Cheerleader Lindsay Loses A Bet

"Darn," Lindsay said as she looked over her shoulder, having just parked her car. There was no one else in the warehouse parking lot. She checked her phone but already knew she was in the right place. She waited all week for this night but was now worried she would back out. She decided she would smoke a joint first.

She was careful not to get any ash on her turquoise fluffy sweater. She looked good. Lindsay admired her D size tits in the rear view mirror. With her pigtails and red lip gloss lipstick she looked a tad younger than her age of 24.

"Oh well," she thought. "All that getting dressed up for nothing."

Two weeks ago she had made a bet. Being one of the cheerleaders on the Baylor Tech squad she had seen the team roll over opponents all season long. Her boyfriend, Jake Talon, was one of the running backs. He was one of the stars of the team. Jake and Lindsay had been dating since the middle of the season. Two weeks ago they ran into Tyler, Dwight, and Rob, players from their rival, Virginia University. Jake knew a couple of them from his high school. After a few drinks they began trying to one up each other over who would win the big upcoming game in two weeks. Jake and Lindsay were full of confidence. Baylor Tech was undefeated, in contrast to Virginia University, which had lost half their games this year.

"Sorry, you guys don't have a chance of beating us," Jake shouted at them over the loud music.

"Yeah you guys suck I was just looking up your record," Lindsay chimed in.

"What the hell," Tyler snapped back. He was a tall muscular defensive end that had spent most of the season recovering from an ankle injury.

"Especially, you" Lindsay said as she winked at Tyler. Lindsay had a few drinks and couldn't help teasing Tyler who had been eyeing her all night long.

"She knows what she's talking about," said Jake.

"You prepared to back that up Ms. Confidence?" Tyler snarled. "Fancy a bet?"

Jake could tell the others were jealous of Lindsay. She was looking exceptionally hot that night and she had a sharp tongue. Jake liked that she riled them up. Jake slapped Lindsay's ass. Lindsay closed her eyes and bit her lower lip.

"So, you want to place a bet?" Jake asked as he slapped Lindsay's ass again.

It was the biting of her lower lip that drew Tyler and his two friends Rob and Dwight closer.

"Look you guys there is no way you will beat us. If you do, hell, I'll let you have a night with Lindsay," Jake laughed confidently.

"What the fuck?" Lindsay said as she shot Jake a look of surprise.

"Yeah, we will beat you and then nothing will happen," Dwight said as he gave Lindsay a look over. "Sounds like a stupid bet."

Lindsay noticed Dwight eyeing her up for the first time that night.

"You guys all have girlfriends don't you?" Lindsay said realizing her backing down would be seen as a lack of confidence in Baylor Tech winning the game.

"We do but that is not a problem, is it?" Rob said as he moved closer to Lindsay. "It's not a problem for Jake is it?"

"You guys don't have a chance of winning. If you do I would never chicken out of a bet," Lindsay said as she noticed Jake smirking.

"I don't know if you guys could handle her, she is a bit wild," Jake said. Jake was happy to see Lindsay was catching on to his desire to rile up their rivals.

Lindsay remembered Jake saying as much when they first spotted Tyler, Dwight, and Rob. She recalled him saying, "Don't be afraid to flirt with them a little bit. I have a plan to work it to our advantage on game day."

"Her skills are top notch," Jake laughed, "in a deep way. I think it is only fair that you know what you will be missing and I will be enjoying it after whooping you guys in two weeks. How about we make the bet $100 bucks from each of you per point we beat you by."

"A hundred bucks...," Tyler said as he spit out his beer. "Per point?"

"Yeah," said Jake.

"That's a lot of cash potentially," said Dwight.

"Well," Lindsay said as she looked at each of them with a smile. "I will take each of your 5 inches all the way down my throat and let you cum all over my face if you win," Lindsay continued increasing the lustful tone in her voice as she let her eyes flirt with each of them.

"It ain't five inches" Rob said, offended.

"We are going to tear you up if we win," Dwight said as he got face to

face with Lindsay. "You will be sore for days."

Jake pulled Lindsay back from Dwight and put a stop sign hand up as he said, "Hey don't get too close. You can look but you can't touch."

"I'm game. Let's shake on the bet," Dwight said as he winked at Lindsay.

Lindsay winked back. She was very confident there was no way Virginia University had any chance of beating Baylor Tech.

As Jake shook each of their hands Tyler, Dwight, and Rob made sure to make eye contact with Lindsay. Their stares were notably serious but oh so misguided in Lindsay view.

After saying their goodbyes to their rivals they had a moment to themselves as they got ready to leave the bar. Lindsay turned to Jake and asked, "Well that was easy. Did I do alright egging them on?"

"Oh yeah you did. Especially the part about taking them deep and them being only 5 inches," Jake replied.

"Well, how much do you figure you will make?" Lindsay asked. "I mean how much will we make?"

"We should beat them by at least a couple of touchdowns," Jake said.

"I was looking at their stats and they don't have a chance. That Dwight guy's stats don't even show up in the league rankings."

"Oh, he's just coming off the reserve list as he has been injured most of the season," Jake explained as he gripped his chin pondering how Dwight's absence may have distorted Virginia University's lackluster record.

"Really, is he any good?" quizzed Lindsay.

"Well, he is but he is just one player," Jake replied confidently as he quickly dismissed any impact Dwight's return might have.

"Let me look him up," snapped Lindsay as she started scrolling on her phone. "What's this? It says last year he led the division in sacks."

"Yeah, he is pretty good but the team is crap," Jake said confidently. "He only played well against bad teams. Don't worry. Now about the bet. I'll give you some of what we win. I have to play and all you have to do is cheer."

"Well, that is if you win the game. You never told me your friend was defensive player of the year last year." Lindsay said, slightly annoyed.

"Don't worry. We got this," Jake said as he reached for and squeezed Lindsay's nipple. "Hey, you got pretty perky. Those guys turn you on?"

"Stop it," Lindsay giggled. "I was just playing it up. You said it was all part of the plan earlier."

"I know. I just hadn't heard you talk like that before." Jake said. "I know you are pretty innocent."

"I do have an imagination," Lindsay said playfully.

The rest of the evening was fairly eventful apart from a brief encounter that occurred as they left the bar. As they made their way to the bar's entrance Jake had to go back for his phone. While Lindsay waited for him she bumped into a very handsome guy with a French and Australian accent. The interaction was brief but Lindsay found her thoughts recalling the mystery man with the accent and stunning eyes.

A few days passed and Lindsay and Jake were hanging out at Jake's house.

"You told me everything you have done before, haven't you?" Jake asked.

"Yes, I have. And you have told me, right?" Lindsay asked as she looked into Jake's eyes.

Jake replied, "Pretty much....."

Lindsay was quick to spot some evasiveness in his tone. "What do you mean pretty much?"

"Well, you remember Fiona?" Jake said.

"Yeah, the cheerleader who graduated two years ago. The one who always wore a cowboy hat after the games?" Lindsay asked.

"Yes, her, Brad and I had a few wild nights with her. " Jake said.

"Really?" Lindsay asked. "How long ago was this?"

"Two years ago and ...," Jake replied.

"And what..?" Lindsay asked, pouncing on Jake's response.

"And a few weeks ago.... when you were out of town," Jake responded wishing had kept quiet. "It was Brad's idea."

"What the fuck, Jake?" Lindsay asked as her mind raced. Fiona was a bit of a firecracker. Long red hair and a stunner. She drove all the guys and some of the girls crazy. Brad was Baylor's quarterback, and he was supposed to be dating Stephanie, one of Lindsay's friends on the Cheerleading squad. "Does Stephanie know about this?"

"Well, yes, she does," replied Jake.

"And she is ok with it?" asked Lindsay.

"Yeah, well she went out with us the night it happened," Jake answered.

"What did she do, watch?" Lindsay asked.

"No, it is kind of complicated," responded Jake.

"Complicated, explain, " Lindsay urged as her mind kept racing. She was

jealous but at the same time she was very curious as to how all this happened.

"Look, you know I am a bit wild and I am a bit of a stud," Jake said confidently. "I didn't plan it or anything. We went out to dinner and we were going to catch a movie. Turns out Brad had caught Stephanie cheating on him with Monte."

"Stephanie got together with Monte? Wow." Lindsay asked. She imagined Stephanie, a cute little blonde with Monte, the biggest, most muscular black member of the team.

"Yeah, don't tell anyone," urged Jake. "She was pretty drunk and Brad passed out. Monte doesn't drink. Stephanie was flirting with him, and I guess she is a bit of a size queen".

"Size queen? She is tiny, and Monte has got to be huge," Lindsay said wide-eyed.

"Yeah, apparently they had such a good time they woke up Brad who was pissed off at first." Jake said as he carefully watched Linday's reaction. "Apparently, he joined in and they fucked Stephanie pretty good till the sun came up. Brad got her to promise she owed him one."

"Keep going," Lindsay said as she wanted to know how Fiona and Jake entered into all of this.

"Well, the weekend you were out of town, we all went all out. We were going to head out to see a show. The four of us. Next thing you know, Monte comes over and ...," Jake continued to explain.

"And what?" Lindsay demanded earnestly..

"Well, Fiona and Brad had been kind of flirting whenever Stephanie went out of the room," Jake said as he made motions with his shirt as if some invisible force had pulled him into the situation. "Brad was comfortable with flirting with Fiona, I guess, because all of a sudden he was like 'Hey Steph, I am going to cash in that chip you owe me tonight, and I want to hear you and Monte in the next room.'," Jake relayed as he gave Lindsay a look. He was acting coy and innocent. "I was just there to watch a movie, and then Fiona and Brad wouldn't let me leave."

"And you couldn't say no, could you?" Lindsay asked in disbelief. "You didn't tell me anything about this."

"I know. I should have but it was a wild night and I didn't want to blow your mind," Jake said.

Lindsay was mad but also in shock. "So tell me more..." she said with a scowl.

"Brad and I had fun with Fiona. She is a firebox and we had a good time," responded Jake. "And you should have heard Stephanie. She was having a crazy time. At first Brad, Fiona and I just sat there on the couch as we heard Monte and Stephanie in the next room. Stephanie was really loud. She started cumming and screaming like crazy. Moaning and hollering all night. As this was happening Fiona got between Brad and me. She started rubbing her hands up and down our jeans."

"You sure she wasn't faking it or taking advantage of Monte?" Lindsay said, trying to make light of the situation. "So what happened next?"

"Well, before I knew what was going on Fiona had unzipped our pants and was going back and forth, giving us head. But that was it. I didn't fuck her," Jake said faining innocence.

Lindsay gave Jake a serious look.

"So you ain't too mad?" Jake asked.

"No, I am not but I am pissed you didn't tell me." Lindsay said as she tried to recall if there had been any hints of this wild escapade. "You know I have to say I have noticed Monte lingering around Stephanie."

"Yeah, it's a secret. Brad and her have kind of an understanding now." Jake explained.

"An understanding?"Lindsay asked.

"Yeah, I can't really say more," replied Jake.

"Gosh, everyone is going wild and I didn't know a thing about it," Lindsay said in frustration.

"Well, I guess you will have a fun time if we lose the game in two weeks." Jake snickered.

"What is that supposed to mean?" Lindsay asked puzzled.

"Look, I know you couldn't handle that kind of situation. Don't worry we are going to win for sure. We will both be making some money. Remember it is 100 bucks from each of them per point," Jake said confidently.

"So three hundred per point. So if you win by 14 points ----- $4,200 bucks," Lindsay said with glee. "Do you think they will back out of it?"

"No chance. I already secured the money," Jake said as he flashed Lindsay a look at his phone.

The phone showed a message from Wilson. It was a receipt for $6,000. There was a memo attached to the receipt which said $6,000 39+21.

"What does this memo mean?" asked Lindsay.

"Oh, 39 that is 3 times 13," responded Jake.

"And what does that mean?" asked Lindsay, confused by the last two numbers.

"Well, think about it Ms. Deepthroat." Jake said as he grabbed Lindsay and pulled her head towards his pants. He then unzipped his fly and pulled out his very erect 10 inch cock. "Open your mouth," Jake said excitedly.

Lindsay opened her mouth and took Jake's cock deep down her throat. He held her tight for a long time and then let her up for air. Lindsay gasped. Jake hadn't been this forceful before. No one had. She was caught by surprise but also very turned on. Jake forced her head down again and began to squeeze her nipples hard. He let her up for air and then turned her on her back. He then began to fuck her throat harder and harder. Lindsay gasped but kept pace with his thrusting motion. Soon Jake started to cum. He pulled his cock out of her mouth as he came all over her face. She gasped for air. Her nipples were very hard.

"That was hot" she found herself saying.

"Glad you liked it." Jake said.

"Now will you explain how you got them to put down $6,000 and what does the 39+21 mean?" asked Lindsay as she wiped the cum off her face.

"Well, you know Tyler, Rob, and Dwight are pretty big guys," Jake replied.

Lindsay pretended to think for a second and then nodded her head sarcastically as he was stating something obvious.

Jake continued "Physical, big guys, big hands, and well, they claim they are thirteen inches each."

"Thirteen inches," Lindsay roared with laughter. "You can't be serious? No one is that big."

"Look, we're going to win the game. We are unbeaten and Virginia has lost half their games this season," Jake answered, trying to reassure Lindsay there was nothing to worry about.

"And who is Wilson?" asked Lindsay.

"Oh he's their other defensive tackle. He was at the bar the other night. I think you bumped into him on our way out."

Wilson was the mystery man. Of course Lindsay remembered the encounter. After egging on Tyler, Dwight, and Rob for a good hour or so she was ready to leave. Jake was in the bathroom again. Lindsay was having some fun. Flirting a bit extra while Jake was gone. She had even rubbed up against each of them briefly. The boys showed some control and did as good a job as they could to exhibit some restraint while encouraging her behavior. Jake returned from the bathroom. As Jake and Lindsay headed out of the bar there was a bit of a human traffic jam near the entrance. Jake had forgotten his phone and went back inside. As he left her side, Lindsay turned and collided with a very large man. He was well dressed and very attractive. Lindsay had stepped on his shoe and as she began to slip the man caught her fall. As she got to her feet the man caught a birds eye view down her shirt. He could see her amazing tits wrapped in a black silk bra.

"Oh, I am so sorry," said Lindsay.

The man smiled and grinned,"Oh,that is quite all right. You can run into me anytime you like," he said with a thick Australian and French accent.

Lindsay giggled as she adjusted her silk shirt. One of the buttons had come undone. She struggled to put the button back in its hole. NoticIng the man still smiling and looking at her, she gushed, "I love your accent."

"Oh, thank you. I love your accent as well," the man said, smiling as he offered her his hand to help her from teetering over.

Lindsay smiled as she steaded herself. His eyes were really amazing to her. Something about their blueness, they were a light sky blue. Lindsay felt a bit of electricity from his touch.

"Allow me," said the man, as he motioned that he would help her button her shirt.

"Sure," Lindsay said. As she did she thought, "Why did I just invite this man to touch me? With those eyes and accent, how could I not." She couldn't stop looking into his eyes as she began to blush a little.

The man gracefully brought his massive hands together. His fingertips slightly touched each of her breasts while pulling the sides of her shirt together. It wasn't easy to get the button back in the buttonhole, but the man concentrated and managed to do it. Once the button was in place he gave it a slight tap and then let his hands glide just across her breast. The nails of each index finger made a subtle dip as they passed over her nipples. His nails making contact with her nipples sent a micro jolt of electricity through Lindsay's body.

Lindsay blushed. She thought to herself, "Whoa. How did that happen? How did he manage to get both my nipples at the same time? Normally, this sort of a behavior would warrant a slap and an insult. But this was not your typical cop a feel of some tits behavior. This wasn't some awkward lunge that I am used to. Those don't feel nice and are, luckily, easy to avoid with a quick turn. This did feel nice."

"Must be cold out here," the man said as he continued to stare back into her eyes.

Lindsay looked down at her shirt. Her nipples were unusually erect. "Ah, maybe," she replied with an air of mischievous flirtation. "That wasn't easy was it?"

"Well that button seems a bit bigger than the rest," the man responded maintaining eye contact.

"With a little effort one can make something bigger fit."

"A little effort?" Lindsay said putting emphasis on the word effort. As said this she spotted Jake inside flirting. Bringing her eyes back to the handsome man in front of her Lindsay wishfully said, "B-I-G. Where is your accent from?"

"Australia and Senegal. My dad is from Senegal and my mom is a mix of Aborgine and Scottish," the man stated proudly. "As per effort," the man said, Deciding to ramp up the flirting he continued with, "and determination. Hold the target steady and push."

"You just line up the hole and push H-A-R-D," Lindsay said slowly and seductively.

"If you know what you are doing. And I know what I am doing," the man responded winking at Lindsay.

"So big genes, eh?" Lindsay asked noting his fingers were massive.

"I got my lighter skin from my Mom and my body from my Dad. My mom is from a tribe known for big features. She is Murri from Northern Queensland," the man replied.

"Queensland, that's in the north west. Good supply of natural resources with the rainforest and ocean. Good genes," LIndsay said as she looked the man over noticing his very large feet.

"You fancy my shoes?" the man asked.

Lindsay, blushing again, answered saying, "Yeah, they are nice. Skill is more important than size but I have never seen shoes that big."

"I wear a size 24. They are not easy to find," the man countered. Catching Lindsay's eyes he continued, "I am skilled at making sure the pain is more than made up for with pleasure."

"Oh, you do. Well, that is gracious of you to remain focussed on pleasure," Lindsay said flirtatiously. "Determination is a good quality."