips and torso.
She thrust up on him with her hips, launching the rest of his weight forward while she finally pulled her hands down to her sides.
If he held on to her wrists he would have no balance support and would quickly find his face meeting the ground as his momentum was thrown forward and over her head, and if he let go to catch himself she was practically free!
 
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Willis gave a sigh of relief he's heard multiple tales of drunken patrons forcing themselves on barmaids. He remembered punching the face of a drunken man who tried to kiss an unwilling barmaid in the Gold Road. The waitress had thanked Willis profusely after he knocked him out, thankfully Eryn didn't have such experience but at least she'll be prepared if they did. The young man himself being launched forward but he maintained his balance.

The best part was that Eryn managed to relinquish herself from Willis' grasp making the young man smile. "Good," he said kissing her on the forehead. "As you can see not all self defense requires strength you just need more opportunism mixed in with some pragmatic tactics."
 
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She grinned proudly at his praise but felt cheated when he only kissed her on the forehead. So again she took his advice.
She pulled down on one of his supporting arms at the elbow with all her weight to cause it to buckle and put him off balance, she then pushed up against him with her hips and turned them over, rolling till she was on top and straddling him.

"I'm learning a lot already, thank you babe!"
She giggled at her victory and pushed her lips to his.
 
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Willis found himself flat on his back as they rolled against the grass. The young man locked his eyes against hers as he kissed him on the lips. "My little whore," he chuckled stroking her long red hair. "You are strong as you are beautiful." Willis began to take off Eryn's dress as he continued to kiss her. "You mean a lot to me Eryn," he said. "I will protect you but I'll give you tools to defend yourself in case I can't be there."
 
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Eryn let him pull her blouse open and off her shoulders, but stopped him beyond that. She pulled out of the kiss with her eyes closed and licking her lips, savoring the taste. When she opened her eyes again there was a hungry look in them but she restrained herself.
"There's only so much time in the day, my love. Let's make the most of it and save our lovemaking for bed before we waste away the light."

She kissed him gently once more and put a hand on his chest before he could pull her down again. Her naked bosom lightly rose and fell with her impassioned breathing, but she slowly and reluctantly rose off of him and let him stand up.
 
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Willis was disappointed but understood Eryns rationale. There were times that they were fucking all day and night to where they were too tired to do anything else. “Very well,” he said smiling. “But as soon as night falls you and I will be fucking until we’re too raw between our legs.”

The young man got up and helped Eryn to her feet. “But do you promise to always dress sexy for me my little barmaiden?” Willis winked.
 
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