Two and a Half Men: "Charlie Harper and Berta's Granddaughter Prudence" with Megan Fox
(M/F, Cons, Mast, Oral, Teen)
Written by hearsz

Disclaimer: The story you are about to read is not true and it never happen. Anyone easily offended or under eighteen years of age please stop reading as of now. This story does have sexual situations inside of it.

A/N: This is my first story for awhile. I think I've posted maybe two other stories on here. Firstly I want to commend the other story writers on here, you have a far better imagination than I, and I applaud you for that. This idea came to me last week when watching an episode of Two and Half Men from Season 1 and it inspired me to write again. Hope you like it. Hope I didn't overdo the picture inclusions! Enjoy...




The first time Charlie laid eyes on Prudence, also described to he and Alan as, Jake's new "playmate", he knew it was going to be tough to resist her. Seeing those sexy pink lips, that amazingly tight midriff and an all-round body to die for was the least of his problems.

Keeping it in his pants was going to be the main challenge on this particular day.

Prudence's main job was to help her Grandmother Berta clean up around the place, but she wasn't willing to play by the rules and looked to spend more time with Alan's son Jake, rather than do her chores. Acting in a Lolita-like way was having its effect on all three of them.

Jake was infatuated with her, despite his young age, Alan was besotted, whereas Charlie was out if his mind with lust but knew if he didn't take a cold shower soon, he might erupt right there in the kitchen!




Later that day, the brothers wanted to do the work that they're jobs paid them to do. However, the sight of Prudence washing down the outside windows with all that wet soap dripping down upon her delicious body was enough to hold their gaze during their entire conversation.

All Charlie could think about was soaping down that hot little specimen in his shower. But soon he snapped back to reality, knowing that not only was it immoral but quite possibly illegal. Not to mention that Berta would have his nuts in a blender if he even caught him in the same room with her alone!

He sat down to write his latest jingle for a potato chips advert, but just as he went to sit down, Prudence scrunched the moist sponge so the soapy water dripped down the front of her body, all the way down her luscious stems. This caused Alan and Charlie to nearly lose their minds at the sight of this.

Charlie sat down behind his piano, desperate to focus on his music. As he started to play, Prudence knocked on the window asking, "Hey, you play piano?"

Not exactly the sharpest tool in the shed, Charlie responded with an obvious, "Yesss".

As Prudence approached his piano, he started to hit the wrong keys, obviously distracted by the gorgeous teenager before him. "You know I've always wanted to learn to play the piano, do you think you could teach me" said the alluring Prudence, sitting next to Charlie with those seductive blue eyes.




The only thing he wanted to teach her had nothing to do with playing piano, more like what she could learn in his bedroom... He stammered a reply, "Nope, nothing not a damn thing!!" walking away from her quickly, afraid he might cross a line he may regret.

"So do you have a girlfriend?" Prudence asked, secretly hoping he didn't.

"Who, me? Oh yeah, big time girlfriend. We're practically engaged", Charlie uttered. He quickly made up an excuse to get out of have to answer with the truth.

A look of disappointment crossed Prudence's face and Charlie certainly noticed.

Berta broke up the conversation letting her granddaughter know that he was old enough to be her father and knowing her mother he probably is! She then instructed her to get back to cleaning the windows.

Berta ducked out to the shops to fetch Charlie some groceries but to make matters worse for the boys, Prudence decided to strip down to her bikini top and bottoms and get herself a tan out on the deck. Berta had already warned Alan not to do anything stupid, but it was becoming all too much for Charlie.




Lying back painting her toenails, she chatted with the innocent Jake as he looked up and down her saucy tanned stems, those perfect pins he desperately wanted to touch. He may have been young, but seeing this stunningly hot girl in front of him scantily clad had him mesmerized.

Unfortunately for Jake, his father ordered him to finish his book report for school.

Alan headed outside to bring Prudence another fruit juice, even though Charlie had initially resisted.

As Alan stepped outside onto the deck, he couldn't help but gaze at the striking teenager, all laid out on the deck chair, her hot sweaty body taking in the warm sun.

Her gorgeous face, with eyes closed would usually be enough for someone like Alan to come on the spot, but due to the shock of seeing this delicious young woman in this state, was enough to restrain Alan from reacting for now.

Alan handed Prudence her drink, and she asked where her little friend had gone to. Alan told her that he had work to do, much like Prudence herself. Looking up at him with those heavenly blue eyes, she replied, "Ohhh, are you going to tell in me?"

Hesitating he said, "Oh no, no, no, just an, an observation". He continued to mutter a response, as he tried to sneak a peek at her impressive cleavage. Prudence's breasts were developing really well for a young female and as he thought about this, she said him, "What are you talking about?" not understanding a word of his rambling.




Alan tried to give her some advice but all she was concerned about was not getting sunburnt.

Picking up the sun cream lotion and turning around so her back faced Alan, she held up the lotion asking him, "Can you put some of this on my back?" He quickly retorted, "Nooo!"

"If you don't I'll burn." In reply, knowing the consequences if he did as she asked, he replied, "If I do, I WILL".

Later that afternoon, Prudence went to Jake's room to help him with his book report. Alan and Charlie would be happy to have her out of the way until Berta arrived back and figured she couldn't get into too much mischief in Jake's room.

When she first entered his room, it wasn't what she expected. She loved the fact he played electric guitar and had a really cool amplifier, but there were numerous posters of bikini models on his bedroom walls.

She actually felt comfortable with this as she figured he was comfortable seeing her in nothing but a sexy bikini herself earlier that day.

As Prudence finished helping Jake with his book report, she lay back on his bed, her legs parted slightly and her firm toned stomach manage to catch the youngster's gaze once again. At that moment Jake felt a stirring in his pants and used his hand to fix his erection. Prudence noticed this and as she sat up she asked, "Everything alright handsome?"

Jake hesitated in his reply as Prudence moved closer to him. "Do you find me attractive stud?" and put her well-manicured hand on his young shaft on the top of his shorts. In a sweet voice she said, "It's okay, I won't hurt you. Just promise you'll keep this between you and me ok?"

"Uh-huh," the young man replied. Taking her hand off his cock, Prudence asked him, "so do you have a girlfriend?" not even considering the fact he was only young. "Ewww, no yuck."

Prudence giggled at his reply.

"Ok then, so I take it you've never seen a woman topless before?"

Jake's eyes lit up hearing this. He told Prudence he had only some things in his father's men's magazines before, but that was it.

Prudence moved to the door, locking it to make sure no-one walked in on them.

In her sweet sultry voice she said, "Ok now close your eyes handsome".

Jake did so and as he did, Prudence undid the front of her blouse and bikini top to expose her succulent perfectly shaped breasts, "Now open them".

Jake could only stare in astonishment at seeing his first ever pair of woman's breasts in the flesh.

"You like?" asked Prudence.

Again all Jake could mutter was "uh-huh".

Prudence let Jake play with her breasts for a while, his eager young hands relishing the chance to fondle her soft tit-flesh. She didn't want to completely violate the poor kid, she just wanted to give him a thrill and something to remember her by.

"We have to wrap this up little buddy." she said, even though he continued to grope at her chest.

She continued, "But here's something to remember me by", as she leant in to deeply kiss the youngster with her pouty pink lips.

His young hands tensed upon her heaving breasts as she licked her moist tongue inside his mouth. Jake was completely blown away by this and he opened his eyes just as Prudence opened the door to leave.

The last thing Jake got to see was Prudence' sexy calves and perfect ass leave his room, saying to himself, "Wow, I really hope I get a chance to tap that when I get older...."

Once Prudence finally left with her Grandmother, the two brothers and Jake were left to get on with their lives, or so it would seem.

Jake slept soundly, dreaming of the day he would see Prudence again, hoping she would show more of what she had to offer. However Alan and Charlie weren't taking it so easy.

For Alan, seeing that hot piece off ass in nothing but a two piece bikini was the best thing he'd seen since his college years.

Not even his ex-wife put on that kind of show for him. Finding it hard to sleep, he knew he had to calm down.

He decided to hop into the shower to relieve some tension. As the warm water hit his skin, he closed his eyes, imagining that remarkable teenager in that sexy bikini. He envisioned her licking her lips as she looked up at him, shifting those statuesque legs back and forth on the deck chair, stroking her tender fingers upon her taut stomach.

Whilst he imagined this he stroked his now elongated cock, although only stretching to five inches at most, the soap he had rubbed upon it moments earlier made it easier to get a slick motion going.

"Do you want me Alan?", the imaginary Prudence asked him seductively.




"Oh God Yes!" Alan responded as the shower water poured upon him, his stroking becoming faster as he thought about those precious pink lips, that amazing cleavage and that delightful teenage ass of hers.

In his mind, he fantasized all the things that she would never consider saying to him, whatever it took to push him over the edge.

"Alan, your cock looks so yummy, do you want to put it in my dirty little mouth?"

"Unghhhhhh!!" That was enough for Alan to climax and shoot his cum out and onto the shower wall.

Once his orgasm subsided, Alan cleaned himself off and redressed himself into his pyjamas, ready for bed. Once in bed, he could hear Charlie having sex with someone upstairs.

"Probably one of his late night booty calls", Alan murmured to himself.

He was used to this by now. But thanks to his incredible session in the shower, he knew he could sleep well till the morning and within a few minutes, he had passed out.


************************************************** ************************************************** *****************************


As fate would have it, the moment Alan had entered the shower, Prudence entered Charlie's house, around two o'clock in the morning.

Fortunately for her, Charlie had left the front door unlocked after returning from the bar. She had run away from her mum's house and knew she had to see Charlie again. Seeing him for the first time that day she was immediately attracted him.

She would hear her grandmother's stories of the number of women he had slept with and figured if anyone was to satisfy her sexually, he would be the man for the job. Prudence silently moved up the stairs and she could have sworn she could hear running water and moaning coming from downstairs.

She ignored it and proceeded to Charlie's bedroom.

Charlie had drunken quite a lot that night. Committing himself to excessive amounts of alcohol usually helped him forget about women but this time he couldn't shake the image of Prudence and her sitting next to him at the piano asking her if she could "teach her" how to play.

He knew what he'd like to teach her if given the chance.

He drunkenly lay in his bed imagining what he would do to her if he was allowed to. What positions he would take her in, what he could teach her.

The alcohol, some drugs he'd never tried before and lewd thoughts of Berta's granddaughter were all too much for him. Charlie at that point decided to get up and go to the bathroom.

As timing would have it, Prudence had opened up Charlie's bedroom door, looking to hop into bed with him and hope that he would just go with it without realising it was her. However, she saw his bathroom light was on, so she knew he wasn't in his bed at that time.

Prudence quickly stripped off her clothes, leaving her clad in her favourite frilly black and white bra and panties, that she specifically picked out for this occasion. She lay across his bed, waiting for him to return to the bedroom.




Wiping his water soaked hand across his forehead that he had just had under the facet, Charlie looked to return to his bed. Entering the bedroom, he was seductively greeted with a, "Hi Charlie, I've been waiting for you", Prudence remarked.

Charlie through astonished eyes reacted, "No way... I've been dreaming about you! Am I still dreaming now??"

Prudence, not wanting for him to slip through her fingers again played along,

"Yes Charlie, you are dreaming. This is your dream and you can do whatever you like to me. I'm all yours".

Charlie looked this sexy brunette up and down, ogling her appealing young body, the way that exquisite lingerie looked upon her hourglass figure.

He thought of the first thing that came to mind.

"I don't suppose you would want to suck me off right?" he asked in an unassured manner.

"Of course, whatever you desire," Prudence responded as she moved toward him, leaning up to kiss him deeply with those sexy pink love cushions, massaging her moist tongue with his. She took his hand to bring him back towards his bed. Prudence sat on the side of the bed, Charlie's belly in line with her gorgeous face.

Prudence traced the outline of his massive erection with her subtle fingertips, squeezing the enormous package that was desperate to be released from its cotton constraints. She kissed and licked upon the bulge in his boxers, eliciting a moan from Charlie.

"Wow", he thought to himself. Off all the fantasies of women he usually could never have, this one felt the most realistic.

"Show Prudence what all the girls rave about Charlie", she asked erotically as he slid his boxers down, revealing his 12-inch monster.

"Oh my god, no wonder you have so many girls after you", she said out loud. Charlie drunkenly grinned at the remark.




Prudence reached up to put her soft fingers around the thick shaft, Charlie uttering a deep moan as she pulled his foreskin back and adoringly stroked his big cock back and forth.

She temporarily released his cock to spit on her hand, allowing the saliva to help stroke him smoothly and with more vigour. The beautiful teenager used her other hand to tickle Charlie's nuts, feeling his erection throb once she did this.

"Ohhhh God that feels good", Charlie groaned.

Prudence licked her lips, making them nice and moist in preparation for the monster that she wanted invading her warm wet mouth.

Charlie could feel her cool breath upon his naked manhood and again he thought to himself that this felt more realistic than his normal sex dreams. However, he convinced himself that it was best not to question it and just to enjoy it whilst it lasted.

Prudence extended her wonderful tongue and coated Charlie's bulbous head with her saliva, licking all around the spongy tip.

She did this for a while and then really started to go to town on his beast. Opening up those fabulous pouty lips wide, she wrapped them around the thick shaft and took a quarter of his huge cock inside her, making sure he felt every bit of suction her mouth had to offer.

The teenager kept her eyes closed and concentrated on pleasuring Charlie, moving her spare hand to caress his backside as she started to take his dick in deeper.

Despite his heavy intoxication, Charlie knew this girl was one talented cocksucker. It was his fantasy so of course she was. However, she was a lot better than other girls that have gone down on him not only in his dreams but also the ones who had done it for real.

"Oh man, Berta would kill me if this ever happened", he gasped.

Prudence heard Charlie loud and clear, and tried not to laugh around the cock that was buried three quarters deep inside her drool covered mouth.

She desperately wanted to deep throat his entire length, and was caught by surprise when Charlie persuasively moved his hand to the back of her head and helped her take his entire pole, the tip hitting the back of her throat. He face fucked her for what felt like ages, savouring every bit of the deep recesses of the teenager's hot wet mouth and delicious lips.

Despite earlier gagging, Prudence was really getting off from this and alternated by playing with her pussy through her now moist panties and tweaking her hard nipples.

Sliding that huge schlong out of her mouth, a long string of saliva followed. Prudence had a hunger to taste and suck on Charlie's balls. Pushing his erect shaft up against his belly, she affectionately teased his testicles with her tongue, running around them in circles and even licking under the sacs so they sat in the centre of her wet tongue.

"Oh Prudence, how did you know I liked that so much?" Charlie whimpered, feeling her gorgeous plump lips close around his left nut, tea bagging it as she slowly stroked around the tip of his cock with her silky hand.

Prudence did this for a few more minutes but soon felt some dampness between her legs. She wanted to make this a "fantasy" Charlie would never forget.

Lying on the edge of the bed, Prudence spread those long legs, exposing her supple thighs and her exquisite little silk panties. Meanwhile, the drunken Charlie stood there taking the amazing sight in. "Wow, this is graphic!" he gasped.

"Charlie? Would you like to watch me play with myself?" Prudence asked seductively.




A dazed and clearly elated Charlie could only nod as he watched the luscious teen caress her perfect body slowly, running her hands up and down her hips, across her stomach, and in between that saucy cleavage.

She squeezed those firm breasts tightly, her eyes tightly shut as she pinched her nipples through that sexy little brassiere. With her legs splayed wide, she lightly stroked her inner thighs and it was at this moment Charlie took a hold of his still erect shaft, and began stroking it.

Megan flashed her dazzling smile at this and lifting up her silk underwear, she slipped a hand inside, and began deftly stroking her pussy lips, and playing with her clit. Biting her bottom lip with her eyes closed, she darted her middle finger inside her dripping cunt, her breathing and moaning intensifying.

She was really putting on a show for Charlie, pulling her panties to one side so Charlie could see each time her long finger disappeared and reappeared from her sex.

With her eyes closed as she played with herself, Charlie knelt before her to get a close-up of this stunning teen pleasuring her wet pussy. He inhaled the musky aroma and knew he wanted to savour the sweet nectar for himself.

Prudence opened her eyes to see Charlie kneeling between her legs. She knew she had to feel this older more experienced man take her to pleasure town. She flashed those pearly whites, which pretty much gave him the go ahead to do as he pleased.

Sliding those wet panties up and off those long perfect legs, throwing them to the floor. Charlie ran his hard fingers over Prudence's tender hairless pussy lips, eyeing a drop of her juice that trickled down the inside of her tight sweaty thighs.

He couldn't wait any longer, and dropped his mouth to that delightful teenager's twat, parting her cunt with his hard tongue, a loud moan filling the room and no doubt the whole house, as Prudence experienced a sensation that she had never felt in her young life.

Holding each of her great legs in his hands, Charlie tongue fucked Prudence sopping cunt with deep strokes, making her sob harder with each lash of his tongue. He sucked on her clit making her yell out, "Oh fuck, that feel so good, unghhhh!!"

Charlie pleasured the young woman's pussy for what felt like an eternity, Prudence out of her mind with desire for this older man, her eyes rolling into the back of her head at times.
"Charlie, I need your cock now! Fuck me! I want it so bad!!" Prudence yelled.

Not one to resist, Charlie scooted between the teenagers legs and positioned his cock at her entrance. Normally he would be wise enough to use protection, but since he thought this was a dream, he felt there wouldn't be any consequences.

Charlie took one last look at Prudence, that striking young face, waiting in anticipation to feel his manhood to delve deep inside her for the first time. Charlie, who was pushing forty, was about to have the ultimate sex dream with a stunning desirable young female more than half his age.

"Time to make you a real woman," Charlie said, Prudence smiling wide as Charlie's thick member ploughed slickly inside Prudence's warm tight cunt.

"Unghhhhh" she groaned, never having felt such a cock this huge invade her before.

The young beauty still took half of Charlie's dick in with the first thrust, and with each movement after that, her cunt took more of him in. She draped her arms and long legs around him, adjusting to the pounding Charlie's huge meat was giving her.

Charlie savoured Prudence's inexperienced cunt, which wrapped resolutely around his shaft. It was extra special to fuck this hot teenager without any protection.

This was one of the best dreams he'd ever had. It felt so life-like and he couldn't believe he hadn't woken up yet. It was usually around this time that he'd wake up next to his stalker Rose or Berta bursting in his room to collect his laundry.

He fucked Prudence deep and hard, his thick cock stretching her pussy to its limit. She felt quite some discomfort but it was subsiding with each stroke and she couldn't help but fiddle with her clit as she watched Charlie slide his cock in and out of her.

Without any warning, Prudence somehow managed to flip Charlie over so that she was on top and in control. Reaching behind her back, she spoke, "No doubt you've been waiting to see these all day?" And with that, she undid the clip to her sexy bra, revealing her perfectly formed breasts.

Charlie's hazy eyes lit up, taking in the amazing sight of the teenager's fabulous pair of tits on her equally superb body. His cock twitched in reaction to the view of Prudence's hard nipples, and she in turn felt it deep inside her. "Ooh, someone likes what they see", she cheekily responded.

Leaning down to kiss him, Charlie reached down to grope her round succulent ass cheeks, squeezing them to his pleasure as their tongue's wrestled and she began sliding up and down his hard boner.

Prudence leant back up to gyrate her body upon Charlie's gigantic organ, uncontrollably moaning at the effect it was having on her. She took his hands and placed them upon each of her heaving breasts.

Charlie pinched and tweaked those rock hard nipples, whilst thrusting his cock up inside her as she thrust herself downwards. Her cunt was completely impaled upon his thick rod, her wet juices exiting her slick cunt and upon his abdomen.

She reached down behind her to caress his hairy balls and Charlie reacted accordingly at her soft touch, slamming into Prudence's wet sopping vagina to the point she was squealing in ecstasy.

Charlie rose up slightly so he could suck on those mouth-watering breasts. As he feasted his eager mouth upon one tit, he squeezed and fondled the other, never stopping his inward thrusting inside Prudence's heavenly cunt.

"Oh Charlie, that feels amazing," the desirable teen moaned as Charlie lapped his tongue around her hard pink nipple.




"Oh God Fuck Me Charlie, I love it, oh it feels so deep inside me," the not so innocent teenager wailed. Prudence was experiencing multiple orgasms for the first time in her young life, but she knew after two hours of amazing sex, that Charlie wouldn't last all night.

Hopping off her Grandmother's employer, Prudence moved to the end of the bed on all fours, raising her delicious ass up in the air, presenting it invitingly for Charlie.

"C'mon Charlie, fuck my pussy hard, I want you to ram it hard inside me again like this", Prudence implored, her lips quivering, acting like the nymph she secretly was.




Charlie took one look at that flawlessly formed behind, that juicy wet slit and knew what he had to do. Kneeling behind the luscious teen, Charlie took a hold of his pulsing cock, and as he rested his head at her entrance, he took hold of Prudence's hourglass hips and in one swift motion, sank all twelve inches deep inside her warm opening.

"Unghhhhhh, oh my fucking God you're sooo fucking huge Charlie!!" Prudence exclaimed.

It was possible she had yet another earth shattering orgasm in that single movement. But she wasn't able to savour it as Charlie pounded the hot brunette from behind like the end of the world was coming. Charlie rammed Prudence's soaking cunt, spanking her sweaty arse as well.

"That's it Charlie, spank me, I've been really naughty, I'm a really bad girl, punish me with your big cock!!" Hearing Prudence' dirty talk was pushing him over the edge, especially when she reached down between their hot and heavy bodies and began fondling his swaying nutsack.

"Ohhh God I'm gonna cum!!" Charlie shouted.

Not wanting to run risk of getting pregnant, Prudence quickly defused any possible repercussions. "I want to taste it Charlie", Prudence demanded. Charlie retracted his horny cock from Prudence's entrance and stood in front of the bed as Prudence got on all fours in front of his vast member.




Taking the slippery shaft in her hands, she opened her mouth and sucked the head of his cock, urging him to cum for her. "C'mon Charlie, don't you want to cum on this pretty teenager's face, on her gorgeous tasty lips? I want to feel you splatter all over me" Prudence said eagerly.

"Unghh, here it comes", Charlie responded and taking a hold of his shaft, he shot his load all over the beautiful teen's pretty face and upon her pouty pink lips, her tongue lashing the head as a torrent of cum exited his shaft.

When Charlie's orgasm finally ended, Prudence took control of his softening dick, cleaning it up with her talented mouth.

"Thanks Charlie, you were amazing like all the girls say you are", Prudence said.

"What can I say, I have a gift!" he replied cheekily.

"Now lie down and go to sleep, you deserve it", she advised him.

Not wanting to argue with his unbelievable fantasy, Charlie pulled the bed covers over himself and within seconds passed out.

Waking up the next morning, Charlie arose to the sound of Berta knocking on his door. She was doing her usual routine of coming in at eleven to collect his laundry.

"Charlie, you better be up in two minutes because I am coming in!"

Charlie turned to his side, hungover like most mornings but then he remembered his "dream".

"Wow… that was certainly different. But also very real! Did that really happen?" Just as he was about to dismiss any thought that he had sex with Berta's granddaughter in his bed, he noticed a piece of clothing on the ground. It was a pair of black and white silk panties.

In shock he shouted out "Oh Shit!!!" Before he could hide the evidence, Berta walked in on him, as he held up the pair of sexy panties.

Trying to not look to guilty, he said to Berta, "It's not what it looks like Berta!"

She nonchalantly replied back to him, "What? You had another whorish floozy over again? What else is new!!", and carried on to his bathroom to clean up after him.


The End