Isekai Sex Workers

Chapter 1-A Day in the Life

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.

"Damn, that's a tight pussy. Are all you Rose girls this tight?" He asked rhetorically, sliding one hand up to grip her shoulder using the leverage to brutally ram his dick into her again.

'If you had the money to come here more often, you'd know that yes, we are this tight every night, fatty.' Annie thought, but she kept her true feelings in. The mistress said to be nice to the customers until they start getting rowdy, so that's what she had to do. That, and this fat bastard's cock actually felt really good.

All in all, it was a decent way to end off a pretty slow night. She was still the new girl, so she didn't really have first pick of clients like her older coworkers, but tonight was an abysmal night for her. Many of the men visiting the brothel went straight for the more curvaceous girls, leaving her to deal with the dregs who scrounged up enough money to buy her for one session. Hell, even May was getting more action than her, and that rankled Annie's nerves despite not really enjoying her work.

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. He was so glad he chose the teenage girl for what was probably going to be his only visit at the Black Widow. The younger girls always felt 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.

Annie missed her old world. She missed going to high school, she missed modern food and conveniences and she missed her family. All she had was her BFF and the clothes on her back. But until she found a way to return home, she'd have to use this job as a way to survive.

Just another day for a teenage whore in a fantasy world.


Annie Koyama was a Japanese-American girl born and raised in Tokyo, Japan. She was a slender girl, well-proportioned with above average features, with green eyes and (naturally) pink hair that she inherited from her father of all things. Though she stood out amongst her peers, Annie was a relatively normal girl who went to school, hung out with friends, and spent her days reading manga or playing games.

The only long-lasting friend she had was Megan Lee, another oddly colored haired girl whom Annie grew up with. Unlike Annie, Megan was more of a book lover and closet otaku who had dreams of bright and vibrant fantasy worlds and shonen protagonists. A nerd through and through, and Annie loved her for it.

Up until last year, Annie and Megan were just two ordinary teenage girls doing whatever it is girls like them do in their lives. Then that normalcy went right out the window one fateful day when Annie tried to push Megan out of the way of a truck that was running a red light. The girls didn't know what happened next, only that they were suddenly in a white void, with some mysterious little girl with a creepy voice standing before them saying that they died.

They died.

Annie could hardly believe it. She didn't want to believe it. But seeing this little girl in a white dress explain that she was a goddess was something she couldn't play off as a joke when she basically listed off her and Megan's deepest, darkest secrets. The kind of shit that absolutely no one but themselves knew about.

What followed next was something that came right out of an isekai anime; they were being sent to a new world, one of magic and fantastical creatures. Annie and Megan were enchanted by the idea of having their own grand adventure, something to take away the sting of never being able to see their home or families ever again.

Instead, what they got was being dumped into a new world with no money, no super awesome magical powers that the standard isekai protagonist would have, and only the clothes on the backs as they were tossed into a world that was, unfortunately for them, very misogynistic. What's worse, the place where they landed was right in an alley behind a brothel, and by luck they were scouted by the brothel's madam, Gawain.

And so, with no money and no home to go back to, Annie and Megan were brought into this world as sex workers. Somehow, that became an adventure in it of itself.


When she was done with her last client of the day, Annie was officially off the menu for the night and was allowed to spend the rest of the night how she wished. The Black Widow, the brothel she and Megan were working at, was a surprisingly fair and decent brothel compared to the brothels of other regions.

The Black Widow was run by Gawain, a beautiful, stern but fair woman who had a very deep hold on the sex industry of the Kingdom of Aurelia, the place where the girls landed in. Gawain had a reputation for not only having a sex empire consisting of tons of brothels, but also treating her girls like they're actual employees and not disposable tools. These girls were there to make her money, and they couldn't do that properly if she treated them like tools, after all.

Once she cleaned herself up, Annie headed downstairs to the dining hall where the whores working at the Black Widow would get their breakfast, lunch, and dinner. It was a surprisingly homey little area for girls who spent their entire day on their backs or on their hands and knees getting fucked nonstop. As she made her way into the hall, she spotted her friend, Megan, sitting at one of the tables.

"Hey, Megan!" She called out. Annie grinned when she only got a tired grumble in response.

Megan was the complete opposite of Annie. She was a little shorter than the pink haired girl, and sported a more curvaceous (and maybe even chubby) figure compared to Annie's tall, slender body. Megan had dark green eyes and light blue hair tied into twin tails that rested on the sides of her round face. Like Annie, she was dressed in a tight fitting white blouse with a deep cut around her cleavage and tight black shorts with brown boots. She was a hit for the customers that liked a bit more meat on their girls, but Megan's main clientele were of the nonhuman variety.

"Long night?" Annie asked as she sat next to her friend.

"Yeah," Megan sighed. "I just got out of pleasing a dwarf that had the stamina of ten men. I'm a fan of titjobs as much as the next girl, but doing it four times in a single night with one guy takes the fun out of it."

"Did you at least get a tip?"

"Oh yeah, a big one. Lots of pretty jewels too." Megan took out a ruby from her pocket and gave it to Annie. "Best thing about dwarves is that they like to tip with actual jewels instead of money."

"Better keep that hidden or you'll be hounded by the other girls." Annie said. It wasn't a joke. Whenever one girl got some really good tips like jewels or magic crystals, the other whores would practically swarm that poor soul looking for a handout. There was no harm done, but it wore away at one's patience really fast.

Mega rested her chin on her hands for a moment, not saying anything until she thought of something to talk about. "It's really odd."

"What's that?" Annie asked.

"It's odd how we talk about this like its normal." Megan said. "I mean, I know it's only been a year since we fell into this world, but it still feels very strange. Both the whole fantasy world thing and us being prostitutes."

"I'm still miffed about that, by the way." Annie grumbled. "We get dropped into this world and we don't even get cool magic powers. Not that I was expecting it, but I thought we'd get roped into some awesome adventure."

"I'd like to think of this as an adventure in its own right." Megan said, feeling a bit better now that she was rested. "I mean, we get to meet lots of new people, so that's something."

"Yeah, but only when they want to fuck us ten ways from Sunday." Annie huffed, playing with a lock of her pink hair. "Man, if only our parents could see us. Eighteen years old and sucking dicks for money. I'm sure dad will really be proud of me."

"At least the madam is nice." Megan smiled. "I don't know if I would've lasted long if she was like those Yakuza gang members."

It was true. Gawain was a woman who ran a tight ship, and she didn't take shit from anybody, not from rival crime lords, not from officials of the city council, and certainly not from royal officials. Yet, for all her criminal activities, Gawain rarely treated her girls badly, and even though some of her girls were brought into her sex ring unwillingly, she didn't treat them any less than human (or nonhuman) beings. That still didn't mean that she wasn't a terrifying woman to the girls; they were just lucky enough to not have gotten on the madam's bad side.

"Hey, girls!" A peppy voice called out.

They were approached by a young woman with short sandy blonde hair and freckles clad in a skimpy orange bikini top and shorts with thigh high stockings and boots. Her name was Cindy, and she was what passed for a supervisor in the brothel, managing the new girls and making sure they get used to life in the brothel while learning the ins and outs of the place. She was a nice woman who helped Annie and Megan in any way she could. Cindy certainly made their first couple of days within the Black Widow pretty decent.

"Hey, Cindy." Annie and Megan greeted her. "Are you done with your set?"

"Yup. Just got done a couple of minutes ago." Cindy said. She was an exotic dancer on top of being a full-time whore. The dancing part was of her own volition, as Cindy knew her way around a pole long before coming to the Black Widow and would sometimes teach the other girls a few moves. "But I just came here to give you a heads up. The madam says its your turn for the Tryout holes."

The girls groaned and Cindy gave them a sympathetic grin. "I'm sorry girls, but we're closing for the night, and she wants you two to handle the last bit of customers looking to relieve their stress. You know how it goes; all the new girls have to gain some experience with the holes before they upgrade to the full-service."

"Yeah, we know." Annie sighed.

"We'll take care of it, Cindy, thanks." Megan said.

"Thanks a bunch, girls. Be sure to come back here for some grub before you head off to bed. Can't go to sleep on an empty stomach." Cindy said and walked away, waving the girls off.

"Considering how many dicks I sucked today, an empty stomach isn't that big a problem." Annie muttered, making Megan chuckle.

"Annie please." She giggled. "Come on, the sooner we get this done, the sooner we can finish the night off."


The Tryouts were an area near the entrance of the brothel where girls would get picked to place their bodies within large holes in the wall, where only their ass and legs would be exposed to those who would pass by. It was a job that every girl in the Black Widow had experience with, seeing as only new girls were put into the holes these days. All newbies to the brothel would spend some time in the Tryouts as "trial runs" for men wanting to sample the brothel's goods before they were regulated to bedroom shifts like the older girls. And being the newest, Annie and Megan spent half of their time there letting random guys with enough coin fuck them to their heart's content.

Bent over with their asses exposed and open to the groping and leering of men coming and going to the brothel, Annie and Megan could only wait nervously for the first brave soul to walk up and use them like the whores they were.

As luck would have it, they didn't have to wait long, for two studs walked up to the wall just a little ways off from the receptionist area, their 10 inch cocks standing proud. They had paid the fee at the front booth and wanted to relieve their stress after a long day's work hunting monsters all day long.

Walking up to the girls' exposed behinds, the two studs gave each cheek a resounding slap before digging their hands into the soft flesh; to spread them and slid their hard cocks between their ass cheeks. Not penetrating yet but just teasingly sliding, wetting their dicks from the excess juices leaking from their moist cunts.

Annie let out a yelp at the first slap before tensing as she felt a hard dick start rubbing through the valley of her ass. It felt big, and she internally panicked, not really that experienced in taking big dicks yet despite being in the brothel for almost a year. What made it worse was that this shaft was bigger than most of her clients, thicker too by the feel of it. How could she possibly take a cock that big?

Megan squeezed her hand, derailing her panicked thoughts. "It'll be okay, Annie. Enjoy it. If you need help, just focus on me, okay?"

Annie smiled and squeezed Megan's hand back, letting her know she was okay.

Megan wasn't really that concerned with the size of their soon to be intruders. She was a bit of a size queen, born from taking the cocks of larger nonhumans like orcs and trolls and overpowered adventurers reshaping her cunt over the past year. She was glad she could help Annie deal with handling a big human cock. Not to mention it felt good that she could enjoy this with her best friend.

The two men lined up the heads of their cocks at the entrances of Annie and Megan's pussies before ramming five inches of their thick dicks in without any warning. Annie let out a strangled cry of pain that transitioned into a pleasurable moan as her pussy started to massage the invading member. Megan, on the other hand, opened her mouth in a long, drawn out moan as another couple of inches entered her tight teen pussy.

Annie was surprised by the sudden intrusion of the stud's cock before surprise shifted into bliss as he pushed his cock deeper, her breasts bouncing each time he plunged inside her. Annie felt his cock pulsing inside her as he let loose load after load of virile cum deep inside her, tossing her back over the edge as he deposited what felt like gallons of cum into her unprotected womb. Hot, potent cum flowed down her legs as he pumped more and more cum into her stuffed teenage womb.

Next to her, Megan was moaning like the slut she was as her stud railed into her. Struggling, the beefy man bit her lip as he tried to resist orgasming from the moment he stuffed her tight pussy. Each stroke was a challenge as her body gripped and massaged him tighter than any slut he fucked before. Shrieking as the stud hilted again and again straight through her cervix, Megan finally came. Grunting, the girl's clenching puss was too much for the stud as he started squirting his cum as he hilted one last time inside her spasming pussy. Megan let out an open-mouthed orgasmic moan like a complete whore as she felt her womb fill to the brim.

Breathing deeply, the two studs traded a glance as they pulled out of the tight pussies enveloping their still hard cocks. They took a moment to watch the massive globs of seed they shot into the tight teenage sluts leak out of their swollen pussies onto the stone floor.

One the other side of the wall, Annie and Megan shared satisfied smiles as they felt cum escape their overflowing wombs, holding each other's hands.

Until something came their way, these girls were stuck here making a living as teenage whores in this weird magical world. With nothing to call their own save for the clothes on their backs, all they had was each other. And that was just fine for these girls.