Author's Note

Feels good to be back, typing up chapters for people who legitimately enjoy them. I'm glad that I can be doing this again and while time been passing I've been thinking of awesome things that will be taking later on in the story. Anyways this is up here this time because I'm going to be giving a shout out to the ones that help me come up with an idea for the loser challenge. I say 'help' because I was gonna do you're ideas but then I put more thought into it and came up with something. I'll still be giving credit to those that led me to this conclusion. A thanks to Gamer91, Goldspoon, Daxen123 and Vadelent (Comment down below if I did not include you and you recommended a kinky outfit). Most of ya recommended a maid outfit (with the exception of Sailor Moon), so that got me thinking, 'A maid outfit is only good if you had said maid cleaning the high shelves.' So instead I thought of another kinky outfit and embarrassing routine, that I'm sure you'll enjoy.

Ch.10 - Loser Challenge~

Wilby's PoV

I was waiting in my dream for Luna but she hadn't come, I just assumed that she just had to get back to her duties or was learning everything that happened while she was gone. Though, that doesn't mean that I didn't experiment to see how it would work. I remember playing it back then and I wasn't really afraid of it at all, but now... it's... it's a whole new level of being afraid. That's all I'll be saying, for now.

Anyways, that's really all I've done for the entire dream sequence. Testing out to see how scary it would be and predicting how hilarious it would be to hear Luna screaming her ass off. And yes, it did take me all night to complete all four games... complete... the completionist is right, you would need a therapist after all that but I digress.

After I completed them, I soon "awoke" from my slumber. By that I mean I rolled out of bed and still got some extra z's on the floor. I despise waking up, it's always a hassle. Anywho, after I was awake, enough, I grabbed my clothing and made a mental note to have some made from Rarity. I say grabbed, because I was gonna take a soothing shower to wake me up even further.

After I walked out of my room I spotted Spike entering the kitchen and went to ask him where the shower was. "Oi Spike, where is the shower?" I asked sleepily.

He looked at me, "Dude, why aren't you wearing a shirt?"

I gave him my best 'are you serious look'. "Why aren't you?"

He squinted his eyes at me, "... Touché." He then got an evil look in his eyes. "Yeah the bathroom is the first door upstairs." He said smirking evilly.

I raised an eyebrow at him. "Well, whatever you say little buddy." I said making my way to the bathroom. The thought then hit me, 'Where's Twilight, shouldn't she be helping Spike with breakfest? Oh yeah, she doesn't... fuck it, I'm too tired to think.'

I made it to the door and reached for the doorknob, I opened it and saw something that made me even more glad that I was wearing baggy pants. I saw a fully naked Twilight in the shower, my mind completely turned off and my eyes glued on to her body taking in every detail. Her plumped ass, her luscious thighs, her moderate size breasts and best of all she was wet from the shower, making it very hard to pry my eyes away.

No PoV

Twilight on the other hand was in complete shock to see Wilby without a shirt staring at her naked form. Though, where Wilby was taking in evry detail of Twilight's body, she didn't need to think. She placed her left arm on her breast and pointed her body towards the side to haide away her marehood, though she didn't stop there. She sticked out her right arm and blasted Wilby out of the doorway and onto the ground of the first floor and closed the door with her magic, all the while screaming.

Wilby landed on the floor with a loud thud, not bothering to get up. Spike walked towards him and and a cheeky grin plastered on his face, "So, how has your morning been so far? Mine has been great!"

Wilby looked at him, "Shut up and get a wet towl for my head..."

Soon after, Wilby was sitting down in the kitchen, holding the wet towl onto the back of his head. Why a wet towl and not an ice pack? Should that even be explained? Anyways, Spike was cooking some breakfest for Wilby and Twilight. After awhile, a disgruntled Twilight sat down across from Twilight.

She looked at him, piercing his very soul. "So, want to inform me why you walked in on me when I was showering?"

Wilby had already though of an explanation, said explanation involved throwing someone under the bus... many buses, "I was wanting to take a long needed shower, so I asked Spike where it was" Spike froze from what he was doing. "and he told me that it was upstairs and nothing more, he didn't tell me you were in there."

Twilight glare was then transferred to Spike, "Why didn't you tell him I was taking a shower?"

Spike's eyes was darting around the room, sweat falling from his face. "Why did you throw me under the carriage?!" He yelled at Wilby.

Twilight figured she would deal with him later and she returned her gaze to Wilby, "And why did you continue to stare at me when you saw me?"

Wilby looked sheepish, "Well... I... I was taking the time to study the female anatomy of ponies." He chuckled nervously.

Twilight's gaze did not lighten up, "That's no excuse, you should have immediately closed the door. Not stand there like a pervert! Also if you were going to study the anatomy of ponies, I have books on that."

"Well how was I suppose to know that you were in there. I didn't hear the water running." Wilby said defensively.

"That's because there is a noise cancellation spell placed over the bathroom." She retorted.

Wilby looked at her blankly, "That's pretty stupid that there's a noise cancellation spell on a bathroom."

She blinked and her faced looked like she was in thought. "Okay, I'll take down the spell but that still doesn't mean you're off the hook from staring." She said, pointing a finger at me.

"Yeah yeah, I know... oh, and I want to visit Rarity for two things." Wilby said getting up. "Also, I'm going to take a shower, which was my original plan, by the way."

Spike glared at Wilby, "And why do you want to see Rarity?"

"I want to place an order for clothes and I want to get Rainbow's outfit ready." Wikby explained.

Twilight looked at Wilby, "Outfit? Just what are you planning for Rainbow?"

Wilby snikered, "Oh, you'll see." He said darkly, while heading to the shower.

Wilby's PoV

After I had showered and had breakfest, Twilight, Spike and I went made our way to Rarity's. On the way I spotted a rainbow hanging off a cloud and knew who it was.

"Oh Rainbow! You have a little something something to do." I called out to her.

I hear a groan from the cloud and she came down to where we were. "Fine, let's just get this over with. What do I have to do?"

I grinned at the thought of what she was gonna have to do, "Firs we're going to Rarity's to place an order of clothes for me and a set for you."

She looked confused, "You're gonna get me clothes?" She then put more thought into it and gasped, "I am not dressing up all prissy like!"

"Who said anything about looking prissy? You're gonna look much better than that." I said darkly.

She shuddered a little bit and we continue on our way to the boutique. Once there I went to open the door but a lavender pony stopped me. "You can't just walk into somepony's house without knocking." She scolded me.

I raised an eyebrow, "It's a boutique... anyone can walk in. Just like how anyone can waltz right into your library."

She looked sheepish, "Heh heh, I guess I'm not so use to that yet."

I rolled my eyes and opened up the door to hear the bell go off. I held the door for the others to go through and spotted Rarity coming in to greet us.

"Hello~ did you have a splendid morning so far." She said cheerfully.

"My mornings all ours wonderful when you're here Rarity." Spike gushingly said, making Rarity giiggle.

"Yeah, knowing that you have to do something embarrassing is always great." Rainbow said sarcastically.

Twilight blushed a little bit from what happened when she was in the shower. While I just had a goofy smile and rubbed the back of my head, chuckling nervously.

Rarity raised an eyebrow but disregarded it for the moment. "Well what brings all of you here, if you don't mind me asking?"

I stepped forward, "Well I would actually to put a placement for clothes for me, oh and would like my attire stiched up."

"Oh, of course darling and tell you what, I'll even do it for free! Just in exchange for some fashion ideas from your world."

I chuckled a little bit, "Yeah I was expecting that to be honest."

"Well I'm not the element of generosity for nothing-" She giggled. "-that title fits so well. Now if you'll follow me, I'll get your measurements."

I put my hand up, "Actually, I was hoping that can wait. The other reason we're here is for Rainbow." I said pointing my thumb at her.

Rarity was puzzled, Rainbow was disgruntled, Twilight was annoyed that she didn't know what I had in plan and Spike... Spike was still gushing over Rarity. "Why do you want me to make some clothing for Rainbow?"

No PoV

Wilby simply said, "I'll tell you in secret."

"Ok then, do the rest of mind staying here?" The rest shook they're heads. "Good, come with me Wilby."

Rarity and Wilby disappeared towards the back, which made Spike slightly jealous. All they could hear was murmurs for a little bit, after a while they were greeted with silence. Then they heard Rarity laughing hysterically, "OH YES, that would be absolutely hilarious to watch, it's free as long as I see that!" They heard Rarity yell almost too enthusiastically, making Rainbow all the more scared of what she had to do.

They appeared back into there view, "Then I'll make sure you'll get a front row seat." Wilby said.

"Right then, Rainbow I'm going to have to get your measurements real quick." Rarity said beckoning Rainbow over.

"I have the absolute worst feeling about this." Rainbow said.

Wilby's PoV

Rarity has gotten Rainbow's measurements and went to work on her clothes. Twilight decided it was time to ask me some more questions, mostly about science. I decided to go easy on her and just talk about elements and some of which that humans actually created, she was fascinated by how intelligent humans were. Rainbow on the other hand just been nervous and kept asking me want she had to wear.

After awhile, Rarity has joined us, holding a bag in her hand and giving it to Rainbow, telling her to go change in the bathroom. She hesitantly went to go do that and when she was out of our view, Rarity and I waited for her reaction. Twilight wasn't sure what she was waiting for until she heard it. We all heard the dreadful scream from Rainbow in the bathroom, Rarity is trying to hold in her laugh, Twilight and Spike were worried what she might be wearing, mostly Twilight, and I was waiting to see that good ol outfit once more.

The bathroom door opened and revealed Rainbow in a cheerleader outfit but not any ordinary cheerleader outfit. She was wearing Juliet Starling's cheerleader outfit, with some minor differences. The overall color scheme was a light blue and yellow and instead of "San Romeo Knights" it said "Wonderbolts" on it and it also didn't have the leggings.

"Why do I have to wear... this?!" She complained.

"Well since you want to be a wonderbolts so badly, I was merely thinking that you should show how much you supported them. And what better way to do so then cheer for them." I said, even more glad that I'm wearing baggy pants.

"This is gonna ruin my reputation! I'm never gonna be a Wonderbolt." She wailed.

"Pfft, as if, I'm pretty sure every stallion in the Wonderbolts is gonna want you to join and perhaps some mares that may root for the same team as well." I said, while putting smirking triumphantly.

She sighed, "Let's just get this over with..." She said, as we are made all way out of the boutique.

We made our way towards the center of town, attracting the very few stallions that were nearby, well Rainbow was. We made it to Town Hall where Pinkie was waiting.

"Hey everypony! Dashie, you're looking seeeeexy~." Pinkie said, making Rainbow groan.

"Hey Pinkie, I'm assuming you were waiting here for Skittle's cheer." I said walking over to the three chairs that she pulled out of no where. Rarity soon followed when I reminded her "front row seat."

"Yepperoni, also..." She pulls a megaphone out of her hair. "Everypony that wants to see Rainbow cheer for the Wonderbolts and lost the bet, come to Town Hall."

Almost immediately everypony that lived in Ponyville appeared right in front of Town Hall. Pinkie has also taken upon herself to collect my winnings. "Here you go Wikby, 1289 bits in full!" She said, while handing me a hefty bag.

"Sweet.~" I said, turning my attention to Rainbow. "Double sweet.~"

Pinkie told everyone to quiet down for Rainbow, which they did as they were told. It was so quiet and I was getting impatient. "Cheer already!" I hear a mare yell out.

"What should I even cheer?! I don't know anything about that!" She tried to come up with an excuse.

"Oh yes you do, you use to do it with Gilda." I said to her nonchalantly.

She growled at me, for ruining her excuse. "Fine..."

Before she can start I quickly added, "Do it 10 times, since it's so short."

She mumbled but complied non the less. She began doing her cheer, going through all the motions. Everypony began to cheer for her now, mostly saying "woo," though I noticed that most of the majority that was "wooing" were mares. 'Guess that kinda confirms that there are many more mares than stallions.' I thought before continuing to enjoy this embarrassing/kinky moment. 'I wonder what she would think when I tell her that she has to wear it for the rest of the day.'