In Pursuit of Happiness

Pinkie walked over to Scootaloo's side as she pulled her desk chair along. But when a curious thought entered her head, she stopped and placed her right hand on Scootaloo's head and began to gently scratch, very carefully giving her a soothing rub behind her ear. "I really mean it Scootaloo. I know how your life has been, growing up is hard. " Pinkie was staring blankly at the wall as she spoke. She felt an inkling of her former self as she empathized with Scootaloo "All that training wasted. Your mentor, friend, and potential lover not being into you. And even your friends....I mean, Sweetie Belle became a pop idol, leaving you behind. And despite the fact she stayed a virgin, it was only by her choice. She was still getting stallions to do what she wants like her sister would. And that fairy tale dream she had would have faded eventually and she'd have just picked some boy toy to marry. Somepony who would fall hopelessly in love with her. Somepony she can use on her own whims. Then there's Applebloom, not really sure too much on her other than the fact that her work schedule meant less time for you two to hang out. You tried adjusting your training schedule for her but it never seemed to click, and she never seemed to have the time to support your dream. And you Scootaloo? You're not a virgin by choice. You were saving yourself for that special somepony. You worked all your life for her....and it fell apart. I feel for you, I really do. So come on, what do you say? I could really use a personal assistant to help me out, and I'd really love it to be you."

Pinkie could feel Scootaloo tense herself, she felt it right as her ear twitched against her hand. She knew she was thinking about it. If only for a moment, she had probably considered it. But it only took a moment for Scootaloo to retract her thoughts and deny Pinkie Pie her wish. Pinkie knew it'd happen, if only because Scootaloo still had honor and integrity. Something she herself gave up long ago in her pursuit of happiness. To bring joy to all. And she didn't mind Scootaloo's choice either. No, because she knew she'd have her eventually. This would only make things more fun for her, that's all.

"Like I said..." Scootaloo said with stern will "I'll never give in, I'll never betray my friends. Once I get out of here, I'll tell Princess Celestia herself what you're doing here. And then? Boom! You're done"

"Ahh well" Pinkie shrugged as she pushed her desk chair behind Scootaloo's chair. A chair designed to have holes in particular spots for the sitter's torturer to bring their hands through them to tickle various spots of the ticklee. Pinkie noticed that Scootaloo's wings were visible through a large hole. She was tempted to just pluck a feather out and dance it along her own nipple. But she had to keep such thoughts out for now. She had to focus on Scootaloo herself before she indulged herself. But how to start? "let's start with something gentle, shall we? Can't go all in just yet!" Pinkie brought the fingers of her right hand to her mouth and spit a glob of spit on them. She then reached her arms into two holes that were on either side of Scootaloo and brought her hands to the front of her chest.

"Really?" Scootaloo looked helplessly at the hands as they approached her chest, she knew their intent. She realized that no amount of shouting would get Pinkie to stop. So she'd have to focus on resisting her until she could figure a way out. "You're going to tickle me? Seriously? Fine, waste your time. because we both know you don't have a lot of that left"

Pinkie snickered "That's adorable, you really think you can escape? C'mon Scootaloo, you're supposed to be the one laughing. Don't tell such funny jokes. Speaking of funny....cootchy cootchy coo!" Pinkie placed her slippery, saliva drenched fingers on Scootaloo's chest and rubbed along her nipple . She let it gently glide along in circles while wiggling her finger when she passed over the sensitive areola while giving her nipple a gentle flick. This wasn't truly meant to tickle. It was meant to arouse and distract. Pinkie's other hand however, was digging in between Scootaloo's ribs, sometimes poking the ribs themselves to illicit a reaction.

Scootaloo jutted forward, trying to escape Pinkie's fingers. But her bonds kept her in place. All she could do was grit her teeth and refuse her even a smile. She was letting out a few strained grunts as she felt her body was being hit by electric like jolts that tried to get her to smile. Luckily for her, her training gave her a strong body and thicker coat than somepony like Sweetie Belle might have. The thing that bugged her more than the tickling however, was Pinkie molesting her chest like that. Still, She could resist tickling like this, it wasn't too hard if she focused. That would do for now. "Heh, is that all you got Pinkie? You got pretty bad at this. And you're not the only one who knows and remembers things. I know how you get when you really screw up something. And you're really screwing this up. Why don't you just give up and leave? Or can you handle knowing how much of a failure you are at this?"

Pinkie...the old Pinkie...may have felt hurt from that. But this Pinkie? It only made her try harder. "Nice try Scoots! I mean really, nice try! If it was the old me? I'd probably be crying and sobbing and stuff. But sorry to say, I'm never going to stop until I get what I want. Now come on, how about you just relax and have yourself a giggle or two, huh?" Pinkie decided to rev things up a little. While her tickling hand still continued on Scootaloo's ribs. The hand fondling her non-existent breast moved back into her armpit. With Scootaloo's arm raised up, it was all too easy to press and wiggle her fingers at her tender flesh "Come on Scootaloo, just let it out. You'll feel a lot better if you do!"

Scootaloo tensed even further. Only bucking in her bonds with a few jerks before finding the strength to relax herself. Or rather relax herself the best she could. She was gritting her teeth and closing her eyes as the near electrical feelings of Pinkie's fingers surged through her body. She was doing the best she could not to smile, and while it was difficult, she was able to do just that. All she had to do was keep her mind clear. "Did somepony open a window or something? Because this is a breeze"

Pinkie could tell what Scootaloo was trying to do. She could see that she really felt she could be deterred through failure. Pinkie however, would not be denied. Her solitude had long since broken her of the fear of failing to bring happiness. And her goal had only filled her with unfaltering determination. Without saying another word. She had moved both her hands to her armpits and tried tickling there. But Scootaloo resisted. She tried tickling at her belly. But Scootaloo resisted. She even leaned in to tickle at her inner thighs. Which only had a slightly better effect on Scootaloo as she shook in surprise. In fact, although Pinkie couldn't see it. Scootaloo had cracked a smile from her soft inner legs being kneaded expertly. But she still held back from giggling. She didn't even snicker. "Just give up Pinkie! You'll never break me!"

"Wew!" Pinkie leaned back and put her hands to her hips "Gotta admit Scootaloo, you're pretty tough. I remember when you were a foal and you'd just laugh until you were beet red whenever I got my hands on you. But I admit, you really grew up. You're not my ticklish little filly anymore......." Pinkie was only being wordy however, she wasn't about to give up. She started to give it some thought on where Scootaloo could be ticklish. It could be her marehood. But if it was, she wouldn't be broken so easily since it'd instantly be pleasurable to her, not to mention that Pinkie was saving that for phase two of her plan.No, she had to find a place that would blast her into hysterics. And after another moment. Pinkie saw it, her target. It was her wings. Her still undeveloped wings. Pinkie would have never thought of tickling the wings of a pegasus pony before. But as she saw Scootaloo flap it around a few times. It hit her that the wings might be as sensitive as she used to be. An unorthodox place to be sure. Especially since the only other place Pinkie had yet to try was Scootaloo's feet. And she had special plans for those later.

"Give up Pinkie? Are you finally going to let me go?" Scootaloo asked, turning her head, trying to get a glimpse of Pinkie Pie.

"Nope...I actually want to try something." Pinkie reached her right hand onto Scootaloo's wings and plucked a feather, illiciting a sharp yelp from her.

"Ngh! Hey! What are you doing bac-NGH!" Scootaloo moved her head to the side when she felt Pinkie swishing a feather inside her right ear. It was so soft and her ear so sensitive that she had to pull away. "What's the big idea?!"

Pinkie giggled adorably, she believed she found her target. And with a feather in hand, she began to brush it along Scootaloo's neck. Again making her try to pull away. "It's soft, isn't it? Your little feather from your tiny wings. But it's still not enough to get a laugh out of you. Which got me thinking..." Pinkie said with a snicker as she continued to tease at Scootaloo's neck and ears, keeping her distracted. "What if your wings never grew up? What if my giggly little friend is still right there? Staring at me?"

"What in the hay are you talking ABWEFWEFDS" Scootaloo nearly lost herself. Suddenly, her body was being hit with a feeling she hadn't felt in a long while. Immediately her mouth twisted to a grin. She leaned forward the best she could to escape the tickling Pinkie was bringing to her. Doing her best to hold back the floodgates that kept in her giggles. "W-What a-are you..NGh...doing back there?!"

Pinkie was playing with her wings. Digging into her wingpits, and sliding her finger along the wing span. Gently pressing along the top part of her wings where the bone was "Trying to find the little pegasus I used to know. Come out come out little pegasus! I know you're there! Come out and pllaaaayyyy!" Pinkie said in a sing song way.

Scootaloo couldn't believe it. Her wings?! Her wings once again bringing her shame and doom as she had failed to realize how sensitive they were. She wished she had more movement. She wish she could kick her legs or pinch herself to get the intense feeling to calm down. She was smirking against her will as she bit her lip. Letting out sharp breaths that nearly sounded like titters. But she couldn't relent. No matter how hard Pinkie tickled. She couldn't relent. One mistake and she'd never be able to stop. She just had to keep her eyes closed and focus.

Pinkie however, had one more trick up her sleeve to get things started. She stood up as she continued the tickle assault on Scootaloo's back and wings. She leaned forward ever so softly, and bit down gently on Scootaloo's ear as she reached her tongue out and very sensually licked along the inside. "Scootalooooo...laaauuugghhhh, Scooootaloooo"

"nghhhee..nooNOOOAHAHAHAHA! NHAHAHAHAHAH!" Scootaloo's concentration broke when Pinkie lick-assaulted her sensitive ears. And with her concentration lost, she found herself unable to retain it as Pinkie cruelly continued the tickle torture on her wings. Scootaloo twisted in her bonds. Pulling left, Pulling right. But nothing she did could shake anything loose.

"There we go! There's my giggly little filly! Awww, you're just too cute when you giggle like that! You want more, don't you? Of course you do..here you go!" Pinkie, knowing Scootaloo would have great trouble calming down now that she had finally broken into giggle fits, started to assault parts of her body she had previously tickled before. Without her fortitude, even Scootaloo's chest became quite ticklish. Pinkie didn't mind at all, the more ticklish, the better. She expertly kept Scootaloo in perpetual laughter. In fact, Scootaloo was JUST laughing. She wasn't begging or anything."Soooo adorable!" Pinkie said as she slid her finger comfortably into her navel and span and poked along and into it.

"I'LHAHAHANEVERGIVEUPHAHAHA-ICAN-TAKETHIS-HAHAHAHA!" Scootaloo laughed out. She was strong indeed. Pinkie thought she was the only one who could tolerate tickling. It turned her on to be honest, she always wanted to tickle a mare who would just laugh without immediately screaming for it to stop. It made the laughter sound more pure.

"You can? That's really good. I mean, I could take this too. So it shouldn't be too much of a problem. In fact, why would it be? You sound like you're having a great time. You're really enjoying it, huh?" Pinkie taunted as she kept up the tickling back on Scootaloo's aerolas and nipples. Pinching and teasing them as she pressed her face against Scootaloo's wings and enjoyed the ticklish feeling on her face as she licked along her most ticklish parts.

Scootaloo, who was already drenched in her sweat from trying to escape, had yet another damp episode as her laughter became a song in Pinkie's ears. She continued to put on a strong front. But she could feel her mind at least wishing for it to stop. The feeling was too intense for her to contain her constant stream of mirth. and it'd only be a matter of time before she even considered giving in. "I'MNOTHAHAHAHAENJOYINGTHISHAHAHA!J-USTBECAUSEI'MLAUGHHAHAHINGDOESN'TMEANHEHEHEI'LL GIVE...IN....HAHAHAHAHA! I NEVER WILLHAHAHAHA"

Pinkie could feel it. She could feel her strong aura keeping her from breaking. But then, she herself would never stop either. All she needed was Scootaloo to beg for it to stop to move on to phase two. "Really? You're not enjoying this? If you weren't, then why are you laughing? I guess I shouldn't stop until you can prove to me you're not enjoying it. And I guess the only way to do that is to stop laughing!." Pinkie jeered at her as she rotated the tickling process from Scootaloo's pits, chest, neck, tummy, navel, and inner thighs as she used her tongue to lick all along the top of Scootaloo's wings.

Scootaloo couldn't resist nor anticipate the ticklish feelings surging through her, and she was losing some of her composure over Pinkie's taunting. She couldn't truly focus while she laughed and Pinkie rotated the tickling at a random rate, which meant she could never truly anticipate where Pinkie's fingers might be as her body got teased and molested. It was humiliating, given the huge grin on her face and Pinkie's assertion she herself was having a good time. One would almost think Pinkie was right considering the girlish giggling Scootaloo was doing . But all it was was laughter generated through tickling. Why did tickling have to cause laughter?! Scootaloo could only hold on to that thought for a moment before feeling Pinkie's tongue right in her rightmost wing pit, right on the underside of her feathers. She was breaking into hysterics now. While the feeling on her body was maddening. The laughter was causing her sides to burst. In her mind, she had realized she wasn't going to be able to stop laughing now. And any sounds of mirth was a win to Pinkie. She had to hold out. She just had to!

"It's so interesting Scootaloo, Really it is!" Pinkie said as she slid one of her hands out of the hole to poke and prod along her wings. Scootaloo was doing her best to try to escape it, but she was just stuck there, forced to laugh hysterically as every part of her wings were tortured. "I would have never ever guessed this was so ticklish. Wings? Really?" Pinkie giggled "I always thought they could be used to pluck a feather out for gigglish fun. Not to BE tickled itself. Ironic, isn't it? Isn't it funny? Doesn't it make you want to laugh!" Pinkie brought her other hand out, and put on another full on assault on her wings. All over her wings. "I knew, I just knew, that there was still some part of the old Scootaloo in here. Should have been obvious from the start it'd be your wings! Tickle tickle!"

Scootaloo was starting to lose her nerve. She tried one last move to restrain herself. She tightened all her muscles, and clenched her teeth hard. For a little bit. Her laughter came to a halt. The only problem was was Pinkie was relentless. She wouldn't stop assaulting her wings. "HnnnnnnnnnngggMMNNNNGGGHHH!" Scootaloo looked forward in determination, her mouth closed, she had to do it. She had to do it! Despite her body finally starting to ache, despite tears finally coming down her eyes from the tickling, despite it all. If she could keep herself from laughing again. She would be able to survive.

But Pinkie wouldn't stop. Instead, she just leaned her face in. And started nibbling at any substantial part of her wings as her fingers did the work on her wing pits. And that's all it took. Scootaloo spit out hard a glob of saliva before laughing harder than she ever had before. And still, Pinkie didn't stop. Her struggle was pointless, and she was afraid that she might lose her mind to the maddening jolts Pinkie's fingers were sending. And even though she had a strong body, even it wasn't immune to eventually feeling the gut busting power of laughter. She had to think of something. She needed a moment of clarity. And the only way to get that moment was...

"OKHAHAHAHA,OKHAHAHAHA! I GIVE UPHAHAHAHA! STAHAHAHAP ALREADYEHEHEHE!" Scootaloo called out, and to her surprise. Pinkie stopped after another moment. Pinkie didn't say a word as she stood up, dragging her desk chair with her as Scootaloo's laughter died down to titters, and then eventually heavy breathing. At this time, she had to think of a way to beat Pinkie before she revved up for round 2. "A trick maybe? Maybe she had a key in that lab coat, maybe I could reach with my hand by getting her to lean in on me and-" Scootaloo was thinking these thoughts in her mind, but found herself stopping on the last bit. It made her feel off. Pinkie was practically in the nude except for that small lab coat. She felt a small unexplainable urge in her nethers from that thought. But then something happened that really threw her off. She could suddenly move her right arm. It was released from it's binding. When she looked up, She saw Pinkie moving her desk chair to the front of her feet. She then pulled out her little device and pressed a button. Scootaloo's legs started to part just a little, the chair she was on splitting from the center where her legs rested. It gave Pinkie an unrestricted view of her marehood.

"WHAT ARE YOU DOING NOW?!" Scootaloo angrily barked. She had immediately given up on her thoughts of escape as she stared at Pinkie enjoying the view.

"Just feeling a little humbled that you really dig me" Pinkie said with a snicker

"Dig you? Really?! REALLY?! WHAT MAKES YOU EVEN THINK THAT?! WHAT'S UP WITH FREEING MY ARM ANYWAY?! YOU WANNA ARM WRESTLE OR SOMETHING?! C'MON PINKIE! YOU LIKE GAMES RIGHT?!" Scootaloo realized she was screaming every word. She also realized she may have had a way to bait Pinkie Pie. She gave her a sly grin, and spoke in a more smarmy tone. "C'mon. Let's arm wrestle. You win, I'm all yours. I win, you let me out of this Tartarus pit. Whaddya say?"

But surprisingly, Pinkie shrugged "Not interested, but you are Scootaloo. Oh..you really are. You've been winking at me since I sat down"

"Winking...what?" Scootaloo noticed where Pinkie's eyes were looking, she looked straight down and noticed her marehood was continually winking at Pinkie. Her clit becoming visible for seconds before disappearing back in for only a tiny moment. "W-what? How can...I?....NGH! STOP STARING!" Scootaloo blushed hard as she tried to close her legs. But it was to no avail. "IT'S NOT WHAT YOU THINK! IT-'S...IT'S....ERM..." She tried to quickly think of a reason. She dreaded the thought that she was actually...aroused by Pinkie Pie "...erm...f-rom all that touching...it's...normal"

"Yep, it is normal. It's normal to enjoy all the attention from somepony you find attractive." Pinkie said as she reached into her coat. Pulling out a strange jar and a paintbrush.

"A-ATTRACTIVE?! You?! Yeah right! Keep dreaming! Rainbow-..." She stopped, she looked away in shame when she realized who she was about to say. Rainbow Dash was indeed attractive. But she wasn't attracted to her.

"...Poor Scootaloo. Look, I'll tell you what. For this round of tickling, I'm going to let you have a little fun yourself. And then? Well, we'll see where the day takes us." Pinkie said with a giggle as she opened the the jar and dipped the paint brush into it.

Scootaloo looked back at her with a scowl as she tried to present herself as threatening despite being covered in sweat from laughing too much. She had grown a tad fatigued from the torture she had just been given. But she could still take Pinkie out if she had the chance. "Let ME have fun? How? Is that just another way of telling me I'm going to laugh some more? And let me guess, that stuff is going to make me more ticklish? Isn't it? tch, I never knew you for cheating Pinkie. Maybe I should be the one tickling you. I bet I'd be better at it then...you..are" Scootaloo's words slowed as she realized what she was saying. She couldn't let herself think such thoughts. It was just the arousal talking. That's what she felt it was. She only ever felt like this before when it came to Rainbow Dash. And of course, Pinkie cheated. Of course ANYPONY would feel aroused in this sort of situation. Right?

"Teeeempting. We could make that a thing, maybe. But, nope, not right now. It's Scootaloo time after all. And nope, this stuff doesn't do anything to you. It's just sugar glaze. Hehe, some habits just don't die." She was of course referencing her time baking with the Cakes. "As for you having fun? Yeeeeah, you're gonna be laughing a lot. That's for sure. And nope, begging won't get you out of it this time. No, this time? You're going to be tickled on your cute little feetsies. They should be sensitive and soft from that sweat. And the only way to make it stop?" Pinkie gave her an evil glare as she licked her lips "...Is to orgasm"

Orgasm? Scootaloo turned pale when she realized what she meant. She raised her hand and stared at it. Pinkie expected her to masturbate while being tickled.