Finding Gabriel

"I'm sorry, Gabe, but no." Dani didn't even need to think about it. Gabe's heart sank to his shoes.

"What? Why not?" he asked desperately. Gabe had been in love with Dani for about six years. Tonight, with a little bit of booze, he'd finally screwed up the nerve to ask her out.

Now Dani paused. "Gabe, you're a great guy, we've been friends for a long time-"

Gabe groaned. "Come on, let's just be friends? Really?"

"Quit interrupting, that wasn't where I was going with that. Have you ever known me not to give an honest answer?"

She had a point.

"Anyway. Gabe. You are a great guy. I know that. You, however, do not know that."

Gabriel raised his eyebrows. "Wait, what?"

She sighed. "Gabe. In the seven years we have known each other you have had two girlfriends I've met. Both times you tried your damnedest to be whatever the fuck they wanted you to be. Heather was a social butterfly so you took her out clubbing all the time and hated it. Tania wanted a hopeless romantic so you spent a shitton buying her flowers and wing and dining her and hated it. I between them, you dress like a high school metal head. Which, honestly, I would not object to, except you always look like you are uncomfortable in your own skin. You don't even LISTEN to the bands on your T-shirts any more. If I'm going to risk a friendship on a relationship, I want to know you won't tank it by trying to be what you think I want you to be instead of being yourself. So find yourself first."

"Wait, are you really saying I need to self-actualize before you'll date me?"

"No, just- just get on the right path, okay? Get to the point where you can at least wear something that makes you feel good, where you can like something about yourself. Give me an idea what direction you're going in."

Gabe frowned. "But if you don't like the direction, I'm out."

"Maybe, but I mean, if we're that incompatible, you don't want me." Dani smiled gently. "This isn't a rejection, okay?"

"It sure feels like one anyway," Gabe grumbled.

~~~~~~~~~~~~

The next week, Dani and a bunch of mutual friends made plans to see the newest superhero movie, and Gabe decided it was time to try something out.

He went to the local thrift shop, and decided to go with the "perverse prepster" look. After all, most of their male friends preferred it. When he pulled up to the movie theater, he was dressed in a pair of gray slacks, a white button down, argyle sweater vest, and colorful chucks. His wild brown curls were tied back.

They were already gathering when he arrived, and he turned quite a few heads as he approached. Eric whistled. "Look at you all fancy!"

Dani smiled appraisingly. She was wearing her typical legging jeans, tunic sweater, and sneakers, which was flattering as ever on her slim frame. Her long, brown hair was loose and she'd done minimal makeup to draw attention to her dark eyes.

Gabe shifted under her gaze. "What do you think?" he asked once no one else could hear.

"What do YOU think?"

"I think I look awesome." He grinned with false bravado, but her blue eyes pierced through him.

"You do. But I'm not so sure you believe that."

~~~~~~~~~~~~

By the end of the night, after some post-film drinks, Gabe was out of bravado.

The shirt was half open. The sweater, a $5 find, was ditched. His hair was freed. He felt like a little boy in a costume, and was done. Perverse Prepster was a failure, and he could see from her face that Dani knew it.

~~~~~~~~~~~~

The next two months involved a lot of trips to the thrift store. He tried seemingly endless combinations.

Soon their friends were all fully aware of his quest to find himself, or at least his personal style. For a night out, his best friend Eric helpfully loaned him some clothes to try out a more expensive look. He wore Eric's purple paisley satin shirt, black slacks, and pirate boots. This was a little better. He still felt stupid, but he liked the look, so he began to play from there.

Still Dani refused. There were times when he genuinely wondered if she'd always reject him, if she just didn't like him and his aimlessness was just an excuse.

"That's stupid," Eric commented, when he revealed this fear.

"You think she really does like me?"

"I mean, she obviously likes you. If she hated you, this quest would be weird and creepy, and Dani isn't the kind of person who would put up with that shit. Now, if she wants to sleep with you, hell if I know. But if her ploy works and you level up to confidence you'll have plenty of chicks who want to sleep with you. Look at Neil, dude looks like Jonah Hill and he still gets laid all the time."

Gabe sighed. "I'm getting kind of sick of this shit. I might just stick with the flamboyant pirate look."

"Hey! I will have you know that the flamboyant pirate look has worked VERY well for me!"

"Look, I just want to have one party where I don't have to care about my personal style."

"Whelp, you're in luck. Cass is having a genderbender and we're both invited."

Gabe raised his eyebrows. "A what now?"

"That's what she's calling it. It's basically just a drag party with a shitton of free booze."

"Why the hell is Cass hosting a drag party?"

"Because her roommate just got her first paid starring role as the dude in Hedwig and the Angry Inch, the one who's always played by a girl, and they're celebrating."

"Annnnd you're going?" Gabe looked skeptical, but Eric just laughed. "Look, man, I know you're struggling with your identity and shit, but I'm confident enough in my masculinity to handle a few hours of drag."

Gabe just looked at him. After a beat, he broke. "Okay, also we'll be like, the only straight guys there, and the girls will be drunk and handsy since they're going to be pretending to be male stereotypes."

"Dude, if they're drunk enough to not care you're in drag, they're gonna be too drunk to actually have sex with."

"They're theater chicks, amigo. Drag doesn't faze theater chicks."

"Okay, point there."

"Also, Dani will be there, and you can actually interact with her without all the fashionista baggage you've been going through."

Gabe paused. Hmm. On the one hand, he wasn't sure how he felt about Dani seeing him in drag. On the other, he really did miss hanging out with her without feeling like he was on trial. And Eric had played wingman for him in the past, too, often in more ridiculous scenarios than this one.

Finally he sighed. "Okay, fine, but we're even for that time you conned our way into the yacht club so I could pretend I was rich enough to sleep with Stacy van Hilbruk. And I'm NOT wearing a miniskirt."

Eric grinned. "Best of all, this misadventure is really unlikely to end up with a lifetime ban!"

"I reserve judgment on that until I see how we look as chicks."

~~~~~~~~~~

Gabe arrived at Eric's place two hours before the party, as directed. His friend greeted him at the door, beaming with excitement. "Hey! Come in, I was pretty lucky at Goodwill." He swung the door open, and Gabe let out a laugh.

Eric was wearing a schoolgirl skirt and a white blouse tied up Britney style; white knee socks and platform Mary Janes. He was wearing a bra stuffed with water balloons.

"Please tell me I am not going to also be dressed like the world's ugliest hooker."

"Please. You underestimate the world's hookers. And I respected your request to not have a miniskirt. You will be wearing pants." Eric gestured to the couch, where his finds were laid out- skinny jeans, an oversized sweater, Uggs, and a reusable Starbucks coffee cup.

Gabe burst out a laugh.

"I even got you some pumpkin spice body spray to complete the effect!" Eric said enthusiastically.

"Well, at least there are pants," he joked, stripping to his boxers to start the process.

The first thing he noticed was that the jeans were way more comfortable than he expected. Women's jeans were stretchy, and had plenty of space in the butt, which meant that unlike men's jeans they weren't constantly sliding over his rather round posterior. Unfortunately, he couldn't seem to get them on without bunching up his underwear.

Eric watched with amusement. "Not designed to be worn with boxers, huh?"

"Clearly not," Gabe replied drily.

"Good thing I got you these, then!" He held up a pair of black, silky, lacy panties.

"Are you freakin' kidding me right now?"

"Nope! I'm wearing them, boxers don't work with skirts." He hiked his skirt up his leg, revealing a flash of white silk underwear. Gabe made a face. "Really dude?"

"Look, it's that or go commando."

Hidden in a spare bedroom, Gabe tried commando first, and quickly dismissed it. The seam hit his cock and felt like he was getting rug burn.

With a deep sigh, he slipped on the panties.

They were surprisingly comfortable. The silk was smooth against his skin. He caught himself in Eric's mirror, and quickly shook his head. Why did he LIKE this? He'd always been drawn to women's clothing, but it had been in an academic sense- things he wanted to see on women in his life. This was different- and a little weird.

Now the pants went on smoothly. The sweater was also pretty comfortable, honestly, and Uggs were basically slippers. He stopped to look at himself in the mirror.

Once he was ready, he returned to Eric. "Okay, this isn't so bad."

"Great, time to go." Eric grabbed a blonde wig from a side table. "I'll put this on when we get there. I figured your hair is long enough you don't need a wig."

"Aren't we still really early?"

"Yeah, but Cass is doing our makeup for us, since I didn't want to spend $50 on makeup for a party."

~~~~~~~~~

Cass laughed when they walked in, but at least Gabe felt in on the joke. She made quick work of fixing Eric's wig and doing him up in over-the-top makeup- pink glossy lips, dark eyeliner, and sparkly eyeshadow.

Despite her best efforts, there was no mistaking Eric for a person who hadn't been drowning in testosterone since middle school. He was square jawed, broad shouldered, and had a pronounced Adam's apple, which he fingered as he admired Cass' work.

"Well, I think it's probably for the best that I'm not trans," he commented. "I pass about as well as a Russian athlete at a piss test."

Cass giggled and tucked some stray hairs into her baseball cap- she'd gone for a bit of a schlubby look, binding her already pretty small chest and wearing a wife-beater and black cargo pants. She'd even drawn on some fake stubble. "Okay, Gabe, your turn."

It took forever, and Cass sent Eric out to help her roommate- Jen, Gabe thought, got to remember her name is Jen- set up. First she painted his nails a soft pink. Then Cass decided his hair wasn't femme enough so put some ungodly amount of product in it before she even started on his face.

After what seemed like forever, she grinned triumphantly, and let him stand up and go to the mirror.

Gabe stared. The face looking back at him seemed both incredibly strange and incredibly familiar. Cass had done some of that weird contouring magic that took away a lot of the roundness to his face that he always felt made him look like a baby. She'd done his eyes in dark liner, and they didn't look tired like they usually did. She hadn't plucked his brows, but she'd used a pencil to give them a Brooke Shields look.

And- his hair! Whatever she'd put into it had turned the frizzy curls into sleek, defined ones. She'd parted it to the side, smoothed the "bangs," and pinned it behind his ear.

"Well, what do you think?" Cass asked finally.

"You have some skills," he declared, turning his head admiringly.

"Damn right I do! You look hot!"

He had to admit she was right. Unlike Eric, he actually felt like he looked... good. Though it probably helped that he wasn't dressed like a stripper caricature.

There were voices outside, and Cass glanced at her phone. "Crap, that took longer than I thought. People are here, let's go."

Cass led him out to the living room. Gabe felt surprisingly comfortable. Yeah, it was drag. But if he was gonna wear drag, he was more than a little pleased he looked pretty good in it.

Besides Jen and Eric, there were three other girls and two guys there. The girls all seemed to have either gone for the suit and tie look or the schlub look like Cass, though one had worn a trilby and drawn on some neckbeard. The guys immediately set off Gabe's gaydar- one, wearing a sparkly red mini dress, high heels, and an elaborate wig was clearly experienced at this, and the other had a rather nice Marilyn Monroe costume he couldn't fill out at all and flounced as he walked.

Everyone looked over as Cass entered, but Gabe was the one who got the whistles.

"Damn, girl!" Eric declared, coming over with the Starbucks mug. "Way to show me up! Here, I filled this with beer."

"Way to show all of us up, honey," the guy in the red dress purred. "Do you sing? Because I know a show that would LOVE you."

Gabe felt himself blushing, and briefly wondered if it was visible under the makeup. "I've been told I sound like a dying cat."

"Pity." Red dress grinned and held out his hand. "I'm Charlene."

Gabe took it. "Gabe." He paused, then asked, "Wait, sorry, uh- I legit have never had to think about this before, so sorry if I sound like a dick, but do you go by he, or she?"

Charlene laughed. "Don't worry, honey, you're fine. And I don't care- he, she, whatever."

Cass popped up beside Gabe. "My invite clarified that you dress opposite the gender you identify as, so anyone dressed like a girl is a he."

"Oh. I feel like I shouldn't be so confused by all this."

"Yeah, well, that's what you get for hanging with us feminazi SJWs," Cass replied with a grin. "Drink, all of you! Oh, Chelsea and Jana are here!"

Eric grinned as Cass scampered off. "Man, you actually make a pretty hot girl."

Gabe rolled his eyes. "Flattered, but I only like you as a friend."

"I say that purely objectively!" Eric protested as Charlene laughed.

"I gotta say I'm a little insulted by what girls seem to consider as male fashion," Marilyn Monroe commented, coming up to them. "I'm Trevor, by the way. And look at them, I'd never be caught DEAD dressed like this."

Eric shrugged. "Me neither, but I doubt any of them normally look like Marilyn Monroe or Britney Spears."

"Honestly, Gabs here is the only one who looks street ready," Charlene commented with a smile. "I may love this dress but it sure isn't typical house party attire."

"Yeah, I-"

"Ha, did someone not get the memo?" Gabe stopped mid-sentence. Dani. He turned.

She'd bound her normally good size breasts, and was wearing a gray suit with a bright red shirt and a complimentary red, black, and gray tie. Her long hair was done up into a large pompadour.

"Now that looks more like something I'd wear!" Gabe heard Trevor declare appreciatively. Dani was staring at him. "Wait, are you actually a g- oh my god, Gabe???"

Gabe grinned and took a little bow.

"Holy shit!"

"All credit goes to Cass, she did my hair and makeup."

"Jesus! I didn't even recognize you! Hell I thought you were an actual girl!"

"Ha, that's the point isn't it? You don't look too bad yourself, though not gonna lie, you're giving off more of a butch lesbian look than a guy look."

Dani was still staring at him. "Uhm, yeah, turns out I have a very girly facial shape... I'm sorry, you look amazing. And seriously your butt looks great in those jeans."

"Oh, yeah, I didn't even SEE that before!" Charlene declared behind him, giving him a good smack. Gabe jumped and glared at him, but he just grinned in response.

"I need something a little stronger than beer," he commented, holding up his cup. "Want anything, Dani?"

"Yeah, sure- whatever," she muttered, still looking shocked. He just laughed.

~~~~~~~~~~~~

Gabe was genuinely surprised at how much fun this was. Even as more guys arrived, he was widely accepted to be the best looking "girl" of the room. And Dani's attention was nice, even if it was just because he made such a great "woman."

After a few drinks, Charlene declared that as amusing as the costume was, it wasn't fair that he was the only guy in flats.

"What size are you?" he asked, and Gabe shrugged. "Ten- I doubt Jen or Cass have shoes in my size."

"I'm a ten!" one of the other guys called out. He was wearing a black miniskirt and a tube top, and he made quick work of popping off his black heeled pumps.

"Oh, come on..."

Cheers and chants of "do it!" greeted him. With a theatrical sigh, Gabe popped off the comfy Uggs and forced the pumps onto his feet. Carefully, he stood up.

"Do a catwalk!"

Gabe grinned confidently. They weren't comfortable, not by a long shot, but the whistles and the booze egged him on, so he strode forward-

And face planted.

Turned out that booze + spike heels + no experience was a bad idea. The girls- and experienced guys- immediately took to teaching him how to walk, and soon he was clumsily tiptoeing around, much to their amusement.

Eric ditched him around 11 for a cute redhead who managed to look hot despite the fake mustache glued to her lip. By 1 AM, most of the guests were gone, but Dani and Gabe sat chatting on the couch. Cass finally plopped down next to them and yawned obviously.

"Let's let Cass get some sleep," Dani replied with a laugh. She stood. "Come on, walk me home. There's a 24 hour store on the way and I really want a Choco Taco right now."

"Sure," Gabe replied, looking around for his shoes. "Wait- aw, man, did that guy seriously steal my Uggs?"

The owner of the black pumps had left, but the shoes remained, on the floor of the couch where he'd kicked them off. Gabe groaned as he realized he'd be walking home in heels.

"Jen and I have really small feet;" Cass commented apologetically. "I don't have any flip flops or anything you can take."

"Ugh, that sucks;" Dani added apologetically, though she was also fighting back a smile. Gabe shot her a look. "Are you enjoying this?"

"Not at all," she replied, giggling. "You can lean on me on the walk home."

It was a warm night, and they walked along in companionable silence for a little while, while he focused on not rolling an ankle on the brick sidewalk.

"I'm honestly impressed that you're comfortable just walking around like that," Dani commented, breaking the silence.

"I wouldn't call these shoes comfortable."

"I meant, like, emotionally."

Gabe paused. "I... hadn't actually thought about it. You think I'll get flack for it?"

"I don't know. Might be some drunks around."

"Eh, I can probably take a drunk or two. If I fight barefoot."

"Still, I gotta say, you seem more comfortable in that costume than you ever seem in day clothes."

"Eh, whatever, I look good and you know it." Gabe grinned, and Dani laughed. "Yeah you do. But I'm serious. You ever think about dressing like that normally?"

Gabe looked down at her and stopped. She stopped too. "I'm not trans," he said, a little defensively. "I like my dick probably more than the rest of me."

Dani smiled. "I know, Gabe, relax. I'm not suggesting you are. Liking women's clothes doesn't mean you're transgender."

"I'm not gay, either," Gabe protested, though he silently thought, well, except for Ryan Reynolds, but everyone's gay for Ryan Reynolds.

"Obviously, and that would have NOTHING to do with liking women's clothes anyway."

Gabe rolled his eyes and started walking again. "Look, there are certain things, like pants with a little extra butt room and whatever Cass did with the contouring, that I like about women's attire. But I'm not going to start going by Gabrielle or anything. I'm still me."

"I know, Gabe, that's what I LIKE about this look for you."

Gabe looked away, and they were quiet for a while as they walked. Soon Dani changed the subject to point out a cool constellation that was visible overhead, and they talked space and stargazing until they reached the little convenience store.