Claires First Time Penetration

Claire was your typical high school student. Except, she was one year older than the other students in her class after transferring schools this year. She was nineteen and managed to make a few friends and went to some of the parties now and then. She was the quiet type, but knew what she liked, enjoyed trying new things and was very open minded. She was a bit adventurous at times but far from being to the point where she made a spectacle of herself. She often thought about full blown sex and what it would be like with a guy, or girl for that matter. Not that she was a prude, far from it, she did have a boyfriend last year for a while before she left that town.

She masturbated quite frequently using her fingers, various toys and vibrators, and even the odd vegetable or object that she was able to fit inside herself. Not to mention that she has kissed girls and guys, touched some pussy and jerked off cocks, and even sucked her last boyfriend, but has never gone “all the way”. How she longed to have a nice hard stiff cock buried into her pussy one day. But it had to be the right person, the right time and place. She wanted it to be exciting and unique. She fancied some forms of porn that she saw on the internet to help her arousal during masturbation and recently became aware of domination and submission. Some people have extreme fetishes and really get into the whole dom/sub life style, she thought. She was very curious how far her limits may take her one day.

Claire was a real beauty, a swim suit model type and extremely sexy, shoulder length brunette with short bangs, perfect sweet innocent looking face, blue eyes, perfect white teeth, nice full lips, stylish dark rimmed glasses, very strong fit legs and butt, and nice firm smaller 32b breasts. She enjoyed working out and keeping in shape. She was relatively short, 5′ 2″ and 110 lbs. With her being so tiny, she had a very tight and nicely trimmed pussy. She could barely fit three of her fingers into herself, and the largest dildo width that she could accommodate was 2 inches.

It was autumn and a nice warm day. Claire thought it would be fun to wear a shorter skirt, down to mid high, and maybe go to school with no panties. With short socks, sneekers, and a nice tight fitting white top, it would look lovely she thought. She let her hair down today. On her way to school, she noticed three boys from her class behind her. She didn’t really pay much attention to them.

As the boys got closer, one of them yelled to her, “Hey Claire, aren’t we pretty today.” Claire turned around, just smiled and kept walking. One of the other boys said, “More like she is slutty today.” as they all laughed. Claire didn’t bother turning around and kept walking as the boys crossed the street and walked down a different path to school.

No one has every said those things to me she said to herself. Although she was a bit frightened by the second boy’s words, she was also slightly turned on and felt her juices begin to flow at the thought that some guys figured she was pretty and sexy, even slutyy! In fact, as she walked further and kept thinking about it, she felt the skin between her upper inner thighs begin to rub together more than usual, due to the moistness from her pussy dripping down slightly. She was now fully aware of her sexual being for the day, and daydreamed through some of her morning classes.

Lunch hour rolled around and she decided to stay at school, maybe sit outside and enjoy the warm sunny day. It was now getting a bit windy outside and her dress was flapping around slightly, so she would have to tame it once and a while during her walk to the picnic table. She saw some teachers and students nearby who were out for lunch also enjoying the day.

To her shock, a gust of wind came upon her and blew her dress a bit above her waist, then she urgently grabbed it and pulled it down quickly. She looked around in a haste to see if anyone was watching. It was not obvious anyone was looking. A soothing relief went through her. My God, she thought to herself, what if someone would have seen me, my dress blown up, no panties, a full view of my ass and maybe even my pussy! What would the teachers think? What would they have done?

As she sat down and ate her lunch she slowly glanced around again to see if anyone was looking at her. Maybe she could tell this time if they saw anything. I guess not, she concluded to herself. The thought of someone seeing her got her excited, the second time she felt this way today. She never felt this way before. Was she a closet exhibitionist? Would she really enjoy people seeing her naked body? Maybe someone did see me. Maybe a teacher? Maybe a student? The thought sent shivers down her spine. Her pussy began to moisten under her as she unconsciously slipped her right hand between her legs and pressed her wrist slightly into herself.

She began to daydream that a teacher saw her and walked over to her while everyone else went back into the school. He would approach her from behind, put his foot on the seat of the picnic table saying, “I saw that you know.”

She would turn to him, look him in the eyes but say nothing, and just bite her bottom lip. Then swing one leg over the seat of the table, ever so slowly spread her legs for him and lean back slightly. Her dress would part, exposing her young pussy to him, glistening with her juices, and a moist patch under her on the wood seat below and very noticeable.

The teacher would say nothing, just grab her by the arm, pull her up, spin her to face away from him and push her against the picnic table, pinning her against it with the weight of his body. His body next to hers from behind, she could feel the large bulge in his pants pressing against her ass, getting harder and harder very quickly. He would grab her head, twist it to the side and kiss her deeply, probing his tongue into her young mouth. Then suddenly take his hand and place it between her shoulder blades and push forward, making her bend over. He would push her down fully with both hands onto the picnic table, the bottom of her skirt now lifted up to her waist, exposing her ass and pussy to him. He forcibly inserts one, then two fingers into her dripping hole, then begins to wiggle them around inside slowly, pressing on her g-spot with each rotation, making her squirm and cum almost immediately. He quickly removes his fingers, unzips his pants and forces his large hard cock into her in one full motion, filling her tight young pussy to her cervix. She arches her back and would instantly cum on his cock, feeling its hardness and length pushing deep into her.

She immediately sprung from her daydream as a bird startled her thoughts. Wow, she thought. That WOULD have been exciting. Maybe not unique, but exciting nonetheless, at least to her. Would she have the courage to do such a thing in real life? Would the teacher have played along and taken me on this table or taken me somewhere else? Maybe he would have told me to cover up and have me expelled! She gathered her things and walked back to class, all the while, with her upper inner thighs rubbing together as they did on the way to school.

Once her first afternoon class was done, she thought she heard her name on the P.A. system. Could it be? I have never heard my name called before, she thought. Maybe my mother was trying to get in touch with me, she thought. Maybe something bad has happened.

Then again, the voice on the P.A. system said, “Claire Darling, please come to the principals office.”

Yup, it was her alright. A wave of panic went through her. What was this all about, she thought. She quickly made her way into the office and went to the administrators desk.

“Hi, I’m Claire Darling, the office called me on the P.A. system.” she said.

“Oh yes, please have a seat, the principal would like to see you.” the lady at the desk said. Her name plate had Mrs. Sterling on it.

Principal, she thought to herself. Why would the principal want to see me? she thought.

The principal suddenly appeared from around the corner, not giving Claire any time to think.

“Miss Darling!?” he asked, while looking at Claire.

“Yes Mr. Strong, I’m Claire.” she said back to him.

“Come with me.” he said.

“Mrs. Sterling, please ensure no one interrupts us and no phone calls while I am busy here, ok?” he said to her.

Mrs. Sterling politely said, “Ok sir, no problem.”

Shaking with fear, Claire got up, grabbed her bag and followed him down a short hallway to his office.

He stepped aside to let Claire by him. “Have a seat young lady, we need to chat.” he said. The tone in his voice was fairly stern, making Claire a tiny bit frightened. What did she do to get here she thought.

Claire sat down in a wooden chair with no arms. It was an old style chair, well built and sturdy. Mr. Strong was a bigger man, about 6′ 2″, 200 lbs, well built and not overweight at all. He was somewhat attractive for a 45 year old man with shorter dark hair and was wearing a suit. He sat down across from Claire on the other side of his desk, leaned over, and crossed his fingers together, while looking at her.

“I have been informed about something that troubles me, Claire.” he said.

Claire looked at him extremely distraught. “W-What do you mean sir?” she barely voiced back.

“Well, I was told that you were flashing yourself during the lunch break outside on school property.” he said in a stern voice.

“NO!” said Claire, with a louder confident tone. “The wind blew my skirt up and I quickly pushed it down as fast as I could Sir!”

“Well that may be the case, but we need to check something else.” he said. He stood up from his chair. “Please stand for me and show me what you’re wearing under that skirt young lady!”

Claire was shocked at his words. Fear overcame her whole body as she looked down at the floor. Who could have seen her at lunch time she thought to herself? Who would have finked on her? For a brief moment, oddly enough, the whole scenario of the principal wanting to see under her skirt turned Claire on, but then the fear seemed to dominate once again.

“WELL!?” Mr. Strong yelled.

“Oh Sir, I’m terribly sorry, I will never do it again, I promise!” barked Claire.

“I didn’t ask for an apology my dear, I asked you to show me what’s under that dress.” he said, in a soft but stern tone.

“But, but … I can’t do that Sir.” said Claire, in a very quiet voice while looking at him with a bit of a frown.

“Why not?” Mr Strong said. “You CAN’T or you WON’T!?” he barked back at her.

Claire could not think clearly. Surely in the right frame of mind she would say to him that he could be in a lot of trouble for asking her to do this. Or she could scream so someone could hear her. She did not think of any of this, just that she was in a lot of trouble and in huge predicament.

All she could muster was, “I can’t … I won’t … I’m … I’m … not wearing anything … there … I said it … now please leave me alone!”

A strange wave of relief went through her after telling him she had no panties on. That turned on feeling quickly returned to her once again knowing that he now knew the truth. To her surprise, she felt her pussy begin to respond, it was getting wetter the more she thought about it.

“I’m afraid I can’t do that Claire” said Mr. Strong. “You have been a VERY naughty girl, and you deserve to be punished for what you’ve done.”

“What do you mean, punished!?” said Claire. She had no idea what he had in mind. Does he mean telling her parents and being expelled? Her parents would be mortified as they are very conservative and church goers. But then, suddenly, she thought, maybe he plans to have his way with me. He did say he wanted to look under my dress. When under such pressure, it was hard for Claire to think straight. It would have been obvious to anyone that Mr. Strong knew exactly what he wanted for punishment.

Mr. Strong raised his voice, “I’m the one asking questions around here, not YOU! You still have not shown me what’s under that dress young lady!”

“But, I already told you, I have nothing on Mr. Strong” Claire said softly.

“Are you getting cheeky with me!?” he groaned. “You had better fix that tongue my dear, or else!”. “Now pull up that dress and show me what you have under there, NOW!!” he yelled.

Not knowing what else to do, Claire reached under the bottom brim of her skirt with both hands. She could not believe what she was about to do. She was feeling extremely afraid but was also feeling equally excited. Her pussy was wet. Time was running very slowly, everything seemed to happen in slow motion.

She slowly pulled up her dress as she looked down, with the upper thighs exposed. Mr. Strong was now visibly excited and just stared as he watched this beautiful creature pulling up her dress in front of him. His cock was bulging from his pants.

Further up it went, now exposing the top of her pussy and nicely trimmed bush above her pussy lips. The skirt was now around her waist as she held it there and he could see her very firm muscular legs and sexy hourglass hips.

Claire slowly looked up at him, unknowingly bit her bottom lip and stared into his eyes. Her heart was pounding so hard, she could have sworn it was going to pop right out of her from the shear fear and excitement all at the same time.

Mr. Strong’s cock was so hard, it was making a huge bulge in the front of his pants as he stood there with his arms crossed in front of him. Claire noticed and stared down at his large bulge. She now knew exactly the kind of punishment the principal meant, and her pussy began to respond with pure excitement.

The fear quickly left her body and now the exhilaration of what was to come overwhelmed her so much that she almost came without even being touched. The principal was peering down at her young pussy and licked his lips as he stared at her bare sex.

The principal looked at Claire in the eyes, “You are a VERY naughty girl Claire. We can not have students flashing themselves on school grounds. You are to NEVER do that again, understand? The ONLY time I want to see your bare ass on school grounds is when you are in THIS office or WHEN I ask it to be so! GOT THAT!?” blurted Mr. Strong.

Claire could not believe her ears, but his words sent shivers through her entire body, she was so sexually aroused. This was the kind of exciting, naughty, sexual encounter she desired for her first real cock experience. She needed so badly to have this man’s cock inside of her. She always wanted her first fucking to be with an older gentleman, and the fact that it may be with her principal blew her mind and made her wet beyond her imagination.

“Yes Sir, Mr. Strong, I understand. I understand completely” Claire softly muttered.

“WHAT was that Claire? I didn’t hear you. Please speak up …. you little cock tease” the principal exclaimed.

Claire spoke out loudly, “Yes Sir Mr. Strong, I understand. Please don’t punish me, I will do as you say, Sir”

“You think you’re going to walk out of here without being punished, DO YOU!?” he smirked. “You have another thing coming my dear. After your cheekiness and naughty behavior? You knew exactly what you were doing when you left home this morning without panties under that skirt … and you think you deserve to walk away unpunished? I have other plans for you my dear.”

Claire’s excitement and not knowing what he had planned for her was making her crazy with lust as the blood rushed to her pussy, swelling it to levels she has never experienced. She was weak in the knees. This tall, dark, handsome, well built man is probably going to take my cherry and I’m not sure what will happen as soon as he touches me she thought to herself.

With Claire still standing in front of him and her skirt pulled above her waist, the principal moved toward her slowly staring at her. He walked around behind her and stood there, staring down at her perfect young ass and legs. Her ass was pure heaven. There was nothing more erotic. It looked so soft and perfect, he could barely stop himself from reaching out and grabbing it. Licking it.

“Claire, please approach the desk in front of you, and place both hands on it.” he said, as he sat in her chair behind her.

Claire did as she was told and was going insane with the thought of what he was going to make her do.

“Now, pull that skirt up to your waist again.” he said in a soft voice. “You’re getting more obedient. So far so good Claire.”

Claire hiked up her skirt slowly, inch by inch. As she did so, the tops of her thighs grew more exposed. As the skirt slid higher, her round, perfect firm ass appeared in front of him. He could also see a tiny bit of her pussy lips as she had her legs fairly close together.

“Oh no” said the principal. “Not anymore. You’re not going to be a pussy tease with me any longer my dear. Spread those feet apart for me baby, and do it slowly.” as he grabbed his rock hard cock after it sprung out of his unzipped pants.

Claire was now in absolute bliss with sexual tension. Her pussy was swollen and dripping. He would surely notice once her legs parted. She slowly moved her feet apart as her sneakers slid easily along the floor. One foot, two feet, her feet separated. The principal could now see more of that young glorious pussy being exposed to him. She was completely bare except for the neatly trimmed dark bush above it. Her asshole looked so wonderful, like it had never been penetrated. His cock was so hard, it stood straight up in the air as he leaned back in the chair. He thought he would cum right then and there.

Claire began to peer behind her to look at the principal, to see what he was doing. She only caught a quick glimpse of his body sitting in the chair before he shouted to her, “Ah ah ah. Turn around Claire, or there will be trouble” he said in a stern voice.

She quickly turned forward again. Damn it, she thought to herself. I thought I saw him rubbing his cock but I couldn’t quite tell. I couldn’t see how big it was. This excited Claire even more. Her principal sitting behind her, jerking off his cock while he was looking at her, with a hiked up skirt, bare ass and glistening wet swollen pussy. The tension in her mound and body was building further, making her very weak in the legs and on the verge of an explosive orgasm. She needed his cock in her, now, but she was reluctant to say anything. She just began to spread her feet apart further, very slowly as he asked.

Further and further apart her legs spread, exposing her pussy to him more and more with her swollen pussy lips now slightly open. The shape of her ass getting more and more erotic as her muscles tightened. Her tight asshole now fully in view above that young sweet pussy.

Claire heard the principal get out of his chair and felt him moving closer to her. “Do not turn around Claire.” he said. She was in sheer agony waiting for his next move. Will he touch me?

He bent over behind her to inspect her ass and pussy up close, but did not touch her. The principal’s eyes widened and a smirky grin came upon his face.

“My my, isn’t the naughty cock tease wet … and very swollen.” he said to Claire. “Your pussy looks like it’s enjoying this very much Claire. It’s extremely wet and swollen. I guess you’re enjoying what the principal is doing to you so far Claire.”

He crouched down and moved his face extremely close to her sex, almost touching his nose to her. Claire suddenly felt the warmth of his breath on her pussy. It was fairly rapid and she could feel each exhale blow over her dripping wet hole. After the fifth exhale, to her surprise, her body suddenly reacted. A wave of pleasure ripped through her legs and hips and down her spine as she felt them quiver. Her swollen gaping wet pussy went into rapid quick spasms. This happened again and again randomly as he continued to breath on her. Claire’s eyes closed tight and she clenched her fists together with each orgasm. Claire was shocked at her reaction to his breath but she loved this new feeling she was having. None of her orgasms have ever been like that. Never so lustful, so erotic, so pleasing. She was finding it difficult to stand and was leaning more on her arms, adjusting her weight.