I, Jessica Whitmore, better known as Jesse, was born into a life of privilege and money. Like most children born to wealthy parents, I was given everything I wanted, whether I deserved it or not. And, like the majority of those children, I have attended a private school all of my life. I am now in my senior year and just turned eighteen. I have about two months of school left and I can't wait until I'm free.

Like most private schools, ours has one of those stupid dress codes. The boys all dress alike in dark blue dress pants and matching jacket with our school emblem, white button-up shirt, checkered tie, and black shoes. While us girls dress in the same jacket, shirt, and tie, but we wear checkered skirts that match our ties and a different type of dress shoe. Although, I'm quite sure that when the board of directors started letting girls attend school here, some one hundred and fifty odd years ago, they never dreamt that the skirts would be as short as they are today. I'm also sure everyone can just picture how sexy and provocative us girls look in them.

There is one teacher here that has never tried to hide his interest in the girls' short skirts and that is Mr. Larry Raney, the World History teacher. It was rumored that Mr. Raney liked to "tutor" those "of age" girls that were having trouble in his classes. It was rumored that he was suppose to be a "huge" help to all of the girls. Needless to say, all of us girls had a fun time teasing him by showing just a little more skin than is allowed while we're in uniform. A few of us older girls on the front row have even come to class with no panties on when it's test days. You know, just to give him a good view to look at while we're all taking our test.

It was a Friday evening and I sat in my last class of the day; Mr. Raney's. I had big plans for the weekend and couldn't wait for the bell to ring. Mr. Raney sat behind his desk grading the tests that had already been turned in. As usual, mine had been one of the last ones turned in and I watched as he shook his head in disgust as he graded them. "Miss Whitmore," he said looking up, "I would like for you to stay after class, please." "Damn," I thought to myself, "there goes to start of my weekend."

In a few short minutes the bell rang. I waited until everyone had left the room before I approached the desk. "You wanted to see me, Mr. Raney," I said. "Yes," he said as he walked to the door and closed it. "It's about your grades." "I'm doing the best I can," I protested, "but I've never liked history, it all seems so boring to me." "Maybe there's a way I can help you," he said smiling at me. I wanted to burst out laughing at the thoughts going through my mind about how Mr. Raney was going to "help" me.

Mr. Raney was far from being the best looking of men. He was a short, balding, middle-aged, over weight man. He was the last thing that a teenage girl like myself would find the least bit sexy. At five foot seven, even I was taller than him. Ever time he would talk to me; he talked to my chest, which was eye level for him.

"How can you help me," I asked him. "By giving you a little extra tutoring," he said. "I've already cleared it with the Head Master for us to meet in my office after hours, starting today." "Awww," I groaned, "can't we wait until Monday to start? I've got plans for tonight." "Well, you're going to have to cancel them," he said, looking at me sternly. "Meet me at six this evening at the front of the building where my office is. We'll do the studying in my office."

I meet Mr. Raney shortly before six that evening where he said too. His office was one of the few on the deserted side of the campus. I walked about three steps behind him as we headed to his office. He had to unlock three doors before reaching his inner office. "Now," he said as he sat his brief case down on the floor next to the desk, "let's get busy. I see that you're still in your school uniform." A broad grin spread across his face as he said the last comment. "Yes," I said grudgingly, "I thought it best since you're going to be tutoring me."

I don't wear any panties and it just occurred to me that I hadn't put any on before meeting Mr. Raney. After removing my coat, I also noticed that I had forgot to button back up the top three buttons of my shirt and to put my tie back on; two regulations that were strictly enforced. "Oh well," I thought as I sat down next to him at the round table in his office. He had me to start correcting my test as he looked on.

We had been setting there a few minutes when I felt his hand on my leg. At first I thought that it was my imagination because I no longer felt it. But then, I felt the front of my skirt lift and his hand touch my uncovered pussy. The roughness of his finger felt good against my shaved pussy and I spread my legs wider. Seeing that I was enjoying his touch, he gently rubbed my clit. "MMM," I moaned, "That feels good."

Now I had never had sex with a boy, but I had played around with them. I had given them blow jobs and had had them to eat me, but I had yet to lose my virginity. I don't know why, but I desperately wanted it to be Mr. Raney that took it from me.

Reaching above my head, I removed the clip that held my long strawberry blonde hair. Mr. Raney continued to rub my clit as he watched me pull my shirt from my skirt and slowly finished unbuttoning it. I pushed it aside, showing him my lacy, see through white bra and flat stomach. I then reached behind me and unsnapped it and pushed it up. "Oh Jesse," he moaned as he stared at my small breasts, "there beautiful. Just the way I like them; small." Still rubbing my clit, he leaned down and took a tit into his mouth. "Mr. Raney," I moaned as I rubbed his bald head. For several minutes I sat laid back in the chair as Mr. Raney slowly rubbed my clit and sucked on and pulled at first one tit and then the other. I couldn't stop moaning and squirming.

Mr. Raney slipped a finger into my pussy and smiled. "Have you ever been with a boy," he asked a look of lust in his eyes as he did. "No," I said shyly, "but I have a feeling that I'm about to have a man in me real soon." "I like the sound of that," he said.

Sitting back up in his chair, Mr. Raney unbuttoned and removed his shirt. Normally I would have been turned off by his very hairy and very gray chest and VERY LARGE stomach, but not now. I was strangely turned on by them and wanted him very much.

After he stood up, I eagerly undid the belt that held his pants up. It didn't take me long to pull his pants down and discover the truth about all the rumors I had heard about him. Let's just say they're all true. Mr. Raney's VERY thick, seven and a half inch cock sprang out at me as soon as I pulled his boxers down. Eagerly I took it into my mouth and sucked on it. My forehead would hit his large stomach as I would take him all the way into my mouth and throat. "Oh that's it, Jesse," he hissed as his hand pushed me deeper and deeper onto him. After gagging twice, he let go and told me to set up on his desk.

I pulled my short skirt up so that he could watch my naked ass as I walked across the room too his desk. Mr. Raney was just a few steps behind me with his pants around his thighs. With my school uniform skirt still lifted, I sat down on his low desk. Stroking his hard cock, Mr. Raney sat his rather large, naked ass down into the office chair behind his desk. I leaned back onto my hands and spread my legs wide. Mr. Raney began to slowly lick up my wet opening to my swollen clit.

"Oh God," I screamed. Again his tongue moved up my pussy, causing me to again scream with pleasure. "Yes," I panted, "that's it, Mr. Raney. Right there. Right there. Oh God, yeah." I pushed his face closer to my pussy with my right hand and rubbed it in his face. His hands reached up to my thighs and held me still while his tongue pushed into me. "I"m cumming," I panted. "Oh Mr. Raney, I'm cumming." With that, a gush of love juices exploded from me and all over his tongue.

"Oh Jesse," he moaned as he sat back in his chair. my pussy juices gleaming on his face. Standing up, he pulled my hips closer to the edge of the desk. "Are you ready for a man," he asked lustfully. "Yes," I panted, still recovering from my orgasm. I could feel the bulbous head of his huge cock as it penetrated my pussy. I moaned as he slowly pushed in me a few inches before pulling back out. His next push was deeper and hurt like hell. "Ow," I winched as he stopped and then pulled out.

"One more, Jesse," he said, smiling down as me. "One more and I'll pop that perfect cherry of yours." No sooner had he said it, Mr. Raney pushed back in, all the way this time. It felt as if I had just been ripped apart as he shaddered my hyman. "Oh sweet Jesus," he called out as he shattered it. "Oohh," I cried, "that hurts." "Shhh Jesse," he whispered, "it'll feel good once I start moving in you."

Mr. Raney was right. Once he started to pull in and out of me, I just couldn't get enough. I began to move in rhythm with him. Soon I was moaning and panting with ecstasy. "Mr. Raney," I panted, wrapping my arms around his chubby neck. "Oh Mr. Raney. Oh, that feels sooo good. Oh, yes. Don't stop. Don't stop. Pleeease don't stop."

His large hips rocked as his huge cock moved in me. His large stomach pressed forcefully against me each time he pushed in. Pulling out he said, "Lean over my desk, Jesse." I quickly hopped down and bent over his desk. My small round ass jiggled as he pushed himself forcefully back into me. It was then that I noticed the large mirror in front of me on the other side of the room. I was able to see Mr. Raney behind me; fucking my virgin pussy with his huge dick.

"I'm gonna fuck you, Jesse," he said as he grabbed my hair and began to forcefully fuck me. "I've wanted to fuck you ever since I first saw your pussy in my class. You are always teasing me by not wearing panties and spreading your legs in front of my desk. Now, you'll get the punishment you deserve." I screamed with pleasure as he pulled my hair harder and harder and rammed his cock deeper and deeper into me. Soon I felt him pull out and a hot load of his cum hit my back.

Looking into the mirror again, I watched as Mr. Raney wiped the sweat from his forehead. "Oh damn it, Jesse," he panted as he fell back into his chair, "some more of these tutoring sessions before you graduate and I believe your grade will improve greatly. How about Monday night around the same time?"
"MMM," I purred, "Sounds great to me."

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