Cathy Sampson was living the good life of a High School Cheerleader. She was smart, pretty, and popular. Her classes were going better than ever in this, her senior year at West High. Cathy's folks were proud of her, as you would expect.

She always tried to keep an upbeat outlook, no matter what. The example she used was her neighbor, Mr. Ward. Anytime she called him Mr. Ward, he joked that his dad was not around.

"Just call me Jim."

She was amazed at how friendly he seemed to be, even now, less than a year after losing his wife. This left him as both father and mother to their sixteen-year-old son Timmy, a sophomore at West. Jim was a good-looking man, still in his thirties. His son Timmy was a nice enough kid but on the quiet and shy side, so Cathy had never talked to him much.

Cathy felt sad for Jim and often told him not to hesitate to ask if there was any way she could help.

On Friday, Cathy spotted Jim arriving home and getting out of his car. He smiled and waved to her.

"Cathy, can I talk to you for a minute?"

'Sure, Jim." She smiled and walked over to him.

"What's up, Mr. Ward?"

"The name is Jim, Cathy," he joked.

"I have some very good news, but I also may need a favor from you."

"I'm all ears, Jim."

"The good news is that I just got a very nice promotion at work."

"That's fantastic. Congratulations!"

"What this means is that I will have more responsibility and need to do some traveling. Next week, I will be leaving on Sunday and not getting back home until Friday night. Timmy is too old for a babysitter, but he has never been left alone. I'm not sure that I can trust him to get up and off to school on time. That is where you come in. If you can, I am hoping that you could check in with him each morning to make sure he is up and getting to school on time. Of course, I would pay you $20 a day, $100 for the week, if that would work for you?"

"Mr. Ward, I mean Jim, I would be happy to help. There is no need to pay me."

"I know you would, Cathy, but you know that I was given a job with greater responsibility and was given a nice pay raise to go along with that. So, it does not seem right to expect you to take on this responsibility for nothing. Trust me, you will be earning the money, I'm sure. Plus, I know I can trust you, and knowing that is worth plenty to me."

"Sounds great, Jim. I'm sure that Timmy and I will get along just fine. If he wants to, he can even ride to school with me instead of taking the bus."

"I'll let you two work that out, Cathy; meanwhile, here is a house key for you. Feel free to go in anytime you like to help Timmy move along."

Monday morning arrived with Cathy focused on Mr. Ward's instructions. She called the house, and much to her relief, Timmy answered.

"Good morning, Cathy," he said, "My Dad told me that you would check in on me. You really don't need to. I'm not a little kid. I can get myself up just fine."

"That's great, Timmy. I'm happy to hear that. I'm just doing what your Dad asked me to do. I want to be friends with you, not your babysitter. If you want to ride to school with me, just come over in ten minutes."

"That's Okay. I'll take the bus, Cathy."

"Alright, Timmy, I know you will be on time. I'll see you at school. Have a nice day."

Cathy had a good school day, but she never saw Timmy. She knew that she may have messed up by taking his word. She had a cheer practice after school, but as soon as she got home, she went over to see what happened to Timmy. After ringing the doorbell and knocking, she used her key to enter.

"Timmy, it's only me, Cathy. I just wanted to say hello."

There was no answer, but she heard some noise coming from his bedroom. She walked to the door, which was open a crack. Peeking in, she saw Timmy playing a video game with headphones on. She flicked the light to get his attention.

Clearly startled, Timmy shot up from the bed and yelled, "You scared me, Cathy; what's going on, why are you in my room?"

"Timmy, I'm only trying to help. Your Dad asked me to make sure you get to school, and today, I did not do my job. I let him down, and that makes me feel really bad."

"Oh, I'm sorry about that, Cathy. I just didn't feel so good this morning, so I decided that I should take the day off."

"Timmy, you didn't tell me that you were sick. If you had, I could have at least let your dad know why you missed school. Now, he'll get a note from school, and I'll be in trouble with your dad.

"Oh jeez, I guess you are right, Cathy. I am truly sorry about that. I wasn't thinking. I swear it will not happen again."

"You're right, Timmy, it won't happen again. For the rest of the week, I will be here each morning, and you'll be riding to school with me."

"I am sorry that you are mad at me, Cathy. I really am."

"Timmy, I'm glad that you are sorry, and I believe you feel bad about what you did, but still, I just feel like you deserve a good spanking."

"Now I know you are joking, there is no way a little cheerleader is going to spank me."

"Well, Timmy, maybe I was joking, but that is no longer the case. So now, I can pick up the phone and call your dad, or you can come over by me to be punished by 'a little cheerleader'."

Timmy stepped a little closer to Cathy, pleading, "I should not have said that, Cathy. I know that was wrong, but please don't do this. You can't call me Dad either, but I promise I'll be really good the rest of the week."

"Timmy, just stand a little closer to me and keep your hands by your side while I open your pants."

Timmy slowly moved his hands to his side and watched as Cathy confidently slid his belt through the loop and tugged it open. At that moment, Timmy knew more was happening down below that he hoped to conceal from Cathy. It was a little late to think of that as Cathy wasted no time opening his pants and pushing them over his hips. As his jeans dropped to the floor, Timmy's hands were now attempting to provide what cover they could.

"Timmy, you need to stop fidgeting. I've dated a lot of boys, and I understand how everything works. You don't need to be embarrassed; just move your hands away so I can take down your underpants."

Timmy gave up and let his hands go to his side.

"That's a good boy, Timmy. Once I get your underpants down, I need you to just step out of them, and I'll help you to lay across my lap so we can begin your spanking, Okay?"

"Okay, Cathy."

Cathy reached her right hand out and pulled the elastic of Timmy's undies back, taking a long look inside before lowering them to the floor.

"You're a nice-looking young man, Timmy. I can't believe you are only 16. Now bend over my lap, and we'll get you into the best position. That's a good boy, now, just let me know if I am spanking you too hard. You need to be punished, but you also need to be able to sit still in class tomorrow. Right, Timmy?" She smiled.

Cathy brushed her right hand over Timmy's naked bottom for a few minutes, helping both of them get adjusted in their positions. "You were a very naughty boy today, Timmy. I think this will help you to be better the rest of the week."

She gave Timmy a few smacks on each cheek, not really sure how to give a proper spanking.

"Is that too hard, Timmy? You can be honest."

"No, Cathy, those were not hard at all."

"Thank you, Timmy."

Now Cathy began to come down harder and faster, gaining confidence as Timmy squirmed on her lap and even let out an owch, ow, ow, ow, ow from time to time. As she continued, Cathy could feel herself getting warm. The harder she spanked Timmy, the warmer she felt herself getting. She feared that she might overdo it if she did not stop.

She slowed everything down and finally stopped to gently brush Timmy's now rosy red cheeks.

She softly said, "I think that's enough for this time, Timmy. You can get up now."

Timmy got up, doing his best to face away from Cathy.

"Timmy, no, look at me. Has a girl ever seen you naked before?"

"No."

"Well, I guess I may be responsible for your situation. I don't want to just leave you like this. I can show you that girls have ways to help if you'll let me."

"I guess so."

Still seated, Cathy reached out and touched her index finger to the head of Timmy's cock. She observed every reaction with total fascination. She slowly engaged more of her fingers and, finally, her entire hand. She now began to touch, rub, and feel the sixteen-year-old's massive hard-on. Her eye was just a few inches from him; she moved a bit closer, allowing her tongue to gently contact Timmy's cock.

Slowly, she licked around the head for a minute or two before taking as much as possible deep into her mouth. She sucked and licked enthusiastically for nearly five minutes. Finally, she could sense the explosion that was on its way. Timmy let loose a flood of cum into the pretty cheerleader's face and mouth. Cathy swallowed what she could and used her fingers to scoop every drop she could find before licking her fingers clean.

"Timmy, (She said nervously) if you learned your lesson, I will write an excuse for the school tomorrow. But you must promise to be a good boy for the rest of the week. Maybe I can even help with your homework," she smiled.

"Now, have a good night, and I'll be back to see you in the morning."

Cathy was glad that no one was at her house, so she could go right to her bedroom. She had to think about what she had done and understand why she enjoyed it so much. She had never thought about Timmy, let alone considered doing any of what had transpired. She was feeling lightheaded thinking about the size of Timmy's cock and how much she had enjoyed seeing it, spanking him, and then sucking his delicious cum into her mouth.

As she hit the bed, her right hand was inside of her wet cheer uniform panties. She quickly worked two fingers deep inside of her cunt. She was working it hard, bending her entire body into every conceivable position until she had the most massive orgasm of her life.

Wow, her head was spinning. What's going to happen the rest of this week?