Chapter content warning: Graphic sex.
"I like your place," Lisa mentioned as Bob helped her out of her jacket. "Very minimalist."
Bob and Lisa had been seeing each other for three months, but this was the first time she'd been to his apartment. Lisa could guess why, but she'd never been hurt enough to be anything but willing, and at times his caution made her impatient.
"Shall I get you a glass of wine, or a juice box?"
Lisa gave him a knowing look. He only made fun of their age difference when he felt uncomfortable.
She sat on the couch while he searched for a bottle of wine in the kitchen. "Actually, Bob, I'm not thirsty." she responded coolly. "I was hoping you would touch me, if you can stomach my youth."
Lisa stared a challenge, but Bob didn't seem ruffled by her suggestion. He joined her on the couch and gently traced his fingers along her hairline to the back of her skull.
"Like this?" he asked, swinging his thumb under her earlobe. She laughed.
"Kinda."
"What about..."
His hand followed the dip in her collarbone to her shoulder and back around, grazing the stem of her neck. She exhaled. Every nerve was alive and ready. Bob leaned in to kiss her jawline as his hands rose past her sides and over the contours of her back.
"Forgive me for taking my time," he murmured into her ear as his fingertips trailed over each rib. "But you deserve to be savored."
He found her lips and kissed her, pulling her into his arms and angling her into more of a reclining position. He felt the planes where legs met hips, the muscles along her stomach, increasing the pressure between her breasts at her hard sternum. Her hips bucked against him and he pulled back. Questioningly, Lisa reached to touch his face, but he caught her wrist and kissed it, pressing it to his forehead between his eyes.
"You are truly beautiful, Lisa Simpson."
She sat forward to look at him. "And you, Bob Terwilliger. I feel like I never knew you until this moment."
Lisa kissed his cheek. Bob shifted her body gently so he could unbutton and unzip her jeans. She hummed in pleasure as he touched her thighs, hips, and belly, sliding up to massage her breasts under her shirt, teasing her nipples, and down again to caress her lightly through her underwear. She was aching, and he rubbed her pussy soothingly, lingering over her wetness. He took plenty of time, and when he finally pulled her last layer aside to feel her bare skin, she cried out, ready to burst.
But he wouldn't let her finish, instead deliberately leading her to peaks and easing her back down, pausing sometimes to explore her body with his hands, or kiss her someplace new.
"Lisa..." he breathed. "I want to taste you."
She kissed him obligingly. When she drew back, he was wearing an expression that read, 'You can't be serious'. She blushed, immediately realizing what he'd meant.
"Oh! Um, yes, please."
He smiled kindly and kissed her again, though she still felt the remnants of a smirk on his mouth. She bit his lip and he retreated, easing off her jeans and making his way down to her pelvis. Lisa moaned softly when she felt his breath against her, kissing her thighs and under her navel. He spread her open and teased her much like before, his touch becoming light or slow the moment she started to shake. She felt his mouth watering and he devoured her hungrily, arms wrapping around her legs to pull her closer. Her nerves blazed, raw to the point of pain; blood rushed from her head. She could feel herself teetering as he gradually backed off, softly nudging her clit with his tongue.
"Bob," she begged. "Please..."
He made his way back to her ear and she couldn't help wailing in anguish. He kissed her temple.
"Shhh, darling... it's all right..."
He began to stroke gently with his fingers, with no sign of denying her another instant. She could feel him growl in appreciation as her pleasure mounted higher and higher, leaving her gasping in shock as the intensity kept growing, seizing for far longer than she expected through wave after delayed wave of warm bliss. Released from her spasm, her heart boomed in grateful relief. Bob waited for her excitement to die down. When her breath became steady again, he drew back and kissed her. She looked at him expectantly and slid her hand along his thigh.
"Do you...?"
"Another time," he promised. Lisa felt ready to faint, so she obediently flopped back to the couch with a sigh.
"That was–"
She stopped when she noticed the pure smug oozing out of Bob.
"Eugh! I'm glad I could help you please yourself!"
He laughed, and the sound was so hearty and healthy that Lisa couldn't help feeling wonderful.
Lisa hauled her bicycle out of the backseat of the cab and onto Evergreen Terrace. It was very late. Her orgasmic zen had already been disturbed by a series of panicked texts. She unlocked the door, already knowing she would find her mother stress-cleaning the kitchen. When she tried to head up to her room, Marge cut her off at the stairs.
"Lisa, I was very worried about you."
"I'm fine, forget about it."
"There are a lot of things I ignore around here, but my teenage daughter dating a predator is not one! Sweetie, don't you think that older guys who go after much younger woman are just a little... skeezy?"
Lisa was mad.
"Mom, while I live in this house I'd like to come and go as I please, and not be hassled about how I live my life."
She stormed up the stairs. Marge followed her, trying to keep her voice down for the other members of the household.
"I'm not trying to hassle you, I'm just begging you to be careful."
"Got it."
"Lisa, please don't shut me out!"
Lisa paused at her doorway, realizing she was literally about to shut the door of her room. Instead, she let Marge enter.
"I know you're more than capable of making your own decisions, but everyone makes mistakes. That's why certain pens have erasers. And I know as your mother I'm fixating on the worst case scenario, but..."
Lisa was sympathetic. It wasn't hard to understand how her mother felt.
"I don't think he's a creep, Mom. I've been the one pursuing him, if I'm being honest. And maybe he used to have anger problems, and sure, he was a teensy bit evil, but he's been through a lot of therapy, and–"
She could tell Marge still wasn't a hundred percent sold on the idea of her daughter dating the man who'd attempted to murder her sister and her son. Lisa switched tactics.
"I'm dating Sideshow Bob and you can't do anything to stop me. I promise I'll be careful."
"Do you have that self defense spray I got you?"
"Yes, Mom."
Marge stole a quick hug after she was hustled out.
"I love you, Lisa. Remember, if he's ever too 'insistent,' tell him you're on your–" She lowered her voice. "p-e-r-i-o–"
"Good night," Lisa said, and shut the door.
