Chapter 1
"Oh, horse-apples, what am I doing here?"
Brann looked around, taking in the unfamiliar surroundings. It was the first time he visited a place like this. The interior of the brothel was decorated with warm colors, lush silk curtains creating the illusion of curvature in all rooms. The air was filled with a strange, enticing mixture. For one part it smelled of different perfumes, each brand belonging to another one of the mares and even the one or two stallions that were working here, but there was also something else. Something else that made his nostrils flare whenever he took in a deep breath.
His nervousness was only becoming worse as he began to feel lightheaded now, too.
He levitated the flier in front of him, reading it to himself again: "Madame Jubilee's Cherry Field - come pick your favorite from plenty of juicy choices! 2 for 1 special offer for pairs!"
Plenty of choices indeed. He had already sweated a lot as he had entered the brothel, the large body guard just grunting at him before letting out a hearty chuckle once the slender unicorn passed him and now it was getting only worse as he felt more sweat collect on his forehead.
Just right by the entrance two beautiful mares were playing with each other, slowly, and beckoning Brann towards them.
"Oooh, such a hunk of a Stallion! What do you think sister, think he can handle us?"
"Only one way to find out, dear sister...what is the matter, Adonis? Cat got your tongue?"
"Come here and we'll show you how much fun you can have with twins..."
Swallowing hard, Brann barely managed to stop stuttering, backing up with shaking legs.
"Ahhhhahahaha! It's okay, really! I'll just take a look arou-OOF!"
He bumped into something soft. Immediately he felt a pair of hooves pulling him into a tight, warm, yet soft hug.
A whisper came into his ear: "Mmmmh, what a sweet little colt do we have here? You wanna play with momma? Come here and lemme snuggle you!"
Brann turned his head around. What he saw was easily the fattest mare he had ever seen. While he doesn't mind some extra cushion' for the pushin', she was way above what he was comfortable with. Also he didn't feel like being crushed today.
Her hooves were rubbing his belly, one of them wandering down dangerously low.
"AAhhhIIiiii will consider your offer, thank you very much! Ahaha!"
With that, he wrangled himself out of his soft prison. Looking back at "momma" he could see that she positioned herself up a bit. Sitting on her broad haunches she kneaded the bountifulness of her plush belly and winked towards him.
"You will be back deary, they always come back to momma!"
With another nervous chuckle he just turned his head back forwards quickly. Unfortunately for him that meant that he headbutted whoever was in front of him.
"Ow! What the hell, dweeb!"
As the pain cleared from his head, Brann froze in shock after seeing who he just almost knocked out.
In front of him was a Gryphon, rubbing her head. She was wearing a leather top, with cutouts to accentuate her several pairs of breasts, each nipple adorned by a shiny little piercing. On her hind-legs she wore thigh-high leather socks, which accentuated her firm and muscular thighs and butt.
"You wanna play rough, huh!? Well, you can have rough!"
Before Brann could even react in any way, the Gryphon had already pinned him down.
"Let's see who can dish out more", she said, licking his face, "when I'm done with you, you're going to need a walking aid."
Brann was just about to scream as...
"That's enough! Release him!"
The laughter and smalltalk between the brothel employees came to an eery silence.
"Come here, Gilda!"
"O-of course Madame Jubilee!"
The Gryphon got off Brann, allowing him to see this Madame Jubilee. There was a certain elegance to the way she trotted over to him with her cigarette holder in her mouth, her two-shaded red mane coiffed up in a spectacular fashion. Her green eyes shined against her bright, cream colored coat and on her right cheek a small beauty mark accentuated her face perfectly. The way she swayed her hips was magnetizing and telling of her intentions and occupation. This mare was a professional, her movements calculated and shaped by many years of experience. Yet she seemed to be barely older than him, making him wonder how early she started with this business. She stopped and turned to the side to face the Gryphon.
"Gilda, let me see your head...tsk tsk tsk, he got you good, my dear. Head to the backroom and get yourself checked, I don't want you to get any bad headaches."
"But Mada-"
"Gilda, please," she interrupted the Gryphon more sternly.
The short exchange allowed Brann to get a more detailed look at her. She was wearing soft black lace panties that snug on her curvacious rump. Her legs and particularly her thighs were accentuated by a fitting pair of long socks. And between her hind-legs...oh my.
Brann could feel his face redden at the sight. Between her hind-legs, just above her panties, Jubilee was wearing a black lace crotchbra, tightly hugging the round mounds of her gratuitous crotchboobs. While they were not Milky-sized, it was clear the the poor bra was struggling to contain what was easily one or two hoof-fulls of soft, sensual flesh.
It didn't take long for Jubilee to notice where Brann was staring. She smiled, after waving the Gryphon away she turned to Brann, who was still on the floor. She took a moment to measure him up, her half lidded eyes soaking up all the small and larger details on the nervous stallion.
While Brann was not overly impressive overall, he was definitely not bad-looking. He was tall and thin, giving him a bit of a lanky appearance. He had a thing for getting himself in awkward or embarrassing situations, which meant that his lavender coat in his face was often out-shined by his reddening cheeks, as it was the case right now.
She pulled out her cigarette holder and blew a puff of smoke towards Brann. Oddly, the smoke didn't smell unpleasant to Brann at all, but there was a very distinct cherry flavor in it.
"This is your first time in a place like this, isn't it?" she said, her voice as thick as honey.
"I uh...ah..."
Brann couldn't help it. His eyes constantly darted between her with pink eyeshadow enhanced eyes and her generous cleavage.
"Uh...I...I am sorry! I didn't mean to bump into her, I s-swear!"
"Hahaha! Don't you worry your little head about Gilda. She is easily the most thick headed Gryphon in all of Equestria. Now..."
She moved closer to Brann, towering over him. Gently, she glided her fore-hoof along the sheath of Brann's member. He hadn't noticed before that he was already half erect. She glided her hoof up and down for a bit. Brann's blushing intensified.
"...are you here for some fun, or are you just sight-seeing? We have special booths for that, too..."
Brann didn't really know how to react in this situation. He was lying on the floor, while what looks like the matron of this brothel slowly coaxed his mast to full height in front of several mares of the business. The Twins giggled while Momma procured some of those theater-binoculars from somewhere to get a more detailed look while snacking on an awfully creamy looking eclair.
"F-fun! Yes! Fun! That's what I'm here for! F-Fun! Ehehehe!" he almost yelled as he shot up to a standing position.
"Well, who do you want to take up to your room then? Have you made your choice yet, or should I introduce you to our other employees?"
Brann thought hard, looking around the room, but couldn't avoid looking at Jubilee's plump rump and her tightly packed teats, her half lidded eyes fluttering at him as she pulled another breath of whatever it was in that cigarette holder. He bit his lip, closed his eyes for a second. He knew his mind was already made up the moment he saw her strutting towards him. After a deep breath, he muttered:
"I would like to go with you, Madame Jubilee."
"Pardon, I didn't quite catch tha-"
"I WOULD VERY MUCH LIKE TO TAKE YOU UP TO A ROOM, MADAME JUBILEE!" he blurted out, his whole body tensing up and his face crunching at his own awkwardness.
Again, a sudden silence in the room. The twins held their breath as they held each other. Momma leaned forward a bit, silently munching on her treat, as if she was watching a particularly exciting play.
Jubilee looked a bit perplexed, but then smiled and laughed.
"Ha...hahaha! You want to take me with you? I don't really serve...first timers."
She began circling Brann.
"Although, you are kinda cute...and considering your...," She stole a not-so-quick glance down to Brann's package, "...courage, I may be willing to make an exception. Follow me."
Her tail brushed Brann's chin, guiding him to follow her.
Like in a trance Brann followed Jubilee, not really able to take off his gaze from her voluptuous backside swaying from side to side, like a pendulum hypnotizing him. He didn't even notice the Twins clopping their hooves in applaud at him, or Momma outright hollering at him. They also passed Gilda who just left the break room. Gilda just stood there for a second, dumbfounded by seeing Jubilee taking in a new one, before breaking out in loud laughter.
"I hope this guy knows what he got himself into! Poor fella won't be able to walk after her treatment, either!" she thought to herself, wiping away a tear from her eye.
The inside of bedroom number four was as comfortably designed as the rest of the brothel. Warm colors helped to a achieve a welcoming and homely atmosphere, candles illuminated the room in soft light, their scent relaxing on the nerves. In the middle of the room was a large, round bed. While most would deem it to be a bit tacky in usual situations, it fit the bill perfectly here.
Jubilee guided Brann towards the large bed, putting her cigarette holder aside. She was going to have something else occupy her mouth soon. Then she undid her hair, setting her hairpiece aside as well.
"Go ahead big boy, make yourself comfortable...I will take good care of you."
She shoved the lanky stallion on the bed, putting him in a sitting position at the edge of it. Jubilee rebalanced herself on her hind-legs, rubbing his chest, planting kisses everywhere.
"So, tell me about yourself..." she kept wandering lower and lower, "I don't think I've ever caught your name, sweetheart."
"Oh, well, haha, my name is...BrAH-Ahnn!"
A playful giggle from the mare.
"Go on..."
She steadily kept wandering down, spreading his slightly trembling legs before licking his sheath.
"I-I am from Trott-oh Celestia...Trottingham!"
"Oh my, all the way from Trottingham?"
She licked one of his balls before nuzzling his ball-sack, deeply inhaling his musky smell.
"You came from so far away just to visit my brothel? What a naughty colt you are!"
She proceeded to rub her face on Brann's testicles, rubbing his hardening shaft with her hooves.
"I will make sure you won't ever forget your visit here, sweetheart..."
Brann's heart was pounding in his chest. Jubilee began climbing towards his face, licking the entire length of his erection. She affectionately kissed his glans, which was eagerly twitching in anticipation.
"Mmmhhm...you're a tall one, you know that? I'm going to have lots of fun with you."
"Is that so, yeah? Hehehe...Thinking about it, I kinda get that a lot...oh!"
She moved back down again, slowly stroking and kissing Brann's member on her way.
"Brann, dear..." she turned around, wiggling her plump rump towards him, "could you help me out of these?" looking back and forth between her black lace panties and Brann's beet-red face.
She swayed her tail to the side, so he had free access to her backside.
"Oh-of course Madame Jubilee..."
His horn lit up, grabbing the underwear with his magic.
"No Brann, use your hooves."
"Yes, Madame!"
"And please, Brann, just can call me Cherry."
"Of course! S-sorry!"
A small giggle from the working mare.
"You don't need to be sorry! You're adorable! Now..." another wiggle with her butt, "I'm waiting, dear."
Brann swallowed hard and leaned forward, getting off the bed and balancing on his hind-legs. His shaking hooves were inching towards Jubilee's posterior before he firmly planted his hooves on her backside. Leaning forward like that also had the effect of his erection landing squarely on the dark fabric. Cherry didn't mind at all. She began rhythmically gyrating her hips back and forth, the friction of the fabric on the underside of Brann's shaft sending a shudder through the stallion.
He fumbled around with the band of the panties for a moment, but finally managed to get a grip under it with his hooves. Jubilee enthusiastically wiggled her butt, trying to entice him to pull the restricting piece of clothing off. Brann slowly peeled the lacy underwear off, rubbing Jubilee's cheeks, feeling the soft flesh under his hooves. Jubilee swung her hips from side to side, letting the panties to drop to the floor.
"Mmmhm, keep rubbing."
She lowered her front, sticking up her behind further. Brann did as he was instructed and continued to rub Jubilee's cutiemarks on both sides. With each gyration of her hips he could feel his member become a little bit more engulfed between her soft haunches. Brann moaned as the soft sensation rubbed him just the right way.
"Mmmmhmm, you like this, don't you?" The mare giggled to herself, continuously increasing the pace. "Rub harder."
Brann nearly passed out right there. All the teasing before, and now the sensation of his tool being surrounded by these soft, warm buns. Cherry Jubilee's plot felt fantastic. She wasn't a fat pony at all, she had just the right amount of chub on her figure that packed on her at just the right places, like her heavenly hips, her bountiful butt-cheeks and her titillating te-
"Ohhh, Aaahhh!"
"Brann, are you oka-OOh!"
Jubilee had turned around just to have a hot strand of sperm hit her right on the nose.
Brann just stood there, his mind lost in bliss as his member twitched and shot out rope after rope of cum for at least half a minute. After he got back to his senses, he realized what a mess he had created.
"D-did I just...? Oh wow, I'm so sorry I-I-"
"Now Brann,.. " She licked some of the ejaculate off her face before procuring a washing cloth from somewhere and cleaning herself up a bit, "...you have to warn a lady before you shoot off your load."
"I didn't - please - I mean - you see..."
"You can't just waste your virile juices like that."
A smile crept up on her face as she turned around once again, closing in on Brann.
"And then y-you see- wait what?"
She was already hovering next to him, pushing him onto the bed entirely. Brann gulped once more as the mare climbed on top of him. He could feel her lower her crotch onto his.
"I hope you're up for another round, sweetie. You're mine for tonight."
With that she began kissing his long neck while rubbing her entire body up and down on him. Brann could immediately feel how his member was trapped between two soft mounds again - a sensation that quickly brought new life into his softening rod.
"Oh Celestia..."
A groan escaped his lips. Not only was a lust crazed mare on top of him, but he felt the base of his penis being rubbed between Jubilee's generous cleavage. He could sense her erect teats straining against the thin fabric of her bra, yearning to escape their prison.
"You think I didn't notice how you stared at them when you first saw me? You're such a naughty stallion! My fat teats are the reason why you wanted to choose me, right?
"No! I mean, y...y-yes!"
"Do you want to touch them? Rub them between your hooves?"
"Hnnnhyes!"
"Do you want to lick them?"
"Oh Celestia, y-yes!"
"Mmmmhm...I can't hear you...tell me what you want to do."
"Madame Jubi- I mean Cherry, I..."
"Yessss?"
"I want to fondle your crotchboobs! I want to knead your mammaries! I want to suckle your milkbags! I-I..."
"Hahaha! Oh my Brann, you're suddenly so direct! Looks like I hit a nerve...but your honesty shouldn't go unrewarded."
Jubilee got up, turned around and placed her hindlegs on the sides of Brann's head, giving him a face full of cleavage. Meanwhile she looked at Brann's fully erect mast, standing proudly before her. She licked her lips at the sight.
"Mmmhm, what a sight...Brann, be a dear and undo my bra."
She stuck her tongue out to greet her big friend once again as she noticed Brann blindly fumbling with his hooves, failing to open the clasp of her bra and grunting in frustration. Jubilee stifled a laugh.
"It's okay Brann, even I have problems taking it off in the heat of things. Just use your horn."
"I should finally get me one in a bigger size" she thought to herself before returning her attention to the needy stallion rod in front of her.
She gave it some affectionate licks, kissing the glans, tasting some of his fresh pre on her lips.
Meanwhile, Brann sighed in relief as he heard the click of the clasp opening. The world seemed to move in slow motion as he saw the bra straps gliding down, the cups flowing down towards his face. The tender flesh of her cleavage shook slightly as it slid down a bit, finally free of the confinements of their bra prison, freely swinging with each of her movements as gravity made them dance in front of his face. A dopey grin formed on Brann's face as he threw the bra to the side.
"Ooh! Well someone's in a hurry!"
Jubilee giggled to herself as she felt Brann diving his muzzle into her inviting cleavage. He was eagerly lapping up every sensation he could get. Applying some pressure from the sides with his hooves, he motor-boated her soft breasts as if his life depended on it.
Jubilee opened her mouth, licking her lips in preparation of taking in Brann's large tool. She wrapped her lips around his head, already flaring and ready to shoot off again. Little by little she swallowed more of his hot throbbing meat. Being a professional, she managed to fit in quite a bit of him inside her throat, but even she had her limits. Just past his medial ring, she began bobbing her head back and forth along his length. Lewd slurping noises could be heard, her tongue riding along his shaft, her drool dripping onto Brann's lower abdomen.
The stimulation only encouraged Brann further. He took his hooves off her breasts, stretching up to her flanks. Grabbing at her cutiemarks, Brann pulled her hips down to his face, basically getting smushed by Jubilee's cleavage. Alternating between the beautiful mounds, he latched on to each engorged teat, sucking greedily.
Jubilee moaned into the large dick in her throat, the Brann's aggressive admiration of her milk-makers causing her to feel lightheaded. If he kept up doing this, she might actually-
Brann moaned loudly as his eyes opened in surprise. All of his senses went wild when he felt the first droplets of warm milk splash onto his tongue and and into the back of his throat. He groaned as the sweet taste exploded in his mouth, jerking his hips into Jubilee's greedy maw.
Jubilee moaned even harder than before. Her throat was almost uncomfortably full, Brann pumping into her with abandon while constantly teasing her sensible nipples. Her arousal manifested itself as a heat in her loins, wetness leaking from her needy, winking entrance. Without warning, she could feel his penis twitch, feel how his load traveled up his shaft and down her throat, until it splashed out almost directly into her stomach. Her eyes rolled up as she tried to swallow as much of the precious juices as possible, her lewd slurping noises mixing with her exited moans.
Brann's aggressive assault on her teats ceased as he began to pass out in post-orgasmic bliss.
But Cherry Jubilee wouldn't have it.
She got up instantly, Brann's member leaving her mouth with a long -shlorp- and an audible pop. She straddled herself right under Brann's face, her milky breasts hanging right over his mouth.
"Oooh, we're not done yet, Brann!" she said, her breath growing heavier with each second she rubbed herself on him. "Drink! Drink, you perverted milk-fetishist!" She guided one of her leaking teats to his mouth. Brann began sucking on the sweet treat instinctively, his mind still a bit foggy.
"Come on, I know you still got some life in you!"
It took about three minutes, but the combination of being literally served his fetish and Jubilee's needy smell entering his nostrils urged the basic instincts in his body to ready himself for one last round.
"Yes, ahaha!", she yelled triumphantly as she saw him getting hard again.
"Uhhnn Ch-erry...Madame Jubil...I think I need a pause..."
Jubilee didn't lose any time. With the grace of a young mare in heat she positioned herself over Brann's erection. Rubbing her needy folds along the tip of his member, she coated it in her arousal, her excited cherry touching it as if to coax it into her.
First slowly, but more and more recklessly she lowered herself onto him, biting her lip. She needed to have all of him. It has been so long since she had a customer of this size; and she would enjoy every single inch of him.
"MmmmmmooooaaaaAAAHH!"
A long, loud moan escaped her mouth when her hips finally connected with his. Brann groaned again. He was tired, spent. But he just couldn't deny how nice it felt, how her wet warm tunnel clamped around his length, welcoming every inch of it.
Jubilee started by gyrating her hips, getting a feeling for the mighty tool inside her at first, but it didn't take long before she was all-out riding the pony. Slapping noises mixed with her moans as she repeatedly crashed down onto Brann's hips. Her soft breasts jiggling freely, slapping onto Brann's lower belly, coating it with milk splashes in each impact.
Brann was already nearing climax again. It wasn't helping that there was a lewd mare dancing on top of his cock, bouncing her pendulous love pillows right in front of him. He decided to take up some action and reached out to her teats, roughly kneading them.
"Oh yes Brann, you naughty colt! Play with them! Ah!"
Brann mustered all the strength he got left. If that crazy mare didn't cum soon, this would be the end of him. He could feel her tighten around him, she couldn't be that far from climax.
Jubilee loved the fireworks of sensations inside her head. The thick cock-meat twitching inside her hungry tunnel, the rough abuse of her sweet milk-factories. She leaned down towards Brann's face, her hot breath washing over his sweaty body.
"Ah! Ooooh! Brann, dear, oh you're going to- ah! Like this!"
With that she leaned back up again, frantically riding her pony to climax.
"Ohh! Ahhhh! AAHHHHH!"
In one moment her entire body tensed up, shaking as waves of pleasure shot through her very being, her breasts squirting thick streams of cream in sync with her heartbeat. Jubilee's orgasm also caused her insides to tense up. Contractions wander through her body repeatedly gripping and releasing Brann's penis, coaxing it to release its seed.
A final grunt escapes him as he can finally feel his flare enlarging inside Jubilee, ropes of his potent juices gushing into the sweet mare before he passes out.
Jubilee enjoyed sitting on his softening member for a bit, riding the post orgasmic bliss to its end before lifting herself up off Brann with shaky legs.
She collected her things, blew out the candles and left the room, allowing Brann finally some rest. She could still feel herself leaking some juices. Even now she felt relatively full, the warmth of Brann's cream splashing inside her. She chuckled to herself, glad that she didn't need to worry about any unwanted surprises thanks to a rich Zebra client providing her house for free with special herbs.
Out of the room she turned right and shortly right again, opening a crudely hidden door.
Inside she could smell the excitement of a mare who just had a particularly enjoyable show to watch.
"That was amazing! Like when you let him play with your butt, and then the part where you sucked him off while he sucked on your-"
"I'm glad to hear you enjoyed this special arrangement, Cookie. Your colt-friend is definitely a keeper, you should take good care of him."
"I even took notes! This is going to be so useful!"
"Ahahaha! You're one crazy little mare...So about the payment..."
The brown tubby mare stood up and trotted over to Jubilee, smiling.
"You know, watching you two go at it was a lot of fun...and now I feel all riled up...is the 2 for 1 offer still valid?"
Jubilee smiled back at Cookie.
This was going to be a long night.