Highschool Whore Stories – Cheerleaders Fundraiser

Stacie McCarthy hurried home after school, hoping to find a letter in the mailbox. Her firm 34B breasts bounced under her red and white cheerleader sweater and her pleated skirt flipped up gently over her panty cover as she jogged home. When she arrived home, she was barely breathing hard from the half mile run home from high school. She looked in the mailbox only to find it empty. Disappointed, she went into the kitchen for a glass of water.

“Hi sweetie how was your day at school?” asked her mom.

“Oh, fine, mom”, said Stacie. “I was just hoping to find a letter in the mail from the American Cheerleading Association about this year’s competition. I was sure it would have been here by now.”

“Ask your brother. I think he picked it up already”, her mom said.

Stacie ran upstairs to her brother’s room to find him listening to some music on his headphones and playing air guitar.

“Dave, did I get any mail today?” Stacie asked hopefully.

“WHAT?” said Dave loudly, forgetting he still had the headphones on. He took off the headset and said, “Hey, you got a letter today. It looked official. I tossed it on your bed.”

Stacie went to her room and found the letter lying on her pillow like her brother had said. Excitedly, she tore open the envelope and began reading the letter.

“Congratulations! Your squad has been ***********ed to compete in this year’s American Cheerleader Association competition. Please find enclosed the application form and schedule of events. The competition this year will take place at the University of Hawaii’s campus during the second week of April. Activities during the week of competition include private snorkeling trips, an air tour of the islands and a shopping spree.”

“This is wonderful!” thought Stacie. She had never been to Hawaii and was very excited at the possibility of competing in the contest and seeing the beautiful sights. She read further into the letter.

“Your application form and fee must be received by the end of March to be eligible. There is a $500 competition fee per squad. Hotel accommodations will be at the Diamondhead Hilton at $150 per person per night. A special airline fee of $1,200 per person will cover round trip travel and it is suggested to bring a minimum of $200 per day for meals and other expenses. The five-day competition is sure to be a rewarding trip. We hope to see you and your squad there. Good luck!”

Stacie’s heart sank. Doing the math quickly in her head, the cost for her eight-girl squad would be a minimum of $19,000! There was no way the school would pay for that and she knew not all of the other girls would be able to afford the trip out of their own money. All the girls were excited about the competition and had been working hard all year to tone their bodies and prepare their dance routine. Now it seemed like they would never be able to make the trip. Maybe Mrs. Delaney, their cheerleading coach would have an idea to raise the necessary money, thought Stacie.

Heading back downstairs, Stacie told her mom, “I’m going to go over to Mrs. Delaney’s house. I need to talk about the cheerleading contest with her. The competition is in Hawaii this year and there is no way we can afford to make it”

“Ok, sweetie,” said her mom. “Don’t forget about supper. It should be ready in about an hour.”

“Oh, I’m not really hungry right now, mom. And I can always get something to eat at her house,” replied Stacie.

It was only a couple blocks over to Susan Delaney’s house and Stacie made it there just as Susan was pulling up in her car. Stacie liked the new silver BMW convertible her coach was driving and imagined her driving one like that someday.

“Hi Stacie,” said Susan, “I just got back from the store. Give me a hand with these bags and come inside.”

Once they got inside and had the groceries put away, Stacie handed the application letter to her coach and said it was from the Cheerleading Association. Susan quickly read the letter and looked at the disappointment on Stacie’s pretty face.

“Wow,” said Susan, “this is more expensive of a trip than one last year. I know we don’t have enough in the squad account to cover this.”

“I know,” replied Stacie sadly. “We’ve been working so had all year for this and I know the other girls will be crushed too. What can we do to raise that kind of money?”

Susan glanced over Stacie’s tight cheerleader body. Her breasts were not big, but they were firm. Her tight little ass and slender legs were very attractive and she had beautiful blonde hair and bright blue eyes. The other seven girls on the cheerleading squad all were the most attractive girls in the school and all had kept their bodies well-toned. A plan began to formulate in Susan’s mind on how they would all be able to afford the trip to Hawaii and have some extra money as well.

Susan walked over the small bar in her living room and pulled out a couple glasses. “Would you care for a drink?” she asked Stacie. “I’m going to have a rum and Coke. I’ll bet you’d like it too.”

“Um, I’ve never had rum before, just a little wine at Christmas time,” said Stacie. “I’m only 17 and not supposed to drink”.

“It’s ok. You can have just a little,” said Susan. “It will make you feel better and I won’t tell your parents. Half the kids in your school drink anyhow. You’ve seen the parking lot after the football games with all the beer and liquor bottles there.” Susan filled each glass half with rum and half with Coke and handed one to Stacie.

Stacie took a drink and felt the warmth flood down her throat and into her belly. This wasn’t as bad as she thought it might be. “Thanks, Mrs. Delaney, this is pretty good,” said Stacie.

Susan gave her a warm smile and knew in a few minutes Stacie would be feeling the effects of the alcohol and lowering her resistances. “You know, if we are going to raise the money for the trip, it is going to take a great deal of sacrifice not only from you, but also the other girls. This is a great sum of money and we aren’t going to raise it by selling cookies or washing cars. We have to really put ourselves out. Are you willing to do whatever it takes?” Susan asked Stacie.

“Oh yes, ma’am!” replied Stacie. “I’ll do whatever it takes. We’ve been looking forward to this all year and this is my last year in high school so this is my last chance to win the competition. I know the other girls will do anything also to get the chance to go to Hawaii. We’ve been planning and practicing all year. We just have to go to the competition!” She began to feel warm all over and her thinking getting cloudy.

Susan Delaney could see the effects of the drink begging to take over Stacie. “I need to ask you some personal questions, Stacie. This will help me determine if we can get the money raised for the trip. If you don’t want to answer them, just tell me now and I’ll forget about it. But what I ask you need to stay personal and you can’t tell your family or friends. Do you agree?”

“Ok, sure, Mrs. Delaney” said Stacie.

“Are you a virgin?” asked Susan. “Have you ever had sex with a boy before? And don’t lie; there are tests to check.”

“No ma’am, I’ve never done that. I’ve kissed boys before and even let one play with my breasts, but I’ve never had sex” replied Stacie. She wondered where these questions were leading, but also felt herself getting wet thinking about it.

“Good, Stacie. That is very good,” said Susan. Have you ever sucked on a boy’s cock before? Have you ever let a boy cum in your mouth or let one fuck you in the ass? Have you ever been with more than one boy at a time, letting them play with your pussy, tits, and ass? Have you ever held a cock in your hand and pumped it until it came?”

“Oh, God, no Mrs. Delaney, None of those things, my boyfriend wanted me to play with his…cock…once, but I didn’t want to,” said Stacie. These questions were getting her wetter and she began to squirm in her seat.

“What about the other girls on the squad?” asked Susan? “Have they had sex before, with either a boy or a girl? Have they had a cock pumping into their pussy, mouth, or ass before? Have they licked a warm wet pussy or had theirs sucked?” She could see Stacie was getting excited at the questions and hoped she would be willing to take this even further.

“No, no I don’t think so,” said Stacie. She began to tug at her panties which were now visibly wet.

“Stand up, Stacie” ordered Susan. “I want you to take off your cheerleader uniform and stand in front of me. I want you to take off all your clothes except for your socks and tennis shoes.”

“What?” exclaimed Stacie, shocked? “I don’t know…”

“If you want to go on this trip with your squad, you will have to do everything I ask of you. Everything! If you disagree, then you can forget going to Hawaii and competition,” said Susan forcefully. This would be the minute of truth for them.

“Yes, ma’am, I’ll do it. I’ll do whatever it takes,” said. Stacie. With that, she reached back and began to unzip her cheerleader skirt. She wiggled her hips and the skirt slid over her hips and landed on the floor at her feet. Her nipples began to harden and she slid her sweater over her head and unfastened her bra and dropped it on the floor.

She now stood in front of her cheerleading instructor dressed in only her panties, socks, and tennis shoes. Her nipples were very hard and she began to feel a shiver run up her back at the thought of being almost naked in front Mrs. Delaney.

“The panties too,” ordered Susan. “Take them off as well.” Susan was getting wet watching the teenager strip in front of her and follow her commands.

Stacie slid her thumbs under the elastic of her panties and eased them to the floor with the rest of her clothes. They were visibly wet and Stacie felt a bit embarrassed. She had a light golden patch of hair over her pussy and her body was firm from exercise and her gymnastic routines. She stood naked only two feet from her cheerleading coach and was not sure what to expect next.

“Now, turn around and face away from me, Stacie,” Susan gently said. “I want your legs wide apart and you to grab hold of your ankles for me. I want to see that pretty pussy of yours.”

Stacie turned, kicking her clothes out of the way. She spread her legs wide and bent at the waist and held her ankles, keeping her leg straight. She knew Mrs. Delaney would be able to see her pussy and ass very easily this way and she was getting wetter thinking about it.

Susan saw Stacie’s glistening pussy and puckered asshole. She knew Stacie was excited as she was. Susan reached out and ran her middle finger over Stacie’s wet pussy lips, capturing some of the wetness on her finger.

Stacie jumped at the feeling of a finger running over her pussy and her breath quickened. She had never been touched there by another girl or woman before and the feeling was exciting to her. Stacie watched from upside down through her legs as Susan Delaney ran the finger over Stacie’s wet pussy and then put it in her mouth.

Mike Delaney just got home from work and was surprised to see his wife fingering a naked teen girl in his living room. They both were swingers and had girls from the previous cheerleading squads over to their house before for parties and sex, but here was a gorgeous blonde teen with legs spread wide letting his wife play with her pussy. Mike’s cock began to stir in his slacks as he walked into the room.

“Hi honey, having fun?” he asked.

Stacie nearly fell over jerking her head up to see whom had come into the room. She was so into feeling her coach playing with her pussy that she had not heard anyone walk into the room. She was shocked to see her coach’s husband standing just in front of her. He was an attractive man in his mid-30s with an athletic build. She also noticed a bulge developing in the front of his pants.

“Welcome home, Mike. Have I got a treat for you this evening,” said Susan. “I think you know Stacie McCarthy. She is the captain of the cheerleading squad and we were working out a business proposition I’d like you to hear. Stacie wants to go to the national cheerleading competition in Hawaii this year and needs to raise $20,000 to fund the trip. Do you think you might have a way for eight high school girls to earn that kind of money?”

“That’s quite a bit of money,” replied Mike, “even for a bunch of attractive girls to earn. It does look like at least Stacie is willing to give it her all.” Stacie blushed and moved to cover her nakedness. She was uncomfortable standing naked in front of her coach’s husband and wondered what he had in mind.

Susan said,” Stacie here is a virgin, as I suspect are most of the other girls on the cheerleading squad. I propose having a cheerleader cherry auction. I’m sure you know several of your business contacts that would pay well to fuck a virgin cheerleader. If we can get enough men together I think we can raise the money necessary to take the trip to Hawaii.”

Mike thought about it for a few minutes and said,” I think I can probably find a bunch of my contacts that would be interested. I can get a private club set up for the event and make the arrangements necessary. For the money we are talking about, the men are going to want some great performance out of the girls. I’m talking oral, anal, groups and maybe even some lesbian action. If you can promise that I know we can get the money you need.”

Stacie could not believe where this was going. She had never had normal sex before, and now she was going to be expected to have anal sex as well as lesbian sex. Her confidence was beginning to wane and she thought this might be a bad idea after all.

Susan sensed Stacie’s reluctance and said,” Stacie, if you are willing to go through with this and your other squad members, I think we can get a first class flight to Hawaii as well as deluxe accommodations. The other squads going to the competition are going to be stuck back in coach on the flight and crammed in a lousy hotel. Not to mention spending money on the trip. Wouldn’t you like to have a few thousand bucks each to spend while on the islands? It would be a dream vacation that most of you would not be able to afford again.”

Thinking about the first class flight and money to spend on the trip loosened Stacie up again. It would be wonderful, she thought, to have a grand vacation while competing in the competition. She would be losing her virginity anyhow in a few years and probably to some clumsy teenage football star. Why not get something out of it.

“Ok, Mrs. Delaney, I still want to go on the trip and am sure I can convince the other girls it is as good a deal,” Said Stacie. “Since I’ve never had sex before, how do I know what to do? I think we will need some help figuring out what to do if we are to be good at it. I don’t want to disappoint the men if they are going to be paying so much.”

“That’s the spirit!” beamed Susan. “I can give you some lessons on what to expect and what to do. I don’t want you to actually get fucked in your pussy or ass since they are virgin, but there are other things we can do to get you prepared. In fact, let’s start now. Mike, please stand in front of Stacie. Stacie, I want you to kneel in front of my husband.

Mike moved in front if Stacie and she kneeled before him. Her eyes were at his crotch level and she began to feel wet and tingly in her pussy.

“Your first lesson is going to be how to properly suck a cock,” began Susan. “I’ll talk you through it and Mike will give you feedback on your performance. You will need to be at least proficient in giving a blowjob to a man before the auction. He will understand if you are not as experienced fucking, but you must give him head with some skill. Please begin by looking into my husband’s eyes as you unbuckle his belt and unzip his pants.”

Stacie did as she was told she looked into Mike’s eyes with her pretty blue eyes and felt her nipples harden as she unfastened his belt buckle. She slowly unzipped the zipper and then let the pants fall to the floor at his feet. Hooking her fingers under the elastic of his briefs, she eased them off and was now facing his large cock and balls. The cock seemed huge, and it was not yet hard. His balls were lightly hairy and hung down heavily.

“Very good so far, Stacie,” said Susan. “Now I want you to take Mike’s balls in your left hand and hold them gently and take your right hand and run it along the length of his cock. I want you to get it nice and hard before putting it in your mouth. When you put it in your mouth, use your tongue to lick and explore it; massage it with the wetness of your mouth.”

Stacie complied with her instructions. She cupped his balls in her left hand, gently massaging them and feeling her first pair of testicles in her hands. They felt warm and moved like marbles in a velvet sack. She then took her right hand and encircled his cock, moving it slowly up and down the shaft. As she pumped it, she could feel it growing in her hand. It grew in length as well as girth. It was soon 8 inches long and 3 inches around. She could barely get her hand around it. The head was a nice smooth hardness now and she could see a clear liquid appear out of the slit at the end. She instinctively leaned forward and licked it away with her tongue. It tasted slightly salty and very slick. She began to take the head in her mouth first, letting her tongue roll over it. Leaning forward more, she let more of the shaft slide into her mouth.

Mike moaned his approval at the new cocksucker’s skill. He loved looking into her blue eyes as she sucked his cock deeper into her mouth. Her hands felt warm massaging his balls and he knew she was going to be a natural at this.

Susan could see how much her husband was enjoying the blowjob and thought he is going to really enjoy cumming in the mouth of this teen cheerleader. “All right, Stacie, now I want you to move more of his cock into your mouth,” instructed Susan. “When you push forward into him, try to let it slide past the back of your mouth into your throat. When you pull back, apply more suction with your lips and mouth. Push in, suck out. If you gag some, that’s ok. It will take some getting used to. I want you to really work at getting that cock into your throat.”

Stacie worked it in more and more. She gagged a couple times, but after several minutes, she felt the cock head enter her throat and slide down. She was quite proud of her accomplishment and began to suck his cock in earnest. She liked looking up at the pleasure on Mike’s face and thought this was going to be a great way to earn the money.

Mike was in heaven, looking down at the sweet blonde cheerleader sucking away at his cock. He couldn’t believe it when he felt his cock head enter her throat and she kept sucking away. He felt his cock swell and nodded over to his wife that he was about to cum. He put his hand at the back of Stacie’s head and pulled her face into his crotch. Her red lips now pressed at the base of his cock and her hand massaged his sperm filled balls.

“Get ready, Stacie, he is about to fill your mouth and throat with his sperm,” said Susan. “Keep massaging the cum from his balls and let your throat muscles pump his cock dry”

Keeping her hands working on his balls, Stacie pressed her mouth down his cock shaft, letting it deeply enter her throat. His pubic hairs now tickled her nose and she looked up into his eyes as she felt his cock swell in her mouth. His hands held her head tightly against his crotch and she could not have pulled away if she wanted to. She now felt his cock jump in her mouth and her throat muscles began pumping the warm sperm into her throat and belly. She felt his cock pull back and two warm spurts of cum landed on her tongue. It tasted slightly salty, but it was not bad. It was very slick and she rolled it around in her mouth before swallowing it down with the rest of his big load. As he pulled his cock from her mouth, she pumped the shaft a few more times and coaxed a white drop from it, which she quickly licked off with the tip of her tongue.

“Bravo! Well done,” said Susan surprised at how well Stacie had done and had managed to eat all the sperm without complaint. If the other girls proved to be as well talented, they were going to be able to make the money for the trip easily.

Mike pulled his cock from Stacie’s hot mouth and sat back in a chair. She had proven to be a natural and he couldn’t wait to have her suck him again. Maybe he would bid on busting her cherry, he thought. “Great blowjob, Stacie, you ate my entire load I’ve been saving up. You are going to do great”

Stacie blushed at the complements and felt she had accomplished something great. Sitting there naked, her throat raw from the cock sucking and her pussy dripping from the excitement, she felt there was nothing she couldn’t accomplish.

“I hope you enjoyed your first lesson and my husband’s creamy treat,” said Susan.