Jenna Improvement Program Ch. 09

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

Author's Note: Its been a little while since my last entry (Ive been getting a little self-conscious about my writing), so I've included a bit of a recap towards the beginning. This chapter has humiliation, rough sex and blowjobs, braces, feet, and just a hint of incest. If you like it and want more, you can check out the earlier chapters of Jenna's exploits (if you haven't already). As always, the story is fictional and fairly unrealistic. Hope you enjoy!

CHAPTER 9

Eighteen year old high schooler Jenna Trane could barely contain her excitement. She was about to lose her virginity. Still, she was frightened. "Please be gentle," she whispered as she lay back on the bed. "It's my first time." She wore a stunning purple ball gown, a gift from her boyfriend, Sean. Sean nuzzled her lithe neck, giving little kisses as he ran his fingers through her long, fiery red hair.

"Of course my love. I want this to be perfect for us." He whispered back. He stood and unbuckled his pants. Jenna slid her hips down to the edge of the bed, then slid down her cotton panties. They were simple, white with turquoise stripes. Sean smiled at the stark contrast between the girl's expensive, high-end gown and her schoolgirl underwear. Jenna felt his gaze and was ashamed. She should have put something sexier on. Sean positioned himself between his lover's legs. Jenna bunched the gown up at her belly and lifter he knees over her head to give him greater access. Her childish panties hung off her left ankle. Jenna reached down uncertainly and pulled her buttcheeks apart. She could feel herself moisten in anticipation of her first time.

"Like this?" She asked, seeking Sean's approval. Sean shook his head kindly.

"Relax." He said, putting her feet gently back down on the bed. "I want to see those beautiful breasts," Sean said as he rubbed the tip of his member along Jenna's waiting slit. A wispy tuft of red pubic hair acted like a beacon, directing him to his goal.

Jenna shyly reached up and pulled the thin straps of her gown off of her shoulders, revealing tiny budded breasts with unadorned pink nipples. Jenna had always been self-conscious about the size of her chest, 32 A. Even in front of Sean, her lover and closest friend, Jenna looked away, her freckled face red with embarrassment. Sean reached out and turned her chin back to meet his gaze.

"Don't. You're beautiful." He breathed. Jenna closed her eyes as Sean leaned forward to kiss her lips. The room began to spin as she felt the tip of Sean's warm shaft at her opening. It was going to perfect, just like she imagined losing her virginity would be. Nothing could ruin this moment....

Suddenly, Sean froze. The boy's face began to warp, changing into that of a much older man. Jenna recognized the face. It was her orthodontist, Dr. Truce! The doctor cackled as he reached up and gave Jenna's nipple an angry pinch.

"Ow, fuck!" Jenna jerked awake to a sharp pain in her right nipple. The teen looked around. She was naked and alone, lying on her stomach in her own bedroom. No sign of Sean. No sign of Dr. Truce. The alarm clock on her bedside table read 6:15. The skinny redhead moaned, her face collapsing into her pillow with frustration. She tried to fall back asleep, to return to the wonderful dream. Unfortunately, the combination of intense pain in her nipple and intense horniness in her nethers kept her wide awake. Reluctantly, she rolled out of bed. In doing so, she revealed the source of her pain: one of her new nipple rings was caught in the sheets. It pulled angrily at her tender bud, refusing to release her from her bed. Jenna carefully untangled herself and hopped to her feet.

Apparently, the girl's unconscious was still trying to catch up with her new reality. In her dream, Jenna had been her old self. Shy and quiet, self-conscious and totally lacking in confidence. And with unpierced nipples. But all of that had begun to change since she made a deal with Dr. Truce. Jenna's orthodontist was of the view that if you wanted to be confident, then you had to submit yourself to the utmost humiliation until you simply didn't care what other people thought of you. He promised Jenna free orthodontia, and the confidence to lose her virginity for the first time, in exchange for being her mentor as she explored her kinkier side. Dr. Truce had wasted no time putting her into extremely... compromising situations.

Jenna's eyes cast over to the pile of clothes and contraptions he'd made her wear through the mall the day before. The two scraps of white satin that Dr. Truce had called a "skirt" lay in the corner, along with a metal rod and ring that had suspend the "skirt" to hide her ass and pussy. The satin scrap that had covered her tits also sat close by, along with the chains and carabiners that had secured the tit cover to her metal collar and her fresh nipple rings. It had been surprisingly difficult to remove the carabiners from her nipples when she got undressed the night before. But once removed, Jenna had enjoyed admiring her piercings for at least 20 minutes in the mirror before bed. Perhaps that's why she had been so horny during the night. Her poor nipples had been sore from the piercing and a day of being tugged by the carabiners, but now they felt like they were on fire. She'd have to talk to Dr. Truce to see if he could do something about it.

Jenna's nipples weren't the only parts of her that were sore. Dr. Truce had attached a chain to her belly button ring that clamped on her clitoris. Jenna had endured this device as long as she could, long after she had left the mall and the watchful eyes of her orthodontist, but eventually it had become too much to bear. Now, the little arrow on her belly button piercing pointed down to a uselessly hanging clip. Jenna's clit had long since retracted back into its hood, but like her nipples, it was sore and sensitive from the previous day's stimulation.

The torture hadn't stopped at nipple rings and clit clamps. Under Dr. Truce's instruction, Jenna had attached clamps to her labia, gaping her pussy wide the whole day. Now, the clamps dangled harmlessly from the "DUMB SLUT" plug still nestled firmly in her tight butthole. Jenna had grown to like the feeling of fullness the plug provided. Besides, the label it provided seemed fitting at this point. Yesterday, Jenna had been fucked in the ass, nearly fisted her own ass, drank piss, and even had her urethra sounded while a stranger fucked her best friend on top of her. The shy virgin of her dreams was long gone. What else should she be called but Dumb Slut? But perhaps the most humiliating aspect of the previous day hadn't come from Dr. Truce. Jenna's closest friend, and recent fuck buddy, had forced her to steal a swimsuit from the Bikini Hut by smuggling it inside her ass. Jenna realized she had no idea how she was going to get the yellow microkini that Maria had stuffed inside of her out. With all of this in mind, the increasingly slutty teen had decided that she might as well leave the plug in place.

The only other thing Jenna still wore from the day before was her metal collar. Without the key, she had been unable to remove the lock that kept it in place. Eyeing it in the mirror, Jenna realized she didn't hate it. The cold metal contrasted nicely with her pale and freckled skin. It drew attention to the slender delicateness of her neck. But it was also a reminder of her pact with Dr. Truce. She was truly on the road to becoming a Dumb Slut, to be used and enjoyed whenever and wherever, by people like Maria and Dr. Truce. It was an odd thought for Jenna, but one she was becoming increasingly comfortable with. If she had learned anything the day before.... She was good at being a Dumb Slut. The orgasms (and there had been many) had been the most incredible of her life. And Maria and Dr. Truce had seemed to enjoy using her as a fuck doll. Despite all of these humiliations, Jenna still hadn't had a real cock in her pussy. That meant she was technically still a virgin. Jenna hummed as she walked to the shower, imagining all the ways her first time could be like. The teen didn't even realize that she was absentmindedly fondling herself.The pussy clamps still dangling from her ass plug tapped against her knees as she entered the bathroom.

Jenna started the water and began the process of undoing the long pigtailed braids she had been wearing since the day before. It was not an easy task. The fiery red hair had been yesterday's sex mop. It was hardened with dried semen, spit, and vaginal juice. Finally freed, the long red locks tumbled down her back. The hardened hair scratched against her bare ass. A perverse curiosity overtook the girl. Reaching back, Jenna grabbed a handful of dirty, cemented hair. What would day old sex juice taste like? After a moments hesitation, she tucked the handful of hair into her mouth and chewed on it.

"Plagh..." Jenna spit the hair back out of her mouth. It tasted disgusting. Her Dumb Slut training was coming along nicely, but it looked like she had a ways to go before she ascended to true Dirty Whore status.

Jenna stepped into the warm water. Running her fingers through her long hair, she arched her back, relishing the feeling of water dripping down her nubile body. Each drop of water's journey down her body told the story of her new sexual awakening. A single drip would first pool on the end of the collar ring that she could not take off, symbolizing her commitment to Dr. Truce. The drip then fell down onto her breast, circling round her pierced nipples and plunging down towards her belly button. The drip diverged around her belly button piercing and plunged down to her shaved teen slit where it disappeared between her legs. Jenna imagined it traveling all the way down the chains dangling from the plug in her ass. Jenna ran her fingers along her wet, nude body. She was still horny from her dream. To the young girl's surprise, she found herself wanting to be the object of pleasure for someone... anyone. Like she had been yesterday. Jenna thought about Tartan Girl and Goth Girl, the two teens that had seen her get fingered at the mall the day before. They had looked so happy, mischievously touching each other later in the food court. For all Jenna knew, it could have been their first sexual experience together. Heck, it could have been their first sexual experiences ever. Despite the embarrassment at the time, Jenna found herself proud to have played such an important role for them. If they hadn't seen a Dumb Slut get finger fucked right before their eyes, they might have never begun to explore each other's bodies.

By this point in her daydreaming, Jenna's horniness had become too much to bear. She squat down on her haunches. The pussy chains hanging from her ass plug rattled and curled up on the tub floor beneath her. The insatiable teen began to masturbate furiously. She wanted to become a sex object for the girls. She wanted to serve them, to help them further on their sexual journey. And in turn, to continue her own journey into slutdom. Jenna was shocked by the fantasies she was conjuring. She wanted the girls to tie her up with ropes and spank her. She wanted them to pull her hair and call her degrading names, like "Cunt" and "Sex Toy" and "Dirty Bitch" and to give her commands to eat out their teenage butt holes and tongue fuck their tight twats. She wanted them to stick things inside her and ravage her until she orgasmed so hard that she couldn't move. And she wanted it to ignite the same pleasure in them, to see their young faces split into pure ecstasy brought on by their mistreatment of her, their obedient sex slave. Jenna couldn't handle any more. The force of her orgasm literally knocked her off her feet. She fell backwards into the tub, laughing as the water continued to drizzle onto her face. As is often the case after an orgasm, Jenna was suddenly struck by the absurdity of her fantasies. She couldn't possibly really want any of that, could she? The teen tried to convince herself that they were just fantasies, but her behavior the previous days made her unsure. How far would she be willing to go on this adventure?

Still laying on her back Jenna's hand reached down to the chains hanging out of her ass. It was time to go fishing for the microkini. Jenna pulled up on the chain. The "DUMB SLUTt" ass plug strained at her tightened sphincter. She was surprised at the amount of force she had to use before it finally pulled out with a soft "pop." She had thought after yesterday's near-self-fisting, that her ass would be a little more pliable. After a night wearing the plug, her ass had adjusted to the plug's small stem, but was totally unprepared for the wider bulb. It looked like she was going to have to do more training if she was ever going to be able to fist herself up to her wrist like Maria wanted.

Before her asshole could close, Jenna swiftly inserted her index finger as far as she could. Biting her tongue, she wriggled the finger deeper into her rectum. The finger spun around, searching vainly for the microkini she had stuffed up there the day before. Despite her best efforts, she was unable to locate the stolen swimsuit. It looked like she'd have to get help from Dr. Truce. This would be the second time he'd pulled an article of clothing out of his teen protegé. With a sigh of resignation, Jenna removed her finger from her anal cavity and replaced it with the plug. Her hand brushed against her pubic bone as it withdrew, and she felt a small bristle. Her pubic hair was already growing back! Still laying on the floor of the tub, she reached over for her razor and shaving cream. If she was going to keep herself bare down there, it would be nice not to have to shave so regularly. Perhaps she could talk to Maria about getting something more permanent done.

After the shower orgasm, the rest of the morning was mostly uneventful. Jenna lounged around the house, watching Netflix and reading. A lazy summer morning for a highschooler with nothing to do. She had decided to retain Maria's "no underwear" policy. She wore wore a simple t-shirt and gym shorts and nothing more. It felt liberating, though she did get the sense that her father was watching her a little closer than usual. Ever since he had joined them for lunch the day before, he had been acting... strangely around her. They still weren't speaking much. But whereas before, Ronald had had trouble staying in the same room as his daughter, it now seemed like he was hovering. He waited at the table for her to finish breakfast, even though he had finished much earlier than her. After breakfast she had flopped on the couch to watch "Dance Moms." Ronald joined her shortly afterward, sitting in the armchair across from the couch. He hadn't really watched the show though, just looked at her, as if he was working up the nerve to say something. But he never did. After a short while of watching his daughter, he excused himself to the bathroom. It was only after she turned off the show that Jenna saw her own reflection in the TV screen. Her red hair was messy and kinky, pitched to one side as she lay on the couch, her head resting on her fist. One leg extended to the edge of the couch, while the other bent upright, resting her foot on her knee. To her horror, Jenna realized that lying in this position had caused the gym shorts to slide up her raised leg, providing a clear view of her vagina. She had gotten so used to the feeling of being exposed walking around the mall that she hadn't even noticed. Her father must have been staring at her pussy! Jenna was mortified.

He's probably jerking off in the bathroom right now, Jenna thought to herself. Jenna wretched at the thought and stood up. The chains attached to her butt plug dropped down, peaking out from beneath the bottoms of her gym shorts. Suddenly, Jenna was ashamed of herself. What had she been thinking, wearing an ass plug with no panties in front of her dad?! And now he was jerking off to the image of his little girl's teen slit.

Did he seen my chains? Did he read my plug? Jenna's mind was reeling. She needed to get out of the house. A quick glance at her watch revealed it was 11:00 AM. A little early for Dr. Truce's, but no matter. She just needed to get away from her perverted father. Jenna went to her room. She quickly pulled on a pair of red, low-cut Chuck Taylor's and moved to exit as quickly as possible. Her reflection in the mirror caught her eye. It was old Jenna that looked back: a shy, gangling teen with no style and no confidence. The only evidence that this was new, sexually free Jenna was the metal collar around her neck. Dr. Truce would be disappointed. Working quickly, Jenna tied her hair into a messy bun on the top of her head. She grabbed the red lipstick that she had only worn once, at her 8th grade dance, and applied it to her lips. Then she grabbed the scissors she had used to cut her shorts two days ago and roughly converted her t-shirt into a crop top. Not enough to expose under boob, but enough to expose plenty of her tight stomach and belly button piercing (with chain). Just to be sure, she rolled the top of the gym shorts down as far as she dared, then slipped the lipstick into the waist band. She might need to reapply later. This had the double effect of hiking the shorts up into her crack, providing a shapely outline to her petite butt, while also exposing more skin below her belly button. Had she not just shaved, they would have been low enough that her wispy red pubic hair would have been exposed. Now, there was nothing but inches of smooth, pale skin. Spinning around, the butt plug chains were now clearly visible brushing her inner thighs below her shorts. Jenna liked the look. As a final touch, she put on a simple silver chain ankle bracelet. The look was rushed, but effective. With greater confidence, Jenna snuck out of the house before her father had finished in the bathroom.

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"Good morning Jenna! Or should I say Dumb Slut?" Sammy greeted coyly as Jenna entered Dr. Truce's office. Jenna's face turned a sharp crimson. It sounded like Dr. Truce wasn't the only one who had enjoyed her exploits at the mall.

Sammy led Jenna to the usual chair. Like last time, Jenna couldn't help but watch the sway of the assistant's ample ass in front of her. Tartan Girl and Goth Girl had had softer, nubile features. By contrast, Sammy had a filled out woman's body. And yet, Jenna found herself thinking about Sammy treating her the exact same way she had just fantasized about Tartan Girl and Goth Girl in the shower. The thought made Jenna realize two things: 1) she was DEFINITELY into girls... all girls, and 2) she might be becoming a sex addict. There had been more orgasms than she could count in the last two days, and yet Jenna felt like she could have torn Sammy's clothes off and ravaged her right then and there. The butt plug and nipple piercings had the effect of constantly drawing her attention to her erogenous zones. It was hard to ignore the full feeling in her ass or the chains rubbing her inner thighs. With no bra, her nipples rubbed the t-shirt, providing constant stimulation. All she could think about lately was sex.

And yet she realized once again that she still hadn't actually had sex! Sure, she'd had oral and anal sex, and even been fingered by a girl. But she longed to feel an actual penis in her vagina. To lose her virginity for real. If things went as planned tonight, though, that would change. Today she was going on a first date with Sean. It was going to be her first first date. Butterflies went wild in Jenna's stomach. In her dreams, Sean was her boyfriend, but in real life, he was just the boy who barely knew her. He didn't even know her name! He only knew her as "Dumb Slut", the girl with a matching butt plug who barely covered herself in public. If Jenna couldn't convince Sean to fuck her after seeing her like that, she was in serious trouble. The date would be the perfect opportunity to finally lose her virginity.