Tail Sting Ch. 03: First Day

Rhona Staelish paced back and forth in her office as she waited. The Sheriff of Longacre loved her town, but she had fought away a lot of corrupting influences to help these people, especially her niece, Cimri. The Archbaron was not a particularly good person, but he'd burn down any threats to the area he controlled. Collateral she'd have to manage to protect the citizens from. She was a distinguished woman, long dark hair, high cheekbones and a strong jaw.

Rhona knew something was wrong lately. Iomedae's followers were raising their heads again, and that was never a recipe for a peaceful town.

* * *

Reda awoke on her section of lounge again with a squeak. She still wasn't used to this luxury. She noticed Durdyn standing before her with a laden tray of food.

Reda was still caught offguard every time the Drow silently appeared. Evolutionary fear she was working on overcoming.

He offered the tray and she took it, nodding in thanks as Kay climbed down the ladder.

"I'm glad you're comfy. Gotta find your own mark today. Estia has training, and I have to train her," Kay informed Reda as she tucked in to breakfast.

"100 gold is a lot, isn't it?" Reda asked, mentally assessing her rates.

"You can do it. We'll discuss your training when I get back." Kay took her tray from Durdyn and started eating.

"Do I get vestments like yours?"

"No one got vestments like mine, sweets. We can look into getting you some that suit your figure." She glanced back to Reda and added, "you have different features. My vestments are designed to show off my boobs while also lifting them. Fuckers are heavy, but marks love them." Reda loved them too but didn't have a chance to express it much. "Stand up honey."

Reda crawled out of her corner, still wearing the tunic and khaki trousers from the day before. She removed the garments and got down to her bare skin, with Kay standing up and doing examining the Half-Elf in her nude glory.

"Your tattoo is red," Kay remarked but as she looked over Reda, her delicate fingers framing where potential hems of fabric could go, she didn't mention it again.

"Reda, you don't have the breasts for a vestment like mine. Your slender frame could work something else though. We'll go see the tailor later," Kay uttered her assessment, cupping Reda's cheeks with her hands, ensuring Reda was looking in her face. "You are made for this and I wish I had your waistline."

With a positive comment to end on, Kay went back to her breakfast and Reda found the clothes she had just removed were now missing. She looked around again and found Durdyn holding out a clean and folded set of clothes. She donned this set, finding it to be a yellow version of her previous day's outfit.

"Thank you, Durdyn."

The Drow nodded and quietly stepped away.

* * *

Reda wandered through the marketplace before realising she had no idea how to approach a mark. Many of the guys she saw walking around were not well dressed, the rest were wearing wedding rings.

"What am I supposed to look for?" Reda asked no one in particular. She threw herself down on a bench in frustration and angrily looked at the people congregating around the square.

"Citizens of Longacre! This town has fallen into disrepute!" a booming voice declared over the square. A woman wearing blue and white vestments was standing on the balcony of a local church. She preceded to give a sermon on the benefits of the Glorious Reclamation and the will of Iomedae.

* * *

"Put your energy into it. Focus, Estia," Kay encouraged. Estia was kneeling on the paneled floor of her den, her back bare and pale skin radiating in the dim light.

She held the ivory symbol in her hand and tried to channel energy through it. Her ability to Lay on Hands was one thing, but channeling was an advanced skill. Paladins and Anti-Paladins both were capable of learning this skill, the extension of Divine Magic.

A harsh crack echoed through the room as Kay's whip cut into Estia's back.

"Come on, Estia."

She focused again, and after another six seconds, Kay whipped her again.

This continued for hours.

* * *

Reda sat through the entire sermon, and when the Iomedaeans left, the crowd was very dense. A lot of people were gathered and they were touched by whatever message the woman, Allamar, was delivering.

Reda was getting better at reading people, since fleeing her home country. Necessary survival skill.

She saw one very quiet dude in the crowd and nodded to herself. The Half-Elf adopted a confident strut as she approached her mark.

"Hi there," Reda said in an upbeat tone.

"Hi," he responded. He was thin, nervous and slightly dishelved.

"You look like you could use some company," she offered him a hand and he took it. "Sister Reda."

"Toby. Just Toby," he introduced himself and the Lady of Tail Sting lead him to an alley, free from prying eyes.

"Toby, I'm a Callistrian sister. We take patronage in exchange for service," Reda explained.

"How much?" Toby asked nervously.

"I need to make 100 gold a day. But I'll only charge you 30. Deal?"

"Deal." Toby fumbled for a coin pouch and the gold exchanged hands.

"Thanks," the Half-Elf murmured in a seductive tone as she turned and lowered her trousers slowly over her arse and down to her knees, leaning forward to present her cave of wonders to her first customer to pay with coin.

Having never been in this spot before, Toby sported an erection prominent enough to impede his own trouser removal, but he still managed to free his burgeoning manhood. His fingers trailed up her thigh, finding the entrance he'd been longing to find since early puberty.

Reda felt his fingertips trailing around her lower lips but was surprised when his manhood slipped in. He didn't have the same tapered crown every other man she'd been with, he was smooth. He was also bigger than she'd expected, given his frame. Sivaal was around this thickness, and she remembered how incredible that experience was.

Unfortunately for Reda, Toby didn't have the same level of control.

He pounded away, forcing her walls to stretch but it didn't take long before Toby groaned and his manhood pulsed hard and quick inside her.

She whimpered as he withdrew but still turned around with a smile.

"I, uh... Thank you," Toby stammered.

"Keep me in mind for future business, okay?" Reda winked as she pulled her pants back up and walked out of the alley.

Disappointing, but 30 gold is 30 gold.

* * *

Estia could feel it, she'd finally managed to channel through her symbol. Kay had staggered slightly but through her own will, minimized the effect.

"Good." Holding onto her own holy symbol, Kay channeled healing energy. The multitude of cuts on Estia's back sealed up, and the woman exhaled.

"I can't channel positive energy though," Estia lamented but Kay was still soft as she spoke.

"Your code prevents it. You literally can't."

Estia shrugged her shoulders and sighed.

"At least I can do it now."

* * *

Reda's next mark was equally disappointing. A taller man named Sergei, somehow had the same potency as Toby but a lot less to work with. He didn't say much after finishing, just deciding to pull up his pants and leave.

For her third, she decided to try her luck at the Last Stand Tavern. Fortunately for her, men were a lot more eager to approach her at the bar, but most were unwilling to pursue het when she mentioned that she expected financial compensation.

After the fifth man to approach her left upon discovering her rate, a sixth soon took his place. This man looked well dressed and familiar, but Reda couldn't place where she'd seen him.

"Are you looking for some company, my lady?" he offered and she smiled. Although it was little more than a customer service smile at this point, the man's grizzled facial hair and charming smile made her feel a little more comfortable.

* * *

Estia groaned as the manacles binding her wrists prevented her hands from moving. Kay's fingers tweaked her nipples and the redhead exhaled through her nose.

"Come now, Sister. Our Lady expects better than this," Kay taunted the fully restrained Anti-Paladin. Estia's walls clenched hard on the hollow balls inside her while Kay still paced around her.

The elder Sister was wearing Estia's favourite strap on to use with her clients, a little longer than the one she used on Reda and a little thicker.

Estia felt the tip of the strapon skim across her bare buttcheek and she whimpered against the gag in her mouth. The plastic crown pressed against her starfish, probing into her backdoor and pushing her forbidden walls open.

The suspended and bound woman grunted as Kay inserted Estia's favourite toy into her least favourite orifice.

"You did spring this on Reda, I think that means you should like it too." Kay grinned a malicious grin and continued inserting her phallic friend.

* * *

Reda checked the coin sack she was handed and with quick addition realized he'd given her 100 gold.

"That is your daily requirement, yes?" the grizzled man inquired as he freed his erection and Reda nodded. Her trousers were quickly lowered and she was quickly bent over and his manhood slipped into her tunnel. He wasn't very big, but unlike Sergei, he knew how to use what he had.

Reda's arousal grew thicker and her walls tightened around his intruder. Each thrust bringing them both closer to climax. His hips clapped against her buttocks as Reda stifled her moans.

"You like that?" he asked in a cocky voice, successfully taking Reda out of the moment.

"Yes, yes sir," she breathed in response and he clapped his hips on her arse even faster, pulling her back in.

Reda felt her orgasm building again, getting closer and closer. She could feel that she was right on the edge, and then the nobleman completely withdrew his manhood and she was left whimpering for a moment as she felt his semen spurt onto her arse.

"Thank you, Sister." He had redressed and left before the frustrated Half-Elf straightened up again.

* * *

Kay and Estia were both waiting at the chapel as Reda returned, flashing the pair a weak grin.

"Hey, how was your first day?" Estia asked, lying with her head on the seated Kay's lap so that her sore arse could sit without irritation.

"Got a hundred and sixty gold," Reda threw her coin pouches on the lounge before throwing herself down after them.

"That's very good for your first outing," Kay beamed with pride before noticing that Reda still looked depressed. "Something go wrong?"

"Frustrated."

"Why?"

Reda lifted her head to look at Kay and Kay clicked by her facial expression. She didn't show it though, Reda still needed to learn to ask for things.

"I had two dud lays and the third got me to the edge and then spilled on my arse. Sivaal set a good impression of what I thought to expect from customers."

"Yeah, Sivaal is a darling sent by Callistria herself. He fucks like it at least. He does set a high standard," Kay explained. "What are you going to do about it?"

Reda looked around the literal sex dungeon they were sitting in and her eyes settled on the big, locked cabinet.

"Can I-"

"Those are mine to use as head of this church at my own discretion."

Reda kept looking around and noticed Durdyn in the corner, dividing up a meal prepared upstairs into three portions.

"What about Durdyn?"

"The rule with Durdyn is he has to climax," Kay instructed. "He was born into a cruel life and I'm abusing my position as his owner to ensure he gets enjoyment out of life. If you take his pants off, they're not going back on until he's done. Is that understood?"

"Yes, Sister."

Reda's pants were off as she confirmed Kay's rule and she had strode over to the Drow and tapped him on the shoulder. Durdyn turned around and looked the doe eyed girl in the eyes and waited for her to say something.

"Take your pants off and lie down," Reda commanded in Elven. The Drow did as she ordered, leaving the three trays of food, and waiting patiently for Reda to give another command. Reda noticed he wasn't fully erect, but removed her tunic to expose her breasts and hopefully help Durdyn rise to the occasion.

It helped a little, but wrapping her hand most of the way around it and trying to stimulate the nerves along the underside of the shaft and putting the crown in her mouth helped a little more.

Kay took both her and Estia's dinner and the pair began eating as they took in Reda's fellatio skills. They were poor, but luckily for Reda's jaw, Durdyn was conditioned to achieve an erection on mental command.

His considerable manhood now standing at attention, Reda's tight passageway coated in her juices, the Half-Elf climbed up his body while holding the blue phallus.

She used her left hand to spread her labia, and her right to line up the Drow's manhood, his crown forcing its way inside her, pushing the soft walls apart.

Reda groaned with the sensation, forcing her cunt to stretch to accommodate the monster. She didn't think it'd be this difficult this time, but as her descent on his pole almost completely stopped, she realized her eyes were bigger than her vagina this time.

Estia was finding herself horny again, but her orifices hurt too much to pursue action at that moment, and Kay was amused. She'd made a point of fucking the Drow at least once a week, and it still wasn't easy. Not that she had hated it, quite the opposite.

Reda couldn't force any more of Durdyn's cock inside her, less than she had on her first night in Longacre but Durdyn had been the driver that time.

Reda lifted herself slowly and struggled to go back down, and the Drow watched her. The lithe Half-Elf was having trouble riding him but he wouldn't do anything until commanded.

Reda wondered momentarily why she thought that this was a good idea.

"Come on, ride him!" Kay cheered from the sideline. Estia was suddenly curious how much less riding Durdyn would hurt, but she also wanted to try and stay as faithful as she could.

Reda didn't feel encouraged by the peanut gallery, but she didn't have the willpower to keep bouncing on the monster inside her.

"He has to climax." Kay's voice rang in her ears and Reda made a decision.

"Roll me over and pound me," she ordered the Drow in Elven. Before she knew what was happening, she was on her back, looking up at Durdyn as he plunged his manhood into her tight cave. He pushed in twice as far as she'd gone down, eclipsing the size of every other man in Longacre she'd had while still not fully inside her.

Reda gasped as her silken pathway spread for the blue monster, Durdyn's crown pressing firmly against her cervix as he withdrew and plunged his cock in her once more. He wasn't as gentle as he was a few nights prior, and the juices easing his passage in and out were taken as a sign he was doing something right. Reda felt Durdyn reshape her insides to accommodate the rest of his manhood and tears welled up in her eyes. Simultaneously, her drive to come was going into overdrive.

The girl moaned in pleasure as the Drow pounded on her little cunt, and Estia found herself fingering her clitoris while watching them. Kay chucked, leaving a hand on Estia's arse while the girl played with herself. It was finally a show worth watching.

Reda felt her climax build as Durdyn's full length pounded into her, his hips clapping against her butt, the pain of the moment being overwritten with the need to finish.

Kay smiled as a pleased grin crossed the Half-Elf's face, knowing the high Reda was riding. She'd make a high class escort out of her yet.

Estia was proof she could train anyone, even a married woman. She also liked playing with Estia. Estia's curves felt as nice as her own, and she was a good bottom. Kay didn't bottom for her juniour Acolytes, but she was curious about Estia's skills after watching her with Reda. She supposed Estia made a good enough living off the women around Longacre as is, and Kay had a feeling she was looking forward to topping Reda again. The faint aroma of Estia's arousal hit her nose and Kay slipped her fingertips down Estia's arse, teasing the entrance to her protege's neglected orifice.

Reda was full, she couldn't possibly take any more of him, but his manhood reshaped her insides to fit more. Reda glanced down and realized she was barely taking two thirds of him. It hurt in the best way, pushing her closer to orgasm, while forcing her past her limits.

Estia felt herself reaching the same wall Reda was, but Kay's teasing was what stopped her from breaking it. She was aching for Kay to penetrate her, but the elder Sister was holding off.

The message was clear.

"You can come when I let you."

An unspoken promise that Kay held the power, Estia didn't.

Reda moaned in pleasure, the blue monster cock pushing in on each thrust and her orgasm building but still not coming. Every time the pain was starting to fade, Durdyn fit more of his cock in her little cunt. The fresh stretch on each thrust pushing her closer to coming until the joining point of Durdyn's phallus to his hips pressed against her vulva, the full length of him painfully inside of her soaking tunnel.

That was enough to break the wall, her shuddering frame relishing the orgasm that shook her whole body, her soft walls squeezed tight, the lubrication forcing the Drow's cock out of her as she squirted on him.

Reda was shakily drawing breath as Durdyn held his erect and lubricated manhood in his hand.

"He has to climax, Reda," Kay instructed and the grin across Reda's face faded slightly. Mercifully, Kay's fingers slipped inside Estia's corridor of pleasure, pulling Estia closer to finishing but avoiding the G-Spot to tease her protege further.

Reda nodded to Durdyn and her walls were forced apart again. Durdyn's big blue cock fully inside her once more, he withdrew and thrust in with force. A flash of a different pain flashed through her as the monster inside her slammed into her with ferocity. A second climax was quickly building to follow her first, Durdyn enjoying every inch of her tight grip that grasped him from crown to base. His pleasure was building but it trickled slowly. Which was how he was trained, conditioned to be.

Estia watched the juice squirt from the Half-Elf's pussy and felt her own walls shudder, she was almost horny enough to push Reda aside and take the monster again herself but she knew better. Her sore cervix was testament to the bad idea. Her husband was definitely getting laid tonight.

Reda's eyes practically boggled from her head, each full thrust of Durdyn's manhood pushing her second climax closer, the pounding hurt less and the pleasure spiked in intense waves, pushing her again to the wall of orgasm but this time it broke easier, her walls clenching around him again repeatedly, but Durdyn caught his phallus as Reda squeezed him out again and plunged it back in, the Half-Elf's cunt offering less resistance than before as his monster ploughed into her and he slammed it in with a passion.

Estia could feel her pulse in her pussy at this point. She was hurting for sex, her fingers snaking towards her entrance but Kay caught her wrist.

"In my chapel, you come when I say so," Kay whispered with venom. Estia shuddered again, Kay's dominance adding to the lubrication coating the inner walls she was praying to be touched.

Kay had quickly moved to salvage her tray of food before standing and taking a set of manacles from a hiding spot behind a cushion on the lounge. Before Estia could think of tending to her own needs again, Kay cuffed her hands behind her back.

Estia's face flushed and she bit back on a quip, but Kay still cuffed her feet together and sat herself between Estia's thighs. She returned to the slight ministrations that were driving Estia insane as she still was prevented from climax.