Cheerleader Chronicle

A special thanks to my editor Cheer_Smartie526 for all the grammar corrections and excellent suggestions on improving the story.

*

Rick read the test message again.

Ready to try a 3some?

It was from Nancy. It seemed an odd text to receive from someone that was on a date. Rick slowly typed his response

Yes

His phone beeped when she responded.

Call me now.

Rick slowly punched her numbers into his phone... She had specifically told him not to put her on speed dial.

"Hello," Nancy said in a hushed voice

"Hi, It's Rick."

"Everything okay there? How is my favorite babysitter doing?" Nancy asked.

"Yea, everything is fine. Bedtime went very well, he is zonked. We spent a lot of time in the pool, so I think he is down for the night", Chance answered lazily.

"You are awesome. I hope you are not bored."

"No, there is always something here to entertain me", Chance replied.

"You sure you are ready for this?" she asked.

"Yes, is he there?" Rick replied.

"No, he stepped out to take a phone call, some crisis at work."

"Who is this guy?"

"Chance? I met him at a conference about a year ago. We hooked up, and we get together whenever he is in town" Nancy explained.

"And he is okay with this?" Rick inquired.

"I'm sure he will be, once he finds out about it," Nancy said with a giggle, "I told him there was an eighteen year old babysitter at my house. I did not tell him you are a guy. I want to see his face when he meets, you, it's going to be fucking hilarious."

"That's just twisted", Rick said, trying to suppress a laugh.

"He's got a great sense of humor; he will be fine with it. Oh, and as an extra incentive, I will be putting on a little show in the driveway. Shit, he's coming back. I will text you when we are headed to the house."

Rick set his phone down. She had mentioned a threesome with another guy before, but he did not think it would happen so soon. This summer was turning out to be the best ever. Rick walked around the house, picking up toys and generally straightening up. He did not want anything to distract from the action once it started. Just as he finished the phone beeped again.

Be there in 10.

Rick headed upstairs to the office. The window in that room overlooked the driveway. The headlights of her car appeared, and it pulled into the driveway. She had the top down and Rick could see her date was driving. He seemed about Nancy's age. He had spiky blonde hair, and he looked exactly like what Rick expected her date to look like. He started to get out of the car, but she pulled him back in. She was stroking his face and talking to him. Whatever she said, he liked it. A grin spread across his face as her hands moved down his body. She reached across him and hit the button that reclined his seat, and then she began to open his pants.

Rick felt his penis begin to swell. This was not the first time she had seen her do this. The first time had been an accident. This time she had asked him to watch, which made it even more exciting. Rick was surprised that he liked being a voyeur so much.

She had his cock in her hands. It was long. Both of her hands were wrapped around it and there was still some exposed. She quickly took that part into her mouth. One of her hands moved down to stroke his balls. The other began to stroke him as her head bobbed up and down.

Rick wondered if she was just teasing him with a bit of foreplay, or if she was going to take this all the way. He watched closely. Rick was pretty familiar with her technique. She was rubbing the sensitive parts of his cock with both her mouth and her hand. She never stopped stroking him, and only stopped sucking on his cock to say something, probably something sexy. Rick smiled; she was not just teasing him. Rick watched as Chance's hand pushed Nancy's head down until she deep throated him. Rick stroked his own cock through his shorts. He could not wait for them to get into the house.

She was stroking him faster now. Chance grimaced briefly, and then broke into a smile as he thrust his hips up. Nancy's hand stopped. Rick imaged she was gulping down the results of her efforts. She closed up his pants and they got out of the car. Rick heard the front door open.

"And where is the eighteen year old babysitter you kept talking about?" Chance asked.

"Ricky, I'm home. I brought a friend to play with," Nancy called out.

Nervously Rick walked to the top of the stairs; his erection quickly fading as the reality of the situation it hit him. He looked as Nancy and Chance, trying to hide his sheepish expression.

The expression on Chance's face was one of shock. Nancy burst out laughing. Soon Chance and Rick were laughing as well.

"You got me," Chance exclaimed, 'you are a bad, bad girl. I should know better by now, you always have a trick up your sleeve."

"That was a Kodak moment if there ever was one, I will never forget the look on your face when you saw Rick," Nancy said and she turned to look up the stairs, continuing, "What are you waiting for Rick, an engraved invitation?"

Rick walked down the stairs to meet them.

"I'm Chance," the man said extending his hand, "were you in on this, or are you as shocked as I am?"

"Guilty", Rick replied shaking Chance's hand.

"Are you both still up for this?" Nancy interrupted.

"I think I'm at a slight disadvantage for the moment, but hell yea," answered Chance.

"Absolutely," replied Rick.

"I suppose," Nancy said, "I should level the playing field."

She stepped in front of Rick and ran her hand over his crotch. Rick's erection returned so quickly he thought it might have whiplash. She dropped to her knees and began tugging at his shorts. Soon they were around his ankles. Rick eyes darted nervously between Chance and Nancy.

"I don't know why you keep looking at me, "Chance said, his eyes firmly fixed on Nancy, "all the action is down there."

Rick watched as Nancy peeled her dress down, exposing her breasts. She wrapped them around his throbbing erection.

"You want to come on my tits or in my mouth?' she asked.

"M-m-m-mouth," Rick stuttered nervously.

"Mmmm, Yummy," she replied

Nancy wrapped her lips around the engorged head of Rick's penis and started with a very sloppy, wet blowjob. When the entire shaft of his cock was dripping wet she began to stroke him. Rick's concern about not being able to keep it up in front of another man quickly faded. With Nancy's hand and mouth on his dick there was no way his erection was going away.

Over and over her lips and tongue caressed his cock, followed by her hand. The contrast between her soft, wet mouth and her firm grip was rapidly bringing him to orgasm. Each time her hand slide over the head of his cock he inched a bit closer. She had pulled his dick down until it was horizontal, and turned her head to the side so he had an excellent view. The sight of her lips wrapped around his penis was a huge turn on. He was on the very edge. It was that wonderful place where he felt the euphoria of orgasm without the erection ending ejaculation. With all his might he tried to stay in that place. He knew he was probably leaking into her mouth. She pulled her mouth off him.

"I can taste you, now give it all to me."

Her voice overwhelmed him, and his orgasm surged out of his body. The first spurt splashed onto her face. She quickly shoved his cock into her mouth, gulping down the rest of his climax. Her tongue pressed against him, milking the last drops out of his cock. She let his penis slide out of her mouth and she used her tongue and fingers to clean his cum off her face.

"Between the two of you I think I am owed two orgasms," Nancy proclaimed as she stood up and removed her dress. "Now, take off your clothes and come to the bedroom."

"Do not," she said sternly, "turn this into a contest to see who has the bigger dick. That's not important. But; for the record, Chance is longer and Rick is thicker, so you can both make the claim.'

By the time Rick and Chance made it to the bedroom Nancy was already laying in the middle of the bed.

"Alright boys, let's see what you can do," she said, stretching her hands above her head.

Rick climbed onto the left side of the bed and put one hand on her wrist. He kissed her softly on the lips, then on the cheek. He continued down her body. Out of the corner of his eye he noticed Chance was doing the same thing. Rick put his other hand between her legs, slowly stroking the inside of her thigh. Again Chance followed him. Both of them began to kiss Nancy's breasts. Rick's erection was rapidly returning to full strength. Her swollen nipple seemed to beckon to him, but he resisted. Instead he continued to press his lips all over her tit. Nancy was moaning and squirming between them. He glanced over at Chance again. Seeing her with another man was nothing like what he expected. Rick thought he would feel self-conscious and threatened. Instead he felt aroused. He did feel like he was playing a game of chicken with Chance. Both of them were trying to be the last one to finish with her breast and move on to her erect nipple. Rick stopped for a moment and looked at Chance. Their eyes met. At the same time they both engulfed her nipples. Nancy squealed with delight as the two of them pinched her nipples between their lips. Rick could feel heat radiating from between Nancy's legs. He noticed Chance had finished with her breast and started to move down her body. Rick followed his lead, pulling her hand down to her breast. She began to pinch and tug on her nipple as Rick's lips pressed against her ribs.

Rick noticed Chance had put his hand between her legs with his fingers lying on top of her neatly trimmed pubic hair. Nancy moaned as Chance's thumb brushed against her clit. Rick slid his thumb between her ass and the bed. Her skin was wet and hot. His fingers grazed against the lips of her pussy. He slowly penetrated her with a single digit. She moaned again. Rick glanced back up at her breasts. She still had her hand where Rick had placed it. He could see she had pulled Chance's hand to her mouth, and was sucking on his fingers. Chance was pressing the heel of his hand against her clit.

Rick pressed his lips against her thigh, just below her hip. He had a fantastic view of her pussy as he slipped a second finger into her. His index and ring finger were almost completely engulfed. His pointer and pinky were pressed against her swollen labia. Rick began to move his entire hand back and forth. He could hear Nancy's moaning getting louder. Both he and Chance were struggling not to get caught up in her excitement. Rick wanted to maintain the slow pace. He wanted to draw her climax out as long as possible. She began to thrust her hips against them as her orgasm peaked. She was so wet Rick's fingers made an incredibly erotic squishing sound as they moved in and out of her.

"One of you fuckers better put a cock in me now!" she screamed.

Rick and Chance looked at each other, both with an 'after you 'expression. Without warning, Nancy sat up. She straddled Rick, grabbing his cock as she pushed him down onto the bed.

"I guess it's your lucky day," she said as she sank down onto his erection. She felt fantastic. She felt hot and wet and tight.

"You like that?" she asked.

"Uh - huh," Rick replied. He felt her relax around him, then clench up again.

She leaned down and whispered in his ear, "I can be as tight as a virgin if you want me to."

Chance was standing on the bed, offering her his cock. She took it into her mouth and starting giving him and energetic blow job. Rick felt his second orgasm approaching at breakneck speed. He closed his eyes, hoping that not seeing her breasts bouncing around as she sucked one cock and rode another would help. He tried not to listen to her sliding Chance's dick in and out of her mouth. There was nothing he could do about the way she felt. She was still holding him tight inside her. It felt good, too good. Rick surrendered to the inevitable. He opened his eyes, taking in the amazing scene. He exploded inside her again with a loud, long groan. Rick relaxed, feeling completely spent.

Nancy stopped her blowjob and looked at him.

"You're not done yet, you still have to make me come again," she said sternly, rolling onto her back. Chance stepped off the bed, once again putting his cock at mouth level. This time Nancy held still while Chance thrust his dick between her lips.

For a few seconds Rick just lay there in stunned silence. He was not sure what to do. Finally he crawled between her legs and began to lap at her clit with his tongue. He reached up and began to pinch one of Nancy's nipples. Chance once again followed his lead and tugged on the other one. When he pulled his cock out of her mouth, a moan of approval followed it. Rick pushed three fingers into Nancy. She was unbelievably wet, and it turned him on.

Nancy began to buck her hips up and down. Even with Chance's cock filling her mouth and throat Rick could hear her moaning. It went on for almost a full minute before her movements slowed and finally stopped. Rick felt her hand pulling his hair, dragging him across her body until they were face to face. She gave him a passionate kiss.

"That was fantastic," she panted, "but you could have just used a toy. I did not expect you to go down me like that. But I'm glad you did. Now I want you to watch Chance fulfill his debt to me."

Rick watched as Nancy straddled him, and Chance moved behind her. Her breasts were inches from his face. He wanted to kiss them, but he was too exhausted to lift his head.

"This is going to be way better than Skype sex," Nancy said.

Rick lay perfectly still, watching her face as Chance's cock penetrated her. She was looking right into his eyes. Rick briefly glanced at her tits, and then met her stare again. Somehow he found the energy to put his hands on her breasts. He could feel Chance's thrusts as her boobs bounced in his hands.

Rick felt his cock struggling to become erect again. It surprised him how arousing watching Nancy get fucked was. He pinched her nipples between his thumb and finger. Every sound was a turn on. The way Chance's hips slapped against Nancy's ass with every well-timed thrust. The way she groaned and the way her breath hitched as she approached yet another mind-blowing orgasm. The way Nancy talked dirty to Chance. Rick could not believe how long Chance held out. Nancy came with a string of profanity and a flush of heat in her breasts. Chance fucked her for what felt like a long time after her orgasm before groaning and unloading into her. Nancy fell to the bed beside Rick, and Chance lay beside her.

"I hate to tell you this Rick," Nancy said with a broad grin, "but you are going to have to do this until you make me come first. Then I will set you up with me and another woman. You thought this was amazing, two women would probably kill you."

"I won't complain, I promise," Rick replied.

"You did okay kid, not that you need to hear that from me," Chance added.

"He was a virgin a month ago," Nancy giggled.

Rick flushed with embarrassment. He felt ridiculed.

"Really!" exclaimed Chance, "then I am impressed. If someone like Nancy had pulled me into a threesome a month after I started having sex. Shit. It probably would have killed me. I'd have either blown my load in five seconds or just been too embarrassed to do anything. You are a natural at this."

"Thanks, I think," Rick said, feeling a little better about the virgin remark. After all, Chance had followed his lead more than once.

"As much as I want you to stick around, you need to get home," Nancy said, "But I will need your services tomorrow around 10 am. That is, if you are not incapacitated."

"You are right," Rick replied after looking at the clock.

"You might want to take a quick shower before leaving, you probably smell like a Roman orgy," she said with a smile.

When Rick emerged from the shower, he saw that Chance and Nancy had put on some clothes. It sounded like they were talking about work. Rick heard references to databases, scope creep and deadlines. Chance said something about SQL and they both burst out laughing. Rick waved to them as he headed towards the door. He wondered what would happen after he left.