Pipsqueak gets all the Ladies

Four days later, Pip was relaxing his summer, reading more comic books. He read the last page of the last book he was reading and closed it, promptly putting it back in his closet. He got himself some water Then there was a knock on the door. "I'll get it." Daisymay sung from another room. When she opened the door, it revealed to be the richest filly in Ponyville.

"Oh, Hello Diamond Tiara." said the mother. "How are you on this fine day?"

Pip's eyes went wide and slight looked up from the fridge hearing that peculiar name. "Hello miss Daisymay." the young pink filly reply to her in return. Since she was reformed (Thanks to the Crusaders, who got their cutie marks at last) she has been more nicer than before, and turned over a new life of kindness and compassion to all ponies everywhere. "Is.... Pip home?"

"I'll get him for you. Pip." she called to him.

"Yeah, mom?" The colt replied to her. He didn't really need to, since the kitchen was not far from the front door of his house.

"Diamond Tiara's here, sweetie." He closed the fridge, and went to greet the former bully of his school. "Hello, Diamond." He said

"Hi Pip." She said in a cheerful tone. "How are you?"

"Doing good. How's your summer?"

"Fabulous. Just been shopping with silver Spoon and hanging out with a Scootaloo, Applebloom. And Sweetie Belle. That sort you thing. You know how it goes."

"Right. So what brings you here?"

"Well.... I was wondering if I can.... Send some time with you. I feel guilty for bullying you and your friends. I want to..... Make up for lost time, if you know what I mean."

Pip was more than happy to hear that from Diamond. He was so glad that she truly wanted to be a better pony than she was before. "Well... That's really nice, Diamond. But, wouldn't your mom get mad at you for being with a low-class colt like me?"

"Don't say that." Diamond Tiara reassured "and, don't worry about mother." She made a frown on his face with her eyes looking to the left in annoyance. "She.... Just needs to learn that money isn't everything, and that not all ponies that are not rich lie me are not what she thinks she is."

"True." Pip said "I remembered when she came to our school and called us a bunch of insignificant low-lives, like she thinks she's better than everypony else."

"I know. Don't worry, she is trying to be a better mare and try to be more open."

"But, what if she doesn't want us to hang out together?"

"Just leave that to me. My daddy has power over me two, it's part of sovereignty."

"That is true. Me, and my husband both have to come to a compromise from another in certain situations, now matter how we agree or disagree."

Daisymay was right, a husband and wife have to share their dominance with one another. "You're right. Mm." Pip said "so, can I go play with her?"

"Of course you can sweetie. Just be back here for lunch. Your father is helping me cook a real treat."

"Sure. I will."

"Have fun." The young colt happily walked with Diamond Tiara down the road to begin their little time together.

"So, how's Silver Spoon?,

"She's in Canterlot with her parents on vacation."

"That's nice." He cleared his throat, feeling a little awkward, because didn't know what to say next in particular. Finally, he said "me and my family went to the Crystal Empire on vacation few days ago."

Diamond Tiara's eyes went wide "wow, that's lie so amazing," she said "did you have fun?"

"Yeah! It was really fun. I got to see the statue of Spike next to the castle. Have you been there?"

"Oh of course." The pink filly replied in enthusiasm "it was amazing, and shiny and stuff, you know. That sort of thing.""

"Nice."

"So, Pip?"

"Yes? What is it?"

"Listen I.... I might have said this a few times before, but... I am so sorry about the way I treated you, the crusaders, and other kids and blank flanks."

"Oh, Diamond. I forgive you, remember?"

"I do. But still, I'm pretty sure some things I did were excusable." She said with guilt bowing her head in remorse. "I can at least spend a little time with you, Pip. It's the least I can do."

"Thanks."

"Anything for a friend." She made a sad smile to him. "So.... Would you like to come over to my mansion?"

Pip's eyes went wide with surprise. "Really? But- would your mother kill us?"

"No. Besides, she's not home, anyway. My dad is a little more.... Open to anypony than her." She said in a more angry voice "she can be a..... Well.... She can be a......"

"Go on, Diamond Tiara, say it. Let it out."

"An evil bitch!!" She finished. She covered her mouth in shock. "I can't believe I just said that. Don't tell anypony, please?"

"Of course. I agree with you, about your mum, anyway."

"Good." She said in relief.

"So, when do you think Silver Spoon will be back?"

"Tomorrow. Today is her last day in Canterlot. So, again, would you like to come over to my mansion?"

"Sure."

"Perfect! You will love it! It's big, and shiny. My butler, Randolph will be there will be there to let us in. He has to do everything me and my family will say."

"Good."

***

The mansion was bigger then Pip remembered on the exterior. The door opened and it revealed to be the butler himself "ahh, hello, miss Tiara." He said in a British voice. "And who might this ragamuffin be?"

"He's not a ragamuffin, Randolph!" Diamond reprimanded "he's.... My friend. Can you please let us in?"

"Of course, mistress. You may enter." The the doors opened farther back and it revealed the whole interior of the large mansion. Pip was truly amazed by this beautiful building, and his mouth went agape.

"Sweet Celestia."

"Do you like it?"

"I love it! It's truly amazing! I'm jealous that you live in a mansion like this."

"I know. It's glamorous, isn't it." Diamond strutted. "So, come on. Why don't we go up to my room and play?"

"Sure."

"Diamond Tiara!" A stallion's voice called out to her. It was her father, Filthy Rich. "What is going on here?" He asked her n a semi-firm voice.

"Oh, hello, daddy. I'm just showing Pip around the mansion."

"Oh yeah. I do remember that. I was just too busy counting my bits in the treasure room." Then he looked at the colt "and hello Pip. How might you be doing on this fine day?"

"Just fine. And you, Mr. Rich?"

"Same here, my boy."

"Listen, can you please not tell Spoiled rich that I was here? She mig kill me for it." Pip asked him nervously

"What would possibly give you an idea like that?" Filthy Chuckled

"Well, she..... Doesn't like my kind. That's all."

"Oh, Pip. Spoiled Rich doesn't hate everypony that is not wealthy like us. She.... Just thinks herself as higher than everypony else. Kind of like how you, Diamond Tiara, behaved before you decided to be nicer."

"I promise daddy, you are looking at the new Diamond Tiara."

"Good. The point is, I will not tell her if that would make you happy. But, I am saying that Spoiled is a little misunderstood. She just needs to know you a little more."

"Maybe so. Well, no matter. We're going to my bedroom if you need us, daddy."

"Okay. You kids have fun, and play nice."

"We will." The both said in unison. The two continued to the bedroom up a long line of stairs, and Pip was amazed once again by how it looked. Her room had a large diamond chandelier at the top of her ceiling. Her floor was purple and had a jeweled tiara like her cutie mark in he center of it, the bed was large and had dangling link drapes over the sides.

"What do you think of my room?" Diamond sang

"Amazing! So what should we do?" Then he heard e door shut. Diamond Tiara had a seductive look on her face.

She giggled before she said "now we will have some fun." Pip's cock began to harden again. "Aww look, it's already so big." She cooed, noticing his colthood.

"I-I-I- uh..... I can explain." Pip stammered in embarrassment. He was a little lost for words and was stuck on the spot.

"What's wrong, are you too shy to talk to me?" She invaded his personal space by clinging to him, making his cheeks blush a tomato red. "It's okay. I understand. I want you to like me when I'm like this."

"Ummm, how did you know I am starting to like girls?"

"Oh I.... You know.... I looked through the window when you were doing it with the crusaders the other day."

"Wait." He nodded his head rapidly "you were spying on me?"

"Oh no no no. Of course not." She said in mock offense. "That's not really important right now. What is important. Is that we will have a good time together like you did with Scootaloo, Applebloom, and Sweetie Belle." She began to purr like a cat would do when it's happy. Pip was starting to enjoy this nonetheless, even though she was kind of invading his personal space, he was loving it.

"Oh Diamond." He murmured. Then he felt her gently nipping his ear. "Ah! That tickles!"

"Shhh." She whispered softly. "Just stay right here. Bow, do be a good boy, and sit down on the bed."

"Okay." The colt did what she asked him to do, and sat on the nice bed. The covers were so fluffy, like the fluffiest in all of Equestria maybe.

Diamond Tiara licked her lips, and slowly engulfed his entire cock in her mouth, deep-throating it slowly while softly moaning.

Pip gasped and twitched a few times from the pleasure it was building within himself. "Yeah! Don't stop. Please." He gasped with his head back.

Diamond then gently nipped at the head of his colthood, and licked it by swirling her tongue around clockwise and counter-clockwise. "Pip, you do taste so good, and I love your cock." She said.

"Thanks." After many moments, he said "oh god, i'm cumming! I'm cumming!" Then without warning her, he ejaculated so much sperm in her mouth, making her moan

"She slowly let it out of her mouth, making some sticky wet noises, then drank it from her hooves. "Wow. That was totally amazing." She purred. She licked a piece of semen from her lip. "I'm so glad I decided to let you come spend time with me."

"Me too. And, you won't tell anypony about this, will you?"

"It's okay Pip. You have my word as a friend. A rich ponys' honor." She vowed to him. "I will keep it a secret from everypony else. I promise." Then she gave him a kiss on his lips, making him blush, and hugged him as icing on the cake.

Without warning, Pip ejaculated another load of cum again, splashing on her face like shaving cream. "Oh my gosh I am so sorry. Diamond!" He panicked

"It's alright, Pip." She said calmly "come lick it off of my face."

Pip made a smile. "Of course." Then he licked his own semen off of her cheeks, making her really happy, like he was doing something really special for her. It was kind of like a spa day with the cream the mares wear on their faces with cucumbers on their eyes to relax and unwine.

"Thank you so much, my prince." She said after he was done.

"Your prince?" Pip said with an eyebrow raised.

"Of course. I mean, I have made you happy and you did this little favor for me." She answered. "Besides," she whispered I'm her ear "I think you're cute." Then kissed him again.

"Oh thanks." He said. "And your parents won't find out about this, right?"

"Of course not. They will never know anything.