Pipsqueak gets all the Ladies

Pip was just waiting for a package to come for his house, for it was a postcard from his grandparents in Manehattan. The young colt was expecting to have a present of fifty bits from them since they really love their grandson so much.

Word has it that the package is supposed to be at his house in the afternoon right now.

Boy, he hoped that it does come today because this is the actual date when his bits will come through mail.

One thing that made Pip worry a little was one if the mailponies that is well-known and is a regular to Pip's residence. Who would it be? None other than Derpy.

This peculiar mare was kind of a nuisance to Ponyville, for Derpy was... a little north from clever, and she was no Twilight Sparkle. What made her lovable was her naive and innocence and her sweet personality, although she doesn't know any better at most things. She doesn't really tend to cause a lot of frustration for Pip and his family because she is a regular.

Taking a sip of his apple cider, Pip was also reading some comic books to help him pass the time, and keep him from getting bored stiff like a rock. At last, after ten more minutes of waiting and reading comics, the doorbell finally chimed around the house.

Pip promptly answered and he hoped that it wouldn't be Derpy a little because of her infamous screwups, but just his luck, it was indeed, Derpy herself.

"Oh. 'Ello, Derpy." Said Pip, trying to smile as possible for her.

"Hey there, Pip." Said Derpy with her adorable smile on her adorable face. "I've got a package for you today."

Derpy then handed him a small box made of cardboard and promptly gave it to him.

"I hope I gave you the right mail this time." She remarked.

Young Pip was beginning to think that himself and he slowly opened it. It was a small pouch with a red band around it. Not only that, but there was a small scroll attached to it. He unrolled it and it read:

To our favorite grandson. We hope that you will enjoy these fifty coins we give to you to show how much we love you. Please spend it wisely, or save it for something special.

Your loving grandfather and grandmother.

The colt smiled, touched by his grandparents' kindness, and put his pouch somewhere safe in his room.

When he came back downstairs, Puo then said to the adorable pegasus mare: "thank you so much, Derpy."

All of a sudden, he felt a weight pulling him towards her. Derpy was only hugging him. "You are welcome, Pip. Oh, you are just so cute I could just hug you like a....." she didn't know what to think of That's huggable.

"A teddy bear?"

"Yeah! A teddy bear that I can snuggle with all night and sleep with through it."

About to protest against this, Pip had a realization, and he had a sly look on his face. He just found yet another beautiful mare to fuck around with sooner or later in his life.

"I think they can be arranged." He remarked slyly.

Derpy immediately let him go and aksed him: "what do you mean?"

"I can come over to your house and..." he whispered in her left ear, and her eyes shot wide like a pair of balls. A smile slowly crept on her face, and she immediately liked the idea that he was telling him about.

"Ooooooh. I like the way you think, Pip." She remarked. "But wait, what about your mom and dad? Will they be okay with it?"

"Don't worry. They will be more than fine."

"Fine about what?" Braveheart and Daisymay were right behind Pip with curious looks on their faces.

Trying to figure out a good lie to both of them, Derpy said: "Just him coming over to my house to-" then she was silenced by Pip covering her mouth with his hoof.

"Show her how to do better with mail stamps, that'a all. You know how she is having trouble with doing that thing when delivering.

Derpy was a little confused, but then she realized that he was lying for a good reason and nodded her head a yes to his folks. As soon as Pip got his hoof off of her mouth, she said: "Yeah, you know how I always have problems with those stupid stamps. It can save me from getting fired by my boss."

"Oh. That sounds very helpful." said Daisymay. "Just be back here before curfew, dearest. As always, and I know you will be back before bedtime."

"Of course, mum. Have I ever been late home by curfew before?"

"No. Of course not " said the father. "Me and your mother trust you completely."

"Good."

"Well, I would love to stay here and talk some more, but, duty calls." Then she flew away with the rest of the mail, and she was flying in a rather clumsy manner, bumping into some trees and some poles in Ponyville, much to the annoyance of the residents.

"Oh Derpy." Said Braveheart in slight annoyance. "We deeply care about you, but we simply do not understand you."

"No one does, dearie." Daisymay remarked. The father just promptly closed the door and he went back to his normal life, along with the other family members.

Five hours have passed and it was five-thirty in the afternoon. Pip went out his house after telling his folks he will be back before dark.

Derpy's house wasn't hard to find for him and Pip knew what it looked like for his eyes to know what her house was. The sun was almost setting over the horizon of Equestria, but it was alright, for Pip will have a fun evening today.

As soon as he reached to her house, he knocked on the door and Derpy answered it with a sock over her head. “Hey Pip, There you are. Come on, come in.”

“Uh, Derpy, why are you wearing a sock on your head?”

“Ummmm..l I don’t know. Trying to look beautiful for you.” Then she bumped into her coffee table.

Pip facepalmed himself in irritation and he said to her: “no no no, you wear your socks on your feet Derpy.”

“I know. I know. I’m just trying to look beautiful for you with the socks. Am I supposed to wear these socks to make your penis big?”

“Yeah but, not like this. ‘Ere, let me ahow you.” Pip had to get her to put the socks in her feet, and when that was complete, he was immediately turned on by how beautiful she looked on those garments.

“Wow. This is better, Pip. Thank you.” Derpy Said with gratitude.

“No problem. Happy to help you out, Derpy.” Before she knew it, the colt was bold and brazen enough to lick all around her lush, making her blush and smile in relaxation from this feeling. She felt like she was in heaven having her triangle being licked like that.

“Ah! Wow. That feels good.” She sighed.

“Just Relax And let me help you out.”

“Keep going, Pip. Just don’t stop.” The gray pegasus gasped again. “That feels too good. I want more.”

Pip smiled and continued licking all around her vulva. It tasted rather nice and it smelled a little bit like lemonade and some cinnamon muffin to go with it, probsvly becasue they are Derpy’s favorite food of all time.

After a brief period of time, Derpy felt her own climax about to rise within her system, and as Pip swirled his tongue around her skin, the more aroused she felt. At last, she squirted her clear, happy juice in Pip’s face like a water fountain in a park.

“Wow. That was so awesome.” She panted.

Pip licked all around his face to taste every drop of her clear liquid, and he loved every drop of it. He knew he made a Derpy very happy to climax and be touched in her insides like this.

“Thank you Pip.” Said The gray mare. “Now, it’s my turn.” Then she engulfed Pip’s cock in her mouth, and began sucking away at his hot dog. She had her eyes closed and relaxed in trying to make Pip happy and feel relaxed.

The colt was enjoying a very good fellatio and be given head by a beautiful mare like Derpy, even though there is not much going on with her in her head. Still, he was very happy with this and so was Derpy.

For the mare, this dick tasted a little like chocolate and vanilla ice cream to her mouth, and it was the reason for her to decide to go a little faster while in fellatio. Panting and sighing at his cock being tenderly sucked by a Derpy, he was relaxing in this sexy moment.

“Ah! Don’t stop, Derpy.” He said.

Before he could finish any more happiness, he felt a small pain in his shaft, making Derpy let go of him.

“Ow! Derpy, you bit me too hard.” Pip Said.

“Oops. Sorry.” Said The gray Pegasus.

“It’s alright. Just be more gentle.”

“Okay!” And she tried sucking more gently, but she was still a little too rough with the nipping, and Pip would have to correct her over and over again, but she u,tiantely did it right after a few tries.

Derpy didn’t say anything in reply, and continued with the blowjob instead to try and make him as happy as he can be. Who knows when Pip will ejaculate in her mouth and fill it up within herself. There was no telling when it will happen, but she will make it as fast as possible.

“So yummy.” Derpy Said in her brain. “Like ice cream.”

Before Pip knew it, he felt her sucking up and down his shaft more to make him cum faster. The colt’s eyes were rolling and his cheeks were flushing a brighter crimson red, then without warning, he ejaculated inside her mouth and Derpy was surprised by how much sperm he just squirted inside her, and she loved the oozing feeling.

After swallowing the whole drops, Derpy let go of his cock and panted, feeling a little tired from all that sucking. “You tasted so yummy, Pip. I can’t believe we haven’t done this before.”

“Yeah. There were so many mares and... I have life outside of that.” Pip admitted sheepishly. “Sorry about that.”

“Oh, it’s okay. No need to be sorry. You’re my friend.” Then she kissed him on his lips for three seconds to show her affection more. “Nothing will ever change that.”

Pip smiled gratefully. “Thank you, Derpy. Well, I think you know what happens next.”

“Actually, I don’t. Are we done?”

“Almost.” Pip answered. “Just stick with me. Now, let me just do this.” He slowly stick his cock inside her triangle, and it made her gasp and flush. Derpy also bit her lower lip from how nice the feeling was to be gently penetrated like this.

For a small colt, she thought that his clock was rather large to go with somepony like Pip. Still, she really loved this feeling. Before she knew it, Derpy felt Pip slowly move his cock up in down while she was in her doggy position. Small drops of sweat was running down her face and Pip was having the same thing happen to him, but they didn’t care, because they were enjoying this.

Her eyes were moving around a little more wildly than usual, and her tongue was out while drooling in ecstasy.

At last, Pip was thrusting inside her faster than before and Derpy was closing her eyes as she enjoyed more thrusting.

“Here it comes!” Said Pip. “Get ready.”

“Let it all out!” Derpy warned. “And eat some for yourself if you would like.”

As he thrusted to and fro some more, Pip felt the climax rushing back to him and let more semen out of his unmentionables. It was a heavenly and amazing time for him to endure, and Derpy was thinking the same.

Something wet, warm, and oozy was squirting inside of her and Derpy let out more happy juice as she made an orgasm. She felt so much pressure rush in her head and collapsed on her belly.

Meanwhile, Pip was ejeculating a storm inside of the mare’s vulva and felt a little tired. “Sweet Celestia.” He Said while panting. Pip tried to keep his balance, but he collapsed on his back, panting and catching his breath.

“Thank you for doing that, Pip. Sorry for biting you a little too hard before. I just don’t know what went wrong with that.

“Yes. I wonder.” The colt muttered sarcastically to himself. “I hope I made you happy.”

“You’ve made me really happy, Pip. Thank you.” Said Derpy. “At least we got to do it together. I wonder what time it is.”

Looking over at the grandfather clock, Pip noticed it was twenty past seven already, and he couldn't believe at how much time he spent doing these activities. His curfew was at eight, and he had forty minutes to get back home. “It’s seven-twenty. Boy, we really hit it off together.”

“Yeah. I really lost track of time.” They gray Pegasus agreed with him. “I guess we were having too much fun there.”

“Agreed. Time flies fast when you have fun.”

“Well, before you leave, would you like a muffin basket?”

“Sure Derpy. What flavor?”

“Blueberry.”

Pip made a gasp of excitement. “Me favorite! I love blueberry muffins.” He waited onnthe couch for Derpy to give him some of her leftovers and he felt happy to get a bonus reward from that. As soon as Derpy gave the basket to him, he smiled and loved how scrumptious they tasted, for he can hardly wait to taste these lovely muffins.

“Here you go, buddy.”

“thank you, Derpy. Mum and dad will love these.”

“And, can I have a hug?”

“Well, I suppose why not.” Then he felt a Derpy hug him real tightly, almost suffocating him of oxygen. “Ah! Too tight!” He grunted

“Oops. Sorry. I just Love hugs.”

“No problem.”