Tommy - The Trials and Tribulations of a Girl? - Chapter 01

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Tommy
The Trials and Tribulations of a Girl?

A Novel By Teddie S.

Copyright  © 2017 Teddie S.
All Rights Reserved.


Preface

I started this story a few years back, and then my muse took a LONG vacation. But I eventually wrote a couple of new stories. Then I discovered the beginning of this story hiding in a folder on my computer. So I decided to see where it would go if I started working on it again. Well, what had 2 Chapters and about 12,000 words when I found it, now has 37 Chapters and over 180,000+ words and is still growing. My longest story ever. Like most of my stories, this one is sweet and sentimental with a few stumbling blocks for our hero/heroine. And, as usual, I’m open to constructive criticism.

This story takes place in the 1950s and 1960s. And I must apologize to the Native Americans that might read this, but because of the time frame, I used the terms Indian and native, as was used ‘50s, instead of the preferred Native American or First Peoples/First Nations.

There are some terms that you’ll see that you may not know:

- All the way - Having intercourse.
- Arroyo – A water-carved gully or channel.
- Cherry - Pristine, Totally Clean.
- Ditz - An Idiot.
- Fox - An outstanding looking girl.
- Make Out - A kissing session.
- Petting - Kissing, embracing, and fondling.
- Puppy Love - The love between a young couple within a few weeks of meeting.
- Ragtop - Car with a convertible top.
- Ride – Car.
- That school up north - The University of Michigan (if you live in Ohio).

Now the story. This is the story of Tommy, who, when we first meet him, is a very curious twelve-year-old. He has to know about everything, how it works, why does it feel like this, what happens if I do this, and so on. One day he asks his mother, what’s it like to dress in pretty things? And, as happens, once he starts dressing in pretty things there is no going back. But what’s behind this? Is he a cross-dresser, or is there something more behind it. Why does he want to do it more? Why does the girl next door like it when he dresses in pretty clothes? Why does he feel he is the girl that he’s dressed as? Why do all of his friends and family accept this part of him? Will a trip to New Mexico answer some of these questions, or will he have more questions than answers when he returns home? Will there be another girl, another spirit? Will he or she find himself or herself? Will he like what he finds?

This story is a work of fiction. All of the people and events are a figment of my imagination (a scary thought). Some of the places are imaginary, and some are not.




Tommy
The Trials and Tribulations of a Girl?

A Novel By Teddie S.

Copyright  © 2017 Teddie S.
All Rights Reserved.


Chapter 1

How it all began.

My name is Tommy or Tom, I’m an only child, and I was born in 1945. And this is a story of my first twenty-one years or so of my life. I’m not going to bore you with the first twelve years. Except to tell you that I was a very inquisitive child growing up. I had to know how things worked. Why things did what they did. How it felt to do something differently. My two favorite magazines were Popular Mechanics and Popular Science.

Being curious did get me into some trouble. I’d take something apart and not be able to get it back together, like when I took my dad’s windup alarm clock apart and couldn’t get it back together, or when I almost burned the house down. For the most part, my parents wrote everything off to me just being a “curious child.” I did get punished for some of the things I did.

It was 1958, and shortly I’d be turning thirteen. School had just ended for the year, and this was the first day of summer vacation. And right after breakfast, as we usually did on weekdays during the summer, mom and I had taken my dad to work and came back home. We did this so my mother could have the car. We did have two cars, and one was a station wagon, but the other one was, as dad called it, ‘his baby.' It was a 1953 Chevrolet Corvette convertible, and he didn’t like to drive it to work, who could blame him. The station wagon was a ‘58 Chevrolet Brookwood.

My mother worked part-time at the largest department store in town. And, the days that she worked she would take me to my Aunt Linda’s house so that I wouldn’t be alone. Aunt Linda had always watched me on the days that mom worked and I didn’t have school. When mom finished work, she’d pick me up, and then we’d pick dad up from his work.

My mother and I were very close, and sometimes I’d lay on her bed, and we’d talk as she was getting ready for work. No, I didn’t watch her put her clothes on. We’d usually talk as she sat at her dressing table in a slip, putting on her makeup, and fixing her hair. I liked watching her do these things. We usually talked about all kinds things, school, friends, family, and other stuff.

That Monday morning, I was laying on her bed as she put on her makeup, and we were just chatting. And I asked her, “Mommy. Why can’t boys dress in pretty things?”

“Pretty things. Honey, what pretty things?”, she asked.

“Dresses and stuff.”

She looked at me, and said, “Honey. Boys just don’t wear dresses.”

“Why?”

“It’s just not done. Boys wear boy’s clothes, and girls wear girl’s clothes. Why are you asking?”

“I see all the girls at school in their dresses, and the ladies and girls at church. They always look so pretty. You and Aunt Linda always look so pretty. So, does Mary. And, all the boys get to dress in are ugly boy’s clothes.”

“So, you think boys should dress in dresses too?”

“I don’t know. Maybe ... Just maybe everyone should just dress and look how they feel.”

“Do you want to dress in pretty clothes?”

“I ... I don’t know. Sometimes maybe.”

“So, you’d like to know what it’s like to dress like a girl?”

“Yeah. Maybe. But I’d get laughed at.”

“Why?”

“Because I’m a boy. And, as you said, boys don’t wear girl’s clothes.”

Mom let the subject drop.

It was a quiet ride that morning to my Aunt Linda’s house. When we arrived, my mother walked into the house with me. Usually, she didn’t. After I had said hello to my Aunt Linda, I ran off to find my cousin Mary.

Mary is two years older than I am, and I think she's beautiful. She was watching something on television, and I received a nice smile when she saw me. And she said, “Hi Tommy.”

“Hi, Mary.”

“Mother said we're going shopping and out to lunch.”

“That'll be fun.”, I said.

I liked shopping. We’d sometimes go to the store where my mother works, and other times we'd go to other stores. And, going downtown was always fun. There was always fun things to see. All kinds of stores to go in. The tall buildings. The big hotels. The people.

I sat and watched television with Mary. Later my mother and Aunt Linda walked into the room. Mom walked over to me, hugged me, and said, “Honey. I have to run. We’re going to meet for lunch, so I’ll see you then.”

“Okay, mommy.”, I said as I gave her a big hug.

Later my aunt called Mary to come and help her with something. I picked up one of my uncle’s Popular Science Magazines and started looking at it. There was an interesting article about a new IBM computer in it. Mary was back in about fifteen minutes, she looked at me, and smiled. And I asked her, “What?”

“Oh, nothing.”, Mary replied.

A little while later we had parked my Aunt Linda’s car downtown and were walking down Main Street towards the stores. As we walked past the peanut shop, the smells were incredible.

We walked further down the street and saw the window displays at the store where my mother works. As usual, they were great, showing off the latest in clothes, swimwear, and stuff like that. We walked into the main floor of the store, and there were a lot of people there.

My mother did a lot of different things for the store. She worked the sales counter for makeup, perfume, and things. Sometimes she would work the sales floor in ladies things. She would even run the elevators from time to time. And she also modeled clothes for the store, so we’d see her picture in the newspaper and even on television. Even my Aunt Linda and Cousin Mary modeled for the store. I told you they were pretty.

It was about eleven, and we found my mother in the ladies department, and she told us that she could break for lunch in an hour and would meet us in the restaurant on the second floor. So, Aunt Linda, Mary, and I looked around, and as usual, we started in the ladies department and wandered into the young ladies department. There was a lot of pretty things to see.

An hour later we were on the second floor and walking into the restaurant. My mother had a table for the four of us, and we joined her. As we were eating, my mother asked me, “See anything interesting today?”

“Oh not really. We were just looking at dresses and stuff.”, I replied.

“I thought you liked that kind of stuff?”

I started to say, ‘I do.’ But I caught myself. I know my face turned red. And, I just looked at my mother, she smiled, and said, “It’s all right honey. I told your aunt what we talked about this morning.”

“Oh.” And, I caught a smile from my aunt and cousin.

“So, what did you see that you liked?”

“I ... I ... I guess a lot of things.”

“You like pretty things?”, Mary asked me.

“Yeah. Kind of.” I felt my face get warmer.

“Don’t get embarrassed.”, my Aunt Linda said. “It’s not a bad thing to admire pretty things. A lot of men do.”

“Really?”

“Yes. And there’s nothing wrong admiring those things. Tommy, have you ever been to an art museum?”

“No.”

“Well, there are a lot of pretty things there, not many clothes, but other pretty things. I know it was a long time ago that Mary was to one. I’m going to have to take you two.”

“I’d like to go too.”, my mother said. “Can we do it on a day that I’m off.”

“Sure the four of us can go, and make a day of it.”

“That would be fun.”, Mary added.

“I have this Friday off. Would that work?”, my mother asked.

“That would be perfect.”, my aunt said. “Would you like to go to the museum in Cleveland?”

“That would be great.”

“Good. The museum opens at ten. Why don’t I drive, so that Chuck can have your car, and Mary and I can pick you and Tommy up at nine? That way we won’t have to rush.”

We finished lunch, my mother went back to work, and Aunt Linda, Mary, and I went shopping. We looked at more ladies and girls stuff. It didn’t bother me too much looking at these things. A lot of them were gorgeous.

As we left the store, we walked back up the street, and the peanut shop called to me. So, we stopped and purchased a small bag of fresh roasted peanuts in the shell to share.

Mom picked me up after she was done with work, and on the way to pick up my dad, she asked, “Did you have a good time today?”

“Sure mom. I always do.”

“Good.”

We picked up my dad and headed home. When we where home, my mother gave me some packages to take to her room.

Tuesday and Wednesday were regular days, mom dropped me off at my aunt’s house, and my aunt, cousin, and I did things. We spent one day at the lake swimming. And another at the zoo.

On Thursday when we left for my aunt’s house, my mother had me help her put some bags in the car. Then as we drove towards my aunt’s house, my mother, out of the blue, asked, “Honey. Do you still want to find out what it’s like to dress in pretty things?”

“Ah. ... Yeah. ... Maybe. Why?”, I answered.

“Well, I did talk to your aunt the other day about what you told me on Monday. I hope you don’t mind?”

“No. She's like my second mother.”

“We thought that it might be fun for you to spend a day dressed as a girl.”

I felt a knot in my stomach, as I said, “A ... A whole day!”

“Yes, honey. We thought that it would help you see what it was like.”

“Oh. What did Aunt Linda say?”

“She thought it would be fun too.”

“Does Mary know?”

“Yes. Mary thought it might be fun to have another girlfriend or maybe a younger sister for the day.”

“But I’m not a girl.”

“Honey, we know. We just think you’re curious about girl’s things. And it would be a way for you to find out about them. I could just tell you that you can’t do it. But, after talking with your aunt and knowing you, I thought that it might be better to let you find out for yourself.”

I sat there and thought for a minute. Then, I said, “Okay mom. I guess we can do that.”

“I thought you might say that.”

“When?”

“I thought Friday.”

“Friday! Aren’t we going to the museum?”

“Yes. We thought we could make it a girl’s day out.”

“But people will see me.”

“So. We’ll be in Cleveland. Forty miles away.”

“I guess.”

“I bought you a few things, and your aunt is going to try them on you today to see if they fit.”

“Is that what’s in the bags?”

“Yes, honey.”

“Mom. What about my hair?” I wore my hair like a lot of boys did, in a crew cut. A short crew cut.

“What do you think we should do?”

“I don’t know. But your hair is always so nice, so is Aunt Linda’s, and Mary’s.”

“Thank you sweety. I think your aunt may have an idea.”

“Oh?”

“You’ll see.”

“Okay.”

When we arrived at my aunt's house, I helped my mother carry the bags into the house, and Mary met us at the door. She smiled, and said, “Hi, Tommy. Hi, Aunt Jean.”

In unison, we both said, “Hi Mary.”

We walked into the house, set the bags next to the steps to the upstairs, and went to the kitchen. Aunt Linda was waiting for us. She looked at my mother, and asked, “What did he say about the idea?”

“You liked it. Didn’t you Tommy?”, my mother said.

“Uh huh. I’m just worried about going out in girl’s clothes.”

“Tommy.”, my aunt said. “If you’re uncomfortable as to how you look, we just won’t do it. Okay?”

“Okay. But would we still go to the museum?”

“Sure, honey.”, my mother replied.

Mary grinned, and said, “So, I’m going to have a little sister?”

“But I’m a boy.”

“Tommy. On Friday I think you’ll be a girl. Or, at least you’ll look like one.”

“Really?”

“Yes.”

My mother left for work. And my aunt asked me, “Tommy. Do you want to see if we can make you look like a girl?”

“I guess ... ”, I replied. “I guess we can try.”

“I think we can do this.”

“What do we need to do?”

“Take you, and the bags that you brought upstairs, and see what we can do.”

Mary took my hand, and with a grin, said, “Come on little sister.”

I held back a little, and said, “Mary. You’re just too anxious.”

“I am. I want to see what my little sister is going to look like.”

We grabbed the bags and went upstairs to my aunt's bedroom. I set the packages on the bed, and my aunt carefully took everything out of the bags and laid it on her bed. As she did, she said, “Your mother bought you two outfits.”

“Two!”, I asked. “Why two?”

“So that we can see which looks the best.”

“What are they?”

As she picked up the various pieces, my aunt said, “The first one, is this cute pleated, black and gray plaid skirt, a white blouse with puffy short sleeves, and a yellow vest with a black belt.

“The other one is this cute red poodle skirt with a black polka dotted ruffle at the hem, a black blouse with red piping and the letter “T” embroidered on it in white, a wide black belt, and a matching black polka dotted neck scarf.

“She also bought you a pair of black and white saddle shoes.”

“Why so much?”

“Because she loves you and she knows that you’re curious. So, she’s helping you to find out.”

“I guess.”

As my aunt handed me a bag, she said, “She also found these for you.”

I looked in the bag, and there were two packages in the bag. I took the first one out, and it was a package of seven panties in various pastel colors. I looked at my aunt, and just said, “Panties?”

“Sure honey.”, she said. “Girls wear panties.”

“Oh. Okay. I guess.”

Then I took the second package out, and it contained a bra. A pretty pink bra. Again I looked at my aunt, and said, “A bra?”

“Sure.”, she replied. “A girl your age has breasts and wears a bra, maybe a training bra. But she wears one.”

Mary added, “I’ve worn one since I was ten.”

I felt my face get red, as I said, “I ... I don’t know. Panties are one thing, but a bra. I … I can’t.”

Mary took the bra from me, and said, “Little sister. To make those outfits look right, you need to have something up top. And this is only an A cup. Want me to help you put it on.”

“Okay. I guess I’ll try it.”

“Take off your shirt and t-shirt.”

I did as she asked, then she held the bra up to me, and said, “Put your arms through the straps.”

I put my arms through the straps, then she said, “Turn around, and I’ll fasten it for you.”

I turned around, and Mary fastened it. The tight strap around my chest felt funny, as did the straps over my shoulder. Then Mary said, “See. There's nothing to it. Now turn around, and let's see.”

I turned back around, and my aunt and cousin looked at me, and both nodded their approval. Then my aunt said, “She needs a little padding. But, just a little.”

Mary smiled, and said, “Yes she does.”

“Padding?”, I asked.

“The bra doesn’t have any form to it, so it needs something to fill out the cups a little.”

“Oh.”

My aunt walked over to her chest of drawers, took something out of one of the drawers, and walked back over. She had some nylons in her hand. She walked up to me and put one in each bra cup. Then she stood back with Mary, they both looked at me, and Mary said, “That looks much better.”

My aunt smiled, and said, “Yes it does. Tommy, pick out a pair of the panties and go into the bathroom and change, then we can try on the clothes.”

I picked up the package of panties and chose the pink pair. I guess I chose those because they matched the bra. Then I went into the bathroom, removed my pants and undershorts, and slipped the panties up my legs. I was surprised as to how soft, and light, they were. I looked at myself in the bathroom mirror and was surprised as to how the bra looked on me. I took a close look and smiled a little.

I went back out to the bedroom, and we tried on the first outfit, it was the one with the pleated skirt and yellow vest. I put on the blouse, the skirt, the vest, and the belt. The skirt hit me just below the knees and felt weird at first. My aunt then had me put on a pair of short white socks and the saddle shoes.

Aunt Linda and Mary looked me over, and Mary said, “Not bad. But, the hair, or lack of it, ruins the whole look.”

My aunt walked over to her closet and came back with a blond wig. She carefully placed it over my head, brushed it out a little, and put it in a ponytail. Then, she looked at Mary, and asked, “Any better?”

Mary smiled, and said, “Yes. Much better. Even cute better.”

I thought, ‘Cute?’

“Tommy.”, my aunt said. “Go look in the mirror on my closet door.”

I walked over to her closet. Feeling the skirt move around my legs was strange. I stood in front of the mirror and just stared. There was a blond, blue-eyed, girl looking back at me.

My aunt finally asked, “Well Tommy. What do you think?”

“I ... I ... I don’t know.”, I replied.

“Do you see a girl?”

“Uh huh.”

“Like her?”

“Uh huh.”

“Come back over and let me add a little to it.”

I walked back over to my aunt, and she took a tube of pink lipstick, applied it to my lips, and showed me how to blot it. Then, she looked at me carefully, walked over to her closet, rummaged through a box, and came back with a pair of glasses with a black frame with rhinestones on them. She handed them to me, and said, “These are costume glasses and have plain glass lenses in them. Put them on, and let's see how they look.”

I slipped the glasses on and looked at my aunt and cousin.

A big grin slowly grew on Mary’s face, and she said, “Hello little sister.”

“She does look good. Doesn’t she.”, my aunt said.

“She does. She’s cute.”

“Why are you calling me she?”, I asked.

“Honey.”, my aunt said. “Go look in the mirror.”

I turned and walked back over to the mirror, and really couldn’t believe what I was seeing. I saw a cute girl.

“Mary.”, my aunt said to my cousin. “Run downstairs and get my Polaroid camera. Her mother isn’t going to believe this.”

As Mary ran out of the room, I said, “Aunt Linda. I’m a boy. Not a girl.”

“Honey.”, my aunt said. “I know. What did you see when you looked in the mirror?”

“I guess, a girl.”

“Honey. If I didn’t know better, I’d say that you were a very cute girl.”

I felt tears well up in my eyes.

“Honey. Don’t cry.”, my aunt said. “What’s wrong.”

“I’m ... I’m a boy. Now I look like a girl. It’s not right.”

“Honey. We’re doing this because you wondered what it was like to wear pretty things. And maybe being pretty doing it. If you don’t want to do it, say so, and we’ll stop.”

“I’m sorry. It just scares me a little.”

“Scares you. How?”

“That I’m a boy, and can look so much like a girl. And ... And I kind of like it.”

“Like it?”

“Uh huh. I ... I like how I look. And how the clothes feel.”

My aunt smiled, and said, “Honey. Don’t worry, and there’s nothing to be scared of.”

Just then Mary came in with the camera, and my aunt took some instant pictures. It was interesting seeing the photos of that girl. Well, I guess it was seeing me as that girl.

Then, my aunt, had me put on the poodle skirt outfit. And when I turned around, and Mary saw me, her hands went to her mouth, and she said, “My God. You look fantastic in that. Mom, we can't call her Tommy when she looks this cute.”

“I know. I’ve been thinking about that. That blouse has a “T” on it. So, it has to be a name beginning with a “T.”

My aunt looked at me, and asked, “Any idea honey?”

I just shook my head no.

My cousin also shook her head no, but then said, “Mom. What about Tammy?”

I looked at her and shook my head no.

“Why not. It’s close to Tommy.”

“I don’t know. It just sounds funny.”

“Funny?”

“Yeah. I’m a boy named Tommy. Not Tammy.”

Then she said, “Okay. How about Tony?”

I shook my head no again.

“Trudie?”

I shook my head no again.

“Tina?”

I shook my head no again.

Mary put her hands on her hips, and said, “Little sister. You’re impossible.”

“Sorry.”, I said. “I guess, maybe Tammy. It does sound like Tommy.”

My aunt nodded yes, and said, “It’s up to you honey. I like it too.”

“Tammy? Yeah. I guess if I do this, I can’t be Tommy. So, yeah, Tammy.”

Mary just shook her head, and said, “You’re a blond.”

I looked at her and smiled. Then I walked over and looked at myself in the mirror, and I was shocked. The girl that I was seeing was even cuter than before. How could I look like this? And, even more, why did I think it was fun? And I kind of liked it.

We took a few more Polaroid pictures to show my mother. And my Aunt Linda even put me in some of the poses that they would use when they model clothes for the store.

After we’d looked at the pictures, I asked, “Aunt Linda?”

“Yes, honey.”, she replied.

“How do I act like a girl? I mean, if we go to the museum tomorrow, people will see me as a girl, but I’ll be acting like a boy.”

“Mom.”, my cousin said. “She’s right. Let me work with her for the rest of the day. And I’ll see if I can bring the girl out.”

“Bring the girl out?”, I asked.

“Tammy. I saw the way you looked at yourself in the mirror. At first, it was in shock, and then that turned into a big smile. And you started looking at yourself like a girl would. And, I think, if you're willing, I can help you act more like a girl.”

“You think so?”

“Yes.”

“What will we have to do?”

“Are you willing to stay dressed like you are for the rest of the day?”

“Ah. ... I ... I guess I could.”

“If you do. I’ll correct everything that you do wrong. We won’t try to make you act like a one-hundred percent girl, but we’ll get the rough edges off. You’ll have to be willing to do everything that I tell you. Deal?”

“Deal.”

The rest of the day we spent with Mary teaching me girl’s things. How to sit. How to walk. What to do with my hands. That I needed to smile more. How to keep the long hair out of my eyes. How to put on lipstick. I learned to sit with my legs tucked under me. How to eat taking smaller bites. And stuff like that. Mary was a real taskmaster.

I was going to change before my mother picked me up, but my aunt and cousin talked me into staying dressed in the poodle skirt outfit until she came. When my mother showed up, I hid from her. I could hear my mother and aunt talking, but couldn’t understand what they were saying. Mary finally came, took my hand, and said, “I think your mother is going to be surprised.”

“I bet she will.”, I replied.

Mary then led me into the kitchen, and she said, “Aunt Jean. I’d like you to meet your daughter, Tammy.”

My mother's back was to us, she turned around, and started to say, “Hi Tam ... “As she saw me, she stopped talking, her eyes became big, and her mouth was wide open.

I smiled, and said, “Hi mommy.”

“Ah. ... Yeah. ... Hi, Tammy.”

“What’s wrong?”

“Nothing honey. I was just surprised at seeing how cute you are.”

She walked over and looked me over. Then, she looked at my aunt, and said, “Linda. I thought that the poodle skirt outfit would be a good look on her. But not this good. How did you make her look so cute?”

“It was easy.”, my aunt replied. “The wig, glasses, and a little lipstick. Plus the skirt, blouse, and shoes, helped. Both Mary and I were surprised as to how cute she looks.”

“Aunt Jean.”, Mary said. “It was cute watching him when he saw himself for the first time. And she’s listened to me on how to act like a girl.”

“Honey.”, my mother said to me. “How does it feel to wear pretty things and look so cute?”

I smiled, as I said, “It scared me at first. But it feels good.”

“Scared you?”

“Uh huh. I’m a boy. And boys shouldn’t look like girls.”

My mother smiled, and said, “Honey. It’s all right. You’re curious about something, and you’re investigating it. Now. You’d better go and get changed. We need to pick up your father.”

As Mary and I were leaving the kitchen, I heard my aunt say, “I think he enjoys looking like that.”

And then I heard my mother say, “I wondered if he would.”

Mary and I went back to my aunt's bedroom so that I could change back into my boy's clothes. We carefully packed both outfits, the shoes, wig, glasses, and everything else, back into the bags that we'd brought with us that morning. And Mary helped me remove the lipstick.

As we were saying goodbye, Mary said, “See you tomorrow little sister.”

I smiled at her, and said, “See you tomorrow sis.”

On the way to pick up my father, I asked my mother, “Does dad know anything about this?”

“No honey.”, my mother replied. “He doesn’t. And probably shouldn’t.”

“Okay. It’ll be our secret.”

“Yes. Our secret. And you know, I was amazed as to how cute you looked.”

My dad’s only comment, when we picked him up, was on seeing the bags of clothes, “Not more clothes?”

Mom said, “No Chuck. It’s just some things Linda gave me.”

Thursday night I slept exceptionally well. In the morning, I ate breakfast with my parents like I usually do. Dad was going to drive himself to work, and mom and I were going with my aunt and cousin to the art museum in Cleveland.

After my dad had left, my mother, in a serious tone, asked, “Do you still want to go to the museum dressed as Tammy?”

“I’m not sure.”, I replied.

“Why aren’t you sure?”

“I’m still afraid that someone will see me as a boy in a dress.”

“I doubt that. When I saw you yesterday, I didn’t see a boy. But you did spend all day yesterday in a dress, and I thought that would be enough.”

“Maybe it was. But, ... “

“But what honey?”

“I liked doing it.”

“You did?”

“Yeah. I guess I shouldn’t like it. Should I?”

“Honey. I don’t know. Were you comfortable doing it?”

“I was with Aunt Linda and Mary.”

“What about going out in public today?”

“I’m still a little scared.”

“That’s not a bad thing. It’ll help you to be careful not to let anyone see that you’re a boy.”

“I know. That’s what scares me. Mommy, how do you feel about this?”

“Honey. I think this may only be a phase. It may be that you're only curious about these things. But, there may be more to it. We'll just have to wait and see.

“And, while you're finding out, I'm willing to help you in any way that I can. And, after seeing you yesterday, I don't think you need to worry about anyone seeing you as a boy. Always remember there are a lot of people who won't understand. So, being a little scared isn't a bad thing. It'll help you remember what you're doing.”

“I love you, mommy.”

“I love you too.”

After I’d taken my shower, I was back in a pair of panties, and my mother helped me put on the bra, again stuffing it with nylons. Then I put on the poodle skirt outfit.

Then came the blond wig. My aunt had left the ponytail in it, and so did my mother. She brushed it a little and sprayed a little hairspray. Then she sprayed a little perfume on me. And I said, “Mommy. That smells nice.”

“I know honey.”, she replied. “It’s my favorite.”

She was going to put my lipstick on for me. But, I told her that Mary had me do it a few times yesterday and that I'd like to try. She smiled, as she handed me the tube and watched me apply it. Then I slipped on the glasses. When I was done, she just smiled at me and nodded her head yes.

I asked her, “Mommy. What’s wrong?”

“Honey. Nothing really.”, she replied. “It’s just seeing you look so much like a really cute girl.”

“Is that wrong?”

“Honey. How do you feel about it?”

“It's ... It's kind of funny. I’m a boy. And I’m standing here looking like a girl.

And ... And ... I do kind of like it.”

“You like looking like a girl?”

“Yeah. It’s fun. And it feels kind of good.”

“Feels good?”

“I like the feel of the clothes. They feel nice. And I like how I look.”

She just smiled, then said, “I have something else for you.”

“What?”

She walked over to her closet, came back with a small bag from her store, and handed it to me. I looked inside and took out what was in it. It was a red poodle purse that matched my skirt. I looked at my mother, and said, “Mommy. A purse?”

“It’s something every girl needs. And you’ll need it to carry things.”

“Things?”

“Yes. Your lipstick. Some tissues. A compact. And other things.”

“A compact?”

“Your aunt didn’t powder your face?”

“No. I don’t think so.”

“Look in the purse.”

I opened the purse, looked in it, and there was a small box. I took it out and looked at it. Then, I opened it, and it contained a round, pink, container. I looked at my mother a little puzzled.

She smiled, and said, “It’s a compact. Go on open it.”

I looked at it and fumbled with it for a minute. My mother then took it from me and showed me how to open it, and she said, “Honey. It's a compact. It has face powder, a small mirror, and a pad to apply the powder. If you wore makeup, it's used to set the foundation. Or, it can be used to hide a shiny face.”

“Oh.”, was all I could say.

“Here. Let me show you.”

She took the pad and wiped it across the powder in the compact. Then she applied the powder to my face. Then, she said, “See honey, that's all there is to it. Now look in the mirror.”

I looked in the mirror, but I couldn't see much if any, difference. And I said so. So, my mother said, “This powder is close to your natural skin color, and all it did was even out your coloring. So, you won't see much of a change.

“Normally a girl your age doesn’t wear much makeup. Maybe just a light lipstick. But today is special, so a little more makeup is all right.”

When my aunt and cousin arrived, they were early, so they came in the house. And, when my aunt saw me, she said, “Tammy. Honey. I just can’t believe that you can look so good as a girl.”

“She is just so cute.”, my cousin added.

I think I blushed. Then Mary looked at my nails, and said, “Tammy. Honey. Your nails are just so plain.”

“What do you mean?”, I asked.

As she held her hand out to me, she said, “Look at mine, honey. Aren't they pretty?”

I looked, and she had painted them a lovely pink. It looked very nice. So, I said, “That’s very pretty Mary.”

“Aunt Jean.”, Mary asked my mother. “Could I paint her nails a light pink?”

“Well.”, my mother said. “She is a little young for that sort of thing. Go ahead and do her nails for her. It’s a special day.”

Mary looked close at my nails, and said, “Aunt Jean. Do you have any pink nail polish? And maybe a nail file?”

“Sure honey.”, my mother said. “I’ll meet you in the kitchen.”

Mary and I went to the kitchen, and my mother met us there with a bottle of nail polish and a nail file. As Mary worked on my nails, she chastised me for biting my nails. And, when she was done, I had ten nails with two coats of pink polish on them.

My mother and aunt looked at them and gave their approval. And we headed for Cleveland and the art museum. The drive takes about an hour, even though it’s only forty miles.

When we arrived at the museum and parked the car, I was nervous about getting out of the car. And, wasn't going to do it, until my cousin said, “Little sister. You're with people who love you. And believe us when we tell you that no one will know that you're not a girl. You are very cute, and if you remember what we did yesterday, I don't think you'll have any problem.”

My mother then said, “Tammy. Believe what Mary said. I wouldn’t do anything to hurt you. You wanted to find out want it was like to look pretty. And believe us when we say that you are beautiful.

“I was surprised that after you spent yesterday dressed as a girl, that you wanted to go through with this. But the three of us will support you.”

I looked at each of them in turn and then said, “I'm sorry. Let's do this.”

I finally was able to get out of the car, and we spent a nice time at the museum. We even ate lunch there. But something scary happened. I had to go to the bathroom.

So, I whispered to my mother, “Mom. Where are the bathrooms?”

She pointed and said, “Right over there honey.”

As I went to get up from the table, I said, “I’ll be right back.”

Mary also stood up, and said, “I’ll go with you.”

“You can’t!”

“Why not?”

“You can’t go into the men’s room.”

With a big grin, Mary said, “Little sister. You can’t either.”

“Huh?”

“Who are you right now?”

“Oh.” And I started to sit down.

“Come on. It’ll be all right.”

“I can’t use the ladies.”

“Honey. You can.”, my mother said.

Mary took my hand and started leading me towards the ladies. I didn’t want to make a scene, so I went along with her. We walked into the ladies room, and I looked around. Then Mary said, “Go on. Use one of the stalls.”

“Oh. ... Okay.”

“Be sure to sit.”

“Huh?”

“Remember, what I told you yesterday. Girls sit to do their thing.”

When I was done, Mary was at the counter freshening her lipstick. I walked over to her and washed my hands. Mary looked at me and said, “You need to remember to bring your purse with you. Your lipstick needs freshened up.”

We went back out and rejoined my mother and aunt.

The museum did have a lot of pretty things. Even some dresses. Some very old dresses. And they were beautiful. They had a lot of paintings, wall hangings that my mother called tapestries, and other things. They also had old armor, even armor for horses. I was interested in how they made the armor, so I was looking closely at them.

While I was looking, I heard a woman say to my mother, “She’s interested in that armor. Isn’t she?”

My mother told the woman, “She’s very curious, and wants to know how things are made and how they work.”

“That’s very interesting for a girl to be that way.”

“Yes. And we encourage her.”

On the way home, we were talking about our day ...

~o~O~o~

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Comments

One of the best and most fun

One of the best and most fun outfits ever, Poodle skirts, blouses or a White or Colored T-shirt to contrast with your skirt, containing the first letter of your name; a colored scarf holding your ponytail; and either black and white or brown and white saddle shoes. White "Bobbie socks" were worn or colored Anklet socks of some sort.
My kid sister had a Red skirt with a White Poodle, my favorite was a light Gray with a Pink Poodle.
The skirts came down to below the knees around two-three inches and were flared out.
Too bad that type of clothing style has not come back around for Pre-teen and Teenage girls of today.

Tammy

Wish I would have done this with my mom when I was twelve. I used to try to wear her clothes but they were a little too big for me. I think she knew but never said anything. I grew up in the same era as this story and cross dressing was a taboo back then. At 14 her clothes fit me really well and I was fortunate that she had a wig. I was too scared to come out so I've lived with my secret for almost 60 years. I still enjoy dressing up once in a while always hoping my wife of 45 years never finds out.

I think my mother knew. And

I think my mother knew. And my wife knows and supports me. I feel very lucky.

Teddie

1945 a good year to be born

Like Tammy, I was born in 1945. The picture reminded me of a 1959 song by the Playmates: What is Love? The next words are "five feet of Heaven in a pony tail." I have a 1959 jukebox and that song is on it. I played it over and over while I read your story.

Thanks for the journey back in time.

Pentatonic

I was also born in 1945. And

I was also born in 1945. And I remember the song What is Love?

Teddie

A Younger Girl

I am one of the "younger girls" reading this story, I sense! A 1953 baby. Oh, what fun! How I wished to be a pretty daughter or niece (both!) for a day- well longer. This is a sweet story off to a wonderful start. My mother had to know- after all, we were sharing her slips and more. My wife knows but sadly prefers not to play with Kimmi as she did for a number of years.

Double thanks. I think even

Double thanks. I think even if our mothers didn't let on that they knew. Mothers know all.

Teddie

I guess

Jamie Lee's picture

It's interesting that when asked Tommy's response was, "I guess." Not no or yes but neither a negative either. It's as though he really wanted to dress as a girl but not quite sure.

He likes what he sees in the mirror and the feeling of the clothes, but why does he have this reaction? Has he had feelings for some time which have now surfaced once he was dressed or because it's something new, a new feeling?

Others have feelings too.

Hi Jamie Lee,

Hi Jamie Lee,

Thanks for the comment. And, yes we all have had those feeling at one time or another. But, as you said, why has Tommy? Time will tell.

Teddie

Lovely story

Really enjoying the story, thanks so much for writing and posting it. I also took apart my Dad's alarm clock and never got it put back together, lol.

A side note; thanks but your apology for the use of the word "Indian", "instead of the preferred Native American or First Peoples/First Nations", is not necessary. Those terms were invented by whites in an I guess well-meaning attempt to be more politically correct or polite, but are not preferred by almost any actual Natives and are not and never been in any official use. The reservations are still called Indian Reservations, the government office is still called the Bureau of Indian Affairs, etc. If you Google it, you'll find most Indians will say "we prefer to be called by our tribes, after that, Indian, or American Indian". I know I do. Most consider how they are and have been treated to be more important than what they are called. My grandfather and other relatives were born and raised on a reservation. Proud to be Cherokee INDIAN. Thanks again for the great story. :)

Hi Sheri,

Hi Sheri,

I picked up what I thought was the correct term for the indigenous peoples of North America somewhere. So thank you for the correction. I won't change it now but will remember it for the future.

I know that the Navajo People don't like Navajo but prefer "Diné" meaning “The People” or “Children of the Holy People”. But I went with Navajo as it's what most people know them by.

Teddie