Ch 12. A Celebration Date With Edna

Despite Leo's initial belief that he would get a break after finishing the work at the power plant, the last two days had been unexpectedly busy with the aftermath of the community meeting. Between teaching, grading paperwork, coming up with a plan for the strike, and securing sponsorships with Edna, he barely had time to breathe. But today, Leo finally got the well-deserved rest he had been craving.

He spent the day lounging at home, taking full advantage of the many amenities his new place provided—especially the hot tub. The warm water had worked wonders on his muscles, easing the tension that had built up over the past few days. He felt like a new man.

Right now, he was climbing out of said hot tub, drying off. He felt relaxed, his body warm and at ease as he reflected on the day. He had just gotten off the phone with Marge, who had finally called back and scheduled their next photoshoot for the following day. He spent the time fantasizing about what tomorrow would be like with her until his thoughts eventually drifted to something—or rather, someone—else.

Edna. The victory of them ending the strike in the way they wanted gave him the perfect opportunity to talk more with her. He had called her up and casually suggested they celebrate with a night out. Not to his surprise—Edna excitedly accepted.

Standing in front of the mirror, adjusting the collar of his jacket, Leo smiled to himself. Edna wasn't like the others. Where the married Marge and Maude required a softer touch and more time, Edna welcomed boldness. She reminded him of Cookie, but not as desperate and a little more refined.

An hour later, Leo stood outside her door, a confident smile on his face as he adjusted his jacket one last time. The air was crisp, a light breeze rustling the trees as he knocked. He glanced around the neighborhood while waiting, noting how quiet it was. A moment later, the door swung open, and there she was.

Edna stood before him in a tight blue dress. There were slits along her hips, stomach, and back revealing plenty of her smooth skin. The dress made sure to highlight her slim waist and her full, round ass that Leo could catch glimpses of from where he stood. Her thigh-high black boots added to the look, making her look both seductive and commanding.

She knew exactly what she was doing, and Leo liked that.

"Well, well," Leo said, letting his eyes sweep over her. "Looks like we're really celebrating tonight."

Edna smirked, leaning on the doorframe.

"You bet. A win like that deserves a night out. I don't dress like this for just anyone, you know."

"Good to know I'm not just anyone," Leo replied smoothly, his eyes locking on hers.

She returned his stare but her eyes quickly moved as she noticed the sleek black luxury car that was parked behind him. She raised an eyebrow, impressed.

"Nice car. I'm starting to think I underestimated you, and I didn't think that was possible."

She stepped closer, her fingers lightly brushing over his chest. The past day had shown her many of the things she found attractive in Leo, and with the worries of the strike behind her, Edna wasn't one to shy away from what she wanted.

"Between this," she gestured toward the car, "and the way you mentioned your business connections, I'm guessing you're not just a simple guy."

Leo leaned in slightly, a smile tugging at the corners of his mouth.

"I guess you could say that. I've got my hands in a few different things. But tonight, I'm sure I'll find better places to put them."

Her smirk widened.

"Oh, I'll bet."

They exchanged more playful banter as Leo led her down to the car. He opened the passenger door for her, his hand resting lightly on her exposed waist, the touch lingering longer than what was necessary as he helped her get in. The contact made a small shiver run up Edna's spine, making her excited for the night.

Once she slid into the leather seat, Leo gave her a mischievous grin.

"I hope you're ready to indulge yourself tonight. I've got a few surprises planned," he said, his voice carrying a playful tone.

Edna raised an eyebrow, her lips curling into a sly grin. "I can't wait to find out what they are."

…

…

…

The drive to the restaurant was comfortable. Edna glanced out the window, watching the lights of Springfield pass by, though her mind was elsewhere. Leo had surprised her. The more time she spent with him, the more layers she uncovered. She wasn't entirely sure what to make of him yet, and that intrigued her even more.

They arrived at the restaurant.

The one he had chosen was upscale, its atmosphere warm and inviting. As they walked through the entrance, Edna noted the soft lighting, the quiet hum of conversation, and the scent of delicious food that wafted through the air. It wasn't a place that flaunted its status, but it was clear from the vibe and decor that this was a spot for people who appreciated the finer things. Leo had taste.

As they sat down at a quiet corner table, Edna gave the place a once-over, clearly impressed.

"You sure know how to pick a place," she said, her tone teasing. "Do you bring all your women here?"

Leo grinned. "Only the ones worth impressing."

Edna laughed. "Well, I guess I should feel lucky then."

Before long, their server arrived with a bottle of wine. As the waiter poured their drinks, and Edna noticed the type, her eyes flicked toward Leo.

"You have a habit of picking the good stuff, don't you?"

"I like to think so," Leo replied, lifting his glass. "Here, a toast to ending that strike."

Edna raised her glass, clinking it against his.

"Here's to that," she said with a grin. "And to seeing Skinner's face when he realized he had no choice but to give in to us."

Leo chuckled. "The guy never stood a chance."

"I almost felt bad for him," Edna quipped, swirling the wine in her glass before taking a sip. "Almost."

The conversation flowed easily as they enjoyed their meal. Edna's sharp wit and biting humor kept Leo on his toes, but he liked it that way. 

"So," Leo said, setting his glass down after their plates were cleared. "Tell me something about yourself. Something most people don't know."

Edna raised an eyebrow.

"What, you mean like deep, dark secrets?"

Leo smiled. "If you've got any, sure."

"Hmm," Edna leaned back in her chair in thought. "Well, I wasn't always this jaded, cynical woman you see before you. Believe it or not, I had dreams once. Big ones. Teaching was supposed to be my way of making a difference, but..."

She trailed off, her eyes flicking away for a moment as if recalling a distant memory. Leo tilted his head, waiting for her to continue.

"Life happened," she said with a sigh. "I mentioned it to you before, but life has a way of beating the optimism out of you. Especially this town, the system, the people—it all just grinds you down."

Leo's mind began to turn as he recognized her vulnerability. He saw the opportunity to draw her in closer.

"Was there anything in specific? Something that hit harder than anything else?" he asked.

A faint, almost wistful smile tugged at Edna's lips.

"I guess. I was married once. Thought I had it all figured out. Then he ran off with our marriage counselor." She let out a sharp laugh, bitter but not quite broken. "After that, I decided to focus on my career. At least you can't be betrayed by a chalkboard."

Leo was surprised that she was married before, not knowing what to think of it. He feigned a sympathetic expression.

"Sounds rough," he simply said, knowing she would rather vent than hear his thoughts at that moment.

"It was," Edna admitted, her fingers playing with the stem of her wine glass. "But you get used to it. The job, the students, the loneliness... it all blends together after a while."

Hearing her words, the opportunity alarms rang in his head. Leo reached across the table, his hand lightly brushing hers.

"You don't have to do it alone," he said softly, his voice filled with empathy. He leaned in a little, his gaze holding hers.

Edna's gaze lingered on his hand, then lifted to meet his eyes. She enjoyed the feeling he gave her, the touch of his hand. It was like how she felt when he took her hand before going into the business, but this time it was stronger. She took a second to soak in it.

"I guess not," she said, agreeing with him, her voice softer.

Leo gave her a gentle smile, one that he knew would convey a mix of sincerity and intrigue.

"I'm right here with you. I could listen to you talk all night," he murmured, leaning back slightly but still holding her gaze. "It's rare to meet someone who's so passionate, who sees things the way you do. Most people just go through the motions… but you've still got that fire. I know it."

Edna chuckled, shaking her head. "You think you've got me all figured out?"

"Not yet," Leo replied smoothly, his voice lowering, "But I love hearing about it. There's a lot more to you than most people see, and I get the feeling I've only scratched the surface but I want to go further."

She laughed again, but this time it was softer, her shoulders relaxing as she leaned back in her chair, allowing herself to be a little more open with him.

The evening wore on, their conversation diving into deeper topics. Leo shared stories about his business ventures—some legitimate, others more questionable—while Edna opened up about her frustrations with the education system and her life in Springfield.

Much to Leo's surprise, Edna even mentioned her past on-again, off-again relationship with Principal Skinner.

"It was more about convenience than anything else," she confessed with a shrug. "Skinner... well, he's not a bad guy, but he's weak. Too scared to stand up for himself."

Leo leaned back in his chair.

"Come on, I didn't think you were the type of woman to settle for someone like that. You seem like the type who needs someone strong. Someone who knows what they want and isn't afraid to go after it."

Edna's lips curled into a mischievous smile.

"I like a man who can take charge, sure. But it's not just about strength. I want someone who can keep up with me. Most men, well, they get tired too quickly."

Leo chuckled, raising his glass in a mock toast.

"Then I guess I'm your kind of guy."

Edna smiled knowingly, swirling her wine before taking a slow sip. "Oh, I already have a feeling you are."

By the time they left the restaurant, the night had grown cool, and the streets of Springfield were quiet. The moon hung low in the sky, casting a soft glow over the town. Leo suggested a walk, and Edna agreed without hesitation. They strolled side by side, their footsteps steady.

After a few moments of silence, Edna let out a contented sigh, glancing over at Leo. "You know, it feels good to finally get some results. Getting that money for the school is a victory—one I haven't had in a long time."

Leo smiled, his hands casually tucked in his pockets.

"It's about time Springfield schools and you got the attention they deserve. And you were the one to make it happen."

She shook her head.

"No, I wouldn't have been able to do it without you. Honestly, Leo, before you came along, I thought I was going to fail. You showed up and got the sponsors, helped with the plan... it's because of you that we finally got the funding we need."

Leo chuckled, giving her a sideways glance. "You're the one who started the battle."

Edna slowed her pace, her tone more reflective now.

"Maybe. But either way, for the first time in a long time, I feel like I can actually do something for these kids—give them a real chance. Maybe even be a little more hopeful about what's next."

"Hopeful, huh?" Leo asked with a raised eyebrow.

She smiled, a little sheepish. "Yeah, I don't know... it kind of reminds me of how I felt when I first left this city. And I have to admit, it feels good."

Leo gave her an approving look. "It suits you. You deserve it."

Edna chuckled, her eyes glancing at the ground before looking back up at him.

"I guess what I'm trying to say is... thank you. For everything. You've made these past few days a lot easier. It's not everyday someone comes into my life and actually makes me feel like things can change for the better."

Leo smiled. And as they continued to stroll through the dark streets, Leo spoke softly, choosing his words carefully to keep her interested. He complimented her strength, her passion, feeding into what he knew she wanted to hear. 

Finally, when they circled back to the restaurant's parking lot, they found Leo's sleek black luxury car with dark tinted windows standing alone, waiting under the dim glow of the streetlights. The restaurant had already closed, leaving his car the only one in the lot.

He turned to her, giving her a playful grin.

"You know," Leo said softly, stepping closer, "tonight's been perfect. But it doesn't have to end here."

Edna raised an eyebrow, a smirk playing on her lips.

"Got another surprise up your sleeve?"

Leo nodded, placing his hand on her waist as he opened the back door.

"Let's just say I've got a few ideas."

With a knowing smile, Edna slid into the seat, ready for what came next.

[A/N]: This chapter was a big pain in the ass. Holy shit