Cheerleader Chronicle

Note- Thanks to Cheer_Smartie526 for helping edit and develop this story.

*

Rick replaced the filler cap on the engine and closed the hood. He turned to look at Nancy. She was peering at him over the top of her laptop computer.

"I don't know why you pay me to do this; you know how to change the oil in a car. Especially this car, since you pretty much built it," he said.

"Two reasons," Nancy replied," I have changed the oil on enough vehicles that the thrill is pretty much gone..."

"And? " Rick inquired.

"And I never miss a chance to have you bend over and show of that nice ass of yours," she said with a seductive smile.

Rick blushed. He had gawked at a lot of nice asses, Nancy's included. He had never thought of himself on the other side of that situation. It was an odd feeling.

"So, are you going to tell me about your date with Courtenay? Did you do what I told you to do?" Nancy asked.

"Well, kind of ..." Rick replied, "I really like this car." He ran his hand over the hood of the car.

"Me too," Nancy answered, "It is fun and a real guy magnet. Sometimes they are disappointed that it is a kit car and not a real AC Cobra. I can usually rekindle their interest when I tell them I put it together myself. But I don't want to talk my car. I want to talk about your date."

Nancy shut her laptop and looked at him sternly. Rick could see her nipples poking through her shirt. He knew she was going to want to hear every detail.

"She did not exactly follow my instructions." he said.

"How so?"

"I told her not to wear panties, and she had some on. The rest of her outfit was exactly what I asked for, just the one thing," Rick explained.

"Did you make her change?"

"No, I changed the plan a little."

"And did that work?' Nancy asked.

"Sort of," Rick replied

"So tell me about it," she said.

"I changed it to just dinner and a movie. I think she really enjoyed both. She seemed a bit surprised when I took her home after the movie. I'm pretty sure she was disappointed when I did not kiss her." Rick said.

"What makes you so sure?"

"Well, I slipped her a little gift..."

"Oh?" Nancy interrupted.

"I put a vibrator in her purse. I modded it just a bit. It has a wifi chip in it. I can tell when it is on," Rick explained.

"And did she turn it on?"

"Yes, about 30 minutes after I dropped her off. It was on for about seven minutes."

"Clever boy," Nancy said," but I think I need to give you another lesson on being in charge."

Rick stood still as he watched Nancy walk across the garage. She took a coil of rope off the shelf by the workbench. He felt his pulse quicken as she turned towards him. She put her left foot on the mechanic's stool. She had very sexy legs, and the shorts she was wearing did a great job of showing them off. Nancy flexed her calf and gave the stool a push. It rolled across the floor, stopping when it hit a column.

"Take off your clothes and sit down," Nancy said to Rick.

Rick slowly began to remove his clothes. He pulled his T shirt over his head and tossed it to the floor. Nancy's eyes followed his every move. She smiled at the sight of his broad chest with its curly brown hair. She watched his powerful legs flex as he slipped off his shoes, and then peeled off his socks.

"Everything," Nancy said impatiently toying with the rope in her hands.

Rick slipped his thumbs into the waistband of his shorts. He wondered if she was upset with him for the way the date went. Slowly he slid his shorts and underwear to the floor and stepped out of them. His cock was already fully erect. He sat down on the stool.

Nancy walked over to him. First she tied the base of the stool the column, and then she locked the wheels of the stool.

"Safety first, I don't want this to slip out from under you, "she said quietly.

Nancy tied one end of the rope around Rick's left wrist, and then placed his hand on his thigh. She placed his right hand on the right edge of the stool, then pulled the rope tight and tied it around his wrist. The rope had just a bit of slack in it, but Rick could not move either hand very far. She had tied the rope so he could not quite reach his penis with either hand.

"What you need to understand before you next date is the value of delayed gratification," she said, slowly peeling her shirt off.

Rick smiled as her shirt slipped over her head.

"You do know what delayed means, don't you?' she asked.

"Yes," Rick replied.

"I know you are still learning your limits. Tell me if you think you are getting close. Think about old nuns playing baseball naked or something. Do you understand?" she asked.

Rick nodded.

She slowly pulled her shorts down, revealing a silky red thong. She turned away from him and bent over until her palms were flat on the floor.

Rick's eyes were drawn to her firm round ass. He could see that the thong was damp between her legs. He tried to touch her, but his hands were restrained. He tried to lean forward, but she was just out of reach. He watched her stand straight up and turn to face him again. Her breasts were almost at eye level to him. Her nipples were swollen and dark. He longed to feel them between his lips. She followed his stare, and then cupped her tits in her hands.

"You like?" she asked coyly.

Rick nodded. He watched as Nancy dragged her fingers through her cleavage and then across the top of her breasts. She let out a quiet moan. With her fingertips pressing into her firm tits she moved her pinkie down to her nipple. Her finger circled the swollen nubs with excruciating slowness. Rick felt his cock begin to ache as he watched Nancy touch herself.

"Am I turning you on?" She asked.

Rick nodded eagerly.

"More than if I just shoved my tits in your face?"

Rick nodded again, this time slowly.

"And if do this?" she asked as she slid one hand down her body.

Rick watched her hand as it passed between her breasts and moved across her belly. Her fingers disappeared into her thong. Rick heard Nancy penetrate herself. He could see the outline of her fingers under the thong as she slipped them in and out of her pussy. She moaned again. Nancy spread one hand out on her breast, letting the nipple poke out between her index and ring finger. She began to caress her breast and pinch her nipple.

"You like?" she asked.

"Y,Y,Yes," Rick stammered.

Continuing to toy with herself Nancy slowly dropped to her knees in front of Rick. She lowered her head towards his cock.

"Hold completely still, understand?" She said.

"Yes," Rick groaned, already feeling an orgasm building.

Nancy continued to lower her head. She opened her mouth wide and covered the head of his cock with it. She did not touch him. Rick could feel her warm breath flowing down the shaft of his cock. A few drops of pre-cum bubbled out. When Nancy moaned Rick both heard and felt it. He watched her raise her head until her lips were just above his dick.

"Are you close?" she asked.

"Uh-huh," Rick replied.

"I am too," she said.

She pursued her lips and began to blow. The air felt cool where the pre-cum had wet his dick. Rick felt a chill run up his spine. Rick could feel Nancy's moan of pleasure vibrate though his cock. The wet sound of her fingers between her legs got louder and faster. He could hear and feel her breathing getting ragged. She began to yelp quietly, and then she took a deep breath and held it. Finally she let it out with a loud moan as she climaxed.

"Turned on?" she asked.

"Fuck yes!" he replied.

Nancy removed her hand from between her legs and slipped her wet fingers into Rick's mouth. He began to suck on them, reveling at the chance to finally touch her.

When she pulled her fingers out of her mouth she bent her head down again, holding her lips less than an inch from his cock. Once again he could feel her breath on the head of his dick.

"I'm going to make you cum," she said, talking into his penis as if it were a microphone. She lowered her head a bit more so that he could feel the heat of her mouth, but she was not touching him. Rick felt Nancy's tits rub against his knees and he could hear her masturbating again. She began to breathe harder, and her hot breath flowed down the length of his penis. When she moaned Rick felt it more than he heard it. Rick strained against the ropes, trying to touch her breasts.

"You feel so good," Rick moaned.

Nancy lifted her head and looked into his eyes. She took her hand from between her legs and wrapped it around his dick, smearing her wetness all over him. She wrapped her tits around his cock and began to slide them up and down. Rick felt his orgasm rapidly building.

"I want you to watch me stroke your cock with my breasts," Nancy moaned, "then I want you to come on your face."

"My face?" Rick asked.

"Yes. You know how it turns me on. What's the matter, don't think I can make you come hard enough to reach?" Nancy teased.

Rick lowered his head and watched his throbbing erection slide between Nancy's tits. She rubbed her nipples with her fingertips. He was both transfixed and aroused by the sight.

"I want to see you cum. Give it to me, give it to me. Cum for me baby," she whispered.

Rick's climax erupted out of his cock. Thick streams of cum splashed onto his cheeks and chin. The following spurts flowed onto Nancy's tits. He heard her squeal with glee as the warm fluid coated both of them.

Nancy put her hands on his shoulders and pushed him upright. She climbed into his lap, guiding his cock between her legs. As Nancy impaled herself on him she licked and slurped the cum off his face. He felt her arms wrap around him and her breasts flatten against his chest. Nancy cradled his head in her hands and she feverishly licked him clean. Rick began to rock his hips back and forth, driving his cock deep inside her.

"Yes, yes, your cock feels so good. Give it to me, give it to me. Fuck me till I come, "she whispered into his ear.

Rick could feel her clench down on his dick. He bucked his hips against her, hoping his erection would not fade until after she climaxed. He felt her arms loosen slightly and her cum-soaked tits began to slide against his chest. His hands were still tied to the stool, and she remained just out of his reach.

She pressed her forehead against his, staring at him. He could see the lust burning in her eyes. His cock seemed to have found a second wind as she began to ride up and down on him. She continued to gaze into his eyes without saying another word. She wrapped her arms and legs around him, using her arms to lift herself up and down on him. She slowed down and finally stopped with his cock deep inside her.

"Was it good for you too?" She said with a giggle.

"Unbelievable, and I think I am getting better," Rick said proudly.

"You are, and keeping you on the edge helps you stay hard longer after you come. Do you understand why she needs to do exactly as you tell her?"

"Yes," Rick answered.

Nancy unwound herself and stood up. She bent down and untied Rick's hands.

"Before you do anything else, call her and set up the next date," Nancy instructed. She put her hands on her hips and stared at him. She was still naked.

Rick reached into his shorts and pulled out his phone. He dialed her number.

"Hello, Courtenay, I'm going to take you out again. You know what to wear, and what not to wear. Yes, the same thing I told you last time. We will probably be out pretty late. Okay, meet me at my house at seven. Goodbye."

"That was very good," Nancy said.

"I'm glad you approve, "Rick replied.

"Now I want you to give it a try," she said, handing the coiled up rope to him.

"Here in the garage? "He asked.

"No, there is not really a good place to tie me up in here. Let's try by the pool in the back yard," she suggested.

Rick hesitated. He was pretty sure that her yard was safe from prying eyes, but it still made him a little nervous. He knew if he lived next door and suspected a woman like Nancy would be topless in her yard he would find a way to watch. Rick watched Nancy walking towards the door, still completely naked. He stood up and followed her, shrugging off his concerns.

"What the hell, it should make it more exciting," he mumbled to himself.

Nancy arranged a towel on the picnic table under the pagoda, and then sat on it. She glanced at Rick's cock and smiled when she saw it was almost fully erect.

"Now you have to make a choice that I did not. When I was in charge it was all about keeping you on the edge. You can do that, or you can push the envelope," she said.

"I'm not sure I understand, can you say that again?' Rick asked.

"There might be a few things that Courtenay wants to do, but is afraid to actually say yes to. She might just go along if you just do it. If you decide to push her, you need a safe word. If she says that, you stop. You don't want things to get out of control. You remember what a safe word is?" Nancy asked with a very serious look on her face.

"Yes. Safe word means stop." Rick answered.

"Do you know which one you want? Do you want to tease her or push her?" Nancy inquired.

"I'm going to push her. There are so many things I want to do to her." Rick said with a grin.

"This is not just about your pleasure. She needs to enjoy it as well," Nancy said.

"She will," Rick replied.

"So where do you want me?" Nancy asked.

"Stand with your back against the support column," Rick answered.

Nancy hopped off the table and stood where Rick was pointing. He grabbed the towel off the table and tied it to the column with a taut line hitch followed by a highwayman's knot. Rick created handcuffs from the rope by tying a fireman's chair knot around her wrists. Rick knelt down in front of her and tied her ankles with a simple handcuff knot. The rope ran behind the column, and he left plenty of slack in the line. He stepped back and admired his handiwork. Nancy could squirm a little, but was pretty well attached to the column behind her. Rick thought he should get extra points for being considerate enough to put the towel between the rough wood column and Nancy's backside.

Nancy tilted her head back and looked at the knots holding her wrists to the column. She had to admit, Rick was pretty skilled with a rope. She looked back at Rick. He was just staring at her and stroking his cock. She started to offer a suggestion on what to do next when he spoke.

"I think a little sample of things to come is in order", he said, smiling at his own pun.

Nancy stood still as Rick moved closer to her. He was standing directly in front of her. His chest pressed against her tits. His chest hair tickled her swollen nipples. He bent his knees and slowly lowered himself until they were eye to eyes. His throbbing erection slid down her body until it was pressed against her pubic hair. She felt his hands on her thighs, spreading her legs apart. Rick squatted down a bit more, and guided his penis into the warm, moist channel between her legs. She opened her mouth to tell him he was getting way ahead of himself. Before she could speak he covered her mouth with his, thrusting his tongue past her lips. At the same time his cock penetrated her. Despite this being unexpected, she felt his dick easily slip into her dripping wet pussy.

She felt his hands slide around to cup her ass and he stood up to his full height, lifting her off the ground. His cock was completely buried inside her. She moved her hips back and forth, grinding her clit against the base of his cock. Nancy felt her breasts being flattened as Rick pushed her against the column. This was not at all what she had in mind.

Then Rick lowered her to the ground and stepped away from her. She tried to wrap her legs around him and hold him close, but the rope around her ankles stopped her. She watched helplessly and he stepped back and turned to walk away. She longed to feel the fullness of his cock inside her, but all she could do was watch him walk around the pool and into the pool house. He emerged with the riding crop in his hand. As he approached her he slapped it against his leg. The sound of leather on flesh got louder as he approached. Nancy felt her nipples stiffen as Rick got closer and closer. He stopped directly in front of her. She quickly glanced down at his penis. It was still fully erect, still wet from being inside her. She saw drops of pre-cum bubbling out of it. She wondered how much longer he could last. Nancy brought her gaze back up to Rick's face. He was looking at her tits.

The feel of the riding crop between her breasts startled her at first. She felt the tip slide across her skin, making a figure-eight pattern around her tits. Each figure-eight the crop made brought the small patch of leather got closer to her nipples. She looked down and watched it cross the top of her breast, and then disappear below. Occasionally she felt Rick's cock brush against her ribs, which made her skin tingle.

Finally the tip of the riding crop reached her nipple. Rick tapped her swollen flesh lightly with the end tip. Nancy let out a yelp as a bolt of pleasure erupted from her breast. He did the same to her other tit, and she cried out again. She could see Rick looking hungrily at her breasts as he flicked the leather flap against her nipple. Nancy moaned when Rick leaned forward and put his mouth near her left breast. She could feel his hot breath on her swollen nipple. The riding crop moved to the space between her tits. She wanted his cock there, even knowing he would not last long. His tongue traced the edge of her areola.

"I want you to..." Nancy moaned, but was silenced when Rick pressed the riding crop to her lips.

"In case you haven't noticed, I am going with the taunting paradigm," Rick said, sliding the riding crop along her neck. It continued down her body until it was between her legs. Nancy chuckled at Rick's choice of words. Her laughter changed to a groan as she felt the leather tip lightly tap against the inside of her thighs.

Rick found himself trapped. He had hoped toying with Nancy's body would take him back from the edge, but it had only moved him closer. Instead of getting acclimated to her he was just getting more aroused. He knew the second his cock touched her he would explode. It was his intent to hold her on the edge of an orgasm, but in truth he was much closer than she was. He decided to confess. Rick leaned forward and kissed Nancy on the breast. Slowly he worked his way up her body, across her shoulder, up her neck. He ran his tongue along her ear.

"If I touch you any more I'm going to cum," he whispered apologetically in her ear.

"Do it, just don't stop what you are doing right now," Nancy replied, almost begging.

Rick kissed Nancy on the lips. At the same time he moved closer to her. The moment his cock pressed against her sweat-soaked skin his orgasm erupted. Thick streams of cum gushed out. The first one splattered against the bottom of Nancy's chin. The second coated her right breast. Her nipple disappeared under a puddle of thick white cum. The remainder sprayed across her belly.

Rick began working his way back down her body following the same path he took on the way up. He nibbled on her earlobe, and then kissed her neck. Soon he was back to her breast. He found himself staring at a rather large glob of his own cum. He scooped it up with his tongue, then stood up and kissed Nancy, depositing it in her mouth. She eagerly sucked it out of his mouth. Her tongue ransacked his mouth looking for more. Rick broke the kiss long enough to slurp the cum off her chin. Once again she enthusiastically received it. Bit by bit Rick transferred every drop to her mouth. When he was finally done he found himself kneeling in front of her. He dropped the riding crop, and it hit the ground with an audible thud.