tagMatureHillary

Hillary

byD.C. Roi©

Introduction:

Last summer the school district where I’ve worked as a permanent substitute teacher for a couple of years hired me to teach several make-up classes. One of them was an English class for a few students who would have graduated but for failing English. There were four students in the class, three boys and one girl, Hillary Watkins. Hillary is a bright girl, but her interest in social activities far exceeds her interest in doing class work. Her parents wanted her to go to college and had somehow arranged to get her admitted to a small New England teachers college. The only problem was, she needed her high school diploma and didn’t have enough credits to get it. Her parents, though indulgent, did expect her to do the work, much to Hillary’s dismay.

Hillary is eighteen, has shoulder-length brown hair she wears straight, and while she isn’t super-attractive, she certainly isn’t homely. The phrase is over-worked, but I guess you could say she has “All-American Girl” looks. She probably weighs a hundred thirty or so pounds, that weight is well distributed, and she generally dresses in ways that make sure the male members of society know that weight is very well distributed. I heard she was dating the captain of the football team. She often seems a bit snobbish, but when she wants to, she can be quite personable.
Hillary was exercising her charms considerably when, unannounced, she stopped in at my house one afternoon an hour or so after the end of summer school. I happened to be home alone because my wife and kids were at her family’s beach house on the coast of Maine. My wife’s great-grandfather built the beach house and family tradition is that the entire family gathers there for at least a month every summer. Believe me, spending a month in a small house filled with people who give new meaning to the word “contentious” has never been one of my favorite things, so I jumped at the opportunity to teach summer school. That meant I only had to go to Maine on the weekend, which suited me just fine.

As it turned out, Hillary came to my house hoping she might be able to accomplish with feminine wiles what she hadn’t been able to accomplish with her half-hearted attempts at schoolwork, namely getting a passing grade. She learned she was wrong about that, and learned some other things, too. Why don’t I let her tell you? Here’s the paper she wrote to complete the assignment I gave her that day.

* * * * * * * * * *

What I Learned This Summer
By
Hillary Watkins

This is without question the weirdest and wildest school assignment I ever had in my life. I messed around in school a lot. I know that, but I never thought I wouldn’t graduate. I mean, it isn’t like I’m stupid or anything, it’s just that there are so many other things I needed to do that sometimes I didn’t get all my homework done. Anyhow, Mrs. Fraley, the English teacher, had the nerve to give me a failing grade, which meant I had to go to summer school before I could get my diploma. What a bummer!

There were three boys in the summer school class with me; really creepy guys. I mean, I could understand why they didn’t pass. They let me alone because they knew my boyfriend Dave would break them in two if they messed with me. Mr. Dornier was the teacher. I know him because he substitute teaches a lot. He’s a little younger than my parents, but not much. He has a daughter who just started in Middle School, I think.

Anyhow, a couple of days ago, Mr. Dornier told me I wasn’t going to pass the makeup class if I didn’t start “buckling down,” as he put it. I couldn’t believe it! I mean, it’s bad enough I have to do go to summer school, then the teacher has to go and be a jerk! I figured summer school was just a formality, you know?

I was really pissed at first. After all, it’s bad enough I have to take the darn class, then Mr. Dornier tells me he’s going to fail me! Jeezum! I mean, it sucks to spend prime party time sitting at my damn computer typing up papers and doing homework assignments. Then I had an idea. I’ve seen the way Mr. D looks at me. I think I’ve got a pretty good body – Dave and other guys I’ve gone out with tell me I do, anyhow – and I could tell from the way he looked at me that Mr. D thought so, too. Some of the my friends are “creeped out” by the way some of the male teachers look at them, but not me. I kinda like that guys think I’ve got a good body and that I’m pretty, you know?

Well, I thought that since Mr. D seemed to like the way I looked, maybe I could convince him to, you know, do me a favor. I heard him talking to one of the other teachers about how his wife and daughter were over in New Hampshire or Maine someplace, which meant if I went to his house I would catch him alone. The way I figured it, I wasn’t going to get into trouble for going there, but depending on how things went, it was possible he could get in trouble because he was alone in his house with me. I mean, don’t get me wrong. I didn’t plan to blackmail him or anything, but I figured maybe if I showed up at his place, I could talk him into being nicer to me. Well…

I was wearing the same outfit I’d worn to school that day, a pink sleeveless cotton summer dress – a mini. It buttons down the front and is kind of tight over my breasts. I think it makes them look bigger than they really are. And it’s A-line, so it isn’t tight over my butt, which is a little bigger than I’d like it to be. It’s made of really soft, kinda stretchy fabric, though. I like it and, from the way Mr. D was looking at me in class, I was pretty sure he liked it, too.

Mr. D lives outside of town on a dirt road. His house is about a mile from his nearest neighbor and sits at the end of a really long driveway. I parked behind the house next to his car, went to the back door, and since there wasn’t any doorbell, I knocked on the door.

When Mr. D answered the door, his eyes widened a little, but he didn’t look as surprised as I thought he would. He smiled at me like he always does and said, “Hello, Hillary, what brings you to my house this afternoon?”

The fact that he wasn’t nervous made me nervous, if that makes any sense. “Ah…Mr. Dornier…um…can I, ah, talk to you about my grade?” I’m not sure why I couldn’t talk. So much for being cool and taking charge, huh? I do know Mr. D wasn’t acting like I figured he would.

Mr. D smiled at me. The way he looked at me, it was as if he knew something about me that I didn’t, like maybe he understood why I was there. That made me feel even more nervous. And I wasn’t scared, just nervous. “I’d be happy to talk with you about your grade, Hillary,” he said. “Would you like to come in?”

I’m not sure why, but something inside me told me not to go in, but if I didn’t go in, I wasn’t going to get what I wanted. “Ah…sure,” I said. Mr. D held the door open and I walked by him and into his house. The house was nice, nothing really fancy, but it was very neat. He led me through the kitchen down a hallway, and into his living room. There was a big, soft-looking gray sofa and a big maroon overstuffed chair and hassock, and a TV and a bunch of other furniture. The room was a whole lot neater than the living room at my house, but my Mom is far from being a neat freak, so… There I was, standing in the middle of Mr. D’s living room, nervous as hell, not sure what to do or say next.

Mr. D followed me and stood there facing me with that weird smile still on his face. “I think I know what you want, Hillary,” he said. “You were hoping you would be able to talk me into giving you a break so you can pass and get your diploma, weren’t you?”

I gulped and nodded. How did he know that?

“I think we can work something out,” he said and all of a sudden I felt a whole lot better.

“Ah…we…we can?” I gulped. “You…you really mean that?”

Mr. D nodded. “I’m sure we can work something out,” he said. His voice was very soft and smooth. It sounded different than it did in school for some reason. “What are you willing to do to get a passing grade?”
His question surprised me. I didn’t expect him to ask me anything like that. I mean, there are all kinds of answers to the question he asked me. “What…what do you mean?” I answered.

“Hillary…” Mr. D took a couple of steps closer to me, so he was standing sort of beside me, a little closer than I would have liked. “…my question isn’t at all difficult,” he continued. “You want me to give you a passing grade. What are you willing to do for me in return?”

I didn’t know what to say because I really didn’t know what he meant. Well, OK, I kind of thought I knew what he meant, like he wanted me to have sex with him or something, or…I don’t know. I started to feel a little scared.
Mr. D sighed. “This isn’t difficult, Hillary. I have something you want; a passing grade,” he said softly. “What you need to do is decide what value you place on what I have.”

“You mean…are you saying I should…” I babbled.

Mr. D smiled and shook his head. “I’m not saying you should do anything,” he responded. “You absolutely do not have to do anything you do not want to do.” He took a breath. “What you offer in exchange for a passing grade is entirely up to you. I will not force you to do anything.” He paused and smiled at me. I think he liked it that I was so confused. Finally, after I didn’t say anything for a while, he said, “Maybe I can help make your decision easier. If you write one paper for me…but I choose the topic…and do a good job, you’ll pass.”

“One…one paper…just one?” I replied. It sounded too good to be true. All he wanted me to do was write one paper? There had to be a catch. “How…how long…um…does the paper have to be?” I figured he’d say it had to be like fifty or sixty pages long or something.

He shrugged his shoulders and said, “That’s up to you. It must be long enough to thoroughly and adequately cover the assigned topic.”

This was sounding better all the time. All I had to do was write one paper on a topic he gave me, and it was up to me how long it was. Heck, if Old Lady Fraley had been this easy to deal with, I wouldn’t have been in summer school at all. “One paper, on a topic you pick, as long as I want?” I asked.

“One paper, on a topic I pick, as long as you feel it needs to be to cover the topic,” Mr. D replied. He must have moved because it sounded as if he was behind me now. That threw me off a little. I was going to turn around but for some reason I didn’t.

“What…what’s the topic?” I asked. I was scared he’d give me something really tough to write about, some weird thing like a history of the romantic novel or something stupid like that.

“You,” Mr. D said.

That totally confused me. “Me?” I said.

“I want you to write a paper on your day, starting with the time you arrived here at my house until you get home,” Mr. D explained.

“From…from when I got here…your house, until…until I get home?” I must have sounded really dense, but I totally didn’t get what he was talking about then. I mean, what was there to tell? My boyfriend was away at some damn football camp and my parents were out of town and there was nothing going on. I was planning on going home and watching TV after I left his house. That sure as heck wouldn’t make for much of a paper.

“Exactly,” Mr. D said softly. “The paper should describe what you do, who you do it with, how you feet while you’re doing it, and what you feel like afterward. An afternoon and evening in the life of Hillary Watkins.”
“But…but I’m not going to…to do anything today,” I stammered. All of a sudden what looked like an easy deal didn’t look so easy.

“Are you sure?” Mr. D asked.

I opened my mouth to tell him that I didn’t have anything planned for the rest of the day when he began running his fingers through my hair. That startled me. I shut my mouth and jumped and I think I gasped, too.

“Your hair is very fine and so soft,” Mr. D said. He kept combing his fingers through my hair. “It always looked that way and I wondered what it would feel like. It feels very nice.”

I could feel my heart start to pound and my chest tightened a little. What was he doing? I knew I shouldn’t be letting him touch me, but all he’d done was touch my hair. What harm was there in that, right? And he did say I didn’t have to do anything I didn’t want to do. I mean, he was a teacher in our school, he was married and he had a daughter. He wasn’t some creep who’d hurt me. And as weird as this probably sounds, having him play with my hair felt good.
Mr. D kept running his fingers through my hair. I was surprised how gentle he was and how really neat it felt. My scalp started to tingle a little. I started thinking it wouldn’t be bad if he never stopped doing that.

“Hillary, does this feel good?” I heard him ask.

“Mm-hmmm,” I replied, nodding.

“Should I stop?”

“You…you don’ t…you don’t have to…ah…stop…if…if you don’t…um…want to,” I stammered.

He kept teasing my hair for a little longer and it kept feeling better and better. I was beginning to hope he’d keep it up all day. Then he stopped. It was weird, I probably shouldn’t have let him touch me in the first place, but he had touched me and I really liked it. And then he stops and I don’t like that. I mean, it was like everything was upside down or something. What happened – and why I let it happen – still doesn’t make sense to me.

I wasn’t sure whether I should say something or not. I almost wanted to, to tell him to keep doing what he was doing. I think I was going to, but before I could say anything, he started tickling my arms. Man, when he started running his fingers up and down my arms, that really made me jump. It was incredible! His touch was so light I could barely feel it, but at the same time it was all I could feel. My insides started to feel kind of jumbled up and fluttery when he was playing with my hair, but now it felt as if a gazillion butterflies were flapping around like mad inside me. I’d stopped feeling scared, though. I really liked the way it felt to have his fingers running up and down my arms. There were goose bumps all over me. When I was little, my grandfather used to tickle me and I always loved that. This was sort of like that, only maybe a million times nicer.

“Your skin is very soft and feels very smooth,” Mr. D commented. “It’s so warm and silky.” His voice was very soft and gentle, just like his touch. I know I should have been scared, but I wasn’t. It was as if he had some kind of control over me, but at the same time he wasn’t doing anything I didn’t like, so…even now, thinking about it, I can’t understand what happened. All I know is it felt really nice to have him tickling me like that. And now that I think about it, I guess I was starting to get turned on a little, even though I didn’t know it then. I mean, a guy was touching me and it was making me feel good, wasn’t it?

I have no idea how long he tickled my arms, or played with my hair for that matter; it felt so good I never wanted it to stop, though. Up and down, slowly, with that wild light touch, his fingers moved over my arms and shoulders. The more he did it, the better it felt and the more I wanted him to do it. I could have moved, but I didn’t – I didn’t want to move, really. He tickled me everywhere on my arms, the outside, the inside, my elbows, the inside of my elbows, my wrists, and my fingers. And even though I wasn’t thinking about doing it, I realized I was moving my arms and hands so he could touch me everywhere he wanted to. I know it probably sounds weird when you read it, but what he was doing to me felt so neat I didn’t want him to ever stop doing it. I was so wrapped up in how he was making me feel, I didn’t really think about what he was going to do next. And actually, if I had known what Mr. D planned to do, I probably would have split. Boy, would that have been a mistake!

Then he stopped tickling my arms, just like he stopped playing with my hair. I’d gotten so into how neat it felt, I really missed the nice feelings when they stopped. I had been standing there with my eyes closed, and when I opened them I realized Mr. D was in front of the big overstuffed chair. He used his foot to plush the hassock that was in front of the chair over in front of me, then he used the tip of one finger to trace the outline of my face. That really felt neat and I closed my eyes again. My grandfather used to do that, too. He only tickled my face for a couple of seconds, though. When it stopped I opened my eyes and Mr. D wasn’t there, or I didn’t think he was until I looked down. He was sitting on the hassock in front of me. “What the heck is he going to do now?” I thought, then I knew.

I jumped and this time I think I moaned a little when he started running his fingers up and down my bare legs. His touch was just as soft as it had been when he was tickling my arms and felt just as good, maybe even a little better. Really great feelings were shooting into my body and I could feel myself getting goose bumps again. And I realized for the first time that my nipples had gotten hard. They were also really sensitive. I was breathing a little harder than I usually do and when I breathed it made them rub against the inside of my bra, I guess, and that felt so wild! I never, ever had that happen to me before.

The more Mr. D touched my legs, the more I realized that I was getting turned on, really turned on! I can’t tell you when what was happening switched from him making me feel good to turning me on, but it did. Boy, did it ever! He hadn’t touched my breasts, or my butt, or anything like that, but I was way more turned on than when my boyfriend Dave touches me those places. I was doing the same thing with my legs that I’d been doing with my arms, moving them so he could touch them all over. And what was even stranger was that he never tried to slide his hands under my dress. He caressed me from my ankles all the way up to my thighs – God, I get all fluttery inside just remembering how neat that felt – then moved his hands back down again. He never even touched the hem of my dress! At that point I wouldn’t have stopped him if he had. Actually, I was starting to hope he would slide his hand under my dress, but he didn’t.

After a while, all of the skin on my legs – and a lot of the rest of my skin, too – was covered in goose bumps and tingling. It was like when he tickled my arms, I didn’t want him to stop, but at the same time I wanted him to do more. I still can’t believe it and I don’t understand how it happened. I mean, Mr. D didn’t force me to do anything, but somehow he got me to let him do stuff I would never have let him do if he’d asked me.
I was standing there, breathing hard, my heart pounding, my eyes closed, while Mr. D kept sliding his fingers over my legs with that awesome light touch he has when, without warning, it stopped. I opened my eyes and saw him standing in front of me, smiling. Then he moved so he was standing behind me again. I had no idea what he planned to do next. Was he going to tickle my hair again? God, I hoped not. I wanted him to go back to touching my legs again, or maybe touching me other places, but…

“Hillary, would you mind unbuttoning your dress?” Mr. D asked. It was the first thing he’d said to me in what seemed like hours and hearing his voice kind of surprised me. What surprised me even more was that, without even thinking about what I was doing, I started unbuttoning the buttons down the front of my dress. Somewhere, deep inside me, I thought, “What the hell are you doing?” but my fingers kept opening the buttons until the dress hung open. I was wearing underwear; a white cotton bra, and bikini panties that actually cover more than some of my swimsuits do, but I don’t normally run around in front of strange men in my undies.

The next thing I knew, I felt his fingers sliding around my neck and he began tugging gently on the dress, as if he was helping me take it off. And I moved my arms to make it easier for him to do it. Do you believe that? I mean, it is so hard to believe, but it really happened.

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