Pipsqueak gets all the Ladies

Almost a week has passed after Pip did that little special treat with princess Twilight. He and his mother Daisymay were going out shopping for any food that they were running short of in their home. The mother looked around in the farmer's market for anything on sale or at least something they would both want. Every fruit and vegetable was fresh, and so were the oats and hay.

"Mum, why isn't dad coming with us?" Pip asked curiously

"Oh he has to do he garden, sweetie." Daisymay replied. "It's not that he doesn't want to be with us, the poor chap just wants his garden to be nice and fresh for any veggies to grow so we won't have to buy food as often and save bits."

"That's true. I know how dad can be obsessive with that garden, eh?" They both chuckled. "So, do you see any tomatoes? Or maybe carrots or apples?"

"Well, we obviously have enough apples at home, dear, but for carrots and tomatoes, not so much."

"Ah."

"Oh! Here's some carrots now." She exclaimed, finding one of her items on the list. She paid a few bits to Carrot Top and she gave her the veggies for a fair trade.

"Thank you for coming, Dasiy." Carrot Top said politely. "Have a nice day. Oh! And you too, Pip."

"Thank you, Carrot. Tata." Then they headed to the tomato stall, which were also only a few bits per bundle. They all looked ripe and fresh, ready to be eaten by anypony they can come across.

After that, Pip asked "is there anything else we need, mum?"

"Hmm. Let me check my list. Hmmmmm, already got that, hmmmmm..... nope, I think we are just about done."

"Alright then. Does that mean we can go home now?"

"Yes, Pippy-Wippy." She chuckled

"Mum. Please don't call me that name it.... it's embarrassing." His cheeks blushed a tomato red. "And, there are other ponies here."

"Oh, I am so sorry if I am embarrassing you." Said Daisymay. "I just love you and you are one of the best things I can ever ask for."

"It's fine. Let's just go home."

"Agreed." Then they both happily walked back home, forgetting about that little skirmish.

While walking, Rarity, the beautiful and stunning unicorn mare that lives in and owns the Carousel Boutique, was walking towards them. "Daisymay!" She called in a sing-song voice.

"Oh, Rarity, hello."

"Hello, Daisymay. Ah, and hello Pipsqueak." She replied, noticing the colt. She can never get enough of his adorableness as much as she can handle Spike's adorableness.

"Hello, Rarity." Pip said. Then he noticed a bulge forming under him. He was stunned by her beauty and was like with Luna, Twilight, and the crusaders. He blushed a faint crimson red on his cheeks, nevertheless, he kept his cool.

"I do apologize for interrupting you, but I wanted to ask Pip a favor, if that is alright with you Daisymay."

"What for? Am I in trouble for something?" Pip asked

"Oh no no, of course not, sweetie." Rarity replied. "You're doing just fine. Besides, Sweetie Belle always told me that you ware one of Cheerilee's favorites."

Pip blushed. "Yeah, well, guilty as charged. So, what kind of favor do you want with me, Rarity?"

"Well, i am creating adorable little tuxedos for the colts in Canterlot, Manehattan, Saddle Arabia, and Zebrica. I need somepony to help me try on a sample for one of the tuxedos I am creating. So, would you like to help me?"

"Well, i don't know. What about Spike?" Pip said. "He would be more willing to help you out."

Rarity giggled. "Oh Pipsqueak, you are so funny. Spike is.... a little busy with Twilight Right now, so he Is unavailable. Besides, these are made for colts and not baby dragon's after all."

"Oh yeah." The colt was thinking about it, whether he should help Rarity with this little favor or not.

"And if you are unavailable, or if you don't want to do it, I understand completely. The decision is yous."

"Thank you, Rarity. I.... i think I do want to help you."

"Brilliant!" Rarity exclaimed with a wider smile.

The colt looked at Daisymay for approval. "Mum, can I help Rarity?"

"Sure." She looked at Rarity, and said to her "Please take good care of him, Rarity. I don't want him to burn himself out unexpectedly."

"Oh don't worry, Daisymay." Rarity replied. "I would never work a sweet colt like him too hard. Besides, the little angel won't be working like that anyway."

Pip blushed when he was called that adorable name by one of the most beautiful mares in town. "Good." he said, still blushing with a larger, brighter red

"Oh sweetness, you're turning red. It is so cute." Rarity said, noticing his slight embarrassment, which now has become more shy than ever. "Oh come now, darling. There's no need to feel embarrassed about being cute."

"Okay."

"I'll be heading home so these produce items won't spoil. You can walk home, can you?"

"Of course I can, mum. I ain't a baby anymore."

"I know I know. Well, i'll see you in a little while when you get home, sweetie."

"Okay, see you later." Then Daisymay walked back to her and hr son's home. "Alright, Rarity. Let's get to it."

"Perfect. Follow me, darling." They both went inside the boutique, and Pip noticed Sweetie Belle walking by from another room. She was always happy to see one of her closest friends besides Scootaloo and Applebloom."

"Hi Pip." She said in her cracky voice.

"Hey, Sweetie."

"What are you doing here?"

"Pip is going to be my little helper for the tuxedos for the colts out of Ponyville." Rarity answered her younger sister.

"Oh. That's good. Do yo think I can help you?"

Rarity had a horrified look on her face, and remembered the time when Sweetie accidentally threw one of Rarity's finest dresses into the fireplace of the house. She didn't want anything like that happening again, even if Sweetie just wants to help, so she replied to her "That's very kind of you, sister, but I got all the help I need."

"Okay." then Sweetie Belle went out the door to possibly hang out with her best cohorts again.

Rights for this song go to Nintendo

"Alright, darling. Now if you can just follow me upstairs, and we will get started, shall we?" Rarity said.

"Okay, Rarity."

The colt followed the white unicorn upstairs into her room and was astounded to see the decor. He remembered visiting it once, but it was more for a slumber party with his best filly friends. He couldn't even remembered what it even looked like in particular, until now.

"Now please be a dear and stand on this pedestal."

"Of course." when he got up like Rarity told him to, she pulled out her working glasses and her measuring tape.

"Now I just need to measure you with this tape, and then i will put on one tuxedo for you to see how it fits." After she measured his waist, she put on the nice looking tux on him. "Oh look at how adorable you are." she said.

Pip felt a little uncomfortable, and didn't really like the tuxedo. It was probably a good thing that Sweetie Belle, and her friends were not here to see him like this. He would be more embarrassed than he ever was in his whole life.

"Well, how does it fit?"

"It.... fits alright." he said. "but i think i look ridiculous." he replied with slight shame.

"Oh come on sweetie. You look absolutely stunning." Pip wasn't really convinced. "Pipsqueak, darling. Please look at me." she gently lifted his chin her hoof. "It's alright. There's nothing to be embarrassed about." she said softly

"There isn't"

"Of course not. Every filly in Equestria would even say yes if you asked them to do a ballroom dance with you."

Pip never really thought of it that way. Usually when he thinks of tuxedos, it would mean really boring business ponies and lawyers, but never really thought of it being a girl magnet. "You really think I look handsome in this thing?" he asked

"Oh yes. You look absolutely one of the most handsome colts in all of Equestria."

"More than Princes Blueblood?"

"Oh yes. Even more handsome than that so-called royal prince himself. I do not even know why that egotistical ruffian is apart of royalty."

Pip laughed. "I couldn't agree more. You're right. I should probably not be so cynical about this." He looked at himself a little more deeper after what Rarity said to him. "You know what? I think I do look handsome."

"See, it's not so bad. Now let's get back to the matter at hoof, shall we?"

"Right."

"Oh, and after we are finished, I will give you a very special present later."

Pip gasped. "A present? For me? What is it?"

Rarity giggled in a rather seductive laugh. "It's a surprise." She sang.

Then they both went back to work with it.

Later in the evening, Pip felt really happy about helping Rarity with the tuxedos earlier. He was very anxious to know what the surprise that Rarity mention was.

"So Pip, I would like to say I am proud of you for helpin' Rarity with her little errand." said Braveheart.

"Thanks dad. I'm always happy to help any friend that needs me." Pip said proudly, trying to create a pose that looks like a superhero.

"That's great, darling. Here's Spaghetti for dinner, my little helper."

Pip gasped "My favorite!" then he began eating his dinner. He loved the taste of spaghetti in the evening as his favorite dish to consume. After he ate, he heard a knock on the door. Braveheart opened it and it was who Pip thought it was.

"Ah, Rarity. 'ello." he said

"Good evening, Braveheart." Rarity replied to him. "Ah, Pip. Hello."

"I suppose you are here to give Pip his present?" Daisymay asked

"Yes. Pipsqueak!" she called

The colt ran up to her with excitement. "I''m here!" he exclaimed with a smiled. "So where is it? where is it?"

Rarity giggled "Hold your horses there, sweetie. It's in my house. You see, I was thinking about having another slumber party with you."

"Slumber party?"

"Hm-mmm. What do you say? would you like to?"

"Hmm. mum, dad, can I go? I promise I will be back tomorrow."

"Well, normally we wouldn't allow you to do it." said Braveheart a little uncertain.

"Oh darling, that's on a school night." Daisymay corrected while chuckling. "This is summer vacation after all."

"Oh of course."

"Very well, sweetie. You can go." the mother said kindly.

"You'll pick me up tomorrow morning, right?"

"Of course" said Braveheart. "Have fun, laddy."

"I will dad. Let's go, Rarity."

"Wonderful." Then he followed her back to the boutique.

***

The place smiled nice as ever.

"So, where is Sweetie Belle?" Pip asked

"She couldn't join us. She's already in bed. Wouldn't want to wake the little angel anyway. Besides," she gently hugged him with her face. "It's just you and me, darling."

"Oh. Okay." Pip then felt the bulge come back again. He followed her upstairs again and before he opened the bedroom door. Rarity stopped him for an unknown reason.

"Sorry to halt you sweetie, but It's a surprise, remember?"

"Oh. Right. So that means I have to close my eyes, right?"

"Correct."

Then he clamped his eyes shut.

"Now just keep it like that for a little moment, like one minute or two."

"Alright." Then they both entered her room. It smelled rather.... nice, like exotic candles with very nice scents. It was a mix of various scents from fruity, mint, to flowers, it was all so erotic to him. He heard clothes moving of some sort, and heart Rarity giggling seductively.

"Okay, sweetie. You can open your eyes, now." Rarity said.

He opened his eyes and he slightly drooled when he saw Rarity in beautiful black socks, doing a sexy pose for him in bed. This was just like Twilight when he was having a little fun with her. She had beautiful black socks up to her thighs and blinked her eyes rapidly at him. The lights in the room were turned off, and candles were lit all around, and he was right about the smell all along.

"Surprise." she purred seductively.

"Uhhh- uhh- uhh." Pip was lost for words, and was too stunned to put even one single syllable in one complete word

"Do you like what you see, darling?"

"Y.... Yes."

"Come here." She purred.

Pip did two little tiny steps, barely moving an inch.

"Oh come now, Pipsqueak. No need to be shy. Please come here."

"Oh you're right. I guess I shouldn't be so timid. It was just like Twilight and the crusaders, except it was Rarity this time. He felt more confident than before and went on the bed

"Good boy."

"Sorry for being nervous before. It just.... Caught me by surprise." He apologized.

"Oh, it's alright, darling." Rarity replied. "We all can get nervous at times."

"Good. So, what shall we do?"

"Well, first, please be a good boy and lie on your back."

The colt did what she told him to do and the mattress felt really nice, even more soft and relaxing an his own bed, or even the master bed that belongs to his parents.

"Good." Then she slowly got on him and slowly slid her pussy down his colthood, making him exclaiming a small "Eeek!" Rarity giggled at his reaction.

"That.... That feels good." He said

"Good. Now, please just stay there and relax while I bounce on you." Like she was saying, she slowly bounced herself up and down on his shaft. The colt panted as the pleasure was already flowing through him very slowly. Her pussy felt so nice and soft as if he was getting a relaxing massage on it.

He turned his head away slightly

"Ah ah ah." Said Rarity as she stopped. "Don't look away, you little bad boy."

"Sorry."

Then she continued bouncing. She jumped a little faster than before to quicken the pace of the climax.

"Ah, Rarity, I'm cumming!" The colt exclaimed

"Yes! Give me all your semen within myself." Rarity shouted.

After holding it in for a period of time, he ejaculated cum inside her wet pussy, and Rarity exclaimed with pleasure as she climaxed herself.

Pip panted, and was trying to catch his breath from all of the pressure. Rarity was doing the same thing, for all that bouncing might have warn her out already.

"Did it feel wonderful?" She asked as she was gently placing her hoof on his face, gently stroking it like a pet.

"Yeah." He panted. "It did."

"Good."

"You really look beautiful in those socks, Rarity."

"Aww, that is sweet. Thank you." Then she gave him a tender kiss on his face.

"You're welcome."

"Oh, you got a little bit if sperm on your cute penis. Let me clean that for you." She used her hoof to gently sweep it off of his head, and licked it before swallowing it. Rarity then thought of an idea and smirked a devilish grin. She gently started rubbing her socked hooves against his colthood.

"Ah! Oh yeah." He gasped.

Rarity made another seductive laugh. "You love this, do you?"

"Yes" the fabric that Rarity was wearing on her legs felt very nice, like a soft warm covers. She began to rub up and down the shaft a little faster than before. "Ah, Rarity! I-!"

"Shh, say no more, darling, say no more." She purred. "Release as much as you can." Then she opened her mouth close to his colthood, and he squirted inside it. He felt even more lucky to experience

"Thank you, Rarity."

"You're welcome, sweetie " then Rarity gave him a tender kiss on his forehead, making him blush.

The colt yawned. "I'm getting a little sleepy."

"Don't worry, Pip. Let me tuck you in bed for the night." She gently licked him up and placed him on one side of he bed. She licked her lips and without him thinking, she put his cock in her mouth, making it hard once again.

Pip grunted and struggled lightly as the pleasure was coming back to him. "Oh yeah." He exclaimed. "That feels so good!" Pip felt like ejaculating again and squirted right in her mouth, making her moan in pleasure.

"That is delicious." She said as she licked her lips again. "Here, let me give you a good night kiss now." When she blew her lips on his forehead, and flushed heavily, feeling lucky to get the girls.

"Now, would you like me to keep these socks on me?"

"Yes, please. Goodnight, Rarity."

"Sweet dreams, my little angel." She whispered n his ear. She turned out the light and the colt fell asleep. Rarity slept close to him and had an arm around him.