Into the Dragon's Den

by Omegathyst

Rating: mature
Tags: Porn, Fetish, Dragons, Mrs. Shy, Sex, Profanity, My Little Pony: Friendship is Magic
Length: 4123

Posey Shy's empty nest syndrome and boredom in the bedroom causes her husband to encourage her to go out on her own adventure...into a brothel full of equipped dragonesses~

Featured on September 29th-30th!

With Fluttershy and finally Zephyr Breeze making it on their own and fulfilling their own passions in life, Mr. and Mrs. Shy have done everything with their mundane lives as they could. Well, Gentle Breeze never tires of the different clouds he has collected. And Posey Shy would've been content to keep finding new types of flower to grow...if it weren't for her desires. Hot, lustful desires that her husband can't fully satisfy. With his blessing, Posey Shy goes and does something bold in many more ways than she could've ever expected. She doesn't just have sex, she doesn't go out and have a one-night stand with a stallion.

She goes to a hidden yet popular brothel, loved by many ponies. But not run by them, but ran by a group of dragonesses...packing extra equipment~

Cover art by Snow Quill 😃
Contest entry for the Striptember Contest
Contains y'all already know me at this point: futa dragon on MILF action, ponut/crotchteats fetish, open relationship/approving husband, prostitution, consensual gangbang, facefucking, anal (including double-penetration), vaginal, impregnation, and dragoness brothels!

Published 2023-09-29 17:20:00 UTC
Last updated 2023-09-29 17:20:00 UTC

Five on One

Posey Shy, the demure yellow pegasus with a dark red mane and mother of two, hummed a melody to herself as she used the pail filled with water to sprinkle onto the various plants that made up her garden. Equestria as it was in that very moment couldn’t have been better, with it being several years since the Legion of Doom were defeated. Zephyr had briefly stayed with them a few days after the horrendous near-division of Equestria, but the once freeloading young stallion had since left and continued his manestyling career with decent success. With the yellow mare being closer to her 50s now, Posey had no intention of having a third foal even with the perfect circumstances lined up for her and her husband to do so. At least, that’s mostly how she felt about it. If such an occurrence were born out of the heat of the moment, she would raise the foal and love them as she loved her daughter and son. But retirement had been very good to her and Gentle Breeze…

If not a tad bit boring to say the least.

It wasn’t quite like they ran out of stuff to do, not with her husband always finding different kinds of clouds to collect. Over the past few weeks, the green stallion had swore up and down that he would spend the rest of his life finding some absurdly rare cloud that was the color of a rainbow. Posey wasn’t any less happy with her garden, even doing something similar as researching on more challenging plants to raise in anticipation of the challenge itself. Her husband had a heart of gold, and they always made sure to make time for each other. Whether that was having a date at a quiet cafe or simply holding hooves on their respective recliners while reading different books, the two took deep satisfaction in purely the silence of good company. But as her husband’s name was Gentle Breeze, the green pegasus deeply lacked any sort of excitement in the bedroom. The sweetness of his ability to make love to her, gently nibbling her ear and always asking if she liked what he was doing, carried their sex life throughout the decades together. And she didn’t have any real reason to complain until the past few years, where everything had died down and she was only left with contemplation.

She felt her heart beating fast in her chest as she put the pail away in the shed nearby, having taken care of all of her plants. Today was the day she planned on opening up to her husband about her plight. She knew due to who he was as a stallion, Gentle would never get angry or overly hurt about the situation. But she didn’t want him to feel like she loved him any less, or that she would leave if he wasn’t comfortable with her seeing out other options. Slowly walking into the house they shared, watching as the stallion squinted his eyes at the cloud he held, Gentle glanced at his wife as he heard the door shut behind her.

“Oh hi honey,” Gentle smiled, tilting his head at the yellow mare’s scrunched up expression. “What’s up?”

“I need to talk to you about something important,” Posey gulped, not wanting to engage in the trivial small talk that made up a lot of their day-to-day interactions. Taking a deep breath, Posey continued. “Have you, um, ever found a mare attractive and wondered what it’d be like to…have an encounter outside of marriage with me?”

“Oh Celestia, are you asking if I cheated on you?” Gentle’s eyes widened for a brief moment before he shook his head. “No, I’d never do something like that. Not without talking to you about it first, why?”

“Talking about it first?” Posey repeated his words, surprised that the door to such an opportunity might’ve been cracked open for her.

“Well yeah,” Gentle shrugged. “Sex isn’t everything, so I don’t think going and having a hookup with someone else ruins a relationship. I think more ponies who get cheated on are more upset about the broken trust than the actual hookup itself.”

“Oh, that’s…interesting,” Posey placed a hoof over her mouth as she gave herself a few moments to choose over her words. “So if I really love you very much, but want to experiment on what else is out there…”

“Wasn’t I the only stallion you ever dated?” Gentle laughed. “Not counting the few makeout sessions you had in high school, of course. I’m more surprised you didn’t ask this sooner, especially with all the new species integrating into pony society, you know?”

Posey blushed, not even thinking about that particular aspect. With the School of Friendship having started shortly before the Legion of Doom was born, and then the three being defeated years ago, there had been an abundance of different creatures living alongside ponies. Zebras, dragons, griffons, Kirin, hippogriffs, yaks, changelings, and even the occasional donkey had moved into once pony-centric towns and cities. Posey had especially seen plenty of griffons moving into Cloudsdale where they lived.

“Just be safe, of course,” Gentle elaborated. “Lots of weirdos out there for sure. You’re a big mare though, I trust that you know where it is best to walk around.”

Posey Shy gulped on the big part, her brain going somewhere completely different than what he meant. She wasn’t a fat mare by any means, but the lack of physical activity in comparison to her younger years left her with a fat dumptruck that gave her some difficulty when it came to flying around. She didn’t leave the house much ever since a pair of young stallions whistled and tried to catcall at her. She certainly wasn’t that appealed by the idea of sleeping with another stallion, not when she already had that scratch itched by her husband already. There was a unique, wild and dangerous but not too dangerous experience she wanted to feel alive…

She just didn’t know what it was quite yet.

“Are you leaving right now? Or was this just a general conversation to keep in mind?” Gentle asked.

“Oh, just a general conversation,” Posey smiled. “Besides, how would I even find a proper hookup? Neither of us are the kind to go to bars, and most ponies at the local book clubs don’t just want to get down and freaky…”

“Well, there’s plenty of opportunity if you look hard enough,” Gentle pointed out, before lifting the book in his forehooves. “Now, would you like to hear about this book? I just got to a really good page.”

“Oh yes,” Posey galloped over to her husband’s recliner. “Let’s hear it…”

Walking in the near dead of night with her normally yellow fur plastered with a bright red blush on her face, Posey looked at the various buildings to find one identical to what the mares she met described. True enough to Gentle’s prediction, Posey had found herself in various social areas by herself in an attempt to find those interested in hookups. And while the trio of mares she met weren’t interested in a hookup with her perse, they had raved about a brothel they had gone to a couple of nights before.

“But aren’t brothels usually for stallions?” Posey had asked.

“Get with the times!” the younger mares had chirped with big smiles and infectious giggles. “Brothels are for any creature in need of those kinds of services, gender is irrelevant to that! Species for that matter too, I never thought I would’ve been so deeply satisfied by dragonesses…”

Posey blushed with the same tomato blush she currently had, the realization that the giggly and likely cum-drunk mares at the other table in the coffee shop were not talking about some strong stallion, but rather more than one dragoness had struck a cord that the yellow pegasus didn’t know she had. Like her husband had pointed out, Posey hadn’t had any experience beyond him; that wasn’t the couple of times she made out with stallions in high school. Let alone sex with completely different creatures. She didn’t even know if she’d be into the encounter, but surely this was why she didn’t want to experiment new acts with a stallion? Because she wanted to try something new?

Seeing a tall stony building with a dark red door that was almost invisible in the night, Posey’s ears perked up as she recognized the building by the mares’ description. Making sure that the generous amount of bits was still in the bag attached to her shoulders, Posey took a deep breath before trotting up to the door. Pressing her hoof on it, Posey remembered the reassurances she got from the mares on how accommodating these ladies were. For Celestia’s sake, their strictly held guidelines for their own work ethic was the only reason the Cloudsdale Council even let them have a building in the first place! So long as their business was between certain late hours, the dragonesses were golden.

Knocking on the door, Posey Shy waited a few moments before the door swung open and revealed a slim yet tall bright golden dragoness with curled horns like Ember, her pink eyes bright with excitement as her tail flickered from side to side.

“Why hello you~” the golden dragoness stretched her claw out, and instinctively Posey shook her claw before the reptile continued. “My name is Solar, and who might you be?”

“My um, my uh-” Posey stammered, absolutely gobsmacked by the physique of this Solar lady. With her cartoonishly long eyelashes and distinctively feminine voice, the yellow pegasus was taken aback by what she looked at down there. Hanging between this dragoness’ legs was a thick dark yellow futa cock so big that the tip touched the floor, the MILF wondered how this young dragoness could even walk around with such an endowment! Taking another deep breath and feeling a rush of embarrassment at such hesitation, Posey pulled her hoof back and smiled. “My name is Posey Shy! Sorry, I’ve honestly never met a dragon before. Besides this little young one my daughter and her friends bring over, and he was raised by one of them-”

“You really don’t need to explain yourself, Posey,” Solar snickered. “Plus, if I have permission to be so blunt, we both know it's not my dragon qualities that are startling you. Come on, let’s get you inside and out of the cold. Chances are, you’ll need to take a look at my friends to immerse yourself~”

“Immerse myself in CELESTIA!” Posey gasped as she took several steps into the building and saw the four other dragonesses resting on bean bags and couches. There was a bright green one, a red one, a dark purple one, and a white one with golden curled horns. Regardless of all their physical differences in appearance, they all had the same aspect in common. Between all their legs were futa cocks that were all darker shades of the rest of their scales. Even though they were varying lengths and widths flaccid, they were all larger than any flaccid dick Posey had seen on a stallion.

“The green one is Mamba, the red one is Vermillion, the dark purple one is Eclipse, and the white one is Angel,” Solar explained, closing the door behind Posey and placing a claw on the mother’s shoulder. “Er, are you alright? Y’know we wouldn’t think of you as a bigot or anything if you didn’t want to have sex with-”

Solar removed her claw from Posey’s shoulder, grabbing as much of her futa dick as she could and holding up the thick delicacy towards Posey without it touching her. But the damage was already done, the fat-assed yellow mare’s nostrils getting flooded with the overwhelming spicy yet earthy musk of the dragoness.

“-big dicked, virile, rough, powerful, and attentive dragonesses,” Solar hummed as she wiggled her length a little before shrugging. “Oh well, perhaps we’ll see you aro-”

“WAIT!” Posey shouted before she could think twice, causing a big smirk to crack on Solar’s muzzle before the pegasus continued. “I um, d-don’t even know your rates?”

“Oh!” Solar giggled. “Well, that’s fair enough I suppose. Oral sex and tail-fucking is at 50 bits per session. Regular fucking is 150 bits per position, and we’ve got ponut pounding at 20 bits per position…”

“Why is pounding my ponut come so cheap?” Posey whispered. “There’s still lube involved, right?”

“Yeah, of course!” Solar chuckled. “We’re dragons, not monsters. Well, something me and my ladies found out a few weeks into our work is that we really love fucking a mare’s backdoor. We’d actually have it for free if we weren’t simultaneously also running a business to live here. Only exception is Angel over there. She loves spilling her seed down a mare’s throat…”

Posey looked over at the white dragoness with golden horns, her green eyes narrowed at the yellow mare and grinning as if she was already imagining doing so in great detail. Posey thought about the amount of bits in her bag, which wasn’t much. It was a measly 80 bits, not even enough to get one of their dicks inside her needy pussy.

However…

“You said ponut pounding is only 20 bits per position?” Posey gulped. “Well, um, I would like that but I only have 80 bits and I was hoping to get my…pussy fucked as well.”

“Well, we normally don’t do freebies,” Solar began, and Posey Shy tensed up as she was readying herself for the inevitable rejection as the yellow dragoness continued. “But, with a super cute older mare such as yourself…we want to have a lot of fun with you. So three of us can take that backdoor of yours, one of us can claim your pussy, and Angel could have your mouth. All for that 80 bits, hun. But don’t tell anyone, these aren’t discounts we normally give…”

Posey’s ears flattened as she was confronted with a completely different offer than she expected. All she was looking for was to get her pussy filled with dragon spunk and maybe her ponut once, and all of a sudden, Solar offered for all five of them to use her like a fleshlight! Watching as the four dragonesses hopped off the beanbags and couches as they walked towards her with their predatory eyes, Posey felt her heart racing in her chest. She never had anything closely resembling a risque encounter, and here she was moments away from deciding on whether or not she wanted to be railed into oblivion! Stammering profusely, feeling her brain shut down as she looked at the dragonesses, Eclipse gave a gentle smile as she lifted Posey up with her claws and held her up like a big teddy bear.

“Poor thing,” Eclipse had the most sonorous voice of the five, one that could easily lull a pony to sleep or relaxation as she moved her digits in a small massage on the mare’s body. “You’ve never had such an experience before, have you? Perhaps you have a husband back home, one that is subpar at best? Bet he’s got a great personality though, huh?”

That last sentence was surprisingly heavy with sarcasm as the purple dragoness’s smile twitched a little, and Posey felt a deep sense of nervousness at what she was about to do. Then, she remembered what Gentle Breeze had told her. He wasn’t the slightest bit offended by her perception of his shortcomings, wanting her to give into her desires with one life to live. Taking a deep breath, Posey looked at the dragonesses.

“Perhaps,” Posey admitted. “Well, I’ll take the deal. I’d like to see what else there is besides sex with one stallion.”

“You wouldn’t believe what is beyond that~” Mamba hissed, her voice more scratchy as she licked her green muzzle. “Please, Solar, let me start first. I can see her crotchteats on full display and I don’t think I can hold myself back much longer…”

“Of course, you and Angel can spitroast her,” Solar decided. “Let me get the lube, generously apply it to you both. Posey Shy, you’re going to be in for quite the time. Do you have any particular preference? We do have several giant beds on the second floor, or we can just do it on the beanbags down here.”

“I would like the second one, a bed won’t really be necessary for what we’re about to do here,” Posey smiled, and Vermillion walked over and looked at Posey with her sharp amber eyes before reached her claws out to the yellow-furred MILF’s dark yellow crotchteats. Twisting them right off the bat and earning whorish mewls from Posey as her ears flattened against her dark red mane, Posey knew her reservations would crumble quicker than she thought…

“Mmmph! Nnngh!”

“Look! I think the bitch likes it!” Mamba cackled.

It took less than half an hour for Posey to really get into the swing of everything, the true mark of a MILF under a dry spell of years in the making. Laying on her back on the beanbag with her mouth wide open and her legs spread open, the green dragoness Mamba had her claws resting on Posey’s legs as she was pistoning her nine inches in and out of the mare’s lubricated and incredibly tight ponut. Angel had cut off the mare’s howls with her preference of facefucking a mare, with her dick moving back and forth in the mare’s mouth a little bit slower. Angel knew that Posey had to get into the practice of holding back her teeth and breathing through her nostrils, especially with a blowjob as lengthy as this one. Snorting as she enjoyed the MILF to the fullest, Angel had her claws resting on the mare’s chest as she rocked her hips back and forth. Mamba moved her claws from Posey’s legs to her crotchteats, groping the mounds as she pistoned the mare’s backdoor even faster.

“This whore is only going to love getting it in the ass from now on,” Mamba declared. “I think we’ll make her into a butt slut before the night is over!”

“Perhaps she already is one now,” Angel agreed. “Although I hope she still comes back to blow me, it’d be a shame if she was thrown off oral entirely…”

Posey barely listened, her body thrown into an euphoria that she didn’t realize was possible. Getting spitroasted by two futa dragonesses as one plowed her mouth and the other railed her squeezing backdoor, was a sensation that made her want to relax and give in, becoming a fleshlight to their desires towards her. Although the relaxing part was next to impossible with Mamba twisting her nipples next, making the yellow mare moan loudly around Angel’s cock as she was about to cum. Amazed that she was able to take two dicks at once for the first time so easily, Posey felt a deep excitement as Mamba returned her claws to the mare’s legs and jackhammered harder.

“Yesssssss, I’m close!” Mamba snarled, throwing her head back and releasing a roar as she came moments later. Hilting inside Posey Shy with her entire length, her balls slapping against the MILF’s fat ass, Mamba shot thick ropes of her seed inside the yellow mare and claimed her asshole. And without even being so much as having her clit or pussy touched, Posey cried out around Angel’s dick as she came marecum all over Mamba’s stomach. Angel, looking down and seeing the yellow pegasus mom’s thick marecum spraying all over her fellow dragoness as Mamba unloaded her fat dragon load inside the MILF’s asshole, also reached her breaking point with a couple more thrusts. With only six inches, Angel was more than okay with deepthroating the horny mare and slapping her balls against Posey’s closed eyes before coming into the pegasus’ stomach. And fortunately, the yellow mare gulped down each rope with no problem whatsoever. The two slipped their dicks out of Posey’s mouth and ponut respectively, and Angel pressed her claw against the yellow mare’s cheek.

“Hey, was that all good?” Angel asked. “Any requests for the next two dragonesses before they have a go?”

“Haah, p-please knock me up,” Posey blurted out the words with a dizzying yet desperate need as she looked right at Solar. She knew the yellow dragoness and one of the others would take her ponut and pussy at the same time, but Posey had a preference for which one she wanted to breed her. The leader of the group, the one that greeted her at the door, and it made Posey feel so easy. Somehow, that just made her pussy clench as she felt a stream of dragoness cum pouring out of her asshole. Solar’s pink eyes widened before she flew over to the beanbag and lifted Posey up. Replacing Posey on the beanbag as she opened her dragon wings and rested on her back, she pressed the tip of her dick to the mare’s breeding hole. Ever since she and the others started the brothel in Cloudsdale, she had always wanted to impregnate an older MILF with another foal. And never such an opportunity came until now, and Solar wasn’t about to waste the gift dropped on her lap. Waiting a few moments till Eclipse pressed the tip of her lubed cock to Posey’s dripping backdoor, Solar looked to the cum-drunk yellow pegasus MILF.

“Are you ready?” Solar asked.

“Yes, please fuck-AHN!” Posey wailed with a deep blush as she felt the tip of Solar’s ten-inch and thick length plunge into her pussy and widen her with mostly pleasure with a twinge of pain from the much thicker length inside her. On top of that, she felt the dark purple dragoness’ eight-inch length enter her loosened backdoor with a bit more ease as she pushed it further inside. With a dick in her pussy and one in her ponut, it mentally broke the MILF even more than the first round. Unrelenting pleasure rushed throughout her body like she was floating on clouds of lust that never seemed to end. She couldn’t imagine herself going back after this, even if she fully intended on staying with her husband. For one, Solar would likely fulfill the mare’s request and knock her up with a foal. Or egg, Posey didn’t really know how pony-dragon breeding worked nor did she care at the moment. Just so long as the dragoness creampied in her and claimed Posey, the MILF would want more and more. Maybe even more than just dragons as Posey saw herself fucking griffons, zebras, friends at the book club…

Maybe there was something to making friends with other species, Posey thought with a knowing giggle and moan.

Feeling Solar’s claws on her hips as the golden dragoness bounced her up and down like a living fleshlight, with Eclipse sinking her dick further into the pegasus MILF’s backdoor with each downward movement Solar made, Posey moaned throughout the building as she let all her thoughts melt away. Only letting the vicious plapping of both her holes, of two pairs of balls slapping against her body, and the fulfilling and thick penetration take over her senses. And the yellow-furred MILF lost track of how long she was experiencing this, only coming back to her senses a little when Solar and Eclipse starting plapping her especially faster as the leader dragoness grunted.

“Are you sure about getting knocked up, what will your husband say?” Solar chuckled, shaking her head a little before continuing. “But seriously, tell me where to rele-”

“INSIDE!” Posey demanded, and Solar hilted herself as she came. And the unthinkable happened, something that completely broke Posey. Vermillion had snuck up on her, sticking the tip of her cock inside Posey’s ponut while Eclipse still had her dick inside. With a dragoness releasing her hot load inside Posey’s cunt and impregnating her, while having two other dragonesses double-penetrating her looser backdoor at the same time…gave Posey Shy the hardest orgasm of her life. Being stuffed in a way she didn’t even think was physically possible, Posey’s body convulsed as she came all over Solar’s dick and felt her ponut clenching like a vice against the two dragonesses’ dicks stuffed in her ass.

With the orgasm having lasted a full minute, Posey felt her body on the brink of passing out afterwards with only Eclipse and Vermillion still double-stuffing her ass to keep her awake. Giggling like a drunk teen, Posey knew she was going to have quite the funny explanation to make to her husband the next morning…