This is my first entry, I write stories, but this is my first sex story.
The chains and spikes on Dereks leather jacket clinked loudly and abnoxiously as he waltzed down the hallway in his school. He was a senior in high school, but at this point he saw no reason to graduate, having a broken family and working at a mechanics shop after school. He wa paid pretty good money, but knew that he couldn't keep the job forever.
As Derek passed a large plexi-glass window on his left, he slowed down and looked in. Behind the glass at a desk was a fairly old secretary filing her nails through her bi-focals. The phone rang and she dropped the filer on the desk and picked up the reciever and began talking cheerily through it to the person on the other end. Derek looked passed her at the door.
A smile cept onto the corner of Dereks mouth as he pictured the beautiful Mr. Matheson in her usual short dress skirt and suit top. She usually left the top two buttons of her blouse unbottoned, always leaving much to the imagination of Derek at night when he would jerk off. She had nice full breasts, just under D cups, and her ass was perfectly round.
Derek always imagined her sitting on top of him, bouncing up and down while squeeling in delight and ecstasy. Derek stopped at a wooden door next to the plexi-glass window, and opened it. He walked in and the secretary looked at him. She let the phone drop a little and asked annoyed, "Can I help you young man?"
"Ms. Matheson sent a note to my class. Said she needed to see me."
"Okay then. Go on in." the secretary replied as she put the phone back to her mouth to resume the pointless conversation she had been having.
Derek walked to the door of Ms. Mathesons office, and knocked quietly, then walked in, half his brain hoping to see her doing something naughty. What he saw took him by complete surprise. Ms. Matheson had her back to Derek, and like usual he took a long look at her beautiful round ass. He licked his lips as his cock began to grow in size as his imagination ran to their usual thoughts of fucking her.
"Close the door behind you Mr. Johnson." He did as he was told without any hesitation, then turned back to look at his principal. She was facing him now, and he noticed that their was a third button undone on an already low cut blouse.
He saw the edges of her bright red bra as her tits stuck out what seemed to be even farther than usual. She looked him up and down, and he thought he saw her let eyebrow raise a little when she saw the bulge in his pants. "Take a seat Derek. Do you know why I called you to my office today?"
"No ma'am, I don't. For once I actually didn't even do anything wrong."
"Your right, Derek. But you have done alot wrong in your career in my high school. But I think I have a certain... special disciplinary type that may change your mind about your future so that you want to succeed in life."
Derek was curious, but somewhat scared, knowing that Ms. Matheson has had a history of extreme anger and brutal acts of discipline. She leaned forward, and Derek got a clear view down her blouse, her slightly milky white cleavage almost glowing. The bulge in his pants jumped, and Ms. Matheson clearly saw it. She smiled and continued to sit down in her swivel chair.
"I see you like my outift today, Derek. Would you like to see more?" she asked cheesily.
"Fuck ya I would." Derek blurted stupidly.
"Of course you would. But I have one condition. You have to complete high school. You'll have... perks of course every school day."
"Anything you say. God your fucking gorgeous."
"Why thank you Derek." She seductively lifted her pearl white hand and ran it slowly down her tits, moaning slightly in pleasure. Derek saw little wet spots growing over her nipples as she ran her hand down her stomach and began to touch herself. Derek saw her arm begin to move faster and faster as she masturbated furiously.
He began to stand to his feet to walk over to her and help her out, but she stopped and held her hand up to stop him. "Sit...sit back down Derek. Let me finish, then we will begin your lesson."
Derek sat back down on the armless chair and unzipped his pants. He opened his boxers up and his cock sprang to attention, pre-cum already soaking the top. He began to run his rough hands up and down his 8 inch cock as he watched his beautiful principal masterbate in front of him. She groaned and gasped for air as she continued her experience.
Her breathing quickened and then she gasped one last time and held her breathe. She shuddered as she let out the breathe, her silent orgasm over. She opened her eyes and saw derek pleasing himself and she smiled. "Well, well well. It seems you didn't want to wait. Oh well."
She rose to her feet, and Derek saw a huge wet spot showing at the front of her skirt. She walked towards him slowly, her hips swaying seductively. She stopped right in front of him and hiked up her skirt. Derek saw she wasn't wearing any panties, and her perfect pink mound was completely shaved bald. She straddled him and sat on his lap. His cock was pushed almost painfully against her tight abs. She flipped her hair to the side and leaned forward and put her big round lips to Dereks. They explored each others mouths with their tongues, and Dereks hands found their way to her waist. His right hand slowly ascended up to left tit and he began to rub it softly. She moaned and she egan to lactate again. She began to undo her blouse and Derek helped. Ms. Matheson took her blouse off completely, and left her big round tits exposed with her bright red bra covering them teasingly. Derek wrapped his arms aorund to her back and began to undo her bra.
He had much experience unhooking bras, so he got it off of her within seconds. Her beautful round tits bounced down a little bit, and Derek almost came right there. He began to rub them softly in circular motions and she tilted her head back and moaned in ecstasy. He leaned forward and suckled on her left tit. She began to grind and rock her hips back and forth, almost bringing Derek to the point of orgasm again. He dropped his hands down to her perfect round ass and lifted her up.
She was at first confused, then she understood and put her feet on the ground and stood there for a few seconds. Derek dropped one hand to his cock and Ms. Matheson began to sit down again. Derek guided his cock t her pussy lips, and they slowly parted and the head of his cock entered Ms. Mathesons love box. She sat down completely, and began to rock her hips again. Derek moaned in pleasure, and Ms. Matheson lifted herself up a little, and dropped herself down on his cock again, impaling herself. They continued like this for a few minutes, before Derek was to the point of cumming.
"Oh my god. I'm gonna cum. Oh fuck. OH FUCK!"
"Cum inside me Derek, come inside your principal."
Derek promptly complied, and came hard inside of her. They continued to fuck hard for a few moments afterward though. Dereks cock began to shrink inside of her, but she continued to girate her hips. They kissed some more, and Ms. Matheson finally rose to her feet and put on her bra. She began to clean up and but on her blouse, but Derek rose to his feet and stopped her before she put on her shirt. He took her by the shoulders, and guided her to the swivel chair behind her deska nd sat her down.
"I don't believe you had an orgasm with me Ms. Matheson."
Derek lifted her skirt and reached toward her pussy. He rubbed his thumb softly around her cunt, and then entered his middle finger into her. She gasped and tensed up, but shortly relaxed and gave in to the touches of the 18 year old man in between ehr legs.
He moved his finger in and out of her pussy lips, and then dropped his face down in between her thighs. He licked around her pussy lips, at the same path his thumb had gone, and then began to lap at her pussy hungrily, savoring her musky taste.
He entered his tongue into her pussy, and she gasped loudly. She moved her hips and dropped her hand down to her pussy and rubbed the top of it as Derek continued to lap at her pussy.
She came hard all fo a sudden, giving no warning,a dn her juices flowed onto Dereks face. He rose a little bit and kissed Ms. Matheson on the lips, giving her a taste of her own pussy. She then rose to her feet, and pulled Derek to his. His cock was hard again, and at least an inch longer than before. She got down on her knees and began to slide her soft hands up and down his shaft.
She leaned her head towards the head of his cock, and breathed hotly onto it, turning Derekon even more. She stuck out her tongue and licked all around the head slowly. She elaned forward a ltitle more and kissed the head of his cock. She kissed it a few more times, and then took his cock fully in ehr mouth. She swished her tongue all around his cock and her head bobbed up down as she sucked furiously on his cock. She felt his balls tighten as he came closr to cumming, but she let go of his cock, and pulled it out of her mouth, just before he came.
Derek almost screamed in pain when she stopped, and she rose to her feet. "What the fuck? You can;t give me blue balls!"
"Don't worry baby, I just need you inside me once more."
Derek smiled as she grasped his cock firmly and stepped backwards towards her desk. She hiked up her skirt more and sat down on the desk. She guided Dereks cock towards her pussy, and he entered her slowly. She inhaled slowly as he entered her, and her breathe began to shorten and get louder as he moved in and out of her. She laid back on her desk, and let Derek go at it himself. He thrust in and out of her sweet pussy quickly, and his speed increased. Ripples went up and down her soft round ass, and went up to her beautiful milky tits, as she unded her bra and let it drop again.
Her tits jiggled wildly as Derek plunged in and out of her hard. She began to moan loudly, and it crescendoed to a painful yelps as Derek went deeper and deeper. "Oh god Derek. It hurts. Slow down, don't go so deep. You're hurting me." Derek smiled and went even faster. He saw that no matter how much it hurt her, she liked it more and more.
He kept going and going, still not ready to come even after 12 minutes of hardcore fucking. Ms. Matheson came for the second time since she laid down on the desk, and finally Derek was getting to the point of cumming.
"Don't cum inside of me this time Derek. I can't risk getting pregnant, You already came in me once, that was risk enough."
"Yes ma'am." he replied.
His balls tightened and he felt the cum inside of him begin its ascent to the world. He withdrew his cock from her pussy and began to stroke his cock. Load after load of hot creamy cum spurted from his cock and onto Ms. Mathesons tight stomach. The cum just kept unloading from his cock onto her, and she reached down and rubbed he head of his cock. IT finally stopped spurting from his head, and she rubbed the cum around on her stomach.
"Oh god, that was amazing Derek. That... was fuckin AMAZING!" she screamed the word amazing the second time, and Derek smiled widely.
He cleaned off his cock, and put it away in his pants, and Ms. Matheson was still laying on the desk, rubbing the cum around on her stomach. Finally she came to her senses and leaned up and cleaned herself off. She put her clothes back on and looked at Derek. "Now do you ike school?"
Derek smiled and walked over to her. He wrapped his arm around her waist and pulled her into him hard. He kissed her roughly on the lips and then let go and turned to the door. He opened the door, but before he stepped outside, he turned back to her. "I love school." He walked out the door, and closed it behind him.