David and the Shys

by Holocron

Rating: mature
Tags: Anthro, Profanity, My Little Pony: Friendship is Magic, Alternate Universe, Human, Other, Romance, Original Character, Porn, Fetish, Fluttershy, Sex
Length: 4637

David the Human has a lovely time with Fluttershy and Posey Shy, in ways he never expected with such beauties.

FEATURED February 11 - 13 2025

Living in Equestria, David is among many who have decided to live in such a wonderous place. While here, he has met many amazing ponies, but has developed a special relationship with the resident sweet and timid mare, Fluttershy. But she wasn't the only attractive mare interested in him. Posey Shy, her mother, has been in a major dry spell with her husband, and has been considering a little more excitement in her life. So with the mare to set her mum up with her friend, David was in for a rather intense, rather passionate time.

Characters are 18+
Derpibooru: 2625333
The commissioner wishes to remain Anonymous.

Published 2025-02-11 04:20:02 UTC
Last updated 2025-02-11 04:20:02 UTC

Curvy, but not that Shy

Walking up in the morning, David, one of many humans who have chosen to move to Equestria, sat up on his bed with a smile. Today was the day. Getting out of bed, he cleaned himself up, and ate a nice breakfast. All the while, his mind was fixed on the mare he was expecting. Posey Shy, a beautiful, loving mare from Cloudsdale, was to come over today for a lovely date. When he first moved to Equestria, one of the first ponies David befriended was Fluttershy, and while she was far more into humans than anyone would’ve expected, she told him that her mother was currently interested in dating again since her father hadn’t shown any interest in her in years.

Though they haven’t fully met in person yet, from what Fluttershy told him, her mother was very eager to meet him. The sound of the doorbell roused him from his thoughts, and he all but leapt from his chair in excitement as he rushed over to the door. Looking out the peephole he got a good look at the mare. She was gorgeous. Posey Shy was such an adorable, alluring, and seductive looking milf mare. David could see very easily where Fluttershy got her own sexy features from, and he hoped she was everything like her daughter. For a second, he considered what to say to her, how to make a good first impression. But after a second or so, he decided on his approach.

“Yes, hello?” David called out, slowly opening the door as he pretended not to know who was there. But once the door was fully opened and he looked at Posey, he smirked at her in a suave manner. “Hello, gorgeous. To what do I owe the pleasure?”

Now that the door was open, David could see that Posey’s body was so stunning. She was wearing some heavy looking clothes, something to cover up her features, similar to that of Fluttershy. But if she was anything like her daughter, the human could just tell Posey probably had some large breasts, delicious curves, and a sexy ass. Swallowing a little, he didn’t want her to catch him staring, but part of him wondered what she would look like without all those clothes off her body. Thankfully, the mare didn’t seem to notice his staring, and seemed to be shivering in some pleasure from the previous compliment.

“Oh my, you’re just as charming as she said.” Posey giggled with a blush on her face. “Good morning, I’m Posey Shy. My daughter, Fluttershy, told me all about you.”

“Good things I hope.” David said, standing to the side. “Please, come in, come in.” The mare walked in, swaying her luscious flank a little as she stepped. He wondered if this was just how she normally walked, or if she was treating him. “So I know it’s a little early, but what did you have in-” Before he could answer, Posey stripped from her heavy clothes, revealing an exceptionally tight looking one-piece, purple leotard.

David couldn’t nearly fall over from the sight before him. Fluttershy’s body was something out of a perverted dream, but Posey’s body was like something out of a pornographer’s prized collection. Her breasts were a little bigger than her daughter’s though they seemed to have drooped a little, yet were still perky enough in her one-piece, with the fainted wet spots. Was she still lactating, even though she hadn’t had children in years? Though the term ‘milf’ easily applied to this, it was too soft a word to describe how so drop dead sexy she was, all with a curvaceous bubble butt that bounced a little, even as she stood there.

“You like? Fluttershy told me you liked mares who get to the point.” Posey cooed, fluttering her eyes at the human. “And I was hoping you and I could get to know each other as soon as possible.” She paused to let him take in the look of her sexy body, and she couldn’t deny that such a fine, young man being so into her was getting her pretty hot and bothered. “Or would you prefer right here, right now?”

“A-a-a-as tempting as that is, I believe the bedroom would be better.” David said, stuttering for a moment as he was struggling to compose himself. Walking over to her, he decided to try and swoon her a little. Reaching down, he effortlessly hoisted her up, carrying her like a newly-wedded bride through the archway. He wasn’t the most in shape human in Equestria, but ponies were generally light. “Now then, shall we?” Posey cooed as she was carried into his room.

David’s room was pretty modest, almost minimalistic. But this was because the influx of humans into Equestria was still very small, and so there were not a lot of things that could work for them yet. But David didn’t mind, he had few treasured possessions, and that’s all that mattered. Though once he was in his room, he realized something that Posey’s hot ass, milf body distracted him from; his large body pillow. It wasn’t so much that he had a body pillow, but rather what was on it. It was a beautifully drawn image of Fluttershy, her seductive form held in by a very tight one-piece swimsuit that was squeezing against her tits and ass. As soon as David saw this, he nearly dropped the mare, but thankfully held her up.

“Oh my, looks like you’re much closer to my daughter than she told me.” Posey giggled, cooing as she looked up at the nervous look on David’s face. Reaching up, she gently rubbed her hand across his cheek, making his body tingle. “There’s nothing to worry about, I don’t mind. But…” Leaning up, she got close enough to whisper seductively in his ear. “I can be your body pillow, if you want.” David was panting a little, his heart was hammering in his chest, and the way her tits were pressing against his own chest felt really, really good.

Losing a little grip on her, David dropped Posey on the bed, watching her voluptuous form bounce on her bed. In that momentary distraction, she reached up, grabbing at the human, she pulled him onto the bed with her, making him land on her. Once he was on her, she giggled, reaching up, pulling him close to start making out with him again, pushing her fat tits against his chest as she moaned in his mouth. Losing himself into the pleasure, David decided not to think about it, and just enjoyed feeling this slutty, seductive milf in his bed. Reaching down, he groped at her chest, marveling at how soft she was. His fingers were practically sinking into the pudding-like consistency of her tits.

“You can go rough…if you want…” Posey moaned, fluttering her eyes at him. “I know I look delicate…but I can take it…” Leaning up, she whispered again in his ear. “Come on…I want you to fuck me like a dirty, little whore.”

David’s cock nearly exploded out from his pants at the mare’s words. She giggled playfully as she reached down, gently rubbing along the bulge that throbbed between his legs. Not wanting to wait, she skillfully undid his pants, letting out this beast of a human cock meat. Unlike ponies, who were thick, long, and blunt at the end, human dicks were a little smaller, with rounder cockheads, but still no less desirable by mares. Cooing, Posey could almost feel David’s heartbeat through this cock, and reached down with her other hand to slowly move aside her leotard, showing off her puffy, soaking, needy pussy.

The alluring, sweet scent of this warmth was too much. David was practically drooling as this living wet dream of a mare was begging for him to fuck her. Swallowing a little, he carefully lined up his cockhead to her pussy lips, and as soon as the two ends kissed, something in David burst out of him. He instinctively rammed himself into her pussy, nearly bottoming out in her soft, warm, soaking tightness. Posey moaned out from feeling her insides being filled by this dick. It felt so good, and pulled him back into not only making out harder, but shoved her tongue in his mouth, embracing his as she felt as though she was going to cum just from the way he rammed himself into her.

David’s head was spinning, the way Posey was squeezing him, milking every inch of his dick length as he was just hammering faster and faster. So much so, the bed was shaking, knocking over the Fluttershy body pillow, giving the milf mare more room to be his fuckable body pillow. The mare couldn’t be happier, she was so grateful that her daughter arranged this, but it was clear that David wasn’t going to be able to settle down after this. His cock was so big, so meaty as it was skillfully rubbing along all her most sweet and sensitive spots. The pleasure was rippling throughout her body, and the more he fucked into her, the more her tits were bouncing. Grabbing at them again, the human’s fingers sank more into them, feeling her hard, plump nipples between his fingers.

“So good…keep going…you feel so good…inside me…” Posey moaned, feeling as if she was going to cum at any moment. “My…my husband never had this much passion. Please, fuck me harder. Make me all yours. Make me your slutty fleshlight!”

Her words were just so intense, and the way they slinked into his ear like an arousing sweetness only further addled his senses, pushing him less of any conscious thoughts, and more so just the primal urges to fuck and breed this mare. Whether the two could even conceive a child was not yet known, but Posey’s insides were craving David’s hot seed. She needed to feel every ounce of this hot spunk flooding every inch of her sweet and loving insides. Her fertile womb needed to feel warm, virile cum inside her. Even if she couldn’t get pregnant from him, the sensation of what it would be like to have a hot and filling creampie inside her was driving her into a frenzy of orgasmic bliss.

David too wasn’t going to last much longer either. Though he was humping into the mare with the reckless abandon of a savage beast, he was making out with her, holding her close to him, tugging and teasing at her tits, eventually freeing her beautiful tits, he watched as her plump, darkened nipples were leaking out so much creamy milk. Licking his lips, he couldn’t stop himself from not only just groping her with one hand, he started suckling at her other breast, drinking the warm milk. Both their bodies were tingling with delight as they were pushing closer and closer to shared orgasms.

David’s cock was throbbing and swelling within the mare, and Posey’s pussy was clamping down so hard on this human dick, that it wasn’t going to be long before the two of them were going to cum. The pleasure was melting into their overly sensitive senses. It wasn’t going to be long now, the two of them needed to have that sweet, passionate release. Closer and closer, the bed was rocking, thrashing about as the two were engaged in this savage mating. David’s cock was so deep, it was almost like he was trying to ram himself all the way into the mare’s womb, and Posey’s body was practically begging, ovulating at the though of this young man’s seed to flood her precious place.

“Come on, please…you can do it…” Posey moaned, arching her head back as she reached across to gently rub the back of David’s head, tenderly petting him in a loving fashion. “Fuck mommy’s pussy…you can cum inside me. Her eyes fluttered, almost radiating hearts as she looked at him. “Mommy wants to have all of your babies.” This was enough to drive the human over the edge, he needed to cum inside her. He needed to see if he could knock up this beautiful, needy milf.

Huffing and panting, he gasped out as David couldn’t hold himself any longer. Posey’s pussy was just too good. Ramming his cock as hard and as deep as he could, he bottomed out his length, pushing against the inner lining of her womb as the mare moaned out so whorishly. The human’s cum was so thick and hot, it was driving the mare’s senses over the edge as she was clamping down, squeezing and milking him as she could feel as though she was being bred by him. The pleasure was rippling through her senses, leaving them a mix of numb and overly sensitive as her insides were being filled by such a precious amount of cum. Swallowing hard, she cooed and shivered, pulling him back into a sloppy kiss.

‘Oh my…his cock is so big…and there’s so much cum. Oh my, am I getting pregnant? He’s not a stallion, but my womb is so full of his seed.’ Posey thought to herself as she moaned in David’s mouth while her tongue was rubbing along his. ‘Is he still hard?! Oh my, what a stud. He’s going to keep fucking me with this massive cock. I don’t think I can handle it, not alone, there’s just so much dick inside me.’

David couldn’t stop himself, even as he had just come, his dick was still so hard and throbbing. The mare’s pussy was clamping down, tightening along him as he couldn’t help but keep thrusting into her. The more he was fucking her pussy, the more cum was being sloshed and shoved into her. Her womb was eagerly tingling from the hot seed that was still being pumped into her. Whether he could impregnate this milf mare, he had no way to know, but was so engrossed in the pleasure of her moaning breath in his mouth, that he could barely think. All such higher, mental functions were focused on his cock, and he was going to keep fucking this mare over and over again. Posey only further moaned, loving every second of this feeling.

“You slept with him?!” Fluttershy gasped, sitting with her mother at her house. “You said you were just going to go over and see him, not have sex with him.”

“Well, things kind of went from one thing to another.” Posey blushed, taking a sip of the tea she was having with her daughter. “And…he was pretty intense.” Fluttershy blushed a little at the suggestions her mother was making. “And that’s what I wanted to talk to you about.” Taking another sip of tea, she looked more intensely at the mare. “I want you to help me fuck David.”

Fluttershy’s face was a massive scarlet red as she stumbled back, whimpering and cooing as she was struggling not to faint. Was Posey being serious? Was she actually suggesting that despite having sex with David, she wanted to not only let Fluttershy in on it, but was suggesting a threesome. The mare felt a shiver run down her spine. It wasn’t like she hadn’t been with another mare before. Her mind thought back to the time she and Applejack had a threesome with Big Mac in the barn one time. Or when she and Rarity had that mare on mare moments at the Ponyville Spa. Or even when she was invited to a party with Pinkie Pie, only for it to break out in an orgy. So it wasn’t like Fluttershy had never had sex before, but the idea of being with her mother was certainly not what she expected.

“See, yeah, I knew you’d react like that. But I’m sure David would love the idea.” Posey replied with a playful giggle. But this only added to Fluttershy’s worries. Did the human not know what this milf was planning? “Besides…” Reaching out, she grabbed at one of her daughter’s large tits, making her gasp and coo softly. “You have such lovely breasts, and sensitive nipples. David will love it.”

“O-okay…okay…I’ll do it…” Fluttershy cooed, panting a little as her mother was teasing her fat tits and plump, sensitive nipples. “P-please…c-can you stop…”

“Oh, sorry, I was getting ahead of myself.” Posey giggled, blushing as she drank some tea. From the way her own nipples were poking under her top, she was getting pretty aroused. It was all but obvious that she was looking forward to this. “We should decide on what to wear for him.” Fluttershy stammered her words for a moment. “I know, maybe we should ask your friend, what’s her name…Rarity, for some suggestions.” Fluttershy nearly fainted again at her mother’s sultry words.

The sound of David’s phone blaring to life with a number of text messages roused the human from an almost deep sleep. He had been so nervous for a while since Posey told him she had some surprises for him during the weekend. And since then, she had been sending him not only alluring nudes and lewd pictures of herself in erotically tight swimsuits. But there were even some short videos of herself masturbating, riding on a large dildo, telling him she can’t wait to ride his fat cock. Every time his phone rang with a message, he wasn’t sure if it was someone else, or this slutty milf teasing him. Opening his phone, he got his answer.

It wasn’t from Posey this time, but Fluttershy. It was a pretty sweet message, asking him if he was awake, and if he was busy today. Smiling warmly at the message, the icon he used when messaging the mare was a selfie of the two of them hugging. Quickly responding, David messaged that he was awake now, and that he wasn’t planning anything all day. Barely a second or so after sending this message, he heard a knock at the door. Curious, he threw some loose clothes on, walking over to look through the peephole. As soon as he gazed through he saw not only Posey, but Fluttershy was there. Without thinking, he opened the door.

“Posey? Fluttershy?” David asked, looking between the two. “What are you doing-” Before he could answer, the milf pushed herself against him, making out as she guided him back into his house, and Fluttershy shut and locked the door behind her as she followed.

Posey was all over David, passionately kissing him, pressing her hot tits against his chest, all while she moaned whorishly. The human kissed her back, but kept his eyes on Fluttershy. The mare was dressed in some heavy clothes that she took off, revealing her one piece swimsuit, but it was clearly more than skin tight, with her impressive cleavage on full display, not able to even cover her areolas. Her plump nipples pressed against her clothing, it was only adding to the way she looked at David with longing, loving eyes. Eventually, Posey pulled back, licking her lips as she dropped out of her heavy clothes, showing off a leotard that was somehow even sluttier than the one she had before.

“Hope you like the surprise.” Posey cooed, licking her lips, as she could still taste her kissing on her. “Oh, and you’ll love this.” Leaning up against him, she whispered seductively in his ear. “We’re in heat, and we want your babies.”

Something happened, David was sure something did happen after hearing these words, but he couldn’t remember. All he knew was that after hearing Posey’s words, his vision blurred. When he was more aware of his surroundings, he was on his bed, naked and passionately hammering his cock in the milf mare’s pussy, as she was on her hands and knees, her face making out with her daughter’s soaking wet, hot pussy, and Fluttershy was making out with David as she moaned in his mouth. The mares were quivering from the pleasure overwhelming their senses, pushing them to strong and soaking wet orgasms. The human cock was stretching her out, claiming her as his mare. Even as he became aware of his surroundings again, he didn’t stop himself as he was fucking into this milf with all his strength.

“Fuck…you’re so tight…” David huffed, thrusting into Posey’s pussy, raising one hand to smack against the milf’s ass, while reaching around with his other hand to kiss Fluttershy deeper. “I love you, I love you both. Marry me. Be my wife, have my babies, all of them.”

“Yes…yes…we want it…” Fluttershy cooed, moaning in his mouth as her tongue embraced his. “Give my mom your foals. Then fuck some in me.” Her voice was so sweet, so erotic as she spoke in such a naughty softness. “Make my mom pregnant, and then give me your babies like a loose slut.”

Posey tried to speak too, but all she could do was moan in her daughter's pussy, tonguefucking and making out with the sloppy wet opening, preparing her for the fat, human cock that was going to breed her. David’s dick was just so good, and the way he filled her was getting her over the edge. She was cumming, making her pussy clamp down on this dick, begging it to breed her, to mark her insides with his seed, and ensure she wouldn’t want anyone but him. Her husband didn’t matter anymore, how could his wimpy dick compare to this massive cock stretching and ruining her. And from how tight Fluttershy’s pussy was against her mother’s tongue, she wanted to be just as knocked up as the milf whore.

David picked up the speed, feeling as Posey’s cumming pussy got tighter, making it a little harder to pull out. She wanted him to blow every last ounce of thick seed in her. Her ovaries were in overdrive to be bred, and she wanted to have as many foals as possible. Posey’s mind was mush, driven only by the instinct to get pregnant. She wanted this human’s spunk to flood into her, bloating her as it had before, but to make sure that every single one of his swimmers were going to gangbang her eggs, ensuring the strongest foals would be born. And if any of them were daughters, no doubt they would grow up wanting to fuck their daddy when they get old enough. The thought was too much, pushing her over the edge.

“Fuck…here it comes…” David groaned, still making out with Fluttershy, holding her close. “Get pregnant, get pregnant, get pregnant, get pregnant you fucking whore!” Slamming all the way into her, he let out a hot torrent of virile cum into the milf mare’s fertile womb.

Posey screamed in Fluttershy’s pussy, pushing her daughter to a spraying climax against her face, soaking her as she continued making out passionately with this sloppy hole. David held himself in place, making sure nothing leaked out of the mare’s tight hole. She could feel the way his thick spunk was washing over her ovaries, drowning them in the foal batter that was fertilizing her like the loving whore she was. Eventually, the human pulled himself from the mare’s fucked silly pussy, letting her collapse over the bed while Fluttershy, in a heat of passion, pushed against David’s body, knocking him back so that his cock was pointing upwards. The normally shy and timid mare wasn’t the same sweetness she was before. She was a ravenous beast in a body of juicy ass and fat tits.

“Oh my…you impregnated my mother…I’m going to have a sibling because of you…” Fluttershy cooed, straddling David as she lined up his still dripping cock against her soaking, equally dripping pussy. “I’m sorry…but I need this. Please, make me pregnant, give me all your babies too.” Reaching up, the human groped at her flank, and pulled her down on his cock.

Fluttershy screamed out in a breathless gasp of orgasmic bliss. She had never felt this full before, and the pleasure that was rippling through her body was making her tremble, almost thrashing as she started hissing, eyes rolling back, and her nipples were so hard. Driven by this primal instinct to be bred, the mare immediately started bouncing on this cock, flapping her wings to keep herself steady, as she hunched over, smothering David’s face in her tits. Opening his mouth, the human started suckling hard on her nipples, making her moan some more as her body was already prepared for motherhood. Fluttershy’s plump, juicy nipples were lactating, driving him to suckle and drink the milk that should be going to her soon to be developing foals.

David’s cock, still sensitive from the way he blew his life giving load in Posey’s pussy, throbbed and was going to cum again at any moment. But this wasn’t going to be the end of his orgasms. These pussies were just so good, pushing him to hotter and wetter climaxes, but to ensure these mares were going to be swollen, bloated with as many of his foals as possible, he was going to push himself. David was going to fuck, and fuck, and fuck, and fuck, and fuck into her pussy, delving so deep inside her, her velvet soft womb was being rubbed, stimulated, pushing her ovaries to ovulate while the heat surging through her body was making her want all his seed inside her. She was cumming on this dick, feeling how much David loved her, and she loved him back. Her eyes were spinning, nearly manic as she wanted to be bred like a slutty bitch.

“Oh my…holy…shit…fuck…David…I love you, I love you, I love you, I love you…” Fluttershy panted and moaned, almost to the point and maddening chanting as she bounced on this cock harder, riding it as if she wanted to claim it as hers. “Make me pregnant, make me pregnant, make me pregnant, make me pregnant, make me pregnant, make me your pregnant bitch!”

This was too much for David, he couldn’t hold himself in again. Grabbing and groping hard on her ass, he pulled Fluttershy hard over his cock, slamming his length as deep into her pussy, depositing another hot and virile load all the way into the mare’s fertile, gluttonous womb as her ovaries let out all her eggs, letting them be flooded and consumed by all the spunk as she was cumming from being impregnated like this. The pleasure was too much, her mind just couldn’t process it all, and after several seconds of the aftershocks of it, she collapsed forward, laying and twitching on the human she loved. David, being covered by fat tits, lay there as well, not noticing as Posey seemed to be getting some strength back.

“Looks like you’re going to give me another child.” Posey cooed, crawling her way over to snuggle against David’s body. Hugging him, her breasts pressed against his arm. “How does it feel to have two beautiful brides-to-be?” She whispered in his ear. “Or maybe I should ask, how did it feel to knock up my daughter and I…daddy…” Her whorish words caused his cock to throb, blowing a little more into Fluttershy’s cooing, twitching pussy.

“It…I loved it…” David said weakly, turning his head to look at the mare. “I’m happy I have you both to-” Once she could, she started kissing him again.

“Please keep fucking us, daddy…” Posey moaned in his mouth, her body trembling as she felt her arousal only growing with her returning strength. “Fuck us, love us, make us yours and give us all your babies.” David kissed back, more than happy to not only give this slutty mare and her daughter what she wanted, but was looking forward to his new life with these beautiful mares.