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."

__________________
It's only funny until someone gets hurt, then it's hilarious!

All weekend long, my roommates tried to get me to tell them what had happened. Knowing that one of them was a big blabber-mouth, all I would tell them was that he had had me correct my test and we went over some of my homework papers. I knew that if she was to ever find out, she would have it all over the school and both Mr. Raney and I would be in serious trouble.

On Monday, my classes seemed to pass very slowly. I didn't wear any panties today so that Mr. Raney could get a peek of what he would be having again tonight. Instead of doing his usual pacing around the room, he stayed mostly in front of the room where he could clearly see up my uniform skirt. The bell signaling the end of the day rang.

As I was leaving Mr. Raney's class, he called, "Wait a minute please, Miss Whitmore." Stopping just short of the door, I told my friends to go on and that I would catch up. Once they had left, I walked back to his desk. Mr. Raney stuffed his papers into his brief case and said, "I just wanted to remind you of our tutoring session this evening at six. Also, you don't have to wear your uniform tonight. You can wear what you like." Looking up at me, he gave me a devilish grin and a chuckle before saying, "Dare I say, whatever it is you wear, you won't be in it very long."

To pass the time until six, I finish up what little homework I had, showered and then dressed. Since it was mid spring, I put on a pair of denim shorts and a pink tank top with nothing underneath. When we weren't in class, and on our own time, we could wear what we wanted. It was only when we were in class, or some school function, that our uniforms had to be in correct order.

It was going on six when I slipped my sandals on and headed for Mr. Raney's office. Just like before, I met him outside of his building a little before six. Tonight he was dressed in blue jeans, t-shirt, and sandals, which by the way, made him look even heavier. With his briefcase in hand, mostly for pretense purposes, we once again went through the three doors leading to his office. Once inside, Mr. Raney sat the briefcase down by his desk. I sat down on the small couch at the back of his office.

"I've thought about you all weekend," he said as he approached me, pulling his t-shirt off as he did. Once again, looking at his graying chest hair and large round stomach began to turn me and I could feel my pussy moistening. Reaching the couch, he sat down next to me. "Sit on my lap," he said, patting his leg.

Placing a knee on each side of him, I slowly lowered myself onto his lap. My breasts now directly in his face. I had become so excited that my nipples poked through the lose fabric holding them in. Mr. Raney rubbed my tits through the fabric, occasionally pinching the nipple. "MMM," I moaned as I gyrated my hips, "That feels good." His hands slipped from my breasts, down my flat stomach, and then back up my shirt. I raised my hands over my head as he removed my shirt, sucking on my tits as he pulled it over my head and off arms.

"Oh yeah," Mr. Raney lowly said, "There’s the little titties that I've been thinking of." I moaned as he roughly rubbed them. "Yeah," he said, "you like it rough don't you Jesse." "Yes," I moaned. "It feels so good." I began to grind my pussy onto his now hard cock through the fabric that we each wore. "Oh fuck," he gasped. "You know just how to tease a man, don't you, you little slut?"

Sliding back on his lap, I reached down and undone his jeans. "Let me take them off," I begged. Mr. Raney smiled as he watched me remove his pants, underwear, and sandals. With him still standing , I knelt before him and stroked his hard seven and half inch cock before placing it in my mouth. "Ahhh," he moaned as watched my head bobbing up and down on his thick shaft. "That's it Jesse. Just like that. Yeah, just like that."

I increased my pace and suction on him as Mr. Raney placed his hand on my head and forcefully fucked my mouth. Each push nearly made me gag. "Oh, you little bitch," he moaned, "you're gonna make me cum." A few more rough strokes and I could feel his hot, salty seed hitting the back of my throat. His dick remained deep in my throat, causing me swallow ever drop. "Oh Jesse," he said as he fell back onto the couch, "you're the first student that has swallowed it. The others all gag it back up." Patting the back of the couch next to him, he continued, "Get up here. I want to taste your sweet pussy again while I rest up."

I sat on the back of the couch as he rubbed my pussy through my shorts. "I can tell that you want to have my cock in you again," Mr. Raney said smiling lustfully. "Oh God yes," I moaned as I raised my hips up slightly to let him pull my shorts off. "MMM," he moaned as he spread my legs wide apart. "Look at that perfect pussy," he said as he rubbed my clit.

"MMM Mr. Raney," I moaned. Looking down, I watched him as he rubbed my clit. "All weekend long," I continued, "I've wanted to feel your hands on me again; touching and fondling me." I moaned again as his tongue slowly licked up my wet pussy, flicking my clit once he reached it. "Oh fuck, Mr. Raney," I gasped. Again his tongue made a swipe up my love hole. "God, does that feel good," I again panted. His tongue now quickly flicked at my swollen clit causing me climax. "MMM Delicious," he said as he tasted the juices flowing from me.

Mr. Raney slipped first one and then two fingers into my wet, steaming pussy. I moaned as his thumb rubbed my clit as his fingers continued to move in me. "Fuck me, Mr. Raney," I begged. "Oh please fuck me. I've got to feel your cock in me." "You do, huh," he said, continuing what he was doing. "What if I want to make you wait?" "Please, Mr. Raney," I pleaded again, sounding more desperate this time. "I need you in me. Please, I'm begging you." Mr. Raney was silent for several seconds as he continued to rub and finger me. Finally he said, "Lay down on the couch."

I eagerly lay back onto the couch, spreading my legs wide. I placed one foot on the floor and one on the back of the couch. Mr. Raney lay on top of me and smiled down at me as he pushed his cock into me. "Oh, you tight little slut," he moaned as all of his seven and half inches slid into my dripping wet pussy. "Oh Mr. Raney," I panted, "You still feel so huge. God, I love the feel of your cock in me."

Mr. Raney didn't speak, but started to slowly move in me. Pulling his dick nearly all the way out, he would then ram it back in roughly. "Oh yes," I would scream each time he did this. "Oh yeah, Jesse," he finally said, "you're the tightest student that I've ever fucked. Shit, I love the tightness of your pussy." I came as he rammed his cock into me one last time before pulling completely out. He then sat down on the couch. "Ride me, Jesse," he said, grabbing my hand and pulling me up to him. "Ride me."

Spreading his legs, he turned me around so that I was in reverse cowgirl. Slowly at first, I raised and lowered my pussy on his cock, but the more I did, the better it felt and the faster I went. Soon I was cumming again and again as I rode him through four orgasms, screaming "Oh God Yeah" each time.

Pushing me off of him, I fell over onto the couch and pulled myself up so that I was leaned over the back of the couch with my ass pointed towards him. Getting behind me, he spread my legs wider apart and knelt down on the couch. I could again feel his cock pushing deep into me. Grabbing my long strawberry blonde, he pulled back hard until I was looking up at the ceiling.
"Oh God," I gasped as his roughness made me cum.

"You're nothing but a little teasing cunt, aren't you," Mr. Raney smirkishly asked as he started to slowly fuck me. I could feel his large stomach hitting my ass as he pushed deeply into me. "Just a fucking cunt" His pace slowly increased until he was slamming his cock into me, screaming at me to "take it, bitch, take it". Over and over I screamed "yes" as he rammed his cock into me. I came several times as he fucked me like this.

Soon Mr. Raney let out a groan and I felt him release in me. "Oh fuck, Jesse," he moaned as he released my hair and grabbed my hips, pushing him deeper into me. My shoulders collapsed onto the back of the couch as he continued to hold my hips in place. "Cumming in you felt so good," he panted.

It was then that it occurred to me then that Mr. Raney had just came in me. He wasn't wearing a condom and I wasn't on the pill either. "Oh shit," I said as I tried to pull off of him. "Neither of us has protection of any kind." "Don't worry," he said, pulling me back to him, "I can't have kids. I've never been able too due to a childhood accident." After hearing this, I relaxed and wiggled my hips on him. For several minutes, we stayed in this position.

"I'll see you again," he said as we dressed. "I have ball games the next two nights to cheer at," I said. "MMM," he moaned lustfully. "Why don't you come by Wednesday night while you're still in your cheerleader uniform? I'll be waiting outside the building for you after the game." "MMM Sounds good," I purred as we walked out of his office.

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It's only funny until someone gets hurt, then it's hilarious!

Tuesday and Wednesday passed by rather quickly. Before the game, all of us cheerleaders went out onto the field to get the crowd warmed up. I couldn't believe my eyes when I looked up into the bleachers and saw Mr. Raney directly in front of me, about four seats up.

All during the game, I put a little more "umph" into my moves. You know, swinging my hips a little more, thrusting my tits our further, making my moves a little more provocative than usual. I could tell by the way Mr. Raney was looking at me as the game finished, there would be no going back to his office. He was going to fuck me just as soon as he got the chance.

When I came out of the stadium, Mr. Raney was talking with another teacher. To make it look good, I went over and asked him if I could talk to him about a homework assignment. Together we walked off to a secluded area of the stadium's outside. Finding a dark stairway with a railing, Mr. Raney wasted no time in feeling me up as he kissed me.

"We'll have to make this one quick," he said as he hurriedly undone his pants. "I don't care," I said as I too quickly removed my red uniform bloomers, "just as long as I get to have your cock in me, it'll be good." My red and white pleated skirt twirled as I quickly turned around and leaned over the railing, spreading my legs wide. I moaned as Mr. Raney rammed his hard, thick, seven and half inch cock into me. His right hand covered my mouth as I let out a low scream. His left one grabbed and rubbed a tit through my sleeveless uniform top.

"MMM," I moaned as he began to slowly fuck me. His hand was still on my mouth as he lowly whispered "shhh". It was then that I heard someone coming around the building. This didn't seem to faze Mr. Raney as he continued to slowly moved in me. I had to admit that the idea of being caught with my legs spread and Mr. Raney's cock buried deep in me turned me on even more.

I began to move in rythem with him. We slowly, and quitely, fuck as the Head Master and Members of the Board passed by. We were so far back into the shadows of the stairway that they didn't even see us there. The Head Master heard my moan and pointed us out that one of the football players must be celebrating with his girlfriend.

The close call heighten our desire and we bagan to move faster in rythem. Mr. Raney's hand was still covering my mouth as I let out a squeel of pleasure as I came. "Oh Jesse," he lowly moaned. As the sound of the voices died away, the only sound was that of Mr. Raney's balls slapping my pussy as he fucked me. Grabbing my hips, he gave a long, low groan and came. A few more strokes and my pussy milked his balls of their cum. "Damn that was good," he panted as he pulled out. "Definately," I said cooing as I put my uniform bloomers back on.

Mr. Raney and I continued to have out "tutoring sessions" until I graduated. I'm sure that there has been, and will be, several girls who will be needing "extra tutoring" from him. I'm just happy that I was one of them.

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It's only funny until someone gets hurt, then it's hilarious!