The Cheryl Cummings Story: Early Years Ch. 06

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Nis 8, 2021 // By:analsex // No Comment

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*** Bad Grades – what to do? ***

After the prom, Cheryl became less and less interested in schoolwork and more and more interested in her new boyfriend Chris. It came to a head when Cheryl’s mom, Jane received a progress report on Cheryl in the mail. It seems Cheryl was failing in her math class with a low D. This came as a major concern to her mom, because up to this point, Cheryl had always been a straight A student. Jane knew she had to do something because her daughter was becoming more and more resistant to her authority and seemed to be hiding things from her mother. Up until recently, this had been entirely uncharacteristic of the girl, and Jane was concerned.

When she asked her friends for advice, she was given some that she did not expect! “You should have Bob (Cheryl’s step-father) deal with it. He needs to become more involved with his daughter, and frankly, help you out a bit with this. Girls tend to respond better to their fathers at this age. They tend to trust them more.”

Jane had been debating this idea for the entire day. When Bob got home from work, she called him aside and asked his opinion on it.

“Hmmm…well, I think I could probably handle it – and I will – under one condition,” replied Bob.

“What’s that?” asked Jane.

“That you let ME handle it. That you turn it over completely to me, and let it be between Cheryl and me. That means you act like you know nothing about it, and let me deal with it in my own way. If you’re going to have me start it, then jump in and change everything, then I don’t think it will work very well.”

“OK, deal. I KNOW NOTHING!” laughed Jane.

“I’m serious. This means you can’t ever mention it to her, you can’t bring it up at all. You have to allow me deal with it entirely.”

“I got it,” laughed Jane.

“OK. So tonight when she gets home from school, you make yourself scarce – and I’ll bring it up to her and see how it goes.”

“All right. But you at least have to let me know how it goes.”

“Deal. But NO talking to her about it.”

“You got it big stuff!” grinned Jane, as she reached for Bob’s ever willing to respond manhood. Just as he started to harden, they heard Tawnee and Cheryl arriving home.

“As usual,” thought Bob to himself. His and Jane’s sex life had been anything but overly active these days. Having two teenage daughters – who were ALWAYS around – kind of got in the way a bit. By the time Jane and Bob had a moment alone, Jane was always exhausted and wanted very little to do with sex. Bob was feeling like he could just about climb a tree!!

“HI mom! Hi Dad!” announced Tawnee, bounding through the door and kissing each of them, in turn, on the cheek.

Cheryl, as usual, kinda snuck into the room and tried to make her way to her room without being overly noticed by her parents. She figured, the less she talked to them, the less they could hassle her.

“Hey Tawnee, I need your help doing some shopping today!” said Jane to her youngest daughter. Jane knew one way to very easily persuade her youngest daughter out of the house without having to divulge the slightest amount of information to her.

“Clever,” thought Bob to himself.

“OK!” responded Tawnee, ever willing to shop! The pretty young teen made her way, with her mother, out the door to the family car. Bob rather quickly heard the engine start up, peered out the window and watched his wife and youngest daughter drive away, leaving Cheryl alone in the kitchen with her step father.

Bob couldn’t help but notice how much his daughter had grown up this year. She certainly was growing into a beautiful young woman. She looked just like his wife, only 20 years younger, and 15 pounds lighter and – well, quite a bit firmer. In a word, the teen had become scorchingly HOT!

Not really sure how to breech the subject with his daughter, Bob just went straight to the heart of the matter – “You know your report card came in the mail today,” started Bob.

“Terrific,” replied Cheryl, rolling her eyes.

“You realize you’re failing math?” he asked.

“Yeah. So?” asked his daughter, immediately challenging him. “What do YOU care anyway?”

“Young lady, I care a lot about your grades!” responded Bob, feeling himself growing angry.

“Since WHEN? You’re not my dad!” demanded Cheryl.

Her response so caught him off guard that he just stood there, glaring at his daughter.

Feeling himself already losing the battle, Bob started grasping at straws – “You’re mom’s not going to be too thrilled with it, you know?”

“Since when is she EVER thrilled with ANYTHING I do? Look, I’m going to go lay out for awhile,” said Cheryl as she bounded out of the kitchen and headed toward her room.

Bob was completely taken aback. He did not at all expect the responses he got from his stepdaughter. And she was so grown up looking that he found it hard to be too harsh with her. She was a young woman…a very attractive and bull headed young woman who somewhat overwhelmed him a bit.

He stood keçiören escort in the kitchen as he heard the back door open and close. He simply stood there for a moment pondering what his next move should be. He decided he should talk more to her…so he walked to the back sliding glass door that led out to the deck, meaning to march right out and confront his eldest daughter.

When he got there though, he simply froze in his tracks. His daughter was laying out in her black and white two piece bikini. Not such a big deal – he had seen her in it dozens of times. But today, she looked completely different.

As he stood, staring out the back door, he took in her beauty, as if for the very first time! She lay on her back, facing him, with her eyes closed to shield the sun. Since her eyes were closed, he was able to stare at her from head to toe and back again, lingering wherever his eyes chose to without being concerned with anyone catching him looking. This was such a rarity to be able to look at a young, scarcely dressed beauty that he simply stood there, riveted to the sight before him.

Her beautiful, straight blonde hair fell all around the chair completely surrounding her, seeming to highlight the young and innocent beauty. Her face was perfect. Nice long neck…that seemed to just travel down to the most incredible set of breasts he had ever seen in his life. He didn’t know how big they were, but he was certain they were now larger than her mothers were – and–much firmer with no sag at all.

He didn’t realize it, but at the moment his eyes met with her breasts, his hand started stroking his rock hard cock through his dress pants. It was throbbing, and pre-cum had started to leak out.

As she lay there, she reached up and adjusted her suit, lifting her breasts up, reaching under them, and wiping away some sweat from underneath her large, firm, tits.

When she moved her hands away, he could clearly see the underside of both her tits, they were now outside the tight bikini top! He could see the bottoms of them, practically up to the nipples that he could clearly see protruding through the fabric of the suit.

At this point, he slid his hands down his still done up pants, fished his way into his underwear, and grabbed his throbbing cock, squeezing more pre-cum out of it. The pre-cum lubricated his hand a bit, and allowed him to actually begin masturbating as he stood there.

“GOD, I want her!” he said out loud to himself as he stood there, studying her laying not 10 feet away from him.

As she continued to lay there, she brought her knees up a bit, and parted them slightly. He found himself staring at the narrow piece of fabric that contained her sweet young pussy.

“MMMM,” He let out a low moan and continued working his cock with his right hand. He knew if he kept this up, he would shortly cum in his pants. He had to get ahold of himself and figure out what in the hell he was going to say to this girl!

Reluctantly, he took his hands out of his pants and walked away.

Twenty minutes later, he found himself back at the window, discovering that she had now turned over on her back, and her firm, young, perfect – and only slightly covered – ass was staring straight back at him.

Again, he found his hand in his pants pulling on his hard cock. Only her starting to get up from her chair roused him this time. He was on the verge of shooting into his palm when the girl started getting her stuff together to come inside.

Being the mature man of the house that he was, he ran to his bedroom to hide! He decided that two could play at this game though.

As he ran into his room, he left the door cracked, pulled off his shirt and pants, leaving only his bikini briefs on. He had dark blue, fairly tight, bikini briefs that really showed off what he had.

At the moment, he had a HUGE hardon! He lay down on his back on the bed, and pretended to be in a deep sleep – just to see how his oldest stepdaughter would respond.

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

*** Taking a nap ***

Bob had this special trick he could do with his eyes. He could pretend that he was lying there asleep, with his eyes closed, when in actuality, they were slightly open, allowing him to see everything going on in the room.

He used to use this trick on his parents all the time when he was a teenager. He would pretend to be asleep on the couch and watch his parents until they went to bed, then sneak out.

As he lay there, with a semi-hard cock, in his bikini briefs, he heard her open up his door to come in to try to talk to him. Then, seeing him laying there asleep on the bed, she stopped short of calling out to him.

Instead, she stood there, for just a second, checking to see if her stepfather was indeed, actually asleep.

She had not changed from her 2 piece bikini, so as he quietly watched her standing in his room, he was getting a very interesting eyeful of her chest as she bent over the bed, looking keçiören escort bayan to see if her was asleep.

In fact, her tits were practically falling out of her bikini top! As he peered down her top, he could see all of both of her breasts dangling before his face.

The swimsuit separated from her slightly on the right side, allowing him to even see her pointedly hardened right nipple. It was all Bob could do to suppress a slight moan as he took in this sight of virgin beauty.

The family dog had wandered into the room, so Cheryl suddenly crouched down right next to the bed to pet the dog, again, giving Bob an excellent view of her magnificent charms. Bob could feel a major hardon well on it’s way.

Bob still pretended to be asleep, only slightly opening his eyes so he was able to watch what Cheryl was doing.

She would pet the dog and rub his back and then glance over at where he was asleep. Bob started to think that it was slightly peculiar that she was staying in his room so long – just petting the dog.

Suddenly, Cheryl got up and walked over a little closer to her stepfather. From time to time she would look to make sure his eyes were closed and he was still asleep.

Bob played the game well and could pretty well track where she was as she moved to the end of the bed. He opened his eyes just a slit again and saw Cheryl seemed to be staring intently toward his crotch area. Bob knew immediately what she was looking at.

From the position Bob was laying on the bed and due to the fact that his cock was by now three quarters of it’s full eight hard inches, he realized Cheryl was getting a good indication of what his cock looked like through the outline in his tight bikini briefs! This sudden realization made his cock twitch a bit and become even more hard.

About that time Cheryl heard a noise in another room and she quickly left.

“Damn,” Bob thought to him self as he saw her walk out of the room.

Bob reached down and adjusted his cock – moving it slightly closer to the leg opening of his briefs.

He heard Cheryl coming back toward where he was laying. Apparently satisfied she was safe she entered the room again and began petting the dog again. If Bob had woken up, she could have told him she was simply checking on the dog.

Bob watched her through the slits of my eyes. Soon, she got up and walked toward the end of the bed again. This was his opportunity.

He acted as if he were simply scratching in his sleep, bringing his hand over to scratch his balls. Cheryl started back a bit at this point, but didn’t leave entirely – checking to see if he was asleep or if he had awakened.

She must have decided he was still asleep, as she crouched a bit closer again, just as Bob reached inside the side of his briefs, freeing both his cock and balls to the afternoon air – as well as his curious stepdaughters gaze. As his cock sprung into view, Cheryl let out a slight gasp.

Soon Cheryl had worked her way back to the end of the bed again and was staring intently. Bob acted as if he were scratching again – in his sleep.

Only this time, he left his hand resting on top of his cock that was now exposed from his briefs. He gently squeezed and slightly pulled on his hard dick as his stepdaughter stared with rapt fascination at the spectacle before her.

Cheryl stared fixedly at Bob’s hand. She would look apprehensively toward his eyes, then back to his crotch. Next, Bob began to scratch the top of his now fully exposed cock. When he had finished this, he left his hand on top of his completely hard cock.

Cheryl remained almost frozen in her spot, looking at his eyes then back to his cock then back at his eyes. Next Bob froze in that position acting as if he had fallen into a very deep sleep.

His hand covered only part of his cock and a few inches of it extended beyond the end of his casually placed hand.

Bob lost sight of Cheryl as she bent closer to examine his exposed cock. Was it his imagaination? He could almost swear he felt her warm breath on the head of his exposed cock.

He wasn’t sure how close she got to it, but he could tell it had been very close. Then as quickly as it began, Cheryl left. He heard his door shut and then heard her closing her own bedroom door.

At first Bob was a little nervous about the whole episode. He was not sure what Cheryl had thought. The only thing he did know was that the end of his cock was dripping pre cum.

Bob only discovered this after she had left. His mind raced with thoughts of what she was thinking. Hey, she was the one who looked. Hell, he thought to himself. I was asleep.

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

*** A Nocturnal Visit ***

Bob decided that he truly would take a brief nap until his wife and youngest daughter returned from shopping. He gathered his cock and balls back into the confines of his briefs, rolled over, and almost immediately fell into a deep sleep.

A escort keçiören few hours later Jane and Tawnee returned from their shopping adventures. Jane found Bob dead asleep, and woke him up to find out how things went.

“How’d the report card mission go?” asked Jane.

“Slow. I’m working on it. Give me a bit more time and we’ll see if I can’t get this thing straightened around,” answered a groggy Bob.

He had gotten a couple of hours of sleep to prepare for the mission he was planning for later on this evening.

“OK. I’ll stay out of it, just like I promised,” answered Jane.

“Excellent. I have a few things in mind to try to bring her around. Let’s just hope they work,” answered Bob – trying to suppress a lecherous grin.

The rest of the evening went as most all others. Jane and Bob worked together on fixing supper while the girls worked on their homework in their room.

Jane and Bob quietly discussed how withdrawn Cheryl had become of late. The girls quietly discussed other matters.

“Do you think Bob’s good looking?” asked Cheryl of her younger sister.

“Hell yeah. Mom did pretty good for herself, I think!” answered Tawnee. “If he weren’t my step dad, I’m thinking I’d do him.” Grineed Tawnee.

“You are so impossible” laughed Cheryl. Why couldn’t she be more like her younger sister. So free spirited. So willing to take risks.

The hugest risks she’d ever taken was getting off the prom dress guy to get a good deal on her dress…then this afternoon peeking at Bob’s cock.

She couldn’t get over how much that had effected her. She was so hot and horny…she immediately went to her room and started playing with her pussy.

Unfortunately, the phone had rang almost as soon as she started. Chris was calling just to see how she was. By the time she had gotten off the phone with him, her mom & Tawnee had returned so she didn’t get a chance to have a really good cum.

And she REALLY needed one. Her pussy was simply on fire. She kept seeing Bob’s rock hard cock….just inches from her face. She had been so tempted to reach out her tongue – and just touch the end of it. It took all of her will power to resist the urge as she started at it – just inches from her mouth.

Suddenly Cheryl realized she was day dreaming again. If she didn’t get back to her homework her parents were going to simply kill her. She knew her grades had suffered lately, and she knew she needed to focus on them again. It was just kinda hard with all these hormones raging all the time!

The only time she ever seemed to be alone was late at night when she was laying in her bed. Tawnee was never shy about relieving her frustrations, but Cheryl still felt a bit shy to do that.

Often she just couldn’t help herself and would simply have to play with her hot little pussy as she lay in bed listening to her sister very loudly satisfying herself.

But she really didn’t want her sister catching her doing it again and teasing her about it. So normally she tried to wait until she was sure Tawnee had drifted off to sleep before she took care of her needs. And many times, she got so tired, she simply fell asleep.

Tonight was no different. Almost like clockwork, she heard Tawnee masturbating above her. As the bed rustled and the moaning reached a crescendo, Cheryl simply had to touch her own dripping pussy.

She was soaked, and completely out of her mind with horniness. As her finger made contact with her wet pussy, she knew she could not be quiet.

A low moan already escaped her lips, but fortunately, Tawnee was uttering her own as her own orgasm shook over the young teen. Cheryl pulled her hand out frustrated. Again, she would have to wait.

As midnight approached, Cheryl fell into a fast sleep. She did not see her stepfather as he entered her room and approached her bed. He gently sat down and quietly stirred her from her sleep.

“Hey, you awake honey?” he quietly asked his eldest daughter so as not to wake Tawnee who was snoring quietly in the bed above.

“HUH? What’s wrong? Where’s mom?” asked Cheryl.

“Your mom’s where she ALWAYS is – sleeping,” answered Bob.

“Oh, OK” Cheryl was still almost asleep and a bit groggy.

“Be really quiet so we don’t wake your sister, I wanted to talk to you for a minute” said Bob.

“OK.”

“I thought about your report card. I decided not to share it with your mom. I’m just going to sign it and you can turn it back in. But you have to promise me you’ll try harder in math, OK?” asked Bob.

“Thanks!” smiled Cheryl at him. “I really appreciate it.”

“Hey, everyone needs a chance every now and then, right?” asked Bob.

“Yeah, I guess so,” answered Cheryl.

Bob looked at Cheryl again. God she was beautiful. Even in her oversized Tshirt that she was wearing to bed. He could still tell her tits were simply huge under them.

“Boy, I can’t get over how much you are growing up,” said Bob.

“You thinks so?” she smiled at him.

“My goodness yes. Just look at your breasts! They are so large, and they look really good on you.”

“Do you really mean that?” asked Cheryl.

“Hell yeah. Do you think I could look at them?” whispered Bob.

Cheryl hesitated. “But what about mom? You won’t tell her will you?” asked Cheryl.

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