Pipsqueak gets all the Ladies

Another day has passed since Pip was having "fun" with his former bully, Diamond Tiara in her mansion. He hoped that her blessed mother, Spoiled Rich, will never find out about this. Pip didn't even want to think about it when she finds out he fucked her daughter. The rich filly was reformed enough to keep it between her and himself, so he didn't really need to worry about it, so he didn't well on about it too much.

He was back home watching TV. "Pip!" Braveheart called.

It startled him a little, but it just caught him by surprise, so it did not frighten him much. Probably because he was so focused on he television. "Yeah, dad?" He called back

His father then came into the living room with his usual warm smile. "Can you please run. This over to Fluttershy's cottage for me? I promised her this tea that she can have, all with these apple scones."

"Sure, dad. Where are they?"

Braveheart picked up the scones in a small hand basket, and on his back, a bag of herbal tea for her. "Right here. And I thought you wouldn't really carry this much tea like this, so I put a smaller bag in the basket, alright?"

"Thanks, dad. Wait! Would it be okay if I stay Fluttershy if she asked me to be in her company?"

"Well, I suppose why not. She is the sweetest mare I have met, besides your mother, of course. But, please let me and your mother know if that happens. Either you or Fluttershy must come back here and tell us that she will have you with her for a longer time."

"Got it!" Then Pip got the basket handle in his mouth, and promptly went out the door. "See you in a little while, dad!" He called with the basket handle still in his mouth.

"Bye son."

***

Pip was humming as he was coming in front of the cottage. He stopped as he knocked on the door. After a moment, ere was no answer. He tried it again, but knocked a little harder. Still no answer? He wondered where she was.

"Hello? Fluttershy, are you home? Mum and dad wanted me to give this to you as a gift from them." He called from outside.

With one last effort, he knocked one more time with the loudest knocking he can possibly do. He was taken aback by surprise when the door suddenly creaked open, and it slowly revealed the interior inside. Pip was amazed at how it looked. The decor was beautiful, and saw many holes for mice to come and go.

"Wow. This is amazing. But, where are the animals?" He thought. "I heard that she has tons of animal friends with her in the cottage." Then he had another thought "should I just go in and place the stuff anyway?" He nodded his head "No!" He thought to himself with discipline "I can't jus to into another pony's without the, saying it's alright." He thought a little deeper. "Well, I would link her to know that mum and dad are giving her these."

So he decided to slowly go inside the cottage without Fluttershy and her animal friends knowing since it was empty at the moment, but just this once, then he will stop doing it for good. He placed it on the kitchen counter for her to know, and was about to walk out the door. What made him stop was the odd staircase that led to her bedroom. Pip's curiosity was getting the best of him.

The young colt quietly went upstairs and saw her bed. It was rather big, and it looked so soft and cozy. The covers and pillows were so fluffy. Thanks to his curiosity one more, he slowly sat on the bed, and felt surprised by how comfortable it really was. It felt lie no other bed he had felt like no other bed he had laid on in his life. It was more cozy than Diamond Tiara's, or Twilight's bed combined.

"No no no." Pip thought. "I shouldn't be doing this. This feels wrong." Then he started to get a really sleepy feeling within himself. He fought with all his might, and accidentally slipped under the covers. The bed was like a sleep magnet.

"Goodnight, mommy." He said with daze before he fell asleep on this very soft mattress. He was already dreaming so peacefully. Oh, Pip could lay in this bed forever, and just sleep in it's softness until the end of time. His bones and muscles were feeling more relaxed than he would usually be when he slept at his bed.

In his dream, he was prancing through a field of flowers with Lyra and Bon Bon with bliss and happiness. Warm, and fuzzy, he was having the time of his life, running through the sunset in this summer breeze.

"We love you, Pip." They both said in unison.

"I love you too, guys." He replied in slight shyness. "Doesn't it look so beautiful out in this weather?"

"Yeah. Definitely. This field is such a sight." Lyra agreed.

"Agreed" Bon Bon added.

All of a sudden, Pip felt some soft shaking and tapping rubbing against his side. He rolled over on the bed, but felt the shaking on his other side, now.

Pip thought there was an earthquake, a rather small earthquake. It turns out Fluttershy was home, and was trying to wake him up

"Pip?" She said in her gentle, kind voice. "Pip, can you wake up, please?"

The colt sat upright with a small fright. He saw a slightly surprised Fluttershy in front of him on the side of the bed. "Fluttershy?" He said. Now he was in a heavy pickle, or so he thought he was. He picked ad didn't know what to do.

"Oh, Pip. I am so sorry." Fluttershy said. "I didn't mean to scare you. I- I just wanted to know- why you-"

"No it,'s okay. Fluttershy." Pip replied. "I needed to get out of this bed anyway."

"Not that i'm not happy to see you, but why were you in my own bed?"

"Well, mum and dad wanted me to give you that bag of scones and tear herbs in the basket downstairs." Pip clarified

The yellow pegasus remembered. "Oh right. They did say they would give me those treats."

"Yeah, and... I didn't want to. I was so curious. I mean- this place is amazing. I just couldn't resist. I knot iced you weren't home, so I decided to place it on your kitchen counter. I'm so sorry if I came in here without your permission. Really, I am. I promise you, I will ground myself for-"

"Pip." Fluttershy halted him "it's okay." She had her cute smile on her face.

"Really?"

"Of course, silly. We all make mistakes like that once in a while. Just please think before you do something like this, okay?"

"I will." Pip then thought of the day he started his new life having fun with mares. She was concerned about him about that little wet dream he had. "Fluttershy. Can.... I tell you something?"

"Of course. What is it?"

Pip was rather anxious to tell her about what was really going on with him when she first noticed it in his eyes. He slightly looked away from her, but she walked in front of him so she can have good eye contact

"What's wrong?"

"Fluttershy. On the day you were checking on me, the reason why I was feeling weird, was because i...... I had a wet dream. Alright?" He waited for a reaction. By the look on Fluttershy's face, she was quite surprised.

"Oh. I see." She replied.

"Are you mad?"

"Of course. I'm not mad, sweetie." She said warmly. She gently lifted his chin so he can look at her. "I understand now. You're just growing up. And I am so happy for you." Then she gave him an unexpected kiss, making him blush tomato red.

"I just want you to understand how I feel. I think you are one of the prettiest mares I have ever seen."

The yellow pegasus was touched "aw, thank you Pip." Then she gave him another kiss.

"You're welcome." Now his mind is made up earlier whether he should just go back or stay with her. "Fluttershy, can I stay with you for a little longer?"

"Of course you can. I would love it if you would stay here. Do your parents know?"

"No. Dad told me that if I am staying her, either you or me must go to my house and tell them that I am being here a little longer."

Fluttershy had an idea. "I can go over there and tell them if you would it."

Pip grew a smile on his face. "Sure. I'll come with you."

"Wonderful. Maybe that would be a good idea."

"Hey, I wonder, where were you and the animals?"

"We were just having a picnic together and they wanted to go swimming in The lake not far from my cottage. Oh, it was so fun."

"Oh. Well let's go tell mum and dad then, shall we?"

Fluttershy giggled "of course." Then they both walked side by side down the stairs out of the cottage to Pip's house.

As they were walking down the road, Pip said "so, do you think they might let me be with you?"

"I'm pretty sure they will. I know them very well, and we have been friends for a very long time since the day they moved here from Trottingham."

"Yeah, you're right. They know you more than I do. Of course we are friends, right?"

"Of course we are. Why wouldn't we be?" She winked at him.

"Touche."

It was many minutes later when they reached his house. Fluttershy was the one who knocked on the door. "Oh, that must be either Pip or Fluttershy, my love." Said Braveheart

Daisymay went to the door with him and saw it was both Pip and Fluttershy at once. "Hello, Braveheart. Hello, Daisymay." Fluttershy greeted warmly to the parents.

"Hello, Fluttershy." They both said happily. Then they both looked at Pip with their same smile on their faces. "So, tell us, chap. Will you be staying with Fluttershy a little longer?"

"Yeah. Definitely." the colt replied.

"Listen, Pip wants to stay with me for the rest of the day. Would you be alright with that? He really wants to be with me today." She made puppy dog eyes that was far more adorable than anything in the whole wide world of Equestria would ever be.

The parents were thinking of it, and thought if it would be a good idea for Pip to stay at her her cottage for one day. Themselves and Fluttershy know eachother very well, after all.

It was a little while and Pip was worried that his parents would deny his request. After a little while, the colt said "Please mum and dad? I really really really want to be with her." then he mad the puppy dog face.

Finally, the parents made an agreement, and his father said "Well, alright." with a smile. "Just please be careful over there. And remember, it is for the whole day."

"Of course, dad. Thank you!" Pip hugged his parents tightly. They both chuckled

"Fluttershy, I know this may sound like a stupid question, but you will take good care of him, right?"

"Of course. I'm good with kids almost as I am good with animals."

"Thank you so much. And Pip, please be on your best behavior. Now, we know you do, because we have always been proud of you."

"Thanks, mom."

"Well, come on, Pip. Maybe I can make you a snack when we get back."

"Brilliant! See you tomorrow, mum and dad!"

"Bye Pip, bye Fluttershy." the parents replied in unison as they were walking back to Fluttershy's place. "Oh look at him." Daisymay said with a a tear in her eye. "Our little Pipsqueak is growing up."

"That he is, me darling. That he is."

It was a little later in the evening. Pip was excited that his parents happily accepted Pip staying with Fluttershy at least for the rest of the day earlier.

These two were ever so happy that they were spending time together on this very day. Moreover, Fluttershy was perfectly happy knowing what was bothering Pip the other day.

The happy colt was just relaxing on the couch sitting next to her. The animals already had their dinner for tonight and were all happy to not have empty stomachs to sleep with. "Thank you so much for letting me stay here, Fluttershy." He said

"You are very welcome, Pip." She replied. "It's the least I can do for a good friend." then she made another wink at him.

"Oh, and can you please not tell mum and dad that I was.... snooping in here, please?"

"Don't worry. I won't tell anypony about this." she promised. "It will be between you and me."

"Thank you."

"Oh, I almost forgot the tea." then she went into the cupboard to fetch herself and Pip some of that herbal tea from the basket earlier. While she wasn't looking at him, Pip was looking at her adorable, beautiful ass. He drooled mildly and felt his cock getting big once again. Her humming made it even more erotic.

When Fluttershy turned back to him with a book in her mouth, she noticed Pip covering himself, slightly looking away from her.

"Pip, are you alright?" she asked him with concern

"Oh yeah, yeah, i'm just fine. Why?"

"You're... covering where your crotch is." she pointed.

Pip could definitely not get his mind off that beautiful ass he had just seen. It was already probably too big for him to cover around his lower area anyway. He sighed. "Fluttershy." he said "Ever since the wet dream, I.... I... I have been having thought that mares like you are so beautiful. I learned how they can be.... happy from Princess Luna."

"Oh? what do you mean?"

"I.... learned about... Sex." he confessed. He blushed a more darker red just saying that

Fluttershy then blushed tomato red herself. A kid his age knowing adult pleasure? She did find it a little unusual, and she realized that Pip.... Wants to have fun with her is all. "Oh Pip. It's alright. I actually noticed it."

"Huh?"

"Twilight told me how much fun you had with her the other day. She said that you were really happy to do this for her."

"So, you're not mad then?"

"Of course not, Pip." She replied softly. "I would never be mad at you for that. It's perfectly normal that you are going through these kind of events." Then she had a sly idea of her own as well. "Come upstairs. I want to show you something."

Pip then followed her back upstairs, and stood there waiting for something to happen next. The yellow pegasus did not change facial expressions and kept her seductive bedroom eyes. "Now, just sit right there on the bed."

Then the colt did what the yellow pegasus politely asked him to do. More sexually excited abo this, he can hardly wait what will happen next.

"Now, close your eyes, Pip." She instructed.

"Yay, here we go again." He thought. He kept his eyes closed for a long minute as he hears the sound of changing clothes again. Pip could already sense ore sex already.

"Okay, you can open them up." She said. His jaw dropped when he saw the yellow pegasus in a sexy. Light-green unitard. It was like a Lyra when she was wearing a unitard, but it was white. She fluttered her bedroom eyes and was smiling "how do I look?" She asked seductively

"You look really beautiful, Fluttershy." He replied. He began drooling mildly again

She giggled "aww, somepony' getting really happy." Fluttershy sung "she turned around and showed him her beautiful ass. Like Lyra when she was wearing a unitard, Fluttershy's ass was also beautiful even in that suit. "Do you like what you see back here?"

"Yeah." He flatly stated. "I love it."

"Go on ahead, rub it." She said.

Pip got off the bed and walked up to her, and got a good look of her beautiful ass. He softly and gently rubbed all over it, making her moan

She said in bliss "hmm, yes. Right there, Pip. Hmm." Not only was Pip enjoying this little activity, but Fluttershy was taking the same pleasure he was. His hooves were nice as he felt them rubbing her backside

"It feels so nice." He thought. "Wow, I love the way it is."

Hmmm, alright, I think that's enough." Fluttershy said. Pip stopped what he was doing to keep her satisfied. " thank you so much. Now, please sit back on the bed."

"Sure!" Young Pip sat back on her mattress. Fluttershy crawled on the bed all slow and sexy-like. She looked at his large cock

She said "it's so big, yet so soon. I think you are really getting hungry." He smiled nervously " well don't worry. Let me help you with that." She licked her lips and slowly engulfed his colthood in her mouth, making Pip gasp in ecstasy

"Oh god. Oh god. Yeah! That- ah! Feels more like it! Ah!"

Meanwhile Angel was eavesdropping and felt horny himself. The bunny then began to masturbate until he squirted cum of his own on the floor. He was being a rather real pervert watching this happening since this was a private moment nevertheless he walked downstairs when he saw harry sleeping on his bed (which he hates really much)

"My goodness." Fluttershy thought, still sucking. "Pip's cute Penis feels so amazing. For a little colt, it feels like it is grown up."

Looking at her beautiful ass while enjoying this fellatio was so exciting for him. Feeling more and more happy. Then, he felt another orgasm coming his way once more. "Fluttershy! I'm gonna cum! Ahh!"

The yellow pegasus stopped and felt. Cum poured in her mouth, there was so much that it was leaking out of her mouth on her bed sheets. "Mmph!" Fluttershy swallowed every single drop of it down her throat. "Oh my, you really ejaculated so much. Ver good job."

"Thanks, Fluttershy." Pip panted. "Did I really do good?"

"Of course you did, sweetie." Then he and Pip made contact with lips to lips. Wrestling their tongues and kissing, they did that for a long two minutes.

Was there anything better than having sex with a beautiful mare like Fluttershy? For him, this is his new favorite activity. For Pip, it was never enough to be a lady's colt. It was always the cute ones the mares fall for.

They both rested on the couch with Fluttershy cuddling with him like a teddy bear.

"Oh, I know what else we can do to pass the time." She said with an idea. "Now don't go anywhere, Pip." Then she got some ripe out of the closet, along with a large, ticklish feather, and some small rubber pink ring for what reason Pip doesn't know. "Now you might want to hold still for juuuuust a minute."

She tied the rope around his wrists and ankles, and put a pillow below him and under his head to make him more comfortable where he would sit. Then he felt Fluttershy trying to put the ring through his shaft "whoa whoa whoa! What are you doing?" He asked, panicking a little

"Shhh, it's okay. It won't hurt you. This is a cock ring. It helps you hold back your semen for longer periods of time."

"You mean you don't want me to come?" He asked

"Don't be silly. Of course I want you to come. I just want you to eniy the pleasure of it first. I know you love the feeling of it, don't you?"

"Yeah. I do"

"Don't worry, I won't let it be on your cute colthood forever. I'll give it off when I decided that you can noblomger take it. Alright?"

"Okay." Then he felt the cock ring go down his shaft, and it felt rather ticklish.

"There, now you can't cum even if you want to do it." She cooed. She started to tickle him with the feather right on his cock like Lyra did to him, except it was from her hoof since she doesn't have a horn.

Pip gasped and moaned as he was feeling the feather tickling his sensitive skin. Fluttershy kept seductively giggling as she was tickling.

Ton make it more erotic, she would use her tail to use it, and turned around in a sexy pose so he can see her ass while she would do it.

Pip felt the sensation coming back just watching and feeling this. However, he could not cum now because of the cock ring thst's holding him back. He kept on twitching and gasping and moaning as he felt more tickling and watching her beautiful poses while using her tail to use the feather.

"Are you having fun, sweetoe?" She whispered in his ear.

"Yes!" He said in ecstasy. He stuck his tongue out a few times as he was still feeling the powerful urge to ejaculate some more. He saw a small amount of semen leaking from his head, slowly dripping on the bed sheets, staining it. "Ah! Ah, Fluttershy, can I cum yet, please?"

She giggled again "not yet, Pip." She sang softly. "Just wait a little more."

"O-okay! Ah!"

Next, Fluttershy pulled out a large, fluffy looking pink paintbrush. It looked more ticklish than the feather. She began to use this tool to make him even more excited.

This kind of felt like torture, but Pip loved it of course. He loved every feeling of it. After a semi-long period, with the tickling, sexy posing, and giggling, Fluttershy decided that Pip coukdn't take it anymore. "Here, let me free you, but son't cum yet until I have free you, alright?"

"Ah! Okay!" She untied the ropes. More and more cum began to spill on the bed, and Fluttershy gently pulled the cock ring off of him.

Then with a devilish smile, she giggled as she turned around, and used her tail to tickle his cock again teasingly.

While looking at her ass in the unitard, Pip ejaculated even more cum than he had ever did before. After that, he still felt like cumming. Then Fluttershy engulfed his penis in her mouth again, swallowing every lost drop of semen there was.

After many more ejaculations, Pip was done. He collapsed on the bed, feeling very tired from the pressure rushing through his small body.

"Are you okay?" She asked him.

"Yeah." He panted. "I am feeling just fine. That was amazing!"

Fluttershy giggled "good. Good. I did all of that for you Pip."

"I know. And.... thank you so much."

"You are very welcome, you sweet little angel." Then she gave him one final kiss, on the forehead this time. She laid beside him, never leaving his sight. Fluttershy thought he was so cute when he is like this.

"Fluttershy, can you please keep that unitard on?"

"Of course I will, sweetie. Anything for you."

"Good"

The yellow pegasus snuggled with Pip gently and said "I love you, Pip."

"I love you too, Fluttershy."

They both cuddled with eachother side by side. This might have been one of Pip's best experiences in his life yet. The made one last nake-out for the day before they continued to snuggle.