Jenna Improvement Program Ch. 01

Jenna grabbed a Pop Tart as she walked into the kitchen. Her dad, Ronald Trane, sat at the table munching on a bowl of Total. He raised an eyebrow at the sight of his teenaged daughter. It was without a doubt the most provocative outfit he had ever seen her in. Ronald and his daughter had gotten along pretty well for most of her life. Jenna's mom worked as an investment banker, so she wasn't around very often. Jenna had one older brother, Gary, but he was in the Navy and on deployment. That meant father and daughter had a lot of time just the two of them. Ronald thought he had done a pretty good job raising his daughter mostly alone. She got good grades and was active on the gymnastics team. She didn't have a lot of friends, he thought, but she did seem to get along well with her teammate, Maria. And fewer friends meant he got to spend more quality time with her. They liked to watch cheesy horror movies together on the weekends. Sometimes, they'd snuggle up on the couch for movie marathons, binge watching 80s slasher flicks or every Alien film.

Recently, though, Ronald felt like his daughter had been growing away from him. This morning was a perfect example. She had exploded on him for no apparent reason that he could discern. Now she was wearing this ridiculous outfit. Ronald supposed the skimpy cutoffs were in fashion right now. But it made him a little uncomfortable to see his own daughter in them. His little girl was growing up. Despite his reservations, Ronald decided to try to be supportive.

"Sorry about barging in this morning. That's a neat outfit you're wearing."

Jenna rolled her eyes. She couldn't believe her father had called her outfit "neat". Plus, she didn't want to acknowledge that her father had almost caught her masturbating. She sat down silently and took a bite of the Pop Tart.

"Is it a special occasion?" He tried again to connect with his daughter. He secretly hoped she was dressed up for a date. Despite her successes in the classroom and in the gym, Jenna had still not shown any interests in boys. Or girls for that matter. Part of Ronald was glad. He hadn't had to have an awkward "Talk" with his daughter yet. On the other hand, he was a little worried that she was 18 and, as far as he knew, had shown no interest in romantic relationships.

"Just trying something new." Jenna replied simply. His question had the opposite effect he had hoped for. He couldn't have known that Jenna was also worried about the lack of romance in her life. But it certainly wasn't something she wanted to talk about. For her part, Jenna definitely still loved her father, but she also had felt the distance growing between them. She liked movie nights just fine, but she had increasingly found that she didn't have much to talk to her father about. Ronald only wanted to talk about movies and kid stuff. She needed someone she could talk about boys with and share fashion ideas with. You know, "girl" stuff. I mean, how was she supposed to talk to her dad about wanting to lose her virginity? It just wasn't the kind o f relationship they had. Jenna finished her Pop Tart and got up without saying goodbye.

"I love you!" Ronald called out as she made her way into the garage. Rekindling his relationship with his daughter would have to wait for another time.

Jenna drove an old stick shift Honda Accord. It was a bucket of bolts, but got the job done, and she had a strange affinity for it. Something about the fact that she was the only one of her friends and family that knew how to drive stick made her feel special. She jumped in the car and drove to her appointment.

Jenna walked into the office with 5 minutes to spare. Sammy, Dr. Truce's assistant, greeted her.

"Dr. Truce will be with you in a moment, just follow me back to your chair." Sammy said cheerfully. Sammy had brunette hair cut into a tomboy pixie haircut. She wore green scrubs, but her giant rack was still evident below the loose clothes. The low V-neck gave Jenna a clear view of Sammy's cleavage. Jenna couldn't help herself but stare enviously at Sammy's well-endowed chest. Sammy turned and led Jenna down the hall to an empty chair. Jenna watched Sammy's ass wiggle back and forth in the surgical scrubs as she led the way.

I definitely should have finished jerking off this morning. Jenna thought to herself. I'm even lusting after the assistant!

Jenna laid back in the orthodontist chair as Sammy attached a paper bib around her neck. Janna felt her bared ass cheeks rub against her long red hair beneath her. She gather up her hair and pulled it to one side, allowing it to fall to the ground. It didn't help. Now all she felt was the vinyl of the chair sticking to her butt. She sighed, then she crossed her ankles and waited patiently for Dr. Truce to arrive.

"Good morning, Jenna. Wow, you look amazing today." Dr. Truce walked into the cubicle and sat on the roller chair next to Jenna. "I've never seen you so... fashionable." Dr. Truce's eyes moved hungrily over Jenna's body. Jenna felt initially uncomfortable. She moved to claps her hands in front of her to try to cover up some of the bar upper thigh on display for Dr. Truce. Biting her lip, she forced herself to place her hands at her sides and let him enjoy the view. Confident girls aren't embarrassed by their bodies, she thought.

Dr. Thaddeus Truce was much cooler than his name suggested. He was young for a doctor, in his late 20s. Jenna had always felt an affinity for him. She spent most of each appointment with his fingers stuffed in her mouth, but she had always still down a way to talk with him. Plus... she had to admit she thought it was kind of hot when he put his fingers down her throat. It also helped that Dr. Truce had been a tattoo artist before becoming an orthodontist. He had colorful sleeve tattoos up both arms that Jenna could see when he rolled up his sleeves. His hair was blond and swooped down into one, deep brown eye when he lectured her on braces maintenance. In short, Dr. Truce was a snack.

"Hello Dr. Truce. It's nice to see you." Jenna said in a sing song voice. Inside, she was jumping for joy. He'd noticed her new outfit!

"What's the special occasion, you don't normally dress this... forwardly."

"Oh, um... I'm just trying to dress with a little more confidence." Jenna replied.

Dr. Truce rolled up his sleeves, revealing his muscular, inked forearms. Jenna bit her lip and resisted the urge to touch herself.

"Well you should be confident! You're a beautiful young woman. Open wide." Dr. Truce continued to talk as he proceeded with the appointment. "I used to suffer from low confidence too. That's part of why I got into tattoos. I wanted to make myself a work of art. But then, I realized that I was thinking about things all wrong. If I want to be more confident, I shouldn't bend myself to try to impress other people. What I needed to do was not care about what other people think. I started putting myself in the most humiliating circumstances I could imagine. If I can be comfortable in those circumstances, I figured I could handle anything. In fact, that's why I got this." Dr. Truce pointed to his right forearm. Jenna raised her head slightly to see his pink unicorn tattoo. She had noticed the tattoo before, but this was the first time that she realized how well-endowed the unicorn was. And the fact that it was taking a gigantic piss. She had to admit that it was a pretty embarrassing tattoo, especially for a practicing orthodontist.

Dr. Truce could see the reaction in Jenna's eyes. "Of course, I could try to get it removed. But if I'm worried about what people think, then I've already lost. So I keep it as a challenge. A way to say 'Fuck the world, I'm going to be me and not care what other people think.' That's where confidence comes from." Dr. Truce paused his examination of Jenna's mouth as he finished. She could see her saliva coating his fingers as he removed his fingers. She found herself oddly missing the feel of his hands in her mouth.

"That... actually makes a lot of sense. I guess I'm trying the same thing." Jenna replied.

"I wondered. I've never seen you wear an outfit like that." Dr. Truce wiped his damp fingers on the napkin clamped around Jenna's neck. The feeling of this young stud's fingers caressing her breast, even if through a paper bib, reminded Jenna of how turned on she was by her orthodontist.

"Yeah. I guess it's just me trying to find my confidence. I'd love to go further, like maybe get some more piercings or something, but I think I should take it one step at a time."

"I hear that. I've got some piercings myself. I could probably hook you up if you're interested. What colors are we doing today?"

The question snapped Jenna out of her daydream imagining where Dr. Truce's piercings might be. There were no obviously visibly piercings, as far as she could see. Maybe on his big cock? She thought to herself, biting her lip. Of course, she would never say that sort of thing out loud. Every time Jenna tried to talk dirty, it just sounded silly to her when it came out. Focus Jenna, answer the question, she scolded herself.

"Colors?"

"For your replacement bands."

Jenna always struggled with picking colors for her braces bands. What colors said "New Jenna"? The answer was obvious. "New Jenna" was cool and confident. Cool and confident people don't have braces in the first place! But since she was doomed to wear braces, she figured she might as well pick a color.

"Oh, um, I guess I'll try yellow and blue."

"Good choice. I'll be right back." Dr. Truce. Stood up to get the new band colors. Jenna watched him leave the room. One of the nice things about orthodontists is that their white coats only go down to the waist. Jenna enjoyed the view of Dr. Truce's tight trousers as he left the room. Once he was out of view, Jenna's hand immediately shot down to her twat. The denim was a little tight, and she didn't dare unbutton her pants in a public place like this. But the zipper on the crotch of the shorts was already giving her a prominent camel toe. And the blue thong's material was thin, practically sheer. She rubbed the zipper through the material against her clit. She closed her eyes and leaned her head back, alternating thoughts of Dr. Truce's cute butt and Sammy's pixie cut. It was the first time she had ever included a woman in her fantasies. But then again, Sammy was pretty androgynous, so Jenna figured it didn't count.

"I couldn't find the exact blue color to match your outfit, will this work?" Jenna dropped her hand quickly from her crotch as Dr. Truce re-entered the room. His eyebrow raised ever so subtly. Had he caught her?

"That blue looks good." Jenna responded quickly. Her cheeks burned a deep red as she realized the only blue she had on was her thong. She had forgotten that Dr. Truce could see her underwear!

Dr. Truce sat down on the roller chair with two small baggies of rubber bands. "I hope you weren't bored waiting too long." He said suggestively. Had he seen her rubbing herself? "I'm just going to move your hair over to the other side so it doesn't get in the way while I change your bands"

Dr. Truce gathered up Jenna's red hair and began to move it to the other side of the examination chair.

"What's the smell?" He asked.

"I don't smell anything," Jenna responded, confused.

Dr. Truce looked down at the handful of hair he held and noticed that it was matted and slightly damp at the end. Holding it up to his nose, he took a deep sniff and immediately recognized the smell.

"Wait a minute... does your hair smell like pussy, Jenna?" He asked accusatorially.

Jenna was caught off guard by the crudeness of the question. She had totally forgotten she had wiped up the mess between her legs with her hair earlier that morning!

Dr. Truce chastised her before she had a chance to answer. "My, my, my. I didn't realize you were into that kind of stuff, Jenna."

"Oh my god, this is so humiliating. Please, Dr. Truce, I can explain!"

"Don't be embarrassed. Embrace it! You're a kinky little girl, I get it. Remember, it's important to exude confidence even in the face of possible humiliation." Dr. Truce brought one gloved hand down to rest on Jenna's bare stomach as he talked. With the other hand, he gently opened her mouth and stuck a finger in.

"Leez dawn't 'ell my 'arents." Jenna struggled to speak as the doctor probed her tongue with his finger. This was no ordinary oral exam. Jenna could feel her crotch dampen further as Dr. Truce probed back into her mouth.

Dr. Truce's other hand slid down Jennas stomach to unbutton her shorts. He skillfully undid them with a single turn and pulled down the short zipper pressed into Jenna's outer lips. His fingers began to gently message her vulva through the blue thong. Jenna couldn't believe what was happening! Her body had been crying out for release all morning. Plus, Dr. Truce was super hot. She couldn't help but arch her back slightly, pushing her vagina towards his hand. But was she really ready to get off in such a public place? Other patients and assistants were walking past the cubicle. If even one of them happened to glance in at the chair, what would they think?

"I'll make you a deal. I'll help you start working on your self-image and confidence. In exchange, I get to help you keep exploring your kinky side. I'll also toss in all your orthodontia work for free."

Jenna's body had already made up her mind for her, though. Before she knew what she was doing, she nodded her head up and down to Dr. Truce's proposal.

"Good. Then start sucking." Dr. Truce plunged his finger deeper into Jenna's mouth, causing her to gag a little. She stifled a cough, then closed her lips tightly around the finger and sucked. Dr. Truce pulled the thong to one side exposing Jenna's sopping wet pussy to the world.

"I see I'm not going to have to do much warm-up work for you." Dr. Truce smiled before plunging his index finger deep into Jenna's hungry hole. Dr. Truce's fingers were much larger than Jenna's, and she gave a squeal when he penetrated her. It hurt a little... but it also felt amazing. This was the first time she'd had anything other than one of her own fingers inside herself. She gripped the arms of the ortho chair and tried to suck harder on the finger, as she had been instructed.

Dr. Truce swirled his finger around Jenna's sex hole, pulling her wider working up her natural lubrication. He was surprisingly adept with a finger, but Jenna realized that made sense, given his profession. He slowly worked his middle finger in next. The orthopedist worked his teen patient's mouth and pussy simultaneously. It was the most Jenna had ever taken and she felt like she was going to burst.

When Dr. Truce eventually withdrew drew his hand from her mouth, Jenna was oddly sad. The feeling of being filled up in her mouth and pussy had been surprisingly erotic. Reaching down with his now freed hand, he lifted up on her tiny yellow top and bralette, exposing her nipples to the cold office air. He bent down and sucked on one perky, pink nub. His tongue ran in circles around one, then the other. Locking his lip, he created a seal and inhaled deeply. Jenna's mind reeled with all the sensations he was creating in her. Sensing she was close, Dr. Truce rotated the fingers in her pussy once again, creating a little hook and quickly pulled down towards her feet. In the hook shape, the pads of his giant finger tips landed squarely on her G-Spot. At the same time, he reached up with his thumb to furiously flick her clit.

Jenna's mind exploded. This was the most intense orgasm she had ever experienced. Her mind went blissfully blank as she forgot about everything beyond the amazing pleasure that was going through her body. Her back arched without her control and she let out a loud moan. Her hand reflexively grabbed her free tit and squeezed hard. Her hips pushed towards the ceiling as Dr. Truce worked his fingers, extending the orgasm. When it finally dissipated, Jenna collapsed back down onto the chair in a sex haze. She didn't even notice the slurping sound as Dr. Truce removed his fingers from her ravaged pussy.

"My, that was fast. That's the tightest pussy I've felt in a while. We'll definitely need to do some work there if we're going to turn you into the confident sex-machine I know you can be. Open please." Jenna wasn't sure if it was because she was just too delirious from the world shattering orgasm, or if she was just used to following instructions from her orthodontist, but she obediently opened her mouth wide without question. Dr. Truce inserted his right hand deep into her mouth. It still stunk of her sex and was dripping in pussy juice. "Clean off my finger." He commanded. The thought of swallowing her own juices grossed Jenna out.

Nevertheless, she thought to herself that it would be impolite to disobey the doctor after the orgasm he had just given her. She went to work cleaning the sex off his fingers, trying to imitate the pornstars she had seen when they sucked dick. The taste was tangy and slightly acidic... but not necessarily a bad. It was harder than she expected, though. His fingers kept pressing on her gag reflex, and she had to fight not to just push his fingers out with her tongue. Nevertheless, she tried to keep up appearances. She closed her eyes and greedily sucked in his fingers, trying to make it look as sexy as she could.

When he was satisfied that she had thoroughly cleaned herself off his fingers, Dr. Truce removed them. "Good. Now you're ready for this." Jenna had been so busy working on his fingers that she hadn't noticed that he had pulled out his cock. It was of average size, but to Jenna it looked massive. Before she could respond, he grabbed handfuls of her bright red hair in his hands and gently but firmly guided her face over to his throbbing dick. She opened her mouth to accept his rod. His dick pushed outward on the rubber bands across her braces as he passed her teeth, expanding them to either side. The rubber bands created additional friction on his cock and he moaned slightly despite himself.

Dr. Truce used Jenna's hair like handle bars, pulling her in and out on his cock. He went slow at first, careful not to go too deep in the early stages. Jenna let him drive her like a motorcycle. She propped herself up on one arm and let the other move down to her still glistening slit. She rubbed herself as Dr. Truce increased the speed, and intensity, with which he skull fucked her. He was soon ramming deep into her throat. Her neck bulged with each thrust. Jenna had never deep throated before and she was finding it extremely uncomfortable. Her eyes began to water. Each thrust in caused her to gag, but then Dr. Truce pulled back so quickly that she barely had time to react, before he rammed right back in again. Her masturbation distracted from the pain a little, but she prayed that Dr. Truce would be finished soon. Her first orgasm had finally worn off. Now she was keenly aware of how sore her jaw was getting and the discomfort his aggressive thrusting was causing in her throat. She started to cough and wheeze around his shaft. Thick gobs of spittle squeezed out the sides of her mouth. It dribbled onto the ground next to the chair. Jenna's furious masturbation was no longer enough to distract from the discomfort of her bulging throat. She was having trouble breathing.

Just when Jenna was about to begin seriously panicking, Dr. Truce pulled out of her mouth and threw her back onto the reclined chair. He aimed his engorged member at the teen in front of him. Semen came out in thick ropes. The first Jenna her in the hair near her left temple and extended down over her eye and across her nose. The second hit her right in the mouth, decorating her pink braces with gooey white. Jenna just lay there, stunned. In the span of about fifteen minutes, she had been finger fucked by a man for the first time, given her first blow job (even though Dr. Truce did most of the work), and taken her first load in the face. She had also had the best orgasm of her life!