Windy Whistles Dragon Cuckold Quest!

by TheOneWithoutAName

Rating: mature
Tags: Dragons, Anthro, Original Character, My Little Pony: Friendship is Magic, Rainbow Dash, Porn, Windy Whistles, Sex, Fetish
Length: 5117

Rainbow's coltfriend, the drake Tamati, decides to visit Windy Whistles for some hot steaming fun.

The drake Tamati has been getting along quite well with Rainbow Dash. Albeit he is insatiable, so naturally he decides to visit his marefriend's mother, Windy Whistles, for some fun.

Hot steaming interspecies sex ensues.

Commissioned by: Tamati

Editor: psker

Cover Art by: kanashiipanda (1309171 on e621.net)

Contains: F/M, Vaginal, Anal, Oral (Deepthroat), Creampie, Maledom, Cuckolding, Rough Sex, Interspecies, Degradation/Humiliation and an Implied Incest Ending!

Featured: 11/14/2023

Published 2023-11-13 21:50:02 UTC
Last updated 2023-11-13 21:50:02 UTC

A Dragon and a MILF

Tamati landed on the cloudy surface with a soft thump.

It was interesting to the tall dragon, as he normally wasn’t used to such pony settlements high in the sky. Sure, he had experiences with cloud homes…and beds, but one cloud home in Ponyville hardly could do an entire cloud metropolis like Cloudsdale justice.

This city was most impressive with its architecture as much as with its large populace that was flocking about. The drake drew some stares, making him smirk a bit. Truth be told, he was vain, but for a good reason.

His dark gray scales with a lighter gray color on his balls, six pack and chest were smooth and well polished. And his muscular, broad shouldered appearance helped too. He was a real beefcake. A snack as some would put it. And he put in a lot of work to keep it up, doing daily work outs and long and fast flights, always challenging his own records and trying to improve himself.

This was what led to him getting acquainted with a certain rainbow colored mare. He was competitive and loved to race, something she did as well and happily challenged him. It was an intense match and while he didn’t win that particular race, he sure felt like a winner as he managed to get between those legs in the end.

Which led to him hanging out with her more, which led to more sex and then noticing a picture of Rainbow’s mom, which was just his type.

She was a bit pouty at first as he wanted to know more about her. Rainbow easily figured out why. Not that hard as Tamati did fuck Fluttershy and quite a lot of Rainbow’s acquaintances, leaving them delirious and laying in puddles of cum. It was obvious, the dragon wanted to do the same with Windy.

Eventually after some coaxing and some more sex, she relented, telling him the address which led to where he was now. The quaint outskirts of the town with a nice little home. The home of Rainbow's parents.

As her father was working at this day and hour, it was very convenient to him. So he didn’t waste any time, walking up and knocking on the door.

“Coming~” a mare called out and already the drake was imagining how melodic those moans would be. Would it be soft like Fluttershy’s? Boisterous like Rainbow? Or would it be measured and passionate like Rarity?

The door swung open, revealing the mare. Nice blue skin, short orange hair, with some cute B-cups, a slim waist, fat thighs and a well rounded ass. She was smaller than the average mare, just like Rainbow, so he towered even more over her than most other mares.

She wore an orange shirt that was unbuttoned at the top with a white undershirt beneath it and some jeans

“Hey there, cutie. Rainbow’s mom, right? I thought I would come for a visit,” he said in a suave seductive tone of voice.

Windy was surprised to say the least…and a bit distracted by his body, eyes naturally zooming over the barely clothed dragon. He was only wearing some black underwear after all. And with how tight it was, it showed off his bulge quite well. Tamati was one that loved to show off after all.

“Oh, you know my daughter?” the surprised mare asked after a moment with a friendly smile.

“Yeah. We are rather close. How about we talk more inside?”

Unsuspecting, Windy happily opened her door to this hunk, inviting him into her home, before she closed the door.

“Name’s Tamati, by the way,” he said, introducing himself as he plopped down on the couch in the living room.

“Windy Whistles. It is nice to get to know a dragon that is close with my daughter. It is only natural that she would befriend a strong dragon of course! Dashie has always been a real overachiever! And I was there for it with my husband, cheering for her on every occasion.”

“She mentioned that. You are very supportive of her in every way possible,” he nodded, while patting the spot on the couch next to him.

The mare hesitated for only a moment, before shrugging and taking the seat. She seemed to be a very naive mare. A real jackpot if the drake had ever seen one.

He laid his arm around her, touching her waist and pulling her closer and against his body. She was a bit surprised by this, but didn’t protest as her eyes met his.

“Dragons seem to really like hugs. I don’t know much about dragon culture, though I don’t mind learning,” she said, getting comfortable against him with a hum. “Dragon bodies are really warm too!”

“That we are. And yeah. We like touching a lot,” he supplied, tightening his grip on her waist and dragging her on one of his strong legs. “Helps that you ponies are so small~”

His hand wandered now to her inner thigh, rubbing along it as the mare drew in a breath.

“I, um, we are. Though Dashie and me are even shorter than the average mare to be fair. It helps her to fly really fast.”

“Not the only thing that squirter is fast at,” he mentioned with a deep rumbling chuckle.

“Squirter?” The MILF inquired, squirming a bit on the drake’s lap, while he deliberately stroked that inner thigh very closely to her twat.

“Let’s just say we are very close. Dragons don’t have such pesky things as being proper or some strange decorum. If I see you and I like your look, I will come to your home and then fuck you.”

A rather blunt approach, especially with how his hand went to her pussy now, squishing his fingers into the fabric of her jeans, making her draw in a sharp gasp.

Her cheeks turned into a bright red as she was stammering a bit.

“I-Is that so. You don’t have things like marriage then?”

“Nope. No pesky paper stuff. If we like someone, we just stay with them and fuck them even more. And guess what? I do like you and Rainbow is very open to how we dragons do things. I sleep with her and I sleep with others.”

“I was a-about to ask. It is important not to hurt our Dashie, though I am married in case you were thinking of doing something.”

“...And? Are you really going to deny Rainbow’s fuck buddy and disappoint her? She thought you were more awesome than this and would have no problem going along with dragon values.”

With the small protest swatted down, Windy hardly had any defense. Her mind was thinking it over and it was easy to see that her own heightening lust as well as her desire to please her daughter were too strong to resist.

His digits pressed into her harder, slightly penetrating the slit even through the fabric, making her mewl with her head pressing against that muscular chest. Her wings were fluttering against her back, before slowly getting erect.

“A wing boner, how cute. Now, how about I show you some more things Rainbow likes about us dragons?”

“Mmmmm…please do.”

Her body was quivering with arousal as his hand went down to his underwear and pulled it down, letting a large dragon cock flop out, which made Windy’s eyes widen in surprise at the size.

Pointed cock head with ridges on the underside and bumps all over it and obviously much longer and thicker than her own husband’s cock. That Tamati knew alone by the way she was drooling.

He made sure to prod into her a bit more, feeling a certain dampness develop between her legs as he did so.

“I-It’s huge and so…shapely,” she finally said, causing Tamati to chuckle.

Dragon dicks were rather pleasurable from what he has been told by many mares. Stallions at best only had to offer a flared tip and a medial ring to scrape along those pink walls, while the bumps and ridges on his entire dick could cover a much larger surface and make any ride that much more fun. It was addicting too from what he has been told and there even was a growing kink built around dragon superiority. Flamed it was called, because dragons were hot blooded creatures and draked didn’t roll off the tongue as well.

“Oh yeah? First time seeing one or did you look into dragon porn porn before?” he asked, stopping his digits from teasing her cunt, only to get a second hand involved and ripping a large hole in those pants. Much to his surprise, she didn’t even wear any underwear.

“I-I have only seen a few videos, but didn’t expect the cocks to really be this big. Maybe an enhancement I thought,” she stammered, whimpering with some embarrassment after those pants were ripped open.

“No enhancements needed, unlike your stallions. And nice to see you are going commando. Rainbow does that too. Like mother like daughter~” he joked, as Windy nodded. “I am so going to pound you two sluts together later. Of course for now, I will have my full focus on you. Let’s hope you little pony can take it~”

The seductive purr made her shudder. Another shudder followed as he actually took his dick in hand and pulled it back and towards her moist cunt, making contact.

“So w-warm…”

“My cum is too. During winter there is nothing better than a hot dragon load in your womb, while you are out and about. You can ask Dash, she can confirm it. Hehe.”

Before Windy could say anything more though, she was distracted as he had gripped her thighs, spreading those legs wide, while he humped into her. The tip and a few inches went in, making her whinny as her pussy was spread wider than it ever had been in her life. And upon the second hump, a few more inches slid into her as he was burying himself ever further into her.

Not even half was in and he was already reaching far deeper than her husband ever had. Her hands slung behind her around his neck, trying to steady herself as a loud obscene moan came from her lips.

“O-OOOOOOH!”

“Loving those bumps and ridges, ey slut?” he asked, long tongue lapping at her cheek, while he continued thrusting into her, getting into a slow but no less strong rhythm that was prying that twat slowly open. He had experience with mares and knew exactly how to drive them wild, angling his shaft every which way to ensure those bumps were very effective in raking along her insides.

More even louder cries followed as her cunt was drenched by her skyrocketing arousal after only a few thrusts. His dick was slipping ever deeper after all, easily reaching that womb of hers and pounding at the entrance of it insistently.

And then after an especially sharp thrust, it pushed in, claiming even that area for himself. A scream followed as the mare’s back arched in a powerful orgasm as she was shaken to her very core. Her eyes rolling up and tongue hanging out far, wings twitching. Truly a lovely sight.

“That’s a good mare, already reaching your limit after we barely even started. This is going to be a long ride, so you better be prepared, I am going to stuff your womb full~”

The mare whined, still able to hear the teasing promise he was making to her. It didn’t sound like a lie and she wasn’t sure if she should feel delighted or worried about it.

Obviously she wouldn’t protest by virtue of not wanting to disappoint her daughter alone, but the fact that she was worried because it simply felt this incredible no doubt helped a bit too.

Already her lust was increasing again with each new full thrust into her, making those draconic balls slap up against her twat with force and a lewd smacking sound. The tip was pushing against her womb, stretching it out with the sheer ferocity of it, as he was being a lot rougher with her now after she had gotten used to his gargantuan size. A size many mares probably only thought their sex toys could have.

“Ah, aaahn, aaaaah!” came her constant screams of pure ecstasy, which was music to Tamati’s ears as his deep voice purred into her ear.

“What? Your husband that much smaller than me? Oh you poor mare. That limp dick cannot even hope to compete with me. A slut like you needs something better than some tiny pony dong.”

For a moment Windy froze at his words, seemingly contemplating how to respond even as her body was still bounced on him. Though considering how she was biting her lip and her eyes rolled up, it was clear what her response was going to be.

“F-Fuck yeeeesh! H-He can’t! This d-dick is shoooooo biiiiiig!”

The drake was standing up while keeping a good grip on her soft thighs. The standing position gave him more leverage, as he was pulling her up, before letting gravity drop her down, while his hips thrust into her with a noisy wet clap. His pace increased.

She squirted again, cumming easily as her pussy only seemed to get more sensitive, the longer he was fucking her.

He decided to walk over to the kitchen counter, slamming her belly first onto it and gripping her tail and mane in his hands, pulling roughly on her, while fucking her like a mere bitch in heat.

“OOOOOOOOOOHHHH~” she squealed, not a word of protest coming over her lips

His entire length sunk into those pliable depths, massaging them thoroughly. Her ass cheeks rippled each time his hips crashed into her, while more of her juices were spraying out.

Hot pants and pleasant cries were echoing around the home.

Tamati then flipped her around, letting go of her mane and her tail in the process, instead opting to grab her orange shirt. He ripped it open, making buttons fly, before stripping her of that piece of clothing and tossing it carelessly aside. Then he also pulled her white undershirt off of her, revealing the cute perky B-cups that were hiding below it.

The nipples were erect showing off their arousal and the dragon grinned at that, before pinching both of those sensitive nubs, causing the mare to squeal in ecstasy.

“Such a nice and sexy body. I like you small tit types. Less cushioning sure, but you sluts are no less sensitive and are quite depraved needy whores in bed,” he told her, pulling and stretching her nipples as she was arching her back, proving his point nicely. “Oh yeah. A lot easier to get into the sack. Rainbow was no different.”

Her ears perked up at that. “N-Now, now, aaaahn! R-Rainbow isn’t easy,” she defended, or as best as she could while her pussy was sending pleasure up her spine from the intense pounding that was happening to her. Tamati however was unimpressed, leaning down and giving her a proper mating press with his body slamming down into hers.

It just made her scream louder, instantly losing the argument as she was cumming time and time again with that massive dick rearranging her insides to be nothing more than a fleshlight for his pleasure.

“I will be the judge of that, slut. Besides, you didn’t even protest then I said you were easy,” he aptly highlighted, large face coming down to meet her own with a grin. It made her blush even deeper.

“It i-is hard to, oooh, dooooo!” she whined, hands going around his broad chests as much as her legs already were, pulling him in more.

“Protesting? I imagine it is for needy whores. And I repeat it to you, Rainbow was no different. Fucked her on the first day I met her. We simply had a race with a bet,” he told her, grin wide as his face was close to hers, hips moving faster.

“B-Bet? IIIIIIIIIIIH!” she squealed, having a hard time to focus anything other than the dick that was pounding her womb into submission.

“Yeah, the winner can ask anything from the loser. Slut was so distracted when I raced her nude, that I managed to win. Or maybe she lost on purpose?” he suggested, a deep chuckle emanating from him. “Fucked her right in public on those clouds above Ponyville as I made her my cumdump for the day. Not that she protested. And believe me, I fucked her everywhere in Ponyville I could think of. Cafe with her face in my crotch under the desk, cinema riding that ponut and of course all of the rooms in her home. Marking her with my seed inside and out.”

The sexual exploits made the mare pant and moan more and more. Just imagining how her own prideful daughter was used in such a degrading manner was so incredibly hot to her. Naturally, all her limbs wrapped around him pulling him closer as she whimpered and cried out, snatch spewing out its juices as she was receiving another mind-shattering climax.

“FUCK! THIS IS SO HOT! AAAAAAAAAAAH!” she cried, vaginal walls trembling in ecstasy from the debaucherous things he had just told her. There was an evil glint in his eyes, body pressing down into the squishy pony harder.

“And now it is your turn,” he simply stated, hips becoming a blur as he was truly slamming into her womb now. No break. No rest. Just him claiming her sopping wet twat for his personal use. Her liquid arousal sprayed from it, staining the table and dripping down below on the floor as her arms and legs hugged him even more tightly.

Windy lost all sense of time, as her brain was flooded again and again by an addictive high, only a hot fat dragon cock can give. Her tongue hang out and she gave a rather undignified expression as he was happily working her over.

And then after Celestia knows how much time had passed, it reached its crescendo. Powerful dragon hips smacking into her a final time, before hot cum erupted inside her. It was so much warmer than a ponies and that in the most pleasant way.

Her needy hole was massaging his length, milking it of every drop as her cervix was filled up to the brim and beyond, belly expanding from the sheer volume of it.

With how much there was, some of it shot out of her twat from the pressure and leaking down her pucker and tail.

The mare was rather exhausted by this panting, her body sweaty from the immense pleasure and strain this intense fucking had given her.

But it wasn’t over.

He flipped her back around and put his arms under her own, before connecting his hands on her neck, putting her in a full nelson. He dragged her body off his cock, making a plopping noise, followed by a wet squelch as a large spurt of cum leaked out. And then in one smooth motion he hoisted her down again, only with the angle this time going for her ass.

It never stood a chance.

Instantly her pucker surrendered to the large pointed tip, as it pried her anal walls open and sank fully into her. The lubrication from her cunt definitely helped, making it a rather smooth ride. At least for the drake. A mare like Windy Whistles that had little experience in that area had it much rougher, though she cried out in delight regardless, the perversion easily overcoming the strain she felt.

Her marehood winked eagerly, as a larger spurt of jizz splattered noisily to the floor, pushed out by the pressure he applied in her ass.

“Nice~ Tight, just the way I like it. But don’t worry, it will gape in time too. And when it does, your mouth is next~” he purred in a promise, not hesitating to start up his thrusts. Her body was dragged up and slammed back down, bouncing on that rod as he was exploring it deeply.

Immobilized as she was, she was little more than a doll. And a sex doll at that as her body was mishandled by the powerful entity. More and more of his spunk shot out from her cunt, making an ever increasing mess, but with how far gone she was, she couldn’t exactly worry about the clean up as of now.

All she could do was scream, tremble and cum. Her pussy lips quivered feeling as sensitive as ever even without a dick directly touching them while her ass seemed to naturally suck this cock in as if it was right where it belonged.

She could feel the comforting hot dragon precum slicking up her asshole more and more, making it squelch noisily as he was going faster and faster with the added lubrication.

It rattled her brain as much as her orifices, she couldn’t tell how many times she was reaching her high. It was a constant feeling, almost as if she was drugged. Only that the drug was a dick too good to be true.

“Look at you. So far gone. Even easier than Rainbow Dash. Then again, that isn’t a fair comparison. She is an athlete, so she does have more endurance,” he concluded, giving a few more thrusts and grunts as his own pleasure was building.

While being weaker both physically and mentally, she was a rather good fuck. Softer so to say which had its own advantages, but just as tight, showing how Rainbow came after her mother in that aspect.

Well, the most striking resemblance is their sluttiness of course. And it is that sluttiness that the drake reveled in.

So he worked that ass over. Making it looser and looser with every hard thrust. Ruining the mare as she was squealing like the needy pig she was.

Her cries were a good motivation to keep hard at her, letting her feel how a real stud fucks sluts like her. The unique shape was really hitting all the sweet spots it could, making her feel it more than any pony dick would ever be able to.

And then after reaching his limit, he gave a possessive deep growl which made the mare shudder in delight, before hilting into her bowels.

Hot ropes of dragon spunk followed which painted her anal walls very much like her pussy had been painted and claimed by him.

Again, the warmth of it was something Windy very much relished in. Something oh so comforting as she wiggled her butt as if trying to coax out just a few drops more.

He gripped her neck then, making her choke as he dragged her twitching body off. Her wings flapped uselessly against him as the shaft slipped out after a moment of struggle. Those ridges really helped to keep it in. That of course also freed her ass up now for more dragon jizz to push out, making the puddle on the floor ever larger.

Tamati then turned her around and plopped her down, back against the kitchen counter she was laying on earlier. She took some large breathes at how roughly she was handled, but didn’t complain. She was way too dazed for that, not to mention that the fluttering of her wings as well as the dopey smile showed very much that she didn’t at all disapprove of it.

“Damn. Could use a bite,” the drake rumbled, heading for the fridge in the kitchen to get himself a snack. He made himself a simple cheese sandwich and toasted it with his fire breath. Then he looked down on his erect dick for a moment and spewed some flames on it as well, sanitizing it after he had plundered the MILFs backdoor. “Perfect and ready now.”

Grabbing a stool he sat down in front of Windy Whistles, powerful thighs spreading open wide to show off his equipment to her, while putting the toast on the counter.

“Get to it, bitch,” he ordered her with a chuckle. The dazed mare understood, sluggishly opening her maw wide, jaw straining as she took the tip in before pushing. Her gag reflex naturally reacted as she shoved the colossal pole down her narrow gullet. Not an easy task, but the mare was aiming to please him.

The cock outline on her neck was obscene, just like the slurping sounds as she bobbed back and forth. This made the dragon hum in appreciation, while he gripped his toast, taking another bite out of it.

“Not too shabby for a pony. Rainbow would be proud,” he announced, hot pre leaking directly into Windy’s stomach. A snack for her that she happily and greedily devoured as she loved the strong tangy taste.

“Oh yeah, would I now?” a new voice was heard as Rainbow entered the kitchen, huffing with her arms crossed.

The prismatic mare was smaller than the average mare, just like her mother with A-cups as well as a slim waist which gave her a very attractive curve to her body. Her thighs were supple, her body toned. The skimpy black microskirt she wore showed off her body nicely, especially with her wearing a thin magenta thong that peaked out at the sides. Her magenta bikini top was just as skimpy, showing off her body oh so well. The navel piercing especially was a nice touch, just like the few studs and rings in her ears.

Tamati gazed over his shoulders at her with a shit eating grin. “Hey there, Rainbow. You took your sweet time. Here I thought you wanted to watch. Or maybe you did sneak some peeks through the window like you did when I was hammering Fluttershy’s loose sloppy cunt?” he inquired, making her blush a bit and avert her eyes.

“A-As if!”

“Ha! You totally did! That is why you are my favorite! You are a real degenerate. Almost as much as Fluttershy. Girls porn and dildo collection is wild!”

The dragon guffawed out a laugh, albeit it turned into a groan with how fervently Windy was bobbing her head on his rod, kissing his crotch passionately each time she met it.

“Oooooh fuck. Your mom is not bad either. Eager little cunt.”

Rainbow then walked up to him, taking a peek down at her mother. Something Tamati happily used as an excuse to grab her cute taut ass to fondle it. Considering the lacking length of the skirt, it was very easy to sneak his hand under it and the thong ensured her bare cheeks were fully accessible.

“D-Dammit. Can never keep your hands off of me.”

“I can’t you are such a fine piece of fuck meat and I know you love the attention~” he teased her, making her grumble. She couldn’t really deny that. Her butt did press against his hand while he was happily squeezing it.

“Just fuck me, you doofus,” she finally said, cute pout on her lips. Tamati chuckled some more, a large hand lifting her up on his lap, even while her mom was still fellating him.

“I will. Just let your mom get another load out of me and then it is your turn. You know I would never neglect my favorite pegasus whore.”

“Hehe, I guess you don’t.”

She puckered her lips, making him chuckle as he gripped the back of her head and smashed it into his own as they started to make out passionately, not even minding the MILF that was working his dick.

The athletic mare slung her arms around his neck, while her legs also locked around his body, humping him. Her lips parted as a clear invitation. Tamati didn’t waste any time sticking his tongue straight in, jamming it into her gullet. His remaining hand went to her right wing, giving the sensitive joints a teasing squeeze.

Rainbow moaned happily which in turn made Windy moan happily as well. There were hearts in her eyes, just like with her daughter.

‘He is definitely going to treat Rainbow very well,’ she thought, seeing the two together like this. ‘This means I have to support them extra hard too!’

With that in mind her mouth was going faster and faster on him, the drake’s hips bucking as he groaned in surprise. He couldn’t stop the floodgates of his climax from bursting open. His rock hard rod throbbed hard, firehosing the mare’s throat.

The dragon's hand pressed harder on the sensitive wing joint of the slutty daughter, causing her to muffledly squeal and shudder against him, a small orgasm washing over her from the sensation that soaked his crotch.

It was then that both lips pulled off. Windy let the shaft flop from her lips, while Rainbow got the tongue pulled out of her throat.

“W-Woah, you going hard at me, bucking tartarus. Try to be more careful with the wings,” Rainbow groaned, flapping the appendage a bit as Tamati let it go.

“Oh please, you don’t last long anyway, though your mom is at fault. She gives head like a pro.”

The grin with which he said that made Rainbow groan in clear exasperation as she banged her head on his chest.

“...Sometimes I really hate you, you know?”

“I know. So…wanna go up to your mom’s room and have a threesome with her?”

She dragged her head back upright just so she could give him a deadpan. All the same though, he was holding that gaze while giving her a wide grin.

“I am not hearing a no, slut~”

Again she grumbled, crossing her arms. “...if you pervert really want to, alright.”

“I find that idea lovely. I even have the crystal recorder up there and ready to record our first threesome together!” Windy chirped up, making her daughter’s face pale in horror.

“N-No! Absolutely not!”

“I think that is an incredible idea Miss Whistles~ Let’s record it in the highest resolution.”

“4k and not a pixel below!”

The rainbow maned mare spread her wings about to take off and flee the scene, but the drake already had gripped both of them, before slinging her over his shoulder like a trophy and following Windy.

“Lead the way!”

“Of course! This will go right into the collection! And while we are at it, how about we have a tour of the collection of Dashies most precious moments? I will be the guide!” the MILF squealed in delight, rushing up the stairs with Tamati following behind, a distressed Rainbow on his shoulder, hitting his back in futility.

“Nooooooooooooooooooooooooooooooooooooooo!”