Anon meets Rainbow's mother

by The_Real_Hog18

Rating: mature
Tags: Human, Anthro, Anon, My Little Pony: Friendship is Magic, Alternate Universe, Rainbow Dash, Comedy, Romance, Porn, Windy Whistles, Sex, Profanity
Length: 10197

Clopfic with Rainbow Dash and Windy Whistles.

Clopfic with Rainbow Dash and Windy Whistles.

Rainbow Dash brings you to meet her parents, only to find a surprise he wasn't ready for

Disclaimer: Anon is 18

Warning: 69 Position, Older Woman Kink, Milf, Mother and Daughter Sharing Boyfriend, Implied Infidelity, Large 'Assets', Tail Pulling, Handjob, Titjob, Blowjob, Buttjob, Footjob through pants, Anal Sex, Vaginal Sex, Breastfeeding, Slight Fingering, Cunninglingus, Balls Deep, Threesome, Slight Cum Inflation, Cum Drenching, Possibly others

Published 2023-02-09 22:30:01 UTC
Last updated 2023-02-21 07:08:28 UTC

Pleasing the Rainbow

Author's Note

FYI, this is not at all connected to my previous story with Button Mash’s mother… unless I change that later. What I’m meaning to say is that the writing at the beginning is gonna be somewhat similar to that though in case you wanna skip to the good part.

Pleasing the Rainbow

Anon had expected to be in a pretty tight spot. The last thing he remembered, he was driving home after picking up his sister from her job, and now the next thing he knew, someone ran a red light and crashed into them. Afterward, they woke up in a strange world full of bipedal horse people... or ponies as they referred to themselves.

At first, he and his sister seemed scared, but as they received a welcoming greeting from these creatures, they started to feel safe. It was more or less thanks to the Princess of Friendship: Twilight Sparkle and the Princesses of the Sun and Moon: Celestia and Luna that they were able to find themselves a home and settle down.

Right now they resided in Ponyville and had settled in pretty quickly. They were sharing a home for now, but they did plan to live in separate houses when they had enough money… err, bits. They easily made friends with the citizens, especially with the members of the Elements of Harmony. Specifically though, Anon was getting pretty close with Rainbow Dash.

Close enough that it is bright for some… private sessions… one that seems to be happening right now.

In the residence of Anon’s home, right in his bedroom, he had the mare’s large rump sitting upon his face as he lapped at her pussy. She was hunching over and licking around his large member like a lollipop while fondling his balls. She took it into her mouth and started bobbing her head for a bit before pulling off.

“Babe, as much as I want to continue doing this, we’re gonna have to cut this short. We have to leave soon.” She warns him.

The human pushed her hips off before regaining air.

“Dashie, you know I’m not one to release quick.” He tells her.

“Hehe, well, I know one way to get you close quickly.”

She crawled off of him, then she set his member between her thick and bubbly asscheeks. She started mashing them together against his member, causing him to flinch as she looked back at him with a smug smirk. The squishiness of her ass caused the man’s balls to twitch at the feeling.

She let out a just as smug laugh as she continued to pleasure her boyfriend’s member while he leaned back. Anon got a little ticked by the look and laugh before looking at her tail, watching it swish back and forth before he decided to grab it and give it a little tug, causing her to yelp and freeze in place. He then sat up and picked her up by her waist before turning and putting her face down on his bed.

“Ugh, no fair! You can’t just-” She yelped again as she felt her ass get smacked.

“All’s fair in love, war, and sex.” He tells her, now smug himself as he grabs her ass and spreads it, revealing her back shoot. “‘Sides, you wanted me to cum faster right?” He says before aligning his tip.

“Fine, you can have this one.” The mare sighed.

Now with her permission, he pushed his member in slightly, then gripped her cheeks by her cutie marks before he continued. Anon groaned and Rainbow grit her teeth while gripping her sheets roughly as she felt her anus begin to spread until she felt him fully enter her and screamed for a second. Anon huffed and took a second to catch his breath and for them to adjust.

“Shit, how are you still so damn tight!?” He says in a bit of pain.

“You said that last time. Just shut up and buck me already!” Rainbow barked back.

Hearing her demand, he reeled his hips back and began thrusting back against hers, listening to her loud moans. She gripped the bedsheets tightly before grabbing the pillow and using it to stifle her voice. Not that her human boyfriend wasn’t dealing with anything different. Her ass seemed to have a vice grip on his member despite hinting this might not have been their first time.

However, that didn’t stop him from pounding her roughly. He squeezed her ass and even reeled it back for a smack, making her squeal into the pillow. Then did it again, watching her fat cheeks jiggle and ripple.

“Buck, don’t you dare stop.” She moaned out.

“I don’t plan to.”

He gripped her ass harder, squeezing it so much that his hands practically disappeared into her fur. He started going faster, letting the room fill with the sounds of her ass slapping against his crotch. Rainbow’s face started to lift from the pillow as she panted, tongue hanging out.

Then her eyes widened as she looked at the clock.

“Crap…” She says before turning to face Anon. “B-Babe… w-we need t-to finish up… we only have so much TIME!” She then screamed as she felt him tug her tail.

That tug caused her to climax and her wings to spread out as her juices sprayed on his thighs. However, he got the idea and went faster as he felt his own climax coming up. He bent over and gripped her hips, slamming into her like a piston.

Then he came to a stop and she felt his cum flooding her bowels. She continued to pant as her ass tightened, milking every last drop it could out of him. Her belly had a small bump form in it before she felt it stop. When it did, she laid her head against the pillow, still trying to catch her breath before she grits her teeth again as she felt him pulling out of her.

Her anus was still clinging to the man’s member which made him grunt a bit before he finally pulled out with a pop, resting it just atop her ass, next to her tail. Then his jizz dripped from her asshole before he shot the remaining onto her back, getting in her mane.

Afterward, he fell next to her, both panting heavily. After she recovered, she finally noticed her mane was soaked.

“Damnit…” She mumbled. “Gonna need a shower before we go anywhere.”

“Yeah… sorry.” Anon says as he sits up. “Think we might need a minute though… maybe an hour.”

“No, we need to get cleaned up now before-AGH!” Rainbow started to say before she felt some of his cum squirt out of her bumhole. “Okay… okay fine.”

They were now in the shower, an hour after recovering. You see, today the man and his marefriend were going to visit her parents so that he could finally get to know them and would see what kind of family he was being brought into. More or less so that they could get off of Rainbow’s back about finding a lover.

Only problem is that he and her have a relationship that’s 20% chill, 20% romance… and 80% bedroom acts. Anon sighed, knowing that he’d have to clean his act up if he was gonna have to go meet them. Last thing he needed was… well anything like being through out of their house and spraying his blood on the pavement.

“Hey-” Rainbow chimed in. “Listen, my parents aren’t strict, so you won’t have to worry about them having high standards or anything. But that doesn’t mean that they’ll excuse you if they catch you fingering me at the dinner table or anything.”

“When have I fingered you in front of anyone?” Anon says, offended.

“Do not act like you didn’t try it when we were visiting Applejack.” She says while poking him in the back.

“That was one time. Besides, you jerked me off once while we were at Twilight’s castle.”

“Okay, point taken. For now though, we need to calm down and not get horny.”

Uh, yeah that’s what I just said.

“Yeah, yeah.” Anon says before turning, seeing Rainbow’s back facing him, but also her C-cup breasts. “So, that means we can’t do… this?” He then reached around and grabbed them, causing her to squeak in shock.

“H-hey quit it!” She says while swatting him away.

“Sorry.”

“Look, we can get freaky later tonight when we’re alone. Okay?”

“Alright, I can wait.”

“Don’t worry.” She says before giving her ass a little spank. “If they leave us alone long enough, maybe we can have some fun. ~”

“You dirty pegasus. ~” He says with a sly smirk.

They both laughed before they got done in the shower and got dressed. Anon was in his own attire while Rainbow wore a t-shirt with her cutie mark on it, putting on a blue jacket with sweatpants that had a rainbow lightning bolt on it and of course red and white sneakers.

As Anon was writing a note for his sister, Rainbow decided to get one last in by spinning him around and pulling him into a kiss. He immediately kissed back, tongues wrestling with each other before they stopped and looked into each other’s eyes.

“Just needed to do that real quick.” She says with smirk.

“Don’t mind in the slightest.” He says back.

With that said, they left the man’s house, before he could say anything, Rainbow got up behind him, picked him up by the armpits and took off into the air at the speed of sound as he yelled. In just mere seconds, they popped through a cloud and stopped in mid-air. Anon’s eyes were wide as he panted a bit.

“Alright, we’re here.” Rainbow says as he shook his head.

When he stopped seeing double, he was able to see that they were in front of a house in the clouds. She flew to the front door and set him down on the mat.

“Don’t ever do that again.” He says, brushing off some clouds. “Seriously, I don’t care how far your parents’ place is, do not do that again.”

Rainbow just laughed before knocking on the door. As she did, Anon looked around and gulped, seeing the clouds around them. While it may have looked safe to the untrained eye, being a human that can fall through them was nerve-racking.

“Hey, dad.” Rainbow says after the door opens.

“Hey, there’s my little girl.” A male stallion at the door says while pulling her head in for a hug and ruffling her mane.

Getting the sight of the pegasus stallion presumed to be her father, his fur was somewhat purplish and his mane and tail had a rainbow pattern that made it obvious where Rainbow got hers from and he was wearing a pair of dress pants with a green button up shirt over a white undershirt.

Upon seeing the human, his eyes widened as his daughter pulled away from him. Anon looked nervous and already had a bad feeling that something must’ve gone wrong.

“Uh… h-hi Mr. Dash. My name is Anon. Nice to meet you.” Anon says while holding his hand out.

The stallion looked at his hand, then back at him. Hesitantly, he reached out and shook his hand.

“Uh… Bow Hothoof.” He introduces himself before letting go, leaning over and whispering to his daughter. “Honestly was expecting him to be freaky.”

“Dad! Don’t be rude.” Rainbow whisper yelled while slapping his arm before laughing awkwardly. “Well, this is my dad. Dad this is my coltfriend… well boyfriend where he’s from, Anon.”

The man waved awkwardly as the stallion waved back with an awkward smile. Then he stepped aside.

“Honey, they’re here!” He called.

As the three went inside, a mare came around the corner, spotting Rainbow, and flew over before pulling her into a tight hug.

“Dashie! I am so happy to see you!” She says in an excited tone.

“Mom!” Rainbow yelled, muffled by her bust.

“Sorry.” Her mother pulled away, allowing her daughter to breathe. “I’m just so happy to see you. It’s been so long.”

“Mom, it’s been a day.”

“I know, but it certainly feels longer. Now, where is the stallion that took my baby’s… heart. Oh my.” The mare slows as she sees the man in the room.

As Anon got to see her mother, he had a slight blush on his face. Orange hair with lighter orange streaks, baby blue fur, wearing an orange button-up shirt, and a yellow skirt. That’s not what made him blush though, what did was her body. Her nice big bust that easily gave her shirt some struggles and outclassed her daughter’s well-endowed body would’ve made anyone drool at the sight.

“Okay, mom, this is my date, Anon. Anon, this is my mom.” Rainbow says.

“H-hi.” The man stammered a bit.

“Hello. I’m Windy Whistles.” She says while waving a bit before recomposing herself. “So, this the… man you were talking about?”

“Yes, he is.” Rainbow explained.

After the introduction, everyone was sitting at the dinner table, Windy joining a moment later after setting down dinner.

“So, uh… I’m sorry. I really don’t know what to say.” Bow states.

“Yeah, eh… that’d make two of us.” Anon speaks up before thinking to himself for a second. “Uh, you into sports?”

“Well, we have actually been to several sporting events. Not much to do after retirement, am I right?” The stallion says.

“Well, I wouldn’t know, I’m not retired.” The man says before the two of them lightly laughed.

“You’re funny, kid.” The stallion says before thinking. “Speaking of which, do you have a job?”

“Oh, I work at Sugar Cube Corner down in Ponyville.”

“Really now? Do you make your own desserts?” Windy asks, curious.

“Oh naw, I suck at making desserts. My sister is good at it though, she helps.” Anon explained.

“Ooh, you have a sister?” The mare became more interested when hearing such.

“Yeah, she and I both arrived Equestria. Everyone’s been kind to us since we arrived.”

“Rainbow sweetie, why didn’t you tell us about him sooner?” Windy asks her daughter.

“To be honest, the whole thing with him being human… I didn’t want to freak you two out.” Rainbow explained.

Anon gave her a sly look, knowing the real reason was that she just didn’t want her parents to be nagging her about being with a boy… either that or something to do with her not wanting to seem girly or something.

“I’m curious though, how did you meet our little Dashie?” Windy asked.

“Ehh, funny story… not really funny to be honest.” Anon states before clearing his throat. “Ya see, me and my sister, arrived in Equestria about a few months ago. We ended up getting picked up by the Elements of Harmony one of them is of course your daughter, and well… not much interesting happened after that.”

“Are you sure? Doesn’t sound like that’d be the case.” The mare continued to ask.

“I mean, we did get some weird looks, but like I said, nothing interesting other than that. Well, at least until we started dating last month.”

“How’d you manage that?” Bow jokingly asked.

“Honey!” Windy says while lightly smacking his arm.

“I’m joking! I’m joking!” He quickly says.

“Should I?” Anon whispered to Rainbow.

“Let me take this.” Rainbow says. “We just had a lot in common. And things… kinda went on from there.”

“Oh, so this was love at first sight?” Windy asked with a smirk.

“IT WASN’T!” Rainbow suddenly shouted, startling everyone with her wings spreading out. “IT WASN’T LOVE AT-! I-I mean-” She started blubbering to herself with her face beat red.

Anon chuckled a bit before slowly pulling her into a hug.

“Alright, alright, it’s okay, it’s okay.” He says while petting her mane as the blubbering slowly ceased.

She started to make puppy whimpers before wrapping her arms around him. Her wings slowly folded as her ears drooped. She sighed happily before snuggling against him… then a snap and flash caught their attention, snapping their eyes wide open.

“Oh, my baby is growing up before our eyes.” Windy says all giddy as she held up a camera.

“MOM! ARE YOU KIDDING ME!” Rainbow shouted, before slamming her hands on the table, then laying her head in her arms while covering herself with her wings as she groaned.

“Hehe, we’re just teasing you, sweetie.” Bow says as she just groaned again.

Anon chuckled before giving her mane a little pet again. As he was pulling back, she reached out and grabbed his hand again, putting it back on her mane, not moving her head in the slightest. He sighed before continuing to pet her mane. Not noticing the stares he was getting from her mother.

Greedy Mother

“You know what, I think this might be a good time to bring it in here. What do ya say, honey?” Bow says while standing up.

“Really? It hasn’t been that long.” Windy asks.

“I know, but I think this guy deserves some.” He says as Rainbow groans into her arms again.

“Wait, wait, deserve some of what?” Anon asked, confused.

“He’s talking about cider.” Rainbow explained, muffled.

“Yeah, I got a couple of bottles. Be back in a minute.” Bow says as he went to the kitchen.

“D-what, wait! I’m only eighteen! I can’t-and he’s already gone.” The man sighed before scratching his head.

“You’re only eighteen?” Windy asked, curious.

“Uh, yeah?” He answered awkwardly.

“Hmm, I see. So my little girl is into younger colts.” Windy says while giving a sly look towards Rainbow who still had her head down, just sighing into her arms.

“Y-yeah, haha.” He awkwardly laughed back.

Of course, Rainbow Dash was a few years older than Anon, but being that the gap was small, it wasn’t a big deal. Then again, cider was basically the equivalent of alcohol in Equestria, and even in another world, he figured he wasn’t old enough to have any kind of drink. Oh well, at least he seemed to be making a good impression on her parents. At least if her dad was going to offer him a drink.

As he heard the clattering and the squeaking of cabinet hinges, he suddenly felt something touching his leg, causing him to jump a bit. It felt like a foot that was stroking up his shin through the fabric of his pants. He turned to Rainbow, finding her head still in her arms, not paying attention.

Confused, he lifted the tablecloth, however, whatever seemed to be rubbing his leg already left. He looked back at his pegasus girlfriend and still no sign of her being the culprit. Then again, she could’ve been putting on an act, but he was a bit miffed that she was being hypocritical. He shook his head, sighing a bit in annoyance.

Then he felt something brush against his knee. He quickly lifted the tablecloth again, only managing to catch a glimpse of the culprit before it fled. However, it didn’t go in the direction of his supposed marefriend. His eyes widened before he turned and saw that she still wasn’t acting up or anything. He then looked forward and there it was.

Her mother: Windy Whistles was giving you an odd stare. At first, he didn’t catch on, but then he jumped as he felt something poke his crotch and looked down. Poking against his crotch was a foot covered in baby-blue fur. That gave him the hint and he knew who was trying to get his attention.

It came to a shock that as a shock to him as he looked up and now Windy was giving him a seductive stare as she rested her cheek in her palm. He blushed bright red, then felt her press her sole against his crotch, causing him to flinch. She was still looking at him with a sly gaze, she knew exactly what she was doing.

He tried not to let her get to him, but he was already feeling his pants begin to tighten around a bulge. Taking a glance over at Rainbow, she seemed to still have her head in her arms. Well, that didn’t help him in the slightest, especially now that he could feel the older mare’s foot start moving again.

His boner pressed against the fabric as the older mare continued stroking it, making it harder with each second. Anon tried to keep himself together. The last thing he needed was to be getting off from his marefriend’s own mother, especially right in front of her.

Just as she started to fiddle with the zipper-

“Hey, sorry!” He heard Bow call out and immediately Windy’s foot disappeared under the table. “I couldn’t find any. Could’ve sworn we had some left.” The stallion then says as he enters and sat back in his seat.

“Yeah, well, I think we can deal with it for tonight.” Rainbow says finally raising her head.

Anon sat, stone/red-faced, silent, and unmoving. He just stared at his boner pressing against the tablecloth. The silence seemed to alert Rainbow as she turned to him.

“You okay, babe?” She asked, slightly concerned.

“Y-yeah, uh…” He answers before looking around. “I-I gotta go to the bathroom.” He then stood up and practically ran off.

“W-wait, Anon!” Rainbow called.

“It’s just down the hall, first door on your right!” Bow says, trying to be helpful.

Anon ran into the bathroom and shut the door, back against the door. He leaned his head against the door before looking back at his boner.

“Great. Just what I needed to deal with today.” He groaned before sliding onto his butt.

This was just great. He was just making it good with his girl’s dad so well that he wanted to share this world’s version of alcohol with him. How would he feel knowing that his wife gave him a footjob without him knowing, let alone the fact it was the guy dating his daughter?

Then, there’s Rainbow. Oh, he knew that she would take it worse if she found out. Sure he hadn’t been with her as long as usual, but he’d hate to see her face if she found out about what happened, much less how she would react.

Then there was a knocking at the door, causing him to flinch.

“Babe, you good in there?” He heard Rainbow’s voice and sighed.

“Y-yeah, just… gonna be in here for a while.” He says, trying to sound convincing.

“Okay well… we’re gonna head out. You gonna be good till then?” She asks.

“Why are they suddenly-?” He mumbled to himself before speaking up. “Yeah, I think I’ll be good.”

“Alright, see you when we get back. Make sure nothing happens to this place.”

“You got it.”

He leaned against the door to listen, hearing the front door open and close. Whatever the reason for her and her parents leaving, it must’ve been a sign from the god of this world. Despite his sins, Anon thought he was granted mercy at a time like this. However, there still was one problem. His boner.

He looked down at his pants, seeing the bulge, begging to be released. While he may have promised Rainbow he wouldn’t do anything dirty in her parents’ house, this was probably the best time for him to take care of it now that he was the only one in the house.

So he stood up, went to the toilet, opened the lid, then unzipped his pants, whipping out his member. With a sigh, he took hold of it and started rubbing himself off as best as he could. He had inhaled deeply as he did so. So far he seemed to only make the problem worse as he only got harder with each stroke.

He was a minute in and again he didn’t make much progress. He mentally cursed out Rainbow’s mother for doing this to him. Then it hit him, maybe he could just imagine Rainbow giving him a hand job.

So he did just that, he imagined her crouching down right in front of him, working her hand around his member. It seemed to be working, at least, it seemed that way to him. He was still going to take a while, and he could only hope the others won’t be back for a long time.

Slowly but surely, he started to feel like he was finally making progress. His imagination seemed to be going wild as he could almost hear her lust-filled moans, feel her furry hand taking over for him, going down to the base, her other hand fondling his balls, and her lovely equine tongue going from the bottom of his shaft right up… to his… tip…

Wait… didn’t Rainbow say that she was… and she couldn’t have… as he began to realize, Anon’s eyes slowly opened widely. Then he looked down and saw that it wasn’t Rainbow rubbing and licking his shaft… it was her mother, staring right up at him with her eyes half closed.

He stared back at her… slowly regaining his sense.

“DAH!” He screamed, jumping back before slipping and falling on his ass. “What the f-Wha… WHAT?!” He shouted. “What are you doing?!”

“Oh, forgive me for not letting you know. I just figured you’d like-” Windy starts to say in a sultry tone.

“Why would I-Dh…” He felt his voice caught in his throat for a moment before gulping. “I-I thought you left with…”

“Not all of us left. I decided to stay.” She says before looking back at his member. “And I think I’m glad I did.”

Seeing her gaze, he covered his crotch, though he could only cover so much of it. It didn’t take long before she removed his hands and continued to stare.

“I gotta say, I was a little shocked by the shape. No sheath, no flathead… I like it. ~” She says before grabbing it and starting to jerk him off again.

“W-wait!” Anon stammered out, face beat red. “You can’t do this!”

“Oh, is something the matter?” She asked, acting oblivious.

“You’re literally my girlfriend’s mom! That should make it obvious from the start!”

“Well, if that’s the case, maybe we can make this our little secret.”

“T-that doesn’t-” Anon stammered.

He again found his voice stuck in his throat as Windy continued rubbing him off. She fondled his balls, he couldn’t bring himself to voice how wrong this was as he was lost in the pleasure of the mare’s handjob. She didn’t seem to care about committing infidelity while her husband and daughter were out; despite knowing such, the man’s member was betraying him.

Then he took a second to look back at her, reexamining her. He recalled her ample bust and began to take note of her lighter freckles and magenta eyes that her daughter inherited. Now that he was getting a different look at her, he couldn’t help but notice how sexy she was and how much of a milf she truly was.

She seemed to take his silence as a good sign and licked his tip, making him tightly close his eyes.

“Let me ask you this.” She says before crawling up until her face was just inches from his. “Have you done this before?”

He breathed heavily, face feeling like it was gonna go up in flames.

“A-a-a few times… s-several actually. Rainbow and I have been… well…” He struggled to get the wording out being more nervous and yet turned on.

“Did she take your first time?” The mare asks, getting the tiniest bit closer while rubbing his member faster.

“Y-yes.”

Hearing this, her smile seemed to grow wider.

“I’m glad to hear that. I wouldn’t want to take that away from my little girl.” She says as she slows down with her rubbing. “That being said though…”

Then she moved back which allowed him to relax a bit before watching her undoing the buttons on her shirt and letting it fall to the floor, revealing her large, what was assumed to be, double E-cup boobs in an orange bra. Then as she reached back, undoing it, it practically popped off her and made them look even bigger as they bounced free, her furless nipples peeking out.

If it were possible, his nose would’ve exploded with blood. She continued to smile before pushing herself up so that her breasts were in his face.

“There’s just so much that a filly can do compared to a mare with experience. ~” She says as she straddles him, placing his cock between her buns. “So…” She then held one of her breasts up to his lips. “Do I have your interest now?”

His boner practically begging for relief, Anon decided to give up trying to resist and gave in. He opened wide and allowed her to place her nipple in his mouth. As soon as he felt her areola against his lips, he sucked like no tomorrow. She giggled lightly before biting her lower lip, taking his hand and placing it on her other breast while placing her own hand on the back of his head.

He could feel her wiggle her hips and her asscheeks rub against his tower as he squeezed and massaged her boob whilst circling his tongue around her nipple on the other. She definitely had a leg up on her daughter in terms of chest size, though, he sure knew where she inherited her bum from.

Of course, he did feel guilty, not just about Rainbow but also her father too, but he also couldn’t help himself. Unfortunately, even he wasn’t the purest being on Earth… or Equestria. He got turned on by many mares in Ponyville and some even flirted with him, even after getting into a relationship with Rainbow.

He of course didn’t give in to them, but Windy catching him off guard and going straight was a different story. After a minute she pushed herself up and pushed his head off of her breast. Anon didn’t know whether to be relieved or be saddened.

“My, you must’ve enjoyed yourself.” She says.

“Sorry, I just… kinda got… a little carried away.” The young man responds.

“Oh, well if you like my boobs so much, let’s see if you can handle them.” She says while shuffling down and spreading her bust, then sandwiching his member between them.

“HOLY-!” Anon bit his lower lip to keep himself from cursing.

Windy started mashing her tits together against the man’s shaft, causing him to shift his head to look at the ceiling breathing a bit more heavily than usual. The soft pillowy skin rubbing around his rod made precum start leaking already, much to the mare’s pleasure. She gave the tip a kiss before licking it, causing it to twitch.

“Naughty, naughty, boy. Getting off this much from an old mare such as myself? ~” She giggled before squeezing them together.

“I-I mean… k-kinda, yes.” Anon stammered out.

“With something this big, I think I know how you got Dashie to fall for you.” She says teasingly.

“W-well, not really. We did the whole process of dating first-!”

Anon cut himself off, stifling a groan. Then his eyes went back to Windy’s, seeing them half-lidded and a dirty smile on her face. Then looking down and seeing her jugs working around his shaft. Then she starts licking around the tip, causing his member to twitch and twitch as his balls began to churn.

Without warning, his rod squirted cum like a fountain between her cleavage. The mare leaned back, closing her eyes, but turned back quickly and opened her mouth wide. Big droplets landed on top of her jugs and dripped down them, same could be said with her face before it stopped. Her mouth was filled to the brim before she closed it, in a single gulp, she opened it again to breathe, revealing nothing left.

“Goodness.” Windy says while wiping some from her eyes. “You sure were pent up.”

“A-actually, that’s the normal amount. At least for me.” Anon says to her.

“Oh, is that right?” She asks as she gains a smirk before getting up close him, cum still dripping from her chin. “Then how about we go somewhere more comfortable?”

“U-uh…” He stammered while leaning back to keep himself from getting touched with any.

“I haven’t had a good bucking in a while and judging by your current state-” She says while turning back to his shaft. “I think I already know your answer.”

He stared at her, she stared back. He thought about what she said and looked back at his standing cock.

“Ya know what, fuck it.”

A night like no other

There was no reason to turn back now, at least for the young human. The day was now reaching sunset. Windy cleaned off the leftover jizz and led Anon to the guest bedroom. After arriving she turned to him and rose his shirt over his head and simply dropped it on the floor. He decided to return the favor and undo her skirt, letting the same happen to it.

“Woah…” He says as he gets the sight of her drenched panties.

The mare hooked her thumbs around the string and pulled them down, revealing her glistening pussy. Seeing it seemed to send more blood to the man’s groin.

“So, Anon, are you ready to show this old mare a good time? ~” She says, still holding up her seductive smirk.

“Hey, you want it, you’ll get it.” He replied back.

The mare sat on the edge of the bed and spread her legs. Anon drooled upon the sight and didn’t hesitate this time, getting on his knees. He started rubbing his fingers against her vulva, prompting satisfying hums from her as his fingertips were stained with her juices.

He removed them and replaced them with his tongue which caused her to twitch a bit, but quickly relax as he continued to lap at her entrance. The salty taste hit his tastebuds which only fueled his need to service her. He reached around her legs, resting them on his shoulders as he grabbed her asscheeks, giving them a nice squeeze, much to her pleasure.

She giggled as he continued to squeeze her cutie-marked flank as if trying to mold them into a different shape. He leaned forward, pressing his lips against her lower ones, getting his tongue between them which made her gasp. She then started to moan loudly as he started licking around the inside of her pussy, getting as far as he could whilst still fondling her flank.

“Oh, yes! Just like that, sweetie.” Windy says while placing a hand on his head.

Anon wasn’t going to lie, the guilt had still yet to fully fade from his mind, but he figured that he might as well enjoy what he’s got while he can. Then his eyes caught the attention of her bud and he got a little dirty idea. Without warning, he let go of one of her asscheeks and reached up to poke it a bit, which made her gasp once more.

He decided to pinch it afterward and that made her eyes widen and arched her back as she gave a small scream and then released gallons of her juices into the man’s mouth. He gulped all that he could before pulling away and coughing as some sprayed on his cheek. After she was done, she collapsed onto the bed and the man simply wiped off the stain on his cheek as best as he could before standing up.

“Hey, you good?” He asked.

“A-am I…” Windy needed a second to catch her breath. “Great Celestia, you…” She panted before squinting a bit. “Hoo, you young ones are certainly energetic.”

“Eh, I’ve had some practice.” He says while scratching his head.

“Is that right?” The mare then laid her back on the mattress. “Care to show this old mare what you’ve practiced? ~” She gave him another sly/seductive smile.

Anon was now granted the sight of both lower holes. He stared for a bit before standing up and taking his cock, aiming it at her vulva at first, but then a thought occurred. He looked down, then changed direction for her lower hole. She rose an eyebrow at first before clenching her jaw as she suddenly felt him start pushing his member into her sphincter.

The man groaned as the familiar tightness was already starting to attempt to restrain his member. He reached under and pulled, hoping to spread her hole to make the entrance easier. He pushed more and harder until he finally manages to get his rod right in, making her wings spread out as she moaned in pain.

Anon had to put his hands on her ass to push himself in until he was at least halfway in. He stopped, both him and the mare needing to catch their breaths. So far, he could definitely confirm where her daughter got her ass from. The familiar feeling, the familiar strain, it was all there.

“Buck… buck… Oh…” Windy moaned.

“Oh damn!” Anon says. ‘Man, still not used to the tightness.’ He then thought to himself. “You good?”

“Yes, just… Celestia, quit keeping me waiting.”

With a shrug, the man started moving his hips back and forth, letting her moans and the sounds of slapping skin echo through the room. Anon was beginning to feel less guilty about what he was doing… well, not exactly, just was having an easier time ignoring it. All his focus was on giving this pegasi mare what she wanted.

The man was groaning a bit as the feeling of her bumhole squeezing his member still felt a bit painful. At first, he wondered if her husband was ever giving that hole any attention, then he remembered how Rainbow seemed virgin-tight no matter how much they did it, so he wondered if this was a trait of her family.

Windy reached up and grabbed his shoulders before moving them to his head and pulling his face between her bust. He stopped thrusting for a second before continuing. Though, he got an idea and lifted her off from the edge of the bed, holding her up before pushing until he was balls-deep in her and continuing to rut her.

“Oh, buck yes! Just like that!” She says while hunching over the man, arms still wrapped around him.

Hearing her moans Anon decided to up his pacing, feeling her ass ripple in his hands and her entrance rubbed against his crotch as her moaning got even louder. Her legs tightened around his waist as he did so. He pulled his head out of her bust, forcing her arms down to his shoulders and catching his breath.

He looked at her wings and another idea came to mind. He removed one of his hands from her ass and reached up, grabbed one, and began stroking it, causing her to squeal. Still keeping his rhythm, he continued to rub her wing, which made her loosen her grip a bit and for her tongue to hang out from the side of her mouth.

Anon didn’t stop there though. He leaned his face into the crook of Windy’s neck, and gently nibbled on it. She moaned between her panting before looking down at the man, then removing his mouth from her neck and slamming his lips against his, much to his shock.

He went with it though and pressed back. He didn’t hesitate to fight her tongue with his own. She had shown that she was more experience, her equine tongue especially having an advantage, but he still overpowered her and she was loving it. The kiss got sloppy and spit coated their lips while still not breaking rhythm with their hips.

Anon had a familiar feeling building up and moved his hips faster. As he did, he could feel her juices spray on his crotch. Her eyes opened and rolled up as he continued to pound her ass into oblivion. One final slam and he fired his seed right into her anus.

She grew a small bump in her belly grew in her belly before the man had come to a stop. After a bit, they pulled their lips away from each other and panted for air before they collapsed on the bed.

“Oh fuck…” Anon moaned through his pants.

He pulled out of her, and as he did, his cum squirted out from her anus. Windy opened her eyes and stared at him, then smiled.

“Not bad.” She giggled. “I haven’t felt that good since I was a young filly.”

“You call yourself old? No old lady has an ass like that.” He says before thinking. “I mean, I haven’t slept with any other older woman here so, I guess I can’t really say that.”

“I see.” The mare says before grunting as she felt her ass squirt his cum again.

“That’s gonna be going on for a while.”

The mare giggled again before sighing. The two lay on the bed for what felt like an eternity… okay it was only a minute, but it felt longer than that. Neither really knew what to say after what they did. Anon looked back at Windy’s boobs and seemed to fall into a trance as he stared at them.

“You want another taste? ~” She offered while cupping one of them.

Well, that was an offer he definitely wasn’t gonna pass up. He leaned down and reached just to suck it until something out of the corner of his eye caught his attention. Then his eyes widened in fear. Standing right in the open door was the speedy pegasus Rainbow Dash, eyes also widened, looking mortified.

Seeing the look on the man’s face, Windy turned and saw her daughter looking at them. Slowly, Rainbow’s mortified face turned to rage.

“What…” She says while gripping the knob roughly. “The…” She then clenched her fist tightly. “FUCK!” She was so angry that she spouted out a curse from your world.

“Uh… uh…” Anon stammered before he shot up from the bed. “Wait, wait hold! It’s not what it looks-AGH! I-I mean, I guess i-it is what it, b-but-”

“Oh!” Rainbow dashed up to him, getting right in his face. “Don’t even try to worm your flank out of this. What, my small boobs ain’t good enough for you so you go after my mom’s? Especially MY MOM!”

Anon didn’t have any way to defend himself. A scene like this is a scene that’d put him past his redemption. Any redemption really.

“And don’t get me started on you!” She then pointed at her mother. “Out of all the colts and stallions, you decide to buck my boyfriend?!”

“I’m sorry Dashie, but well… can you blame me?” Windy says while pointing at the man’s member.

“Oh. My. BUCKING CELESTIA!” Rainbow screamed before stomping back and forth while muttering to herself.

“L-look, I’m sorry, I really am. I just…” Anon trailed off before sighing. “I’m sorry, I don’t know if you’ll forgive me or not, but I-I didn’t…” He looked back at the older mare. “Listen, Mrs. Whistles, I don’t want to cause problems between you, your husband, or your daughter-”

“Wait.” Rainbow says as her anger was suddenly replaced with puzzlement. “Say that first part again?”

“Uh… I was saying that I don’t want to cause trouble between her, your father, and you?” He says, mirroring her puzzlement.

“...” Rainbow stared for a moment before glaring at her mother. “You didn’t tell him?”

“Mmm, might’ve slipped my mind.” Windy says with a sly smirk.

“... What?” Anon says, now more confused as Rainbow groaned.

“Babe… My parents are in an open relationship.” She tells him.

“... Again, what?” He says, now more astonished than ever.

“Ya know, like… having multiple partners.”

Anon still looked dumbfounded but started to understand.

“Oh…” He says to himself before looking back at Windy. “But… shouldn’t I… not count since I’m dating your daughter?”

“Oh, it’s really not any trouble dear.” She says while waving.

Well, so much for feeling guilty for fucking her behind her husband’s back.

Rainbow glared back at the man, then grabbed his arm in a tight grip before dragging him out of the guest bedroom. She led him down the hall, naked with his dangling pillar swinging about. She stopped in front of one of the rooms, pushing through the door, dragging him in with her, and locking them in.

“Rainbow, I’m sorry. I won’t-” The man tried to say.

He was thrown onto the bed before he could finish. Next thing he knew, he heard some wooshing, then the rattling of chains, then he looked up, seeing his hands in handcuffs, trapping him to the bedframe.

“Shut it with the ‘sorry’. You wanna make up for it? Stay where you are.” She scolded before she took out a remote. “From this point on, you’re a dildo for the rest of the night.”

As she pressed the button, Anon yelped as he suddenly felt vibrations around his shaft. He looked down and his eyes widened. She had a vibrating-dickring at the base of his member, already causing it to rise.

“Like I said, keep your mouth shut.” Rainbow says as her clothes were dropped to the floor and she was left naked, still looking annoyed.

The tone she spoke in alone sent shivers down his spine. She got on top of him, placing her hands on his chest before scouting back until his shaft was between her jiggling asscheeks. She continued to stare down at him with an even smile before wiggling her hips and letting her lower cheeks smack around his tower to get him hard enough.

Anon was panting and moaning. He was still sensitive after just climaxing earlier and her assjob along with the vibrator made it impossible for him to hold back another one. He kept his mouth shut though, believing this to be karma. He expected Rainbow to be more pissed at him, but if he had to go through this torture to keep his girlfriend from leaving him, he would go through it.

“You still thinking of my mom now?” Rainbow asked him.

“N-no.” Anon stammered out.

“Are you thinking of bucking my mom?!”

“No! No, I’m not!”

“Good. Now shut up and lay there like the toy you are.” She then says with an angry smile.

This was something new to Anon. There were usually days where he’d take the lead and other days where she’d take it, but this whole sadistic and dominant attitude was new to him. Then again, it wasn’t necessarily an unwelcomed thing to him.

She leaned over him and started grinding against him, wrapping her tail around his member, and began pumping his member to add to the torture. So far, it was starting to get the better of him and he could already an orgasm starting to reach. However, he suddenly felt a slight bit of relief as the vibrations stopped.

“Really, Rainbow. I didn’t take you for this.” He heard as he and the rainbow pegasi looked back to see her mother standing there, holding the ring. “To be treating your lover in such a manner.”

Rainbow glared at Windy before speaking up. “You have no room to talk!”

“Yes, I guess, but even so, I believe this was a little far.”

“Oh, I could’ve gone a whole lot farther than this. This is mercy.”

“Is that right?” Windy says before tossing the ring onto the ground. “Of all the things I expected, I didn’t expect this, especially in your old room of all places.”

“This is your old bedroom?” Anon asked before getting a stern glare from the rainbow mare.

“Look at this, you’ve already gotten him all wild up again.” Windy says.

“Mom, get out. I’m not about to let you overthrow my spot as his… as his…” Rainbow trailed off, trying to think. “Well, whatever. I’m gonna show him that I’m a better bucker than you.”

Hearing that, something seemed to snap within the older mare’s head.

“Dashie, care to repeat that?” She asked with a dark look on her face.

“You heard me. Besides, I’ve got the ass you don’t got any more.” Rainbow says back.

Anon’s eyes were now wide, not from the attempted torment from his marefriend, but the fact that she was attempting to roast her own mother despite the current scene.

“Is that right?” Windy asked before sighing, then nodding her head. “Okay then.”

The man still didn’t catch on before the older mare turned around. She then both the rainbow mare and the man’s shock, something completely unexpected, and mashed her ass against her daughter’s and his member.

“Shit!” Anon yelled.

“What the bu-?! MOM!? What are you doing?!” Rainbow practically screamed.

“Sweetie, you wouldn’t have that ass if it weren’t for me. You may still be young, but I’ve still got more experience.” Windy says before pushing her cheeks against her daughter’s, causing Anon to grunt. “So, as much as I love you, I’m not about to let such slander slide.”

‘What?! Where did the talk about how to treat your boyfriend go?’ Anon thought to himself, still in disbelief.

“You can’t just but in! This is supposed to be our time!” Rainbow yelled as she tried to shove her mother back with her ass.

“Well, you should’ve thought of that before challenging your mother.” Windy says doing the same.

“This is supposed to be a punishment, you can’t just turn it into a reward.”

“Too bad. I’m not going anywhere.”

The two continued to try and shove each other off, much to Anon’s pleasure as his member was constantly being squished back and forth between their asses. While they were arguing, he was panting and breathing heavily. If he wasn’t already close before he sure as hell was now.

Then, his balls churned, his shaft twitched and then, it happened. His member fired cum between their asscheeks, stopping their bickering as their tails, wings, and backs got covered in it. He lay in bed, wrists still cuffed to the bed frame, panting for air and face so hot it felt like he would’ve melted on the spot.

“So, guess that makes us tied now?” Windy asked.

“Yeah right, that was was all me. I know what my boyfriend likes, and so does…” Rainbow began to say smugly.

But then as she looked back at Anon, seeing his eyes squinted and his breathing still heavy. Something seemed to smack her back to her senses.

“Oh, shit, shit! Anon!” She says as she quickly got off and uncuffed him then checks his face. “Are you okay?” She asked, not getting an answer. “Oh, shit, I’m sorry.”

It was like night and day that she suddenly switched back to being the loyal and caring marefriend she was. Anon coughed before clearing his throat and looking back at her.

“C-can I… just… get some water.” He asked, still panting.

“Right, got it.” She then sped out of the room before coming back with a cup of water. “Here.”

He took it and started to drink, stopping for a few moments to catch his breath. He continued until the cup was empty. Afterward, he started to breathe more steadily, much to the rainbow mare’s relief.

“Anon, I’m so sorry, I am so sorry! I-I didn’t mean to go this far-” Rainbow continued to speak a million words per second.

“Rainbow!” Anon says, with a hand up. “It’s okay…” He sighed before making eye contact with her, having finally cooled down. “It honestly wasn’t that bad.” He says while giving her a reassuring smile.

The mare sighed before lunging at him, pulling him into a hug. He returned the hug… in spite of his arms getting covered in his own jizz in the process. He was still a little caught off guard by her sudden shift in personality but decided to be the caring boyfriend he was known for.

“Oh, you two are just adorable.” Windy says in a cheery tone.

“Mom, get out.” Rainbow groaned, not moving her head from the man’s cheek.

“Alright, alright. But…” The older mare was about to leave before saying- “Would you mind if I have at least one more turn with him?”

“Are you serious right now?”

“Just one more then I’ll be done.”

Rainbow glared at her, then looked back at her boyfriend, then sighed.

“What do you think?” She asked.

“Uh… if you don’t want me to I won’t.” Anon tells her before closing her eyes to think.

“Wait till my turn is over.” She says before pushing herself up and looking back. “You still hard?”

“Uh… well, after that first session, I uh…”

“Alright, let’s do this.”

Rainbow lifted her hips and pushed her pussy on his member, moaning as it was going in slowly. However, despite the restrictions, he managed to slip in.

After a moment, she started bouncing on him, letting her moans echo through the room. With his hands free, he grabbed her hips to assist her in doing so. Yes, it was tight, but he still decided to push past it.

The rainbow mare leaned down and captured his lips, immediately shoving her tongue into his mouth, entangling it with his own. He kissed back, returning the attention. She then moved her hands down and began feeling up his body, brushing her hands up from his abs to his chest, then up to his face, holding him in place.

Through the window, the sky had darkened as the stars and moon came out. Anon reached and gripped Rainbow’s ass and upped the speed of his thrusting, making her moan into his mouth. He squeezed her pillowy asscheeks whilst keeping rhythm, her tail swishing around while her wings spread and started to lightly flap.

Despite the scene, Windy was watching with a proud smile as she watched her daughter make love with this man. Although, while she was in awe by the sight, it was starting to get to her a little. She placed a hand over her entrance, which still had not been penetrated for the night, and began to rub her outer lips.

The two eventually separated to catch their breaths, panting with a string of saliva connecting their lips. They stared into each other’s eyes.

“You know I love you, Rainbow.” Anon says to her.

“I-I know.” Rainbow says between her moans.

He removed his hands and cupped her cheeks before reconnecting their lips and going back to battling with tongues. Then their hips started going faster again and sure enough, she came, spraying her juices all over his crotch, then he came, shooting his seed into her cavern.

They separated again and Rainbow fell to the side, panting along with her lover who was still cumming inside her and her belly began to slowly expand. It became big enough to look like she was halfway through pregnancy before it stopped and his member slipped out of her entrance, allowing what remaining semen to flow out.

After a bit, they stared into each other’s eyes. Rainbow smiled and snuggled against him.

“You dummy.” She laughed.

Anon didn’t say anything and just hugged back. That was until the sound of throat clearing caught their attention. Windy gave a little wave as her daughter groaned.

“Okay.” The rainbow mare says.

“By the way, should I be expecting grandbabies sometime soon?” The older mare asked.

“Nah, from what I hear, we can’t crossbreed thanks to genetics.”

Hearing that, her mother’s ears dropped. She seemed saddened by the idea that she won’t be a grandma, but then again, it also excited her as she didn’t believe she needed protection.

The two separated, Rainbow Dash lying close to the edge of the bed as Anon got up. Windy then laid her back on the bed, spreading her legs out. The man got on the bed in front of her, and aligned his member with her vulva before taking her hips pushing it into her. Like her daughter, there was some restaint, she moaned at the feeling, before he was fully in her.

“Yeesh, I will never understand how ponies can remain so tight.” He huffed.

“Just get on with it already.” Rainbow says, a bit annoyed.

Anon looked at her mother who seemed to be indifferent about the whole thing before he started thrusting repeatedly. She gasped at first before smiling as the man was now rutting her. Problem is that he was now extra sensitive from past four sessions, so he didn’t know how longer he’d last this time. None the less, it was clear that the older mare still enjoyed.

Rainbow turned around to not look, though it was clear that she could still hear. Anon looked at her, feeling a bit bad, however, he was taken out of that thought when Windy reached up and pulled him down to her breasts while wrapping her legs around his waist.

“You haven’t given these attention in a while. How about you treat them to such? ~” She says, seductively.

He wasn’t dittered and took ahold of her breasts and started sucking on one while sucking the other. Her moans had increased along with her grip on not only her arms and legs, but her pussy.

As he was bucking his hips, he thought back to all that had happened. One second that he was going to visit Rainbow Dash’s parents, next second, he got a titty fuck from her mother, fucked her in the ass while making out with her, then got a double buttjob from both of them, fucked Rainbow in her childhood bed, and now was doing the same to her mother.

Anthro or not, this a dream most people would kill for. And he didn’t think he’d have to worry about the man of the house as her parents were said to be in an open relationship. Damn was he a lucky, especially for someone who was literally eighteen.

It was only so much longer before he could feel his end coming up. He moved his hips faster, and swapped breasts, sucking on the other. After about another minute, her head leaned back and she let out the loudest moan she could as she came on him and he came in her, filling her with whatever was he had left.

It was long before her belly began to grow and was now also looking as though she was halfway through pregnancy as well before he was done. He pulled out of her and heaved before falling onto the bed between the two, panting as his tower fell limp.

“Oh…” He huffed before wiping his forehead. “That was… something.”

“T-that was amazing.” Windy moaned out. “You and Bow… b-both of you… are the best.”

To that, Anon sighed before turning away. Rainbow then laid by his side, wrapping her arms around him, hugging him.

“So, how do you feel?” She asked him with a smile.

“I… feel like I’m gonna need a week before doing anything sex related?” He smiled back at her as she laughed.

“Yeah, figures.”

The two then gave each other a short yet passionate kiss before they stared into each other’s eyes… then the moment got brushed to the side as Windy scooted up and took his other side.

“I hope this doesn’t turn into a one time thing. I’d love to have you and my husband take me at the same time.” She says.

“Ugh… mom…” Rainbow groaned with her face in her hand as her mother laughed.

“Still though.” Windy says. “I’m glad that my baby has found someone to love her in such a manner. You better keep her satisfied now.” She says before kissing him on the cheek as her daughter rolled her eyes.

“Right, but I’m still the bigger priority.” The rainbow mare asked.

“Of course you are. Don’t worry.” Anon says before hugging both of them closely.

Rainbow blushed before smiling as she snuggled up against him. Well, now he had two mares he could bang without trouble or even the worry about them getting pregnant… well, that was what you thought anyway, but… if only they knew to play safe-

“Wait, Rainbow, I got just one question.” Anon asked as his marefriend looked up at him. “Where is your dad?”

“Huh?” She didn’t catch on at first, but then realized. “Oh right. Ya see, he wanted to see where you were living and I decided to take him over to your place. I got to introduce him to your sister and as we were leaving he decided to go to the bar.”

“Is that right now?” Windy asked before sighing. “Guess he couldn’t wait for cider. Leave him be. I’m sure he’ll be back at some point.”

Author's Note

AHA! Yeah, little hint… he didn’t go to a bar.