Curiouser and Curiouser

by anonpencil

Rating: mature
Tags: Timber Spruce, Twilight Sparkle (EqG), Slice of Life, Anthro, Romance, Fetish, Shining Armor, Equestria Girls
Length: 2227

When Twilight and Timber Spruce's couple's Halloween costume idea goes awry, Timber is left alone in a dress feeling very awkward. Things only get curiouser and curiouser when Shining Armor takes a special interest in his girly attire...

Timber Spruce thought that him going to a Halloween party in a dress wouldn't be weird. After all, Twilight said she'd go in a boy's costume, and it would be funny! But now she's wearing a different costume, and Timber is left dressed like a girl. How could this night get any weirder? Well, a certain older boy who's been admiring Timber's lacy costume is about to strike up a conversation and answer that very question.

WARNING: Contains Crossdressing, Petticoats, Bisexual, Skeezy Older Brother, Femboy Fetish, Femmecon, Very suggestive conversations and actions but no sex

Done as a commission for shortskirtsandexplosions, and thus contains short skirts, but no "explosions."

Published 2018-11-15 19:10:01 UTC
Last updated 2018-11-15 19:10:01 UTC

We're All Mad Here...

~*~

Timber Spruce sat in the corner of the room, glumly gazing out over the sea of happy partygoers. He cold easily spot Twilight flitting around the room like an over-excited butterfly, checking to make sure all her preparations were going as planned. Her Halloween costume was positively lovely. It was a short green dress that came to points at the ends, and sparkling transparent wings adorned her back. In her hand was tightly clutched a wand that lit up when she moved, which was just about every five seconds. It was definitely a well fitting and super cute outfit.

The problem was, it wasn’t what she’d said she was going to wear.

Timber remembered how excited he’d been when Twilight had suggested they take a new twist on a couple’s costume this year. He’d been hesitant at first, especially considering the request, but the more they’d discussed it, the more fun it sounded. The Mad Hatter and Alice from Alice in Wonderland weren’t a couple by any means, but he was fond of Lewis Carroll, so it ended up being an easy sell. They’d planned their costumes for weeks, worked together, and even when it was frustrating, he’d gotten through it. He’d showed up at her door this evening and...

He shut his eyes as he remembered the moment of pure embarrassment.

The front door had opened, and there Twilight had been looking absolutely adorable, but dressed as Tinker Bell.

“Twi, what…?” He’d started to ask, in confusion and more than a little anger.

Then he’d glanced past her, and he’d seen Sunset Shimmer wearing a very dashing Peter Pan costume. And everything had just clicked. When he’d looked back down at her, she was glancing sheepishly away.

“Sunset's having a rough time,” she’d mumbled, obviously ashamed. “All the girls decided to go as various characters from Peter Pan because it’s her favorite movie, and, well, this was the only costume I could throw together last minute. I got so preoccupied in putting it together, I forgot to call you and let you know there was a change. I’m… sorry.”

Sorry didn’t cut it, and he’d hardly spoken to Twilight since. Timber knew she was all about being a supportive friend and was generally understanding. But this was a special circumstance. Because tonight he was now stuck at this party, surrounded by all of Twilight’s friends, in a costume that only made sense if he was standing alongside someone else.

Timber now looked down at the dress he was wearing. It was a pale, cornflower blue, and came to an end in lace. The sleeves were short, and poofed out like little bread rolls right where his arms met his shoulders. His collar was white, and neatly turned down, and matched the white stockings he was wearing underneath. He’d struggled with the pinafore at first, but now it was fastened snugly around his waist and chest, tied in a large neat bow right above his butt. His shoes were black patent leather, and were so well-shined that he was sure people could see right up his dress if they looked too long. Luckily, he’d worn a petticoat that was thick with ruffles and lace, so no one would see that he’d gone the full nine yards and worn white silk panties as well. He was a little ashamed to admit that they felt surprisingly comfortable.

He thought the dress itself was actually pretty on him, and he’d admired his reflection longer than he probably should have when he’d first gotten dressed. The wig was itchy, but he’d always wondered what he’d look like with long blond hair and bangs, and now he did. The black bow on top of his head seemed a little much to him, but such was the costume, and he’d done his best to be faithful to it. Twilight, on the other hand, had left him alone, in a dress, unsure what do to. It was hardly, in a word, faithful.

Timber sighed heavily and righted his options. He could stay and try not to notice the other boys and girls staring at him, and maybe get some punch and pretend to be normal. But that didn’t sound like much fun, and he wasn’t certain he could stop himself from blushing. Or, on the other hand, he could just go home, get out of this dress, and try to pretend that tonight had never happened. That really sounded like the better plan.

He got up from his chair in the corner, and reflexively smoothed out the dress in front of and behind him, so it didn’t ride up on the petticoat. It was a shame, he thought, that he wouldn’t get more use out of the dress, but just being Alice alone at this party was weird. He stuck out like a sore thumb, and there was no telling who was making fun of him for it.

Timber turned to go, and found himself nearly nose to nose with someone dressed in a very princely costume. It took him a moment to recognize the pale skin and tousled dark blue hair as that of Twilight’s older brother, Shining Armor. He’d hardly talked to the older boy before, and he found the guy sort of intimidating if he was being honest. And to have him right there, staring, while Timber was wearing a dress? Timber turned his face away, hoping the long golden locks of the wig would cover his quickly spreading blush.

“O-oh, hey,” he says quickly. “Sorry, didn’t mean to bump into you or anything.”

He glanced back up at the other boy, and found him smiling warmly.

“Hey, don’t worry about it,” Shining Armor said lightly. “I was sort of in the way, no big deal.”

“Cool,” Timber said.

He still had his eyes on the door, ready for a hasty exit, but Shining Armor didn’t move. It was… rather strange.

“Uh,” Timber stuttered out. “I was… just thinking about leaving, so…”

“Aw, man, don’t do that,” Shining said with a frown. “I was just coming over to say hi to you. Timber, wasn’t it?”

“Timber Spruce,” yeah,” Timber said. Why would Shining Armor be coming over to talk to him?

“I know we’ve met before but, heh, I guess it’s nice to re-meet you then!”

Shining Armor reached out, but rather than going for a handshake, he set a large palm onto Timber’s shoulder. Even through the fabric of the dress, Timber could still feel that the other boy’s hand was very warm. It made his stomach feel twisted inside for some reason.

“L-likewise,” he stammered out, looking up into Shining’s face. It was still uncomfortably close to his own.

“So,” Shining went on. “Alice? From Alice in wonderland?”

Timber felt more than saw Shining’s eyes move up and down his body to admire the dress.

“Yeah,” he said quickly, looking away again. “Twilight was supposed to go as the Mad Hatter but… well… friendship stuff came up.”

“Hey, I feel ya,” Shining said with a knowing nod. “Cadance wasn’t feeling well, but she originally was supposed to come as Cinderella and I’d be the prince. But, because it’s my little sister’s party, I decided to come solo. It’s nice to see someone else here who… isn’t paired up with anyone.”

Timber could sense a funny sort of something in his voice. A silkiness that caressed his skin more intimately than even the silkiness of his panties.

“I guess,” he said. “Just kinda sucks that I ended up here in a dress.”

“Now, I wouldn’t say that!” Shining Armor said. “It’s a nice dress at least. And actually, it fits you really beautifully?”

In spite of himself, Timber couldn’t help glance down at the dress, then up back at the older, taller boy with a half smile.

“Really?”

“Yeah really,” Shining said with a grin. “Most guys can’t pull off a dress and actually have it look… well, cute.”

Timber flushed deeply. Had Shining Armor just called him cute? What was going on here? Why did he suddenly feel so hot in this dress now? Why was he blushing so deeply? Why did it feel like Shining’s hand was burning a hole through his arm where he was touching the dress? Timber stammered for a moment, unsure how to respond to this.

“I… er… thanks,” he said at last.

“Don’t mention it,” Shining said with a wink. “I mean, you looked fine before, I’d definitely noticed you. But in this dress?”

He made a soft mmmm noise in the back of his throat, like he was hungry. Again, Timber felt his stomach do a backflip.

“Th-thanks,” he said again, unsure what else to say.

All at once, shining frowned.

“Hey, are you… uncomfortable in that?”

Timber shrugged, but Shining still didn’t move his hand.

“Well, It’s a little tight in the middle,” Timber admitted. “But otherwise not so much. I guess it’s a little hot too. And the lace makes my legs itch. So… sorta?”

Shining Armor gave a low chuckle.

“Well, my old room is towards the back,” he said. “If you want, I can go help you… get out of that dress. I mean, I have boy clothes here still, if you’d rather.”

Something about this offer was odd, but it did sound kind of good. Shining Armor was a pretty cool guy, very popular, had so many friends. Timber would be lying if he said he didn’t look up to the guy. And the attention from him felt pretty good. He was trying to be nice, trying to help, and something about that felt really nice. And it also made his face feel kind of hot. Was there a reason to say no?

“Sure,” Timber said after a moment. “Not sure I’ll fit your stuff though. You’re bigger than me, after all.”

“Oh, I’m counting on it,” Shining said, as he turned the smaller boy towards a back hallway. “By the way, you’re eighteen, right?”

“What?”

“Nothing, nothing,” Shining said in a sing-song kind of way.

The two boys made their way to a back room that had the name “Shining” carved into a plaque in the door, surrounded by little stars and shields. Timber waited patiently while Shining turned on a light, and then stepped inside. No sooner were the two there before Shining shut the door behind him. When he turned, he was smiling a cool, calculating smile.

“So… want me to… help you out of that dress?”

His tone was unmistakable this time. Timber felt his throat tighten, and noted that his panties felt a little tighter too. Was… he enjoying this? Did he want this? He was embarrassed that instantly the first thought that came to his mind was yes. Shining Armor was princely looking, handsome even out of costume, and to know they he’d been attracted to Timber before? It was a pleasant thought. One he now realized was welcome, and enticing. Still sheepish, he looked away.

“A-and what if I don’t?” he mumbled.

“Then we can leave the dress on, it is quite becoming on you anyway.” Shining said. “Or did you mean that you wouldn’t be interested in…”

“…I might be.”

“Might?”

“What about, you know… Cadence?”

Shining Armor waved a hand dismissively.

“We have a little arrangement,” he said with a sigh. “And there are special exceptions for a few guys I have crushes on. Mostly very cute ones.”

“Y-you think I’m cute?”

Timber again felt the other boy’s eyes move over his body searchingly. In that dress, he suddenly felt so naked, but also so pretty, so attractive, so wanted. He pressed his legs together, hoping the ruffles of the skirt would hide how excited he was. Shining walked towards him, quickly closing the distance and then moving both of them backwards towards the bed in the corner of the room.

“Absolutely,” he practically purred.

He reached out, and Timber felt Shining’s hand move up his stockinged thigh, moving further and further under the folds and ruffles of the petticoat. He swallowed hard as the older boy drew him closer until their bodies were pressed against each other. Now, Timber could feel that Shining was excited as well.

“So, Alice,” Shining Armor said as he smiled down into Timber’s deeply blushing face, “Are you willing to see how deep the rabbit hole goes?”

Timber shut his eyes and took a deep breath as he felt Shining’s hand reach his silk panties, and felt his fingers playing over them. It was now or never. Did he want this? Was this okay? At last, he swallowed hard, and opened his eyes. He smiled.

“As long as you’ll be my prince charming.”

Shining let out a low chuckle as he reached over to the lamp beside the bed, and deftly turned out the light.

-END-

Author's Note

For the record, I love Alice in Wonderland, and I am sure Lewis Carroll would be very ashamed of me. Fortunately, I lack shame in this case, so hooray!

Written as a commission for shortskirtsandexplosions who is super awesome and nice and go follow him and give him e-hugs and stuff. If you'd like to commission me too, go check my blog posts to see if I'm still open (my commissions will close on Thanksgiving!)

-pencil