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[2 and a Half Men] Ch: 63 [First time with Prudence]
🕑 Added 2025-09-26 22:59:02 +0000 UTCAN: SMUT ALERT!!!
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[Santa Monica – Early Afternoon]
Charlie chose a quiet, oceanside café for their first official "date." Not fancy, not candlelight, just a spot with good seafood, strong drinks, and a view of the water. Prudence sat across from him in a sundress, oversized shades resting on her head. The sunlight bounced off her glass of iced tea as she twirled the straw absently.
"You know," Prudence said, smirking, "half my campus thinks I'm some kind of celebrity goddess now. Professors smile at me, freshmen ask for selfies, and the cheerleading squad suddenly wants to 'collab.'" She leaned forward. "Which, for the record, is code for party at their sorority house and make me sing for free."
Charlie chuckled, tipping his beer bottle toward her. "Cheerleaders, huh? I've had some experience in that department. Spoiler alert... they don't get less annoying with age."
Prudence laughed, then sighed. "Honestly, it's exhausting. I'm thinking about dropping out. Just… focus on music. Why waste time in class when I've already made it?"
Charlie's smirk softened into something more serious. He leaned forward, pointing his bottle at her like a gavel. "Bad idea. Fame is like a Malibu wave—it looks big and exciting, but it crashes fast. One day you're headlining, the next day you're the answer to a trivia question. You need your degree. Something solid. Trust me, it's the parachute you don't think you need until the plane catches fire."
Prudence tilted her head, actually considering it. "You're saying I should just grind it out? Even if it feels pointless?"
"Exactly," Charlie said, leaning back in his chair. "Look, you're on top now. But if everything goes away tomorrow, your diploma and degrees are the one thing no one can repo. Besides, brains and talent? Killer combo. Way hotter than just one or the other."
Her smirk returned, sly this time. She stirred her drink, her eyes glinting with mischief. "Well… speaking of hot. You should know something."
He raised a brow. "This oughta be good."
Prudence leaned closer, lowering her voice so only he could hear. "Let's just say this lunch date isn't the most comfortable one I've ever had. Because I might be wearing a little… accessory."
Charlie asked, lowering his beer slowly. "An accessory? What are we talking here? A bracelet? Anklet? One of those chokers that makes you look like you're trying too hard? Or piercings?"
Prudence smirked like she had just scored a point in a game only she knew the rules to. She leaned back, tapped her nails on the table, and said casually, "Nope. Lower. Think… south of the border."
Charlie blinked, tilted his head, then leaned forward again, squinting. "You're not telling me you smuggled jewelry into a body cavity, are you? Because that's usually how vacation stories end in Tijuana… and with handcuffs."
Prudence lowered her shades dramatically, locking eyes with him. "Let's just say it's not jewelry you wear on your wrist."
Charlie froze. His smirk faltered as the implication hit. He set his beer down carefully, as though sudden movement might make the situation worse. "Wait… you're saying… right now? In this cafe? You're walking around with..." He gestured vaguely, hands circling in the air like a man trying to describe an alien spaceship.
Prudence sipped her iced tea calmly. "Wanna see?"
Charlie nearly choked on his beer. “No! No, no, no. This is a family cafe. There are kids over there eating fish sticks shaped like whales. I don’t need a visit from the health inspector because you decided to turn lunch into a rated-R field trip.”
Prudence grinned, resting her chin on her hand. “Relax. I’m just messing with you. You should see your face right now. Priceless.”
He narrowed his eyes. “You’re lucky I didn’t spit beer all over the waiter. I already have a reputation around here. I don’t need to be ‘that guy’ who ruins the kid’s menu.”
She laughed, sipping her drink. “Okay, fine. But admit it. You were curious for a second.”
“I was concerned,” Charlie shot back, pointing at her with mock seriousness. “There’s a difference. Concern gets you to the doctor. Curiosity gets you arrested in Mexico.”
Their food arrived just then. The waiter set down Charlie’s plate of fish tacos and Prudence’s salad. Charlie gave the kid a tight smile, silently praying he hadn’t overheard any of that conversation. When the waiter left, Charlie leaned forward again.
“Look, Prudence. You’re talented, gorgeous, and a little jumpy… which is probably why Berta thinks I’m the only idiot who can handle you. But I need you to hear this. If we’re going to do this… We do this properly. No stunts or games that could end with me on TMZ. Deal?”
Prudence poked at her salad with her fork, smirking. “So you’re saying you want boring dates. Walks on the beach, movie nights, pumpkin spice lattes?”
"You want sex, risky blowjobs in the public elevator, squirting behind a tree in the park, fucking like rabbits in the car, on the couch, sundeck at night... Don't you?" Charlie asked in a low voice.
"I saved my virginity for you," She replied. "And I'm horny. I don't think I can go on by rubbing myself off anymore. I want to do all that you just said with you. Then we can do the dates and movies?"
"Alright," He agreed.
"Alright?" She asked, surprised. She was expecting another delay or more excuses from him, as usual.
"Yeah. Let's do it. Let's finish up here. Then we can go to a hotel and I promise to fuck you till you pass out. Happy?" He replied with a sly smile.
[Hotel] [30 minutes later]
Charlie and Prudence entered the hotel room. The room was simple but clean, a king-sized bed dominating the space. Charlie locked the door behind them, turning to face Prudence. She stood there, her heart pounding in her chest, a mix of excitement and nerves making her hands tremble slightly. He noticed, a small smile playing on his lips as he approached her.
"Nervous?" he asked, his voice low.
She nodded, biting her lower lip. "A little. It's not like I've done this before."
Charlie stopped in front of her, his eyes soft. "We don't have to rush. We can take it as slow as you want."
Prudence looked up at him, her eyes meeting his. "I don't want to take it slow. I've waited long enough. I want you, Charlie. All of you."
A smirk tugged at the corners of his mouth. "Well, in that case..." He reached out, tracing the line of her jaw with his fingertips. She leaned into his touch, her eyes fluttering closed. He took advantage, his lips descending on hers, soft yet demanding. She responded eagerly, her hands finding their way to his chest, gripping his shirt.
He broke the kiss, his breath ragged.
"Let's get you out of this dress," he murmured, his fingers finding the zipper at the back of her dress. She shivered as he slowly pulled it down, his knuckles brushing against her skin. She stepped out of her heels and dress. Then she dropped her bra and panties.
'Fucking hell! Cool down, Charlie. Don't be too excited and burst before going in.'
He smiled, tracing the curve of her neck, his thumb brushing against her pulse point. "You're beautiful, Prudence."
She blushed at the compliment, her hands finding the buttons of his shirt. She undid them one by one, revealing his toned muscles beneath. She pushed the shirt off his shoulders, letting it drop to the floor. She then pulled down his pants and underwear, freeing his cock.
"Wow!" Prudence grabbed his cock, and it was too big. She had to use both hands to grab the entire cock. "Now, this is big."
Without wasting time, she began to suck the tip, slowly flicking the tip of her tongue on his cock's tip before putting half of it into her mouth. She then began to bob her head, sucking him hard.
Charlie let out a low groan, his fingers threading through her hair as she took him in. "Not bad for your first time, Prudence," he praised, his voice hoarse.
She pulled back, a wicked grin on her face. "Well, I did have a lot of practice with cucumbers."
Charlie threw his head back, laughing. "Is that so? I should've known you'd find a way to make this interesting."
Prudence winked, taking him back into her mouth, this time going deeper. Charlie's laughter turned into a moan, his grip on her hair tightening. "Fuck, Prudence. You're going to make me come if you keep doing that."
She pulled back again, her lips glistening. "Isn't that the point?" she teased, her hand continuing to stroke him. "Gimme your cum. I wanna taste your dessert."
She increased the speed of her hand, her tongue swirling around the head of his cock. Charlie's grip on her hair tightened, his breath coming in short gasps. "Fuck, Prudence, you're killing me," he groaned, his hips moving in time with her strokes. She could feel him getting closer, his cock throbbing in her hand. She looked up at him, her eyes meeting his, and the sight of him watching her pushed him over the edge.
Charlie pulled out of her mouth and began to jerk his cock, "Open your mouth and pull that tongue out."
Prudence complied, opening her mouth and sticking out her tongue. Charlie's grip on his cock tightened, his strokes becoming faster. He let out a low groan, his body tensing as he came, his hot seed spilling onto her tongue and into her mouth. She closed her lips, swallowing his cum, her eyes never leaving his.
"Fuck, Prudence," Charlie breathed, his body shuddering as he rode out his orgasm. He looked at her, his eyes filled with a mix of awe and gratitude. "You're something else."
She grinned, licking her lips. "Told you I wanted your dessert."
Charlie chuckled, pulling her up to her feet. "And I want your main course," he said, his voice low and husky. He picked her up, carrying her to the bed and laying her down gently. Then he stood at the end of the bed, looking at that perfect body.
"Like what you see?" She smirked, spreading her legs, showing him the end of the butt plug.
Charlie went between her legs and touched the butt plug before rotating it.
"You horny girl." He grinned, a mischievous glint in his eyes. "I see you've been preparing for me." He rotated the plug again, causing her to gasp. "And I must say, I approve. But I think it's time we get rid of this, don't you?"
Before she could respond, he slowly began to pull the plug out. She moaned, the sensation sending waves of pleasure through her. Once it was out, he tossed it aside and without any hesitation, he buried his face between her legs, his tongue finding her clit.
She gasped, her hands flying to his hair, gripping it tightly. "Charlie!" she cried out, her hips moving in time with his tongue. He chuckled, the vibrations sending another wave of pleasure through her. He was relentless, his tongue exploring her pussy. He was licking and sucking on her pussy lips and clit, bringing her closer and closer to the edge.
"You are so tasty and juicy," He complimented while eating her pussy.
"Yeah? Keep eating then," She moaned.
Charlie complied, his tongue delving deeper while squeezing her boobs and teasing her nipples... hitting that sweet spot. Prudence's grip on his hair tightened, her breath coming in short pants. She could feel the pressure building, her body tensing.
"Charlie, I'm close," she gasped, her hips grinding against his face. He looked up at her. Their eyes met. "Fuck! I AM CUMMING!" She came with a cry, her body convulsing, her inner muscles clenching as she rocked her pussy against his mouth. Charlie continued to lick and suck, drawing out her orgasm until she was a quivering mess on the bed. He then kissed his way up her body, his hands caressing her skin, making her shiver with aftershocks.
He reached her nipples and began to suck. She moaned, her hands gripping his shoulders, her legs wrapping around his waist, pulling him closer. She could feel his hard cock pressing against her, eager for more.
She whispered. "I want you inside me, Charlie. Now."
He grinned. "Your wish is my command," he said, positioning himself at her entrance. He teased her, rubbing his cock up and down her slit, coating himself with her wetness.
Prudence groaned, her hips moving in sync with him. "Stop teasing me and fuck me already," she demanded, her nails digging into his back.
Charlie chuckled, his eyes never leaving hers. He started slowly since she was still a virgin. He pushed forward, feeling her tightness envelop him. She gasped, her body tensing for a moment before relaxing, allowing him to slide in deeper. He moved slowly, giving her time to adjust, his eyes never leaving hers. Then he felt her hymen tear, a brief moment of resistance before he was fully sheathed inside her. Prudence let out a soft cry, her body stiffening at the brief pinch of pain. Charlie paused, concern etched on his face.
"Breathe, Prudence," he whispered, his voice gentle. "It's okay, the pain will pass."
She took a deep breath, her body relaxing slightly. The pain began to subside, replaced by a growing warmth and need.
"More," she murmured, her hips moving slightly, encouraging him. "I can take it."
Charlie pulled back slightly, then pushed forward again, his pace slow and steady. He kept his eyes on her, watching for any sign of discomfort. But all he saw was desire, her eyes dark with need, her lips parted in a soft 'O'.
"You feel so good, Prudence," he groaned, his pace picking up slightly. "So tight, so perfect."
She moaned, her hips meeting his thrusts, her body adjusting to his size. "Harder, Charlie," she gasped, her nails digging into his back. "Fuck me harder."
Charlie's grip on her hips tightened, his fingers digging into her soft flesh. He withdrew almost completely before slamming back into her, making her gasp.
He set a punishing pace, his hips moving with a relentless rhythm, each thrust pushing her closer to the edge.
"Mhmm, yeah. Fuck So good!" Prudence's moans filled the room, her body arching to meet his, her breasts bouncing with the force of his thrusts. "Yes, just like that," she cried, her hands gripping the sheets, her knuckles turning white.
Charlie could feel her inner muscles clenching around him, her body preparing for another orgasm. He reached between them, his fingers finding her clit, rubbing it in tight circles. "Charlie!" she screamed, her body convulsing, her pussy clamping down on his cock as she came. He continued to thrust into her, drawing out her orgasm, his own release building.
"I'm close," He moaned in pleasure. She was too tight.
"Me too," she said.
Charlie increased his speed.
Their bodies slapping together filled the room, each thrust pushing them both closer to the edge. Prudence's moans grew louder. Charlie's breath came in short gasps, his grip on her hips tightening as he pounded into her.
"Charlie, I'm going to... I'm going to come again," Prudence panted, her eyes wide, her nails digging into his back and she squirted hard.
Charlie quickly pulled out and sprayed his cum all over her body like a broken faucet, his body convulsing with the force of his release. Prudence's body was trembling from the intensity of her own orgasm and the unexpected sensation of his hot seed on her skin. She looked up at him, her eyes filled with a mix of surprise and desire.
"That was... too much cum," she breathed, a small smile playing on her lips.
Charlie chuckled as he collapsed beside her, "Phew! Yeah, well... What do you expect? You are gorgeous. You know how to rock your hips and your pussy... God! It was so tight and felt so good..."
"Hehe! Thanks. And I never knew I could squirt. This is the first time it happened," She said while rubbing his cum over her tits.
There was a moment of pause as they just lay there.
"So... What now?" Prudence asked.
"Now, we'll date like not so horny couples. Then, I'll buy a new house with enough rooms for everyone and you'll move in with me. And, I'm gonna love you till the end, plus we are going to have lots of fun together," Charlie said, holding her hand.
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AN: Ok. Sorry for the late update. Won't lie, I'm having a hard time writing this one lol. Never experienced writer's block before. So, it's kinda weird. I'll do my best to drop the next chapter as soon as possible.
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Next Ch: Rose in town
Comments
UnknownMaster
Next time. 👍
Calvin Ellis
and what about the other hole?
Calvin Ellis
❤️Thank you for this moment.❤️
