Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: Alana on June 27, 2017, 03:42:54 PM
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I got in trouble with the Board of Education.
I'm always very nice with my students, because I believe students always need encouragement. Some say I'm too nice. Some think I don't know the difference between being nice, and flirting. I think that's ridiculous, myself. No reasonable person could ever accuse me of flirting with my students.
But there was one sixteen-year-old girl who got the wrong idea. When I mentioned to her that my wife would be out of town for two weeks, she seemed to think it was an invitation to come to my home. She found out where I lived, let herself in the back way, and waited for me on the couch. She waited so long that she dozed off, so that when I got home I didn't realize she was there. I went upstairs and took a bath, and when there was pounding at my door, I answered it in a bathrobe. And there was a lot of yelling and misunderstandings and parental accusations.
So now I'm sweating out their decision, and I'm suspended without pay in the meantime. Money is tight. My wife does some substitute teaching, but it's not bringing in enough cash, and our savings are running out. My wife got a good job substituting for an English teacher for two weeks while she has an operation, but Monday morning when she was supposed to report to the school, my wife was bedridden with a terrible flu virus. She kept trying to get out of bed, but she didn't have the strength.
"I'll call and tell them to get someone else," I said.
"No, Adam, don't! We need the money!"
"You're too sick."
"If only you could go. English is your subject."
"I know. But I'm suspended."
"Hey, that's an idea. Why don't you go in my place?"
"I can't. Besides, they know you're a woman."
"That's what I mean. You can go as a woman."
"What are you talking about?"
"You can fit in one of my dresses. You could even wear my shoes. Come on, they don't know me at that school, and they've never seen you."
"That's crazy! No one will think I'm a woman!"
"You'll pass. You'll be fine. I can help you with your make-up."
"I'm not doing it."
"Adam, wouldn't you love to get back in a classroom?"
"Sure."
"Well, for the moment, the only way you'll get to teach again is in pantyhose. Come on, I'll make you up and let's see how you look. Then you can decide."
So, just as an experiment, I let her dress me up. Soon my legs were shaved, I had make-up on, I was wearing pantyhose and lingerie and high heels and her wig. But it was when I saw which of her dresses she had in mind that I really started to object. It was a short dress with a red tie, a plaid vest and a blue skirt. I would look more like a schoolgirl than a schoolteacher in that dress.
"Come on," she said. "You've come this far."
So I put it on.
"I can't wear this!" I said.
"You're already wearing it. You've seen me go to teaching jobs in that dress. It's the perfect thing to wear. It's sexy. It gets their attention."
"This will never work."
My wife was overcome by a wave of nausea that caused her to collapse back onto the bed.
"Are you OK?" I asked.
"No. But there's nothing you can do for me right now. I just need to rest. Just go. It's too late to call anyone else. Just go."
So I went. But if one person read me as a man, I intended to leave the high school immediately before anyone could even find out my name. I drove to the school and reported in as Mrs. Annie Williams, which is my wife's name. That way, the check would have her name on it, and she could cash it.
Surprisingly, they accepted me as a woman. And when I began to teach the classes, the boys were surprisingly docile, a lot less rowdy than I was used to. I always carried a ruler when I taught, because it made me feel more like a teacher, and as I paced back and forth at the front of the classroom I could feel their eyes on me.
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At one point I could hear some boys in the back saying something, and giggling.
"Would you like to share that with the rest of the class?" I asked.
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"He said you're hot!" said one of the boys, and there was more laughter.
I was embarrassed. I turned beet red. But I quickly recovered my composure. You can't let them see you're rattled or you'll lose control of the classroom.
I put both hands on my hips, and said, "OK, let's diagram that sentence!"
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After school, a skinny young boy with bad acne appeared in the doorway as I was sitting at my desk.
"Mrs. Williams?"
"Yes, what is it, Johnny?" I have a phenomenal memory for the names of my students. After taking attendance once I instantly know all their names.
"I'm sorry for the disturbance."
"Why? Oh, are you the boy who said that thing about me?'
"I said you're hot."
"You shouldn't talk like that about your teacher. It's disrespectful."
"I'm sorry. Is there any way I can make it up to you? Anything I can do for you?"
I smiled. This kid wasn't likely to have a girlfriend for a long, long time, and I didn't want to take away what little self-confidence he had.
"No thanks," I said. "Not just now. Maybe later."
"OK," he said, and left.
When I got home I discovered that my wife felt better. I told her she could take over for me tomorrow.
"No I can't. Didn't you check in using my name?"
"Yeah. So?"
"Won't it look strange if one Annie Williams is gone and another one shows up tomorrow? You'll have to do the whole two weeks."
"Two weeks! I don't want to wear dresses for two weeks!"
"Oh, boo hoo. I have to wear a dress to work every day, and I got used to it. You will, too."
"That's what I'm afraid of."
"Sorry, dear. You're stuck."
I sighed.
"Alright, get me out of this dress. At least I can wear men's clothes at home."
The next day, Annie picked out a tight white dress for me to wear. When I got it on I realized how difficult it was to walk in that thing. I complained that it was as tight as a sausage casing, and she told me all over again that it was better to wear something sexy.
So off I went to school again. After only my second day in high heels my feet were already starting to hurt, and as I reached the top of the stairs I developed a cramp in my leg. I reached down to massage the cramp.
"Are you OK, Mrs. Williams?"
I looked up and smiled. It was Johnny.
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"Charley horse," I said.
"That's too bad. Would you like me to massage your leg a little bit?"
I looked around. There weren't too many people in the hallway, and those that were there didn't seem to be paying any attention to us.
Students should never be discouraged from doing something nice.
"Sure," I said. He got down on one knee, and I said, "Don't you be looking up my skirt, you naughty boy!"
He massaged my leg, and it felt much better. He seemed a bit nervous, for some reason.
"That's fine," I said.
He stood up. I thanked him and said I had to get to class. I was late, and I walked as fast as I could, my tight skirt stretched to the limit.
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Once again, at class it was amazing how docile the boys were. But it still felt creepy, their eyes on me every second, watching my every move. I reminded the class that there was a test scheduled for tomorrow.
I kept my ruler in my hand almost the whole day, and after class I dropped it and it slid under the desk. I tried to retrieve it. It wasn't easy to bend down in that tight dress. I couldn't reach it, and I didn't want to get down on my knees, wearing pantyhose. I got a little stool and sat down, and tried to reach under the desk.
"Hello, Mrs. Williams!" It was Johnny, as usual. I smiled.
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"Hello, Johnny. Could you help me? I dropped my ruler."
Immediately he was down on his knees, retrieving my ruler.
He handed it to me, and I said, "Thank you so much, Johnny. This darn dress is so tight, I couldn't reach under the desk."
"Why did you wear that dress, if you don't like it?"
"Well, it's a long story. My spouse insisted I wear it."
"You shouldn't let your husband tell you what to do."
"Johnny, you're getting a little too personal. I'll tell you what, there's something else you could help me with. I've got a list of school supplies I need to get. Where is that list? Oh, here we go. Oops, butterfingers!" I said, as I dropped the list.
I was tired of being helpless, so I squatted down and picked up the list before Johnny could get it for me. Man, was there anything that wasn't difficult to do in that tight dress?
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"Here we go. I need to go to the supply closet. You can help me carry some things. OK?"
"Sure!" he said, enthusiastically.
On the way back from the supply closet, he insisted on carrying everything. He wouldn't let me carry a thing.
"I wish all high school boys could be as nice and gentlemanly as you," I said. He just smiled.
I was still having some trouble climbing the stairs in that dress, and as I reached the top step, one of my high heels came right off my foot. Johnny tried to pick it up, but his arms were full of school supplies.
"That's OK! I got it!" I said. "Just because I wear a dress, I'm not completely helpless, you know."
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When I got my shoe back on, Johnny kept looking at me like there was something wrong. I asked him what it was.
"Your skirt is all wrinkled," he said.
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"Oh. Thank you, Johnny. I didn't even notice that. I'm just not used to wearing dresses this tight. This dress is going to be up around my neck before you know it."
After I straightened my skirt, we made our way back to the classroom, and he helped me put the school supplies away.
"Is there anything else I could do for you?" he asked.
"Yes. Get an A on the test tomorrow," I said, and winked.
"Yes, Ma'am!" he said, and ran out the door. Now, if that boy wasn't going home to study all evening, then I'm no teacher.
The next morning I laid down the law to my wife. No more tight dresses. I chose a pretty purple floral dress with a loose, flowing skirt.
As always, Johnny was there first thing in the morning to see me in the hallway.
"Hello, Mrs. Williams. That's a beautiful dress you're wearing. It's really pretty!"
"Why thank you, Johnny. You are so sweet! I wish my spouse were as nice as you!"
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"He's crazy if he doesn't think you look beautiful in that pretty dress."
"Well, I took your advice, and I made up my mind I wouldn't allow him to make me wear a tight dress every day if I didn't want to. This one is nice and comfortable."
I turned to go to class. Some idiot had left a wastepaper basket out in the hallway. I almost walked right into it. I tried to sidestep, and I lost my balance in my high heels, and fell right on the floor.
I was mad. It's embarrassing to do something like that in front of a student. But I was mindful of the fact that I was supposed to be a woman, and I thought the ladylike thing to do would be to laugh the whole thing off.
I smiled up at Johnny, and said, "Oh well, at least I didn't lose my high heels. Help me up, would you, please?"
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Johnny helped me up, and as I got to my feet I kind of fell forward onto him for a second. Our bodies touched, and I put my hand on his shoulder to steady myself.
"Thank you, Johnny," I said. He excused himself, and left. He seemed nervous.
At class, it seemed as though the boys were a bit more rowdy. They didn't stare at me quite as much as before, in my loose fitting dress. But I didn't care. It was worth it, as long as I didn't have to put up with their creepy stares. Anyway, I had a test to administer.
After class Johnny dropped by, but I had a lot of tests to grade and I told him I couldn't talk to him.
"I could help you grade your tests."
"Oh, that is so sweet of you, Johnny! You are so helpful! But I'm afraid this is something I have to do by myself. But it's wonderful of you to be so thoughtful."
The next day I picked out a maroon dress with a fairly long, full skirt, that wouldn't look out of place in "Little House on the Prairie." I should've had a bonnet to go with it.
Every morning Johnny seemed to make it his business to pass me in the hallway on the way to class. It didn't matter if I was early or late, he was always there, and this morning was no exception.
"That is such a pretty dress you're wearing, Mrs. Williams. You just look beautiful!"
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"Oh thank you, Johnny! Why can't my husband say nice things like that to me? Maybe I should get rid of Mr. Williams, and you can be my husband!"
"OK!"
Students can never get too much encouragement from their teachers. Forming a close relationship with a teacher can only increase a student's desire to succeed academically.
I asked Johnny to see me at the end of the day, because I had a little surprise for him.
The boys in my class were being rowdy, again. It wasn't easy to get them to settle down.
"Class? Let's begin," I said, standing up front, holding my ever-present ruler.
No one paid any attention to me. I stood with my hands on my hips, trying to look a little sexy and coquettish, just to get their attention. But no one would ever think I’d look sexy in a dress like that.
"Class? Can we get started?"
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Finally I just slapped the ruler against the desk until they quieted down. Another good reason to carry a ruler.
Classes for the day went fine after that. At the end of the day, Johnny dropped by, as I'd asked him to.
"I've got something for you," I said, holding his test behind my back.
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"What is it?"
"You got an A!" I said, revealing his test.
"I got an A!" he said. Then he put his arms around me and hugged me. I hugged back. These are the kind of moments teachers live for. Students need not only encouragement, they need to be rewarded for doing well.
Friday I wore one of my wife's frilly floral dresses. Some of her sexier dresses were hanging in the closet not too far away, and I thought about wearing one if it would placate some of my rowdier students, but spending another day in a too-tight dress, my skirt stretched to the limit with every step I took, just didn't appeal to me.
As I put on the dress, I couldn't help thinking that Johnny would love it. I was right.
"Wow! That is such a beautiful dress you're wearing, Mrs. Williams. You just look incredible!"
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"Oh, thank you, Johnny! You just make me blush every morning! But I love it!"
Politeness in a student should never go unappreciated.
"Mrs. Williams, I look forward to seeing you every morning, but I kind of dread it too, because I know once I see you I won't see you again until class starts in the afternoon. Isn't that strange?"
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I couldn't resist seizing the opportunity for a brief lesson in literature. A teacher never ceases being a teacher, after all.
"Oh, it's not so strange, Johnny. Marcel Proust wrote about being a child and waiting for his mother to come kiss him good night. I remember, he wrote, 'My sole consolation when I went upstairs for the night was that Mama would come in and kiss me after I was in bed. But this good night lasted for so short a time, she went down again so soon, that the moment in which I heard her climb the stairs, and then caught the sound of her garden dress of blue muslin, from which hung little tassels of plaited straw, rustling along the double-doored corridor, was for me a moment of the utmost pain; for it heralded the moment which was bound to follow it, when she would have left me and gone downstairs again. So much so that I reached the point of hoping that this good night which I loved so much would come as late as possible, so as to prolong the time of respite during which Mama would not yet have appeared. Sometimes when, after kissing me---'"
My monologue was interrupted by a couple of young boys fighting. What the fight was about I never discovered. I told them to break it up, and I stepped in to try to pull them apart. One of them was shoved into me, and I found myself flat on the ground for my trouble. The boy tried to stop me from falling by grabbing at my skirt, but my skirt slipped right out of his hands, and a good thing too, or he might've ripped my dress right up the middle. Another of the male teachers broke up the fight as Johnny came running over to see if I was alright.
I smiled up at him.
"Well, here I am again! This is getting to be a habit with us. At least I didn't trip over my own feet like a klutz this time. Help me up, Johnny."
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Johnny helped me to my feet as the school bell rang.
"Oh, there's the bell," I said. "You always make me late for class, you naughty boy!"
After class Johnny dropped by, as usual, wanting to know if he could help with anything. There was nothing I needed, but we had a nice conversation anyway. I asked him about his classes. He asked me about my husband, and I had to make up some things to tell him. I hated to lie to him, but this whole stupid charade wasn't my idea. Another week and it would be over. No more going to work every day wearing nylons.
As he got up to leave, he showed me a book he'd check out from the library, and I couldn't believe it. "Swann's Way" by Marcel Proust!
"It's not easy to read," he said, "but you made it sound so good."
I couldn't help myself. I hugged him again. If wearing dresses and high heels and lipstick could get a young boy interested in literature, it was worth it.
"Have a great weekend," I whispered into his ear.
I had a great weekend, getting to wear pants and be a man again, for two days. But Monday always comes around eventually, and once again I faced a closet full of dresses, standing there in a slip and wondering which pretty dress to wear, looking for one that wasn't too sexy. I finally settled on one that buttoned up the front, which was handy. No zippers to mess with.
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I usually sneaked out of the house before my wife could see me. She nagged me quite enough about what to wear back when I dressed like a man, but my own wife nagging me about which of her dresses I should wear was more than I could take. She kept complaining that I wouldn't take her advice. "I've been a woman longer than you have," she said.
School went by pretty fast. I had the usual encounters with Johnny, both in the morning and at class and at the end of the day. He dropped by, and we discussed Marcel Proust.
Driving home, I passed a dress shop that had a very sexy blue beaded dress in the window. I thought I might like to get that for my wife, but I'd be too embarrassed to buy it. Then, of course, I thought, what in the world should I be embarrassed about? I'm a woman, now! For the moment, at least. So I parked and got out to have a look at that dress.
I asked the saleslady if I could try on the blue dress in the window. She got it for me, and I slipped it on and checked myself out in the mirror. I looked pretty good in it, so I could be reasonably sure my wife would look good in it.
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Then I took a look at the price, which I should've done before I tried it on. There was no way I could afford this dress. Too bad. I went back into the changing room.
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Staring at myself in that beautiful blue beaded dress, it occurred to me that the dress I'd originally worn buttoned in the front, and if I put it on over the blue dress, I wondered if anyone could tell I was wearing two dresses. I put on my other dress and buttoned it up. Looking at myself in the mirror, I didn't think anyone could tell. A week or so ago I didn't even know what it was like to wear one dress, and now I had on two.
It looked to me like I could leave the shop this way and no one would know the difference until I was long gone. There was no electronic security system that I could see. I could tell them I left the blue dress in the changing room. My wife would really love this dress.
Well, here's an ethical dilemma. I've always wondered, are people honest out of high-minded, noble, abstract principles, or are they just afraid of getting caught? I've never been bothered by any dregs of conscience. I'm an English teacher, not a Sunday school teacher. If I got caught, it would affect my career as a teacher, but Annie Williams, the Annie Williams staring at me in the mirror wearing two dresses, was due to disappear in a week's time. If I could just get out on bail, I could take off my dress and never be seen or heard from again.
But of course, it wasn't that simple. I had my wife's ID in my purse. They would call her. And though I have no high-minded or noble principles, my wife is loaded with them. She's not above the occasional lie, but she could never be a part of shoplisfting. In fact, even if I didn't get caught, I could quite easily imagine her refusing to wear a stolen dress. Unless I neglected to mention that it was stolen. But I could also imagine her being upset that I spent so much money on one dress, and returning it.
While I was standing there, pondering what to do like Hamlet in high heels, the saleslady knocked on the door and wanted to know if I was OK. I said I was fine, and started taking off the dress I was wearing. Both of them.
I felt some regret as I returned it to its hanger. I wondered if this wasn't just an excuse to try on that blue dress. Maybe I was becoming addicted to wearing dresses and being a woman. Good thing this would be over in a week.
Tuesday I picked a white lace dress that I didn't think would be too sexy. Unfortunately, on the way to school I realized that it was a very itchy dress. But worse than that, in the hallway I realized I was wearing the wrong slip. My slip was showing. Not much, but enough.
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"Hello, Mrs. Williams," said Johnny, startling me.
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"Hello, Johnny! You scared me."
"Are you OK, Mrs. Williams? What's wrong?"
"Nothing's wrong!"
"Is it that your slip is showing?"
"Oh, no! You can see it? Is it noticeable?"
"I'm sure no one will notice it."
"You noticed it! What if I just stand like this, with my shoulders held back?"
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"You can still kind of see it, a little."
"Great. Just great. Well, don't tell anyone, Johnny. I'll just have to hope that no one says anything."
But they did. They didn't notice it at the beginning of class, but before long one of the boys or one of the catty girls made some comment, and everyone would laugh. It got so I would start each class by saying, "Listen, I know my slip is showing. I'm sorry about that, but let's try not to dwell on it, OK?" But that would just start the remarks a lot sooner.
I know I should've been unflappable. But I just wasn't used to this kind of thing. The idea of walking around all day with your underwear showing and being unable to do anything about it is not the sort of thing men ever have to deal with. During the class with Johnny in it, I had to explain at one point what a Freudian slip was, and a smartass said, "Is that the kind you're wearing?" More laughter.
"That's enough of that!" I said.
"Leave her alone!" said Johnny. "She just made one little mistake, is all. Quit making fun of her!"
"Pet! Pet! Pet!" said a few boys.
"Stop it!" I said. The class bell ended my humiliation.
My slip didn't show when I sat down, so when Johnny came by at the end of the day, I was sitting in a chair with my legs crossed.
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"Hello, Mrs. Williams."
"Hello, teacher's pet," I said.
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"Are you OK?"
"I don't know. It's silly, I guess. You do one thing wrong and they make fun of you all day."
"Welcome to high school," he said. "At lunch, some of the guys said you were letting your slip show on purpose just to tease us, but I said you would never do that."
"Thank you for standing up for me. You know what I wanted to say today, in class?"
"What?"
I stood up.
"That I could do a lot worse than have a teacher's pet like you. A wonderful, sweet, nice boy who always thinks about others before himself. Some girl is going to be very lucky to have you as a boyfriend."
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Never let an opportunity pass by to give a student that little extra burst of confidence.
"Thank you."
I put my arms around him again, in a hug of gratitude. As my lace-covered body came in contact with his, I said, "There's a particular teacher who's wearing a lacy white dress, with her slip showing, who thinks you're pretty special."
The next day I picked out a red Asian-style dress. When I showed myself to Johnny, he was quite taken aback.
"How do you like my dress?" I asked him. His eyes went up and down my body, but he didn't speak.
"Wow," he said.
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Could this dress be sexy? It wasn't very tight, or very short, or low-cut. Was I in for another day of creepy stares from teenage boys?
I got my answer when class began. I tried to start class, and one of the boys actually whistled at me. I did my best to ignore it.
Johnny came after class, and we discussed Proust again. He was too much of a gentleman to make me feel uncomfortable by staring at me too much.
Then, as I was going home, driving through the parking lot, I saw him walking towards the street. I stopped the car and got out.
"Did you miss the last bus?"
"Yes. I guess we talked too long."
"Get in. I'll give you a lift home. I'm not having you walk home because of me."
"That's OK, Mrs. Williams. You don't have to do that."
"Not another word. Get in the car at once, you naughty boy!"
I turned and got in my car, confident he would do what his teacher asked.
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He gave me directions, and as we pulled up outside his house, I suddenly had a need to relieve myself. I asked if I could use his bathroom.
"I suppose so," he said.
He let me into the house and told me where the downstairs bathroom was. When I came out, he was waiting for me in the living room.
"This is such a lovely home you live in," I said.
"Thank you. You know what else is lovely? You're lovely."
"Oh, Johnny, that is so sweet of you to say! You are just the most kind, thoughtful boy in the entire school!"
"Thank you."
"Would you mind if I just sat down for awhile before I drive home?"
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"I would love it."
I sat on a chair and said, "My feet are so tired. When you have to wear high heels all day, your feet tend to hurt. Be glad you're not a woman, Johnny."
"I am. But I'm glad that you're a woman."
"That's sweet. You know, I would just love it if someone gave me a foot massage. Hint hint!"
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"You'd like a foot massage?"
"You remember before when you massaged my leg? That felt so good. Massage my feet a little, Johnny."
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He began to massage my feet, and I said, "Johnny, that feels so good!"
And all of a sudden, with no warning, he pounced on me and tried to kiss me! He was all over me! I kept trying to push him away. What have I ever said or done to make him think I was interested in him that way?
"Johnny, what are you doing?"
And just to make everything complete, the next thing I saw was his mother walking in the door! I didn't even hear her driving in! Damn Hybrid cars.
"What are you doing to my son?" she yelled. Well, I was fighting him off, was what I was doing. She demanded to know who I was.
"This is Mrs. Williams, my teacher," said Johnny. "We're in love!"
"Get away from her, Johnny!"
"I can explain!" I said when I got up and smoothed my skirt.
"Explain to the school board! Get out! Get out of my house!"
So when I got home, I called the school and told them that maybe it was a good idea for someone else to finish up the week. Then I took off the red dress and told my wife that she should wear the dresses in the family from now on. She wasn't too pleased when I told her what had happened.
There was a happy ending to all of this. Johnny's mother tried to make a stink, but it never went anywhere. My wife was summoned to the informal hearing, but when both Johnny and his mother were unable to recognize her as the woman who was supposedly molesting Johnny, they had to drop the charges. My wife did a good job of pretending she had no idea what it was all about.
But if I could've spoken a word in my own defense, I would've said that a teacher needs to be able to inspire his students however he can, and asking a teacher not to care too much about his students or to refrain from developing a personal relationship with them is like asking parents not to love their children too much, for fear that it might lead to something inappropriate. More good than harm can ever come from a teacher hugging a student, and constantly looking over a teacher's shoulder for signs of inappropriate behavior just makes it that much harder for him to do his job.
The original charge that had resulted in my suspension was finally ruled a misunderstanding, and I got to teach again. But I had to attend some classes on the proper boundaries between student and teacher.
Which I really don't think I need. Do I?
THE END
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