Cedar Hill Cheerleaders Ch. 05

Story Info
It’s all about Skye and Greg’s first time.
3.4k words
4.5
20.5k
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Part 5 of the 16 part series

Updated 06/13/2023
Created 11/02/2016
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Greg Arden was one of the Audio/Video geeks at Cedar Hill high school. He was a class-mate of Jamie Taylor.

Skye McDougal was one of the Cedar Hill high school cheerleaders. She worked at her local Wal-Mart every Saturday morning as a checkout chick.

Quite often school friends would use the Wal-Mart store. Greg seemed to shop there more often than most. He always went through Skye's checkout, and because of this she thought he had a crush on her.

Skye liked Greg, but she was afraid to encourage him, because she was afraid of what he would think about her 'curtains'. Her labia minora were about 3 inches long when hanging free rather than being tucked into her cunt.

***

Skye's shift at Wal-Mart started at 8am and ended at 12noon, with a tea break at about 10am.

Most times she enjoyed her shift. However there were those times when a customer would criticise her for putting the wrong things together in the plastic bags, or claim she had given them the wrong change. On these days having Greg come through her checkout was often enough to cheer her up.

Greg normally stopped at about 11:45am to buy a stick of gum or a sports drink on his way to tennis. He always had a smile for Skye. Most days he would simply say, "Hi Sky; you look radiant as usual... Please wish me good luck at tennis."

If he sensed she'd had a bad day, he would make an extra effort to lift her spirits. The line he most often used was, "You really making that uniform look extra special today; I hope you put the effort in for me. You're not seeing someone else are you? That would break my heart, you know."

Skye knew that Greg was a nerd; that is he was intelligent, and that was part of what she loved about him. So she was willing to accept his horrible pickup lines, and was cheered up by the mere fact that he tried.

***

Saturday morning two weeks ago Greg was trying to decide what to wear. Would he wear his usual tennis outfit, or should her just put it in his car and wear his clothes that most closely matched the Wal-Mart male shop-assistant uniform. He decided to go with the latter and wear a white shirt, black tailored trousers and a royal blue vest.

So at 9:30am Greg reported to the Customers' help desk at Wal-Mart. He had seen an advertisement for shop assistants, and when he phoned he was given this appointment.

"Please follow me." The shop assistant instructed as she took his resume.

Greg was shown into the manager's office. "Mr Everett, this is Greg Arden... Here's his resume."

"Good morning Greg."

"Good morning, Sir."

"I see you are aware that we like our staff to wear a uniform."

"Yes Sir."

Mr Everett read Greg's resume for a few minutes.

"Now why do you want to work for us?"

"Well I think I need some work experience before I go to University, and it will help on my resume."

"Are you applying for a University scholarship?"

"Yes Sir."

"Which University would you like to attend?"

"The Jefferson University at Linterna."

"So if you go there will you still be living in this area?"

"Yes Sir, with my parents."

"And what course do you intend studying at University? I see here that you are currently doing audio/visual at Cedar Hill High School."

"I hope to study electronics with audio/visual as my major."

"I guess audio/visual requires a great deal of attention to detail."

"Yes and exact timing."

"Do you know any of our current staff?"

"Yes, I recognised some of the boys as students from my school, but I don't know any of them personally. I also know that Skye goes to my school."

"Skye the check-out girl?"

"Yes Sir, but I don't think she knows me by name. She probably would recognise my picture though, because I shop here quite often."

"You don't mind if I ask her, do you?"

"No Sir."

"Do you play any team sports?" With this question Mr Everett wanted to find out if Greg worked well with other people.

"I play mixed doubles tennis in the local Saturday afternoon competition. That's why I have applied to work early on Saturday mornings."

Mr Everett was pleased with this answer, because Greg had shown a good attitude toward time management. "Oh OK. Are you any good?"

"We came second in division two last comp. Right now we are about the middle of division one."

"And how many divisions are there?"

"There are fourteen divisions; the bottom few are beginners, generally ten to twelve year olds. The top few divisions are mostly sixteen to eighteen year olds."

"How long do you play for?"

"We play from 12 noon up to 4pm at the latest, but I'm only on the court for half that time."

"I hope you wear sun screen?"

"Yes Sir."

"What other medication do you carry in you tennis bag?" Greg didn't know it, but Mr Everett was trying to ascertain how much Greg had thought about safety.

"I have some liniment; a tube of Manuka antiseptic cream, and some band aids."

"Good. Well I think that will be all. We'll let you know the result next week."

"Thank you Sir."

When the Manager finished interviewing all the applicants, he looked for Skye.

He found her in the lunch room on her break.

"Good morning Skye."

"Good morning Sir."

"Do you know a boy called Greg Arden?"

"Sorry no Sir."

He showed Greg's picture to Skye. "Do you recognise this boy?"

"Yes Sir. He shops nearly every Saturday."

"He's applied to work here. What do you think?"

"Well he goes to the same high school as me. He is one of the nerds; sorry I mean he is one of the more intelligent boys in our year. Is he the Greg you asked about?"

"Yes, he is Greg Arden... Thanks Skye; I won't disturb you anymore."

"Thank you." Skye thought, 'So that's your name, Greg Arden.' She smiled as she returned to her cup of coffee.

***

Last Saturday, as Skye was leaving the lunch room to start her shift, Greg walked in wearing the Wal-Mart uniform.

Skye spoke first, "Hi Greg. So you got a job here then?"

"Yeah; I started working here today."

Greg had received a phone call on the previous Thursday that he had been selected.

"What job did you get?"

"I'm to re-stock shelves; so today I've been told to learn where everything is."

"So why are you in here now?"

"I work the early Saturday shift from 6am to 10am, with a tea break about 8am."

Skye considered that. "Oh, so you finish work when I'm on my morning tea break."

"Yeah, guess so."

"Well I have to go and start my shift now. See ya later."

From that day on, most Saturday mornings played out much the same.

Whenever Greg was re-stocking a shelf from where he could see Skye, he often glanced in her direction, but quickly looked away if he thought she was going to catch him. Obviously she sometimes looked his way just in time to see him turn away.

Between customers Skye turned her head and scanned the isles for Greg. If he was where she could see him working, she would spend a moment looking at him and daydreaming; wishing her would make a move and ask her out. Greg often caught her staring his way with a far-away look in her eyes.

If Skye needed a price check on anything, no matter what it was, she always called out over the store PA, "Greg! Price check required by register 3 for xxx 1 kg pack; thank you!"

If the item was close enough, Greg walked to Skye's register and told her the price; otherwise he reluctantly used the PA to tell her.

***

One day at the end of his shift, Greg barged into unisex toilet only to see Skye sitting there with her knees spread and her hand between her massive inner lips. Her khaki slacks and pink panty were around her ankles.

The ladies Wal-Mart uniform consisted of khaki slacks, a white long sleeve blouse with a royal blue vest.

Greg was startled by the sight. Other than Skye's instinctive reaction to immediately clamp her legs together, she froze like a deer in headlights.

The door's spring caused it to swing closed behind Greg.

To regain his composer, Greg shook his head; and then apologised, "Geez, I'm sorry Skye. I didn't know anyone was in here."

Skye recovered, "No, it's my fault for not latching the door."

Greg pleaded "You won't report me to the manager, will you?"

"Nah... Will you please forget what you saw?"

Greg said "All I can see is a beautiful girl caught in an awkward situation, and I still think it's my fault."

Even though Skye had short hair, she pushed it behind her ear with her fingers.

As the conversation progressed, Skye gradually relaxed and allowed her legs to drift apart just a little.

Greg did not stare at her pussy, but continued to look into her eyes.

"Oh shit, I'm sorry. I just realised, you didn't come here to perve at me; I guess you need to do a pee. I should go so you can."

"It doesn't matter now."

"What do you mean, now?"

"Well seeing you like this has given me a massive hard-on."

"So?" Skye glanced down at his pants and saw the bulge.

"So a guy can't pee when he has an erection." Skye was pleased that he was aroused rather than being put off by the sight of her pussy.

"Oh! So since I caused the problem, I guess it's up to me to do something about it. Lock the door." Greg did as instructed.

Skye sought reassurance. "Now we are agreed, aren't we; that this never happened?"

"Oh yeah, for sure."

She reached out and began to undo his belt.

"What the fu..."

Skye put a finger to her mouth, "Sssh!"

Skye remembered how she had sucked Jamie's cock under the cafeteria table.

She undid his zipper and tried to pull his erection free. She had great difficulty doing this. When she finally extracted it from his underpants, she discovered why. Greg had his own secret; his cock was enormous, not unusually long at about seven inches, but very fat. Even though she had long delicate fingers, they were unable to completely encircle his manhood. His cock was at least two inches across.

As she took it in her hand, she looked up into his eyes. Her face glowed and there were love lights in her eyes.

Skye lent forward and wiggled the tip of her tongue around the top of his cock; paying particular attention to its hole. She received her first taste of his pre-cum; it was very similar to that of Jamie's.

Again she looked up at him, "Am I doing it right?" She wanted so badly to please him.

"Yeah. You can also try sucking on it like it was an iceblock. But be careful not to rub it with your teeth though."

Initially she put only the head into her mouth. Greg felt the warmth of Skye's mouth as it enveloped the head of his penis. She ran her tongue over it as she sucked. The sensation this gave Greg caused the muscle at the base of his cock to retract briefly and the entire length of his cock pulled back a little.

After a bit she slid her mouth further down and sucked harder as she pulled back off. She repeated this action a few times before asking, "You mean like that?"

"Ooh shit yeah... Now rub your hand up and down while you suck the tip."

With her feminine fingers wrapped around the shaft, she pumped up and down even while she licked the head.

She stopped licking just long enough to ask "Like that?"

"Yeah, keep doing that."

When she resumed, Greg couldn't help mutter "Mmmmm... It feels great."

While Skye stroked and sucked his rock-hard penis, she caught him glancing down at her naked legs and pussy.

She stepped out of her slacks and panty and then spread her legs wide to make sure he could see all of her magnificent inner lips, her 'curtains' as she called them. She felt his cock twitch and swell even more if that was possible.

Her hand moved gently up and down his shaft. She didn't seem to be in any hurry, and he wasn't going to complain about her taking her time.

Skye returned to sucking up and down on his erection. This time her hand lightly caressed his balls.

"Please don't squeeze my balls any harder; there're easily hurt, you know?"

He was receiving indescribable pleasure from the mouth, lips and tongue of this beautiful semi-naked girl. His swollen penis ached, seemingly ready to explode at any moment.

Skye's arousal was so great, she felt it was the right time to become a woman; to give herself completely to this boy and let him take her as a man. But first she wanted him to go down on her; for her to feel his nose nuzzle in her pussy, between her inner lips. To experience again the feeling Jamie had given her, but this time she wanted it to last much longer.

Skye rose to her feet and kissed Greg. She put her tongue between his lips for him to suck.

With her hands she guided his cock between her legs, taking care to place her 'curtains' either side of it. She brought her legs together just enough to hold his manhood lightly. Its head was near her arse and the shaft pressed against her clit.

Skye rocked her hips slowly back and forth, massaging the entire length of his enormous erection. Her pendulous labia tickled his balls each time she moved hard against him.

He was tempted to pull back and aim his cock at her pussy, but he didn't want to rush her. Anyway he had never experienced anything like this before. He thought, 'Being inside her pussy couldn't be any better than this.'

Eventually she put her mouth near his ear and whispered, "Greg, I want you to go down on me; I want you to suck my pussy, please... Just sit on the seat and I'll straddle you; please."

Greg did not hesitate; in no time at all he was seated and Skye turned and shuffled toward him. The sight of her labia hanging there was extraordinary. His cock stood even more upright, eager to slide between those luscious lips and into her cunt.

Finally she had one leg either side of Greg and her pussy pressed against his face.

"Please suck my lips."

Greg gladly did as she asked; first he drew the left labia into his mouth and massaged it with his tongue as he sucked gently. It was silky soft. Then he repeated the process with the right lip.

His nose pushed against her clitoral hood as he toyed with her labia. Then he diverted his attention to the rest of her cunt; he pushed his tongue between her 'curtains' which lay across his cheeks.

Greg pulled the skin above her slit up so that her clit was exposed. And then he tilted his head back so he could suck on it. It was smooth and firm; the size of a pea.

As Greg massaged her clit with his tongue, he pushed his middle finger into her cunt and searched for her G-spot. When he found it Skye let out a shriek of pleasure.

Realising he had found the G-spot, Greg wiggled his finger over that position as he continued to give a love bite to her clit.

"Ooooh God that's nice! ... Mmmmm." She moaned.

Greg was please that he was giving her such pleasure; it encouraged him to continue.

Eventually Skye decided to give him the ultimate reward for his patient oral sex.

"Mmmmm... I'm ready now Greg... Oooooo." And with that Skye lowered herself onto Greg's prick.

She was so aroused and well lubricated that even his huge erection slid in easily. She felt it rise up within her, stretching her as it went. It was much nicer than even her biggest vibrator, because it was warm and was attached to a handsome guy.

Skye kissed Greg passionately as she bounced up and down. All she seemed to be interested in was riding him until he came within her. Even so his penetration was giving her immense pleasure.

Greg was amazed by the slurping and gurgling sounds created by the movement of his cock within her dripping wet cunt. Sometimes it sounded like water siphoning down a drain.

He was very much aware of Skye's warm pussy squeezing his throbbing erection.

He felt himself getting closer and closer to climaxing. He clutched her hips and pushed against her pelvis; thrusting as deep into her as he could.

Soon Greg erupted inside Skye. "Aaaah!" His penis pulsed again and again. She leant against him; her hair tickled his nose and cheek.

Greg remarked, "You know this is like joining 'the mile high club', but without the expensive aeroplane ticket."

Skye smiled, "Yeah." This was the first time she had allowed anyone to come inside her.

For several minutes Skye remained on his lap, hugging him. He had his arms around her. The right side of his chin pressed against her hair. He could feel her long breaths as she seemed to melt against him.

God, it felt right. He loved the feel of her against him, and the musky scent that wafted from her pussy. He loved knowing that she felt him inside her, filling her; that they were so intimately joined in the best way possible.

It felt so good he thought he must have died and gone to heaven.

He wanted to whisper in her ear 'Let's stay like this forever', but her phone beeped three times. "Dam it!" she exclaimed.

"What was that?" Greg asked.

"My phone telling me it's the end of my tea break."

"Bugger!" Greg exclaimed.

Skye lifted herself off his shrinking dick and began to get dressed while facing him.

Greg watched as she folded her right labia inward and then pressed the end of it into her cunt. She repeated the process with the left. She smiled at Greg as she licked her fingers. "I can taste your sperm."

She retrieved her panty from the floor. Greg watched as she pulled them up her legs and hid that glorious pussy. Next was her slacks. This reverse striptease caused Greg's cock to firm up again.

Skye tapped his cock with two of her fingers and laughed. "Can we do it again next week?"

Greg immediately replied, "Yeah, you bet. I'm looking forward to it."

"Next time can we take all our clothes off?"

"Sure, why not?"

Skye bent over and briefly licked his penis; rose and kissed him on the cheek. And then she was gone.

Greg forced himself to think about lunch and tennis. It worked; soon his penis was limp enough for him to finally do that piss.

Greg remembered that the store had a women's fashion section. There he found what he wanted; a broach of a Papilio butterfly. They are the ones with wings which are longer than those of a normal butterfly; their wings extend at the back. He believed that the broach he chose was a stylised version of Papilio Blumei from the Celebes, because it was lead grey and sky blue in colour. Greg hoped Skye would realise the significance of the longer than normal wings.

When Skye saw Greg in her checkout queue, her mind turned to things sexual. She thought about his spunk frantically swimming up within her, looking for an egg that wasn't there; it was a safe part of her monthly cycle. She also became aware of the dampness forming in the crotch of her panty; this was caused by his cum that had lost its fight with gravity.

When Greg reached her register, he gave the butterfly pin to Skye. The ladies in the queue all sighed. One adding, "Oooh aint that sweet."

Skye may have blushed, but she was extremely happy and her whole face lit up with a smile.

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Wayne_RichardsonWayne_Richardsonalmost 5 years agoAuthor
Yes

I'm well fitted out myself (9 inches long, just over 2 inches fat); so yes, I relate to Greg in this story and to Jason in Chapter 7.

smuuthiesmuuthieover 5 years ago
Unusual sex parts

I give you props for including some people with unusual sex parts, did you have an incident like that?

AnonymousAnonymousover 7 years ago
Good, but needs a bit more

This story was pretty well written, and it really did turn me on. I think you should just add a bit more detail into it to make it even better. Describe the character's faces a bit more, and also describe what they're doing to each other better. Other than that, I think the concept was really great. Hope you keep writing! :)

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