Pipsqueak gets all the Ladies

by MetalBrony823

Pip and Sapphire Shores/ her dancers

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Being back home in Ponyville, Pip was out for a little drink with Applebloom, Scootaloo, and Sweetie Belle in the cafe. The young colt had himself some root beer, Sweetie Belle had some pink lemonade, Scootaloo had some apple cider, and Applebloom had some iced apple juice in a glass. Inside, Pip already ate all his drink fast, and went to get a free refill, for he loved the taste of Root Beer, especially with ice to keep it cold.

"So how was Manehattan, Pip?" asked Scootaloo. "Was it fun?"

"Very fun." the colt replied happily with a loud burp. It was loud enough for everypony in the cafe to hear it, and they all stared at him in surprise. He covered his mouth, realized what he accidentally did, and said "Pardon me." And everyone didn't really stared at him anymore, and went back to their meals.

The girls themselves were impressed by this, but mostly Scootaloo, considering the fact that she is a hardcore tomboy type of filly. "Wow, that was so cool." said she. "But watch this." and she was about to take a big sip of her cider to get a big burp, but she was stopped by her two other friends

"No no," said Applebloom. "No need to do that, Scootaloo. Seriously, don't."

"Aww."

"Did you see any beautiful mares while you were over there?" asked Sweetie Belle.

Pip couldn't help but flush just thinking about how much fun he had with many beautiful mares while on vacation to the big apple of Equestria. "Well.... yeah. I met so many mares there." he replied. "I met your aunt Orange, Applebloom."

"Really? Was she nice to you?"

"Of course she was, silly. How can anypony resist my handsome face? I mean, look at me. No mare can ever try and think hideously of me and me beautiful face." the girls couldn't help, but laugh at his remark. "What?" Pip asked. "Don't laugh at me."

"We're not laughing at you, Pip." said Applebloom. "We're laughing with you."

"You certainly are handsome, Pipsqueak." said Sweetie Belle. "Anyway, anypony else you meet in Manehatten?"

"I met.... Coloratura there, and she was very nice to me too."

All three fillies gasped with surprise and excitement. "The Coloratura?" said Scootaloo. "The singer? Oh my gosh, you actually met her?"

"Yep. I thought it was a great honor meeting her back in Manehattan. I honestly didn't expect to meet her in the flesh like this. She just surprised me in the Bowling alley when I was out with me dad. Let me tell you, I had quite a blast with Coloratura when I was on vacation over there."

"Wow, lucky you." said Scootaloo. "I wish I could have been there with you."

"We already met her, Scootaloo." said Sweetie Belle.

"I know, but still, I love her music. Especially since she is switching to rock and metal now."

"I couldn't agree with you more, Scootaloo." Pip agreed. "To be fair, I think that how she is doing her music now is way better than she was before when Svengallop was her manager. Thank Celestia that he is not in her life anymore." and he took another sip of his root beer.

"Hey look, Everypony!" said one of the mares eating inside the restaurant. "It's Sapphire Shores!" many patrons gasped and immediately went outside to see if the pop star was really outside. They all looked to see Sapphire Shores, the Pony of Pop, who has indeed stopped by Ponyville for a visit. Some paparazzi were starting to pester her with interview questions, but they were shooed away by her bodyguard.

The crusaders (mostly Applebloom And Scootaloo) were really excited in her usual attire which consisted of a sparkling dress and skirt, and a shining top hat. “It’s her! I can’t believe it!” Said Applebloom.

“Me neither!” Scootaloo agreed with her. Pip and Sweetie Belle weren’t really so impressed to see her back in Ponyville, mostly due to Sweetie Belle preferring show tunes, and Pip just not being a big fan of that kind of music.

Young Pip just went back inside and just ignored her, well, he tried to ignore her, for she looked so beautiful in that kind of dress, and he kinda wanted to fuck her like he did with other mares, too. Still, he decided to buy an ice cream cone for himself to eat from as his dessert.

“Pip. What are you doing in here?” Asked Applebloom. “Aren’t you gonna meet Sapphire Shores?”

“Nope.” Pip Said. !i a, certainly not a fan of her music.”

“Well whatever.” Said Scootaloo. Then she and Applebloom went back outside to look at her some more.

"I feel the same way, Pip." Said Sweetie Belle, sitting back down next to him. "I'm not a fan of her music either."

"Heh. Guess that makes two of us, eh?"

Sweetie Belle chuckled. "I couldn't agree more." And she bought an ice cream of her own. “She’s probably here to ask Rarity for some new clothes or suits for her and her dancers for music videos.”

“You did say that she is one of Rarity’s biggest clients.”

“Yep.” After they were both finished, they went out of the restaurant, and went decide to go back home. Pip really didn’t like the music from Sapphire Shores, and tried walking as fast as he can back home so he would’t Have to deal with her.

Still, he thought she had a beautiful body and a beautiful face to go with it. Despite her being beautiful, he still didn’t like her so much, and he was about to be close to home, when the pony of pop noticed him walking away.

She decided to walk over to him, and her bodyguard went with her as well to prevent any more harassing paparazzi from pestering her some more. She trotted over to him, and Pip found himself walking next to her on the way home.

“Hello there.” Said Sapphire, trying to be friendly to him.

“Hello.” Pip replied flatly. “You’re Sapphire Shores, Right?” He Asked her curiously.

“That I am, sweetie.” She replied. “I hope i’m not bothering you at a bad time, but what’s your name, homeybunch?”

“Pipsqueak.” He muttered very quietly.

Sapphire didn’t really get all that, and said “I’m sorry, baby. What was that?”

“I Said: my name is Pipsqueak.” The colt repeated a little louder than before.

“Oh, I see. Well, I think that’s a mighty fine name for you.” She sang in a beautiful voice. “I really like ya, Pip. Where you heading anyway?”

“Home.” The colt said flatly to her. “Look Sapphire, nothing against you, us I am not really fond of your music. That’s just my opinion.”

“I really like a colt who is as honest as you, Pipsqueak.” Said Sapphire. “And that’s okay. I don’t force somepony to love my music.”

"Let's just leave him alone, miss Shores." said her bodyguard in a macho voice. "He doesn't really look interested."

"No, it's alright, sir." Pip said. "I don't mind."

"Nevermind Macho Mustache." Said Sapphire. "He has trust issues."

"No worries."

"Well, it was nice meeting you, Pipsqueak. I need to get going and stay in the hotel. I expect Rarity to design my a new line of costumes for my new music video."

"Well. Nice meeting you, Sapphire." Said Pip as he was getting close to home. Sapphire had a sly smirk on her face while he wasn't looking, and she and her bodyguard went to the hotel to check in.

To be honslest, Pip thought it was nice to meet a beautiful, famous mare like her, but still, he didn't really like her music as much as Coloratura's new style.

On the inside, the colt also hopes that he would get to have the opportunity to fuck her when he gets the perfect chance to do so. But, he decided to let nature take
It's course on this, and not rush such an amazing oppurtunity.


It was in the evening, and it was almost Pip's bedtime. For he was just done brushing his teeth before flossing them.

"Pip, are you almost ready for bed yet?" Daisymay called out to him from downstairs

"Almost, mum." Pip called back to her. "I just need to tinkle first."

"Alright. I'll tuck you in as soon as you leave the toilet."

As the young colt was finished with the bathroom, he went to his bedroom, and his mother was more than ready to tuck him in bed. Daisymay gently laid him down, and put the covers over his body.

"Goodnight, Pip." Said the mother. "Have pleasant dreams."

"You too, mum." As soon as she exited the room, and flicked the lights off, Pip immediately went to sleep.

It was just about midnight when Pip felt himself being carried away by somepony, like he was riding on someone's back on his or her back in his sleep.

Young Pip was too tired to even notice what was going on, too tired and drowsy to even think straight. He just sighed soundly in his sleep as he was being mysteriously carried off.

After a while, he heard a voice whisper in his ear in a sing-song tone of voice. "Wakey-wakey, Pipsqueak. Wakey-wakey."

The colt began to stir, and slowly awoken from the dream world. He was in a nice hotel room, like a very nice and shiny hotel room with a nice, sparkly chandelier with diamond bulbs.

Sapphire shores was in the room, and she was wearing a light-blue unitard with her hair down. "Ah, you're awake." She said.

Looking around. He saw four other mares with the Pony of Pop. One was very slender with a large, orange afro on her head, another one with a long, blue mane going down her head with a pink coat, the third, a blue earth mare with a blue coat and a darker blue Jane and tail with a headband. She had a yellow sleeveless unitard as her attire, and she looked rather cute, and last, a light blue mare with a pink mane ant tail. Almost all of them were earth ponies, except for the spender mare with the afro, who was a unicorn.

"Hello." Said the mare with the headband. "I hope we didn't scare you."

"So, you're the one Sapphire here told us about." Said the mare with the afro.

"Yeah, sorry if we brought you here while sleeping."

"Sapphire Shores?" Asked Pip. "What's going on 'ere?"

"We brought you here to make you the happiest colt alive, if you know what I mean." She had bedroom eyes, and kissed him on the forehead. Pip flushed, and his cock grew even bigger, turning even harder as well. "Ooh, I see you're already turned on. Thanks to my maaaaagic kiss."

"How did you know I was... looking for love?" Asked the colt in confusion

"Call it a hunch."

"Sapphire has a gift to tell whether a stallion is in love with her or not." said the one with the long hair down her mane. "And she said you thought she was one of the most beautiful mares in the world."

Pip flushed hearing that, and made a small chuckle while rubbing the back of his head with a sheepish smile on his face. "Guilty as charged. I mean, you have a beautiful body, Sapphire. And of course, you ladies are all beautiful and pretty as well. The mares all giggled and laughed.

"Aren't you a sweet little colt?" said the one in the yellow unitard. "I guess introductions are in order: My name is Ocean Wave, and it's nice to meet you."

"Foxxy Trot." said the second dancer.

"Blue cutie." the third one said

"And I am Shuffler Singer." The fourth and final one concluded.

"It's nice to meet you all too." Pip said. He promptly got on his feet, and he couldn't help but ask Sapphire Shores: "So, now that i'm here. What do you think we should do first?"

"I was thinking about that." said Sapphire with a sly, devious look on her faces. "Prepare yourself, honey. We'll make you the most satisfied colt ever." The other dancers had seductive looks on their faces as well.

"Now, don't worry if we do this." Said Foxxy Trot. Then she pulled out a rope to tie him up.

"Ooh, nicely done." The lead singer complimented her friend. "You doing alright?"

"Yeah. Just fine." He was bound by the rope on his front ankles, and another one tied up his rear ankles.

Sapphire licked her lips. And she turned around. She used her tail to tickle his cock and scrotum.

This made Pip chuckled from the ticklish feeling.

He was squirming, which made Sapphire laugh in amusement. "Where are you going, sweetie?" She asked teasingly. As she kept on tickling his cock and scrotum, Pip let out some semen of out himself, squirting on the floor with the sound of dripping heard.

Sapphire was very impressed by how much cum Pip can ejaculate from so much pleasure like this. She and the other dancers all knelt of the floor to lick the drops of his semen.

"Hmmm, you taste so good." Said Blue Cutie.

"Thank you." Pip panted. However, Sapphire instantly put his cock in her mouth, and began ducking away on it.

She giggled and chuckled as she was performing fellatio, and it didn't take long for her to feel him squirt some semen in her mouth.

"Oh Celestia." Pip remarked in ecstasy. "That feels too good.

"My turn." Said Foxxy Trot. She licked her own lips and began nipping on Pip's scrotum very gently like a love bite. The colt grunted and flinched at the feeling. "You like that, kiddo?" She asked him

"Yes!" Pip exclaimed while gritting his teeth.

"Good." Foxy then used her foot to press against his cock and it made Pip ejaculate another load of his sperm. Before the drops could hit the ground, she used her mouth to catch it and taste it like a filly enjoying the rain.

"Nice. My turn, now." Said Ocean Wave. She knelt down on her belly next to him, and licked her lips tenderly. Blqithout warning, Ocean locked her lips against his, and it tasted like strawberry a little. She also began rubbing his cock very gently with her right hoof to further the pleasure for him.

They wrestled their tongues for an extended period of time, and Ocean didn't stop rubbing his penis. After a while Pip grunted and let our more cum.

"That's great." Ocean remarked. And an idea popped in her head with a sneaky smile creeping on her face. "I got an idea." She said. She pulled out a rubber cock ring in the color of pink, and she gently slid it down his shaft.

"Good thinking, Ocean baby." Sapphire complimented her.

"Thanks." The ring went all the way down his shaft and was pushing his scrotum down a little. "Try and last longer. Okay?" Then she turned around and showed Pip her booty. And it looked nice, even under a yellow unitard like this. She used her own tail to tickle his cock with no mercy. She giggled as she was seeing Pip struggle like this.

It was good for Pip, because he can have some more ecstasy go through home and stare at Ocean's ass while being tickled like this.

The dancer slowly got back up and began walking around him slowly to show him her beautiful body as she kept on tickling him.

"Wow, your holding on for a long time, sweetie. I'm impressed." Said Ocean.

"I'm- ah! Glad I am making you happy." Pip grunted. He began to slowly feel the climax rushing through his system again.

"If you're happy. I'm happy, too." Ocean remarked warmly. She sat down next to him on the left, and tried to give him as much company as she can give him while tickling him with her tail. "Just stay with me longer." She murmured in his ear

"Yes, I will."

"And tell me," said the dancer. "Are you from Trottingham?"

"Yes. Ah! How did you know that?"

"We have all been there countless times before while touring." Said Ocean Wave.

"That makes sense. Oh!"

Sapphire and the other dancers decided to join in on the penis tickling with their own tails

"This is so fun." Said Shuffle Singer. "We should have done this with you a long time ago."

"I could not agree with you more, Shuffle." Said Blue Cutie in agreement.

It was all so much for him to handle, and the climax was rushing faster than before within his cock.

They were all laughing and giggling as they all saw a few drops of semen trying to escape from his dick

Drops of his happy juice were oozing down his shaft, and he was grunting while gritting his teeth from all of this ecstasy.

It went on for another thirty minutes, and Pip's cock couldn't probably handle more of this much longer.

"Okay ladies," said Sapphire. "I think Pip might explode if we keep this up. Ocean, I think you should do first dibs since this was your idea to put the ring on his cute penis."

"Thank you, Sapphire." Said Ocean Wave she licked her lips again. And said to Foxxy Trot: "foxxy. On the count of three, get the ring off of his cock so I can get a taste of all his semen as he will squirt. Poor baby needs to let it all out."

"Not a problem." Said the mare with the orange afro.

As soon as Ocean Wave counted to three, Foxxy Trot used her magic to get the ring off of Pip's shaft. It was the perfect opportunity for Ocean to put Pip's cock in her mouth, and enjoying the warm. Liquidy taste of his semen squirting inside of her. Both of them were moaning in pleasure, and Pip squirted inside of her like ten times.

Ocean never got tired of the taste and she smiled as she was tasting more and more drops of his cum oozing in her mouth.

After she was done, Sapphire had a thought. "Okay, Pip," whe said. "Now it's your turn." They all took off their clothes and they were all naked.

"You first, Sapphire." Said Pip. He happily penetrated inside of Sapphire Shores' pussy with his cock while she was in a doggy position.

The pop star stuck her tongue out in happiness just enjoying this type of experience.

"Who knew that a little colt like you would have such an amazing and gigantic penis like that."

"It's a gift." Pip remarked

"Damn right it is." Sapphire agreed with him. "Now don't stop."

Pip penetrated her even harder than before, not to mention faster, and he ejaculated inside of her, both of them letting out a loud orgasm in the process.

After he was done with Sapphire, Pip moved on to Ocean Wave, and she was enjoying it just as much as Sapphire did. "Oh my Celestia." She remarked while panting. Sticky sounds were heard as he kept on penetrating her more and more, and another climax was coming on inside of him

"Here it comes again!" Pip warned.

"Let it all out!" Ocean exclaimed. Pip did just that, and let out more semen out of himself. Ocean's vagina was being filled with so much of his cum, and she let pit an orgasm of her own.

After her was Foxxy Trot, then Blue Cutie, and Shuffle Singer for last and they all had a wonderful time having Pip cum inside of their vaginas.

They all laid in bed together as a harem. And Pip was liking this. Yep, he was glad he was "abducted" in the night to have so much sexy fun with another music star like Sapphire Shores and her dangers all together.

"Did I make you girls happy?" Pip asked them

"Of course you did, sweetiepie." Sapphire replied. "That was so amazing."

"Yeah. I'm glad you came here. And I hope we didn't throw too much at you." Said Ocean Wave.

"No. Of course not. I love doing these kind of things."

Pip felt more than lucky to have fuck with these pretty mates in one harem like he did with Photo Finish the other day.

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