Claire's First Time Penetration free porn video

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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 u*********sly 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.
The principal noticed the quick spasms as her pussy lips opened and closed with each one. Small amounts of her fluids squeezing out her with each spasm as single drops fell onto the floor of his office. The sight was unbearable to Mr. Strong, knowing that this pretty young thing was reacting to him this way. His cock was extremely hard and he needed to push it deep into her. But he wanted more fun with her first.

He slid his shoe under her dripping pussy to allow her juices to gather onto his shoe.

"Claire ... " said the principal. "You're cumming all over my clean shoe. Now bend down and lick it for me. Lick your cum off my shoe, you pretty little slut." he said. "You're just lucky I'm in a good mood, I did not say you were allowed to cum Claire. The next time you cum, you will need to ask my permission Claire, or else!"

Claire did what was asked of her. Maybe this was her chance to see his cock. She began to turn around and suddenly, he shouted, "DO NOT TURN AROUND CLAIRE ... I thought I made that perfectly clear! Keep bending over the way you are and slide backward toward me. That's it, keep going. Ok, now stop. Crouch down and lick it Claire, lick your cum for me."

Claire crouched down as he lifted his leg to meet her. "Grab my leg Claire and lick your pussy juice from my shoe." he said. Claire grabbed his leg and pulled it up so she could get his shoe toe close to her mouth. As she was about to stick her tongue out to meet her own juices, she felt his leg brush against her clit. This made her squirm and move her hips around on his leg, almost making her cum again.

"Claire! You had better not cum on my leg my dear." he voiced in a rigged stern voice. "Now let me see you lick your cum off my shoe."

As she pulled his leg up, she began to lick her juices with the tip of her tongue so as to not hump his leg, rolling it around and pulling it into her mouth every so often. She's always loved the way she tasted. She still felt his leg brushing her clit as she licked at his shoe, making her pussy quiver over and over, on the verge of a much more intense orgasm.

"You HAVE become my slut haven't you Claire? You like this treatment don't you? Your pussy is aching for a hard cock isn't it Claire? ISN'T IT? ANSWER me, you little SLUT." he barked at her.

Claire stopped licking her juices from his toe and whimpered to him, "Oh, Mr. Strong ... Sir ... I'm so fucking horny, your breath made my pussy cum like it has never cum before ... I wanna feel it again ... I need to cum harder so badly ... Please put your cock into me Sir ... This slut needs your cock inside her so badly ... My young pussy is sopping wet for you ... My legs are weak and shaking ... I need your cock ... PLEASE!!!!"

"Oh Claire, I like the obedience I am hearing, you're becoming a very capable slut for the principal" he said, in a well natured tone. "You do need some cock, you fucking teasing slut, and you'll get it ... when I say so." he exclaimed.

Claire needed his cock so badly, the anticipation was excruciating and she was disappointed that she had to wait longer.

Her ass was pure heaven, legs well apart. "Stay right there Claire, don't move, and do not turn around." he said, as he bent over again to look at her sopping wet swollen pussy. He just had to touch this beautiful young goddess's sex. He reached between her legs and very lightly put two fingers on her that straddled her pussy, one on each of the lips. He then began to pull his hand back, all the while brushing the outside of her pussy lips until he reached her ass.

As soon as Claire felt his fingers placed on her, she shook and shivered noticeably. "Mmmmmmm" Claire moaned sharply. As he brushed over the entire length of her pussy, she lost control of her body and was shivering and moaning the entire time, "Uhhhhhhhhhhhh ... ahhhhhhhhhh ... oooooooooo ... GOD ... GOD ... FUCK ... OHHH MYYYYY GOOOOOOD!!". Her head was cocking back and forth with each powerful orgasm.

"CLAIRE!!! I thought I told you NOT TO CUM!!" the principal shouted. "You're being VERY bad again Claire" he harped. "I think you need a spanking my dear, then maybe you'll learn not to do that again."

Before Claire could say or do anything, he got up, raised his hand, and slapped her ass so hard that it became beat red with his hand print clearly noticeable.

Claire's body jerked forward as his hand met her ass sharply. She let out a loud yelp, "aaaaaaahhhhhhhoooooowwww" as tears began to run down her cheeks from the shock and sharp pain.

"Do you need another one Claire?" he asked her.

"NNNNNNOOOOO!!" Claire yelled back. "No more ... PLEASE .. no more!" with her eyes shut tight.

"Keep those eyes shut Claire. Are they closed?" he asked her.

"Yes, Mr. Strong, they're closed" she whimpered, still reeling from the pain on her ass.

"Good. Now turn around. That's it, turn around, and sit on the desk." he said.

Claire slowly spun around with the pain in her ass now subsiding. She sat on the edge of the desk waiting for her next instruction. She had never been slapped on the ass so hard. The initial pain was rough but she was now getting a strange feeling within her that she never felt before. With her sexual desires so distinct and electrifying, the spanking was making her submissive behavior even more exhilarating and exciting. Her pussy was still extremely swollen and wet beyond what she has ever experienced before. The spanking seemed to excite her senses after the initial pain was slipping away.

Keep those eyes closed Claire. Good. Now, spread those legs for me baby, slowly." he instructed. "I want to see that young bare swollen pussy again."

She slowly opened her legs, pulling her knees apart as her feet were dangling on the edge of the desk. The sexual excitement was beginning to build in her once again, her eyes closed and not knowing what he was going to do.

The principal crouched down again. He had to taste this sweet young pussy. It was driving him mad ever since he laid eyes on her. With this beautiful young sexual creature, legs fully spread, her gaping, swollen and dripping wet pussy was something to be marveled. Relished. Cherished. He was in pure heaven.

Her outer pussy lips were so swollen and pink, they spread apart from each side, exposing her soft smaller inner lips that were also visibly swollen. Her clit was extremely sensitive, poking out of its hood and very hard with cunt juices everywhere, making her glisten like gold. A small stream of her fluid was slowly dripping down between her outer and inner lips, reaching the crack of her ass on the desk, where a small puddle appeared.

The principal grabbed her top at its base then flung it over her head in one full motion, exposing her young small breasts. Her small nipples were already hard from her sexual excitement but became more so with the cool room. She was now topless, perfect teen nipples erect, her skirt pulled up around her waist, legs spread open wide, and her feet dangling off the desk with her short socks and sneekers on.

The principal moved in toward her breast and licked it ever so lightly with the tip of his tongue. He circled it around and around then sucking her nipple into his mouth. Claire grabbed the back of his head and pulled him into her, moaning with his technique. Her nipples were very sensitive and she could feel the effect it was having on her pussy, tingling with each lick around her budding nipple, having mini orgasms as he continued on each of her nipples, one after the other. He stopped what he was doing then stood there.

"Now Claire, listen to me. Keep those cock tease eyes SHUT. Do not move. Do not speak. Do not moan. Do not make any sound at all. Do you understand?" he said, in a very strict tone.

"Y-Yes Mr. Strong, I ... I understand." Claire said, in a soft voice as she unknowingly bit her bottom lip in anticipation.

He positioned himself between her legs, then puckered his lips and blew a long thin stream of air over her clit softly, changing the angle of the air stream once and a while making it pulse over her clit. Claire's body suddenly became rigid as she stiffened up and sat upright, gripping the edge of the desk under her palms. Her eyes completely shut tight as she clenched her teeth together with her lips now tucked between them. She did not dare to make a move or sound. It was sheer agony not to as she felt the air stream tickle her clit over and over again, like he was licking her. Wave after wave of pleasure went through her body with each pulse of air riding over her clit. Her body stiffening with each pulse and her breathing became more erratic.

He placed his tongue at the bottom of her pussy and lightly licked it moving upward toward her clit, grabbing her juices along the way. How her sweet nectar tasted in his mouth. He could eat this young pussy for ever, swallowing her up. He rolled his tongue over her clit then back down to the bottom of her pussy, slipping his tongue deep inside of her.

Claire was going crazy not being able to move or say anything. She pushed her feet forcibly with all her strength into the desk making them wedged between the desk wall and table top to stop herself from moving. Her arms were rigid as she gripped the desk and clenched her teeth. Her breathing was extremely erratic and very audible with each inhale and exhale from her nose.

He took his finger and inserted it into her tight cunt, pushing it all the way up into her g-spot then moving it in and out of her slowly as he sucked on her clit. Her pussy was very tight around his finger as he fucked her with it. He could feel her pussy tighten around his finger as it probed deep into her, with each powerful orgasm emanating through her body. Her juices spilled onto his hand and her body would twitch and shake uncontrollably with each thrust upward.

Claire was screaming in pleasure with her mouth closed, eyes shut, the look of pain on her face and grasping the desk top as hard as she could, not to move. The sight of this young girl's pussy cumming all over his hand and her body reacting the way it did was too much for the principal. He had to take her with his cock. He had to feel this wonderful pussy wrapped around his rock hard cock.

Claire managed to keep it together during the incredible ordeal as much as she could. It seemed like an eternity. She finally relaxed her back and shoulders after he slid his finger out of her.

"Claire, I'm impressed. You managed to sit through that extremely well." said the principal. Claire could say nothing as she was still coming down from her series of orgasms. He stood before her now only a few feet away and said, "Claire, you can open your eyes now." he said.

Finally, she thought to herself, and didn't hesitate. She wanted to see his cock. She slowly opened her eyes with him standing in front of her totally naked. His strong arms and chest were what she was dreaming about, fairly muscular and well toned. She moved her eyes to his cock. Her mouth opened as she stared at his wonderful member. It must have been 8 inches and fairly thick, thicker than any dildo she has ever used and much bigger than any guy she has been with. It was extremely hard and standing straight out toward her. She could not wait to take that wonderful cock into her swollen pussy. She could only imagine what it would feel like inside of her and what effect it would have on her in this state of constant arousal.

"Oh Mr. Strong. I need your cock inside me. Please give it to me. Please fuck my young slut pussy with that cock. Give it to me. Take me. Take my body. Fuck me everywhere with that huge cock." she blurted.

She could not believe what came out of her mouth, she lost control and all she wanted was his cock deep inside of her, pounding her with it, making her cum like she has never cum before.

The principal moved quickly toward her as she sat on the desk leaning on her hands behind her. He grabbed her knees and poised his cock at the entrance of her tight young pussy, then pushed the head against her pussy lips. He grabbed her head with his hands on either side, leaned into her and put his lips on hers, kissing her deeply. She wrapped her arms around his neck and put her tongue deep inside his mouth, probing to meet his tongue.

He pushed his hips forward quickly causing the head of his cock to enter her dripping wet hole. Claire's head suddenly cocked backwards with her mouth wide open and eyes tightly shut, her face cringing with pure lust, and the sound of air escaping from her lungs as he pushed into her. The principal had a look of pain on his face, as he tightly held her close to him. The feeling of the young girl's sopping wet tight pussy around his cock almost sent him over the edge. The feeling was like nothing he had ever felt. They both sat there still, breathing heavily, their heads on each others shoulders, and ears locked together with his cock head buried inside her.

He pulled her tighter to his body and thrust into her again, sending it deeper into her cunt. It was still not completely in. Claire's body quivered and shook uncontrollably as he held her in his arms. She was having another intense orgasm as they both paused again, with his cock buried more deeply inside of her. She was totally out of control of her bodily reactions. She moaned and groaned with her face tightly pushed into his shoulder as each wave of orgasm went through her body, from her pelvis to her spine, tingling all over.

The principal felt her pussy tighten and release around his cock with each spasm of her orgasm. Her pussy muscles grasping at his big cock, trying to suck him in deeper. The feeling around his cock was incredible. This beautiful young girl's swollen tight sopping wet pussy wrapped around his huge cock. As she was cumming, he felt the warmth of her juices squirt all over his cock with each pulse of her orgasm. Squirt after squirt, running over his cock and dripping down his legs. This was too much. He had to cum inside her cunt.

He unleashed his grasp of her and pushed her torso down on the desk. He grabbed her knees and pulled them up to him so he could grab her ankles. With his hands on her ankles, he spread her legs wide apart, exposing her dripping hole with his half buried cock still inside of her.

He looked at her with a look of pure lust. Claire's head was tipped to the side, eyes shut and arms limp at her sides. She was lost in her state of constant orgasms with his cock inside of her, some more intense than others.

He was going to get his entire cock into her and would pound her cunt over and over until he came inside of her. He pulled his cock back slightly, with the head still inside, then pushed forward slowly so as to not hurt her. He kept pushing forward until she said something.

Four inches, five inches, then, "ahhhhhhhhhhhhhh' Claire groaned with a sigh. His cock was so thick it stretched her young pussy to the limits.

"Oh my God" Claire said. "Oh ... fuck ... that feels soooo fucking good. Don't stop, keep pushing" she said, as her head tipped back arching her back.

The principal pushed forward, sending his cock another inch into her sweet tight young pussy.

"OOHHHHHHHHHHH!!!" cried Claire. "Fuck .... Fuck ... Oh my God ... hold it there ... hold it there ... I wanna feel it inside" she groaned, as she felt another orgasm rip through her and on the verge of another one, but much more intense.

He held his cock there for a few seconds then pushed deeper into her, slowly, all the way to his balls. His cock was totally buried inside of her and felt like a tight hose around it, squeezing it. He pushed his groin into her and held her tight, not moving. The feeling of her pussy around his cock blew his mind with lust.

"OOOOOOOOOHHHHHHHHHHH ... FFFFFUUCK" Claire yelled. Then she groaned in a deep soft tone, "OH ... MY ... GOD." and suddenly screamed into the room, "it feels SOOOOOO HUGE!!!!" with her head totally tipped backward away from him. Her hips pushing into his groin taking his entire cock to her cervix.

They both felt her body beginning to react violently, her pussy muscles beginning to contract around his cock again with short small pulses. Claire began to moan the most erotic sounds he has ever heard come from a woman as she was coming constantly on his cock.

He wanted to fuck her. He needed to fuck this young pussy, good, hard and fast, like it should be fucked.

He pulled his cock back slowly until it reached the head, all the while Claire's body was jerking and quivering with the feeling of his huge cock pulling out of her. Then he began his assault on her pussy.

He pushed into her all the way to his balls, then pulled back, and repeated this for several minutes but not yet pounding into her. With each thrust forward, Claire's head would tip back and she would arch her back to meet his thrust, moaning and groaning and not saying anything that could be understood. He could feel hitting her cervix with each full thrust into her.

He suddenly picked up his pace and thrust into her faster and harder, increasing until he was pounding her young pussy veraciously. He could not believe how tight and how sopping wet her teen pussy was, his cock sliding in and out of her hole with such ease. His cock began to swell, on the verge of a massive orgasm.

Claire completely lost it while he pounded away at her young pussy. Her head was violently shifting from side to side with his assault on her, eyes closed and mouth open, screaming, "OH FUCK ... OH FUCK ... GOD ... YESSSS .. FUCK ME ... FUCK ME ... AHHHHHHHHH ... OOOWWWWAHH ... RIGHT THERE, THAT'S IT ... THAT'S THE SPOT ... POUND MY PUSSY ... MMMMMMMMM ... OOOWWWAHH ... AHHHHHHHHH ... I'M CUMMING ... I'M CUMMING ... AHHHHHH .. ALL-OVER-YOUR-FUCKING-COCK ... OH-MY-GOD ... FUCK ... FUCK ... AHHHHHHHHHHH".

Her young body was reacting uncontrollably to his cock as he fucked her like a wild a****l, violently convulsing, shaking and shivering while she came all over his cock the entire time he was fucking her. Wave after powerful wave went through her body as his cock hit the back of her cunt with each thrust. Her pussy muscles contracting and releasing, with very strong spasms causing her fluids to squirt out like a constricted hose as he pushed forward making a, "sssppsssssssss, sssppsssssssss" sound as it squirted out of her all over his chest and legs.

With each spasm and squirt, Claire muttered, "AHHHH, AHHHH" as she raised her head up and push her hips forward and upward to intensify the orgasm.

She could not believe what her body was doing, it felt so fucking amazing. Never had she cum this violently before. She loved being a submissive slut and wanted nothing more than to fuck like this for the rest of her life she thought to herself.

With Claire's body reacting the way it was, the principal's cock was swelling beyond belief and getting ready for the most powerful orgasm he has ever had. He kept bucking into her, pounding her, grabbing her thighs and pulling her into his huge cock. Her tight young pussy wrapped around his cock, sucking it in, wanting his cum inside, never feeling such a tight young pussy.

"Oh Fuck .... Oh Fuck ... Claire ... I'm gonna cum ... I'm gonna cum baby" he said, in a hasty voice between his heavy breaths. "I'm gonna cum inside you baby. I'm gonna give you my cum ... All inside that tight young cock tease pussy ... Do you want it baby? ... Do you want it? ... Tell me baby."

Claire managed to yelp out a few words while caught up in her own continual onslaught of powerful orgasms. Her young cunt spasms were much closer together, making her voice very broken, only able to speak between each brief strong wave that made her head go back, body convulse, clench her teeth, and between each deep breath, "OH ... YEAH ... CUM ... INSIDE-ME ... FUCK ... YEAH ... I-NEED ... YOUR ... CUM ... INSIDE ... ME".

He kept pounding into her as her pussy kept cumming and still squirting on him with each thrust forward. Then suddenly, he felt his cock go into huge spasms, shooting his cum deep into her young squirting cunt. He gripped her thighs and pulled her body into his crotch, holding his cock deep inside of her, not fucking her any longer.

He wanted to feel his cum shoot deep inside this young sweet innocent girl beneath him as she lay on his desk. His head tipping all the way back as he held her into him, shooting stream after stream into her hole.

They could both feel the warmth of his cum, pooling inside her pussy. Claire had one final huge orgasm feeling his cum deep inside of her with her head back and spine fully arched, "OOOHHHHHHHHHHHH ... GOD" she moaned in a deep low voice.

The principal collapsed on top of her, both of them breathing heavily after the most incredible sex they have ever had, with his cock loosing its erection and still inside of her. It finally slipped out of her pussy with one sloppy pop after her pussy spasmed one final time. A large blob of cum popped out of her as his cock was sprung out, with more cum oozing out of her sopping pussy for the next few minutes.

Claire reached down and dipped her finger into herself slowly. "Oh my God" she said, still breathing heavily. "It's so fucking wet". She pulled her fingers to her mouth and licked them clean, each individual finger at a time, then swallowed it all.

This would not be the last time for the principal and his new submissive cock tease slut. He was already thinking of the next time.

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Master of All Timelines

Your name is Edward Richardson. You're 20 and you've been fascinated by history ever since you're 11. You're also good at making inventions as well. As you're growing up, you usually found that at various points in history of each country, things always turned ugly at many points. And you wanted to change that. You decided to use your intelligence you create the device called the T.O.S, abbreviated for Timeline Opener and Stopper, that can make you travel back in time and alter the histories...

Mind Control
3 years ago
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First Time Sex With My Longtime Bestie

Hi everyone Akshay here, age 23 from Chennai. I’m a reader of ISS for the past 5 years, and it’s high time I shared my experience. This happened a couple of months back. It was with my longtime bestie. Her name is Vaishali. We know each other for around 6 years, starting from our college days. She lives half an hour away from my place. I’m pretty familiar with her parents. We got to know each other from our college days as we were from the same department. She had a sexy shape, which gave me a...

3 years ago
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My First Double Penetration

With a whole lot of help from MisterDp! Thank you Sir!! I was always the shy girl at the back of the class. Leaning in closer to hear the other girls talking about wanking their boyfriends off and having to Google the meaning when I got home. Once I found out the meaning there was nothing else to do but try it out. From that moment on I was so curious about all aspects of sex.My first few boyfriends taught me a lot about hand jobs and blowjobs, swallowing cum and having my pussy eaten, but it...

2 years ago
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I was a wartime TV for the US Army

‘I was a Wartime Transvestite for Uncle Sam!               TJ Ryder                                            Chapter 1           Reform School Romance!     I couldn’t believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II.    I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another old geezer in an assisted care center who if he ever had...

4 years ago
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Wartime France

The funeral was a gloomy affair as funerals go. I am somewhat irreverent and remember clearly my twin brother and I giggling all through my Uncle’s funeral because his widow had the price ticket still dangling from the back of her hat. John and I shared a sense of mischief and humour. At our Grandfather’s funeral, we’d been unable to look at each other during the hymn ‘Praise my soul the king of heaven,’ because John had written an alternative verse that was utterly filthy and we both knew what...

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2 years ago
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Wartime Passion

A few years ago, my wife was having a midlife crisis while I was away serving in Iraq. She was both lonely and horny. She had been without me for nearly 8 months and I still had four more months to go on my tour of duty. Char is an attractive 40 year old woman, 5'8" tall with blonde hair and green eyes. She keeps herself in great shape and still has a body to prove it, 36-30-36. Our sex life is absolutely wonderful when I am there, and I would not change a thing. She is a Hottie and we are...

1 year ago
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I was a wartime TV for the US Army

  'I was a Wartime Transvestite for Uncle Sam!              TJ Ryder                                          Chapter 1          Reform School Romance!    I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being hisfavorite grand nephew was an old diary from World War II.   I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another oldgeezer in an assisted care center who if he ever had anythinghad...

Crossdressing
4 years ago
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Surprising FirstTimers

Friday night had arrived and as usual, I was at the sex club early to assume duties as a greeter for any first-time visitors. Quickly, I changed into black latex shorts and a pair of black boots ready for the night to begin. After setting up the equipment in the dungeon I returned to the bar waiting for the guests to arrive.Slowly the room began to fill with the usual mix of friendly faces. By now I was well known to the clientele and almost everyone greeted me with a hug, handshake or kiss. As...

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4 years ago
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Summertime Fun0

Summertime Fun After my divorce I got my daughter every other weekend and for the entire summer. Now that she was fourteen and developing quite nicely I was enjoying her even more. I also indulged her desire for sexy revealing clothing, since her mother wouldn’t. Holly was pleased that I had purchased a summer home alone the beach. We used to go to the ocean when we were still a family. Another thing that I did to piss my wife off after the divorce. It was a very nice place and I...

1 year ago
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Summertime Chapter One

Summertime: Chapter 1 By Tommie Summertime, and the living was easy. I had just graduated college and I was home for the summer. My parents were on vacation and I had the house to myself. I had settled into a relaxed routine. Up late, lazy breakfast, a little bit of work on the computer to keep my hand in for the programmer's job I was starting in the fall. Then, as often as not, a lazy afternoon reading in the back yard before soccer training in the evening. Soccer had paid my...

3 years ago
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Club Orb First Timers

This is my third transformation story but my first straight up transgender romp. I'm a fairly new author and I'm striving to improve. Hopefully the story will be enjoyable and thank you for reading. Club Orb: First Timers "C'mon! Please come to the club, I know it's not your thing but I swear you'll have a lot of fun. My personal guarantee -- we will both get laid." Danny attempted to bribe his extremely undersexed buddy Jack. "That's... not really something you can...

4 years ago
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Slaves First Double Penetration

I enter the living-room where you and Jack are sitting on the couch. Jask has very pale almost red skin compared to your deep chocolate color. And short blonde hair. He is not what I would call a good looking man but you had told me before I arrived that he was your closest friend and you wanted me to please both of you tonight. I sit close to you and you put your arm around me. After a little small talk you order me to the bathroom to undress. I come out and stand nude in front of you, hands...

2 years ago
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TimeLine chapter 1

Like Billy Pilgrim, John and Amy have become unstuck in time. Unlike Billy Pilgrim, theirs is a fate more akin to eternal recurrence. Fate, for sure, had intended more for them. The timeline was diverted and the two were paying the price: Amy for her stubborn obstinance; John for his arrogance. For her stubborn behavior, Amy was dealt a hand similar to that of Sisyphus. She was placed upon life's treadmill: forever struggling to make ends meet; forever struggling to find her way...

3 years ago
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TimeLine chapter 2

When did the first, unfortunate fork in the timeline take place? Each attempt to divert the timeline back onto its true, fateful path has resulted in failure. Time is growing short, and an altered fate nearer. Each manipulation has resulted in this fate's end time grower slightly nearer or farther, but no significant change has occurred. Given that recursion is the problem, perhaps it is also the solution. Perhaps. The two share a weakness -- each knows on some level what needs to...

2 years ago
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My first double penetration

It all went like Roger and I planned. Let me tell you about me first. I've got long, long dark hair, all the way down to my tiny waist. Good-size tits, not the world's biggest but all natural. Nice curvy hips and firm ass, I'm not crazy about my thighs but when they're jackknifed back against my shoulders it doesn't matter how they look, does it?Roger was a big guy, he was a celebrity bodyguard...never mind whose, I didn't care about that, I liked HIM better. Six foot two, thickest cock I ever...

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