Anon bangs Windy Whistles

by Clopficsinthecomments

Rating: mature
Tags: My Little Pony: Friendship is Magic, Human, Anon, Rainbow Dash, Sex
Length: 4421

Anon adds a new notch to his MILF belt.

Rainbow Dash made Anon promise not to hit on her Mom Windy Whistles during their visit to Cloudsdale. Unfortunately, Anon can't help himself and ends up banging RD's spectacularly hot mom.

Made as a short comment-fic to accompany a picture
by ShoutingisFun.

Published 2017-07-03 22:20:06 UTC
Last updated 2017-07-03 22:20:06 UTC

MILF to MIHF

Rainbow dash glowered and sulked in her corner of the hot air balloon's basket. Her forelimbs crossed over one another as she looked at her travelling companion with a suspicious face.

"You promise?"

Anon smirked, "Bluefast, I can't help it... it’s like my special talent. I'd have a cutie mark for MILF smashing, if only my sexy ass could get one. I mean-"

"Anon..." Rainbow dash rubbed her temples to stem the inevitable headache.

Anon continued "-it’s not like I'd ask you to stop flying fast, or whatever your cutie mark means... Stop 'rainbow-clouding'? So how can you expect me to stop my MILF seduction?"

Rainbow zipped over into her fellow-passenger's personal space instantly, grabbing his shirt by the collar and yanking him down to her face level.

"Here's how I can expect that, ANON." She waved her other hoof threateningly in his face. "I can accelerate from 0 - Mach 2 in under 10 seconds flat, so imagine how hard I can drive my hoof through your pie hole if you try to... to... buck my Mom like you already bucked Twilight and Pinkie's moms. This is a mandatory friendship introduction visit ONLY."

Anon swallowed, "Fine, fine, you flying Sanic-wannabe... just don't blame me if the magic of friendship with benefits engulfs your mother's hot, wet, lo-"

"STOP."
====================================Pic occurs here https://derpibooru.org/images/1475524 =============================================

Anon came to in the Dash's well-preserved bedroom at Rainbow Dash's family house. His face hurt like hell. The last thing he had remembers was a blue hoof caving his face in during a nice friendly tea-time discussion and cake eating session.
Staring at the cloud ceiling with a rather revealing poster of a younger Windrider - ('huh, I'd always figured Rainbro was a carpet muncher'), Anon could hear some shouting going on outside the room.

"Mooooom, NO! You don't understand. It’s a big risk. He has this... this... effect. You need to kick his butt out of here!"

"Language young lady! Honestly, I don't remember ever raising you to be the #1 rude host. I can take care of myself very well, thank you very much. Now you get out of here and go take a few laps around Cloudsdale until you cool off." Anon snickered, hearing Windy Whistles take her daughter to task.

"FINE! ANON if you can hear me, if you lay one ho- hand on my MOM you're FINISHED!"

Anon was confounded by how a cloud door could slam so hard as he heard the telltale sonic pop that always accompanied Rainbow leaving in a huff.

The door to Rainbow's room opened with a click as Windy Whistles stepped in and let out a breath.

"Phew. I'm so sorry about that Mr. Anon, I really raised my daughter to be better than that, but she really is my little #1 troublemaker sometimes."

She shook her head slowly as she walked toward Dash's childhood bed and put a hoof on Anon's shoulder. Stroking it with genuine concern, she looked up to Anon's face with a look of worry... and something deeper.

Anon was a bit startled; unless his memory was failing him (which would be perfectly understandable if Dash's hoof had given him significant head trauma), he had no idea why this beautiful mare wasn't treating him like the lewd jerk he was earlier.

He coughed to clear his throat, "Well Dash's Mom, it was a pleasure meeting you and messing with your daughter's head, but I should probably go catch up with her before she throws a sulking fit and I lose my 'friends with benefits' privileges with her."

Anon was serious. The last few months with Rainbro had been great. Hanging out, eating pizza and pranking the stuck-up ponies around Ponyville was fun. Even more fun were the free blowjobs and tumbles in the sheets, in exchange for helping Dash take care of her heats when they came around. As much as he liked to screw with her head, he wanted to keep a good thing going.

Windy Whistles adopted a predatory grin on her face as she slowly stepped up onto the bed and leaned in close to Anon's face as he backed up against the headboard.

"Now now, Mr. Anon. There are a few things that I won't allow in this house, and not abiding by your promises is one of them."

Anon swallowed heavily, he'd seen this script play out before and was worried where this road might lead. The mare's deep indigo eyes stared into his soul as she bore a shit-eating grin that he'd seen on her daughter many a time in the past... must be genetic.

"P-promises?"

Windy snorted and leaned in close to Anon, her muzzle brushing his face while inhaling and exhaling heavily, the hot air of her breath rushing over his mouth. Anon could see her lips part slightly and he thought a kiss was unavoidable... before she turned away quickly, swatting him in the face with her coral tail.

'What a fucking tease,' Anon thought as he watched Windy Whistles slink down between his legs, catching a few flashes of what looked to be a swollen, winking marehood behind her flicking tail.

She curled around and lay in between his legs, smushing her nostrils into his fly and snorting in heavily, as if she were trying to inhale his groin. Finished with her giant sniff, she sighed contentedly and rested her muzzle on the crotch of his jeans, pressing against the outline of his erect dick. She traced her eyes sultrily up his chest before returning to looking deeply into his face.

"I do believe you said, 'fuck like animals'? Now Mrs. Twilight Velvet said something more along the lines of 'insatiable minotaur love-god', but if you end up in between those two points I should be fine..."

Anon slapped his hand against his head in shock. He knew that Velvet and Windy Whistles were friends, but after the vow of silence Twilight Sparkle and her Mom Velvet had made him take post-the incident, he didn't think she would be going around spreading tales of that night.

"Jesus, Velvet told you what we did? Listen Mrs. Windy Whistles, you're a nice mare and all, and I'm a huge asshole... but even I wouldn't do this to Rainbow while I'm dating her... she'd probably tear me in ha-"

Windy nipped at his jeans aggressively and pulled down the zipper on his fly with her teeth quickly. As she wrapped her wings up and around his hips, hooking into the waist of his pants.

"Enough talking, mister. I've been just dripping since you walked in with that smell of yours. Honestly, I don't know how my little Dashie isn't leaving snail trails all over Ponyville with that musk coming off you."

With a powerful flex of her wings, she nearly tore his jeans down to his knees, his cock painfully bouncing off the still buttoned waist before springing up proudly in front of Windy Whistle's muzzle, making her stare cross-eyed at the tip.

(Imbued with the power of all Anons combined when he'd been pulled to Equestria, Anon'd had the pick of all physical attributes of the various Anons online at the time of his transportation. Being the red-hot blooded male he was, he took the biggest dick he could, which left him with an impressive 9 inch penis, with a width a bit smaller than a Coke can. It was not a choice he had regretted yet.)

Windy's muzzle rested on his balls and her wet nose pressed into the base of his shaft as she drew her nose all the way up to his head, inhaling heavily as she went, before she gave his frenulum a little kiss with a contended sigh.

"Holy fuck."

Windy leaned back and took in the entirety of the organ while bumping it adorably with her hoof.

"Interesting shape... not as big as I was worried about when I first saw you, but this will still end up being the #1 largest cock I've ever bucked."

She wiggled the whole shaft with her hoof as she spoke, finishing with a giggle and a lip bite as she watched the cock throb and jerk aggressively.

"Windy, I'm not gonna lie... I'd love to put your face into this bed and see if I can pound you through the mattress... but you're a married mare, what about your husband?"

Windy blushed and scoffed while looking away.

"Bo has had trouble stiffening his wings for years now and I'm a mare with needs. Now shut up and let me get this intoxicating smell into my b-"

As she was explaining her marital infidelity away, she was leaning closer and closer to Anon's dick, her eyes becoming slightly more and more glazed until she closed them as she opened her mouth and engulfed the head of his member.

Anon gripped the sheets and leaned back, groaning. He felt her thick, muscular tongue coil around the head of his dick in powerful swirls, like she was licking an ice cream cone. Sloppy sounds of her swallowing the mixture of her own drool and his juices filled the air. She paused for a moment to open her eyes and look up at him with those big, bright eyes before smiling and smashing her muzzle down into his crotch. Her eyes shut tightly and she focused on the task at hand as her wings gripped his buttocks. He felt the head of his cock bounce off the back of her mouth and then bend back into her throat. She pumped up and down the full length of his cock a few times, her tail flicking back and forth between his legs as she increased her speed. A few times he felt her throat constrict and grip at his dick but she managed to continue breathing through her nostrils as she drove his shaft into her esophagus, literally face fucking herself.

"JESUS! You suck cock better than Pinkie"

Windy paused when she heard this and looked back up at him with a grin. She slammed her face down to his hilt one more time and he could feel her humming as her tongue lashed about at the base of his penis. He felt the telltale tightening in his sack and began to groan, but continued to resist the urge to unload into Dash's mom's throat. Her wings gripped his buttocks even harder, pulling his ass-cheeks slightly apart. Any resistance he was mounting was lost when she tickled his rosebud with a feather, surprising him and causing him to let loose the torrent he'd been holding back.

The ecstatic wave overwhelmed him as he felt pulse after pulse of thick sperm unload into Windy's throat, coating her depths with thick paste. Five, six... seven hot throbs of semen later he unscrewed his eyes and looked up to see the cute little mare being held down by his hands onto his crotch.

He released her and pulled her head up and off his shaft. Her watery eyes met his and she grinned, a thin rope of cum-drool connecting his cockhead and her lower lip.

Annoyed at her seemingly smug superiority, he shifted quickly. Pulling his legs under him he flipped up off his back and grabbed Windy under her armpits. Windy looked surprised to be manhandled so easily as he flipped her onto her back.

She looked up at him in surprise as he pushed her hindlegs apart. The powerful smell of her musk and the heat of her marehood wafted up and hit Anon like a cloud of steam. He was the predator now.

Anon whistled softly as he surveyed his prey. Windy watched Anon staring at her so ravenously and covered her mouth to giggle.

"Alright you just laugh then... it’s time to teach you why Lyra Heartstrings has a finger fetish."

Anon prepared to employ the forbidden fingering technique he had used with hundreds (well... maybe more like a dozen) of mares since arriving in Equestria. Rubbing the winking clit with his thumb to get the engorged marehood lips to part, his slid his index finger into Windy's cunt.

He was instantly surprised at how hot and tight she was. Even more so than her lithe and athletic daughter. But he soon found the landmarks that he always found in each mare he'd been with thus far, regardless of race or body type.

You see, Anon had discovered that when pony mares wink, they do it for one of two reasons:
1. When turned on to part their folds and make penetration more likely while their partner mounts them, or
2. In the throes of orgasm to accept as much cock as possible into their depths.

Once this was accomplished the second half of the wink would occur where the clit would sneak back into its folds and the love tunnel would tighten significantly, either to keep the recently entered cock in place, or to squeeze each last drop of stallion cum out of the shaft as it pumped into the lucky mare.

Now Anon had learned that if he dug his finger up into the roof of the love tunnel where the muscles for the clit were located, he could pinch and pull the clitoris into its 'winking' state and keep it from retracting. All the muscles and nerves of the mare's vagina were linked and the whole organ would go into heavy spasm trying to throb itself open and closed to 'unstick' the clitoris. It usually had spectacular effects.

Trying to do this now, he dug his index finger to form the shape of an OK sign with his thumb on Windy's love button and found the spot he was looking for. Digging the tip of his index finger into the inner edge of the clitoral bulb, he now had the whole bundle of pleasure nerves caught between his thumb and forefinger.

Instantly, Windy squeaked in fear and surprise. He felt her powerful clitoral muscles throb repeatedly, trying to retract her clit, but he wouldn't let go and started rubbing the sensitive hot bulb. Windy squeaked louder and her legs slammed shut around his hand, trying to keep the intruder out, but it was too late.

Squeaking became groans, and groans became screams as her pussy continued to throb harder and more intensely. Anon knew this sequence well... these powerful muscles were never used to being activated so spastically for so long and were already well beyond the point of their exhaustion. He wouldn't let up though, as they continued to fire and pull against him to try to retract the sensitive love bud he was still grinding his thumb into.

Windy's spasms were wracking her whole body now, each denied clitoral retraction and subsequent throb becoming a hip thrust which rippled through her powerful abdominal muscles up into her back and into her wings. Her screaming began to fade into a dazed grunting as her exhausted facial muscles sagged and her eyes lidded, her tongue drooping out of her mouth as she stared blankly with a thousand yard stare.

Anon knew this to be the final stage of progression: Windy was now fully orgasmic, each clench was flooding her body with dopamine and adrenaline as she was surged with the most intense orgasms she'd ever experienced over and over again.

The only wildcard would be whether Windy was or wasn't a gusher... this question was answered almost immediately as her exhausted deeper vaginal muscles relaxed and all the built-up lubricating fluid began to gush out with each slowing throb. Anon's hand, arm, and lower chest was soaked as each gush exploded out like someone unkinking a garden hose... a garden hose running a line of warm, wet, slippery mare-juice.

As the gushes and throbs finally subsided, all the clitoral muscles were now completely filled with ATP and unable to function, so he released his pinch grip. Windy's exhausted clit remained disgorged and her vaginal opening loose and sloppy as no strength was left in her to react to her marehood's freedom from Anon's handiwork.

Anon leaned in to Windy's face which was staring up at the ceiling, her tongue lolling out the side of her mouth like a dog on a hot summer day. He chuckled as she tried vainly to focus on him, one eye responding to her will and somewhat settling on him while the other continued to roll upwards, making her look a little derpy. She tried speaking but sounded like a stammering drunk as her head rolled about on the pillow.

Anon leaned in and sucked her long tongue into his mouth, pulling in close to her muzzle as he french kissed her deeply. The tongue lay dead and exhausted in his mouth, but, with practiced care, he placed her tongue back into her jaw before breaking the kiss and leaning back. Now he got to wear the shit eating grin as he watched her slowly breathe in and out for a few minutes while she recovered.

About 5 minutes later, she stretched slowly, like waking from an amazing nap and looked up at him.

"MMM, un-*huff*...unbelievable"

She rolled onto her belly, craning her neck back to look at him over her shoulder and through her still rock solid outstretched wings.

"Yeah, that sequence usually gets the girls gossiping."

With her orgasm-drunkenly lidded eyes and speech making her giggle, she pushed up her hind-legs and let her tail's dock instinctively flip upward, creating a rustle of her now-musty coral tail hair as it pushed up to reveal her aching cunt. Her muscles had recovered enough to start winking and spurting again, especially now that they were in their traditional position for mating.

"Forget about gossiping! Take me in my wet, hot, marehood, my #1 stud"

Anon didn't hesitate as he scooted off the bed and aligned his dick with her folds. He usually liked to ease his way in, but one of Windy's winks was powerful enough to reach out and engulf part of his cock's head... and as soon as she felt his penis, she pushed back with her powerful limbs trying to slam more of his cock into her cunt.

Immediately he felt the pain of how tight she was. It was a good thing that he'd loosened her up with fingerplay beforehand or she might have enough strength in her vicelike grip to crush his twig. The grasping and clenching nature of the first 2 inches was incredible, as the powerful muscles swirled around his foreskin and frenulum, while he felt her throbbing clit massage the underside of his cock head. His balls felt tingly and wet as he realized she was still sprinkling marecum from her folds with each pulse.

'Such a greedy little mare,' Anon thought. If she wanted to be bred so badly, he would gladly take the reins. Smiling evilly, he reached forward and grabbed a fistful of Windy's short hair, turning her drunken smiling face away from him and pushing it into the mattress, as he had promised earlier.

With a mighty thrust of his hips he pushed all the way into Windy, as roughly as he could. He grimaced slightly as he felt the pain of the tightness constrict his penis and pull his foreskin back painfully.

*PLBBT*

A loud queef drew a chuckle from Anon as Windy squeaked with embarrassment. His large cock had sealed Windy's whistle airtight and pushing all the air out of her depths led to the noisy bodily emission. With the air driven out, though, the suction on his member became as intense as a hoover vacuum as he began to mercilessly pound her marehood.

Windy cried out as he thrust deeper and deeper into her. 7 inches, 8 inches... he was slamming into her cervix over and over as the most intimate part of her body struggled to lengthen and extend itself to accommodate him.

"Unf - unf, mm eas-, easy there! That's - that's tooOoOo OH MAI GAWSH"

He had finally hilted and Windy now felt totally full, both emotionally and physically as she came throatily on his big cock. He really was the largest she'd ever had. Anon knew that with pegasi he had a chance of winning in the size department as they tended to be a bit on the smaller, more aerodynamic size.

He slammed into this mare’s body harder and harder. He used long strokes without fully removing his penis so that the airtight seal would churn her insides into a chaotic, passionate jumble. Stallions would be in, pump a couple times, and done within seconds, and this type of extended and brutal fucking was usually a novel experience for most mares.

He reached forward and slapped her athletic, toned rump just as he felt her quiver on a particularly powerful throb. Like a trigger releasing a dam of pent up passion, she began to shake in orgasm and he felt more sprinkles of mare cum fly out of her already sopping marehood. Her wings began to flap and tremble and he had to tighten his grip on her hips to pull her down and stop her from taking off. Windy groaned loudly and swore vocally for the first time before she opened her mouth and shouted out.

"Harder ANON, rut me harder, RUT ME LIKE A LITTLE FOAL IN HER FIRST HEAT. RUT ME LIKE A DADDY PLOWING HIS LITTLE FILLY. RUT ME DADDY. BUCK MY TIGHT LITTLE FOALHOLE"

Even Anon was a bit shocked to hear Windy, who, throughout the morning, had been a bit on the uptight side, suddenly expose that she had such a filthy mind.

"Holy shit, Windy you've got a mouth on you."

Anon knew he was reaching his limit, as he continued to grind Windy bodily into the bed, her hipbones smacking into his as he now drove into her almost completely downward. He had been pistoning into her for over 15 minutes now and he knew he was going to unload into this mare shortly.

He leaned over her body, wrapping his arms around her chest and arms as he tried to squeeze her as hard as he could with all of his muscles. Her rambling dirty talk tapered off into a contented *squee* as he hugged her with all his might.

He felt his pace slow and he thrust into her once more as deeply as possible while his balls tightened. Turning his head and opening his mouth, he took a bunch of her quivering, sensitive back muscles into his mouth and bit hard as the first thick ropes of cum burst from his dick, deep inside Windy.

The guttural groan from Windy as she felt herself being bred was awesome and wonderful to hear. If anyone had been in the house, or even within a block of the house at the time they would have heard it and known that a mare was getting filled at that moment.

Throb after throb of thick man-semen flooded into Windy, and while it was nowhere near as much as a stallion (ponies would always have Anon beat in that department) her greedy uterus still spasmed and dipped into the pool of cum accumulating at the very depth of her worn out vagina.

Finally, after a few minutes of basking in the sweaty, musky, soaking wet afterglow that was their climax, Anon pulled his half erect penis from Windy's upraised tail end with a squelching pop.

A semen-marecum mixture trickled from her throbbing vaginal opening as she let her aching rear end hit the mattress with a thump and a contented yet exhausted sigh.

Anon began petting her sore back muscles as he snuggled up to her.

"Give me a few minutes, and we'll get started on round 2 my wonderful little MILF. Though I guess it would be 'have fucked', but MIHF doesn't sound as ca-"

Windy's eyes shot open in surprise, and even a little bit of excited fear.

"R-round 2?"

"Technically round 3, as I did blow in your throat rather quickly. But yeah, Sparklebutt's mom was surprised too. God bless my monkey ancestors and their evolutionary reproductive strategy... you and me will be continuing this session... all. afternoon. long."

Anon spoke seductively as he walked two fingers down Windy's belly toward her genitals, his penis already beginning to re-stiffen.

"Oh my..."

=================================================================

Hours later, as the sun began to dip over Cloudsdale, Anon sat back in bed with the covers up to his chest, as he lit a single cigarette. Next to him, Windy Whistles was snuggled up to his chest, her head under his left arm as he idly stroked her messed mane.

All around the room was the aftermath of their passionate day. Covers and sheets knocked to the floor. Dash's childhood trophies strewn about. Puddles, ropes and stains of various fluids on every surface and object. Condoms were sloppily discarded on a wastebasket from when Windy and Anon had tried out more exciting orifices.

Snuggled up against the large man, Windy felt like a college mare again. Every part of her ached in a good way, as she booped the man-stallion who had rutted her into feeling 25 years younger.

"I would tell you that smoking is a filthy habit, but I think you've earned that one, my #1 motherbucker."

"Fuck yeah I'm #1, do I get a medal, or what?"

Windy chuckled and grabbed a nearby gold medal of Rainbow Dash's to put around Anon's neck. In this moment, she wasn't a mom... just a mare... and she woul-

The door burst open as Rainbow Dash did one of her trademark 'no-knock' entrances.

"Anon, you in here...? Listen I'm sorry about this morning I just get overprotective of my m-"

Rainbow progressively slowed her speech as she took in the sight in front of her. First it was all the various chaotic mess, then the unmistakable odor of sex. In this case, the odor hung so thick it may as well have dripped off her.

"D-Dashie!?"

Windy Whistles was snapped back to the present as she realized what she was doing.

"MOM? ANON!?!? AND IN MY CHILDHOOD BED YOU MOTHERBUCKER!? LOOK AT MY BUCKING SHEETS!!!"

Anon put his cigarette out, well aware that it was probably the last he'd ever smoke. A blue blur launched at him amidst a cacophony of screaming.

"SHIT."

Author's Note

Hope you like this first story of a new weekly writing exercise!