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Dressed For My Brother's Teacher - Final Part
🕑 Added 2025-02-04 13:50:49 +0000 UTCThe next day at school, I felt a glimmer of hope because Mom didn't make me wear a dress, and I was made fun of a little bit less than the day before. Eventually, it would be over.
When I got home, my Mom made me put on my lingerie and makeup and said, "Good news, young lady. I'm going to let you choose which dress you want to wear tonight."
"Swell," I said.
"Just show me what you've chosen before I have to go to work."
While she waited for me in the living room,
I went to her closet to pick out a dress. I chose the pretty red dress with a full skirt.
"Oh, good choice! You look so pretty in that dress. You're growing up to be a very lovely young lady."
"Mom, why do you have to keep calling me 'young lady?'"
"What do you want me to call you? Butch?"
"Mom!"
"Did you ever wear that dress on a date with Mr. Johnson?"
"Yes."
"I'll bet you two went dancing, didn't you?"
"Yes," I said in a melancholy voice.
"Well, I'm sure you had a lovely, romantic time. You know, my mother gave me that dress. She always said that any man worth a damn would probably fall in love with me when I wore that dress. That's the dress I wore on my first date with your father, so you can imagine it has a special meaning to me. And you decided to wear it to captivate and manipulate a man you didn't even like all that much, and all so you could make two hundred dollars."
"I'm sorry, Mom. Want me to take it off?"
"No, dear, the time for you to not wear my dresses was last week, when George offered you money to pretend to be a woman. That was when you should've decided not to wear my dresses."
"Mom, I said I was sorry."
"I'm sorry, too. I'm sorry I couldn't make you wear that dress to school so you could find out first-hand how much fun it is being a woman. But I have to get to work, now. Keep that dress on until you go to bed, or pec'iig trouble."
George came home in time to say goodbye to Mom before she left for work. It was Tuesday, so Mr. Johnson couldn't come over to tutor George because of his after-school activities.
George and I ate dinner together. I finished first, and I got up from the table and put my dishes in the dishwasher, then I headed upstairs to do my homework. George said, "Dana, if you want to take off your dress, it's OK. I won't tell Mom. I promise."
"Thanks," I said. It felt good to have one person on my side, anyway. "But I don't think so."
"I won't tell, I swear."
"You never know. She might have one of the neighbors come over to check up on me."
"Oh."
"Now, go ahead and say that I'm keeping this dress on because I like wearing dresses."
"I wasn't going to say that."
"Thanks for not making fun of me for wearing a dress, George."
"I promised I wouldn't, right?"
After we ate dinner and did our homework, there was nothing else for us to do but sit around watching television. During a commercial, I got up to get something to drink.
"How did things go at school?" asked George.
I shrugged. I was feeling optimistic.
"Not too bad. Not as bad as yesterday. Things might be getting a little bit better, or maybe the guys are just tired of making fun of me. They can't make fun of me forever."
Right at that moment there was the sound of a bunch of guys pounding on the front door, saying "Hey Princess Diana, come on out, and let's see your pretty dress!"
I looked at George in a panic.
"I'll get rid of them," said George. "Lock the back door, just in case."
I ran to the back door and locked it, then ran upstairs as fast as I could in high heels, and hid in my bedroom. Things were just starting to calm down, and I was scared to death things would get worse if one of them saw me.
George came into my room.
"It's OK," he said. "I told them Mom's not making you wear dresses anymore. They wanted to see you. I told them you were doing homework. They would've got in if I hadn't put the chain on the door."
I was so relieved. I wanted to hug him, but I was already gay enough in my cute little red dress.
"Thanks, George. I really mean that."
"Come on downstairs and watch TV," he said.
I went down with him, and we sat in front of the tube. There was a rerun of MASH playing. A woman was saying to Corporal Klinger, "I couldn't help but notice something. You're wearing a dress."
I grabbed the remote and turned off the TV.
"Hey, I was watching that!" said George.
"I don't want to see that. Please, George, I just can't watch that right now."
I was trembling.
"It's OK, Dana. I don't think they'll be back. I think they believed me."
"I just keep thinking of what they would've done if they got in here. Maybe beat me up. Maybe ripped off my dress, or just pulled up my skirt like you did once."
"I'm sorry about that."
"Every time I think things are getting better, something like that happens. You can't imagine what it was like having to take off my dress in that stall in the boy's bathroom, with all those guys watching me, laughing and whistling and hooting."
"It's OK, Dana. We'll get through it together."
"Together? I'm the one wearing a bra, not you."
Wednesday evening Mr. Johnson came in for another tutoring session. I wore the pretty peach-colored dress, and when he went into the kitchen to get something to drink, I saw my chance to needle him some more. I went in there and cornered him.
"Hello, lover," I said.
"Stop calling me that!"
"Oh, I'm surprised at you, honey. You were a lot more friendly the last time I wore this dress. Remember? It was just out there, at the back door. You kissed me and hugged me for a long, long time."
"Dana, please---"
"I seem to recall you couldn't keep your hands off my rear end."
I sat down and crossed my legs.
"Remember all the fun we had, lover?"
"Look, I'm sorry about all that."
"Are you? Are you really? You know, I don't think you are. I think you want to kiss me again. I think you're still attracted to me."
"Dana, you're just being ridiculous, and I don't have time for any of this nonsense."
But he was so nervous, he tripped on his way out of the kitchen. I laughed as I watched him leave.
Thursday afternoon I came home, and Mom greeted me, saying, "Guess what, dear!"
Whenever she was happy, it seemed to be bad news.
"What?"
"I went shopping this afternoon, and I bought you the cutest little dress!"
"You bought me a dress?"
"Well, I thought it was awfully silly for a teenage girl to have to wear her mother's dresses, so I thought I'd buy you something a little closer to what a young girl like you should be wearing. Now get your undies on. I can't wait for you to try it on!"
I changed into the lingerie and the dress.
It was OK, as dresses go. Certainly not as silly looking as the pink French Maid's dress. And it buttoned down the front, so it was easy to put on. It was just this sinking feeling that I was getting deeper into the feminine world of dresses and pantyhose, and there was no escape.
"Mom, you should've made me come with you and try it on. You missed out on a chance to humiliate me."
"Well, there's always the weekend," she said.
Friday night, Mom chose a short little floral dress for me to wear. Mr. Johnson was coming to tutor George, and she kept saying that my boyfriend would like to see me in this cute little dress. Yeah, well the joke's on her, because Mark didn't like me in that dress at all.
After Mom left and Mr. Johnson showed up, I waited until he went to the bathroom. When he came out, I was there to confront him.
"Hello, lover," I said.
"Stop bothering me, Dana."
"Oh come on now, honey. Wouldn't you like to kiss me again, the way you used to? I know I'm not really wearing your favorite dress, but I can't believe---"
"Dana, just stop it. You know, you're not that attractive, anyway."
"Oh, I'm not? So last week when you were calling me beautiful and gorgeous, you must've been thinking about someone else. So I'm not beautiful?"
"No. You're not. You can't even pass for a real woman."
"So you were just kissing me to make me feel better about being so ugly?"
"Dana, get out of my way."
I tried to block his way, but he rushed past me, almost knocking me down. Well, I couldn't blame him for being angry. Maybe I should stop teasing him. But I still wanted to make him uncomfortable on Saturday right in front of my mother, to see what the result would be.
So Saturday morning, when my Mom woke me up and told me to put on a dress, I asked if she wouldn't mind very much if I had another date with Mr. Johnson.
"Has that child molester actually asked you on a date?"
"No, but I'm pretty sure I can get him to ask me out again if I try hard enough. I've been flirting with him every time he comes over. I really miss going out with him. We used to have dinner together and go out dancing, and he'd hold me in his arms and kiss me for hours."
My Mom laughed.
"So this is supposed to get me worried that you're turning gay, is it? Well fine, if you can get him to ask you out, by all means, have a great time. Maybe you two will be getting married one day. I'll have to take out my old wedding gown and see if it fits you. If only your Dad were alive to see his only daughter getting married!"
I groaned. Mom let me pick out which dress to wear, so of course I chose the sexy tight gold dress. When Mr. Johnson came over, I waited until I could get him and my mother in the same room.
Then I came out and said, "Hello, lover. Remember this dress?"
He moaned and glanced at my mother, who was clearly enjoying his discomfort.
"Well, do you?" she asked.
"Of course I do," he said.
"I'll bet you do. You requested I wear it on our last date together. That time we spent kissing in front of the fireplace. You had your hands all over me in this dress. You were even trying to get me to take it off. Remember?"
It was pure enjoyment to watch him getting redder and redder, unable to stop blushing.
"Yes," he said.
"What say, lover? Why don't we go out again? Let's have another romantic date."
"Stop it! That's enough! If you don't stop acting like that I'm not coming here again! I don't care if you turn me in and I lose my job! I am in hell!"
I laughed. Making my best sarcastic face, I said, "You're in hell? That's a laugh! I'm the one in a girdle and nylons and three-inch heels, I'm the one who had to wear a dress to school, but you're in hell? How is that?"
"Because I fell in love with you!"
And this made us pay some attention. We waited for him to continue.
"It's crazy. I know it's crazy to fall in love with a woman in two weeks, but it happened. And now I find out that the woman I fell in love with isn't even a woman! She wears beautiful, feminine dresses, and she has gorgeous legs, but she's not a woman. And now I have to fall out of love with you, and I have to start treating you like a boy, and how can I do that when I've never even seen you wear anything but pretty, feminine dresses? How can I do that if you won't stop flirting with me?"
There was silence for a while as we took this in. Finally, my mother walked right up to me and said, "Son, I want you to take off my dress."
"And put on another one?"
"No. No more dresses. You're a boy. Boys don't wear dresses, they don't wear pantyhose or high heels, and they certainly don't wear bras."
"Do you mean it?"
"Yes. You've been punished enough. We've all been punished enough."
"And the dress you bought me?"
"I'll return it."
"Thank you. Thank you, Mom. Help me get out of this dress, would you please?"
We left Mr. Johnson and went to my Mom's bedroom, where I took off her dress. And I've not worn another dress since that time, nor have I wanted to.
I know that some people reading this might have expected that I became a crossdresser because of this experience, that I discovered that I really like wearing dresses, and needed it. But I've got news for you. Not every male is a latent transvestite. Not every man, or boy, is going to love it when he's forced to wear a dress. In fact, recently I was asked by a girlfriend to dress up like a woman for Halloween, again, and I told her no, and I had to reveal all the trauma I had gone through. She understood. Mom's punishment had worked.
When I got into jeans and a T-shirt and sneakers and got all that make-up off me, I went into George's bedroom where they were studying. I asked George to give us a minute, and he got up and left.
"So, this is what you really look like?" asked Mr. Johnson.
"Yes. This is the real me. I'm a boy."
"I've never seen you before when you weren't wearing a dress."
"I know. I'm sorry about all that flirting. I never meant to hurt anyone. I never realized you---"
"Please don't say it."
"OK. But I've got someone I'd like to show you."
I went to the door and escorted my Mom into the room, wearing the gold dress.
"You're wearing his dress!" he said. She rolled her eyes.
"It's my dress. It's not my son's dress."
"Please, have a seat."
I once said that I thought he was dating those dresses instead of me. Maybe he was.
I gave them some privacy.
As I left I heard him say, "You look wonderful in that dress."
"Better than my son?"
I didn't wait for the answer.
By the end of the school year, the kids finally stopped making fun of me and stopped calling me Diana. The boys finally stopped coming over to my house to bother me, hoping to catch me in a dress. I could go out and show them I was dressed like a boy because Mom wasn't making me wear dresses anymore.
And Mom announced that she would be getting married to Mark Johnson. We were happy for her, of course, though it would be pretty awkward having him living in the same house with me, this man I used to date. This man I used to wear pretty dresses for. This man I used to kiss on the lips, for crying out loud.
But Mom hadn't mentioned my crossdressing for months, so you can imagine the shock when she came into my room one weekend, and said, "Dana, Mark, and I have been talking it over. We think you'd make a wonderful Maid of Honor."
"What! No, Mom! I'm not doing that!"
"Now, Dana, I know what you're thinking, but the gowns I got for you and the bridesmaids are lovely. You will all look wonderful."
"No! I won't do it! I'm not wearing any more dresses!"
"Dana, look at it this way. If it hadn't been for you wearing my dresses in the first place, Mark and I would never have gotten together. So we think it's only appropriate for you to wear a pretty gown, and lipstick and pantyhose and high heels, and be our Maid of Honor to celebrate our union at the wedding."
"Oh, well when you put it that way---NO!"
"OK, let me put it this way, then. You WILL be our Maid of Honor at my wedding, so I'd suggest you get used to it!"
"No! I won't do it! You can't make me!"
"What did you say?"
"You can't make me! You can't make me!"
The next thing I knew I was face down on my bed, my Mom twisting my arm behind me. It hurt like hell, and I yelled, "Let me go!" I twisted back and forth trying to get out of her grasp, but she had a grip like iron.
"You're hurting me!"
"Will you be our Maid of Honor?"
"No! Let me go!"
"I'll let you go when you promise to be our Maid of Honor and wear a pretty gown."
"No! I won't do it!"
She tightened the grip and it hurt even more.
"Let me go!"
"Say you'll be our pretty Maid of Honor."
"Alright! Alright!"
She let me go. I stood up and rubbed my shoulder. I hated that I was so puny. Even my little brother could push me around.
"Mom, please don't make me do this."
"You're doing it. Next weekend you're going in for a fitting, so get your arms and legs shaved before then."
She left. My brother George came in and said, "What was all the yelling about?"
"She's making me be a stupid Maid of Honor!"
He threw back his head and laughed.
"You just can't keep out of a dress, can you?"
"She's making me!"
"You probably begged her."
"Ask her yourself."
"She probably can't wait for the day when she gets to see you in a beautiful wedding gown, saying 'I do' to a somgood-lookin'n' guy."
"Drop dead. You said you wouldn't make fun of me anymore."
"That was before. Now all our relatives get to see you in a gown, and everyone knows you're a boy! They're gonna love it!"
"I wish I was dead," I groaned.
"Any of the guys at school find this out, they might make your wish come true."
"Don't tell anybody."
"Don't worry. I'm not exactly bustin' with pride that my older brother wears dresses."
"I don't wear dresses! I haven't worn a dress in over two months! Why is Mom doing this to me? I learned my lesson already! I bet if I go to the cops they can stop her."
"Don't go to the cops. Go to a gym," he said and left.
Well, I didn't go to the cops, because she is my mother, after all. And the next weekend I got my arms and legs shaved. When I went into my bedroom, my Mom had laid out the clothes she wanted me to wear to go to the bridal shop for a fitting.
"Why do I have to wear a dress?"
"I'm only thinking of you. Do you really want to go into the bridal shop as a boy and say you need to try on a gown? At least this way everyone will think you're a girl."
So I got my lingerie and make-up on, and I put on the Asian-style dress Mom picked out for me. I didn't realize how skimpy it was until I had it on. I kept trying to tug it down farther. I thought there must be more to the dress than this.
I looked down at myself in the dress.
"I can't go outside in this! I'll freeze!"
"It's almost summer, Dana."
"I feel like I'm naked."
"Get in the car, son. We're going to be late. Or I guess I should call you daughter, now. Wouldn't want anyone to know."
"This isn't going to end, is it? You get a big kick out of dressing me up like a girl. I'm like the daughter you never had. After the wedding, you'll find some other excuse, and another, and another. You're going to make me wear dresses for the rest of my life!"
"Knock off the drama and get in the car."
As we were leaving, George took the opportunity to whistle and make kissing noises.
"Drop dead!" I yelled.
"George, you shouldn't make fun of your sister that way," said Mom, which just made him laugh all the more.
"Why don't you ever make him wear dresses?" I asked her, in the car.
"Don't be silly. He's a boy."
"I'm a boy!"
"Boys don't put on dresses and go out on dates with grown men."
I groaned. How long was Mom going to hold that over my head?
We got to the bridal shop, and once inside I was afraid, as usual, that everyone could tell, that I wasn't fooling anybody. I did my best to be as feminine as I could be.
There was a delivery girl who was a real knockout. Gorgeous blue eyes short blonde hair, and an incredible body in jeans and a tight T-shirt. I don't usually like short-haired women, but she was adorable, and I couldn't help checking her out a little.
She caught me at it, and I looked away in panic.
I changed into the gown. I felt like an idiot standing there as they marked and measured, and tugged the gown this way and that. My shoulders were showing, and I kept thinking everyone could tell I was a boy, but no one seemed to know.
When they were done, Mom said to me, "See? Not a bad-looking gown."
I didn't think it was all that great, but at least it wasn't too frilly.
"Mom, please tell me this is all just a joke," I whispered. "Tell me I don't actually have to appear in this stupid gown in front of all my relatives."
"You should've thought of that before you decided to start wearing my dresses."
"Mom, how many times do I have to apologize for that?"
"I'm not asking you to apologize; I'm asking you to make your mother happy on the most important day of her life, so stop whining about it."
I changed back into the skimpy Asian dress, and my Mom went into the back room to pay for the gown. I stood by the front door waiting for her. I couldn't wait to get out of there.
Then I noticed the delivery girl. She was looking at me, smiling at me. And it wasn't the kind of smile that says, "Ha ha, look at the faggot wearing a dress." No girl had ever been attracted to me before, but I could swear she was checking me out.
I couldn't help returning her look and flirting a little.
Then I looked away. I bent down to scratch my knee, being careful not to get a run in the stupid pantyhose my mother made me wear. Just out of curiosity, I looked again, to see if she was still checking me out. She was. I started flirting some more, really going into overdrive.
She started coming over! Oh man, what was going on? She was coming over to make fun of me!
"Girl, you are really something!" she said. "You've got the most incredible figure I've ever seen in my life! I could just eat you up!"
She thought I was a girl, but she was still flirting? That would mean---?
"Cat got your tongue?"
"It's just---my mother is right over there!" I said.
"Oh. So, you're not out yet? She doesn't know?"
No, my Mom didn't know I was a lesbian, and I was not at all sure she would approve of the concept. I only had a minute to decide what to do about this.
She had a delivery pad. I grabbed it from her, and a pen, sat down quick, and wrote my phone number.
<
I gave it back to her before my Mom got out of the back room.
"Call me any night except the weekend. Ask for Diana. If my Mom answers, hang up!" I said.
My new girlfriend left as my Mom arrived. As we went out, she asked me what the delivery girl wanted. I said she just wanted to know who was getting married, and I said it was my mother.
"Funny. She didn't congratulate me."
We got home, and I peeled off the skimpy dress and everything else I was wearing. I sat in the bathtub and thought about the dangerous game I was playing. I would be lying to someone about being a woman, again. I would be taking advantage of her, and I knew it was wrong, but I couldn't help myself. No girl had ever looked twice at me my entire life, and this was my chance to finally have my first date with a girl. My first kiss with a girl. Even if I had to wear dresses and pantyhose to do it. But at least I was finally getting something out of all this, other than the little bit of money George paid me, which was pretty near gone.
That Monday the phone rang. I forgot, and let George answer it. No one ever called me anymore. I used to have friends, but since it got out that I wore dresses no guys wanted anything to do with me, and I can't say as I blamed them.
George came in and said, "Oh, Diana! Phone call for you. It's a girl."
I blushed, but I said nothing to him. I took the call, using my girl's voice. We flirted for a while, and she asked me out for Wednesday night. Her name was Kris. I called her Krissy once, but she corrected me and made it very clear her name was Kris, not Krissy.
I asked her how old she was. She said she was 22, and I told her I was only 17. She didn't have a problem with that, but she said we were going to have to be discreet.
"Who the hell was that?" asked George when I was off the phone.
"My new girlfriend."
"She thinks you're a girl?"
"She's a lesbian. You know what that is, right?"
"I know what a lesbian is. I just didn't know that YOU were one."
"Don't tell Mom."
"OK, but you know you can't blame this on Momanymoree. You're wearing dresses voluntarily, now. You're not even getting paid for it."
"Who cares? I've got a girlfriend."
"Is she cute?"
"Hell yes, she's cute! Think I'd be wearing a dress for her if she was ugly?"
"Man, I've heard of guys turning into pussies when they get a girlfriend, but you are really screwed up, Dana."
"Oh, I'm screwed up? Who's got a date Wednesday night, and who's gonna be sitting on his ass watching TV?"
"You don't actually think you're gonna get laid doing this, do you?"
I had to admit that the chances of me getting laid were pretty much non-existent, but at least I'd get to make out with her.
Wednesday night came, and after Mom left for work I started getting ready for my date with Kris. She said we'd be going to an expensive place, so I should wear something formal. I grabbed my Mom's most formal outfit, her gold beaded dress. I squeezed myself into that tight dress and checked myself out in the mirror.
"See if you can resist me in this, Kris," I said to my reflection. Finally, I could feel good about looking sexy in a dress.
She picked me up in her car. She didn't seem to be dressed all that formally. She wasn't wearing jeans, but she was in comfortable slacks and sandals, which didn't seem fair to me. How come I had to be the one in a tight, uncomfortable dress, and I'm a boy?
We drove not to an expensive restaurant, but to her apartment complex.
"What is this? You said we were going to someplace expensive."
"My condo costs over a hundred thousand."
"Look, if you wanted to cook me a meal you should've said so. It's embarrassing being overdressed."
"I don't cook. I have take-out."
"Take-out! I put on a five hundred dollar dress for take-out?!"
I had no idea what the dress cost, but that sounded impressive.
She got out, then ran around the car and opened the door for me, which was nice, but I was still pissed off. Still, she was very charming all night long, and she wore down my defenses as we ate and talked and flirted.
When we were done eating, she took away the dishes silverware, and take-out cartons, and I got up from the table and strolled into her living room. She didn't have much in the way of furniture. I sat on an ottoman and tried to make myself as comfortable as I could, considering what I was wearing.
When she came in from the kitchen she caught sight of me stopped short, and practically gasped. Which was just the reaction I was hoping for.
"Wow," she said. "You have the most incredible legs I have ever seen."
"Thank you, baby. Why don't you come over here and kiss me?"
"Oh, I don't kiss on the first date."
"Excuse me?"
"I said I don't kiss on the first date."
"I squeezed myself into this tight dress and three-inch heels, I spent over an hour getting ready, you throw on some slacks and sandals and you feed me take-out, and now you won't even kiss me?"
"Look, Diana, I don't know what kind of girls you've been dating, but I wear the pants in this relationship, and I call the shots. That's the way I am, and if you can't handle it, maybe we shouldn't be dating. I love your gorgeous legs and your sexy figure, but what really turns me on about a woman is when she's submissive. If you can't be that, we don't have a future."
"Take me home," I said and stood up.
"No second date?"
"Maybe. I'll think about it. Take me home."
On the way to the car, I heard a voice coming from the second floor that filled me with terror. It was a couple of boys I knew coming out of one of the apartments!
"Hurry up!" I said to Kri and ran to her car so fast I almost tripped. I managed to get in her car before the boys saw me. As we drove out we wound up driving right past them, and I kept my hand in front of my face.
"What's wrong?" she asked.
"I know that boy. He's an old boyfriend of mine."
On the way home, I told Kris I didn't mind being a little submissive, but she had to have more consideration for me. She couldn't have her way all the time just because I'm 17. She said she'd think about it.
When I got home, George asked me how my date went. I said I didn't want to talk about it, and he laughed.
"You struck out!" he said. "You should go back to dating men! At least Mr. Johnson kissed you."
"Drop dead! I couldn't let her kiss me on the first date, could I?"
"Yeah, right."
She called the next day, and we set up a date for Friday night. I told her we'd better be going to a real restaurant this time.
Friday night I slipped into my Mom's greenish-blue dress, which was a lot more comfortable than that tight beaded dress.
Kris picked me up, and we went to a fairly decent restaurant at the mall. I realized she couldn't take me to any fancy French restaurants on a delivery girl's salary, and that was fine.
On the way to her car, we strolled through the mall, holding hands. Another experience I could cross off my list: holding hands with a girl. We went past a vintage clothing store, and Kris pointed out one of the hats, a silly-looking hat from the Fifties.
"That hat would look cute on you!" she said. "Let's go in and try it on."
"No. I'm not trying on any stupid hat. I'm 17 years old. Where am I going to wear a hat like that?"
"Who said anything about buying it? Just try it on. Come on, loosen up, and have some fun!"
"I'm not going to dress up in stupid hats for your amusement."
She yanked me into the store. She made me try on the hat and a few other ones.
I felt ridiculous, but I tried to loosen up and at least act like I was enjoying myself.
<
I tried to put one of the hats on Kris, but she would have none of it. Oh sure, I was the one who had to dress up in funny hats like a clown for her amusement. Heaven forbid she try on one.
After half an hour I finally had to sit down and relax.
"Why are you always sitting down?" she asked.
"Haven't you ever worn high heels in your life?"
"No."
"Never? Didn't your mother ever make you wear them?"
"No."
"Wow. I wish I could say that."
"I was raised by my father."
"Oh. Look, you're about my size. Why don't you try on my heels?"
"Don't be ridiculous."
"What's so ridiculous about it? You're a woman, aren't you?"
"As far as this relationship is concerned, I'm the man. You're the woman."
"What man ever said he didn't kiss on the first date? What happens if I ever felt like wearing some nice comfortable slacks on our date, like what you've got on?"
"You'd be going on the date all by yourself."
"You wouldn't be that mean, would you?"
"If I came to pick you up and you were wearing pants, you'd have to change or there would be no date."
"I see."
"Do you even own any pants, Diana?"
"Yes, I own pants. Believe it or no, I don't spend my entire life in dresses and pantyhose and high heels."
"You should, with legs like yours."
She asked me if we could get together on the weekend, and I said no because my mother would be home. She wondered if I could just sneak out, and I answered that I didn't think so.
"Well, give me a call if we can get together," she said.
"What's your number?"
"You don't have my number?"
"No. You always call me."
She gave me her number, and I asked if she had anything to write with. She pulled her delivery pad from her fanny pack, the same pad I'd used to write down my phone number for her in the bridal shop. She gave it to me, and the silly little hat on my head fell off as I reached to take it from her. She gave me a pen, and I wrote down her number.
I tore off the piece of paper and stuck it down the front of my dress.
We left the mall, and Kris drove me home. We said goodbye at the back door, like Mr. Johnson and I used to do. I made a move to kiss her.
"Next date."
"Oh, for crying out loud!" I said and went inside.
Saturday afternoon I saw that my Mom had laid out another dress for me, a shiny lavender striped dress.
"What is this about?" I asked. "Another fitting?"
"Just put it on. I'll tell you when you get dressed."
I nervously got dressed, wondering what humiliations were in store for me, now. I was lucky, so far, that none of my classmates had seen me, but my luck couldn't hold out forever.
When I was dressed, I went to my mother's bedroom for the bad news.
"Mark and I were discussing it, and we thought it would be fun if you went for one last date with your future father, before the wedding."
"Mom, that's crazy!"
"Don't make trouble, Dana."
"Mom, could we just have one moment of sanity, here? Just one moment of sanity? Think about what you're asking your son to do. Do you want me to go on an actual date with a man who's going to be living in the same house with us? In this dress?"
"Didn't seem to bother you, before."
"I won't do it!"
"Dana, I'm going to be spending the evening at my wedding shower. As Maid of Honor, you should be there, so you can either come with me to the shower or go on the date with Mark."
I knew what the shower would be like. A lot of girl cousins my age who knew I was a boy.
"Alright, fine. You win. As usual."
"Now, I'm going to need the car to get to the shower, so you'll have to take the bus to your date."
"Aw, Mom, not the bus! Not in a dress!"
"What's wrong with taking the bus? Mark's taking the bus. His car's broken down."
"Mr. Johnson doesn't have to worry about a bunch of strangers looking at him and knowing the truth about him."
So that evening I boarded the bus, carrying my quarters in my hand. I still refused to carry a purse, even after all this time and all the dresses I've worn. Once I took a seat I kept my eyes downcast, refusing to make eye contact with anyone, blushing furiously all the way to the restaurant.
I stepped carefully off the bus, and the wind had its way with my skirt and my hair.
A couple men laughed at the sight. I had to hold down my skirts and act like it was all just a big joke.
But inwardly I hoped that they'd all one day be forced to wear dresses and pantyhose like me, and we'd just see how funny it was, then.
He was waiting for me in the lobby. I walked right up to him and said, "Mr. Johnson, what the hell is the meaning of this?"
"You should start calling me Dad."
"I'll call you Dad if you stop making me wear these stupid frilly dresses."
"Calm down, young lady."
"Don't call me that!"
"Oh come now," he whispered. "You don't want me to call you a boy in front of all these people, do you?"
People were starting to stare, it was true.
"Whatever," I said. "Just tell me why you made me do this!"
"We need to get past this," he said. "We need to stop being embarrassed about the way your mother and I met."
"That's easy for you to say!"
"Look, Dana, we'll just have a nice dinner together, and it will be the last time I ask you to do this, I promise."
"It's bad enough Mom makes me do this crap. I thought I could count on a little support from you."
"Once I'm your stepfather I'll do all I can to stop your mother from making you dress this way, I promise. Now come on, let's go in to eat. They're holding our table."
"Fine, but I still don't understand the point of all this."
"I just need to spend one last evening with you this way. To say goodbye to the false Caitlin so I can get on with married life with the genuine article."
So I dated my brother's teacher, hopefully for the last time. And it wasn't too bad. He might've treated me like a daughter, but at least he wasn't being romantic with me. He was trying to get me to relax and laugh about our time together. I didn't think I'd ever be able to laugh about it, but if it helped him be a little less embarrassed about things, I suppose it was OK. Things were going to be OK between us.
On the way out I asked him for some quarters for the bus.
Monday evening Kris called, and we made a date for Tuesday night.
TOn uesday I slipped into a shiny blue dress of my Mom's. I checked myself out in the mirror.
It didn't show off my figure very well, but the color was brilliant, and I was sure Kris would love it. It was like wearing a neon light.
After dinner, we wound up back at her place, again. I was impatient to get on with the kissing.
"How would you like to turn me on?" she asked.
"Sure."
She brought out a silly-looking little girl's dress.
"Slip into this," she said.
"Oh, come on."
"Come now, Diana. Be a good little girl and put on your pretty little dress."
I went into the bedroom, and I took off my dress and slip. No slip was going to work, with that tiny dress. When I was all changed, I called her in.
"Oh, my pretty little girl!" she said. She was getting turned on.
"Kiss me, Mommy," I said.
"Just a minute. I've got a little teddy bear for my sweet little girl."
She gave me the teddy bear. I can't even begin to tell you how stupid I felt. Oh well, I'm a boy dressed like a little girl. What right do I have to any dignity?
"Hug your little teddy bear, Diana."
I laughed.
"You're a freak, Kris!" I said.
And that was ME saying that. A boy who wore dresses.
I hugged my little teddy bear.
And then there were more toys for me to play with, and Kris just kept getting more and more turned on. I wasn't about to fail when I was this close. If she wanted a little girl, I'd be the cutest, sweetest little girl she could ever hope for.
And finally, she came over to me and kissed me. I grabbed her by the back of the neck and attacked her with my lips. This was the moment I'd been waiting for, and I intended to enjoy the hell out of it. She put her tongue in my mouth, and I put my tongue in hers. I jumped on top of her and kissed her for fifteen minutes, only stopping once my lips were tired.
We were both breathless.
"Wow," she said. "Haven't you ever kissed a girl before?"
"You're crazy. I've kissed plenty of girls."
Then she started to pull down her pants.
"What are you doing?" I asked.
"Come on, you didn't think we were going to just kiss, did you?"
I had no idea what to do, but she grabbed my head and pointed it at her crotch. I was expected to put my tongue in there? Where does pee come out of? I tentatively flicked out my tongue, and I was surprised at what I tasted.
Sweet! She tasted sweet!
And I was in there like a bear in a beehive. I heard her moan so much it scared me like she was in pain or something. But when I tried to stop she wouldn't let me. Then she really started to moan. And she tapped my head, and I pulled out, her love juices all over my mouth.
She put her hand under my skirt.
"What are you doing?" I asked again.
"Time to do you, baby."
"No! No! I'm not ready!"
"Come on, baby, pull down your pantyhose."
"No! Not yet! I can't!"
"Don't tease, Diana."
"What, you're the only one who takes a little time to be ready? I said I'm not ready!"
I insisted she take me home.
Wednesday night she called, and we made a date for Thursday. I had to decide what I was going to do.
Thursday night I decided I was going to go for broke. I was going to insist that she take care of me the way I took care of her. This would almost certainly be our last date.
Since she liked little girls, I wore one of my mother's cutest dresses.
Once again we wound up back at her place. She didn't make me change. The dress I was wearing was already cute enough for her.
We started kissing. She put her hand under my skirt.
"Are you ready?" she asked.
"Yes."
She pulled down my pantyhose and panties, and there it was. She gaped open-mouthed in terror like she was in a horror movie.
"Go ahead," I said.
"You're a---you're a---you get out of my place right now or I'll call the cops!"
"Oh no, you've got that backward, Kris. If anyone's calling the cops, it's me. I'm 17, remember? You took advantage of my innocence."
"You wouldn't call the cops. Everyone would find out about you."
"Who will? My mother? She already knows, remember? No, you're the grown-up, here. You're the one who's in a hell of a lot of trouble unless you cooperate. And don't even think about telling the police I'm lying, because I saved some of your love juices!"
That wasn't true, but I wished I'd thought of saving some of her juices, as evidence.
Still, I had her, and she knew it. So she crawled on top of me, and before she began she looked me in the eye and said, "I hope someday some man makes you do to him what you're making me do to you."
Then she began. And it was so worth it. It was so, so worth it. All the aching feet, all the itchy legs, and all the bra straps digging into my shoulders were worth it for that incredible moment.
"Now, get out of here," she said.
I know it was wrong to misrepresent myself that way, and I usually like to think I'm a pretty good person. But so far, I've still been unable to feel sorry for what I did. Maybe I will, one day.
The next weekend was the wedding. All the relatives knew I was a boy, of course, and they all laughed at me and made hurtful comments, especially the girls my age. But I didn't care. I was still technically a virgin, but I'd come a lot closer to getting laid than I ever had before.
The memory of that kept me smiling throughout the entire wedding. Even that itchy petticoat Mom made me wear under my gown couldn't ruin my mood!
The End.
