1 When Getting Isekai'd Goes Wrong

Annie gritted her teeth and gripped the edge of the mattress as her body was rocked forward again. She felt him bottom out, her cunt stretching to accommodate the bulbous head and thick, rock hard length of his shaft. She barely made to catch a quick gasp of air before he pulled back and slammed into her once more causing her to grunt out loudly. She lost her handhold, spilling forward, her large breasts squishing under her as she moaned through another body shaking shove from the fat brute behind her.

"Shit, you're tight, pinky!" The smelly sailor barked, making her unintentionally blush. His heavy calloused hands gripped her short blue skirt that was pushed up around her waist tightly. Using it as makeshift handles he yanked her back forcefully impaling the teenage whore once again on his massive cock. A stifled squeak escaped her lips as her pussy met and gripped the base of his length.

Annie pushed herself back to all fours and her head shook back and forth in time with his thrusting, grunting in her throat with each pump. She could feel his sweaty belly banging against her ass with each powerful thrust while below her, his large hairy balls swung forward, smacking against her engorged clit as he continued his aggressive fucking.

"Shit, this pussy's tight. Didn't think this tavern had wenches this good!" He grunted, sliding one hand up to grip her shoulder using the leverage to brutally ram his dick into her again.

'With how hard that bitch is working us, we better get some recognition!' Annie thought with a scowl. The woman who ran this tavern was a hard ass when it came to her doing her part to draw in customers. Nice as she was off the clock, when it was go time Annie had to force herself not too punch the bitch out of pure frustration.

As for the sailor, he was in heaven. He looked down at the pink haired girl as she squirmed in his grasp, tightened his hands on her slender waist and continued to slam her back and forth, rutting into her as hard as he could. He watched her ass bounce and shake with every thrust. Her fair skin had become flushed, taking on a red hue as he worked his meaty shaft over and over in her tight hole. A sheen of sweat was already quickly building on her skin, giving her a wonderful glow in the dim lamp light that made him want to fuck her even harder.

'I'm so lucky to have caught this bitch before rush hour.' He thought as his belly slapped loudly against her bouncing ass. His eyes rolled shut as her pussy suddenly tightened vice-like around his dick. This place had to be his favorite drinking hole. There were few places cheap enough to let him fuck a teenage girl like this. The younger girls were always the tightest.

The only sounds that filled the bedroom were the steady slap of the man's hips slamming into her ass in addition to her breathy pants and his grunts of exertion. Annie felt her arms start to get tired and decided to finish things off for the night. She tightened her pussy even more on his thrusting shaft, increasing the friction and causing the fat sailor to curse. Behind her she felt him finally tense up and his fingers dig painfully into her small waist as he crammed himself as far as he could possibly go into her pulsating pussy. Annie winced as the overweight sailor cried out in ecstasy, his balls emptying his seed into her. Annie's muscles instinctively clamped down, her cunt, so well-trained, squeezed and undulated, milking his shaft of the warm deposit of slime pumping into her tender pussy.

The fat man fell forward onto her, and Annie let out a muffled moan of protest as her aching muscles supported the ponderous weight of his sweaty body as it settled on her back. He wrapped a strong arm around her waist and kept pumping his hips with small, but powerful, thrusts. His other hand gripped her left breast, kneading it with his fat, calloused fingers.

"If I ever come back here, I'm gonna order you again, girl." He whispered breathlessly.

Annie rolled her eyes. What did he expect her to say? Thanks for the compliment? After a minute he finally lifted himself off of her and shuffled backwards causing her pussy to spasm as his dick popped free with an embarrassingly loud sucking sound.

Annie allowed herself to slump onto the bed, taking the time to catch her breath as fatty left the room. Cum leaked from her spread cunt to pool onto the sheets, which Annie was just going to have to clean now. At least the fat bastard left her a hefty tip.

'I wonder what my parents would think if they knew their little girl was a sex worker in another world.' Annie thought, rolling onto her back to stare at the ceiling.

A wave of melancholy washed over her before she quickly stamped it out and weakly sat up to get her dress. She had no time to get weepy again, there was work to do! Sliding the low cut dress over her head and slipping into the short skirt and boots the innkeeper forced her to wear, Annie brushed her hair back and left the room to get back to serving customers.

Just another day for a teenage whore in another world.

XXXXXX

Annie Koyama was a Japanese-American girl born and raised in Tokyo, Japan. She was a slender girl with pretty features, sporting green eyes and (naturally) pink hair that she'd inherited from her father of all things. She liked sports, though she could hardly be called athletic, and liked to spend time with her friends, reading manga, playing video games. Normal, everyday teenage girl things.

Up until last year, Annie was just an ordinary girl living her life and not caring about anything too serious. But that normalcy went out the window one fateful day when there was a traffic accident and Annie was hit by an out of control truck that ran a red light.

What happened next was a blank for Annie, but the next minute she found herself waking up in the middle of an endless white void. The only sound she could hear was her own heavy breathing as she tried to remain calm in this alien space.

"Where the hell am I?" Annie whispered, holding a hand to her head. "What's going on?"

"You're dead."

Annie jumped and turned to the speaker. It was a little girl, no older than seven if appearances were to go by, but she was clearly no normal girl. Her skin was white as a sheet, as was her long ankle-length hair, and her eyes were pitch black like the night sky. The girl smiled up at Annie with an unnaturally wide smile.

"Who the hell are you?" Annie asked, scared. "W-Where did you come from?"

"I'm a goddess, and you are in my domain. You can just call me Sheba." The girl said, her smile not going away.

"S-Sheba?" Annie repeated shakily. "Wait, did you just say I'm dead?!"

"That's right. You died as soon as that truck hit you. Luckily it was painless, so you went without a fuss." Sheba revealed. "I'll let you process that for a moment." Sheba was quiet for about two minutes before she continued talking. "Got it out of your system? Good. Now let's get down to business."

"But—"

"Do you know what isekai is?"

Annie looked at her confused at the random question. "Um…yes?"

"Great, then think of this as one of those me-forsaken isekai anime you mortals love to make so much. Since you died so early in your life, I'll give you a second chance in a new world. A world with magic, nonhuman races, adventurers and all that good stuff." Sheba said. "Now I don't do this for everybody, only people who've been dealt a really bad hand in life."

Annie struggled to process this. A world where magic and adventure were prevalent, just like the anime and light novels she read. The idea of a second chance in a newer, more exciting world sounded appealing after getting abruptly killed like that. Sheba's smile grew wider upon seeing that she had the girl's consent, not that she really needed it, but it made the process go smoother.

"The world I'm placing you in is called Aurora, and it's filled with all that good stuff you usually see in your average JRPG. Plenty of stuff to do, but only a few paths are open to you. I'm going to implant the basic information of this world into your mind, but once you're on the ground you're on your own." Sheba told her. "Oh, and you'd best find some work at a tavern or something. Money doesn't grow on trees you know."

"O-Okay." Annie nodded.

"Sweet! Have fun in the new world, Annie Koyama! I know I will." Sheba snapped her fingers and Annie vanished in the blink of an eye, her soul transported to one of the main worlds the goddess watched over. Sheba giggled at her own deviousness and clapped her hands.

"That girl is so fucked."

XXXXXX

This led to Annie being dropped off into this new world with nothing but the clothes on her back. Sheba was telling the truth when she said this world had the typical fantasy tropes of magic, monsters and different races from humans. It was honestly an amazing experience for Annie, but the novelty of her surroundings quickly wore off as soon as reality started to set in.

The city she was dropped into was called Ishtar. It was a popular city known for its abundance of adventurer guilds and various trading posts that sold tons of goods. Annie was a stranger in a strange land, and with no money or a place to stay, as soon as night fell, she was forced to seek out shelter lest she freeze to death on her first night in this not so cool isekai adventure.

Going off her wide knowledge of JRPGs and fantasy tropes in general, Annie knew that there had to be a tavern that she could stay in for the time being. It was just her luck that she found one that was run by a stout but busty redhead named Katherine who just happened to be looking for a serving girl to help with the customers. Annie was pretty much hired on the spot, her pink hair considered an exotic attraction to draw in new customers.

Forced into a wench's dress that felt like skimpy cosplay, Annie spent the first few days in this new world as a tavern wench, serving customers and waiting around to look pretty, hanging off the big, strong arms of warriors and soldiers as they drank and ate their hearts away. It was a bit damaging to her self-respect, but she could handle it. But then there was another aspect of her job that she didn't expect.

Sex.

Tavern wenches were commonly paid for their services in Ishtar, and Annie was no different. Despite her age, Katherine had no qualms about advertising her new "exotic" girl and whoring Annie out. As a result, Annie spent her Wednesday night losing her virginity to some boorish grunt who got lucky enough to get her pussy first. After that, Annie became very familiar with sex as men wanted to try her out day in and day out. Katherine was nice enough to let her have breaks between shifts, but it didn't stop her revulsion from having a man cum inside her without protection (condoms weren't a thing in this world, so either a man pulled out before cumming or let it all loose in inside her, which was the case every time).

The sex disturbed Annie at first, but she knew that this was a fact of life in this medieval fantasy world. It was a bit odd at how fast she got used to it, but at this point Annie could hardly muster up the strength to care. This was her new life now, as some teenage whore in a tavern with a forgettable name.

But a week after she first arrived in Aurora, things changed drastically for her once again.

XXXXXX

It was a typical Sunday morning and Annie was already washed and dressed as she trudged downstairs while tying her pink hair into a ponytail. She was still a bit sore from the last client she had last night, but if Katherine was in a good mood, then perhaps she wouldn't have to take too many customers this time.

"Morning Katherine." Annie yawned as she reached the bar. "Got anything new for me to do to…day…"

Annie finally registered that the tavern was completely empty. Even on slow mornings there were usually at least three people here for breakfast. But today the place was completely devoid of customers and that immediately put Annie on edge.

That was when she noticed the two people by the front table.

She recognized Katherine's stout but curvaceous body, the middle aged woman with short brown hair and gray eyes clad in a form fitting and revealing dress to display the curves that she had yet to lose. The usually confident looking woman actually looked afraid, which was a first for Annie. Though looking at her companion, Annie could understand why.

The other person talking to Katherine was a woman of exceptional beauty. She was a mature looking woman with black hair tied back in a perfect bun and enchanting hazel brown eyes. She wore an expensive looking tight black dress that highlighted her curves and exposed the top of her cleavage tastefully, exposing just enough to make one curious. One curious feature the woman had was the black lipstick mark on the right side of her throat, marring her flawless pale skin like a hickey.

"So this is the girl you've managed to hide from us." The woman said calmly, looking at Annie with what could be mistaken as a lustful gaze were it not for how intense it was.

"Y-Yes, that's her." Katherine stammered. "Introduce yourself girl."

"Uh…hello there, ma'am." Annie said politely, bowing her head. Was this woman a noble of some kind? "I'm Annie Koyama."

"I love your hair." The woman complimented. "It's natural, yes?"

"Yes ma'am."

"And you've been working here for how long?"

"About a week. I just moved here from the countryside looking for work." Annie said. It was a little white lie, considering she had nowhere else to go.

The woman nodded and turned her gaze to the still frozen Katherine. "And this woman here has been whoring you out to customers, yes?"

Annie blushed and looked at her feet. "Yes ma'am." She answered. There was no way she was lying to this woman. "I've lost my virginity servicing customers here."

"A shame you had to do that considering you could have put your talents into someplace less vulgar." The woman stood up and walked over to Annie, her heels making a sound on the wooden floor. "Annie, my name is Veratos, assistant manager of the Black Widow. Madam Gawain has heard of you and would like to interview you for a job at our establishment."

Annie stared at Veratos for a long time, unable to believe what she just heard. Katherine had mentioned the Black Widow in passing, mainly whenever she was complaining about her dwindling customer base. It was a very popular brothel run by a woman named Gawain, who ruled the entirety of Ishtar's sex industry, from the dancing clubs and massage parlors to the brothels and upper class meeting spots.

"Y-You want to speak with me?" Annie asked. Veratos nodded.

"Yes, we would like you to come with us. Today would be preferable, but I understand if you need some time to think about it—"

"I'll pack my things!" Annie was already back up the stairs before Veratos even finished her sentence.

"Wha—Annie?!" Katherine exclaimed. Veratos smirked at her.

"It seems that girl wants something more than being fucked by lower class trash every night." She said. "I don't blame her. A sub-par tavern attracts sub-par men."

XXXXXX

The Black Widow was located in the heart of Ishtar's red light district, surrounded by dancing clubs, massage parlors and even an adventurer's guild. The building was a large establishment, with a rowdy tavern on the first floor and numerous rooms on the three upper levels. Annie heard plenty of stories about it from the many customers who visited the tavern while she worked, but seeing it was something else.

Annie would have liked to choose a job that didn't involve her being a whore, but there weren't that many options. She learned quickly that this not so amazing fantasy world was incredibly sexist and misogynistic, where women couldn't even walk by themselves without being accompanied by a man! Hence the strange looks she and Veratos garnered as they walked through the streets towards the brothel.

Veratos led Annie into the building and Annie was assaulted by the smells of the place. The lobby smelled faintly of smoke and liquor, with slight undertones of sex and sweat. The tavern was full of men, big, burly and rowdy. A large stage was erected on the far side of the room, and a dozen girls paraded about, calling out to patrons and trying to entice customers. There was an empty desk right next to the stairs where she assumed Veratos usually worked.

"Come along," Veratos said as she went to the stairs. "Best not to dally. The mistress does not like to be kept waiting."

Annie quickly followed her upstairs to the other floors. They walked through the long hallways with rooms lining both sides, loud moans and the distinct sound of skin slapping skin could be heard from some, excited cries and climaxes from others. Women being used. Annie felt her cheeks turn red and she tried to ignore the sounds as she followed close behind Veratos as they reached the madam's office.

As they reached the door at the end of the hall, Veratos knocked on it twice and said, "Madam, you have a visitor."

"Come in." Came the faint reply.

Veratos opened the door and ushered Annie inside. She stepped into the room, but Veratos made no move to enter. The door closed behind Annie, letting her look around.

The office was surprisingly well-decorated, with the walls painted a bright red with golden flowers scattered across it. The carpet was also a deep crimson, but sported black flower patterns along its length. There was a bookcase on the far side of the room, and a fireplace located next to the large mahogany desk. What a surprisingly fancy and lavish place for the office of a brothel mistress.

"Expecting something less clean and pretty? You aren't the first to be surprised at how tidy I keep my work place." A cool but honeyed voice purred from behind her.

Annie's breath hitched in her chest and she almost jumped, but caught herself, spinning around to face the woman. Once again she was met with the cool visage of a beautiful woman who looked far too regal to be anywhere near a brothel. She had long golden blonde hair that fell down her back and stopped at the middle of her back. Her face was slender, her skin fair and clean, her icy blue eyes contrasting her full red lips which were turned up in a smile. She wore a lavish black and dress that displayed the cleavage of her large breasts and flaunted her curvaceous form.

"Welcome to the Black Widow. My name is Gawain, the owner of this fine establishment, and overlord of pretty much every single den of sin in this part of Ishtar." She began, smiling sensually at the girl. Annie felt her eyes on her as Gawain walked around her, eying her like a piece of meat before leaning against her desk to give the pink haired girl her full attention.

"H-Hello," Annie said, remembering her manners. "My name is Annie. Veratos said that you wanted to see me?"

"Yes, I did. It was mainly because I wanted to see the young girl with the oddly colored hair that some of my clients praise so much. The girl with the slender curves and tight cunt." Gawain smirked at Annie's blush. "It's too late to be getting embarrassed this late into the game, my dear. You're still new, but you've been with enough men to hear worse."

She was right about that. Annie has heard worse from the men who've fucked her in the past week.

"Looking at you now, I see a girl with nowhere else to go and clearly out of her element. You've been forced into selling yourself for money at the behest of a woman who's nearing the end of her prime. It'd be a waste for you to spend your early years as a mindless tavern wench when you could be making more money under someone who knows how to do business."

Gawain ran her eyes over Annie's form, taking in her appearance. Annie was currently wearing her school uniform, a tight button up shirt and a short blue plaid skirt with black socks and shoes. It was all she had on her when she came to this world, though she hid it away when she began working at the tavern. It was a bit more revealing than what women normally wore, so it probably was the reason Katherine decided to whore her out.

"So here's my offer. Join the Black Widow as one of my girls and you will not only get paid, but you will also be given free room and meals every day for as long as you work here. Unlike those moronic men who couldn't run a shack let alone a sex ring, I treat my girls nice. Anyone who fucks with my girls don't live long to brag about it, that I promise you." Gawain said. "And you will also be able experience the best pleasure a woman can have in this line of work."

Seeing that Annie wasn't entirely convinced, Gawain hummed and tapped her chin with a manicured finger.

"You're still a bit wary. I can understand that. Any girl would be cautious when dealing with the sex trade business." Gawain nodded sagely. "Let me help you understand what kind of business I run around here."

Gawain's aloof expression hardened and Annie inhaled sharply at her sudden change in demeanor. "I run the biggest sex empire on this side of the continent. Every brothel, every dancing club, every massage parlor you see in this city, and beyond is under my command. I take my work seriously compared to those boorish moronic cavemen who beat the women making them money or the jaded old hags stuck in some old fashioned traditionalist mindset. My girls are clean, drug-free, and well-cared for in return for top notch service and work ethic. I don't take dirty, disease ridden skanks who put the bare minimum of effort into getting clients. This is a business, you girls are my merchandise, and I take care of my merchandise."

Her blunt words were surprising to Annie, who expected the woman to veil her profession with honeyed words and paint the job as something else entirely. Gawain was just that confident in her empire that she was not afraid of telling the truth, no matter what Annie thought.

"This brothel of mine is my castle, where I made my rise to power. Here my girls do their best to please their clients to the best of their abilities, and also know how to play well with each other. There's nothing wrong with some friendly competition, but infighting will result in some disciplinary action." Gawain's eyes turned even colder at that. "Whether you get clients to see you or not is up to your performance. Don't blame it on the whore you have beef with."

Gawain took a step closer to Annie. "I have my enemies and detractors who think they can make me bow just because I am a woman. I'm still here, they are not. Work with me, and you will be under my protection. No one will fuck with you or they will answer to me." She stared the pink haired girl in the eyes. "So…what do you say?"

Annie's heart was beating a mile a minute. She had just spent her first week in this world being whored out to ugly brutes and overworked miners, and now she was trading one sex job for another, albeit one with more glamor and better pay. Had she been given this offer when she first came to this world, she would have said no and ran the hell out of there. But she understood that she wouldn't last long by herself with no money and no home. She had to do what she must to survive, even if was a blow to her pride.

"I…accept." She said hesitantly.

Gawain stared at her with an unreadable expression before smiling. "Good girl. I'm eager to see if your confidence holds up in the future." She moved her head closer to Annie, so close that the girl could smell the sweet wine on her breath. "But first…"

Before Annie could react, Gawain's head shot down and her lips pressed themselves against her neck. Annie gasped and shuddered as an electrical surge of pleasure assaulted her from head to toe. Gawain's red lips suckled on her throat, her lipstick creaking a lip-shaped mark on Annie's skin. The pleasure was so great that Annie sagged bonelessly against the door while Gawain sucked on her neck, moaning and whimpering.

After a few minutes Gawain finally pulled back, a smile on her still vibrant red lips as she studied the panting girl in front of her. At the base of her throat was a red lipstick mark shaped exactly like Gawain's full lips, visible against her pale skin.

"That was a little something that I give all my girls when they join here. It's a magic sigil I designed to not only act as a contraceptive for you, but also alert me if you are in any trouble. Sometimes my girls run into some unruly customers who need to be disciplined and that mark immediately alerts me if you are in danger." Gawain explained to her. "No one fucks with my money makers and live to brag about it."

Annie could barely process what she was saying as she was too busy recovering from her mini-orgasm. It was unlike anything she had experienced before. Gawain laughed and helped the girl away from the door.

"Take some time to recover and then we can find you a room to start. Before I put you on the market, I want to see how well you can do in bed. Break you in, if you will." She said, rubbing Annie's shoulders. "One of our regulars will be having you tonight, a man who knows how to deal with first time whores. He's nice and he'll take it slow, though I should warn you about something."

"W-What?" Annie asked, her neck tingling.

"Most of the clientele who come here are adventurers, and they're known for being larger than the average male. Once you get your first taste of adventurer cock, you'll never want to go back to a regular man again."

XXXXXX

A few minutes later, Annie found herself sitting on the bed in one of the empty rooms on the second floor. Veratos had informed her that her customer would be with her shortly, so she didn't have time to prepare or anything, not that she needed to. She was just wearing her bra and panties, having tossed her shirt and skirt to the side so they weren't damaged.

The room was large, most likely to accommodate the enormous bed that took up most of its space. There was a dresser with a large mirror above it, probably filled with clothes for the girls. The décor of the room wasn't outrageous or loud, but subtle, sensual even in the motif it was trying to convey.

Veratos had told her the rooms were soundproof for privacy, though if Annie listened really closely, she could hear the faint moans of the other girls on the floor and the distinct creaking of beds hitting the wall. The idea of what everyone else was doing made her blush though she felt a familiar heat in her loins that made her rub her thighs together. Very soon she was going to be one of those girls.

Annie took a look at herself in the mirror above the dresser. Her pale skin was flush and her throat still tingled from where Gawain had kissed her. A black lipstick print was visible against her skin like a brand and it cemented just how deep Annie had gotten herself into this already. This was hardly the life she imagined herself growing up back in her family's estate, but she had to do what she must to survive, and maybe return from her fall from grace in the future if it were possible.

A knock on the door shook her from her thoughts and Annie stood up from the bed, hands clasped in front of her. Veratos opened the door and smiled at her.

"Your customer is here, Annie." She said. "Please make sure he's taken care of."

"Y-Yes, ma'am!" Annie stammered.

Veratos stepped back and another person entered the room. Annie's heart sank when she saw that the man was probably about as old as her father, if not older judging from his half-bald head. He looked heavyset but not too fat, a thin mustache on his upper lip that curled upwards at the ends. He wore expensive looking clothes that clearly displayed his status as a wealthy man.

"Oh wow, this is the girl Vera's giving me?" The man grinned, his lustful eyes running up and down Annie's body. "I'm impressed that there are still tavern wenches who look this attractive anymore!"

Annie swallowed hard and bowed her head. "T-Thank you for choosing me, sir."

"I didn't choose you, girl. I just like breaking in the new girls whenever I have the chance." He replied with a lewd grin, his eyes never leaving the girl's exposed cleavage.

He walked over to Annie and promptly sat down on the bed, pulling Annie into his lap, and from there things began to move so quickly that Annie had a hard time keeping up. When he leaned in, Annie steeled herself and closed her eyes, trying to block the image of the perverted expression staring back at her.

'Just kiss him and get it over with. You signed up for this, you stupid girl.' Annie told herself. His sloppy lips touched and dominated Annie's and soon she realized just how out of depth she was in this situation.

His slobbering lips dominated Annie's as his tongue invaded her mouth, stealing her breath away. As his lustful muscle swirled about her mouth, forcing her to taste the flavor of this half-bald old man, he slipped one of his hands up her skirt, peeling away her panties and began to stimulate her untouched clit. This sent waves of pleasure rippling up from her nether regions, weakening her resolve as she felt her pussy moisten at his touch against her wishes.

'I'm really doing this.' She thought as she cracked open her eyes to see the gross man slide his tongue around her mouth. Annie was still caught in the throes of pleasure as he continued to flick her clit, causing her juices to leak out over his legs. 'I'm really kissing some man I literally just met!'

Then without warning, her partner stopped kissing Annie, but didn't stay apart from her for long as he moved his mouth to her neck and began kissing and licking her flesh. Annie moaned and squirming on his lap, tilting her head to the side to allow him more access as he slobbered all over her throat, coating her neck in saliva. He pressed his lips against the hollow of her throat and sucked hard, making her gasp. Annie began to pant, feeling her body heat up more and more.

Eventually he stopped and pulled away from her, leaving a strand of drool connecting his lips to her throat. "You taste good." He grinned. "Young girls like you are always the best to have."

Annie didn't even want to think about how many other girls he's done this to.

The man gently pushed Annie off his lap and began undressing. Watching him reveal his chubby body wasn't appealing to her, so she looked away, but once she heard his pants drop to the floor, Annie glanced back out of curiosity and as her eyes gravitated towards his crotch, she was shocked by what she saw.

At this point in her new career as a whore, Annie was no stranger to seeing cocks, since she was forced to suck them back at the tavern before they were shoved into her cunt without warning. But she wasn't prepared for the monster her customer had just revealed to her. It was about nine inches long, and girthy too. It was standing fully erect, and pulse with life—a complete contrast to its corpulent owner.

"Since you're new to this, I'll go slowly for you." He said as if he were doing her a favor. "Now get on your knees."

Absentmindedly, Annie obeyed him, lowering herself to kneel on the carpet floor. At this point, she was just going on instinct, the female obeying the male in a time of lust. She swallowed, looking up as he moved forward and placed his cock directly above her face, lightly slapping her with it. It had a manly stench emanating from it, entering her nostrils and fogging up her vision. Staring up at it up close, she was mesmerized by the thick, throbbing veins which creeped along the rod like vines. She raised her hands and began to touch it.

"Stroke it with your hands, girl." He whispered. "Get a feel for it."

As she reached for the meaty schlong, she grasped it with both hands, and found that she was unable to fully close her fingers around its girth. Slowly, she began stroking it in an up and down fashion, increasing in speed as she had gotten used to the motions.

"Use your mouth this time as well. Lick it, slobber over it, suck it."

Annie heard his coaching through her hormone influenced mind, and did as he instructed. She began licking the underside of the shaft, lubricating it and easing her stroking movements. Her spit allowed her delicate fingers to glide over the phallus with ease, increasing her pace as she did so. Then she inserted it into her mouth. It was a tight fit, especially as she began circling her tongue around its head. She pushed it further inside her mouth, savoring its salty taste.

She sucked on his dick with fervor, all while stroking his cock at the same time. He groaned in pleasure as Annie began fondling his balls as well. She did this as she upped the rhythm of her sucking, surprisingly taking it near the back of her throat in spite of its large size. Annie directed her gaze up to him from her kneeling position as she blew his fat cock.

'By the gods,' He blissfully thought. 'She's a natural slut.'

"Ngh, shit, I'm cumming." He growled, pulling Annie's head in for one last throat-stretching thrust, emptying his seed into her mouth. With his scrotum smacking her chin, his large cock speared its way down her throat. Warm jizz fired from his urethra, dumping a torrent of semen down to her stomach.

Caught by surprise, Annie began swallowing the thick mix to help it flow down her throat. As her client pulled his semen coated phallus out of her mouth, its bitterness left an aftertaste in her mouth. Sweat dripped down her face from the intense facefuck that just occurred, and she couldn't help but feel aroused by the whole endeavor. Her overloaded senses made her very, very wet, leaving a small dark stain on the beige carpeted floor.

"You were great, girl! Took that face-fucking like a champ." He grinned, wiping sweat off his forehead.

"Thank you." Annie said, panting a bit. She could still taste the salty, creamy tang of his cum on her tongue and feeling that slime ooze down her throat made her a bit hot and bothered.

"Now we can get to the fun part." He said, leading her to the bed. "Get on your hands and knees this time, and face away from me."

Annie did as she was instructed, giving him a nice view of her perky ass under her short skirt. Smirking, he began fondling her asscheeks, aggressively massaging them with his strong, fat fingers. Annie moaned as he pressed his digits into her backside, rubbing and caressing it with utmost devotion. She yelped when he suddenly stuck his fingers into her dripping snatch, fingering her wet pussy. She mewled into the pillow as he continued gyrating his fingers inside her pussy, before taking them out for her to see.

"You dirty little slut," He said grinning. "Look how wet you are."

By this time, Annie was already red-faced and aching with desire. She wanted him to put it in her. She wanted his cock. She absolutely needed it.

Her customer noted her slutty desperation and decided to get to it, feeling particularly horny himself. He positioned himself behind her and angled his cock at her entrance, then he speared it through. Annie groaned in a bit of pain, though she felt strangely satisfied with the sudden penetration. He was large for her tight pussy, and she felt a bit full, but she gritted her teeth and pulled through.

Then he violently shoved the remaining inches of his cock up her pussy. The sudden thrusting caused her to cry out in pain once more—this time with a bit of pleasure. The large phallus shot straight up to her cervix, jolting her hard enough to see stars. He plunged it into her tight snatch, going almost balls deep inside her. It knocked hard on her womb, itself aching with the need for a good breeding. Her eyes rolled up in sheer ecstasy.

"Congratulations, bitch. You're not a virgin anymore!" He hollered.

"Mmm…" Annie mewled as she took delight in her hole being filled. Normally she would have been somewhat affected by this statement, but at the moment her brain was filled with nothing but thoughts about one, single word.

"Cock," She moaned out. "Your cock feels so big inside me."

He snickered and began thrusting his fat man-meat in and out of Annie, who was now feeling the full pleasure that sex gave. His rough motions in doggystyle gave off sharp noises, which resulted in the girl's ass continually clapping against the man's crotch. In a fit of animalistic rutting, he increased his tempo and started fucking Annie at a faster pace, earning short, quick moans from the girl in question.

Through her lust addled mind, Annie could faintly hear the faint sound of his cock clapping and slapping against her soaking wet snatch, lewd, wet schlicks repeatedly reverberating throughout the room. Was this what she was good for? Allowing older, more privileged men use her as a cocksleeve to empty their balls in? Her thoughts were cut short when her client angled his thrusts differently and then started to batter her g-spot with mind-numbing accuracy. Her head shot up with a scream as she experienced her first orgasm.

He continued hammering the poor girl, completely dominating her throughout the intercourse. His dick flew in and out of the whore, who was reduced to a moaning wreck. The sound of moist flesh slapping against each other echoed throughout the room, accompanied by the pleasurable groans of the two in coitus. The intense doggystyle rocked her breasts, her ample tits swinging under her lean torso.

Annie let go of whatever inhibitions she had, at least for the moment, and just let herself enjoy these sensations. Pleasure overloaded her senses, making her whole body tremble. Her pussy dripped with fluids, lubricating the fat cock of this fat, overweight man. His rough and thorough fucking completely destroyed her previously untouched cunt, giving her levels of euphoria she had never felt before. Her asscheeks were fever red from the brutalizing of her cunt by his length phallus. Once again, she felt a creeping feeling coming up, and soon she felt her second orgasm of the day from the primal pounding.

"FUCK!" Annie shrieked as she came. Clear fluid squirted out from her abused hole, wetting the bed. Her teeth clenched and her toes curled as she rode out her massive release. Her pussy gushed as she saw white, her mind temporarily numb from the steamy intercourse.

The savage doggystyle further intensified as her client felt himself approach his orgasm. In one swift stroke, he speared Annie 's hole once more, letting it take his whole cock. He gripped her hips and pulled her in, hilting the entirety of his cock like an animal would its mate. As he bottomed out inside her, he groaned in his own deep, thunderous orgasm. He erupted inside her, blasting her insides with ungodly blasts of spunk, washing through her so violently that her womb was filled within seconds of his first three loads. His heavy balls contracted as he released rope after rope of semen. After nearly a minute of cumming, he pulled his meat out of Mina's reddened snatch. A dense glob of jizz oozed through her gaping hole and poured out onto the sheets.

Annie slowly sunk herself down onto the bed, panting heavily from the sexual congress that just occurred. She trembled a bit, feeling tingly from her overstimulated nerves. The rough fucking that would normally be too much for a virgin was exceptionally received by Annie, proving the man's hypothesis was correct; this girl was indeed a natural-born slut. As she rolled herself over on the bed, she caught another glimpse of his member. Her eyes widened as she realized that his long shaft was still standing erect, his hefty ballsack hanging underneath it.

"We're not yet, little girl. It's not over until my balls are empty."

The night was still young after all.

XXXXXX

Madam Gawain watched Annie's induction into the Black Widow through her crystal ball with a smile on her face. Another girl added to her family, and another whole to make her money.

She glanced at the statue of a naked, statuesque woman sitting in a shrine. The vision she received from her goddess had confused her at first, but now she understood what her beloved goddess wanted to show her. A girl from another world ripe for the taking, read to be molded by her hands.

Gawain made a reminder to offer Sheba more sacrifices when she had the chance. This otherworlder was going to make her so much fucking money.