A Mother's Lesson in Confidence

by MajorDude

Rating: mature
Tags: Mrs. Shy, Sex, My Little Pony: Friendship is Magic, Zephyr Breeze, Porn, Windy Whistles, Fetish
Length: 3204

Windy teaches Fluttershy's mother, Posey Shy, on how to be confident. Zephyr is involved for naughty reasons...

Windy Whistles teaches Fluttershy's mother, Posey Shy, on how to be confident. After all, Fluttershy over the years has gained some confidence of her own, so her mother decided that it's time for herself to learn to be more bold. Windy is more than happy to teach her friend on being confident. Unfortunately, in order to truly achieve this, she secretly invited somepony else to join this little lecture...

Contains: Mommy-Domme, Blowjobs, Spanking, Incest

This was written for Pillowfight as a part of Summer Sin 2023 story exchange!

Published 2023-08-04 06:50:00 UTC
Last updated 2023-08-04 06:50:00 UTC

Have fun, Pillowfight~

Summer was always brutal during Ponyville. It wasn’t so brutal for the swimsuit businesses and the ponies selling ice cream, but the heat always did remind ponies on why Celestia was feared throughout Equestria. Still, ponies found a good method of coping by doing various summer activities, such as poolside activity.

By pure chance, three pegasi were participating in said activity.

Two pegasi, Windy Whistles and Posey Shy, found themselves relaxing by the poolside, their laughter mingling with water splashing and light conversation.

"Thank you again Windy for agreeing to do this." Posey said meekly as she scratched the back of her neck. "I know this sounds bizarre-"

"Oh, nonsense!" Windy Whistles exclaimed, waving her hoof at her friend. "This sort of thing never bothers me and I'm glad to help you!"

"Thank you dear." Posey responded before looking away.. "My daughter is getting a bit more bold over the years. It seems like only yesterday she had a hard time to actually talk. It seems only fair that I learn to be a bit more bold…"

"And what better way than here!" Windy pointed out as she stretched her forelegs out. "Rarity is such a dear to let us use her pool for today. She's out on a date with her 'dragonfriend' so that gives us the whole day here!"

Posey felt herself smiling even more, satisfied that she could confide in her sister’s best friend’s mother to help her out. She was always proud of her daughter Fluttershy for being more assertive and bold throughout the years. This, of course, motivated Posey to do the same, since she felt like she’s still the same old quiet lady from before. She was already best friends with Rainbow Dash’s mother, Windy Whistles, so she seemed like the perfect candidate for helping her be more confident. Of course she did not know Windy’s plan exactly on accomplishing that.

"So just to clarify, your way to make me a bit bolder and less shy-er is to…?"

"For this sort of thing, it's best to do a demonstration.” Windy explained as she carefully stepped out from the pool. “Then you can do what I did. It shouldn't be too hard because if Fluttershy can do it, then you can too!"

A red blush began to cover Posey's face as she dwindled her wings a bit.

"Uh, a demonstration? You mean between you and I?"

"Oh ho ho dear." Windy chuckled before her face grew suspiciously evil.

"I meant a demonstration between myself and your son."

“Hello hello!”

Despite being in the cold waters, Posey felt a sudden surge of embarrassing heat. Not because of the scorching sun but instead it was because of the sight of an aquamarine pegasus happily strutting in sight. Her confidence that she was hopefully building up has seemingly vanished at the appearance of her son.

“Zephyr?!"

“Oh, hey mom!” Zephyr greeted, obliviously waving his hoof at his shocked mother. “Mrs. Dash didn’t tell me you were going to be here. Oh well!”

Windy giggled at seeing Posey try to find the right words to say. “If we’re gonna teach you to be more assertive, we might as well have a good ‘test dummy,’ if you know what I mean...”

“No I don’t!” Zephyr happily responded with a toothy grin. “I was more than happy to join since Mrs. Dash here promised me a date with Rain-”

“I lied about the date.” Windy happily responded with a similar toothy grin. "It was the only way to get your airheaded mind and butt over here."

Like mother, like son, Zephyr’s face morphed into a shocked face similar to his mother’s. “B-b-but I just put on my best cologne for this occasion! It wasn’t cheap either!”

“No need to worry, dear.” Windy reassured the miffed pegasus. “I may not be my daughter but I promise you that you’ll find out where she gets her qualities that you oh-so enjoy!”

Windy eventually returned back to the pool, positioning herself next to Posey. She motioned Zephyr to join in the pool as well. Zephyr pondered on what to do, given how he was basically lied to. Of course, the narcissistic gears in his head began to turn and he wondered if Windy wanted to have fun with him so that she could share the news to Rainbow Dash for a once-in-a-lifetime date!

With his smile returning back into his face, he found himself entering the pool, positioning himself in between Windy and his mother. Posey’s face was still shocked but she remembered before that she entrusted her friend to help her out. She may not like her son being involved but maybe this might be a tough but valuable lesson for her to learn in the end. She shook off the shocked look on her face and did her best to instead let out a smile at both her son and Windy.

“Now then Zephyr.” Windy instructed as she crossed her arms. “If you’re going to have a fun time with me, let’s lay down some rules. You’ll do what I say, no questions. Survive and MAYBE you’ll get that date with my daughter…”

Before the aquamarine pegasus could open his mouth in response, Windy closed it as she let out a firm look. “And when I say you’ll do what I say, that means ANYTHING. And when I say no questions, I will NOT hear one question from your mouth. Got it?”

Zephyr’s eyes shot open as he slowly nodded. His will was strong (in his narcissistic point of view) but his body betrayed him. And just like that, he unintentionally found himself enslaved to the pegasus mare.

“Rainbow Dash was right, you really are that airheaded…” Windy muttered as she swam around Zephyr. “Fine by me. It just means you’ll be fun to play around with. No, I’m not going to help you by the way. I’m only helping your mother.”

Windy winked at Posey. “Don’t worry, this will be worth it in the end!”

The blue pegasus mare turned back to Zephyr. “Turn around.” She commanded.

Zephyr did so without hesitation as he felt his face turning red hot. Windy’s giggles did not help cool that down.

“I’ve always wanted a son.” Windy cooed. “I love my daughter but sometimes I need another man besides my own husband. For the sake of today, I’m going to pretend you’re my son.”

Zephyr whimpered in response. “B-but that means Rainbow will be my sist-”

“SHUT UP.” Windy hissed as she covered Zephyr's mouth. “One important rule in the Dash household is to never interrupt the parents when they’re speaking. Nod if you understand.”

Zephyr nodded, sporting an apologetic look in his eyes.

“Oh, those puppy eyes aren’t going to work for me.” Windy smirked. “Only I can master those puppy eyes. If you’re truly sorry, you’re going to have to prove it to me another way.”

Windy immediately pushed Zephyr to the edge of the pool. Posey felt unsure of what was to happen but the sight of her overly talkative son actually behaving for once seemed to quiet her down. Besides, for some reason, she wanted to see where this was going as her body was starting to feel strangely warm…

“I’m one of those mothers who likes to spank her children for discipline.” Windy explained as she swam to the back of Zephyr. “I did so for Rainbow Dash to make sure she behaved properly. And given how much you annoy my daughter so often, I think somepony needs to discipline you properly…”

Without any time wasted, Windy lifted up her hoof and slammed it into Zephyr’s butt, causing him to shriek in pain. Posey immediately winced at the sight of this. As much as she wanted to scold her friend for hitting her son, she noticed how Zephyr was somewhat confused but also enjoying the moment. Another smack was heard, Zephyr once again shrieked as he felt Windy’s hoof hit his ass. He let out another pleading whimper as he bit his lip to contain his happy moans. Windy proceeded to give another spanking, feeling herself a bit hot in the process. She was more attentive to her friend, who was standing in the water feeling even hotter at the sight of the spanking. One last smack in the butt and eventually Windy let go of Zephyr.

“There. That wasn’t so hard, was it?”

Windy smirked as she saw Zephyr in the water, shivering in pain but also letting out small and enthusiastic gasps. He fared no better than his mother, who was feeling her below area of her body sizzling. Posey’s rational thoughts were slowly being dulled and instead she felt her enraging hormones slowly taking over. Could this be the impending confidence boost that she needed?

“You know,” Windy mumbled as she slowly rubbed Zephyr's butt. “I love my husband but did you and your mother know that we’re both in an open relationship?”

Zephyr let out a surprised grunt while his mother's face continued to hurt from the shock she is enduring from Windy.

“True, it sounds dumb, but we found it exciting and for some reason, it helped my marriage a lot.” Windy said while tracing circles around Zephyr's red bruised butt.

“No, I’m not asking you to be part of that relationship.” Windy grinned, savoring the young pegasus's unhappy groan. “I’m just interested in having fun with you just today.”

“You’re kind of adorable but my daughter goes on about how annoying you are." She continued, turning Zephyr around so that he could see her firm face. "So you’re definitely something I would probably toy around with once in a while.”

“But until then, let’s see if your other qualities make up for your constant annoyance…”

Posey silently watched her friend push Zephyr against the poolside before lowering herself, slightly submerging in the water.

“Am I the first mare I’m giving you a blowjob to?” Windy playfully asked.

Zephyr nodded in response.

"Oh you are LYING! No mare could stand your constant talking, let alone to suck you dry!" She turned to a blushing Posey. "After this, make sure to spank him for lying."

Windy wasted no time grabbing Zephyr's boxers then ripping them off, exposing his erect boner that bounced favorably in front of the mare. She can’t help but to blink in surprise, still not expecting him to be this aroused by this. She just shrugged before glancing up to the stallion whose wings are already stiff.

“No word to my daughter or anypony about this. Also, I don’t care that this is considered incest, given you’re my ‘son’ at the time being. Just shut up and enjoy the ride. You make any annoying chit-chat and I’ll bite off your pecker. Does mommy make herself clear?”

Zephyr nodded in uncharacteristic silence.

“Good.”

After a quick lick of her lips, Windy glomped onto the stiff member. This wasn’t her first rodeo when it comes to sucking but she could tell by his inexperience, overall character, and how he was nearly yelping again, much to her mild dismay, that this is his first blowjob. He probably wanted Rainbow Dash to be his first and that thought made Windy feel even hotter. She didn’t know exactly if it was out of jealousy of him or accomplishment from herself. Either way, she continued to suck on it like a pacifier, making sure to suck it at a specific pace that should build up the load quicker. If this worked with her husband, then it should work for a virgin like Zephyr.

Sure enough, it worked as Zephyr started to bite his lips in complete enjoyment. It was definitely a different experience than masturbating to Rainbow Dash and, despite not being the same mare, still had an amazing time with Windy Whistles instead. Sure enough the tension grew and he felt that familiar slight rumbling in his erection. He accepted that there was no use in holding in it and eventually shot a good load.

Windy’s eyes widened as she felt that “station bazooka juice” splash into her mouth. He may be a virgin but judging by the high trajectory of that white liquid, he was definitely a frequent masturbator. No doubt from using pictures of her daughter. Honestly the idea of him and her daughter was starting to make her a bit sick but thankfully she has a good idea on how to get her mind off of that. After all, she isn’t the only one who’s going to slap and suck him around for today…

"Okay, now for the fun part." Windy gasped, bits of cum dripping from her mouth, as she smiled devilishly at Posey. "I believe it's your turn now. Show me the bold Posey now…"

Posey was absolutely speechless. She had a front row seat to a surprise addition in the form of her son. Her very own son who just got spanked and then sucked on until dry. Yet at this point, she was done feeling shocked. Perhaps it's the blazing heat of summer combined with seeing so much that unintentionally turned her on and left her wet. She saw that her underwear was soaking (not from the pool water) so that was a good enough sign that she was enjoying this.

A sudden jolt of confidence passed through her as her wings turned stiff. Her face turned determined as she decided to show Windy the new and improved Posey. Right now, Zephyr needed to be taught a lesson and then pleasured by his ACTUAL mother this time.

Zephyr’s happy and goofy smile vanished when he found himself pushed against the poolside once again. He grunted as he felt his stomach being squished before glancing behind a bit. He was greeted with the sight of his mother with a firm glare.

“You’ve always been a naughty son.” She hissed. “So it’s about time I stopped spoiling you and actually be a mother for once.”

She raised her hoof up before speaking again. “For every time I spank you, I want you to count every single time.”

“Y-yes Mom.” Zephyr gulped before shaking a bit in fear. “I’m sorry for being a bad son.”’

“You’re not a bad son, sweetie.” Posey cooed. “You just need discipline. Might as well give you some right now.”

*SMACK*

“One!” Zephyr shrieked.

*SMACK*

“Two!” Zephyr yelped as he struggled to keep his composure.

*SMACK*

“Three!” After years of being spoiled and being the airheaded younger son in the family, this sudden discipline from his mother was definitely something he did not expect. Nevertheless, he was in it for the ride and decided to endure it like his mother endured seeing him having fun with Windy.

*SMACK* “Four!” *SMACK* “Five!” *SMACK* “Six!”

Much to his light surprise, the spanking stopped. Yet the fear from being mothered did not end for him.

“As much as I’d want to continue to spank you, dear.” Posey hissed as she turned her son around. “Mommy wants you to make her feel special. And mommy doesn’t care how that happens, you just make your mom feel like she’s the queen of the world.”

“A-anything for you, mom…”

“Perfect.”

Imitating what Windy did, Posey placed her lips around her son’s dick. Even if she had thoughts of hesitation on doing this to her own son, it would have been replaced with thoughts of realization that this is her first time she’s done a blowjob before. She rarely had sex and it was just the traditional type. She did hear from time to time how a blowjob works. Just pretend your mouth is a vagina and that’s it. Posey however made sure to use her tongue to start licking the tip of the member. At least it gave her the taste of what her son tastes like. ‘Tastes like my husband’s,’ she thought to herself, ‘No surprise actually.’

Zephyr was already blinded by lust and the spanking pain. Combined with his occasional stupidity and sure enough he had no opposition to his own mother doing this to him. He actually kind of liked this new mother and not just for the sexual excitement. It was definitely surprising to see her finally be bolder like how his sister ‘grew a pair,’ as he described it. Windy was definitely a better and experienced sucker, but his mother is still something he greatly enjoyed.

Another load was starting to form up despite the large load he ejected into Windy. Posey could feel him starting to shake. She tensed up a bit as she realized he was about to shoot out and her mouth was going to be caught in the crosshairs. She easily shook the uneasy thoughts and instead let out a brave look on her face as she prepared to see if her son tasted like her husband.

Sure enough, she felt a hot surge of semen splash into her mouth. Embarrassingly she only caught a quick second of semen before immediately plopping her mouth out of her son’s penis. She definitely needed more practice but still did well for a beginner, in her own opinion. She was at least able to get a good taste. A bit stronger taste compared to her husband. Strange, not a milder taster?

Zephyr felt his penis dangle with semen coating it. He had a dumb look on his face scarred with lust and tiredness. Despite that, he felt happy over what happened and stopped caring about the fact that he didn’t have his first time with Rainbow Dash. Her mother and his mother did a good enough job.

Windy watched the whole thing with an excited look on her face. Her first time experiencing incest and she actually enjoyed it. Her daughter wouldn’t like it but she wondered about the possibility. She placed a hoof on her vagina as she even began to fantasize it. Her sexual excitement also grew at the thought of finally teaching Posey an important lesson in confidence.

Posey swam to the other side of the pool and put her forelegs behind her head and closed her eyes. Her cum stained lips turned into a smile as she let out a satisfied sigh. One thing’s for sure. Posey felt that the road to being confident like her daughter now doesn’t seem so hard anymore. Of course, for obvious reasons, maybe she shouldn’t let Fluttershy know about this.

Unknownst to the three pegasi, Rarity and Spike had returned from their date a bit earlier than expected. This allowed the unicorn and dragon to drop their jaws at what they had just seen. Both the two voyeurs were sporting shocked looks on their faces (despite Spike being turned on by this and Rarity reminding herself to do the same with her mother and Spike).

Author's Note

My prompt was simple:

Windy Whistles and Mrs. Shy, mommy-domme blowjob.

I don't write a lot of Windy or Mrs. Shy or Zephyr or mommy-domme or incest. Heck, I even don't write a lot these days because of work.

Regardless, it was definitely interesting to finally get some writing creative juices running. I hope you enjoyed this Pillowblast!