Defining Gabriel

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Self-confidence, from a little validation and a lot of love.
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Lacessor
Lacessor
16 Followers

This is a sequel to Finding Gabriel. I am hoping it stands on its own, too.

~~~~~~~~~~

Gabe stared at himself in the mirror. "I can't do this."

Dani came up beside him. She was wearing a cute little blue sundress, her brown hair flowing loose down her back. Pretty and femme and graceful, like a dancer. "Why not? You look amazing."

Gabe frowned. His eyes flicked back to his own reflection. His hair, silky curls brushing his shoulders. Dark liner made his eyes pop and a touch of contouring gave his normally round face a more defined look. He wore a black pleated skirt just above the knee, calf-high army boots laced with red ribbon, and a black and red tank top that laced up the back with a ribbon that matched his boots. Bracelets and bright red nails completed the look.

"Look at me. I'm obviously in drag," he complained. "I'm completely flat chested."

"Do you WANT to have breasts? I can stuff a bra for you if you want."

He sighed. "Not really. But I'm going to get my ass kicked if I go downtown looking like this."

"You are NOT." Dani rolled her eyes. "You look good. No one will care."

Gabe sighed again, staring at his reflection. He liked the look. He did. It felt... beautiful, striking. He always melted into the background noise in men's clothes. This outfit, he would be the center of attention. Which was both thrilling and terrifying.

"You promised," Dani pouted at him. "We're going to be late."

Another deep sigh. "Okay, okay. Fine. Let's go."

He'd made reservations. That was the deal, what she'd asked for and he'd promised-- a nice night out, dinner and then a show at their favorite bar, all dressed up.

The only other time he'd worn drag in public was the first time, two weeks ago. A drag party at a friend's house. But everyone had worn drag for it-- even afterwards on the walk home, Dani had been dressed like a guy.

They'd made love for the first time that night.

He'd been experimenting ever since. The internet was a great source for clothes-- he'd tried shopping with Dani but she refused to let him pretend they were shopping for her. There were no closets in Dani's mental house.

She was so... nonchalant! As they walked, she chattered on about work and friends and cool new scientific discoveries while his eyes darted around. Was that jogger looking at him? What about that dog walker?

He hugged himself, regretting that he had such defined arms and broad shoulders. He should have worn a sweater.

"Hey, it's okay," Dani said, suddenly soft. "You look great."

"I'm normally great at false confidence," Gabe replied with a rueful smile.

Dani smiled back. "False confidence is only good if your plan is to fake it til you make it. Come on, talk to me. Tell me about your week."

She was, if nothing else, a master of distraction.

The restaurant was crowded-- a nice little seafood place on the river. Dani prodded Gabe until he stepped forward.

"Two, please? I have a reservation. Gabriel."

The hostess nodded. "Right this way."

Not even a second glance.

They were seated overlooking the river, and as he set down his shoulder bag-- he wasn't ready to call it a purse-- he felt a tap on his shoulder, and he braced himself as he turned.

"I LOVE your boots!" the middle aged woman declared, smiling broadly. "Did you do that yourself, or did they come that way?"

"Uh, we re-laced them," he replied, a little startled. "Got the ribbon at Michael's."

"That's such a clever idea! I need to try that."

Gabe tried to stifle a smile as he sat down. Dani made no such attempt-- she was blatantly grinning at him.

"Yeah, yeah," he muttered, smiling at her.

Dinner was... uneventful. That was it. Uneventful. After the woman commenting on his boots, no one said a word about his attire or his name or his obviously masculine voice.

As they left the restaurant, Gabe leaned over and softly asked Dani, "Am I passing really well or something?"

Dani shrugged. "Passing as what? I mean, I don't think people are seeing you as a woman per se."

"Why the hell does no one care?"

"Welcome to the future, Gabriel. It's awesome. We have like a thousand kinds of beer."

Of course, the real test would be the bar. Because Gabe had a feeling that friends would be there-- friends who had not seen him dressed like this. Who had last seen him in metal band T-shirts and baggy cargo pants. He braced himself as they walked in.

Aw, shit. "Oh look, Eric's here!" Dani cried, pointing him out. Eric and Gabe had been best friends since college. Eric had even picked out his first drag outfit. He was not, however, aware that it would be a repeat performance.

Dani grabbed Gabe's hand and dragged him to the bar. "Eric! Hey!"

"Hi Dani-- Gabe!" Eric grinned, and his eyes flickered down. Gabe felt himself blushing a little.

"Hand-holding?" Eric raised an eyebrow.

Gabe looked down. Oh!

"Uhm, we might be..."

"We're on a date!" Dani interjected happily.

"Holy shit, you finally let this idiot take you on a date?" Eric grinned hugely. "By the way, you look good, man. Outfit works on you."

"Hey, I'll go get us some beers," Dani offered, quickly pulling away. Gabe nodded and turned back to Eric. He was still grinning.

"So that's what did it, huh?" Eric clapped him on the shoulder. "Don't get me wrong, it works. I just honestly did not expect that the androgynous look would be her thing."

"Me neither," Gabe admitted. He was starting to relax. "But she said she doesn't really care as long as I'm comfortable."

"Sure, but I'm sure she wouldn't want you wearing suits," he replied with a shrug. "Whatever. Dani's awesome, I'm glad it worked out."

~~~~~~~~~~

Gabe had a great time that night.

No one cared! At all! He didn't get any rude remarks or sideways glances. When they finally got back to Dani's apartment at 2 AM, he was giddy with excitement and probably also alcohol.

They snuck in past her roommate and straight to her room. He immediately grabbed her and started kissing her, his big hands working their way to the hem of her dress. Hers were just as busy, yanking his shirt up. He was already pretty hard, and she slipped her hand under his skirt to yank his panties down around his ankles.

He stepped out of them, and, overwhelmed with arousal, he grabbed her and lifted her up onto her desk. Thankfully she kept that pretty clear. He was quick to pull her panties off, and she grabbed a condom from the drawer, slipping it on him with impressive speed. Eagerly he thrust in, his skirt around his waist and her dress around hers as they kissed and fucked.

After a few minutes, she broke the kiss to try to straighten out their skirts, which kept rubbing. Gabe pulled out and quickly unzipped his, letting it fall to the floor. He pushed back in while he pulled the sundress over her head.

She was moaning now, saying his name, but he wasn't really listening-- she sounded eager, that was all that mattered. And he was close. He exploded inside her, then, before his knees gave out, he knelt between her legs to finish her off.

Soon they were panting, gasping, and Dani grabbed his hands, leading him to the bed. "Come cuddle with me," she begged, but Dani was bad at cuddling, and pretty soon she was riding him again.

Once they recovered from round two Gabe commented, "I normally can't go two rounds like that, but I always seem to with you."

"Well I guess I'm just that sexy," Dani replied with a grin.

"Damn straight."

"Seriously though I think you're just less anxious about the whole thing."

"Well, yeah, and you never let me roll over and sleep."

"Where's the fun in that?"

~~~~~~~~~~

In the morning... well okay it was like 11:30, so only morning on a technicality, Gabe texted Eric.

was it weird last night

was what weird? you and dani? i always knew she'd come around to it

not that man, the clothes like you can tell me if it was weird i won't take it personally

hey man whatever works for you nobody cares if you shop in the women's section i was a little surprised that that's what dani's into

you still think she wouldn't be OK with guy clothes?

yeah i mean girls don't have you change your look for them without it being what they want

Gabe sighed and set the phone down just as Dani poked her head in. "Hey, you're conscious! I made waffles. Well, I reheated waffles. In the toaster. They might be Eggos."

He grinned. "Haute cuisine. Thanks, let me just find some clothes before I scandalize your roommate."

Luckily he still had the pants and tank top he'd come over in the night before. As he ate fake waffles smothered in fake syrup he asked, "Do you want to go shopping today?"

Dani eyed him suspiciously. "Actual shopping, or me covering for you shopping?"

"Actual shopping, for real."

"Then yes!"

~~~~~~~~~~

The mall was pretty empty, since the weather was gorgeous and perfect for the beach. Figuring they'd have better fitting room selections, Gabe suggested they start at the department stores that anchored it. Dani promptly wandered off into the lingerie section and said he should text her if he wanted her opinion on something.

He did, about 10 minutes later, and she met him at the family/disability fitting room (he'd poked his head out about four times, worried about someone needing it).

"What do you think?" he asked, stepping out.

He'd picked dark women's leggings, a T shirt, men's blazer, and an oversized scarf-- a lot less femme than the night before, though far from butch.

Dani frowned a little. "No skirt with that?"

Gabe frowned back. Was Eric right? No middle ground? "I hadn't planned on it..."

"I like the idea, but in execution, you are gonna have some impressive moose knuckle issues."

Gabe's eyes went wide and he spun to the mirror. "Oh."

"Or, if you don't want a skirt, maybe a shirt-dress instead? Something a little longer. Or an extra long button-up but untucked."

"Oh, yeah, that works."

"Here, I'll grab one. What size are you?"

Next option was a slimly tailored woman's gray suit--with the curve to the pants and blazer, and a deep red silk shirt (admittedly from men's, but he didn't have the chest for the women's cuts). In lieu of a tie, he went with a strand of fake pearls.

"Ooo I like it. Where will you wear it though?"

"Uh..." In truth it was partially a test. He genuinely liked the outfit, but it was a bit more masculine, and he was curious what she would say.

"I'm just saying, it's pricey for something you can't wear much. Why don't you get something you can wear to work?"

Gabe froze. "I don't want to wear women's clothes at WORK!"

"Why not?"

"I'll get fired! I work in an office!"

"So get something office appropriate. You normally wear plain button-downs and slacks, right? Here, let me find something." She darted off while he changed into his next outfit. It was a bit of a departure-- a loose, flowy, peasant-style colorful skirt with a fitted black top that showed off his toned shoulders and slim torso. He immediately decided he was getting it, even if she didn't like it.

Dani came back and immediately whistled to see him. "That looks awesome."

"I know, this skirt is amazing." He gave a spin.

"Definitely on that one. What do you think of these?"

She held out a pair of tight, fitted khaki slacks. Gabe raised his eyebrows. "Those are just pants."

"Yeah, but they're tight, and they'll show off your ass really nicely. I got a couple colors." She held up folded pairs in gray and black. "You can wear it with different tops. Like here--" she held up a low v-neck sweater. "Wear this over the shirts you already own, and it will look much more femme. Or here--" she held up a red blazer with 3-quarter sleeves. "Wear this over a T-shirt. It's a man's cut so no one will complain, but the shorter sleeves make it look way more androgynous. I also found one with really tight sleeves that will look really femme." She held it up.

"Huh." Gabe paused, taking the 3-quarter jacket. "That could work. Let me try this on..."

$600. Gabe winced as he swiped his card. But he really, really wanted it, and he could afford it-- well, he could afford about half of it, with the rest to be paid off over the next year. He'd put back a bunch of the pieces, electing to keep the leggings ensemble with a short pleated skirt, the comfortable peasant skirt outfit, and enough mix and match separates to update his work wardrobe. The truth was, about 60% of the items for work were from the men's section. They were just slim line, skinny cut, fitted pieces. Trendy, and yes, very feminine, but perfectly work appropriate even in his conservative office.

"I'm not wearing makeup to the office, though," he cautioned as they walked out to the car. Dani shrugged. "I don't wear full makeup to work every day. Way too much work."

~~~~~~~~~~

This time, Gabe got ready on his own. He'd started about four hours before they were supposed to meet, and had, with difficulty and some YouTube tutorials, managed a decent contour and eye color that he wasn't happy with but could tolerate. He'd gone with the black pleated skirt, black leggings, red ballet flats, a gray tank and a red short sleeved blazer.

Walking alone made him nervous, but he steeled his resolve. Aaaaand... nothing. He passed a bunch of people-- men, women, kids. Not a word. It was almost anticlimactic.

Almost, because the climax was yet to come. When Dani opened her door, her eyes went wide. Gabe smiled sheepishly. "What do you think?"

"I think you need to come in here now," she declared, yanking his arm as she pulled him in. Gabe was instantly nervous, even checking himself as she dragged him past her big hallway mirror. What had he screwed up?

They stopped in her bedroom, and Dani sat him on the bed. She paused. "Do you have a reservation?"

"N-no... They have a good bar while we wait, but no reservations."

"Good." And with that, she pushed him back and jumped on him, kissing him deeply.

Quickly managing the shock, he kissed back, his hands sliding up her smooth legs to feel the curve of her ass. Hers, meanwhile, urgently tugged his leggings down. After a minute, he grabbed her and rolled over on top of her, then slid down her neck, kissing her collarbone. "You like the outfit?" he teased as his hand slid up, finding the very wet crotch of her panties and slipping past them.

"I-- ah-- I love the outfit," she replied, sighing at his touch. her foot, slipped out of her sandal, deftly grabbed his legging and gave a hard tug. He grinned. "Here, let me help." With his free hand, he tugged them and his panties down, and her toes ran down his leg.

Dani's pretty eyes went wide. "You shaved your legs!"

"Surprise?" Gabe responded, a little sheepishly.

She grinned, and answered him with another deep kiss.

It didn't take much for Gabe to finish hardening. Soon he was ready, he slipped on the condom she handed him, and he thrust quickly, rocking Dani back and forth on the bed. She grabbed his shoulders and he let her roll him over so she was on top, her breasts bouncing even through her dress as she slid up and down on his cock.

After a few minutes he sat up a bit, enabling him to reach around and grab her ass under the tangle of skirts. This was fast, furious, wild fucking-- the sort of thing born out of a desperate need to get release, and quickly, because you're also hungry and dinner just got delayed. They'd played around enough that he wasn't really surprised when she started to cum first-- it seemed really easy for her, which he was not about to complain about-- and it egged him on, pushing him to explode inside her with a ragged gasp shortly after she finished.

He flopped back on the bed, breathing heavily, and she rolled off him with a big smile on her face. After a moment of catching their breath, she started to giggle. He turned and started to laugh too. "What?"

"I smudged your makeup," Dani answered, touching his face with another giggle.

"Aww, man, I worked hard on it too!" His smile didn't break.

"I'll touch it up. I'm sorry."

Gabe grinned. "Never apologize, Dani."

"For having sex?"

"For any of this." And with that, he pulled her down into another kiss.

Lacessor
Lacessor
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AnonymousAnonymousover 2 years ago

Oh Hi There ,

I have so loved reading this story of yours , it’s definitely on the softer side of the spectrum and is so much easier to read and for me I felt I was making a connection almost I was Gabe ( or I wish I was ) . Thank you kindly for sharing your skills and imagination with us all and if you ever could I’d love to read on and see how they both are further down their path .

Love. And. Hugs

Kathryn .

AnonymousAnonymousover 4 years ago
Fun

Great fun story, no humiliation, pain or anal rape. Well written, light hearted & enjoyable. Regards

AnonymousAnonymousalmost 5 years ago
♥️♥️♥️

I love this so much! Loving relationship where everyone enjoys what they're doing and it's not humiliation-based at all

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