Naughty Schoolgirl Diana Pt. 02

Story Info
Diana learns about sex toys.
4.3k words
4.5
44.4k
32

Part 2 of the 2 part series

Updated 09/24/2022
Created 10/23/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Diana had to restrain the urge to run to the principal's office after school. Principal Broadstreet had opened her eyes to the joys of sex and now she just couldn't get enough. It had been about a week since she was first called in and she had visited his office every school day after she was done with classes. It still wasn't enough. She spent all day thinking about the principal's huge cock and having it deep inside her. At least it had helped her performance at school; Principal Broadstreet had been very clear that these after school meetings could only continue if she was a good student. Lately, she had been a very good student.

Now she stood just outside his office, heart beating like a bass drum in her chest. Her panties were already soaked just thinking about today's session. At least now she knew that this was normal and that she wasn't wetting herself. Only one of the great things she had learned recently. She had just started learning about oral sex, or as the principal had called it, "sucking on his dick". He had promised to teach her about something that had her acting like a "cowgirl" this week and she had always loved Westerns. Almost trembling with excitement, she tentatively knocked on the wooden door.

"Just a minute." a deep voice called from inside.

Diana bit her lip nervously and tugged on her pleated skirt. She had just come from cheerleader practice and was still wearing her uniform. It was sleeveless, the skirt came to about mid thigh and it was in the school colors, which were white and gold. She looked around at the empty office outside his and twisted her toe into the ground.

Suddenly the door opened and she was staring right up into the principal's cold, blue eyes. He did not look happy. His tall, lanky frame loomed over her wearing a pastel blue collared shirt, black, leather belt and blue slacks. Involuntarily, she glanced down at the outline of his manhood that hinted through his pants and licked her lips in anticipation, but her attention was quickly brought back to his face by his gruff voice.

"Diana, get into my office!" He turned curtly and walked back to sit behind his desk.

Diana followed him inside quickly, worried at this new tone of voice. He hadn't been angry at her since they began their after-school meetings, and this level of angry was entirely new. She had never heard this tone before and it frightened her. She sat timidly in the hard wooden chair, hands in her lap and kicked her heels against its legs.

The principal fixed her with a hard glare and sighed. "Diana, I don't know what I'm going to do with you. This isn't just a game we're playing here; our reputations are on the line."

"What's wrong, Principal Broadstreet? What did I do?" Diana attempted to return his stare with her most innocent, puppy dog eyes.

"You fucking called me! At home!" Principal Broadstreet seethed as he almost shouted at the young girl through gritted teeth. "Look, us meeting here at school is risky enough, but at least I can justify it, but you calling me at home? That can get us both into trouble."

"I'm sorry, Principal, but, well, I just couldn't stop thinking about you. I got so horny on Saturday and, well, I just thought, if you were around, that, maybe we could... You know." Diana squeezed her legs together, getting wetter just thinking about their past few encounters. She felt near to bursting, wanting to feel him inside of her again. "Why is he angry about this?" she thought, "Its been two whole days! Why can't we just get naked?"

Dan glared at her for a second or two more before letting out another sigh and looking down at his desk, thumb and index fingers pinching the bridge of his nose, as if he felt a headache coming on. "Diana," he said, his tone now even, but one of exasperation, "these meetings we've been having, they've been great, really, and I really think they are helping you focus on school more, but not everyone would see it that way. Some would see what we are doing as wrong."

Diana looked at her hands in her lap, face reddening a bit. She knew that part of it felt wrong, but that was some of the best part, a secret with an adult that no one else would ever know about. A worry began in the pit of her stomach. "He wouldn't stop this, would he?" she thought, "He's not that angry?"

Principal Dan continued, "I think I've been too lax with you, young lady. You have to realize that, yes, what we've been doing is fun, quite enjoyable, but this is serious, as well. These are things adults do, and, now that you're 18, you need to start acting like an adult, too. If you insist on acting like a child, however, I need to discipline you like a child. Now, stand up and bend over, placing your hands on my desk. You've been here before. you know what to do."

Diana's eyes began to well up with tears and she pleaded with the principal. "But, but, no, I didn't do anything wrong. I just wanted to see you. I, I, I'm sorry. Please, I'll make it up to you. I'll do anything." Tears were flowing freely now, causing her mascara to run. She continued babbling until the principal spoke again.

"Be quiet, Diana! Stop that crying and stand up. Take your punishment and then we can move on." Dan stood up and looked down at Diana, his hands on his hips and an impatient look on his face.

Diana stood up slowly, wringing her hands and still trying to plead with him. "Please, I don't want to be spanked. It hurts. Can't I just do something to make you happy? Please. I'll do anything you say."

"If you'll do anything I say then you'll quit whining and bend over. If I don't punish you when you're bad, we'll never get anywhere with your behavior. You have to learn your lesson. That won't happen if I'm easy on you."

"I don't want to!" Diana stated, raising her voice and sounding exactly like the petulant schoolgirl she was. Looking down, she could tell by the enlarging tent in his pants that this whole scenario was turning the principal on. In her best baby doll voice, she cooed, "Let's just forget about all this spanking business and let me make you happy. I know I can make your dick happy; he's already excited to see me."

"What will make me happy, Diana," the principal said in a stony voice, "is if you'll kindly stop fucking around, assume the position and take your punishment. Either you're going to obey me and do as I say, or you're going to tell me that we're done with our little meetings and we never need to see each other again. Now what do you want?"

"Oh, no, Principal, don't end our meetings. Please, I thought you liked them, too. Please, I'll be good." Her sentence ended with a little catch in her voice, struggling to keep from crying again. She had never imagined that he was so serious as to stop their afternoon trysts. Looking at him now, she realized he was and that there was no avoiding getting her bum spanked. "O, okay. I'll be a good girl." Bending over slightly at her waist, she places her hands flat on his desk, already sniffling a bit.

Dan just looked her over for a second, still not quite believing that this delectable little cheerleader was in his office bending over his desk. He was slightly ashamed at how excited this feeling of power made him, but the throbbing in his testicles more than overcame this.

"You've only made things worse for yourself by trying to get out of your punishment. Now I want you to take your panties off and lift your skirt up. I don't want anything in the way cushioning my hand slapping your behind. You need to remember what punishment feels like. Its the only way you'll remember to obey me from now on."

Diana cast her eyes downward, as she felt her face reddening. She didn't think she had done anything wrong, but now she realized that maybe she had been a bad girl. As she slid her panties down her smooth legs and felt the tingling and heat pulse outward from her young pussy, she was certain she was a bad girl, and that maybe, just maybe, she liked that. As her panties reached the floor, Dan could see that they were already damp and the feminine scent of her excitement reached his nostrils. His erection was painfully hard as it strained against the fabric of his slacks.

Now resigned to her fate, Diana flipped up her skirt so that it rested on the small of her back, exposing her perfect ass to the principal. She placed her hands back on his desk and braced for the first slap. Dan placed one of his hands on the small of her back to brace her in position and swung back with the other hand. It came down hard across Diana's butt cheeks, causing a loud smacking sound that reverberated throughout the small office. Her taut flesh jiggled just a bit and she let out a tiny squeak of shock and pain.

Again and again, Dan's hand came down hard on her ass, turning it a deep crimson. They were slow, measured strikes, each one more stinging that the last. He counted out an even ten. He didn't want to prolong her punishment, but he wanted it to be memorable. At the end of it, her butt was bright red, but he could also see labia were swollen from arousal and shiny with her juices. He didn't think his cock had ever been so hard before and he knew he needed relief quickly.

"Don't move." he commanded, "Your punishment is done, but I want you to stay in that position."

A few tears were still running down her face, but she couldn't help but smile when she heard the familiar sound of his belt unbuckling and his pants falling to the floor. She heard the crinkle of a condom wrapper being opened and could guess down to the second the pause from him rolling it on the length of his rigid penis.

"Hold still." she heard him say, as she felt his large hands firmly grab her hips and the heat from the head of his cock as he positioned it at the entrance to her now dripping slit. He slowly worked the head in and out of her, allowing her to get used to his girth and for her juices to make his dick wet and slippery. Gradually he began working himself deeper inside of her, rotating his pelvis to stretch out the walls of her tight, teenage pussy. Finally, when the entire length of his shaft was slick, he pushed his hips forward powerfully with a grunt. She gasped as the fullness of him went deep inside her.

With Diana bent over and Dan gripping her hips, he began pumping himself in and out of her at a steady, relentless pace. Her breathing became more rapid and soft moans escaped her lips. He gradually increased his pace, their heavy breathing and the wet sounds of him slapping his pelvis against her full buttocks becoming the only sounds in the room. Unconsciously Diana moved one of her hands between her legs to her swollen clit. Suddenly, she froze as one of Dan's hands smacked her hard on the ass, both the sting and the loud crack it made shocking her into immobility.

"I didn't say to move. Put your hand back on the desk. You'll get to move when I tell you to." He held her pelvis still, with his manhood completely filling her, but his voice was as stern as ever.

Without saying a word, she obeyed and placed her hand back on the desk. After a brief pause, he resumed pumping himself in and out of her. His thrusts continued to be steady, but quicker, more rapid, until he began slamming himself into her savagely. She was nothing but a rag doll now, his powerful hands lifting her entirely off the floor, physically grinding her pelvis back to meet his cock. It was all she could do to keep her hands on his desk, but she dared not lose her grip.

She was so close to cumming, she could feel the pressure building down below, as waves of contractions began in her thighs and her pussy. From Dan's ragged breathing, she could tell he was close, as well. Then, without warning, he unleashed a guttural cry and held her hips tight up against his pelvis. The tight and tingling walls of her vagina felt the spasming of the hard cock inside her and could only imagine the flood of sperm that would have been injected deep inside her has it not been for the condom. She attempted to grind herself a bit more onto his softening erection, but he held her so tight, there was little she could do.

After a brief pause, he withdrew and she could hear him removing the used condom and pulling up his pants, leaving her teetering on the edge of frustration. Oh, how she longed to rub her little pussy and give herself at least some relief from the clenching need she felt between her legs. She dared not move, however, particularly after how stern Dan had been about her punishment. She was determined to be a good girl and obey him in whatever he said.

Soon, he was seated behind his desk and looked up at her as if he had already forgotten she was there. "Oh, go ahead and take a seat, Diana." he said, motioning to the hard, wooden chairs on the other side of his desk, "Don't bother with your panties, though. Just leave them there on the floor."

Diana sat in one of the chairs and looked back at him in a mixture of confusion and need. She was quite a sight, mascara running down her face, a thin sheen of perspiration covering her exposed skin and her heaving chest straining against her tight, cheerleader top, hard nipples clearly seen through the thin, satin fabric. Her look was one of silent desperation was she sat, hands between her legs gripping the edge of chair, alternately squeezing her legs together trying to ease some of the sexual tension she felt.

Dan looked across at her and sighed. With his elbows on the desk and his fingers tented together, he spoke, "Diana, you are a wonderful girl who is blossoming into a beautiful woman. And part of that process is this sexual desire that brought you into my office in the first place. I had meant for these afternoon visits to be an escape valve for you, so that you could have a safe, sexual outlet and concentrate more on your school work. But, after the events of this weekend, it seems that these visits might be making matters worse for you and causing you to be completely obsessed with sex."

Diana began to feel afraid. Was this a preamble to him ending their little visits? He was correct; since he had first taken her virginity, had introduced her to the wondrous joys of having a big, hard cock thrusting deep inside her, she had been able to think of little else. She hadn't known what was causing these restless, rebellious feelings and it caused her to be very disruptive in class. This disruption had caused her to be sent to the principal's office who sorted her out, first with a hard spanking, but ultimately, by fucking her senseless. Now there was little else she could think of besides his thick, veiny manhood being buried deep inside her.

"Diana!" Are you listening!"

His sharp, serious tone brought her wandering mind back into focus. "This is exactly what I'm talking about. Your libido has gotten completely out of control and its obvious that you can think of nothing but sex when you get this way. Now there's nothing wrong with this. In fact, I believe that you are a lucky, young woman to have such a healthy sex drive, but we have to teach you to control yourself."

As he spoke, he could see the look of increasing worry cloud her face and a storm front of tears on the horizon. He often had to remind himself how young and fragile she still was. "Now don't go getting yourself worked up; I'm not about to end our time together. You have to know that this has been incredibly wonderful for me, too. You are an amazing young woman and I think we still have so much we can do together, but you can't just rely on me. I'm just one guy and I think I've just found out that I can't keep up with the sexual energy of an 18 year old girl."

A wave of relief washed over Diana, softening her features. "Oh, thank goodness!", she thought; she couldn't imagine to going back to not having sex, now that it had became a regular part of her life. With that fear removed from her mind, it left room for confusion to creep in. "What was he talking about? Does he want me to have sex with someone else?"

"What I'm trying to tell you, young lady, is that I have a new lesson for you and to help you with that, I've bought you a present." Dan opened one of the drawers in his desk and took out a dildo. It was about 7 inches long, but thick and veiny, with a soft, rubbery texture and done all in electric blue. He help it up for Diana to see. "This is a dildo."

She stared at it, fascinated. She couldn't quite believe what she was seeing at first. She had just seen her first erect penis a week ago; this gorgeous representation (in her favorite color, no less! How did he know?) was a wonder to behold. She was surprised that such a thing would exist at first, but then quickly thought, "Of course this is a thing!" Tentatively, she reached out to touch it. Suddenly, she remembered her manners and looked at her principal. "May I, may I hold it?"

"Of course! I got this for you. This lesson will be how to use it." He extended his hand and placed the dildo in hers. She clutched it, marveling at the feel of it. It felt so meaty! It was rigid, but felt so, so soft on the outside. So much like the real thing it was almost frightening. Her tiny hand could barely fit around it. When Dan released his grip, she just held it for a second, hefting its weight. Holding it in both hands, she began to examine it more closely, looking at it from various angles. Finally, she looked back at him, smiled and, holding the dildo up, said, "So, how should I use this?"

A sly grin formed on Dan's lips. "I'm glad you've asked me and not chosen to start using that without the proper instruction." He stood up and moved around the desk, until he was standing beside her. He knelt down so that he was eye level with her in the chair. Taking the dildo from her, he held it up. "Since you're new to this, I think I should use this on you as your first lesson."

"Now, let's see that beautiful pussy of yours. Lean back in that chair a bit more and lift your skirt up. Ah, there it is! Just lovely." Dan's eyes were instantly drawn to her tiny, hairless mons and glistening labia.

She gushed with pride at the compliment, but was gushing down below, as well. She had been so horny and it looked like her throbbing vagina was finally going to get some attention. Him telling her what to do sent her over the edge. Her breathing quickened, her heaving chest making her stiff nipples stand out under the thin fabric of her uniform. A small whimper escaped her lips, as a fresh wave of juices flowed out of her, filling the room with the scent of her arousal.

"Spread your legs more. Wider!" She moaned as she complied with his commands. He placed one of his large hands on her pubic bone and taut stomach, firmly holding her in place, as he positioned himself between her legs. He bent his head down to run his tongue around her swollen labia, spending extra time around her stiffening clitoris, making her even wetter with a combination of of her juices and his saliva. Her hips began moving subtly as she began to find it difficult to stay still.

Then, he stopped licking, but kept his face agonizingly close to her womanhood. Softly, he blew on her soaking pussy, sending chills and a tremor through her. He was still holding the dildo in his other hand, and now he used it to gently caress the sensitive skin around her opening. This motion continued, the circular rubbing of the bulbous, blue head of the dildo around her wet slit until it was slick from her moisture. By then, Diana was writhing in her seat, thighs tensing and un-tensing while trying to stay open.

His hand pushed down more firmly on top of her pelvis to regain control of her and slowly he pushed about 2 inches inside of her. "Yessss." she hissed as a look of bliss came over her face. He established a slow, but steady rhythm, pushing the dildo in and out of her, the wide head stretching her as she accommodated its girth.

12