Jenna Improvement Program

THIS IS A WORK OF FICTION!! ANY CHARACTERS OR EVENTS DEPICTED ARE FICTIONAL AND ALL CHARACTERS ARE OVER THE AGE OF 18.

This is my first crack at writing stories like these. The stories are heavily inspired by dlsloan and mchucha. The story has numerous chapters, so I'm trying just a few to start. There's a variety of themes explored, including: exhibitionism, voyeurism, reluctant sex, anal, bdsm, piercings, and piss, among others. I always liked descriptions of sexy outfits, so there's a heavier emphasis on that. The story is fictional and fairly unrealistic. Hope you enjoy!

Chapter 1

BEEP! BEEP! BEEP!

Jenna Trane blindly reached out to slam her hand down on her alarm clock. It was 6:30 am. She kicked the covers off her bed and groggily rolled onto her back. A large moisture stain on the ceiling stared down at the teen girl. She stared back as she tried to wake up.

It was midway through summer vacation and Jenna was determined to make a change. Yesterday had been her 18th birthday, and her senior year of high school was just around the corner. Up until now, school had been a nightmare for Jenna. Oh she did just fine in terms of academics. And she was a talented member of the gymnastics team's varsity squad. But Jenna's social life was in the toilet. She was regularly bullied, had never had a boyfriend, and aside from her single BFF, Maria, didn't have a friend to speak of. In fact, Maria was the only person that had come to Jenna's birthday celebration the night before, aside from her parents. They had sat on a couch together watching old re-runs of Friends. What a sad way to turn 18!

Jenna rubbed the sleep out of her eyes and jumped out of bed. All of that was going to change, starting today. She pulled out the sheet of paper wedged in the corner of her full length mirror. Sitting alone in her room the night before, at the end of what should have been the most important day of her young life, she had made a list. She was tired of being ashamed of how she looked. She was tired of being so timid in public. She was tired of nobody noticing her and having no friends. She was smart, she was athletic, and dammit, people were going to notice her! The list was short, and admittedly vague.

1. Improve self-image

2. Be more confident

3. Make at least two new friends

4. Get a boyfriend and have sex for the first time

Jenna uncapped purple pen and added "... not necessarily in that order" to item number 4. She dotted the 'I' in the word 'in' with a heart.

Number 4 was the real goal. Jenna really wanted to get laid, but knew she didn't stand a chance if she didn't make a change.

"Perfect!" She thought to herself. "It's time for the Jenna Improvement Sumer program to begin."

Jenna put the sheet of paper back in the corner of the mirror and began to remove her pajamas. Starting at the top button of her pink silk shirt, she slowly worked her way down. Jenna's self-image and confidence problems started with her physical appearance. Jenna had been a late bloomer, and even when she did bloom, it wasn't much. She was on the shorter side, 5'0", and thin as a rake. Her hips weren't very wide. Some of the guys at school described them as "boyish"... though she thought there was certainly enough to hold on to. In short, her body was a good body for gymnastics, but not necessarily for attracting boys at her school who were looking for "thicc" girls. Her favorite feature was her long, slightly curly red hair. It hung down her back to her small butt.

"My small but cute butt." She thought to herself. If she was going to improve her self-image, she had to start thinking more positively. And the hair was a good place to start. It fell down in rivulets, like a waterfall. When she arched her back, it created a gorgeous negative space between her spine and her hair. It was hair that models in Paris would be jealous of. Or at least she told herself that.

Of course, the genes that gave her such luxurious red hair also meant that her face and chest were spotted with freckles, which she hated. A sea of dots against otherwise alabaster white skin. She stared into her blue-green eyes in the mirror, then slowly worked her view down to her now exposed chest. Her breasts, like much of the rest of her, were on the smaller side, 32 A, with bright perky nipples set in the center of her breasts. They glimmered pink against her white skin, but were also small and she could easily entirely cover each nipple up with just two fingers.

"That'll make it easier when I wear pasties." She thought to herself sarcastically and smiled. Her smile revealed her teeth, shiny white pearls hidden behind pink-banded braces. She felt a little silly, having braces at 18. But her parents weren't very well off, and she had only recently saved up enough money from her work as a waitress to pay for her own orthodontia. In addition to the braces, she also had inter-arch rubber bands running from her upper canines to her lower back molars. The rubber bands were meant to reduce her slight overbite. Mostly, they just got in the way and contributed to her general dislike of her own look.

Jenna let the open shirt drop to the floor behind her and gently cupped each boob, watching herself in the mirror. Her pink nipples matched her pink braces. She gave each nipple a gentle pinch and tug. They stood erect. She had always had very sensitive nipples and enjoyed giving them some attention every once in a while.

That's right. She thought to herself. Focus on the parts of your body that you like. For a long time, she had thought that her white skin, red lips, and red hair made her look like the clown from the movie It. But she knew that was just her insecurity talking. When she was honest with herself, she actually looked quite a bit like Sophia Lillis from It, not the clown. The thought made her smile. Sophia was a hottie, and one of three people on her "I'd-go-gay-for-them" list (along with Scarlett Johansson and Shakira).

She tugged off her pajama shorts, revealing a wispy tuft of red pubic hair. Jenna didn't spend much time grooming her nether region, aside from trimming the occasional wayward hair in preparation for swimsuit season. But like her breasts, puberty hadn't bloomed so much as resignedly opened for her pubic hair. There was very little hair in need of trimming in the first place.

Aroused by her nipple pulls, Jenna decided to give herself a quickie to start the day off right. Despite her poor self image and low-confidence, Jenna had always been very sex positive. She was a virgin, sure, but that didn't mean she never touched herself! She enjoyed pleasuring herself with her fingers a couple of nights most weeks, usually while watching some softcore porn on her phone. She had even tried fingering her butthole once, though she hadn't quite seen the appeal.

Jenna cupped the mound of her vulva in her hands. Her outer labia almost entirely concealed her inner folds. This was the last part of her body that she liked. Her hair, her nipples, and her mound.

No roast beef curtains here. She thought to herself crudely. The dirty thought aroused her more. She slowly lifted her left hand up and across her body to message her right nipple. With the thumb and ring finger of her right hand, she parted her swelling lips. She caressed her middle finger up and down her moist vaginal opening before settling on her clit. Her clit was a little larger than she would have liked it, particularly when she was aroused. But it did make it easier to flick when she was in the mood. Her clit stiffened and began to poke out of its hood as she continued to work her middle finger over it in concentric circles. Jenna forced herself to keep watching herself in the mirror, focusing intently on the movement of her fingers on her now engorged, red clit. It was a little awkward, but she was trying to be more positive about her body, so it was important that she keep looking for the beauty in it.

Jenna felt her breathing get heavier as she got more into the groove. Bending slightly at the waist, she slipped her index finger inside herself. There was a soft squelch. She slowly worked her finger in and out while continuing to message her nipple.

Man, this positive body attitude seems to be working already. She thought as she listened to the sound of her finger working her now thoroughly wet pussy. Her left hand began to work more aggressively on her breast, pinching and pulling on her nipple. The white skin around her nipple had turned red from pinches. Jenna pulled her finger out of her snatch and went back to work on her clit. She was getting closer to climax and feared a moan might be coming. Worried that her parents might hear her she decided to try something new. Something to keep her mouth occupied. Something... a little naughty.

Keeping her eyes fixed on herself in the mirror, she worked her tongue around in her mouth, developing a ball of saliva. It was a more delicate procedure than she would have liked due her braces. Sticking her tongue out, she slowly let the saliva drip out of her mouth and onto her ravaged right nipple. A thin strand of spit connected her nipple to her outstretched tongue. Her fingers rubbed the saliva around on her breast, making it glisten and shine in the morning light. The sight of herself covered in her own drool, combined with the slight pain from her tweaked nipples and her furious clit rubbing had brought Jenna to the brink of explosion. She sped up the pace, furiously rubbing her crotch.

"Hey Jenna, are you awa..." Just as Jenna was about to cum, her door burst open. Jenna dove behind her bed as if she were in a duck and cover drill.

"Can't you knock?!" She screamed furiously at her father. "I was doing my morning... affirmation." She explained lamely. Jenna had hidden quickly enough, so she hoped there was still a possibility that her father hadn't seen her furiously masturbating in front of her own reflection.

"I'm sorry, darling," her father apologized. He pulled the door slightly shut and averted his gaze, but stayed in the doorway. "I wanted to make sure you didn't oversleep. Remember you've got an orthodontist appointment this morning. I know how hard you've been working to afford your braces, so I wanted to make sure you didn't miss it."

Still hunched over behind the bed, Jenna's knees pressed painfully into her breasts. Her right tit was still covered in spit and her crotch was leaking all over her ankles and the floor. She looked around desperately for something to wipe up with, but couldn't find anything nearby. With her father still standing in the doorway, she didn't dare get up to find a towel. Looking down, she saw her long red hair draped around her. She grabbed her hair, bunching the end together to make a makeshift sponge, and quickly wiped up her chest and between her legs. The end of her hair was matted together, covered in her own juices. It was gross, but it would have to do for now.

"I know dad, I wouldn't forget something like that!" She shouted impatiently. Jenna loved her father, but he had a way of not respecting boundaries. In his mind, she was still his little girl, not an 18 year old woman. Besides, her teeth had been one of her major insecurities. Did he really think she would forget? And the more he just waited in the doorway, the more likely it would be that she'd be late.

"Just go away dad, I need to get ready!"

"Hey, what are you doing crouching behind the bed there?" Her dad asked inquisitively. He took a step into the room and began to peer over the edge of the bed.

"Dad!!!" Jenna screeched. She was mortified, but at least this meant that her dad hadn't noticed she was naked... or masturbating. "Get out of here will you?!" To punctuate her request, she lobbed a nearby Vans shoe at her dad's head. He ducked and stepped back from the bed.

"Okay, okay!" Her dad backed out the door, closing it behind him. Sheesh, the girl turns 18 and becomes totally temperamental and crazy. He thought to himself. I hope I'm not going to have to have a talk with her...

Jenna stood up, still stark naked, and checked her clock. It was already ten to 7. Normally, that would be plenty of time to make it to a 7:30 appointment, but she suspected it was going to take longer to get ready this morning. Certainly not enough time to finish herself off. Although she was still incredibly horny, it looked like her window had passed.

Reaching under her bed, Jenna grabbed the Amazon package that had arrived for her yesterday. As part of her reinvention, she had bought some new clothes. A new look for new Jenna.

Jenna had never put much effort into her appearance. As a gymnast, she received a lot of free clothes at competitions. So she mostly wore gym shorts, t-shirts, and hoodies. Since she had never thought she had much of a figure, she hadn't thought she had much to show off, so baggy hoodies had done the job. So it seemed to her that a new wardrobe was a crucial element on her journey to to lose her virginity. She gripped a pair of scissors from her bedside drawer, slit open the box, and began to pull the contents out.

CHAPTER 2

First out of the box was the top. It was a cold shoulder crop top made of yellow chiffon with a slight floral pattern. Jenna pulled it over her head. The top had a frilly band of yellow that went across her petite breasts. Below her breasts, the top billowed slightly, making it look almost like a babydoll blouse. But the short cut made it clear it was a crop, leaving her belly button exposed. Jenna spun a quick circle and the breezy portion of the top lifted up, revealing her stomach all the way up to the base of her breasts. Standing still, the top settled back down, but still left about an inch above her belly button visible. The exposed skin was part of why she had selected the top, but wearing it now she felt awfully exposed.

Too used to wearing hoodies, I guess. She thought to herself. It also didn't help that she was still naked from the waist down. The small wisp of delicate red pubic hair was a little loud next to the yellow of the shirt.

A thin spaghetti strap ran over each shoulder. Jenna had made sure that she got one with straps for fear that her small bust wouldn't be able to hold up a tube top. Small sleeves cold shoulder sleeves covered her lower biceps but leaving her shoulders and upper arms fully exposed. The shirt was slightly too small and Jenna could clearly see outline of her nipples through the tight band across her chest. She pulled the shirt off, quickly threw on a thin wireless bra, and pulled the shirt back over. The blue bralette straps were small, but still showed next to the the thinner spaghetti straps of the yellow top. It wasn't perfect, but she guessed it would have to do for now.

Next out of the box was a choker necklace. It was a small gold chain covered in white plastic flowers. Jenna pulled the necklace snugly around her neck, closing the clasp at the nape of her neck. Although it was a choker, it was designed with a little extra chain to dangle down an extra six inches along her spine.

Reaching next into the box, Jenna pulled out her most daring purchase: a deep royal blue thong. It wasn't quite a G-string, but it was skinnier then some of the other thongs she had considered. And as her first thong, it felt particularly risqué. She stepped into it and pulled it all the way up. The material slid snugly between her asscheeks. Her initial urge was to pull it out like a wedgie, but she reminded herself this is what it was supposed to feel like. She carefully adjusted the small triangle of blue material on the front of her mound. Luckily, she had gotten the sizing about right on this purchase. Her pubic hair was already trying to poke out of the top. Any lower cut and the top of her slit would have been visible.

These aren't your old Eeyore cotton panties. The thong made her feel sexy.

She then grabbed a pair of jean shorts out of the box. Holding them up, she was disappointed to find they weren't as cute as she had hoped. They were straight legged and would reach down to her knees.

I think I can fix this. Jenna thought to herself as she reached for the scissors. She carefully cut the jean shorts, starting at the in seam and working her way. She turned the angle of the scissors as she neared the crouch and cut diagonally up just below the pockets. This will allow just a bit of my butt to stick out the bottom, she thought to herself. She finished cutting around the front of the shorts, taking a good 8 or 9 inches off the length of the shorts. Satisfied, she held them up for one last look, then pulled them on. She quickly became dissatisfied.

Oh no! She thought, I've cut off way too much! She spun around to look at her rear end. There wasn't just a little bit of butt showing... there was a WHOLE lot of cheek. Furious with herself, she spun back around to check out the front.

I should have tried these on before I started cutting, she thought to herself furiously. They were much lower in the front than she had expected, rising just above the front of her royal blue thong. Combined with the crop top, there was a much larger expanse of flesh from her mound to well above her belly button showing more than she had planned. Worse, the thong was cut in such a way that the straps were clearly visible above the top of the low-cut shorts, and she had a prominent whale-tail showing in the back. If her goal was to look confident and chic, she had failed. Whale-tails went out of fashion in the mid-2000s!

Unfortunately, Jenna didn't have a backup plan. With all of the money going to orthodontia, she hadn't had much left to spend on clothes. It was these shorts or old gym shorts again.

New Jenna doesn't give up that easily, she swore to herself. She was prepared to be seen in public with much less on above and below than she had planned. I mean... it was revealing... but not yet anything that would be viewed as totally unacceptable. There were a few girls at her school that wore less.

Jenna reached into the box to grab the pair of brown ballet flats she had purchased to close out the ensemble. She looked down at her feet. It had been a while since she had last done her nails. There were the remains of pink nail polish, chipped and fading on her toe nails. Luckily no one needs to see that, she thought to herself as she pulled on the flats. The flats fit perfectly. They left a nice bit of toe cleavage peaking over the top.

Jenna gave herself one final inspection. It wasn't perfect, but she thought she looked pretty cute in her tight yellow top, choker, skimpy shorts, and brown flats. She adjusted the straps on her thong slight, sending a quick shiver through her body as the shred of fabric in the front rubbed against her pussy. She was still extremely turned on. Looking at the clock, she saw it was already five after 7, and she would have to hurry if she hoped to make it to her appointment on time. She quickly put on some simple makeup: reddish lipstick, a little eye shadow, and a slight amount of blush to giver her face a healthy look. She grabbed a scrunchy and a pair of stud earrings off her dresser as she opened the door to leaver her room. Luckily, there was no sight of her father so she wouldn't have to find out how much he had actually seen this morning.

Walking down the stairs, Jenna pulled her hair up into the scrunchy. It was a big one, creating a ponytail that extended about 4 inches from the crown of her head in the back. The rest of her long red hair cascaded out of the tight scrunchy and down her back. The pony-tail allowed enough space to make the chain dangling down her back from the choker visible, but still left her hair long enough to extend below the top of her short shorts. If she had wanted to, she could tuck her fiery hair into the waist-band of her shorts. Jenna clipped in her earrings as she approached the kitchen. She wore simple gold studs that were shaped like little roses. She had always wanted to get her ears double pierced. Jenna thought piercings like that were sexy. But the cost, and fear of her father's disapproval, had prevented her from taking the plunge.