Shy Wendy Ch. 01

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Note to readers: This is my first attempt at writing and sharing a story. Please be honest with your critiques and don’t hesitate to vote!

All characters and names are fictitious. This story is based primarily upon Seniors in High School who are all 18 or older. Any sexual situations described have occurred after the characters reached the age of 18. Wendy has a younger sister who will never be involved in any sexual discussion or situations. She is included for background story depth and development only.


Chapter 1:

Wendy Williams was jolted awake by her phone alarm and quickly reached over to hit the snooze button. Just 10 more minutes would make all the difference she thought to herself. She had stayed awake way too long the night before trying to fit in just one more episode…then another…and finally one more, of her current favorite show, “Arrow” on Netflix. It was an action adventure show that provided an escape from her particularly uneventful 18 year old existence.

It didn’t hurt that Oliver Queen was easy on the eyes. Her thoughts quickly began to wander as she drifted back toward sleep…but in what seemed like 10 seconds instead of 10 minutes, the alarm was going off again. Wendy hit the off button this time and rolled out of bed with a sigh.

Her mind tried to clear the morning cobwebs. Senior year of High School was creeping by and Wendy felt the pressures of adulthood closing in on her. Although, in reality, she had been a defacto adult for all of her teenage years.

Being an extremely shy girl with an overprotective mother had kept her isolated from most of the school activities enjoyed by her friends. The fact that her father had disappeared without a trace when she was only 11 years old had resulted in Wendy taking on a huge amount of the household responsibilities. She rarely had time to spend with her friends outside of school.

Wendy’s mom had been forced to hold down second and, sometimes, third jobs just to make ends meet. Helping to raise her younger sister along with cooking dinners and doing schoolwork had kept Wendy insanely busy for the past 7 years. Her mom never really spoke of her dad’s disappearance, and she had made it clear that the topic was off limits.

Wendy looked into the mirror and saw the bags under her slightly bloodshot brown eyes, and her bed-frizzed shoulder blade length brunette hair. Never being one to pay much attention to her appearance, she was still taken aback by how she looked. It was no wonder that the boys paid no attention to her at school. Plus, it was well known that she wasn’t allowed to date and was hardly ever seen around town after school hours. She might as well be invisible, she thought to herself.

If not for her friend, and fellow 18 year old Senior, Eric who she’d known since 1st grade, she wouldn’t have any interaction with boys at all, Wendy thought to herself (with a hint of bitterness). Eric was like a brother to Wendy. He lived close enough that he had spent untold hours a day in the Williams’ house and yard up until the time of her dad’s disappearance. Wendy and Eric had been inseparable playmates. She treasured those memories. But then, circumstances would change her childhood forever.

There was a knock on the bathroom door. Her younger sister’s voice jolted Wendy back into the present. How long had she been standing there staring at herself in the mirror?

“Hey zombie girl, are you ready yet?” Julie called in. “The bus will be here soon!”

Wendy splashed water on her face, quickly brushed her teeth & hair, and rushed to get ready for school. She just made it down the steps in time. Julie thrust a breakfast bar into her hand as they ran outside to catch the bus.

Other than Eric, Wendy also had one close girlfriend. They were like sisters, but maybe even closer if that was possible. Mary Wilson was already on the bus and Wendy slid onto the seat next to her as she did every morning. Julie headed further back to sit with one of her own friends.

Wendy had met Mary Wilson at the beginning of Middle School when fate found them sitting next to each other in home room. The fact that both girls shared the same exact birthday, and that their last names both started with a “W” seemed to link them in just about everything in school. They tended to share the same classes as well. A bond quickly developed between them. They knew they would become lifelong best friends.

Mary was, in many ways, completely opposite from Wendy. This was one of the main reasons Wendy found her friend to be so interesting. Mary was outgoing, blonde, blue eyed, and while currently unattached, she always had plenty of attention from the boys at school.

“Wow Wendy…you look terrible,” came out of Mary’s mouth before she could think. “I’m sorry…that came out wrong,” she quickly added.

“It’s ok Mary, I agree with you,” Wendy said sleepily. “It Esenyurt escort bayan was a late night binging Arrow,” she added with the best morning smile she could muster.

“I figured,” came Mary’s quick reply with a knowing grin. “Dreaming of taking Laurel’s place with Oliver I’m sure! Well, Felicity might put a wrench into those plans,” she added with a laugh. Mary was also an Arrow fan, but unlike Wendy, she had seen the original airings instead of waiting for the show to get to Netflix.

Wendy gave her friend a soft punch on the shoulder, but her blushing told Mary all she needed to know.

“Hey Wen,” she began…”Senior year is ticking away and you really need to get your mom to let you spend some more time with me! You need some time out of the house to live a little. Maybe we can find ourselves some boyfriends who are worth our time!”

Wendy chuckled, “Not gonna happen. Besides, no boys even look my way…and if they did, I’m so shy I’d go running the opposite direction!”

Mary looked at her best friend and knew she was probably right. How can someone be so shy she wondered. She had always accepted Wendy’s shy personality and never pushed too hard…that’s why they got along so well. But their time together was ticking away, so she decided to press on gently.

“Ya know Wen,” Mary started again…”you are a beautiful girl behind all that stress in your life. With the right pair of jeans, a few stylish tops, and some care to your appearance you’d have plenty of the boys looking your way!”

Wendy rolled her eyes and said “Yeah right…dream on.”

Mary noted the sadness in Wendy’s voice and pressed on. “Please, just ask your mom if you can spend some more time with me since High School will soon be over. Or, maybe she could even let me come over to your place sometime?”

Just then the bus doors opened and in bounced Eric. He quickly found his usual seat just behind Mary and Wendy, putting an end to their conversation.

Eric was also on the shy side, but not to the same extent as Wendy. While not one of the popular jocks in their grade, he did play as a backup linebacker on the football team…just a little shorter and slower than the starters.

Eric was quick to say hello. “Hey Wen…hey Mare…oh geez Wen, did you stay up late again? You look…”

“YEAH I KNOW,” interrupted Wendy.

“I was going to say amazing,” joked Eric, nervously trying to take down the tone.

“Uh huh,” said Wendy with a glare.

“You’ve gotta quit burning the candle at both ends Wen. It’s taking a toll on you for sure,” Eric pointed out.

“No shit Sherlock,” Wendy shot back at him a little more pointed than she intended.

Eric sat back in his seat and the group was quiet for the rest of the ride to school. As they got off the bus Wendy said a quick apology to Eric for her short temper.

“No problem,” Eric said. “I know you’re doing the best you can at home and I shouldn’t poke the bear in the morning. I’m sorry too.” He started to walk into the school but turned back to them. “I’ll see you two at lunch…and by the way, I have a cool surprise to tell you!” Then he turned and headed into the school. Eric did not have any morning classes with Wendy or Mary but the three of them always sat together at lunch.

Mary turned to Wendy and said, “I wonder what that is all about?”

“Good question,” answered Wendy. “Maybe he’s heard back from one of those colleges he applied to?”

The morning classes seemed to drag for Wendy as she paid the price for her late night. She could feel her eye lids drooping as she struggled to keep from dozing off. She turned to look out the window for some type of brain stimulation to wake her up. As she did so, she spotted Mary two rows over leaning back to stretch in her seat. This had the distinct effect of pushing her firm 18 year old 36D chest against her t-shirt. Even with a bra on, her nipples were clearly visible against the fabric.

Just then, Mary glanced in Wendy’s direction and saw her shocked look. With a slight grin she motioned discreetly toward the boy sitting on the other side of her. Wendy looked past her to see Tony sneaking glances at Mary.

Tony was best known as being the oldest boy in their class. Due to being held back a year by his parents before Kindergarten, Tony was already 19. To Wendy’s surprise, she noticed him squirm in his seat and she saw Tony trying to discreetly adjust his jeans. She could see the noticeable bulge which was obviously causing him some discomfort. Wendy blushed and looked back at Mary with an “I can’t believe what I’m seeing” face. Mary grinned. She was obviously enjoying teasing this poor boy who couldn’t control his 19 year old hormones.

The bell rang and the students filed out of the classroom, with Tony waiting until everyone was up and moving before he stood up to leave. Wendy was waiting for Mary in the hallway.

“What the fuck was that all about Mare?!” she asked quickly in a hushed tone.

Mary Escort Etiler giggled as she replied, “I could just feel his eyes on me all during class. I know I shouldn’t have, but it was kind of exciting once I started, and especially once I noticed his…ummm…predicament.”

“Oh my gosh Mare…how could you!!!” Just the thought of something that outrageous made Wendy cringe with nervousness. But secretly, she envied the brashness of her best friend, along with the way the boys’ eyes always seemed to follow her wherever she went. While Mary wasn’t part of the popular girl cliques, she still drew plenty of attention. The girls headed for the cafeteria still giggling and talking about what had happened.

“I’ll bet Tony jerks off tonight thinking about me…if he hasn’t gone to the restroom to do it already,” Mary whispered to Wendy.

Once again, Wendy turned beet red. “Mary Wilson, I can’t believe you just said that!”

Mary just laughed at her best friend’s embarrassment. They went through the cafeteria line and headed for their usual table. Eric was already there waiting.

Seeing their smiles he noted, “You two seem to be in a better mood than this morning…what’s up?”

Mary grinned at the question and said “What’s up indeed!”

Wendy gave a snort laugh and turned red once more. “Just a private joke,” she added.

Quickly changing the topic before Eric could dig some more, Wendy asked him, “So…what’s the exciting news you mentioned this morning?”

“Oh, that,” he said. “Just that my dad is helping me get a car for an early graduation present this weekend,” he tried to say nonchalantly. “Nothing fancy…but still, I’ll have my own set of wheels in a few more days!”

“That’s awesome!” Mary & Wendy both exclaimed unison.

Eric was grinning excitedly now. “You know you are both invited for the first ride,” Eric offered.

Mary said, “Thank you, but I’ll be out of town visiting family this weekend.”

“How about you Wen?” Eric asked again.

“I don’t know…you know my mom. She doesn’t like me going anywhere, even if it is with my brother from another mother.”

Eric smiled and said, “Well, I’d like nothing better than to have my oldest friend, and sister from another mister, take that first drive with me.”

“What about Jake…won’t he feel left out?” Wendy asked. “And where is he, by the way?”

Jake, another player on the football team, was Eric’s best friend who usually sat with them at lunch and who he typically hung out with after school.

“Nah…he has a college visit planned this weekend in California. His family added some days and turned it into a family vacation. So, it’s actually going to be a pretty chill weekend other than picking up my “new” used car,” Eric explained.

“Oh right,” Wendy said. “I remember now.”

They finished eating and, as they filed out of the cafeteria, Wendy caught a glimpse of Tony ahead of them. His “problem” seemed to have gone away as he was walking normally.

Wendy leaned in close to her best friend. “Mary Wilson, behave yourself!” she whispered with a smirk on her face as she gave a slight elbow to her friend’s side.

“Wendy Williams, I do think you are beginning to read my mind,” Mary replied with a laugh.

The rest of the day was uneventful and soon they were on the bus ride home. Eric had stayed behind for football practice. Usually Mary stayed behind for marching band practice, but it had been canceled today due to the director being absent. On the ride home from school, Wendy once again broached the subject of the morning incident.

“You know Mare,” she started, “I really do envy the way the boys look at you. You are so beautiful and there isn’t an ounce of shyness in your nature.”

It was Mary’s turn to blush at the wonderful compliment from her best friend. Then she said, “Wen, I, um,…look, Wendy, I know you’re very self conscious, insecure, and exceedingly shy, but I meant what I said this morning. In all seriousness, YOU are beautiful, but you keep it hidden away. I know it’s partly your mom and partly the overall situation at your house too. The boys at school don’t know what they are missing! Don’t tell me you didn’t feel a little thrill seeing Tony’s jeans bulging in the middle of class!” she whispered in Wendy’s ear.

Wendy blushed a deep red. Mary was always so direct and open with her thoughts and experiences. Wendy loved this about her friend. Despite Wendy’s shyness and embarrassment during conversations of this nature, she could never get enough of hearing about the two boys from their Senior class that Mary had recently dated, however briefly. There wasn’t a TON to talk about from their limited make-out sessions, but anything was more than what Wendy had yet to experience.

Like Wendy, Mary was still a virgin at 18, but she wasn’t shy at all when discussing sexual matters. Mary had gained just a little experience making out, without going any further than she was ready for. She knew she Eyüp escort was pretty and she had become used to the way the boys looked at her. The effect her body had on the boys in their class made her feel powerful and confident. Mary wasn’t dead set against losing her virginity, but she wasn’t going to give it up to just anyone is what she had told Wendy. In fact, this had led to the quick break-ups with both boys. They had both tried to push her for more, but neither seemed interested at all with Mary’s needs at the time.

Wendy, on the other hand, was shy to the core and terrified of drawing any attention to herself…especially attention from boys. But that didn’t mean she didn’t have urges. She occasionally read her mom’s romance novels while mostly looking for the sex parts. She would sneak peaks at porn when she was locked safely in her bedroom. She had hung on every word when Mary filled her in about her recent dates. In essence, Wendy was full of hormones like the rest of her classmates, but kept it all hidden…even from Mary to a certain extent.

“Yes Mary, I admit I felt a thrill seeing his bulge in the middle of class!” Wendy confessed in a hushed tone, while blushing yet again. “Are you happy now?”

They both broke down in girlish giggles. The bus stopped and Wendy headed for her house giving a quick wave to Mary as the bus pulled away.

Wendy’s mom was working another late shift and wouldn’t be home until early morning. Wendy was happy to find a note from her along with dinner waiting for the two sisters in a crock pot.

That night, after all her housework and schoolwork was finished, Wendy said her goodnights to her sister. Then she headed for her own bedroom where she locked the door and changed into her nightshirt. Her thoughts returned to the earlier excitement at school.

Wendy sat on the edge of her bed and turned on the next episode of Arrow. As luck would have it, the episode included a particularly hot encounter between Oliver and Laurel’s sister Sara. Oliver gets whoever he wants, whenever he wants she thought to herself…just like Mary could probably do. She began to watch the love scene intently. The sexual tension on screen started to have an affect on her, and she felt that yearning feeling building in her core.

Wendy let her hands trace down over her nightshirt. Her nipples had hardened and she remembered how Mary had looked while stretching in class. A glance downward allowed her to admire the bumps now showing through the soft cotton…especially with no bra constraining them. Wendy let her hands gently run over her breasts once more, sending jolts of pleasure through her. Her 36B’s felt soft and full to the touch and her nipples were rock hard and straining at the fabric.

Maybe Mary was right she thought to herself…a glance at her full length wall mirror allowed her to see the beauty that she kept hidden away behind her baggy clothing and devil may care attitude toward her looks. Wendy could see her wavy brown hair cascading to just below her shoulders. The way it framed her pretty face, accentuating her brown eyes, and full lips. Was she wrong in thinking she looked a bit like Laurel on Arrow?..she wondered. Her eyes finished scanning downward across her 5’5″ slim frame…her bare legs visible below the edge of her nightshirt.

She closed her eyes, feeling the sexual urges flowing through her. I wonder what Tony would think of MY nipples pressing at my shirt she thought. A boy she barely knew was making his way into her fantasy. Would her nipples make Tony hard like Mary’s teasing nipples had? The memory of his bulging jeans returned. Wendy’s thoughts began to swirl fast and uncontrolled in her mind.

What would it feel like if I could touch his bulge? What if I unzipped him? What would his cock look like? How big or thick is it? Did he go home and jerk off like Mary suspected?…or maybe even jerk off in the boys restroom at school?

Wendy felt the fire burning between her thighs. In her mind she pictured Tony unzipping his jeans to release the hardness Mary had caused. Wendy let her right hand drift lower until it slipped beneath her panties…slowly running through the soft patch of neatly trimmed brown hair. She quivered as her fingers found their target. Her panties were damp and her slit was slick with wetness. She couldn’t remember ever being this wet before. Her fingers moved along her slit and dipped into her hot, aching pussy. The sensation was electric. Her jaw dropped open as a gasp escaped her lips.

Her eyes opened again and Wendy looked at herself in the mirror…watching her hand motion. The sounds coming from the TV caughat her attention. Oliver’s bare chest was glistening with sweat as Sara lowered herself down onto his waist. “Why are the sheets always in the way? I want to see them joined. I want to see ALL of him! Oh, to be riding Oliver Queen!” she thought, as the low sounds of sex continued to emanate from the TV.

Wendy’s well lubricated fingers continued moving in slow, rhythmic circles over her clit. She watched as Sara began to move her hips and arch her back while Oliver held her in his strong grip. Again she pictured Tony’s bulging jeans…Wendy longed to be on top of something. Turning in her bed she found her pillows and quickly stacked them beneath her.

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