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Dressed For Brother's Teacher - Part 1
🕑 Added 2025-01-16 13:32:12 +0000 UTCALL STORY LIST | PARTS - PART 2 | PART 3 | FINAL CHAPTER
Written By - Jenifer White
"No!"
"Please, Dana! You looked just like her!"
"I did not, either! It's a dumb idea, and you'll get us both in trouble."
Last year, for Halloween, I dressed up as my mother. I wore one of her dresses, and she put makeup on me, and everybody said I looked like her. But now, here was my brother George holding a notice from the school saying his teacher wanted to talk with my mother, and you can guess what kind of a stupid idea he had in mind.
"If she finds out I'm flunking Sixth, I'm dead!"
"She's going to find out eventually. How does me wearing pantyhose and a dress keep you from flunking?"
"I swear I'll work harder if you'll just do this one thing for me!"
"He is never in a million years going to believe I'm Mom."
"Yes, he will! He's never met Mom!"
"He'll never believe I'm a woman."
"Yes, he will! Dana, if you do this, I'll give you all my paper route money."
"All of it? But that's gotta be at least---"
"Two hundred and twelve dollars and thirty-six cents."
"You'll give me two hundred dollars just for wearing a dress?"
"Yes!"
I sighed.
"All right, fine! I've got this stupid girl's name; I guess I might as well wear a dress. But you have to promise to give me the money, even if he finds out and we get in trouble."
"I promise! I swear!"
"But how are we going to get there?" I'm 16 years old, old enough to drive, but my mom takes the car every night. She's a swing-shift nurse, and she leaves us alone every evening except the weekend.
"We'll have to walk."
"Somebody will see me!"
"It'll be dark by eight. If anyone sees you, they'll just think you're Mom. You'll be wearing her dress."
"This is crazy. It's never going to work."
"It'll work. You look really pretty in a dress."
"Shut up! I do not!"
I called Mr. Johnson and set up an appointment for the following night, trying my best to sound like my mom. Then I undressed and got in the shower and shaved off what little body hair I had.
The next night, the time came to put this stupid plan in motion. Mom left us dinner for us to reheat, said goodbye to us, and was gone until after midnight. It was time for me to put on one of my mother's dresses.
I got all dressed up and put on one of my mom's wigs and some make-up, remembering as best I could how my mom had made up my face for Halloween. I came out of Mom's bedroom wearing one of her pretty floral dresses with lace about the bodice, and as soon as George saw me, he started laughing like crazy.
"Shut up! That does it. I'm getting out of this stupid dress!"
"No, no, I'm sorry! You look great! Really!"
We walked to school, and no one saw us, or if they did, they didn't think anything of it. We live at the end of the block, and it's fairly secluded. The neighbors can't see very well what's going on at our house unless they make a real effort.
My feet were killing me by the time we got to school, and it was only three blocks. We went to the classroom, and there was Mr. Johnson. I was so glad I'd never had him for sixth grade. I introduced myself as Mrs. Peterson, and he believed me! He asked me if Mr. Peterson could come, and I said I was a widow.
I sat down, remembering all the things I'd learned last Halloween about sitting down properly, tucking my skirt beneath me, and crossing my legs the way a woman crosses her legs.
"I'm afraid your son George is flunking. If he doesn't work harder, he's going to have to repeat the sixth grade."
"Yes, that's what I thought this was about. Would you know of a tutor who could help?"
He gave me some names, and I promised that George would work harder. We talked about some of the areas where George needed improvement, and I pretended to pay attention. I stood up to go, and he shook my hand.
"George," he said, "would you give your mother and me some privacy?"
George said yes, and he waited outside.
"Mrs. Peterson," he said, "may I call you Caitlin?"
"Certainly. Could you let go of my hand?"
"Oh, sure. Caitlin, that's a lovely dress you're wearing."
"Thank you."
"Nowadays you seldom see women willing to wear pretty, feminine dresses."
"Well, most of my mom's dresses are like this. I mean, of course, that my mom, who would be George's grandma, wore dresses like this, and so do I, because like mother, like daughter. That's what I mean. I just meant that we both like to wear pretty dresses because we're both women and all. Sorry, I'm babbling. I'm a little nervous."
"That's alright. Caitlin, I wonder if you have a boyfriend.
"What? No! Why would you ask me that?"
"Well, I think it's obvious that you're attracted to me."
It was hard to come up with a response to that. Open-mouthed in shock and surprise, I just shook my head no.
"Can you think of any reason why we shouldn't go out together? On a date?"
"What! No, I---"
"Then it's a date."
"No, it isn't. I can't go out with you."
"Why not?"
"I just can't, is all."
"Caitlin, if you go out with me, I can pretty well promise you that George will not flunk the sixth grade."
"What! That's unethical! That's just wrong! You can't promise a thing like that."
"That's exactly what I'm promising."
"Mr. Johnson, I'm going to leave right now, and I'm going to forget this entire conversation, and I advise you to do the same!"
I spun away from him, and my full skirt spun with me.
George was waiting outside in the hallway.
"What are you doing?!" he said.
"We're going."
"We are not! You're going to go in there and tell him you're going out with him!"
"You heard that?"
"Yes, I heard! This could get me through the sixth grade!"
"I may be wearing a dress and pantyhose, but I'm not going to date some man!"
"Yes, you are! If you don't, you don't get the money! And I'm going to run home and lock all the doors and lock you out, and you can explain to Mom what you're doing in her dress!"
"You wouldn't dare!"
"Everything OK?" asked Mr. Johnson from behind us, scaring the hell out of me.
"Everything's fine," I said.
"I had a feeling your son might be eavesdropping. So, have you given any thought to what I said?"
I sighed. "Fine. Pick me up tomorrow night at seven."
"I thought you might change your mind."
I was so mad at George that I walked home as fast as I could in high heels and didn't say a word to him. I didn't run home, though I wanted to, but when we got in the door, I was in such a hurry to get out of that stupid dress that I ran to the stairs. I wasn't used to wearing high heels. I fell right on the floor, and my brother would not stop laughing.
"Hey Mommy, your slip is showing," he said.
"Shut up! Don't laugh at me! I'm doing this for you."
"And two hundred dollars."
I got up. "Stupid dress! Stupid pantyhose! Stupid high heels!" I said.
I went upstairs and into my mom's bedroom. I flipped on the light and looked at myself in the mirror, wearing my mother's dress. I started wriggling out of the dress.
What kind of a mess was I getting myself into here? And how long would it go on? Would Mr. Johnson be satisfied with one date? He doesn't take no for an answer. Wearing dresses was bad enough, but dating a man? How could I get out of this? If I just told him I'm a boy, he'd tell my mother, and I'd be in big trouble. I could threaten to tell them about his unethical promises, but he could deny them. What could I do? I was trapped. Trapped in a dress.
So the next night, there I was in front of Mom's closet again, picking out a dress for my "date" with Mr. Johnson. George wanted me to wear something tight and sexy. He pointed out a sexy gold dress.
"Wear this."
"Mom would never wear a dress like that on a first date."
"Come on. Just try it on. You have to look sexy for your boyfriend."
"Shut up."
"You have to keep him happy, or he'll never pass me. Just try it on."
I tried it on. I guessed it would do as well as any other.
When Mr. Johnson arrived, almost the first thing he said was, "Is that the dress you're wearing?"
"Well, being as I've got it on, I guess that would be a clue that I intend to wear it tonight. Something wrong?"
"It's a little too fancy for the place we're going. And anyway, it's not how I pictured you."
"What do you mean?"
"Well, one of the things that attracted me to you was your femininity."
I could see George out of the corner of my eye, trying not to laugh.
"You never see women wearing colorful, twirly, feminine dresses like the one I saw you in last night. You were born to wear pretty, feminine dresses."
"Yeah, that's right, Mom. You were BORN to wear pretty, feminine dresses."
"Shut up. I mean, be quiet, Georgie." He hates being called Georgie, but that's what Mom calls him.
"Tell me the truth, Caitlin. Are most of your dresses like the one you're wearing now?"
"No."
"I just want you to be yourself, Caitlin."
I really doubted that was true.
"You do realize that you're asking me to take off a tight, sexy dress and change into a looser, more comfortable dress with a longer skirt?"
"Yeah, I guess I am."
"OK, if that's what you want."
I went upstairs and into Mom's bedroom to change. George wanted to follow me, but I told him I could handle it by myself, thank you.
I had to admit, Mr. Johnson was right. Most of Mom's dresses were pretty, feminine, twirly, floral dresses, and she did look a lot better in them. I changed into a light-colored floral dress. It took me a while because I had to change my pantyhose, too. I hadn't been a woman for very long, but I knew that women don't wear dark pantyhose with a light-colored dress.
I came out in Mom's floral dress.
"What do you think? Is it twirly enough for you?" Just to tease, I did a little twirl for him.
"Beautiful. I really like you in a floral dress."
"Thank you," I said.
As we were leaving, he said, "Excuse me, but you're not leaving George here all by himself, are you?"
"Oh, no," I said. "Dana is here in the house somewhere."
"Ah. Well, I'm sure your daughter will have no trouble."
George laughed a little.
"No, no, Dana is my son. He's probably in his bedroom. He keeps to himself."
"Yeah," said George, "Dana has some weird habits. You know something, Mom? I bet he's probably started wearing your dresses again."
I was embarrassed. I looked from George to Mr. Johnson and back to George again.
"I'm sure he isn't," was all I could say.
"I bet he is. He's probably started wearing your nylons, too. And your bra. I bet he's even been wearing your slip."
Self-consciously, I looked down at the slip I was wearing, clearly visible through my sheer dress. I think I was blushing.
Mr. Johnson said, "Would you like me to have a talk with him, Caitlin? He might need a man to talk to about this."
"Yeah, Mom, because you're a woman. You like wearing dresses; you don't know anything about what it's like to be a normal boy."
"I do so! I mean, I'll deal with this when I get back! Let's go, Mr. Johnson."
"Mark."
"Let's go, Mark."
Before we left, I saw George take out a digital camera.
"Smile!" he said. And before I could object, he'd taken a picture of the two of us.
"Give me that!" I said.
"Caitlin, we really should be going now."
Mark pulled me out of the room, but I intended to get that photo from him later.
At dinner, I happened to mention that I was reading a Dickens novel called Bleak House, and he raved about it. We'd both read Great Expectations and The Old Curiosity Shop, and we talked about them for a while. We were also old movie fans, and we started talking about Jimmy Stewart and Spencer Tracy movies. The subject of Cary Grant came up, and I said, "He's dreamy," just to sound like a woman.
I'm interested in a lot of things that guys my age don't care about, and it was nice to have someone to discuss things with. "I can't believe how much we have in common!" I said, and I was sincere.
After dinner, we took a little walk in the park. I kept looking for someplace to sit down because my feet were killing me in those high heels. All the benches were occupied, and I wasn't about to sit on the ground. That'd be all I needed, to get Mom's dress dirty, and Mom wondering where the dirt came from.
There was a little pavilion that had some carpeting on the floor. I sat on the ground and waited for him to join me.
"You look so incredible in that pretty dress," he said. "We should be on a picnic together. That dress would be perfect for a picnic."
"Thank you. You're so sweet," I said because it seemed the kind of thing a woman would say. He sat down next to me. We enjoyed the view together.
"Mark," I said, "I want you to know that I've never had sex with anyone but my husband and our first time was on our honeymoon night. I don't have sex outside the bounds of matrimony."
He was a bit taken aback by this, but I'd been thinking that I should say this to him. I thought I'd better make it clear that I wouldn't be having sex with him.
"And by the way," I said, "sex is anything that requires EITHER ONE of us to take off our clothes. Understand?"
He was disappointed, but he agreed.
When the date ended, he drove me back and walked me to the door. He wanted to know when we could go out again.
"I'm working all weekend," I said because my mom would be home all weekend.
"How about Monday evening?"
"OK. Pick me up at seven?"
"It's a date."
I went inside and wondered why in the world I'd agreed to go out with him again. I didn't even put up a fuss. What was I doing?
George came into the living room and asked, "How did your date go, Mommy?"
"We're going out again on Monday."
"You're going out with him again!?"
"You want to pass sixth grade, don't you?"
I went upstairs to my mom's bedroom to take off her pretty dress and hang it up.
OK, I admit it. I enjoyed his company. I didn't enjoy wearing dresses, but I enjoyed his company. And it's nice to be appreciated, and it's nice when another person finds you attractive. I wasn't likely to get that from any of the girls in my high school. I was never popular with girls, and it was good to be well-liked by someone, even if one of the reasons he liked me was that I had nice legs and looked pretty in a dress.
It was just two people going out to dinner together. And if he was paying for dinner, the least I could do was wear a cute dress and look pretty for him. What's the harm?
On Monday George was staying over at a friend's house, so I could get ready for my date without him bothering me. I was going to wear another twirly dress, but I thought, for a change, that he might like to see me in something short and sexy. I picked out my mom's shortest dress. It was still floral, so I thought Mark would love me in it.
When Mark showed up, I said, "Like my dress?"
"Your slip is showing."
"Oh, sorry," I said, fixing my skirt. "It does that sometimes, you know, on account of it being, you know, short. Which is kind of why I thought you might like it. My dress, I mean."
"I see."
"You never answered my question. Do you like my dress? You've never been shy with your opinions before."
"You look very nice. Let's go."
Was he pissed off about something?
We ate at a nice restaurant that was not too far away from where we'd had our first date. All throughout the meal it seemed that something was bothering him. I thought we could go for a walk in the park again and talk about it.
After dinner,, I headed for the park, and he headed the other way, back to his car.
"Aren't we going for a walk again?" I asked.
"Oh, sure. Of course," he said.
We went by the pavilion, and I kneeled on the ground, even though it wasn't very comfortable, and invited him to join me.
He seemed reluctant.
"What's wrong, Mark?"
"Caitlin, I know I should love your sexy dress; I know that any other man would, but I don't. I miss the twirl."
"The twirl?"
"Caitlin, from the moment I saw you, I was captivated by your femininity. Any woman can wear a slutty dress; forgive me for saying so, but you were born to wear beautiful, frilly, twirly dresses."
I stood up and said, "So my legs are ugly? Is that what you're saying? You want my legs covered up?"
"I was afraid you'd take it like this."
"No. You're right, Mark. I don't belong in a dress like this. I was going to wear a dress and a nice twirly skirt. I only wore this for you. I thought you would like it. Between you and me, it's not easy to breathe in this dress."
"Caitlin, I just want you to be yourself."
"I'll tell you what. From now on, I'll make sure to do a twirl for you before we go out to dinner. If it doesn't twirl, I'll wear something else. Unless, of course, you give me special permission to wear something tight and sexy. Deal?"
We had a little laugh over the misunderstanding.
When the date was over, we made another date for Wednesday, since Mark had afterschool events on Tuesday and Thursday. George wasn't home yet. I stood in front of the mirror in Mom's bedroom, looking at myself in that tight floral dress, wondering all over again what in the hell I was doing. This was starting to get unhealthy. Maybe I should stop dating him. This could only lead to trouble.
The next day, George took home a math test. He showed me the grade. He got a C-. Instead of answering any of the questions, he wrote down "You're dating my mother" in every blank.
Halfway through the test, he got tired of writing it out, so he just entered YDMM.
"Get rid of that," I said. "Don't let Mom see it."
On Wednesday I was standing in front of Mom's closet in a slip, trying to pick out a dress. George came in the roto.
"Get out of here!" I said, trying to cover myself up.
"Oh, don't get your pantyhose in a knot. I've seen you in your slip before. What pretty dress are you wearing tonight for your boyfriend?"
"He's not my boyfriend!"
"Wear that one," he said, pointing at another short, sexy dress.
"He doesn't like me in those dresses. He said he wanted to see me in something twirly. Like this."
I picked out a red dress and held it close to me.
"That's not sexy," he said. "Wear something sexy. You want to keep him happy."
"To him, this is sexy," I said. "You'll see."
I slipped into the pretty red dress just in time as Mark rang the front doorbell.
"Let him in," I said.
"Why don't you?"
"I have to make my entrance."
George rolled his eyes and went downstairs to let in my date.
When Mark was seated, I came flowing into the room in that pretty red dress.
"Hi there," I said.
"Oh my gosh!" said Mark. "You look absolutely incredible! I see you took our little talk to heart."
"You realize, don't you, that you're about the only man in the world who would be this thrilled to see me in a conservative dress like this."
"Yes, I know. You're going to look so wonderful out there on the dance floor."
"There's a dance floor?"
"The place we're going to has a dance floor, and you couldn't possibly have worn a more beautiful dress to dance in. All eyes will be upon you."
I gave George an I-told-you-so look, but of course, all George cared about was that his teacher was kept happy.
Comments
Jerry
I read the entire story, and I wanted to know how it ended, but eeeeww. George(bully). Mr. Johnson(creep). Caitlyn(bent). Dana(manipulative). They were all made for each other. The lesbian love interest was the only one that had boundaries and was straight forward with her intentions. That was really messy and felt like a bacchanalian free for all. Eeeewww. Winning. It felt very real life. Oh well
My Freeze
Sorry, don't care for the story line.
