Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: Alana on June 29, 2017, 01:45:00 PM
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The thing you need to know about me is that I'm a man who loves literature. When I'm reading a classic novel, the whole world goes away, and I can't concentrate on anything but the book I'm reading. Which is why it's not a good idea for me to be wearing a dress when I'm reading a classic novel. You have to be careful when wearing a dress.
Maybe you're wondering why a man is talking about wearing dresses. If you are, you haven't read my previous account of my adventures in dresses, posing as a woman in order to work as a substitute teacher.
Originally I was a reluctant crossdresser. But since that time, I haven't been able to get thoughts of dresses and pantyhose and high heels out of my mind. I see my wife in a new dress and I think how pretty it is and how wonderful it would be to wear it. But I've stayed away from my wife's wardrobe because I knew she wouldn't like me trying on her dresses. Not unless I had some excuse.
My wife and I are both substitute teachers. We're trying to get permanent jobs, but teaching jobs are hard to come by these days. Money is tight, and we're not in any position to turn away work. So when a call came in to sub for a sixth-grade teacher for two weeks, it was with regret I had to tell the caller that my wife was already subbing at another school.
"But I'm available," I said.
"No, I'm sorry, this is a girl's school. We only hire female teachers," she said.
So, of course, an idea popped into my head, and I said, "Oh, she's just coming in the door right now. Let me put her on."
I covered the mouthpiece and practiced my female voice. Then I returned to the phone.
"Hello. This is Annie Williams," I said.
"Hello. This is the Vice-Principal at Sapperstein Girl's Academy. I was just telling your husband, we had you in mind for some substitute teaching next week. But he said you were working somewhere else."
"No, I'm free, actually. The teacher I was supposed to sub for changed her plans."
"Wonderful! You'll be substituting for Mrs. Lee for two weeks, starting next Monday. She teaches sixth grade."
"Great! I can be there at 7:30. I take it the lesson plans will be ready for me."
"Yes, everything will be all set. So, we'll expect you then. Do you have any questions?"
"No, no. Well, actually, one question. Is there any dress code?"
"The girls wear uniforms, but I assume you mean for the teachers. The only thing we ask is that you don't wear trousers. Mr. Compson is very strict about that."
"Mr. Compson. He's the principal?"
"Yes, he's the only male member on staff. Don't worry; he's always very professional."
"I was wondering if there would be any objection to me wearing a short skirt."
"No. Most of the teachers are quite a bit older, so short skirts are not too common. And the girls' uniforms have pleated skirts below the knee. You might be wearing the only short skirt in the building. But since this is a girl's school, I don't expect that will be disruptive."
"Good. Well, if you'll excuse me---"
I rang off and went right to our bathroom. I took a shower and shaved all the hair off my body. Then I went to our bedroom and took off all my clothes and underwear and put on my wife's panties. Followed by pantyhose, girdle, longline bra, and slip. I pulled on a pair of her frilly pettipants under the slip. Wearing pettipants is very important. They give you a nice, rounded figure and make it look like you have lovely child-bearing hips. Then I put on one of her dresses and her wig and high heels and checked myself out in the mirror.
I was just putting on make-up when my wife came in.
"What the hell is this?" she said. "Why are you wearing my dress?"
"Well, why was I wearing your dresses the last time I did it?"
"Oh, no. Not this again. Not another substitute teaching job."
"It was your idea."
"Oh, and a great idea it was! It almost got me removed from teaching."
"It wasn't that bad."
"Tell me at least you won't be using my name, this time."
"Honey, how can I use your credentials if I don't use your name?"
"Adam, it's bad enough you keep getting yourself in trouble, but why do you have to get me in trouble right along with you?"
"Annie, it's a girl's school. There won't be any boys to leer at me. What could go wrong?"
"I don't know, but if there's any trouble to get into wearing my dresses, you'll find it. You've been wanting to do this for a long time now, haven't you?"
"It hasn't been that long since I subbed."
"I meant wearing my dresses. I've seen how you look at my dresses. Ever since that one time, you just couldn't wait to try them on again, could you?"
"I haven't been wearing your dresses."
"Maybe not, but you wanted to. What kind of a husband asks his wife how her new dress feels to wear? Or if it feels silky, or if I can feel my skirt brushing against my fingertips as I walk?"
"I am only wearing your dresses to make us some money. Am I wrong in thinking we could use some more money?"
"Alright, fine! Be a woman! Have the operation, for all I care! I don't know why I'm worried. Look at you. You're way too old to look cute in a dress. You're in your fifties. You're really starting to show your age. Your skin is saggy; your face is all pasty and lumpy and doughy. No young boy is going to fall in love with a geriatric old broad like you."
"Annie, that's just mean. Anyway, I told you, it's a girl's school."
"Whatever. When do you start?"
"Monday."
"Then take off my dress! You can wear my dresses on Monday and not before."
"I just wanted to make sure they still fit."
"They fit. Now take off my dress."
"I could really use a weekend in dresses, just to get back in practice."
"Oh, I'll just bet you could! Well, forget it! Take off my dress, right now!"
We spent a tense weekend, with her calling me names like "little Miss Girly Girl" to try to annoy me. Finally Monday morning came, and I chose her shortest, tightest dress to wear to school, a slip-on dress with a black top and a tight white and black houndstooth skirt. I wore dark pantyhose and black high heels.
"Oh, Adam, not that dress!" she said.
"The perfect dress for a geriatric old broad like me."
"You don't have the legs for that skirt, Adam."
"The hell I don't. I don't tell you what dress to wear to school; don't you tell me."
"If you won't dress like a man, can't you at least dress your age?"
"You've worn this dress to work. You're only a year younger than me."
"I look ten years younger. You know, I can still remember our wedding, and the look on your face when you first saw me in my wedding gown. I never realized it was because you wanted to wear it."
I was so mad at her, the first thing I did when I got in my car was take off my wedding ring and put it in my purse.
I arrived at Sapperstein Girl's Academy at 7:30. Some smart alecks like to call it Sappho's Academy, which is very rude and insulting. I must say, even understanding that it was a girl's school, I thought it was a bit much for all the walls to be done up in hot pink. Like being trapped in a bottle of Pepto Bismal.
I was wearing three-inch heels, which might have been a mistake my first day. I knew I'd get used to wearing high heels eventually, but just the walk from my car into the building was enough to give me a cramp.
I bent down to massage my leg when a man I assumed was the principal said, "Annie Williams?"
I looked at him uncertainly, embarrassed that he'd caught me in an awkward position.
"Guilty," I said.
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I shook his hand.
"Jason Compson. The principal. Glad to have you with us."
"Jason Compson? Really? Is that your real name? That's a character from a novel."
"I know. 'The Sound and the Fury.' William Faulkner. Luckily, not a widely read novel. You must be very well read. Have you read a great deal of Faulkner?"
"Only because I had to. I hate Faulkner."
"Oh, I am so glad to hear you say that! Everyone is afraid to say it. I hate him too, and not just because he stole my name. All that free association, stream of consciousness nonsense is so infantile."
"I know! I can't stand an author that's always going all out to try to confuse the reader. It's fake profundity, like throwing a little sand in the reader's eyes to make him think he's in the presence of greatness."
"You know, we should get together and start a William Faulkner non-reading group. We can get together and not read his novels."
"And not discuss them when we're done! I love it!"
At that point I noticed that he wasn't making much eye contact.
"Excuse me," I said. "You keep staring at my skirt. Is my slip showing?"
I held my skirt down playfully.
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"I'm sorry for staring. I didn't mean to make you uncomfortable. It's just that most of the teachers at Sapperstein are much older than you. You are definitely wearing the only mini-skirt in the building. Do you always wear such short skirts?"
"I was told there was no dress code for teachers, as long as I don't wear trousers, and I would never wear trousers. I thought I might as well test that out the first day, by wearing my sexiest dress. Do you like it?"
I posed with hand on hip.
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"Well, it might be a bit of a problem if this were a boy's school. But the girls at Sapperstein are all very well behaved."
"Would you rather be at a boy's school? I understand you're the only man on staff."
"Well, I think the work we do here is very important. I'm proud of what we've been able to accomplish at Sapperstein. But there are times I wish there was a man here I could talk to."
You're talking to one now, Mr. Compson. And you can't seem to take your eyes off his legs in dark pantyhose.
"So, you are Mrs. Williams?" he asked, with the emphasis on the "Mrs."
"I'm divorced," I said.
Now, what made me say that? Just an impulse, I guess. I was already lying about my gender; might as well lie about my marital status as well. In for a penny, in for a pound. And the way things were going with my wife, it might become true before I knew it.
"I see," he said. "I'm a widower, myself."
"Oh. I'm sorry."
"Yes. It was less than a year ago. I'm sorry, I shouldn't bring it up. Still rather painful."
"It must be difficult for you."
"Let's not talk about it."
An awkward moment was ended when the bell rang. He said good-bye and we shook hands, and all the time I just had the feeling that he was devouring me with his eyes.
I headed off for class, but I took one quick look behind me to see if he was still checking me out as I left. He was.
Geriatric old broad, huh?
Jason Compson. "The Sound and the Fury."
Faulkner. Stream-of-consciousness is such bullshit. Anybody can do it.
Walking down the hallway the hallway in my sexy tight dress my sexy tight skirt as it tugs as it tugs tugs tugs my legs in pantyhose oh I'm wearing pantyhose how sweet how delicious to wear pantyhose to wear high heels to wear a delectable slip to be a woman to be feminine to be girly every little breath every little breeze caressing my legs going up my skirt how wonderful to be the pursued not the pursuer to be the prize not the contestant to be the hunted not the hunter to be the hope not the hopeful as Jason Compson caresses me devours me with his eyes with his glance with his hopeful hopeful gaze makes me feel wanted feel needed feel desired
Back that Pulitzer truck to my front door and hand me my Prize now, if you please.
Class started. Everything went smoothly for the most part. The lesson plans were all laid out very professionally. Being as it was a private school, it was a much more ambitious curriculum than I was used to in public school. I introduced myself and took the class through math, geography, history, and it wasn't until we got to English that I got myself in trouble.
As to what came next, I can only tell you it was an accident. Perhaps it was brought on by the fact that I felt very comfortable and very much at home teaching at a girl's school. No rambunctious boys making lecherous remarks about the tight dress I was wearing. So I got a little too comfortable, and I just didn't think about what I was doing.
The class was reading "Great Expectations," my favorite novel, and it was my job to sit in front of class as each successive student read a paragraph, and follow along in the book, pointing out any important details and answering any questions.
Now, I swear I started out the reading with my legs properly and modestly crossed, like a lady.
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I don't even know for sure when I uncrossed my legs. I just got so involved in the novel ( which is quite funny, by the way, read it if you get a chance ), I started to sit with my legs wide open, without even realizing it.
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Then I started to hear a lot of embarrassed titters. The one thing you don't want in a classroom full of girls is a lot of embarrassed titters. I crossly inquired what was so funny.
Jane, the smartest girl in the class, said, "Your underwear is showing, Mrs. Williams."
The girls all laughed, and I looked down, mortified.
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I very sheepishly adjusted my skirt.
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"OK, girls, let's get back to dic-kens."
But it still took a few minutes before they all quieted down.
Imagine what that would've been like at a boy's school! I didn't even want to think about it. But at a boy's school I would've been much more careful and on my guard, so I doubt it would have happened. At Sapperstein there didn't seem to be any lasting ramifications from the slip-up ( if I may call it that ). The girls didn't seem to lose any respect for me.
When I got home, Annie had already started making dinner. I helped her. We stood there in the kitchen in our dresses, working side by side, silently. She was still angry at me for wearing her dress.
When I sat down to eat, she said, "What are you doing?"
"What do you mean?"
"Take off my dress."
"What for?"
"What for! Because you're not a woman, you idiot! You only have to dress like a woman at work."
"Oh, let me wear it a little while longer. What's the harm?"
"It's my dress, and I say you take it off right now!"
"No."
She stood up and yelled, "Take off my dress!"
I stood and reached behind her back and started to unzip the dress she was wearing.
"What are you doing?"
"You said to take off your dress, I'm helping you take it off."
"Stop it!" She reached behind her and zipped herself back up "Do you think that's funny?'
"If you get to have dinner in a dress, so do I."
"Fine! Keep my dress on, little Miss Girly Girl! Wear it in good health! I hope you meet a nice guy in it, and I hope you marry him! I'll be your maid of honor. And I hope I catch the bouquet so I can get married to a real man, instead of a little sissy who wears pantyhose and prances around in my dresses!"
"I don't understand why you have to be so mean."
"Oh, go soak your nylons!"
She left, and slammed the door on the way out. I slept in the guest room that night.
The next day I put on a cute little black and white dress, all covered in stars. It had an adorable Peter Pan collar. I'd been longing to wear that dress ever since I first saw Annie in it, and now I finally had an excuse.
She looked at me and rolled her eyes heavenward, as though there was nothing she could do about it. And there wasn't.
"Thank God we don't have any children," she said. "Think if you had a son. Imagine how ashamed he'd be of you right now, walking around in my dresses, wearing a bra and a girdle and a slip."
"Shall I remind you again that this was your idea, originally?"
"If your father could see you now!"
"Which one?"
"Oh that's right, you have two fathers. That explains so much about you."
"Annie, I don't understand why you're so threatened by all this."
"Oh, right. I'm the one with the problem. You're normal, and I'm a freak because I don't want my husband to wear dresses."
There was nothing to be gained by arguing, so I got out of there.
In the morning, the Principal came up to me in the hallway. It seems he'd been loitering around close to my classroom with that very intention. I wondered if he'd heard about the little incident of the day before. Me showing my frillies.
"Hello, Mrs. Williams. That's a very pretty dress you're wearing. Very nice Peter Pan collar."
"Thank you, Mr. Compson," I said, coyly playing with my skirt a little. I couldn't help it; I was just feeling so girly in my cute little dress.
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"Jason, please."
"Well, then I guess you will have to call me Annie."
"OK. Sure. Annie, it seems I'm in a bit of trouble. My secretary just called in sick, and I have several important letters that have to be out this evening. Now, I did a little research on you and found out that one of the things you teach is shorthand."
"Yes."
That much was true. My wife and I both knew shorthand, and we could probably make much more money doing secretarial work if we weren't born teachers.
"I know it's an imposition, but could you stop by my office today at three o'clock and take some dictation? Then the letters would have to be typed. It might take a few hours."
"Well---not for free."
"No, of course not. I'll make sure you get paid a few hours of overtime."
"Well, it's a bit unconventional. I'm a teacher, not a secretary."
"I would consider it a personal favor."
"Well, when you put it like that, how can I refuse?"
"Great. See you then."
"And I must say, sir---Jason---I haven't run into all that many men who know what a Peter Pan collar is."
"One of the many things you learn when you're the only man working in a building full of women. Excuse me."
He left, and I headed on to class. I thought to myself that the principal probably had his own reasons for wanting to meet with me alone after school, and they probably had more to do with looking at my legs than dictation. He was definitely a leg man, that one. Which was just as well, because I wasn't very well endowed in the other area. My wife was only a B cup, and if I was going to wear her bras I couldn't be more than a B cup, either.
Oh, well. It was just a little innocent flirtation between the principal and me. Just fun. I might as well have some fun during my brief time as a woman.
That day at class it happened again. I can only blame it on the fact that there seemed to be no ramifications from showing my frillies the last time. No complaints, no criticism, no smart-ass comments from any of the girls. So I got careless. Again.
They showed just a little, at first.
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But I was wearing a much looser skirt than the day before, and during a tense passage I pulled the book closer to me, accidentally pulling my skirt and my slip with me. My frillies showed even more.
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Then I heard the laughter and I realized it had happened again. Well, at least I could have a sense of humor about it this time.
"OK, girls, I'm sorry this keeps happening with my skirt. I'll try and be more careful."
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"Why don't you just keep your skirt up, Mrs. Williams? It seems to have a mind of its own," said Jane, the smartest girl in class.
I tugged my skirt down and said, "Now girls, you know this was just an accident. I wouldn't want you to think it was OK to tease a boy by doing something like this."
"In these skirts?" said another girl. True enough. It would take quite an effort to do an upskirt in those long stiff pleated plaid skirts the girls had to wear with their school uniforms.
"Let's get back to dic-kens," I said.
At three o'clock I made my way to the principal's office. I grabbed a steno pad and a pen from the secretary's desk and got ready to take some dictation.
I seated myself comfortably, crossing my legs, and told Mr. Compson---Jason---I was ready to go.
"Good," he said. "And please try to keep your skirt somewhere below your waist while you work."
"Oh, you heard about that, did you?"
I didn't smile, because I didn't know if I was in trouble or not.
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"I did."
"So you brought me in here to tell me off."
"No, I brought you in here to take some dictation. And to ask you to be a little bit more careful in the future."
"I'm sorry. I've never taught at a girl's school before. I just wasn't as careful as I am around boys. You men don't ever have to worry about that sort of thing."
"Mrs. Williams---Annie---you're an excellent teacher. You have a very good reputation. From what I've heard the girls love you, and not just because you show them your underwear."
"Sorry."
"I'm not about to tell you off because of one little mistake. In fact, if things work out, I might be able to offer you a permanent position here. Would you like that?"
A permanent teaching job! At a girls school! A chance to wear dresses to work every day!
"That would be wonderful. And if my skirt happens to fly up over my head today I'm sure you'll be the first to notice and tell me. You haven't stopped looking at my legs since I got here."
"Sorry. Like I said, you're quite a bit younger than most of the teachers here."
"I'm not that young. You must be in your mid-forties?"
"I'm forty-six."
"I'm in my fifties. I'm older than you."
"Really? I can't believe that. You don't have a grey hair on your head."
I better not, or I'm getting a refund on this wig.
"We'd better get to work," I said.
He started dictating one letter after another, and despite what I had said earlier, he still kept looking at my legs. He didn't stare; he would look away now and then, but his gaze kept returning to my legs, as though they were irresistible.
Geriatric old broad, eh?
I was flattered, but it made me nervous. At one point I got so nervous I dropped the pad off my lap. He made a motion to get it for me, but I picked it up and smiled at him.
"Butterfingers," I said.
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"Do I make you nervous?"
"The way you look at me does make me a little bit nervous. But I'm not going to tell a man he can't look at my legs after he's just offered me a permanent job."
"I haven't offered you the job yet. But I won't offer it because you're attractive or because you let me look at your legs. It's because you're a good teacher."
"Do you think I'm attractive?"
"Of course you are. You know how pretty you are."
"Maybe so, but it's nice to hear it now and again. You know, there are some who wouldn't consider this conversation appropriate. I suppose you're going to tell me I shouldn't wear such short skirts if I don't want you to stare at my legs."
"I would never say that. I'm sorry; I never meant to make you feel uncomfortable. Do you want me to look away?"
I sighed.
"You're the boss," I said. "Do as you feel best. Do you want me to lift up my skirt for you? I'm good at that."
"Mrs. Williams---"
"Annie."
"Mrs. Williams, this is all highly unprofessional. I am a principal and you are a substitute teacher. Let's keep things on a professional basis or we could both get in trouble."
"Yes, you're right Mr. Compson. Let's continue."
And I have to give him credit. He didn't look at my legs once more the entire time I was there.
When I finished, I said, "Mr. Compson, it's fine with me if you look at my legs. I shouldn't have objected."
"Please just have them typed for my signature, Mrs. Williams."
I typed up the letters and left them on his desk.
He was a good man. A decent man. I shouldn't have made him feel bad about ogling me. What he said made me appreciate that this was just a little harmless flirting, and nothing to worry about. Just fun.
When I got home, as soon as I got through the doorway, Annie greeted me by whacking me on the head with her purse. She almost knocked my wig off.
"What the hell! What was that for?"
"Take a look at the computer screen, little Miss Girly Girl!"
I went in the study and looked at the computer. There I was on somebody's Facebook page with my legs wide open, showing my frillies. "My teacher, Annie Williams, showing her knickers" read the caption.
"Can't you keep out of trouble for one day?"
"How did you even find this?"
"I set up a Google alert for my name as soon as I saw you in a dress. I knew there'd be trouble; there always is. Congratulations, Adam. Any time somebody Googles me, this will come up. For a job interview, for a loan application, anything."
"Can't I just be a different Annie Williams?"
"Both teachers? Both here in St. Louis? Some of these photos don't even show your face! What the hell were you thinking, Adam? What were you trying to prove?"
"It was an accident."
"Adam, if you can't sit like a lady, stop dressing like one! You have really gone and done it this time! I wouldn't mind it if you just wanted to screw up your own life, but why do you have to screw up mine?"
"This will be OK. I'll fix it."
"I wish someone would fix you. With scissors."
"I'll ask them to take it down."
"Oh, and a bunch of teenage girls are just going to do what you ask?"
"I can ask them to remove your name. They'll do that. The photos will stay up but no way to connect them with you. Honey, this is just a little embarrassment, that's all. It won't really affect your career."
"Bullshit. Teachers are like ministers. Any little hint of scandal and we're looking for a new job. You know how careful teachers have to be, or you would if you were ever careful."
"Annie, don't get hysterical."
"Oh, go soak your nylons!"
The next morning I wore Annie's cute little dress with the violets all over it. Yet another dress with a short skirt. I posed in the mirror and thought, "Resist this, Jason, if you can."
Now what made me think that? Well, his attentions were flattering. Flattery is flattery, in whatever form. And I sure wasn't getting much flattery from my wife, lately.
The principal met me in the hall that morning, as usual.
"Hello, Jason," I said. "Like my new dress?"
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Well, I'd never worn it before. It was new to me.
"Mrs. Williams, I know I said you could wear whatever dress you wanted to work, but maybe it might be time to wear some longer skirts? Just for variety? I think your slip is even showing a little in that dress."
"Oh, I thought you said you weren't going to stare at my legs any more!"
"I wasn't, I just---look, I just came by to ask if you'd stop by after school. More secretarial work."
"For you, anything."
"And maybe a slightly longer skirt tomorrow?"
"Well, I guess you'll have to get your fill of looking at my legs today, then."
A couple of schoolgirls were giggling as they passed us. Jason left without saying a word.
In class, I waited until it was time to read "Great Expectations" again before presenting the case to the students.
"Ladies, it has come to my attention that some embarrassing photos of me are out there on the internet. Now, I don't mind being embarrassed. I can take a joke as well as the next guy---uh---girl. All I ask is that you take my name down, so it's not searchable. This could have consequences to my career if a prospective employer does a search on my name. So please, just take my name off the photos. They can stay up, just remove my name. I think that's a reasonable request."
The girls looked at each other. Finally, Jane, who seemed to be the leader of the whole classroom as well as the smartest girl there, said, "Mrs. Williams, you can't tell us what to do on social media."
"I'm not telling you what to do. I'm just asking, as a personal favor. Come now, I could understand this if you were a bunch of rowdy boys, but we're all women! Women have to stick together!"
Jane rose from her seat as though she were about to make a speech.
"Mrs. Williams, we're not all women. You're a woman. We're girls. You get to wear sexy dresses to work, and we have to wear these dumb uniforms. You have all this freedom to do stuff that we don't get to do. The only real freedom we have is on the internet, and you want us to give that up. It's not fair. We get that someone has to be in charge of us here. We're not---anarchists," she said, savoring the word and its impressiveness. "We get that someone is in charge. But it's just too good to turn down when we get a chance to make the person in charge look ridiculous. And that's you. Don't take it personal. That's just the way it is. Sorry if the most embarrassing thing you ever did is going to live forever, but, you know, welcome to high school."
"But I don't want you to take the photos down, just take my name off them! Isn't there something I can offer you in exchange? Something you want?"
The girls looked at each other.
"You could give us all A's," one said.
"I can't do that. Something that's not unethical."
There was murmuring.
"You could do it again," said Jane.
"You want me to expose myself again? Intentionally?"
"Yes."
I sighed. Annie, I'm doing this for you.
"Very well."
I moved the chair into place.
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"You promise if I humiliate myself for you, you'll take my name off all the photos? And never tell anyone I did this on purpose?"
"Sure," said Jane.
"The rest of you?"
They all murmured that they would, and took out their camera phones.
So I sat down, and did what I had to do. I started with just a glimpse.
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"More! More!" they said. So I opened my legs a little wider, wondering where I ever got the idea that girls are nicer than boys.
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"Now, do that thing where you discover what you've been doing, and you're all shocked and embarrassed."
I'm not a very good actress, but I tried my best.
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"That's it!" I said, standing up and tugging down my skirt. "Now, you keep your promise, all of you."
At three o'clock I went to the principal's office. I got all set up as before.
"Mrs. Williams---"
"Annie. Please call me Annie, Jason. No one's going to think you're unprofessional if you just call me Annie."
"Very well. Annie."
"And as far as I'm concerned, you can look at my legs all you want. Really. I know I said it makes me nervous, but I'm used to it, now."
"Is this because of the job offer?"
"This is because you're a decent guy, and if it makes you happy to look at my legs, what's the harm?"
So he started to dictate a letter. But he kept getting confused, losing his place, fumbling his words.
Finally he said, "I'm sorry. I guess I'm a little distracted."
"No kidding!" I said. "I hardly noticed. I'm starting to realize why you want me to wear a longer skirt."
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"I swear, your skirt seems to be getter shorter while you're sitting there. Maybe we should finish this up tomorrow. When you're wearing a dress with a longer skirt."
"Whatever you say, Jason."
"Tell me, Annie, if you don't like Faulkner, who's your favorite author?"
"dic-kens."
"dic-kens! Oh, dic-kens is my man! I love dic-kens! I really thought a girly girl like you would prefer Jane Austen."
"Girly girl? I'm not that girly, you know."
"Oh come now, Annie! Have you seen you? You are one hundred per cent girly from head to toe. Every inch a lady."
"Oh, there are a few inches that aren't," I said. "Some might say more than a few."
We talked about dic-kens for a while, until I realized it was getting late and I had to be getting on home.
As soon as I got in the door I went right to the computer to take a look at that Facebook page from yesterday. My wife stood behind me with one hand on my shoulder, right on my brastrap. Annie's name was gone. The caption just read, "My teacher accidentally showing her knickers." And new photos were up, the ones from today.
"Congratulations," she said, "every time you put on a dress your entire life seems to be a series of narrowly averted disasters. How did they get those photos from today?"
"That was the price. That was what I had to do for them."
"Wow. You did that for me?"
"We girls have to stick together."
She pulled up a chair and took me by the hand.
"Darling," she said, "don't you think this has gone on long enough? You're getting carried away with this. Look at what's happened already, and it's only been three days. You need to stop wearing dresses. Look at yourself! You look ridiculous! Men don't wear dresses. Men don't wear lipstick."
"And yet here I am wearing a dress and wearing lipstick. So by your own reasoning, I must be a woman."
"Honey, you're really starting to scare me with this stuff. You know you're not really a woman, right? Just because you wear a bra and a girdle and a slip doesn't make you a woman. You know you're really a man. Right?"
"Then why do you keep calling me Miss Girly Girl?"
"Because I'm trying to get you to stop this! Look at those photos! You're making a fool of yourself!"
"Really? Because, you know, Principal Compson was talking about offering me a permanent teaching job at Sapperstein, and I might just take him up on it."
"No! This was only supposed to be for two weeks! What do you intend to do, wear pretty dresses and act girly for the rest of your life? You're not seriously going to spend your entire life in pantyhose, are you?"
"Annie, shouldn't we be more supportive of each other? We're both women."
"We are not! Honey, don't you miss being a man? Isn't your girdle awfully tight? Don't you want to take it off and never put it on again? Aren't your feet killing you from wearing high heels all day? Don't you want to take off that silly dress and go back to wearing pants? They can get another substitute teacher. Wouldn't it be wonderful to go the whole day without once having to worry about your slip showing or getting a run in your nylons? I really envy you, being a man, getting to use the urinal."
"But I'm not a man. I'm a woman. You said it yourself. Men don't wear dresses. Men don't wear lipstick. Obviously I'm a woman. Everyone at Sapperstein Girl's Academy knows I'm a woman. Ask them. You're the only one who thinks I'm a man. If they heard you right now, they'd think you were crazy."
She sighed.
"Yeah. You think you're a woman, and I'm the crazy one."
She let go of my hand and stood up. Then she headed off to the kitchen, pausing at the door to say, "Honey, doesn't that dress fit a little tight in the shoulders?"
"No. It fits me perfectly."
"Really? It always fit me a little tight. Don't you find the skirt rides up if you have to walk too fast? I always have to keep tugging it down."
"Sure, it's a little trouble, but it's worth it to wear a cute little dress like this one. I wish I could wear it again tomorrow." I looked down at the pretty violets covering my bust line, and caressed the material with my fingertips. I loved wearing that dress.
"You know," she said, "I never tried wearing dark nylons with that dress. Maybe I should---oh what am I saying? This is completely crazy! I'm discussing pantyhose with my husband! Get up and give me a hand with dinner, little Miss Girly Girl."
The next day I remembered my promise to wear something longer, so I picked out a nice floral chiffon dress with a handkerchief hem.
It was the wrong day to wear a chiffon dress. The weather had turned unexpectedly warm, and every room had the windows open and electric fans blowing. My skirt kept getting blown about me all day. But it was long enough that it didn't usually reveal anything, expect maybe a little glimpse of my slip, which was nothing scandalous. When it was time to read dic-kens, I insisted that the fan be turned off. So I got through it without showing anyone an upskirt. Finally.
When I went to the principal's office at three o'clock, his office had the window open and a fan on the floor, blowing away. Well, why should he be any different? My full skirt was getting blown around. I tried turning to the side. I was desperately afraid I was going to show him my slip.
"Please turn off the fan," I said.
-
"Why? It's hot out."
"Please. These fans have been blowing my skirt up all day. I'm afraid you're going to see my slip."
I grabbed my skirt, trying to hold it down.
-
"From what I heard, that's not something you mind doing all that much."
But he did turn the fan off.
"It's different with you," I said. "You're a man."
"You noticed."
"Of course I noticed."
And thank heaven you haven't noticed that I'm one, too.
He dictated his letters, and the work was able to go a lot faster with me in a longer skirt.
Afterwards, he asked, "Annie, I have a favor to ask of you, and I can't pay you for it this time. Mrs. Jorgensen and I were supposed to host the Spring Formal, but at the last minute she came down with something. Would you host it with me?"
"What exactly would I be doing?"
"Oh, mostly just keeping an eye on the kids and keeping them out of trouble. And standing by my side looking pretty while I make speeches. You'd have to wear a gown. I'm wearing a tux."
"I don't have a gown."
"You don't?"
"I'm a not a real formal gal."
I meant that my wife was not a real formal gal. She had no interest in going anywhere where she had to wear something sparkly.
"Well, I hate to admit this, but---I still have my late wife's clothes. I haven't gotten rid of them, yet."
"You mean to tell me, you're a man who owns dresses?" I smirked.
"Look, it hasn't been easy. I told you, it was very recent."
"I know, I know. I'm sorry."
"So how about when I go home to change into my tux, I bring back one of my wife's gowns and you can change into it here?"
I winced, picturing some puce-colored taffeta monstrosity two sizes too big for me. But I agreed.
I phoned my wife and told her I wouldn't be home for dinner because I was hosting the Spring Formal. Then I went out and got something to eat. I came back just in time to meet him carrying the gown in a garment bag. He looked very nice in his tuxedo.
"You'll need some help zipping this up," he said.
I smirked.
"Thank you, but I've been zipping up dresses longer than you have."
"You haven't been zipping up gowns. Not this gown, any way. My wife always needed help."
"Thank you, but I'll be fine."
I went into the Ladies Room to change. When I unzipped the garment bag, I couldn't believe the gorgeous glamorous golden gown inside. I lusted after that gown.
I pulled my wife's dress off as quick as I could, and stepped into that knockout of a gown. And damn if he wasn't right! I couldn't reach the zipper to save my life!
I struggled and turned and twisted this way and that. Luckily, a woman came into the Ladies Room and zipped it up for me.
"So, you're my replacement?" she said.
"Am I? Are you Mrs. Jorgensen?"
"That's me."
"I'm sorry to hear you're sick."
"Oh, honey, I'm not sick. I'm just not you."
"You mean he---"
"---wanted to see you in a gown, yes. And wanted you to see him in a tux."
"He does look handsome."
"Yes. He does."
Leaving the Ladies Room, she said, "Annie, he's been so lonely and sad and scared for over a year, now. Be good to him. Don't break his heart."
She left.
I wondered what she meant by that?
I left that Ladies Room. Of course, he was waiting for me.
"Wow," he said. "Just---just wow. You look absolutely beautiful."
-
"More beautiful than your wife?"
I saw the pain evident in his eyes when I said that. I regretted it immediately. I wished I could take the words back.
"I'm sorry---I didn't mean---"
"No," he said. "no, you are not more beautiful than my wife."
He walked away.
The rest of the evening went smoothly. I felt like I was in heaven in that glorious gown. Even boys and girls looking at me and snickering and whispering about "that teacher who lifts her skirt all the time" couldn't dim my happiness. I walked back and forth drinking punch and watching the young kids dance, occasionally casting a guilty glance at the principal. As the evening came to a close my feet started to hurt, and I found a piano bench on which to rest. He approached. I smiled.
-
"Hello, Jason."
"Hello," he said.
"I think there's room for two here," I said, touching the bench.
-
He sat down next to me.
"I'm sorry," I said. "I was just fishing for compliments. That was very insensitive of me to say. Sometimes we women forget that men have feelings. Please forgive me."
"I forgive you. It's just very difficult, seeing you in that gown and thinking of my wife, all the times that we shared, the memories I have of her in that gown. I know you'll say it was my idea that you wear it, and it was. But still, it's difficult."
I put my hand on his and said, "She must've been a wonderful woman."
"You would've liked her. I've been thinking, it's absurd that I should be keeping her clothes. Why don't you keep her gown? You look so wonderful in it, I'm sure she'd want you to have it. In fact, why don't you come to my home after the dance and take all of her dresses?"
I must admit, I had a bit of an erection thinking of all those dresses just waiting for me. I had no idea what they were like, but if they were anything as beautiful as the gown I had on, I couldn't wait to wear them.
"OK. If that's what you want. Could I follow you in my car?"
"Of course."
He got up and walked away. He looked back and said, "Annie?"
"Yes?" I asked uncertainly.
-
"You're not more beautiful than my wife was. But you are AS beautiful."
I know I'm a guy, and I've never been gay or anything, but nevertheless I could just have kissed him at that moment. Maybe I was getting a little carried away.
After the Spring Formal we drove to his house. He opened the door for me and turned on the lights. It was late, and I just wanted to get to his bedroom to look at his wife's dresses.
He turned on the lights in the bedroom, slid the closet door open, and said, "Please take all of them."
So many glamorous, wonderful dresses, I was glad I didn't have to choose.
"You men don't know what it's like to lust after a garment the way we do, do you? Clothes are just warmth to you. Just warmth and nothing else."
I stood in his bedroom carrying an armful of dresses, holding them close to my body, my body in the beautiful golden gown I was still wearing. He stood before, and grasped me by the shoulders.
"Stay," he said.
I backed away from him. This was awkward.
"Look, Jason," I said, "I thought this little thing between us was just a little innocent flirting. I never meant it as anything serious. I'm sorry. I thought you understood that."
He let go of me.
"Oh---right," he said, "right, of course. I didn't mean---that is---I guess I thought---I don't know how I could've thought---"
"I should go. Maybe I should just leave the dresses."
"No, take them. It's silly to keep them. I'm a man. What does a man need with dresses? Take them."
As I headed on out to my car, it seemed to me that I'd been playing with fire and didn't even realize it. But at least things were straightened out between us, now. And I had all of these beautiful dresses to try on!
As soon as I arrived home, my wife said to me, "Where did you get that gown? It's beautiful!"
"Principal Compson gave it to me for the Spring Formal. He's a widower. And look at all these beautiful dresses! They belonged to his late wife, and he gave me all of them!"
She started to look through them.
"Don't worry, I'll let you wear them," I said. "Fair is fair."
"I wouldn't wear them. I don't want anything to do with anything that was obtained by fraud."
"What fraud?"
"What fraud! You are not a woman, try as you might!"
"What has that got to do with anything? You mean to tell me you won't try on this gown?"
"No, I won't."
"I don't believe that for a second."
Much as I hated to take off that gown, I just had to try on some of those dresses, and I didn't have much time before bed. I asked my wife to unzip me.
"No. You wanted to be a woman, you unzip yourself. Be independent."
"How many dresses have I unzipped for you? You haven't gotten out of a dress by yourself since you were single!"
"That's not true."
"OK, fine, that's not true, but if you put it on I bet you can't zip this gown up yourself."
"Yes, I can. Because I'm a woman, unlike you."
"I'll bet you."
"What's the bet?"
"If you can't zip up the gown, you have to tell me that I'm a woman, that I'm pretty, that I have nice legs, and that I have just as much right to wear dresses as you do because I'm just as girly and feminine as you."
"Fine. And if I can zip it up, you call Sapperstein Academy and tell them to get someone else to substitute, and you never wear a dress ever again!"
"Fine."
I wasn't worried. At least I got her to unzip me. She took the gown in the bedroom, and I took all my new dresses into the guest bedroom where I had taken up more or less permanent residence for the duration, and started to try them on.
I loved them all. So tight, so glamorous. I finally settled on a tight silvery black dress to wear to school the next day. It had long sleeves and came with a matching belt.
I could hear my wife grunting and groaning in the next room.
I poked my head into the bedroom and asked, "How are you doing?"
"Fine!" But she hadn't made any more progress than I had when I was putting it on.
"How do you like my new dress? I'm wearing it to school tomorrow."
"Fine! Leave me alone!"
I took off my new dress and everything else, and got ready for bed. Before retiring for the night, I checked in on my wife one last time.
"Give up?"
"Alright, fine, I give up. Zip me up."
"Let's hear it first."
"You freak!"
"Try again."
She sighed.
"You're a woman."
"And?"
"You're pretty. You have nice legs."
"Keep going."
"You have every right to wear dresses. Because you're girly and feminine. As girly and feminine as I am. Is that everything?"
"Yes."
"Adam, you really need help."
"And so do you," I said, zipping up the gown.
"Oh, go soak your nylons!"
"Why did I just know you were going to say that?"
I left her to admire herself.
That night I dreamed about that gown. I dreamed that Mr. Compson and I were alone together in the gymnasium where the dance had been held. We were dancing together, and I was wearing my gown, only it was even more magical than before. It could change color immediately, depending on my mood.
-
What a wonderful dream.
In the morning I found that my wife had at least been able to unzip the gown by herself, since she wasn't wearing it.
I put on my new silvery black dress and headed off to school. I looked for the principal in the hallway but didn't see him anywhere.
I wanted him to see me in my sexy new dress. The only man in the entire building, and he was nowhere to be found. OK, technically not the only man, but certainly the only man who didn't have to wear pantyhose, high heels and a dress to work every day. Where was he?
Then suddenly I saw him rushing down the hall.
He didn't seem to see me, so I got in his way.
"How do you like me in your wife's dress?" I asked.
-
"Excuse me," he said, and hurried past.
I guess he was busy. Well, there'd be plenty of time for flirting later on. His secretary still wasn't back yet, so I knew he'd want me that evening.
And I really needed some flirting at that point in my life, after all the negativity from my wife. Hopefully he realized by now that it was just fun. I needed to feel that there was someone who felt I was a worthwhile person. Even if I was wearing a dress. Maybe especially because I was wearing a dress.
I hoped he didn't think it was insensitive, talking about his wife's dress that way. Well, it was his idea. I hoped he didn't think I was going to take all those beautiful dresses home and just admire them from afar.
It had cooled down, and the electric fans weren't going any more, not that it would've mattered in that tight skirt. In class I was very careful, and got through the day without another unfortunate upskirt incident. I had learned my lesson.
At three o'clock I showed up at the principal's office for more secretarial work. He didn't seem happy to see me, in fact he was very cold and businesslike. We got right down to work.
He was playing "I'm not going to look at her legs" again, so I decided to tease him a little. I held out one leg before me and examined it with care.
-
"You know, Jason, I've been wearing dark nylons all week. I'm not at all sure dark pantyhose are the thing to wear with this dress."
-
I stroked my leg delicately. He glanced in my direction.
-
"Maybe dark nylons are too much. Should I wear tan pantyhose with this dress? Do you remember what your wife wore, when she wore this dress?"
-
He came over and stood before me. I moved my leg out of the way.
"How can you tease me like this," he asked, "when you won't even---"
And then he grabbed me by the arms with his powerful hands and lifted me right up off the chair! Before I could say a word of protest, he pulled me toward him and kissed me right on the lips!
"Stop it!" I managed to say.
"You're the first woman I've had any feelings for since my wife died," he said, and kissed me again.
"Stop it! Stop it! I'll scream!"
He forced me against the wall and put his hand up my skirt.
And then he felt it. It. You know. It.
He pulled his hand back in horror.
"Let me go!" I said.
"You're a man!"
"I know! Let me go!"
He let me go, and I tugged my skirt down.
"What are you doing here? Why the hell are you dressed like a woman?"
"For the work. If you would just hire male teachers---"
"What the hell kind of a pervert are you?"
"Pervert? Pervert? Who kissed who?"
"Shut up! I can't believe I was attracted to you. I'm going to have to warn everyone about you. I have to tell them you're a man."
"Oh, and how are you going to explain how you found out? That could be very embarrassing to you."
"You're obviously not Annie Williams. What's your name?"
"None of your business," I said, and realized I had better get out of there before he grabbed me again. I ran out of the office, pausing only to grab my purse.
I ran to the car. I kept expecting him to chase me, but he stayed in his office. I was out of breath and my heart was racing as I started up my car, but I managed to calm down by the time I got home, though my legs were sweating so much it made my nylons glisten.
Why does this keep happening to me every time I put on a pretty dress?
I don't feel sorry for him. Not after what he did to me. Everything would've been fine if he hadn't lost control that way. I don't feel sorry for any man that would do that to me or to any other woman.
When I got in the house I heard my wife doing something in the bedroom. I went in. She was throwing dresses, slips, shoes and lingerie into a suitcase.
"Are we going somewhere?" I asked.
"I'm going somewhere. You said it yourself. You're a woman. And I'm not a lesbian, so I can't be married to a woman. I'm leaving you."
"No! Please, you can't go! I love you! You're my wife!"
"Whatever you say, Miss Girly Girl."
"Please! I'll do anything!"
"You know exactly what you have to do. Stop wearing dresses. Stop being a woman. Prove to me that you're a man."
"Fine. I'll do it. If that's what you want, I'm no longer a woman."
She stopped packing. She stood closer to me, holding a few silk dresses draped over her arm. One of them tickled my legs. It felt very sexy.
"No more dresses?" she asked. "No more prancing around in a frilly dress and acting all girly?"
"No more."
"No more pantyhose? No more lingerie? No more high heels or make-up?"
"I promise."
"What about all your new dresses?"
"They're all yours."
"Including the gown?"
"Especially the gown."
"What about the job?"
"I'll call and tell them to get another girl."
I stepped closer to her and tried to kiss her.
"Stop it! I told you, I'm not a lesbian!"
"Sorry."
"Say that you're a man."
"I'm a man."
"Oh yeah, you're real manly in your lipstick and pantyhose. Adam, how am I supposed to believe you? If you're a man why do you wear dresses? Look at yourself. After all your promises there you are, still in a dress. You haven't made a single move to slip out of that dress, because basically you don't want to. You love dresses more than you love me. Maybe you really are a woman."
"Annie, I promise---"
"Oh, go soak your nylons!"
I unbuckled my dress. I reached down and grabbed it by the skirt and pulled it off over my head. Then I took off my wig. I stood before my wife in my slip. She laughed.
"What's so funny?"
"You just look so ridiculous dressed like a woman."
Really? Jason didn't think so.
With both hands she slid the straps of my slip down off my shoulders. She tugged it down and it fell to the floor, along with my pettipants. I stepped out of it, and took off my high heels. She went behind me and unhooked my longline bra.
"Now take off that girdle. Take off your pantyhose, and your panties, and go wash off your make-up. When you're done with all that, come back in here and I'll make you glad you're a man. I'll make you forget you were ever a woman."
My wife's libido can turn on a dime, that way.
Well, sometimes I've been known to have a rather fast and loose relationship with the truth, but there are times when telling the truth is the last thing you should do. I would be at home when I was unemployed, and Annie would be at work. And all those yummy dresses would still be there. Waiting for me.
THE END