Pipsqueak gets all the Ladies

Fucking with Two MILFS in a row in his life. Sure, he fucked with Cream Heart, Button's mother, but Twilight Velvet and Windy Whistles, the mothers of Twilight Sparkle and Rainbow Dash like that? It was something else. Of course, Pip couldn't really count out Cream Heart, she was one of the hottest mare's in Ponyville, and she was an expert at giving sex, and these two mares were just as good as herself

Meanwhile, Pip was feeling more proud of himself and he was hoping for more MILFS to have sex with in the future. As usual, he has to wait for that opportunity to come to him in the future, and he knows love don't come easy. No, time waits for nopony after all, and Pip just had to take the wait, but he was a very lucky foal, and nopony could resist his adorable face, and it was one of his greatest attributes in his life.

He knew that there was more to life than just sex. He enjoyed ice cream, toys, video games, pretty much many things little colts loved. He was out with his mother for more shopping for produce and groceries at the farmer's market, and Daisymay was just done paying for some apples from Big Mac.

Pip's mother promised him that if he behaved and helped her out today, she will buy him an ice cream cone, and the boy gladly agreed.

After all, what sort of child does not like ice cream? Pip was a boy who always behaves and he wasn't a star student for nothing.

The last thing Daisymay needed to get was five leeks in her basket and she can buy Pip his treat and go back home. Now she had purchased those vegetables, Daisymay was off to the ice cream parlor and something caught Pip’s nose as he followed her.

Whatever the scene was, it smelled rather nice, like a bundle of cookies hot out of the oven. He licked his lips and he realized it was coming from the parlor as soon as he entered it through the door.

“Hmm, What is that delectable scent?” Asked his mother.

“Smells like cookies or something, mum.” Pip replied modestly. “Maybe we should look over and see what they are baking for the toppings.”

“Good idea, darling.” They went up to the counter, and there was Rarity with a pony that had a body posture similar to Mrs. Cake from Sugarcube corner, but a different coloring on her fur, a pale fuchsia color to be exact. Her eyes were a light cornflower blue color, and she was a unicorn and the nare’s mane was a fusion of grayish indigo and grayish blue.

She did look a little bit like Mrs. Cake. But she was a unicorn, not an earth mare. One other interesting features about her was her cutie mark, which were three chocolate chip cookies. “Splendid! What a perfect way for you to start your first day on your new job, mother.” Rarity admired her.

“I certainly hope so, Rarity.” Said The unicorn mare. “These cookies are a perfect match Togo with the ice cream as toppings.”

And there was Pip’s answer to why the scent of cookies were fuming the whole air. He smiled and he humbly walked over and hopped on one of the stools. “Excuse me, miss.”

Rarity smiled and she recognized his mug anywhere. “Pip, darling! It is always a pleasure to see you here once again. Ooh, may I introduce you to my mother?”

“Mother?” Pip Said. “That makes sense.”

Rarity’s parent made a chuckle, and she said: “Indeed. My name is Cookie Crumbles, the finest baker in all of Fillydelphia. You know, right before I moved her to Ponyville to be closer to my own two girls.”

“Oh ho ho, mother.” Rarity giggled. “You are quite a lady. Pipsqueak is such an adoration in a Ponyville, and quite a helper if needed.”

“Pipsqueak?” Said Cookie Crumbles. “Not that I don’t like it, but, why are you called that name?”

“Because i’m... smaller than most goals around Ponyville.” The colt admitted flatly and he sounded a little ashamed to say such phrase. “Just look at me on this stool.” Cookie Crumbles did exactly that and she saw how tiny the colt was, but he wssn’t reslyl that short, like an infant would be,

“My, you are a small foal.”

“Well, thank you.”

“Not that it’s a bad thing, Cookie. It just..l stinks that I am smaller than most foals. I get picked on by some kids sometimes because of that. Just look at me stubby legs. I mean, you can fit me in a lion’s mouth and he would gobble me up whole in a second.”

“Don’t be so hard on yourself, sweetie.” Said Rarity. “Being a small colt is not such a bad thing. Think of yourself as an adorable puppy or a kitten.”

Young pip was thinking about what the beautiful white mare was suggesting to him, and he did imagine himself as a puppy or a kitten. He was just about small enough for a costume like that, and there are many dogs and cats in the world that have the same kind of fur coloring as he does, so that would make him unique. One peculiar pooch he thought of was Winona, Applejack and Applebloom's brown and white border collie that herded the animals with them.

As he was thinking about it some more, Pip finally said: "Well, I would make myself a cute puppy if I was born one."

Both Rarity and Cookie Crumbles laughed at his adorable answer. "Isn't he just so adorable?" said Rarity. "It is most becoming of a young child like him."

"I absolutely concur with you, Rarity." said her mother in agreement. Her daughter then whispered something in her right ear and she had bedroom eyes. Pip instantly knew what this probably meant for him, and he was liking the idea of what Rarity might put into her own mother's head. "Hmm, I don't know. A colt like him, I suppose he would love it."

"Pardon the interruption." said Daisymay. "But, my name is Daisymay, Pip's mother, and I seem you already know my son's name. I am not trying to sound rude, it just looked like you were hitting it off, and that you knew Rarity here."

"Always a pleasure to meet a new face." said Rarity's mother. "I am Cookie Crumbles from Fillydelphia at your service."

"She moved her to be close to Rarity and Sweetie Belle, mum." Pip explained.

"Hmmm. That's rather interesting."

Pip heard his stomach growling and he said: "Ooh, first thing's first. Can I please have a regular waffle cone with two scoops of vanilla?"

"You certainly got it, Pip." said Cookie. "As a matter of fact, how would you like to have some of my signature cookies inside of it? They are one of the greatest in all of Equestria. I even got rewarded for Equestria's best cookies next to Pinkie Pie."

"That... would not surprise me."

Pip's mother, Rarity, and Cookie Crumbles laughed. "You are just so amusing." said Rarity.

Cookie Crumbles then went to the ice cream machine, and created two scoops of soft-serve ice cream but not before she put small bits of chocolate chip cookie bits in it.

When the colt received it and his mother paid it, Pip took the first bite of his treat, and it tasted so yummy and the crumbs of cookies were out of this world.

"Hmmm. This is so delicious." Then Pip began eating it a little bit more faster than before.

"Careful not to get brain-freeze, darling." Said Daisymay.

"Don't worry, mum. I won't." It took about five minutes for him to finish the whole ice cream and Cookie Crumbles was having a little conversation with Daisymay and they were really hitting it off one another.

"So, how was it?" said Rarity.

"It was so yummy!" The colt replied.

"Perfect. I knew you would love my cookies." Said Crumbles. "Now then, how would you like to come with me for some extra 'dessert'?"

"Hmm. I don't know." Said Daisymay.

"Come on, mum. You and Cookie Crumbles seem to be getting along just fine. Look how you guys were talking. This could be a start of a new friendship between you two."

"You two have been getting along quite nicely since you have first met since... the first five minutes you saw one another." Rarity added.

"Yes. I suppose." Pip's mother said.

"And, if you want me to make you a puppy outfit, or a kitten one, feel free to let me know." The young unicorn mare said to the colt.

"What? But... everypony would laugh at me." Pip's cheeks began flushing res like two tomatoes.

"Oh Rarity," said her mother. "You are such a tease."

"Well, I suppose you can go with her, only because we are good friends and we should have a martini lunch."

"I agree, Daisymay. Do let me know when you want to do that with me."

"Most certainly."

Then Pip went with Cookie crumbles and they went upstairs to find a storage room where the cookie dough was hidden and stashed away.

A cute, sly smirk appeared on Crumbles' face and she closed the door before locking it with a key.

Pip felt himself being tackled on the floor and he felt Cookie Crumbles engulf his penis inside of her mouth. The young colt was enjoying this and he was blushing his cheeks again.

Now he was getting what he wanted, and he let his mind be at ease as Cookie Crumbles was giving him all the pleasure and joy he wanted to take in himself.

Pip was right when he Saw Rarity whisper this in her mother's ear and he could tell by her face when she was being sexy and seductive.

It took about ten minutes before Pip was feeling the orgasm riding up in his fin as she was sucking and sucking through this course.

He ejaculated before he could warn Cookie Crumbles but it was okay. She loved it either way.

After she was done swallowing every last drop of his semen, Cookie Crumbles stood back up on her feet.

"Well, Rarity told me you.... goofed off with her before, Pip." She said in a smooth voice. "Well, I can be just as good as her when it comes to sex."

Before Pip could say anything else, Pip felt his penis being engulfed in her vagina and Cookie Crumbles began bouncing.

"Don't worry," Pip grunted. "I'll give you some ice cream of my own."

"Perfect. That's what I wanted to hear."

She was bouncing and bouncing on his dick and it felt so nice against his sensitive skin.

Young Pip knew he was going go have lots of fun after this, and he was twitching his head in happiness.

It took about fifteen minutes for it to kick in but Pip told her that he was going to climax.

Just like that, Cookie Crumbles began bouncing faster than before.

Like a broken fountain, the colt ejaculated a big amount of cum inside her hoo-hoo, and Cookie Crumbles began yelling in pleasure.

The colt was squirting his happy juice inside of her at least four times and when he was done, his head was swirling with ecstasy.

As soon as Cookie Crumbles got off, Pio was panting and she was fookg the same as they both laid on the floor together, snuggling like teddy bears.