The Confession of Pipsqueak
Nightmare Night. Such a lovely night for Princess Luna. It was one of her favorite nights of the year. Not because of the festivities though; yes, she enjoyed the little games and such but other dark things were done during that night that make her shudder and are better let unsaid. No, she enjoyed it and came to Ponyville for it because of him. She could still remember her first Nightmare Night all those years ago, after returning from her banishment. It had been his first Nightmare Night also and he couldn't have looked more cute in his little pirate out fit.
It was because of him she scared the children every year, because he hadn't been afraid like the others. He was the reason she kept coming to scare, to fulfill her promise to him. Over the years he had grown but still she came, regardless of his age. She claimed she did it to still fulfill her promise and that was the reason she was flying towards the little town of Ponyville now. The reason she came every year but this year...... this year would be different.
The Princess and Her Friend
Pipsqueak fidgeted in front of the mirror for a few more moments. He tried to fix a few stray hairs of his mane that just refused to cooperate, no matter how much he tried. He tried one more time to slick back those few last hairs but to no avail. He huffed angrily and messed up his hair all over again. What's the point anyway? They never go down.. he thought. He messed his mane more into what he called 'organized chaos' before stepping back from the mirror and looking over himself one more time.
The tiny colt had grown into a young stallion over the last twelve years. He had grown considerably over the course of that time, standing at only a few inches shorter than Big Mac was. He had also built up a good amount of muscle that helped define his body more. His voice had changed from the small, high pitched sound to a deeper set tone but still held the sincerity and kindness that any good pony should have. He had turned into quite the eighteen year old.
Tonight he wore no costume, he had stopped wearing his tiny pirate attire years ago. Instead, he wore a simple leather jacket that would help block some of the cold. This Nightmare Night was supposed to be a little more chilly than it usually was and he didn't want to be freezing all night. Checking himself over again, he nodded, satisfied with how he looked, then turned and exited the bathroom.
He trotted down the stairs of his house and headed for the door. As he opened it, he yelled back, "I'm going out, I'll be back later!"
"Ok, don't be out past midnight!" his parents shouted back from the living room.
Stepping through the door, he shouted back, "Ok!", before shutting the door and trotting to the street. As he got to it, he turned in the direction of the center of town and started towards the festival. As he walked along, he mulled over in his head what he would do. Ok, ok, you've got to do it tonight Pipsqueak. You chickened out last year but not this time, this time, your going to tell her.
He continued to repeat this inside his head, trying his best to calm his nerves that were already starting to rise. He yelped in shock as Pinkie appeared in front of him and broke him from his repetitive thoughts.
"Do you have any candy?" she asked, a hungry gleam in her eye.
Pip stared at her for a moment before he sighed. Pinkie Pie did this every year: she dressed in a chicken costume and went around gobbling up any candy in sight. He looked at her as she started to cluck like a chicken and get jerky with her movements.
He sighed again and said, "No Pinkie, I don't have any this year. Sorry 'bout that."
She stared at him for a few seconds before saying cheerfully and with a grin, "OK!"
With that, she darted off in another direction, in search of more delicious sweets. Pipsqueak couldn't help but chuckle a little at Pinkie's antics. She never did change he thought as he stared walking again. Soon, his previous thoughts assaulted his brain and threatened to over load it.
Only the sweet sound of the festival pulled him from his nervous thoughts once again and he looked to see that he had arrived. All around were games and food carts, ponies walking here and there, talking and laughing with cheer. He joined them, his fears temporarily forgotten among the festivities of the evening. He saw both old and new friends, mostly old.
He saw Featherweight and Scootaloo, leaned against each other and their wings draped over the other. He saw Rumble and Applebloom sharing an apple pie together, giggling and occasionally rubbing muzzles. He saw Spike and Sweetie Bell trying to bob for apples with varying degrees of success. He stared at them all with both sadness and excitement. Hopefully, by the end of the night, he would be like them.
He wandered aimlessly for a few more minutes before giving up on trying to dispel any anxiety and went to talk to a dear friend of his. As he headed for Fluttershy's cottage, he looked up at the night sky, searching for something, or somepony. Reaching the door, Pip knocked lightly on it and stepped back.
A few seconds passed before he heard an almost whisper from the other side, "Who is it?"
"It's just me Shy, I was hoping I could talk to you for a minute" Pipsqueak replied.
The door opened and revealed the yellow pegasis. The normally shy pony wore a gentle and warm smile on her face and said, "Oh Pip! Of course you can, please, come in."
Thanking her, Pipsqueak entered the cozy cottage and sat on the couch. Fluttershy sat beside him and said, "Now, what seems to be troubling you?"
Pip opened his mouth to say 'nothing' but he shut it almost instantly, Fluttershy always knew when something was wrong with you.
He sighed and said, "Well Fluttershy, I have a problem. You see, there's this....." He wasn't sure if he should say 'princess' or not, so he settled on, "...mare that I've had feelings for and I've tried in the past to tell her but I've always chickened out... So I was wondering if you could help me a little..."
Fluttershy looked him for a few moments with a knowing smile on her face. Finally, she said, "Well, what's this mare like?"
"Well.... She's sweet, kind, compassionate, beautiful, and just a little different" Pip said with a small smile.
Fluttershy, still smiling, shook her head and said, "So, do you think Princess Luna feels the same way for you?"
Pipsqueak reeled a little in shock. "B-but... how?!" he asked, still shocked she had figured it out.
She laughed and said, "Pip, when you're the Element of Kindness, you tend to know when ponies show extra special kindness to each other. I've noticed a kindness between the two of you over the years that I have not seen in a long time... It has the potential of becoming something more. If you want my advice, then heed me now: tell her how you really feel. You never know how she will react in turn."
Pip fell silent for a few minutes, pondering what she had said. After a few he realized that Shy was right: he didn't know how Luna would react to his confession. With any luck, she would feel the same about him and if not.... well, at least he tried.
"Thanks Fluttershy, I needed to hear that" Pipsqueak said as he hugged her tight then started for the door.
As he left, she looked at the picture of her and Big Mac hanging against the wall, snuggling together, and murmured with a smile, "You're welcome."
As Pipsqueak headed back towards the center of town, he formulated a plan on how to tell the Princess about his feelings towards her. He arrived at the festival just in time to hear Zecora retell the tail of Nightmare Moon. Pip sat back and listened to the the zebra recite the story he had learned when he was just a young colt. As Zecora and the little fillies and colts headed towards the old statue of Nightmare Moon, Pip followed them then, at the statue, hid in the brush near the edge of the tree line.
As the little ones all deposited their fair share of candy in front of the statue, he waited with anxiety and excitement for the statue to come to life, as it did every year. They all waited..... and waited..... and waited.... and waited some more. Finally, when he thought Luna hadn't come this year, they statue came to 'life' and proceeded to scare the living daylights right out of everypony present, including Pipsqueak.
As they all ran away in fear, Princess Luna shrank back to her normal size and spit out the fake teeth she had been wearing in her mouth.
She sighed and said with a small smile, "Another year fulfilled."
"Indeed" Pip replied with a grin as he emerged from the underbrush. Luna jumped a little as she heard his voice and spun towards him. Shaking her head, she continued to smile as she jumped down from the pedestal and walked over to him.
"You scared me Pipsqueak!" she said, coming to stand in front of him.
He playfully bowed and said, "Oh, I beg your forgiveness, 'o great one!"
She smiled and said, "Rise, subject, all is well."
They both laughed at their corny shenanigans before growing quite. His thoughts turning to why he was here, Pip started to absently started pawing at the ground beneath him. Noticing this, Luna asked, "Are you all right Pip? You look rather distressed."
Remaining silent for a few more moments, he continued to paw at the ground. He eventually sighed heavily before looking up into the Princess's mesmerizing eyes.
"Princess, what do you think about relationships?" he asked rather suddenly.
Luna looked at him quizzically before answering, "What do you mean?"
"Like, if a stallion asked you out or on a date, would you say yes, or turn him down?"
Not sure where he was going with this, she chose her words with care. "Well... I guess it would depend on who was doing the asking and how I felt about them. Why? Is there a mare that you fancy?"
Pipsqueak blushed a deep, crimson color as he said, "Well.... Yes."
Luna smiled and said, unknowingly echoing Fluttershy on the last, "Oh really? Well, who is this mare? What's she like?"
Blushing deeper, Pip said, "She's beautiful, smart, funny... kind, sweet, compassionate...."
"Oooo, she sounds intriguing.. but you still haven't told me who it is yet!" Luna said with a smile.
Pipsqueak was now the deepest shade of red any pony could ever get. Without raising his voice above a whisper, he said, "Well.... because.... it's you....."
The Princess's ears flickered as she heard him whisper. She froze on the spot and looked at him with a blank stare. They both stood stark still, neither saying a word.
Finally, taking the silence as rejection, Pip said dejectedly, "Ok... I understand, your silence says it all....... I shouldn't have even thought of doing this in the first place..... I'll... just be going then...."
Pipsqueak turned to leave but was stopped as two dark blue hooves shot over to him and pulled him back around. Luna brought her lips onto his with such force, such passion, he almost let out an involuntary moan. They stayed together for a few moments, their lips locked together. When they broke apart, both blushed deeply and wore sheepish grins.
The Princess smiled and said, "I know...I've always known..."
Pip looked into her beautiful eyes again before saying softly, "I love you Luna."
Luna stayed silent as she leaned in closer, their lips barely touching as she finished in a whisper, "I love you too.... Pipsqueak."
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Hey everypony! Just had this idea so I thought I'd try it as a one shot. Tell me what yall think about and enjoy!!!
Also, if you dislike the story, please give the reason in the comments box so that I can fix it. Thanks!
The D'awww levels are so high now, it is to awesome for words
Not a dislike in sight. Btw, I've never heard of this "Rumble" character. Can anybody enlighten me?
Short but I loved it so much that it can be one hundard words for all I care. This is AMAZING! I have not read a great and vety well written Pip/Luna romance for a long time and very, very impressed by how you created it. Also, great job on adding great pairing such as SpikeBelle (my second favorite next to Spilight) Rumble/Apple Bloom, Scootaloo/Featherweight and the all powerful, always amazing FluttershyMac, seriously amazing job.
By the gods I can't wait to see what you have next or if you plan to take this story somewhere more like what Celestia would think of it or even if you plan on making another Pip/Luna story....I LOVED IT 100% You ever need any help, ideas or advice, I got your back, peace.
A few your/you're mistakes (esp. by Fluttershy's scene) but not too bad. Princesses need loving, too.
1601940
He is Thunderlane's younger brother.
1601686 Haha, why thank you my friend, I'm glad you enjoyed the D'awwws
As for continuation, I don't know if I'll continue this story or not. At this point, I could use some ideas if yall want me to add to this story or if I should write another Pip/Luna romance. Ideas please! 
1601940 I'm happy that you see no dislikes in sight
1601981 Thanks bro, your comment makes me feel special
1602122 Yes, Princess's do some need some love. Also, thanks for pointing out those errors, I'll fixs those right away.
1602200 Thanks for helping Blaze Burn Crash
As always, yall each deserve a mustache Spike for being the first to comment:
1604266 Never a problem, I got your back, I'll send you a PM with all the Pip/Luna ideas I have but your going to have to tell me which pairings you do and don't like if that's cool.
1604542 Thanks bro, can't wait for the PM.
Also, for the pairings, I'm good with all straight pairings and a select few les. pairings that I'll specify in the PM 
1604266
Always glad to help.
WHOEVER THE HELL PUT THAT DISLIKE SHOULD DISINTIGRATE IT'S VERY EXISTENCE.
She'd love him to pipsqueak?
beutiful.
1606157 isn't that a bit much?
2537499 Quite Sorry. That was my brother. If you want to diss him, go to his page, John Rigger.
2588006 nah its cool.
Aww. This is what I call a cute romance story. Nothing too mature or foul. And also what makes it okay is that Pipsqueak is all grown up.
Aww, so cute and sweet!
Also, a most excellent story.
A nice sweet story. Best of luck with your future stories.
A nice little story.
Awwwwwwwwwwwwwwwwwww
That's actually a pretty interesting ability she has which that's awesome that she can detect something like that
Well this was a pretty cute story and I have to treat this as an alternate universe but anyway pipsqueak as a young adult Was preparing for the Nightmare Night but only one specifically to talk with Princess Luna how much he means to her but he was afraid doesn't know what to say to her so he has some advice from Fluttershy and apparently it really helped him what she said to him so when princess Luna showed up just like before he talked to her and he admitted to her that he's in love with her and for reaction she knew that a while he just needs to say it and I got to say it is pretty cute keep up the good work