#1 Pippsqueak

by Paul0504

Rating: mature
Tags: Alternate Universe, Anon, Porn, Pipp Petals, My Little Pony: A New Generation, Romance, Sex
Length: 4973

Anon is obsessed over Pipp's ass, and the pegasus notices. Instead of scolding him, thought, she decides to play a bit with him.

You know what's the biggest problem of being best friend with a cute pegasus like Pipp?

Her ass. That giant, juicy, and delicious ass that drives everypony in Equestria completely crazy, even Anon, who stares at it constantly on a daily basis, to the point he can barely control himself to not fuck Pipp's brains out while smacking her ass.

Yet when Pipp herself notices his stares, instead of growing mad, she actually plans out a way to get a taste of human meat, and see how different it tastes from a pony's.

Published 2023-11-05 14:30:00 UTC
Last updated 2023-11-05 14:30:00 UTC

A princess also has needs

"Come on, Anon. I know you're gonna love this!" Pipp Petals said with a smile, dragging her human friend by his hand.

"I guess..." Anon rolled his eyes. Pipp's strength, for him, felt like if a puppy was trying to bite him; so he simply walked along with her.

You may know already how theses stories go: Anon, a human, ended up in a magic land of talking, colorful ponies, and now he lives in here with them. What else is there to tell? Nothing you don't already know. It's an Anon story. Why don't we skip this part and, see how Anon got dragged into a hot springs by his closest friend from this world?

The entire "Anon self-insert genre" --a human in a world of ponies-- usually falls in three different tropes:
-The fan that only wants to meet their heroes from TV and thank them for all the lessons they have learned.
-The fan that just wants to make a harem with as many mares as possible.
-Then there's this Anon's perspective: He honestly couldn't care less for about the first two tropes. He had no prior knowledge - at all - about Equestria before his sudden arrival, and he's not interested in fucking all the ponies he wants, either.

However, he does have a certain... interest with one and just one pony: Pipp Petals. He considers her his best friend, and also his secret crush. Seriously, it would be foolish of him not to fall for her. She's such a cutie, a really sweet pony that always wants to cheer you up, and she pleases her fans as much as she can... Not to mention how fucking hot she is.

It should be illegal for a pony to be as hot as Pipp Petals, or so Anon thinks. She has a giant, round, juicy, and delicious ass that drives everypony in Equestria completely crazy, even himself, not to mention her big tits. Seriously, Anon has found himself fantasizing about riding Pipp and fucking her brains out on several occasions. He has even come to a point where he has to control himself so he won't slap her ass, 'by mistake.'

It was constant torture to see Pipp's ass jiggling from one side to the other and not give it a slap, or just full on fuck her while smacking her flankcheeks. However, he still has some manners, hence why he never approached Pipp in a way that could make her feel uncomfortable...

Yet there's one little flaw in Anon's entire plan... Although he may not touch, he can't help but stare. And that has already betrayed his intentions to the young princess.

Pipp has lost the count of how many times she has caught Anon staring at her rear, and how many times Anon has failed to pretend he's not staring. It made her feel a bit disgusted at first. How could Anon stare at her in such a repugnant way? She didn't like it, but she did her best to stay calm and not mention it.

As time went by and as she got to know Anon better, Pipp's disgust shifted. She began to feel flattered by his constant staring. Of course, she's very aware of how big and juicy her ass actually is, which is why she can't blame Anon for staring at it. As time went on and her friendship with Anon developed further, Anon's platonic feelings were not so platonic. And Pipp actually began to crush on him as well.

For human standards, Anon was just an average guy. Sure, he had some muscle, but nothing any human girl would really go for... Pipp, on the other hand, was drooling over Anon's body just as much as he was for hers. Anon has never noticed her sidelong glances--being distracted by her own body of course. And this irritated Pipp a bit... But not for long.

She reached her limit one day. When furiously masturbating while imagining her best friend riding her and making her his personal cum slut wasn't enough, it was time to take action and actually make Anon notice her and ride her hard like she imagined. She planned, and though, he already fuck her with his eyes, it's just a matter of making him take it to the next level, while making it seem like it was his idea.

And how's she gonna do that? Well, Anon already looks at dat ass on a daily basis and stares at it for hours sometimes. All she has to do now is give him a little push. Make him brake decorum, and finally go for it. She already has him drooling for her, how hard can it be get Anon to take the plunge?

Spoiler alert: Not very. Barely an inconvenience. Oh, he'll try to resist, let's see how that works out for him.

She set her plan in motion. Pipp made an appointment at the hot springs for two visitors. Making up the excuse that she paid for herself and her sister, but Zipp couldn't make it at the last minute because "she had to investigate something with Izzy." Still having one extra non-refundable ticket, she had "no other choice" but to invite Anon.

Anon tried to refuse at first, but he ended up accepting because Pipp used the ultimate pony weapon: puppy eyes. Anon was overwhelmingly defeated. Her flawless plan was coming together: Drag the two of them to the hot springs where no one else will bother them. Then push him to his limit by 'accidentally' showing more of her rear then she should, and then get taken to pound-town. Easy-peasy.

Getting back to the story... While Anon and Pipp were waiting for their two hour hot springs session, Anon was beyond terrified. It was a two hour session! Trapped inside of a enclosed place where he'll be all alone with Pipp and her delicious ass. That fucking big and juicy ass; those tempting hypnotizing mounds of absolutely grabbable flesh; will be in close proximity for two uninterrupted hours.

'This shouldn't be that bad,' he thought to himself. Then he saw a sign next to the hot spring rules that read "sex is allowed." 'Fuck!'
"I can't fucking believe you convinced me to do this..." Anon feigned annoyance, but felt extremely nervous as to what may happen.

Pipp giggled and winked at him, "Now now, Nonny, don't be so shy," Pipp flirted. "Deep down, we both know you've been needing it. Zipp's been taking you from one side of the town to the other in search of useless clues about that dumb message from Twilight Sparkle, and instead of finding anything, you end up exhausted! Consider this a little brake with your bestie!"

'The problem's that I wanna fuck my bestie, and being alone with her will be the opposite of a break.' Which is true because his hormones were barely under control as it is. "If you say so, Pipp..."

"You can play the tough guy all that you want, Anon. Deep down, you know I'm right." Pipp teased with a smirk, walking to the hot springs' entrance.

Anon stayed behind to remove his clothes and then covered himself with a towel. Taking a deep breath to steel his nerves, he entered the hot springs as well, closing the door behind him. Once inside, he let out a nervous sigh, knowing that he won't be leaving this room for the next 120 minutes. Two full hours of resisting he sexual urges and desires.

When he turned around, he immediately was put to the test. Pipp, had decided to "stretch out" a bit before entering the hot springs. Anon's eyes were glued to her flexing glutes. Pipp's plan was already set in motion and she was already winning.

Casting his eyes a bit further down rewarded Anon with a sight of Pipp's pink petals. Anon's eyes were at war of which part to ogle, her spankable ass or her inviting pussy. Taking notice that his other head was staring to join the action, he immediately covered his crotch with embarrassment. But he never stopped staring. His eyes glanced further down to find yet another reward, Pipp's jiggling tits. As much as ponies walked around with their parts hidden, it was impossible how Pipp could hide her fat tits. Seeing them only further strengthened Little Anon's resolve. As he was just about to look up and away, he spied her star under her tail, which could be, without lying, the most tantalizing zone of her entire body.

The number of times Anon has imagined himself hammering his cock in her plot hole could scare anyone, even porn addicts. Seriously, he just desires to fill her anus with cum and slap that ass as if his life depended on it––

And there he goes again, day dreaming as he stares at Pipp's rear. He quickly shook his head to snap out of it, then rushed pass Pipp and quickly entered the water. Going in a hot spring with the towel on is not the normal way to relax, but it was the only way to hide his massive erection from her.

Pipp noticed his sudden plunge into the water with a raised brow, but she choose to shrug it off and join Anon inside the hot springs. She still has 119 beautiful minutes to push this human to his limit, so there's no need for her to rush.

For the next thirty minutes, Pipp moved around the hot springs and laid in all kinds of positions. Making sure her rear was showing very clearly to Anon every time. Of course, he couldn't help but stare every time. Each of those times, his erection grew a bit bigger and a bit harder. Adding up to a point where it was way too hard and a little painful to ignore.

And finally, Anon reached his limit! However, he still had respect for Pipp and did not touch her. But he still had to do something. So, he simply exited the water, moved his towel to the side and started to stroke himself, in hopes of getting relief and frustration out.

Pipp, was still aiming her weapon of mass destruction, her rear, straight at Anon, and didn't notice what he was doing. She just knew that Anon hasn't approached her at all, and was starting to run out of patience. Yet, when she turned around and faced him, her eyes opened wide in shock when she finally noticed that Anon was masturbating.

The sight of Anon's exposed cock lit up her face like a red tomato and made her jaw drop. Maybe for human standards, Anon's cock was just average. For pony standards, it was pretty big, and exotically shaped. Pipp was intrigued, wet (not from the hot springs), and full of desire. She definitely needed it inside of her. Now.

She noticed that without even trying, Anon had made a devasting blow in their war. Quickly clearing her head, she regrouped.

She decided to act like she hasn't seen anything yet, and took in the eye candy presented to her. She let Anon enjoy himself for a moment. But when it looked like Anon was close to coming to a finish, she chose to interfere and loudly cleared her throat. "Ahem!"

Freezing with his hand mid stroke on his dick, all manner of alarms bells rang. Knowing he was caught, but hoping for the best, he slowly turned to see Pipp, who was frowning at him, continuing the charade that she 'just now' discovered his little act. Completely embarrassed, Anon immediately covered his member with the towel, even though he knew it was too late.

"Shit!" Anon said out loud in panic and embarrassment. "Pipp, I-I'm so sorry! I-I can explain!"

"Well, I hope so, because you seemed very happy while 'massaging' your 'little' friend." Pipp replied with keeping up and angry act. Seeing Anon so flustered is fun and she finds it quite hot, if she's being honest.

"I-I, um... I-I was just..." Anon was trying so hard to think of an excuse, but he eventually sighed defeated and decided to speak with the truth. "You know what? I'm not even gonna try and hide it anymore. I was masturbating, Pipp... Because I saw your ass and, well..." He explained, while scratching his neck embarrassed.

Pipp was shocked now. Not about him fapping, heck, she even stared at the act! She's shocked because he openly admitted what he was doing instead of trying to paint himself as an angel that made a little mistake... She was honestly surprised to see this much honesty, and it even inspired her a bit.

"...I honestly thought you'd try to hide it, but I'm impressed you didn't..." Pipp said, now fully dropping the act, although she did sounds genuinely surprised.

Surprised, Anon's eyes open wide. "...Why do you sound like you already knew what I was doing before interrupting me?"

Now it was time for Pipp to feel embarrassed, so she gulped, stood up, approached Anon, sat at his side, sighed, and then looked at him. "...I... I've been trying to push you to your limit on purpose... Ever since we came here..." She confessed.

Anon's eyes widened even more, if that was even possible. "YOU WHAT?!"

"Anon, I've seen the way you stare at my ass for months ." Pipp replied nonchalantly. "Sure, you haven't touched me or anything, but I can tell by the way you always look at me that you desire me. And honestly? I... Have desired you in similar way for the past two months..." She confessed with a slight blush, also looking away from him.

So many emotions ran through Anon. Surprise, confusion, happiness... And also lust. Lots, and lots of lust.

"I wanted to make you touch me, but–– Eep!" Pipp was cut off when Anon suddenly tackled her, looking down at her with a dangerous glow in his eyes. "A-Anon?!" The princess asked confused. "W-What are you––"

But whatever else she was going to say, it got cut off again when Anon locked his lips with hers in a kiss, startling her and making her blush all over again. She had no idea on how to react at first, but eventually, the gentle way Anon moved his lips with hers made her return the kiss, even pressing her hooves against his naked chest.

They separated after a while and looked at each other in the eyes, both breathing heavily and catching their breath, but also smiling at each other.

"...Sorry, Pipp... I couldn't contain myself anymore..." Anon replied.

"It's fine, Nonny." Pipp replied playfully, also biting her lower lip. "I wanted you to stop containing yourself, remember? That's why I brought you here, silly~"

"So Zipp never even knew we were coming here?" Anon asked with a playful smirk. "You're more naughty than I ever gave you credit for, princess~"

"Maybe I am. How about you stop containing yourself and find out, huh?" She suggested.

"You sure? Because if we do this, there's no turning back..." He pointed out.

"Maybe I don't want to turn back, Nonny." She then approached his ear and whispered in to it, "Now stop playing around and take me." Her breath on his ear sent goosebumps down his body. "Make me your little slut~"

Not able to resist such a petition, Anon kissed her lips once more, before starting to lower himself as he kissed the pegasus' neck, then down to kiss her fluffy chest, down further kissing her plump tummy. Finally reaching the end where he stopped and got an eyeful of her pony tits and pussy. For pony standards, Pipp's tits were large, especially for a pegasus. Since ponies are smaller than humans, her tits looked a bit on the small side for Anon. However, what they lack in size, they made up in sensitivity.

The moment Anon squeezed Pipp's tits, the pegasus arched her back and releasing a loud and lustful moan of pleasure. When Anon played with her stiffening nipples, her moans of pleasure increased, driving Anon crazy. He continued to enjoy the softness of her tit flesh, but he was far from being done, moving his face to the left breast, began to suck and gently nibble, following with her right. He continued to lick, nip and eat at her soft weighty mounds as a desperate predator might enjoy its prey.

Pipp's moans intensified, and she clamped her thighs around Anon's head, keeping him right where she wanted, while stifling her moans by covering her mouth with her front hooves. She was trying so hard not to be loud, but the moment Anon held both her tits together and started to suck on both of her nipples simultaneously, she nearly lost her mind. There was no holding back the moans of having both her breasts treated to such pleasures.

Pipp had gotten wet witnessing Anon unknowingly and openly masturbating right in front of her, but by now her inner liquids were starting to trickle out of her flower and down her legs. A small puddle began to pool at her feet on the floor next to the springs. Anon saw and came up with an idea that made him smirk mischievously.

"Princess, let me show you one of the many wonders of having fingers instead of hooves!"

"What are you talking–– O-Oh!" Pipp suddenly squealed when Anon penetrated her petals with three fingers. He began to fingerfuck her, but slowly at first. Gradually moving his fingers up and down, slowly speeding up. He leaned over her and kissed her neck once more, adding small bites to give her even more pleasure. "G-Gosh, Nonny... Y-You're driving me crazy!"

"And I'm just getting started~"

Anon decided to take things up another level. He gently removed his fingers, leaving Pipp confused and her pussy wanting. But then she saw his penis presented in front of her. Her eyes widened in surprise, up close, his cock looked even bigger than before. Even though she was no stranger to sex, seeing Anon present his exotic looking member made it almost felt like this was her first time again.

Still, she put those thoughts aside and opened her maw. Anon could feel the her rapid hot breaths on his dick. He slowly put it to her mouth and Pipp began to suck. Gently at first, then, not so much. Loud slurping sounds echoed throughout the springs. She wanted to be very clear that she's enjoying this, probably a lot more than she realized. Not that she really cared, though.

Pipp's hot mouth and delicate tongue bathed Anon in a tight warmness that brought out his own cries of bliss. His audible 'encouragement' made her double her efforts. She began to bob her head and lick around the tip as Anon's tool almost left her mouth. Then, with each down thrust, she swallowed just a bit more, and a bit more. Pipp could hear Anon wail in ecstasy as he was being driven crazy. He looked down at Pipp as she took his cock. She was lost in her own world of giving head, and Anon was lost in his by getting one of, if not the best, blowjobs of his life. Before he knew it, he had grabbed Pipp's head and crammed every inch down her throat.

Pipp, was surprised by Anon shoving his member down her throat. But she was enjoying being used so much, that even the lack of air didn't bother her. If anything, it just turned her on even more. As more juices continued to run down her hind legs, she made sure that Anon did not pull out until he finished. Even after he removed his hand, she continued to take everything, sucking as hard as she could while starting to get tunnel vision.

Eventually, the human roared as be deposited his first spurt directly in to her stomach. Surprised by his sudden climax, she began to withdraw as his second and third ropes of cum filled her throat. Being constantly teased by Pipp, over months has caused a huge backlog of cum, and Anon was making up for lost time. His fourth spurt caused her to gag and cough while his fifth spurt of cum filled her mouth and came dribbling around her cock-stuffed lips. She gagged once more, this time with some of the copious amounts of cum coming out of her nose. Pipp's tunnel vision was nearly closing in completely, and her eyes began to roll back in her head. Anon, in a moment of post nut clarity, saw the choking pony in front of him and pulled out of her mouth with a pop.

Pipp coughed up cum and took a huge life giving breath. Feeling slightly dizzy from the experience, she continued to gasp until she caught her breath. She wanted to have fun, but not at the expense of almost suffocating to death.

"...You could've... warned me or something..." Pipp said, a bit mad he had cum without warning.

"I don't know, you don't seem to mind getting suffocated with my cock." Anon pointed out with a snort.

"Shut up." Pipp rolled her eyes, then smirked and opened her hind legs, presenting her sopping wet pussy to her human friend - or whatever title he is for her at this point. She'll figure that out later. "How about you make it up to me by filling my womb~?"

With out a word, Anon grinned and approached her. Took his member in hand, aimed directly at her flower, and plowed all the way in. Her sopping wetness made it easy. Pipp cried out in surprise, pleasure, and a bit of pain all at once. He was so big. Anon moaned out at the extreme tight heat wrapped around him. Pipp was way too tight for Anon, to the point it was squeezing his cock almost painfully. He gave them both a moment to adjust to each other. After Pipp gave a nod, he grabbed her legs and started to thrust deep inside of her.

Anon didn't hold anything back. From what he saw, Pipp wanted it rough, so he gave it to her rough. He moved his hips and slammed them against the pegasus. The sound of flesh against flesh began to fill the area, only to be drowned out by Pipp's moans. Pipp was having the time of her life being ridden so hard. No one had ever treated her so rough and she was approaching her own climax faster than she expected.

Anon found that watching his cock pound in and out of her pussy was hot, but right above their union were Pipp's tits. They moved and bounced back and forth with the time of each of his thrusts. With such a hot and sexy sight, and easy access, how could Anon not enjoy playing with them. When he grabbed her sensitive mounds and flicked her stiff nipples with his thumbs, she almost came right there on the spot. Instead she let loose the most guttural, sex induced moan she ever had. It would have been embarrassing if she could think straight. Anon found her moan not only an acknowledgment of a job well done, but hearing her like that, pure sexual emotion without holding back, was one of the hottest things he ever witnessed. But right now, he choose to focus at the task at hand.

He was moving so fast and thrusting so hard that Pipp's mind started to blank. She could barely think anymore as she felt her innermost barrier almost penetrated by her human companion. If she knew that human cock felt this good, she would just suggested the idea of Anon fucking her ages ago. Well, better late than never, right?

Once again, Anon was close to his climax. Letting go of her tits, he leaned in and held her in a deep kiss, full of passion. Their tongues mixed and danced with each other. Releasing the kiss, Anon looked directly in to her eyes, "P-Pipp... I-I'm gonna..."

"Fuck yes, do it! Cum inside me, Nonny! Make me your little slut!"

Well, she is a princess and he could consider that a direct order. Regardless, with one deep, final thrust Anon stayed buried deep in Pipp's sex, and experienced the best cum of his life. Rope after rope of cum filled her womb.

Feeling searing hot cum pour into her, Pipp came hard. Her vaginal walls clamped down on Anon's cock trying to wring every drop from him.

Both of them cried out their mutual satisfaction, holding each other and ending with another kiss.

As Anon kissed and held Pipp, his hand slipped down to her juicy bubble butt. Anon pulled out of her, releasing a small oozing stream of cum. But this was not over.

Anon told Pipp to turn around and lay on her belly, tail up. Knowing where this was going, she complied. Anon squeezed that ass and it felt better than he imagined. The pliant flesh had an underlying firmness. He groped and fondled. The ass moved to his whims in a mesmerizing fashion. His erection started to make a comeback. He grabbed both cheeks and spread them apart. Witnessing her tail hole only made him more courageous. He pressed a finger to her virgin star and after a few prods, it sank in.

"Mmm, Anon~ You wanna fuck me there, too?"

"I've been dreaming about this for months, Pipp."

"Then go for it, you handsome boy~"

Nothing else had to be said. Using some cum dripping from her well used pussy, he prepared her hole for entry. Once again he took aim and sank in. Pipp let out a grunt as Anon penetrated her anus in one go. It was even tighter than her pussy, but that only incremented the levels of pleasure for them both.

Anon began to move immediately, not even considering to hold back or give Pipp a chance to adjust. Pipp herself moaned loudly at the feeling of pleasure and pain from Anon's large dick invading deep inside of her ass. As he continued, the pain slowly ebbed and gave way to more pleasure. She didn't know that this hole could feel that good. Her mind started to go blank again at the continued thrusting. Her tongue lolled out of the side of her mouth while her eyes began to show hearts in them.

"Nonny, you're so fucking big! I love it!" The princess screamed happily.

Anon smirked, then he started to move his hips faster. His dick was in heaven. While her pussy eventfully loosened just enough to accommodate him, her ass kept tight no matter how hard he pounded. Lust began to fill his mind as the pleasure was fighting to bring yet a third climax.

Then, Anon grabbed Pipp's mane and pulled it backwards. She was surprised by the act but also satisfied on an instinctual level. It hurt, but not much, and in a good way. Even though he was being so rough, she felt safe. Then he smacked her left flank hard. Without thinking Pipp screamed out "Yes!~"

Anon had wanted this so badly, ever since he first saw her. Now he was living his dream doing it. So he gave the right flank an equally hard smack. "Oh YESSSsssss!~" Pipp was breathing so hard from being plowed in her back end. It wasn't just the pleasure. Anon was laterally fucking her so hard that it was forcing air from her lungs. A smile formed on her lips and her eyes were filled with love and lust at the sensation of Anon's cock moving inside of her. After a third spank on her ass, not only did her flanks shake like a bowl of jello, it caused her to climax instantly. It was so fast and unexpected her brain stopped.

Pipp's lustful moan, the tight squeeze on his cock, and seeing Pipp's fat ass cheeks bounce with each thrust was too much. Anon finished, letting out a satisfied grunt, and filling her ass. Pipp's open mouth was frozen in a silent scream. She remained still until Anon pulled out. As he pulled free leaving a trail of come between her flanks, she sucked in a huge breath of air as if she had been holding her breath this whole time. Then moaned loudly until she regained her senses. Anon saw his handiwork. He had smacked her so hard, that there were red handprints just barely visible through her fur.

Seeing the red swelling in the shape of his hands, he knelt down and held Pipp gently, trying to rub away any pain. After all, he wanted to do this again, so he didn't want to leave her with a bad experience.

It stung a little when Anon rubbed, but it felt nice to be looked after. He was so big, he was able to hug just about all of her at once. She enjoyed the warmth of his embrace.

Pipp breathed heavily as she calmed down after their shared exercise was over. Looking over her shoulder at Anon with lustful, heart-shaped eyes, she let Anon know exactly what she was thinking. "You... were amazing, Nonny. I haven't felt that good having sex in, um... ever..."

"...No problem, Pipp..." Anon replied with a smirk. "But next time you want me to fuck you, just tell me instead of making up some lame-ass plan that drags us to an almost public place, okay?"

Pipp giggled and sighed. "I'll think about your offer, Nonny. No promises, though~"

Author's Note

Me? Publishing a new story during No Nut November? Hell yeah! 😈

Thanks to Dude3 for fixing this story's mistakes.