Rainbow's Rookie (Patreon)

Hey everyone, sorry it took me so long to post again, but hopefully, my longest story ever makes up for it! And I also apologize for this being kinda similar to my other Rainbow Dash story, but its what the patron requested. As a consolation for both of those things I apologized for, I've made this one open for everyone immediately! Enjoy!

Here it was: Day one. Tim was the newest Wonderbolt cadet, ready to take to the skies with the best of them. Soarin, Spitfire, and of course the drop dead gorgeous Rainbow Dash.  

Since Tim was the newest, he decided to arrive early to make a good impression. He strutted into the locker room, only to find it empty. He figured it’d be a good use of the extra time to change and get prepared to start practice as early as possible.  

He slipped out of his everyday clothes and quickly donned the Wonderbolt’s uniform he’d been issued. Once dressed, he stepped to the side to check himself out in the mirror.

He’d trained for years to get to that point, and now he finally got to wear the uniform. What he saw was impressive. ...Or so he thought at first. Upon further inspection, Tim discovered a serious shortcoming. A literal one, no less. His package lacked the size needed to fill out the uniform’s crotch, leaving it rather unimpressively baggy between the legs. Damn, that wouldn’t win him any points with the team’s ladies...

Thinking quickly, Tim reached into his gym bag and rifled around, pulling out a couple of socks. Returning to the mirror, he stuffed them down his underwear and arranged them in a way that made it look like he had some serious sausage and meatballs. He hoped people would be convinced.

Now feeling confident, he walked out to the airfield. It wasn’t long before the rest of the Wonderbolts arrived… Soarin, Lightning Dust… A few other rookies whose names he hadn’t gotten yet, and of course Rainbow Dash, his years-long sexual obsession, in the flesh! While he definitely noticed her from a distance, something he never expected in a million years happened: she noticed him.

“Hey, you the new kid?” She asked in her cute, tomboy voice.  

“Uh, yeah.” Tim struggled to say. God, he didn’t think she’d ever actually TALK to him…

“Cool, cool...” She said, eyeing him up and down. She gave a particularly long glance at his padded package. Tim wasn’t sure, but he thought he noticed a very subtle lip-bite as she assessed him. Though he was sure he was imagining it.  

“Good to meet ya.” She extended a hand. Her eyesight was, rather unsubtly, engaged with his uniform’s crotch. She was DEFINITELY scoping him out.  

Tim, who would normally be reduced to a puddle if a girl so much as looked at him, managed to keep his cool with his newfound confidence. He met her hand with his. “Likewise. I’ve been a big fan of yours for years!” He told her, honestly. Of course, he didn’t explain that being a ‘fan’ meant religiously jerking himself off to her pictures in magazines and the posters on his walls.

“Awesome! Always nice to meet a fan, and I always like to get acquainted with the new meat.” She smiled, turning to walk back to Soarin and the others. “Emphasis on meat...” Tim heard her mutter under her breath as she walked away. The stuffing sure seemed to be working. 

Neither of them made it very far, however, because a loud whistle sounded. Spitfire, their drill sergeant for the day, was now on deck. As if on cue, the more seasoned Wonderbolts formed a single file line, saluting the commanding officer. Tim, of course, followed suit.

They all stood at attention, Spitfire giving her drill sergeant instructions before takeoff. Tim did his best to listen to everything she said. This proved difficult, because of Rainbow standing right next to him. He peeked out of the corner of his eye to look at her, and discovered she was doing the same! Their eye lines didn’t meet, however, because hers was pointed in a more... southerly direction.  

Spitfire gave the word, and they all took off, following the orders they’d been given. In spite of the distraction he’d faced, Tim actually gave a great showing, hitting every mark and executing every move with a level of perfection that impressed even himself.

After a good, rigorous practice, they landed. Tim felt it couldn’t get any better; not only was he keeping pace with the rest of the Wonderbolts, but he had obviously caught the affections (or at least the libido) of none other than Rainbow Dash herself!  

After congratulating them for a great performance, Spitfire dismissed everyone. Everyone turned and filed into the locker room, which is when Tim noticed that both the male and female Wonderbolts were both heading into the same room.  

Noticing his confusion, Soarin patted him on the back. “This here’s the best part of being a Wonderbolt, rookie! Co-ed locker rooms!” He snickered as he walked past.

Tim’s mind raced as he put together what that meant. He’d get to see Spitfire, Lightning Dust, and all the girls in the nude, even Rainbow Dash! Just the thought of it was starting to get him stiff; he felt his cocktip brush up against rough fabric- That’s when he remembered.  

With creeping horror, he realized, his bulge would be revealed as a fraud as soon as he took off his uniform! He’d have no chance to hide the sock, and of course, the girls would all see his package was much less impressive than it appeared even if he could. He had to come up with a plan of action, and quick. He stepped into the room, cautiously, frantically wracking his brain for a workable way to avoid revealing the humiliating truth.  

… He didn’t have much time, however, before a hand wrapped around his arm. Rainbow dragged him aside, pulling him into one of the restroom stalls. Under any other circumstances he’d be delighted by such, but given his current predicament, it was about to be a total game over.

She backed him against one of the stall walls and gave him the most overpowering, sensual kiss he’d ever had in his life. When she finally broke it, she whispered in his ear,

“I guess I’m out twenty bits. Spitfire and I had a ‘Who’s gonna fuck the new guy first’ contest going on...” 

Rainbow took a step back and teasingly pulled down the zipper that bisected her uniform. Once it was down past her navel, she pulled the sleek spandex to either side, freeing her deceptively large breasts. Normally athletic girls had small breasts, but Rainbow somehow managed to be one of the bustiest pro-athletes in the world, at least as far as Tim was aware. They looked precisely how Tim had imagined them for all those years, sizeable yet perky, each dotted with a cute blue nipple. 

They were so incredible, Tim had almost forgotten about his impending humiliation as he stared shamelessly at Rainbow’s display. ALMOST forgot. The sight of Rainbow’s heaving bosom was enough to make his miniature member expand to its full size. Of course, this wasn’t apparent, because the scratchy sock fabric managed to completely bury his entire erection.

Tim decided it’d be for the best, or at least slightly less humiliating if he could explain the situation to Rainbow.

“Th-there’s something I need to-” He began to explain before she pressed a finger to his lips.  

“Shhhh. Just let this happen. I thought you were kinda cute when I first saw you. Then I saw this monster you were packing...” She grabs a firm handful of Tim’s sock-bulge and her sentence stops dead. 

“What the-!?” She exclaims. “Oh, don’t tell me…!” Without warning, she grabs hold of Tim’s zipper and yanks it all the way down, and Tim’s stuffing socks silently fall out onto the floor. Rainbow looks down at the socks, then up at his tiny throbbing erection, and then further up to look into his eyes with an indecipherable expression.  

“I don’t know whether to laugh at you, pity you, or kick you in the junk for wasting my time,” Rainbow said with a glare that quickly transitioned into a smirk as she looked back down at Tim’s exposed package.  

“Though I doubt I could kick you in the junk. Even at this distance, I might miss such a small target!” She blurted out, erupting into chortles. The full-body laughter was making Rainbow’s still-free bosom jiggle enticingly. Despite the humiliating context, Tim’s meager erection still twitched and throbbed at the athletic beauty. The tension of the situation basically froze Tim in place. He was obviously completely humiliated, but yet at the same time, he wasn’t about to try and leave a room with a semi-naked Rainbow Dash.

Rainbow managed to take a deep breath and seemingly regain her composure, but the minute she opened her eyes again and looked down at Tim’s exposed junk, she lost it again and began cackling into her palms.

“Pff, as pissed as I am about you tricking me, I honestly can’t blame you for stuffing. If THAT’S all the dick you’ve got, there’s no way you could fill out the uniform’s crotch,” she explained. “God, this is such a letdown. I spent all of today's practice daydreaming about getting stuffed with some thick pipe. Ugh, do you have any idea what I would’ve let you do to me if you had the python I thought you did? I dunno who I’m more disappointed for, me or you!” Tim was simultaneously the most mortified and most aroused he’d ever been in his life. 

She looked back down at it again, this time containing her laughter but still with a great big smirk.  “Actually, I’m pretty sure I feel worse for you. At least I can go out and find another guy with a nice fat cock. You’re stuck with this...” she waved her pinky in the air, “...little guy for the rest of your life.” She stared at it. “Jeez, can you even fuck a woman? It’d be like shooting hoops with a golf ball…” She mused.

She squatted down so that she was at face-level with the undersized, over-excited little boner. “Funny, I’ve been emasculating you since we got in here, and this thing still looks like it’s ready to blow! Are you some kind of submissive little perv that gets off on humiliation?” She looked up at Tim with teasing eyes. He was humiliated and horny beyond the capacity for speech. Rainbow’s gaze shifted back to his micro-member. 

“I bet that if I just…”

Without finishing the sentence, Rainbow stuck out her tongue and gave the cocktail weenie a quick-yet-firm lick. The sudden stimulation overwhelmed the very-cockteased Tim, who let out a very un-masculine grunt and his knees wobbled as a single thin rope of jizz fired forth, splattering on Rainbow’s left cheek.  

With a look that was equal parts shock, annoyance, and bemusement, she wiped her face with her sleeve. “That’s what I thought.” She muttered, standing up and zipping up her uniform in the same motion. She exited the stall with a “Seeya next practice, Tiny Tim!” 

The incident was so humiliating, Tim considered quitting, but soon talked himself out of it. As mortified as he was, Tim had worked too hard to become a Wonderbolt just to throw it all away. 

Tim had to practically drag himself to the next practice, knowing that anything that remained of his dignity would surely be crushed. Still, he walked into the locker room, early again to avoid getting changed in front of everyone else. But this time, he wasn’t alone. He opened the locker room door to find Spitfire herself seated on one of the benches. She looked up at him as he entered, and a grin appeared on her face.

“Hey, rookie! I got somethin’ for ya.” She throws a bundle of blue fabric in his direction. Tim catches it and unfurls it to discover that it’s a Wonderbolts uniform, just like he’d already been issued. He looked up at her, confused, but she decided to fill him in before he could even ask.

“Rainbow told us all about your… little problem.” She says, obviously barely able to suppress a giggle. “So I tailored this together myself. It’s got the upper half of a mens' uniform, but the lower half of a womens' uniform, so of course, you’ll find the crotch MUCH less roomy.” She laughed as she departed the room, leaving Tim to don his new humiliating apparel.  He turned it over to reveal the new designation on the back now read "Tiny Tim."