Cheerleader Chronicle Ch. 01

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Chapter 01 – Ms. White

Rick balanced precariously on the peak of the roof. His first odd job of the day was to replace the cable on the TV dish, and it might be his last. The roof had a steep pitch to it and there were very few handholds. This was probably the most dangerous job he had accepted. If any of his other customers had asked him to do it, he probably would have said no. But this was for Ms. White, by far his favorite customer. She paid well and was extremely attractive. Even though a high school senior like himself had no chance with her, being around her made for some spectacular fantasies. It helped that she was recently divorced. Nobody seemed to know why her ex-husband left. They seemed like a happy couple, then one day he moved away. Rick focused back on the task at hand. He checked the mount for the dish. There was roll of steel guy line to steady the dish in his bag, but it was not needed. The mount was still solid. He fished around in his bag for the roll of cable. Once he found it he screwed the connector to the dish and began stringing it along the peak of the roof. He unclipped the old cable and slipped the new one into place. The cable passed into house at a gable over the bedroom.

As he leaned over the roof the push the coax through the grommet he heard a sound through the open window. It sounded like moaning. He leaned over the roof and peered through the windows. The curtains were open, giving him an unobstructed view into the room. She was laying on the bed completely naked. One of her hands was on her breast, the other was between her legs. She was sliding a dildo in and out of her pussy. From his vantage point he could see that she was completely shaved. Rick instantly had an erection. He filed the image of her masturbating away for later use. The position needed to see through the windows was extremely unstable. He pulled back from the edge. Nancy, as he called her in his fantasies, was hot. But she was probably not worth falling off the roof. He listened to her moans of pleasure, then he heard his name. He had to go back. He pulled the steel guy wire out of his bag and looked around at the roof. One of the eyelets he had installed for the dish was only a few feet away. Doing his best MacGyver impression, he threaded the wire through the eyelet, and then through the buckle of his wilderness instructor belt. He had read that the belts could be used as an emergency rappelling harness. He was about to find out how that worked. He spun the belt so that the buckle was in the back, then dangled his feet over the edge of the roof. Slowly he leaned forward, extending his legs towards the wall over the window. So far his estimate of how much wire to use seemed to be right on. Just as he slipped off the edge of the roof his feet touched the wall. Slowly he walked up the wall until he could put his feet on the underside of the eaves. Ever so slowly he straightened his legs. He felt blood rushing to his head. The he saw her again. Both her hands were on the toy. She was thrusting it between her legs roughly. His new position made it a lot easier to hear what she was saying.

“Fuck me hard Rick. I want your cock inside me. I want to feel all of you. Don’t stop, please don’t stop.”

Rick could not believe what he was hearing. It had to be another Rick, but that did not make him any less aroused. She had spread her legs wide, and Rick could see the light pink lips of her pussy stretching around the toy. Each time she rammed it into herself it caused her breasts to bounce up and down. Her dark brown nipples stood out from her milk white skin. Her head turned from side to side, and strands of her raven hair stuck to her sweat soaked face. She planted her feet on the bed and lifted her hips up, thrusting the toy into herself at a slow and deliberate pace. Rick had to put both hands on his belt to keep it from falling out of his makeshift harness. That was the only thing keeping him from stroking his own cock.

“Make me come Rick. Fuck me till I come all over your cock. You feel so good,” she screamed, her words becoming moans as she was overwhelmed by her orgasm. As her climax subsided, she pulled the toy out of her pussy and plunged it into her mouth. The sight of her lips tightly pursed around the dripping wet sex toy almost made him lose his balance. Rick quickly scrambled back onto the rooftop. Once his attention was no longer on his naked employer he began to pay the price. His head hurt from being upside down, and his waist stung from the pressure of the belt. He realized why it was a harness for emergency use only. The silver lining to all the pain was his erection subsided. After a few minutes he was able to complete his work on the roof. He climbed down and knocked on the door. Ms. White answered, now dressed in a bikini. Her nipples stood out noticeably under the thin fabric.

“I’ve told you that you don’t have to knock each time you need to come in. Did everything look good on the roof?” she said with a smile.

“Yes. The dish is solid, I did not need to tie it down. I canlı bahis just need to get into the attic to patch the new cable into the distribution box.”

“Okay. Would it be too much trouble to have you check each set? I’m sure they are fine, but it would suck if one of those cables was bad as well.”

“No problem.”

“I will be by the pool if you need anything, “she said, walking back through the house.

Rick paused, watching her walk till she was out of sight. He quickly completed his task in the attic, then began checking each set. When he arrived in the bedroom he turned on the set. The picture looked fine. He turned and looked at the bed. The impression she had left in the bedspread was still there. Rick walked over to the bed and ran his hand over the contours left by her body. Poking out from under the pillow was the dildo she had been using. Rick reached for it, but stopped himself. As much as he wanted to touch something that had been inside her, he felt like he would be violating her trust, even though she probably left it exposed on purpose.

The rest of the day’s chores were pretty uneventful. He did get watch her by the pool while doing some of the yard work. She alternated between reading and working on her computer, with an occasional dip in the pool… It was easy to imagine her naked, her swimsuit was very revealing. He was relieved when she left, the effort of hiding his throbbing erection was beginning to tire him out. He quickly finished his remaining tasks and returned to the house to let her know he was done. He was anxious to get home and make use of his new knowledge in private. She was waiting for him just inside the front door.

“Sit down Rick, I want to talk to you about something,” Nancy said with a mixture of apprehension and regret in her voice.

“Sure Ms. S, is something wrong?” Rick answered, suddenly feeling nervous.

“Nothing’s wrong. Do you remember the first time you worked for me?”

“Yes, it was last year. It was a babysitting job. I watched Jake while you went out for the evening.”

“Do you remember what you said to Jake?”

“Not really, did Jake say a bad word or something?”

“No, Jake still isn’t saying any words. I don’t know how to say this, so I am just going to blurt it out… Even though you came highly recommended, I set up a nanny cam the first time you were here. Do you know what that is?”

“Yes, and I can’t say that I blame you. Guys in my age group are not always known for making responsible decisions.”

“Do you know what I heard you say on the recording?”

“Yes,” Rick replied, the color draining from his face.

“Now do you remember what you said?”

“Yes, and I don’t know what I was thinking… I was just joking around with the little guy.”

“It’s pretty obvious what you were thinking, and I am flattered.”

“You’re not mad?”

“Not at all. Whenever I am depressed about something, I play that video. It always cheers me up… hearing you tell Jack how ‘ momma has a nice rack’, and how jealous you are that he gets to see me topless, I don’t know how anyone could be mad at that.”

“That’s a relief.”

“There’s more. I want to know if you really meant that,” Nancy said.

Rick opened his mouth, but no words came out.

“I’ve been wanting to talk to you about this for a while, but until you turned eighteen, well, it would have been awkward. And probably illegal.”

“I really meant it, “Rick blurted out.

“Now I am relieved. Do you know why my husband left?”

“I have heard stories, but I don’t know if any of them are true.”

“Jacque left because he is gay. He found his soul mate in another man, and the three of us could not make it work. You’ve probably never lived with a couple of gay lovers, so you can’t understand what it was like. Jacque is a good guy, but his new lifestyle was something I just could not handle. Which leads to the stories I have heard about you. Rick, why are you a cheerleader?”

“Because it is the closest thing the school has to a gymnastics program, and that is the only sport I find interesting.”

“So it’s not because…”

“I’m not gay if that is what you are getting at. I don’t know where that story got started, but it’s not true”

“So you don’t have a cheerleading skirt and pom poms?”

“That was a really bad idea for a Halloween costume, nothing more.”

“So all the girls on the cheer squad think you are gay? Are you sure they are not just hazing you?

“Two of them have asked me for advice on giving blowjobs, and they undress in front of me.”

“Really, they get naked?”

“So far just topless.”

“Doesn’t that make you horny?”

“Not really, I figure there is no chance, so why bother being frustrated. It would be different if any of them seemed interested in me,” Rick replied.

“I’m glad you are not gay?”


In response Nancy stripped off her T shirt. She took Rick’s hand and put it on the zipper of her sports bra.

“Because I want you. bahis siteleri You will be gone off to college soon, and I want you until then. This isn’t dating… It will just be about sex. You will be free to date anyone you want, as will I. When I was your age the term was Booty call, I think you kids call it hooking up.

Rick’s head was swimming. He had been lusting after Nancy since the first day he saw her. He would have done all the babysitting and odd jobs around her house for free, just to see her by the pool in a bikini.

“In fact, I will sweeten the deal. I bet we can find a way to make some l of those cheerleaders interested in you. And if you play your cards right, you can avoid all the drama.”

Rick was stunned. He had resigned himself to being a virgin until he got out of high school and moved away. Nancy was offering to cram four years of sex into a few months.

“You don’t have to say anything, just unzip my bra if the answer is yes.”

Rick pulled down on the zipper. Slowly the material spread apart, revealing her breasts. When the zipper reached the end of its track the bra fell open. Rick stood there, transfixed. It was the first time he had seen breasts in real life.

“You can touch them,” she offered.

Rick continued to stand still.

“This is what I like,” she said, guiding his hands to her tits. She positioned them slightly off center, so that her nipple protruded between his thumb and pointer finger.

“Now squeeze them hard. Don’t worry, you won’t break them.”

Rick did as she asked, and she moaned in response. They were harder than he thought they would be. He felt her erect nipple against his thumb, and pinched it against the side of his fingers. She squealed with delight.

“You are a natural at this,” she exclaimed.

“Can I kiss them?” Rick asked.

“You can kiss me, my breasts are not something, and they are part of me. You can kiss me on the breast if you like. I hope you don’t mind if I watch you.”

Rick awkwardly leaned forward and pressed his lips to her firm breasts. He wrapped his lips around her nipple and licked it with his tongue. Her moans of enjoyment were music to his ears. Rick gently pinched her swollen flesh between his teeth. She groaned in response.

Nancy lifted one of his hands from her breast and brought it to her face. She slipped his finger between her lips and began to suck on it. Rick moaned in response. For a few moments they stood there, gently sucking on each other. Then Nancy slowly pushed Rick away.

“That’s enough. I want you to go home and think about my offer. This is not something to be decided in the heat of the moment. I will call you later,” she said, looking him directly in the eye.

Rick watched as she slowly zipped up her bra. He knew the answer would be yes, no matter how long he thought about it. He just hopped his erection went away by the time he got home.

Much to his relief his cock and returned to its relaxed state by the time he walked in the front door. His parents were both out and there was a note on the fridge with instructions on how to heat up dinner. It was not unusual for him to get home late from either work some other activity. He went straight to his room and shut the door. As he stripped off his clothes he began to think about her. He imagined her naked on the bed, just like he had seen her earlier. Rick picked up a bottle of sunscreen and poured it into his hand. It was from her house. She had always insisted that he wear it, frequently helping him apply it. He had several bottles that she had stuffed into his backpack or even back pocket. Now he wondered if she more interested in touching him than reducing his UV exposure. It was a tough call, she always wore sunscreen herself.

Tonight there was no sun in his room, the lotion was going to serve a different purpose. Rick lay down on the bed and began to stroke his bulging erection. He knew the answer to her offer would be yes. His hand slid up and down, smearing the sunscreen all over his cock. The smell only made the fantasy more real. He thought of her naked by the pool. They would cover each other in lotion, then let their bodies slide against each other. It was that thought, her naked body sliding over his, that triggered his orgasm. Copious amounts of semen spurted out of his penis, covering his chest and belly. It was over almost before it has started. Rick started to clean up, making a mental note to use something else for lubrication. Something that did not smell like her, something that would not be as much of a turn on, like axle grease or gear oil. He laughed to himself. Even something as rough smelling as that probably would not stop him. Maybe he would just focus on her breasts instead of her whole body. He finished cleaning up, slipped on some shorts and made dinner. When he finished he contemplated watching TV, but found himself lying in bed again, thinking about her. The phone rang, the caller ID showed it was her. He answered


“Hi Rick, it’s Nancy. Have you thought about bahis şirketleri my offer?”

“I have, and the answer is yes.”

“I thought it would be. Have you jacked off yet?” she asked.

Rick paused, surprised she was so direct, “Uh, yes.”

“How many times?”


“Then I am ahead of you. As soon as you left I started playing with myself. Just thinking about your mouth on by tits made me come. I tried to get some work done, but I kept thinking about you, so I went to my room. Do you remember what is in my room?”

“Yes,” Rick answered eagerly.

“So I fucked myself with a vibrator, wishing it was you. Holy shit, I’m getting wet again just talking about it. Wanna have phone sex with me? Since you are new to it, I will do all the talking.”

Rick looked at the clock. He would be alone for at least another hour.

“Well, you want to listen to me talk dirty?'” she asked.

“Y..y.. yes!” Rick stammered.

“I’m sure you have some hand lotion or something.”

“I have some sunscreen from your house.”

“That’s perfect, I have some too. I’m going to rub it on my tits and pretend it’s you.”

Rick lay down on the bed, kicking off his shorts.

“How long did you take last time?” she asked.

“Not very long,” he answered remorsefully.

“We will need to work on that. Hold out as long as you can without hurting yourself. Can you get it up again?”

“Yea, yea, I’m ready.”

Rick heard the phone click as she put him on speaker. He was not as bold, cradling the handset against his ear. The sound of sunscreen spurting out of the bottle came out of the speaker.

“Oh my, there is some much. It looks like you came on my tits. I want you to think about rubbing it in. Don’t touch yourself yet, just think about my breasts slipping around in your hands.”

Rick moaned. Not touching himself was proving to be quite a challenge.

“Now, think standing in front of me. I go down on my knees, and put my hands on my breasts, spreading the sunscreen all over them. I’m pinching my nipples between my fingers. Mmmmm, that feels so good. Not as good as your lips, but pretty good.”

Rick had an excellent visual of the scene in his mind’s eye. He heard a faint buzz as she turned on her vibrator.

“You can begin stroking yourself now, because that is what I would do. I’d put both my hands on your nice hard cock and slide them up and down. Up and down. Up and down, over and over again.”

Rick moaned again as she repeated those words over and over. It was easy to think that it was her hand on his dick instead of his own.

“If you need to stop for a second just say so, I don’t want this to be over just yet. I can enjoy myself very quietly if need be.”

Rick closed his eyes and imagined Nancy on her knees by the pool. She was giving him a hand job as he watched her perfect breasts sway back and forth. He felt pressure building and opened his eyes, staring at a spot on the ceiling.

“I think I need a break,” Rick said through gritted teeth. The phone went silent for 30 seconds.

“Is it better now?”

“Yea, yea, I’m good.” he replied.

“This is the home stretch, we are not going to stop again,” she purred.


“Are you thinking of me again?”

“Yes, oh yea.”

“Picture me wrapping my breasts around your cock and sliding them up and down. Do you like the way my tits feel?”

“Uh Huh.”

” I like it too, now I want you to start thrusting.”

Rick began to move his hips up and down on the bed. He knew he was not going to last much longer.

“That’s it Rick, fuck my tits, fuck them hard.”

All Rick could do was groan in response. Little drops of cum were spurting out of his cock. He felt like the top of his dick was going to explode.

“Fuck me hard Rick, come on my tits. Come all over me. I want to feel your hot sticky cum all over my face!” she screamed into his ear.

Rick’s orgasm burst out, except instead of covering her body he covered his own.

“Ahhgg,” he yelled.

“Are you okay?” she asked, breathless from her own climax.

“Yea, yea but it’s on my face.”

“Isn’t it great?”

“Uh, not really.”

“Can you taste it?”

“I’m not gay, remember,” Rick replied.

“I’m not a lesbian, but I know what my pussy tastes like. If you expect me to swallow it, you can at least try it,” she chided.

There was a moment of silence.

“Uh, salty, and not really my bag,” Rick finally said.

“I guess it’s an acquired taste, “she giggled,” You did very well. I will call you back in thirty minutes and we will try again.”

“I might not be home alone in 30 minutes, “Rick replied nervously.

“Good, the fear of getting caught will make it more exciting.”

The next thirty minutes seem to take forever. Rick cleaned up again. He took a shower to rinse of the sunscreen. His room was starting to smell like a tanning salon. Finally the clocked ticked off the last minute. The phone rang precisely on time. Before he even said hello is erection had returned.

“Are you ready?” she asked.


“That’s what I Love about young men, ready again so soon. Did you jack off while you were waiting?”

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