The Cheryl Cummings Story: Early Years

** The New Boy **

Cheryl yawned, stretched, and moved her feet to the floor, rising out of bed on a brisk and slightly cool late April morning. The Florida sun shone brightly into her bedroom. Cheryl and her younger Sister Tawnee lived in a three-bedroom apartment with their mother since their father had been killed in a bizarre and tragic plain crash 9 years ago. At 19, Cheryl was old enough to still remember and miss her father, but at 18, Tawnee wasn't much more than 4 at the time of their fathers passing. So it was harder for Cheryl.

Cheryl's mom Jane had loved the girls' father very much and mourned a great deal for him after he had died. She had simply refused to date for years following the ordeal. It was only in the last couple years that she had even considered going out again, despite all of her friends and family's encouragement. And it wasn't that there weren't a great deal of interest. Cheryl's mom was a very pretty, well built, young blonde woman who never failed to turn heads whenever she dressed up and went out.

Despite the interest in her, she politely declined any offers that came her way. She preferred, instead, to remain home with her girls and give the healing process a chance to work.

However, for Cheryl, today was a day filled with promise and hope. After Cheryl's dad had died, their family had to downsize quite a bit. After selling the house, cashing in insurance, and paying off all the bills, there had not been a great deal of money left over, so they had to adjust their lifestyles to a more modest and scaled back lifestyle. This was sometimes difficult for both Cheryl and her mother Jane to deal with. They moved to a small apartment, which meant that Cheryl had to get used to an entirely new school.

The adjustment had been difficult, and making friends was a slow process, in spite of the fact that Cheryl was a very pretty and outgoing girl. At nineteen she was blossoming into a beautiful young woman. She had sprouted to a height of about 5'3" tall, and her breasts seemed to develop overnight. Her mom would tease her that they could now share bras, since they both healthy 34 Cs. Cheryl would likely eventually end up passing her mom in this category, since her breasts had developed to C cups upon turning 15, and certainly the girl was not done growing yet!

The hope that Cheryl woke up feeling today though was based on a surprising and wonderful turn of events that rounded out the previous week. School had been going just like any other year, nothing really exciting. However, a couple of weeks ago something wonderful happened, simply by chance. A new kid in school had been sat directly in front of Cheryl in her Algebra II class. (God, he was cute). His name was Chris. He was about 5'10, smallish guy, with dark hair and glasses. Cheryl thought he was the cutest guy she had ever seen in her life. Shortly after class began, he turned around and talked to her.

"Hi, my name is Chris. What's yours?" asked the young man in front of her.

"I'm Cheryl, pleased to meet you. How do you like Tampa so far?"

"It's OK. We're just trying to get used to the new town"

Cheryl could definitely relate to adjustments. She had certainly had to make enough of her own over recent years. And so it started. Chris and Cheryl got along fabulously from the very beginning. They became immediate friends, and it seemed that their relationship might go somewhere beyond a casual friendship.

The school days passed as any other as the year wound it's way to a close. The one thing that was looming over the high school kids was the fact that the prom was on it's way. Up until meeting Chris, Cheryl hadn't given prom a second thought. She was a sophomore, so she didn't really necessarily think she would even be going to prom -- unless someone were to ask her. However, with her new relationship forming with Chris, Cheryl couldn't help but wonder...

Chris didn't make her wonder for very long. Today he had asked her to accompany him to the PROM!! It was like a dream. Cheryl had been walking on air every since. She simply couldn't wait to pick out her prom dress. She was a little worried, because she knew her mom was on a budget, and was not entirely convinced that they would even be able to afford to buy her a dress for the prom!

** Picking out a Prom Dress **

Spring came early that year. The sun was shining bright on that beautiful spring day, ensuring that summer was just around the corner. Summer was definitely Cheryl's favorite season. The young blonde simply loved to be outside in the sun working on her tan. Every year she layed out as much as she could and was always a lovely dark bronze.

Cheryl was definitely an outdoor girl. She loved to lay out, run, play tennis, she even could be found hanging out with the boys some nights playing on skateboards. She was somewhat proud of the fact that she could do as many tricks as any of the boys and more than some.

Cheryl had definitely grown up as a bit of a Tomboy. In fact, most of her 'boy friends' thought of her as one of the guys. She wasn't uptight and squirrelly like many girls. She was more like one of the guys. That is, until recently -- when she seemed to grow into a young woman practically overnight. This didn't really seem to phase the boys though. They still treated her as one of their own.

With summer just around the corner, on a bright clear Saturday morning, Cheryl set out to begin shopping for the dress she would wear to her first prom. She refused to feel the least bit sad about the fact that her mom wouldn't be able to come along with her this morning. She was going to, but then her mom's boss had called last night to inform her that she would need to come into work this morning due to an emergency in a co-workers family.

"You're welcome to wait until next week for me to come with you," said Jane to her daughter.

"It's OK mom, I can go out looking on my own tomorrow. I'm sure it'll take more than one trip to decide anyway!"

"True. Just remember, we ARE on a budget -- so we can really only afford $75 - $100."

"I know, I know," said Cheryl.

Cheryl stood in the window, looking up in awe. The dress was simply amazing. She knew, in an instant, that it would be perfect for her. Then she looked down at the price $375!!

"Ummm...look again," said Cheryl to herself as she opened the door, walking into the store.

The store was a small and simple store. Behind the counter stood a happy and safe looking large middle aged Italian man. Cheryl half suspected that it was his wife that owned this store and that he was helping her out on a Saturday morning. Cheryl was immediately struck by the store and convinced herself that she would like to buy her dress from these small store owners.

"Good morning," beamed the large Italian man from behind the register. "How can I be of service to you today?"

The pretty blonde inched her way into the store, suddenly feeling a bit timid. "I have to find a dress to wear to my prom."

"Oh, a lucky young man is taking you to prom this year, huh?" smiled the man.

"Yeah."

"Well, I have the absolute perfect dress -- one I KNOW you will want -- but we're going to have to figure out if you are the right size for this style of dress."

"That would be wonderful. I do have a budget I have to stay within too," said Cheryl as the large man opened an armoire behind him, pulling out the most perfect dress Cheryl had ever seen. She suddenly felt like Cinderella in the presence of her fairy godmother. However, in this case, her fairy godmother was a large, pudgy, middle aged Italian gentleman. He did seem almost majestic though. He somewhat reminded Cheryl of a big Italian Burl Ives kind of guy.

"Oh that looks so perfect! How much is it?" inquired Cheryl.

"First things first. You can call me Mr. Barwell. Before we start talking money, let's get your measurements and we'll select a style of dress from there. If possible, this one seemed perfect to ME for you. Keep in mind, we've been in this business for more than 40 years, and I'm rarely ever wrong!" said Mr. Barwell as he reached behind the counter, grabbing his tape measure. "Here it is!"

"OK. My name is Cheryl."

Cheryl couldn't explain why, but she felt so comfortable with this gentleman. He was wearing a white T-shirt, and a pair of denim slacks. Even though he was older, with graying hair, he was still an extremely large man, standing around 6'4" tall. But due to his calm and endearing countenance, it was as if he was her grandfather or something. He had a broad, flat nose, formidable lips, warm brown eyes, and a close cropped short hairstyle. When he gave her instructions, she just felt that she SHOULD listen to him. So, they walked behind the counter and he led her back into the changing room, closing the door behind them.

"What's your boyfriend's name?" asked Mr. Barwell as they walked into the changing room together.

"Well, his name is Chris. But he's not my boyfriend....at least not yet," she beamed.

Mr. Barwell winked at her, as if they were sharing a choice secret. Cheryl felt so at ease with this new gentleman. It was really unusual for her to take to someone this quickly. Normally Cheryl was always very shy and reserved. She just felt completely comfortable with the big Mr. Barwell.

Mr. Barwell stood facing Cheryl. "We're going to need to get very good measurements so that the dress you select will be the absolute perfect one for you!"

Suddenly Cheryl felt a little bashful again. "I've already taken my measurements at home though. I know what they are." She offered feebly.

"Oh honey, we have to get EXACT measurements. Only my wife is better at taking them than me. I am VERY good at sizing. We need a perfect fit."

At that, Mr Barwell put his hands on her shoulders, spinning her around. Mr. Barwell was obviously accustomed to giving instructions and having people follow his instructions. Cheryl felt his hands slide down from her shoulders. He grabbed each of her arms, lifting them straight out at her side. He let go, indicating that she continue to hold her arms out. As she did this, he reached around from behind her and began to unbutton the buttons to her shirt.

"We'll have to get some without the shirt my dear," said the large Italian man, as his hands quickly unbuttoned each of her shirt buttons.

Before Cheryl could really even think about it, she felt Mr. Barwell grab her shirt, pulling it off of her shoulders. Cheryl's face immediately went beat red from blushing. She had never had a grown man see her even in her bra. She had a white pushup wonderbra on that pushed her large breasts up, making them appear even larger than they already were.

Cheryl couldn't understand why, but when she looked down, she could clearly see her nipples poking through her bra. It wasn't cold in here, so she had no idea why her nipples would do that, but it only increased her embarrassment.

As if this weren't enough, as she stood there looking down at her nipples, suddenly Mr. Barwells hands slid under her arms and his big meaty hands cupped her large breasts through her bra, feeling their weight.

"My goodness dear, you have very large breasts! Are they real, or did you get false ones?" asked Mr. Barwell as nonchalantly as if he were asking her about the weather.

"Ummm...yes sir. They are very real," offered Cheryl, still feeling embarrassed, but at the same time feeling a glint of pride shining through as this grown man complimented her on her tits. For the most part, Cheryl often went through great lengths to HIDE her large breasts, being very embarrassed by her recent development.

"You don't say," said Mr. Barwell. "It's unusual for someone with such a small frame, such as yours, to have such large and perfect breasts," he said as he continued to gently lift her breasts in each of his hands, as if he were weighing them with his hands.

Cheryl couldn't suppress a smile as a result of Mr. Barwells words. As he talked to her, she found herself totally relaxing, and the fact that he was openly feeling her tits from behind didn't even matter to her. She just assumed that this was all part of the 'measurements' he was taking.

Sensing his words were working, Mr. Barwell removed his hands from Cheryl's big tits, reached around, and quickly unclasped her bra from behind.

"OH! What are you doing Mr. Barwell?" inquired Cheryl, as she felt the bra loosen from around her tits.

As the bra opened behind the young girl, Mr. Barwell grabbed each side, pulling it away from the girls large tits, fully exposing them in the mirror in front of him.

"My dear you will have to trust me. It is necessary for me to get a good measurement. I can't do that with all this clothing in the way, now can I?" as he spoke, he was grabbing the snap on her jeans. Cheryl looked down, as if in daze as her pants opened and the zipper slid down.

"If you don't trust me, maybe we should wait until my wife can do this for you? The only thing to consider -- I REALLY want to get you the right dress, and I'm FAR more willing to negotiate price -- to make the right fit. My wife is much less willing. She is a tougher negotiator than me!"

Cheryl considered the power of Mr. Barwell's last statement. Especially considering the fact that she was on an extremely limited budget. She also could simply sense that Mr. Barwell would find a way to get her into the dress of her dreams, regardless of price. He was such a nice man, and his voice was almost hypnotic to the teen.

"OK. I trust you, Mr. Barwell!" said Cheryl, smiling up at him.

Mr. Barwell smiled down at the hot little thing in front of him. He didn't doubt that she WAS starting to trust him. This notion excited him to a point where he was afraid he might have to HIDE how much this excited him. He had to be careful. He couldn't move as fast as he would certainly like to.

Mr. Barwell grabbed Cheryl's jeans on each side of her hips. He firmed his grasp and pulled. Her jeans were so tight, as he pulled down, Cheryl's panties slid down her body with them, revealing her lightly trimmed blonde bush. Again, Cheryl turned crimson red with embarrassment. She couldn't believe she was letting this man completely undress her.

Mr. Barwell pulled both her pants and panties down her legs to her feet, helping the girl step out of them. Cheryl now stood before the giant Italian man completely naked.

"Absolutely lovely," beamed Mr. Barwell, smiling down at Cheryl.

His smile was absolutely contagious, and put Cheryl completely at ease again. She could not understand how she could feel so comfortable -- being so completely naked -- in the presence of a male stranger. An Italian, adult stranger at that! But something about Mr. Barwell just put the girl completely at ease. She simply accepted that he was a professional, simply doing his job.

"OK Cheryl, now I need you to bend over and grab your toes for me," said Mr. Barwell. As she complied, he stood behind her and measured her ass with his tape measure. Of course, to do this, his hands were pretty much all over her small, tight, perfectly rounded young ass. Mr. Barwell worked slowly and deliberately, running his left hand all over the girls tight butt cheeks. Even though his hands were all over her, Cheryl never protested in the slightest. She was completely at ease with Mr. Barwell. He could feel his cock completely hardening as he touched the girls tight ass.

Next, Mr. Barwell moved around to the front of Cheryl and began pulling her up. As she was lifting up, she suddenly found herself looking at Mr. Barwell's crotch. At first, she wasn't sure what she was looking at, so Cheryl frowned as she saw the penis shaped bulge. As she stared, she suddenly realized what it must be that she was looking at. It had to be Mr. Barwell's penis that she was seeing bulge through his pants. What was more, from what she could make out through the pants, it had to be bigger than anything the young blonde had ever seen! Not only that, as she stared dumbfoundedly, the head seemed to travel down even further-- down his right pants leg.

Cheryl was surprised at herself by the fact that she suddenly felt very curious about the bulge under his pants. What in the world could that thing possibly look like, she couldn't help wondering. She had seen penis's in health class, but never one that was completely hard.

"OK, let me run out and select a couple dresses for you to try on," said Mr. Barwell, interrupting Cheryl's thoughts.

Mr. Barwell disappeared out of the changing room, leaving the naked young girl panting as her imagination seemed to be playing tricks on her. Now that he was gone, she convinced herself that there was no way that had been his penis she was seeing.

It must have simply been his pants bunched up in some funny way. As she glanced over into the mirrors that surrounded her in the changing room, she could see her pink little nipples were sticking straight out, and were hard as little pebbles.

She reached up and gently touched each one with her two hands. She gently tapped her nipples with the index fingers from each hand, marveling at just how hard and pointed they were. She had no idea why, but suddenly her pussy felt a little funny...almost as if it were turning moist.

As Cheryl was testing the hardness of her nipples, the door suddenly popped back open and in strode Mr. Barwell, catching her examining her nipples.

"Hmmm...they DO poke out considerably, don't they?" asked Mr. Barwell, again causing Cheryl to blush. He acted as if he had discovered a serious problem though, and walked right up to her, looking directly at her hard young nipples. He hung several beautiful dresses on the hanger behind her, then gently reached up his hands, deftly massaging her nipples in a circular fashion.

"We may have to look for something special for these, or they might be showing all night on prom night," smiled Mr. Barwell at the teen, as he gently and expertly massaged the girls sensitive nipples.

"MMMM...," Moaned Cheryl as his fingers sent electricity through her breasts, that seemed to just shoot directly down to her already moist vagina.

"I guess they are very sensitive, huh?" asked Mr. Barwell, as if diagnosing a significant medical condition in the youth.

"I guess so. I had no idea they were like that though," answer Cheryl, completely honestly.

"Well, we may have to do a few tests to see the best way to handle that," answered Mr. Barwell, as he continued to gently caress the young girls rock hard nipples. He simply could not believe how easy this had been.

Suddenly he pulled back, and grabbed a dress that he had hung directly behind Cheryl.

"Let's begin with this one. I believe this will be the one you will definitely want," said Mr. Barwell with confidence.

As he held it up, Cheryl couldn't help but let out an audible gasp. What he held had to be the dress of young Cheryl's dreams. She instantly knew that her feelings about Mr. Barwell were right on. He KNEW what he was doing, and he was going to get her exactly what she wanted!

Then the whole budget thing came back to her. She almost started to cry when she thought of it. Looking down, she asked "But how much does this dress cost?"

"This is a very reasonably priced dress honey. It's only $250," replied Mr. Barwell.

With that, Cheryl felt a teardrop slide down her cheek. "We better pick a different one sir, I only have around $100 to spend today."

"Listen, the first thing to do is figure out if this dress is right for you my dear. If it is, and you look perfect in it, then you and I will work out a way for you to be able to afford the dress. OK? You just leave it to me, we will find a way," reassured Mr. Barwell.

"OK," answered Cheryl, regaining some hope.

With that, and without even putting on any underwear, Mr. Barwell, began helping Cheryl into the dress. She leaned on his large shoulder as she stepped into it, then he gently lifted it up her body. When it was about half way up her hips, Mr. Barwell spun her away from him, so that she was again facing away from him, looking at herself in the morror.