The Sexiest Cheerleader

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Explicit Content (Reader Discretion Advised)

"The Sexiest Cheerleader"
A "Timber Grove" Story
by TGTrinity


///// 1
///// "Becoming Leslie"
///// Sunday Morning


Seth knew that he was not going to get out of this. All he could do was sit in the back of the SUV and look at the small glass flask in his hands as his teammates rambled on and on about what he was supposed to do. As they argued with each other, he thought about the game the other night and wished that there was someway to go back in time...

"Fuck, Seth, are you even listening?"

He looked up to see his teammate, Marcus, looking at him as intensely as possible. "Yeah..."

"Okay, then tell me what you're going to do."

"I'm... I'm going to retrieve the playbook from Timber Grove Community's Head Coach."

"And how are you going to do that?" another teammate in the car asked.

"I'm going to... I'm going to live with the coach's family..."

This made some of the guys in the car laugh, which made Marcus upset. "Shut the fuck up! You want to fucking do this instead of Seth?" Both guys quickly shook their heads and stopped laughing. "Go ahead, Seth."

"I'm going to get the playbook and give it to you guys before the game on Saturday night."

Marcus smiled at Seth and put his hand on his shoulder, though the situation felt anything but friendly. "You've got this Seth. It's only seven days, and then everything will be back to normal."

The flask in Seth's hands began to heat ever so slightly as he gripped it tighter. "Come on, guys... There's got to be another way."

"You cost us the fucking game last week, Seth. You don't fumble on the one yard line and we're a lock to go to the Championship, but now we have to beat fucking Timber Grove Community!"

"Yeah," another random teammate added, "and they're tough as shit to beat."

"He's right," Marcus added before continuing, "and getting that playbook is the only way we can guarantee a spot in that Championship game. So you're either going to drink that stuff on your own, or we're going to force it down your fucking throat."

Everything after that comment Marcus made was hazy, and as Seth opened his eyes he could tell that something was different. He was no longer in the back of the SUV, and all his teammates were gone. Instead he found himself in a room with light green walls and various pictures hanging up everywhere. There was a white desk on one side of the room, while a large dresser sat opposite it. Seth looked at the pictures hanging, most containing girls in cheerleader uniforms practicing, performing at games and doing assemblies.

Seth then stood up and walked over to the closet. The haze was dispersing, but it still felt like he was missing something. As he passed a large stand alone mirror, he finally remembered everything.

In the mirror Seth saw a very petite girl with blonde hair. She was cute in a plain sort of way, with a t-shirt on and a pair of flannel pajama bottoms. As Seth raised his hand, the girl in the mirror did as well. When Seth reluctantly approached the mirror, the young girl followed suit.

"Oh my God..." Seth ran her new hands over her body, making sure that she wasn't just seeing things. "Oh my God!" Her new voice was a soft soprano, and as the haze finally dissipated she finally came to terms with her situation. She sat on the edge of the bed and took a few deep breaths before trying to speak again. In her mind she knew that she was Seth, but she knew she had to speak the words...

"My name is Seh..." She paused, choking on the words as they came out. "My name is Seheee..." Her name was Seth, yet another name was quickly bubbling to the surface of her mind. "My... name... is Leslie..."

Seth had been informed by the woman who had given them the flask that drinking it would allow him to "enter" someone and take on their identity. This also included their emotions and memories, but it was still Seth inside the little female body.

Even though she knew she was still Seth, she knew her new name was Leslie Dwyer. She was living with the Perkins while she attended Timber Grove Community College, which is why the team picked her as their target. She was nineteen, although she looked much younger, and was on the Varsity Cheerleader squad at the school. Her best friend Ann was the Captain, and lived in the room right next to her.

"Oh shit," Leslie said, as more and more memories filled her head. She felt like she was about to throw up when the door opened.

"Hey, Leslie," Ann said as she entered the room, wearing only her bra and panties. Leslie felt like her nausea get replaced with another feeling, and she was glad for it. Whereas Leslie was rather plain looking, Ann was the pinnacle of feminine perfection. Full breasts were straining against her bra, while long, toned legs led up to an ass that bounced ever so slightly with each little step. A small scrunchy held her long brown hair in a playful ponytail... and Leslie felt like she was in love.

"God, what's wrong with you?" Ann asked as she hopped on Leslie's bed.

"I, um, just feel a little... different."

"Well you certainly look the same," Ann said with a laugh.

Leslie tried to push aside the irony of the comment and thought about what to say, which was hard to do with Ann checking her phone on the bed. "No, I mean... Never mind..."

"God, that guy I hooked up with last night at Tribal won't take a hint," Ann said as she swiped left and right on her phone, "I mean, he was fun a little bit..." She then prattled on about how she was sick of guys constantly hitting on her, and Leslie just let her talk. The weirdness of being in a girls body was being marginalized as Leslie ran her eyes over Ann's long legs,her firm stomach and those massive...

"God, are you really okay?" Ann had a look on her face that told Leslie she wasn't mad, just more concerned that her friend seemed to be staring at her.

"I fell asleep and just woke up a little groggy, that's all..."

Ann smiled and Leslie felt her knees almost give out, "Good, I don't need one of my best girls getting sick a week before we play Sandy Shoals..." Of course Ann had no idea that her friend Leslie was currently playing host to a guy who was a back up running back for  Sandy Shoals Community.

"Really, I'm fine," Leslie said with a smile.

"Great! My parents will be home soon so you should probably get dressed, so they don't think you slept all day!" She got up and threw a pillow at Leslie who caught it and smiled.

"Hey! I'm not the one walking around showing off for the neighborhood!"

"Well, if you've got it," she added with another smile and Leslie almost lost it. As Ann walked out of the room, Leslie admired her ass swaying compellingly one last time. When she was finally alone, she locked the door and laid on her bed.

"Oh my God!" She screamed before grabbing a pillow and screaming into it. As Seth, she had known for a few days that she was going to be "Leslie", and she thought being around someone as attractive as Ann would be easy as a girl. No one could have guessed that the real Leslie had feelings for Ann that certainly went far beyond friendly, and now all of those feelings were hitting Seth hard.

There was a clock on the wall, and Leslie could see that it was 3:30 in the afternoon. She knew that there was one thing she had to do before continuing with the day, something that would help add some normalcy to her situation. She looked around and found some flip flops that she put on before walking out of her room.

The Perkins house was two stories, and looked rather new. Family pictures hung in the upstairs hallway where Ann and her rooms were, showing mostly pictures of Ann and her mother. Leslie knew that Ann's mother had passed away four years prior, and her Dad had married a woman that Ann was not particularly fond of.

Leslie made her way downstairs and out the front door. It was a typical fall day in Timber Grove, with gray skies and a slight breeze. Leslie felt the new sensation of her little nipples hardening as a breeze whipped up around her, but she tried to ignore the pleasing feeling and focused on getting to the mail box.

She held her arms around her as she approached the box, thinking she probably should have grabbed a jacket. For a moment she wondered if the box would be empty, that all of this was an elaborate prank her teammates had come up with to punish her for losing the game. To her relief, she opened the box and found a phone inside. She powered it on and entered the pass code, then saw that there was one text message on the phone. She read it quickly before typing a response.

"Yes. I'm in."

///// 2
///// "An After Dinner Treat"
///// Sunday Afternoon

Leslie closed her bedroom door behind her and locked it to make sure she was not going to be interrupted again. She took the phone that she had retrieved from the mail box and hid it in the top drawer of her dresser. As she did, she noticed all of the bras and panties that were in the drawer. As she picked a particularly cute pair up to examine them, she thought of what she had often done as a boy to relieve some stress.

"No... I can't..."

She slowly closed the drawer and sat on her bed, trying to shake the thought from her head. She tried to focus on how she was going to get through the next week as a girl, especially living next door to one of the sexiest girls she had ever laid eyes on.

Thinking of Ann again was taking her down that familiar path again, so she bit her lip and tried to think of something else. Thoughts beside those involving the leggy brunette next door were now flowing into her mind. Knowing that she had to be Leslie for a week, she tried to access her memories and find out more about her.

There were glimpses of Leslie at College, practicing with the cheer squad and living with the Perkins. Jumbled in with all the memories were thoughts of Ann, stolen glances and playful fights on her bed. There were also thoughts that lingered on Ann's stepmother, but Leslie tried to focus on important information. Scenes played in her mind involving all of these things, including a lot of time spent with a guy named Ron, yet she couldn't think back to anything that happened to her past a year ago. Still, there was plenty of good knowledge there, and when Leslie heard a knock at the door she was shocked to find that she had been lying on the bed thinking for over an hour.

"Leslie? It's time to eat, girl!" It was Ann, and Leslie remembered what she had said about getting dressed.

"Give me a sec!" She yelled as she got off the bed. There was no response, so she figured that Ann had gone downstairs to be with her parents. Soon she was in front of the mirror again, still in the t-shirt and flannel pajamas she was in earlier. It was the moment she was dreading, yet she knew that sooner or later she was going to have to get naked, and now seemed to be that time.

After a deep breath, Leslie closed her eyes and pulled the t-shirt over her head. For a moment she stood there in silence, then she opened her eyes and looked into the mirror. Leslie breasts were small with tiny pink nipples. She pulled from her memory that they were only a cups, but she knew that she wasn't in this body to...

She paused at the thought, thinking back to what her teammates had said before: "Whatever it takes..."

Feeling that she had already gotten over a fairly large hurdle, she quickly stepped out of her flannel pajamas and was now only wearing a tiny white pair of panties. She turned and was somewhat pleased to see a plump little behind on her. She wiggled her hips in the mirror a little bit, a tiny smile crossing her lips as she playfully shook her ass.

She was feeling rather good about herself, and she soon had her panties down around her ankles without even thinking about it. Her ass was smooth, and as she ran her hand over it, she couldn't help but think about that last thing...

As a man, Leslie had been with a few girls, yet she was never fortunate to get far enough with any of them to see what she was looking at now. Her vagina was surrounded by trim, blonde hair with tiny folds tightly held together. She had of course seen one many times before online, but this was the first time she had seen one in person. Her hand was cautiously grazing her inner thigh, and she could begin to feel her heart beating faster...

"LESLIE!!!" It was Ann screaming from downstairs, and it snapped her back into attention. Instinctively she opened her closet and grabbed a pair of jeans and a light blue polo. She had no problem getting a pair of baggy jeans on, but struggled to pull the tight polo on.

Without another thought she was out her door and bounding down the stairs. It was much cooler downstairs than it was in her room, but it was too late now to go back and grab something. She turned a corner and saw Ann in the kitchen with her parents. Her father, the target in this entire fiasco, was a very handsome man in his early forties. He was fit with a little gray creeping in around his ears, with the rest of his brown hair full and cut short. All things considered, the family resemblance between he and his daughter was fairly evident.

April, Ann's stepmother, on the other hand stuck out like a sore thumb. She was probably in her mid twenties, with cinnamon skin that hinted at a Polynesian heritage and black hair fell straight down her back. There was no question that she was gorgeous, with a pair of tits that gave Ann a run for her money, yet she carried herself in a very different way than Jerry and Ann.

None of this was more evident than when they were sitting around the small table in the dining room sharing a meal. While Jerry and Ann made jokes and feigned arguments, April sat staring at Leslie like a hawk.

"The pasta is delicious, thank you." Leslie said to Jerry.

"Ah, don't thank me, you have April to thank for that."

"Thanks, April," Leslie said with a smile, yet April just nodded her head as she continued to eat. The situation made Leslie a little uncomfortable, so she chose to try and finish the meal as soon as possible.

Soon the meal was done, and Leslie was more than happy that she got through it without anyone noticing that she really wasn't Leslie.

"Ann and I will take care of the dishes, so can you clear the table with April?" Jerry asked as he walked around the small bar separating the kitchen from the dining area.

"Of course," Leslie said, her soft soprano sounding very happy and care free. She began to stack some dishes when April made her way around the table. She was wearing a pair of jeans and a white knit sweater with a scoop neck, and she sidled right next to Leslie as she reached for the pot of pasta.

"You're not wearing any panties, are you?"

Leslie didn't know what to say. Of course she had forgot to put on any underwear, and now Ann's stepmother was calling her on it. "Oh, I forgot..."

April smiled and looked into the kitchen to see Ann and her father working on the dishes. "Did you forget for me?"

What happened next froze Leslie in place. April had taken her left hand and had slid it down Leslie's jeans. "Oh my God, what..."

"Shh, shh," April whispered in her ear. He hand then slowly moved deeper down her pants, until a finger was right at her new feminine opening. Leslie, of course, was only seconds away from exploring her sex earlier in her room, but she had no idea that Ann's stepmother would be the first to touch it.

"Your husband is, oh!" Leslie felt April's finger enter her, and soon felt herself begin to moisten down there in response.

Ann peaked out around the corner, "Is something wrong?"

"No, she just dropped a cup," April said with a smile as her finger worked inside of Leslie.

"Oh, alright," Ann said, failing to notice that her stepmother was currently inside of her friend.

Once left alone, April continued to work her finger inside of Leslie. Each flick made Leslie's heart race faster, and she found herself gripping the table for support. She wanted to leave the table, or call for Ann, but found she was at the mercy of this stunning creature beside her. Leslie soon felt something bubbling up inside of her, but the feeling was cut short as Jerry rounded the bar and April freed her hand from Leslie's jeans.

"Jesus, you two are certainly taking your time," Jerry said with a laugh.

"Ah, we are just having a little girl time in here," April added before taking the pot of pasta into the kitchen. Leslie said nothing, her hands still gripping the table, and as she looked over into the kitchen she saw April lock eyes with her before licking her finger. "God, that was delicious," she said with a wicked smile.

"It sure was, honey," Jerry said, completely oblivious to the situation.

"I'm not feeling great..." Leslie said before freeing her hands from the table and running up the stairs. She softly closed the door behind her and locked it before lying on her bed. She had just been fingered by her best friend's stepmother, and instead of guilt she was feeling something else. She couldn't quite put a finger on it, but soon she knew what she was feeling.

She was feeling a need she had felt many times as a boy...

The need for release.

///// 3
///// "A Little Peeking"
///// Sunday Evening

The need was building inside of her, but she was still reeling from what happened downstairs. Part of her felt violated, but the another part of her felt sheer exhilaration at the feeling of having April's finger inside of her. She couldn't decide if the simple act of being felt up was turning her on, or if it was the thrill of doing it right where Ann and her father could see her.

Worse still., she couldn't come to terms with what part of her was driving these feelings. Was this something that April had done with Leslie before, or was this Seth letting his dormant needs come to the surface?

As she slid off the bed, she undid her jeans and allowed them to fall to the floor. Her polo soon followed, and she was now standing naked in front of the mirror again. Her petite body was covered in tiny beads of sweat, and the tiny nipples on her modest breasts were erect and begging for attention.

But Leslie was at a loss as to what she was doing. She wanted to distance herself from what was really happening, to write it all off as some sort of dream or fantasy. Of course, that would make everything she was doing so much easier. If this was a dream, then she could do anything with Leslie's body and just snap out of it like nothing happened. Exploring everything a woman could do, experience and feel is something that intrigued her, but this wasn't her body. Leslie was a real girl with a real life, and even though Seth was in control of her right now it didn't change the fact that he was only in her body for a week.

She didn't like the feeling of guilt mingling with her still rising arousal, and for a moment she felt she had regained enough control to slip into some pajamas and go to bed early...

But then she heard something.

"I'm gonna take a quick shower," Ann said through the bathroom door.

"Alright," Leslie said, not knowing that her bedroom shared a bathroom with Ann. She crept closer to the door, still completely naked, and waited by it. Ann had put on some music, and soon Leslie could her the shower running.

The guilt that she had felt just by looking at Leslie's naked body was now centered on the thoughts she had of opening the door just a crack. She heard a gasp and backed slightly away from the door, until she realized that it had escaped her own mouth. Her hand had slipped between her legs on it's own accord, and her finger was tracing her moistened slit.

It was incredible, even more so than before in the dining room. It felt like every inch of her skin was rippling, as hairs stood on end and goosebumps crossed over her body. She dropped to her knees as the feelings became too much, and found that her other hand had found her breasts. No matter their small size, they felt incredible. She thought of how much better they would feel if they were as big as Ann's, and then she remembered why she was hunched over by her bathroom door.

With any sense of guilt or apprehension washed away by a blissful disregard, Leslie slowly cracked the door of the bathroom open and looked inside. She was displeased to find the shower was on the other side of the bathroom, but then she gasped a little as she looked in the mirror. A perfect reflection of Ann was washing herself in the shower. Leslie couldn't see her lower half, but what she could see was impressive.

Ann's tits held the same shape they had in her bra, an impressive feet given their size. As she ran her soapy hands ran over them, Leslie couldn't help herself and stuck her middle inside of her slit. Her back arched as little jolts of electricity fluttered over her body. It was more intense than masturbating as a man had ever felt, and that was only with her one finger.

Movement came naturally, and Leslie soon found a good rhythm. She was pushed on by the sight of her friend washing herself, and the sight of the greatest pair of tits she had ever seen. Ann certainly seemed to enjoy her tits as well, as her hands cupped, squeezed and massaged them.

"Ah..." Leslie let a soft moan escape her lips, but was relieved to see that Ann hadn't noticed. Her finger was sliding in and out of her with ease, and soon she reached a spot that made her bite her lower lip as a wave of pleasure began to cascade inside of her. She rode it for as long as she could, then felt it crash down over her with amazing force.

"Oh! Oh!"

Leslie was so shocked by her first orgasm as a woman, that she had taken her eyes off of Ann who was clearly getting herself off as well. One of her hands was pinching her nipple as the other was either inside of her or thrusting something else into her sex. Either way, Ann was definitely enjoying herself and was not holding back.

"Oh, fuck! Yes! OH! OH! YES!"

Ann's cries of passion had spurred Leslie on for a second time, and she found herself soon riding that wave she had just rode before. Even at a time like this, she was amazed that she was able to feel as good as she did so soon after cumming earlier.

"Oh my God! Oh my GOD! YES!"

Leslie muffled a moan as she felt another orgasm shake her body the same time Ann experienced hers. It was more electric than the first, as the knowledge that she was getting off the same time as her beautiful friend was an incredible turn on.

Ann was slouched against the back of the shower now, fighting to keep her breath, and Leslie felt that was as good as time as any to slowly close the door. For a moment she felt Ann look in her direction as she closed the door, but she didn't wait to find out and was soon back on her bed with the door closed behind her.

Her body, once covered in tiny beads of sweat, was now covered in a sweat. Her breathing was still labored, but she felt better than she had in a long time. Her hand was soaked from her activity, and as she licked her finger clean she suddenly realized what she was doing. Not once as a man had she ever had to urge to taste her cum, yet she had willingly tasted herself and found it to be incredible. The thought of how naughty she was being made her want to try for a third time, but she soon heard the phone she had stashed earlier begin to vibrate in her dresser.

She got up and retrieved the phone, finding a new text message from her teammates.

"Update?"

Before responding to the update, she grabbed a tissue from her dresser and cleaned herself up. She then slipped into a pair of panties and sat on the bed.

"I'm in... Had dinner with family..."

"Good... Do whatever it takes to obtain Playbook..."

She sat on the bed for a moment, pondering what was inferred in the last text. Even though she had just cum twice while watching her friend shower, she couldn't imagine doing what the teammate was clearly alluding to. She had always just planned on getting information and then using her status as a cheerleader to sneak in and get the book. There were obviously easier ways to accomplish the same goal, but she knew that becoming a girl and doing it herself was a way to gain back the trust of her teammates.

"Understood..."

After locking her phone and hiding it back in the dresser, Leslie felt a wave of sleepiness pass over her. She thought for a moment that she should put a bra or shirt on, but felt that her tiny tits would not cause her too much discomfort in the night. With her soft bedding pulled around her, Leslie fell into a deep sleep, dreaming of the week ahead of her.

As she silently rested on her bed, the phone in her dresser vibrated softly. In the morning it would have a message waiting for her, and not one from her teammates. It would come from an unknown contact, but the words contained in it would make her week a tad more difficult:

"I know you're not Leslie."

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  1. when I click on "continue to day 2" I get PAGE NOT FOUND??????

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