Nothing much happened for the next few weeks. But I knew Isabel's birthday was coming up. She was turning twelve. I had been spending less time with her lately. Since that day when she first put on the bra, Isabel had undergone a transformation. She had discovered her girlish side, and with that, she had become much more popular.
She now had lots of pretty girlfriends. I was a little envious of how pretty she was, of her girlfriends, of the fact that she got to wear pretty clothes. I kind of wished I were her.
One day, I came home from school, and Auntie Anne was there, talking conspiratorially to Mother. When they saw me come in, they stopped their conversation. There was not too much Mother would not say in front of me, so I was a little suspicious. I went upstairs to my room to work on my homework.
A little while later, I heard Auntie Anne leave, and Mother came upstairs and knocked on my door. I said come in, and she sat down beside me on the bed. I said so, what's the big secret? And she said no secret. Honey, here's the thing. Isabel is having a birthday party in two weeks. She is having what's called a fancy dress party. Do you know what that is? I shook my head no. She continued.
Well, it's kind of just like the name. The girls wear fancy dresses to the party. It's a chance for them to get dressed up. I did not know where this was going, or why this was of any interest to me. Mother continued.
So, Isabel is going to have eight or nine of her girlfriends to this fancy dress party. But the thing is, she also wants her best friend there. And that person is you.
I responded, I don't know, Mom, I don't know about going to a party with a bunch of girls. I was trying to put on a tough guy act, but of course I wanted to go to a party with ten girls wearing pretty dresses.
I hoped it would look convincing when I finally agreed to say yes. I said, but I guess for Isabel, that is a sacrifice I can make. Mother smiled. Well, that's very noble of you, kind sir. But I don't think you are getting the whole picture.
You see, Isabel wants you there, but she also does not want to ruin the mood of a girls' fancy dress party by having a boy there. As the saying goes, she wants to have her cake and eat it too. At this point, I was confused. I did not know what Mother was suggesting. She continued.
Anyway, Isabel was telling Auntie Anne of her dilemma, and she said, too bad Jamie's not a girl. That would solve everything. And Auntie Anne said, what if he dressed like a girl? Isabel thought that was a brilliant suggestion, and she begged Auntie Anne to talk to me. Apparently, they both think I can persuade you to do it.
I was aghast. It was bad enough that she had dressed me like a sissy in front of the whole family. This was a completely different matter. She was talking about having me wear a dress. To a party with a bunch of girls. I told her that there was no way I was ever going to do that, that they could all just forget that crazy idea.
I had put my foot down and I felt good about it. Enough was enough. I was not a sissy. And there was no way I was going to wear a dress to a party.
But that was not the end of it. Mother was very disappointed in me, and she let me know it. She said that she did not think it was such a big thing to do for my best friend, and that she thought my refusal to do so was selfish.
My self satisfaction at standing up to Isabel, Auntie Anne, and Mother soon turned to sadness. I felt that I had disappointed all of them. But most of all, I simply couldn't bear the idea of Mother being unhappy with me. It had created a distance between us.
When I got home from school, she was no longer waiting there to show me her latest outfit. I felt terrible. Was she punishing me for not doing what she wanted? Maybe. In any event, it was working. I came home one day from school, feeling miserable, and told her, okay, I would do it.
Her attitude changed immediately. She ran to me and hugged me tight.
Oh, Jamie, I just knew you would do the right thing. Don't worry, we are going to have so much fun getting you ready.
I promise you, you will be the prettiest girl, with the prettiest dress at that party. I wasn't quite sure that was what I wanted, but I did know that seeing Mother that happy was what I wanted. Under the category of if you can't beat them, join them, I decided to just go with the flow. Minutes later, Mother was on the phone with Auntie Anne.
They sounded like two schoolgirls. I heard Mother say yes, yes, he's going to do it. Yes you were right. No it's not true that he would do anything for me. He's doing it for Isabel. With that she turned towards me and winked, letting me know that she knew I was doing it for her, because there was nothing I would not do for her.
All day long at school I wondered exactly what I had gotten myself into. During lunch, Isabel saw me in the cafeteria. She said, Jamie, my mom told me you will come to my party. Umm, dressed for the occasion. With that she hugged me and said, Jamie you are my best friend. I just want you to know how much it means to me that you will be there. Thank you for doing this for me.
When she did that, it made me feel that Mother had been right, that I really had been selfish not to put my best friend first. But now I felt better about my decision.
When I got home from school, Mother was waiting there for me. She could barely contain her excitement. She said she had gone shopping and brought home five dresses for me to try on.
Oh my god, I could not believe this was actually happening. My mother had gone dress shopping for her son. And I was going to go to a birthday party wearing a dress. How did I let myself get talked into this?
The dresses were all laid out on her bed. They were all absolutely gorgeous. I could not believe I was about to try them on. I was scared, but very excited. It helped that Mother seemed even more excited than me. She said, I told you you would have the prettiest dress there. And believe me, when I am done with you, you will be the prettiest girl at that party.
I was scared and nervous, but this was also like a dream come true. I was going to get to wear a pretty dress to a party with a bunch of girls. I couldn't believe it.
Mother said, honey, before you try these on, you need to wear the proper things underneath. I know at Thanksgiving you wore a cami and panties, but I think with these dresses you should wear a training bra. Just like Isabel's. And over that you need to wear a slip. Mother took out a shopping bag and laid out those things on the bed as well. I had never seen a slip before it was beautiful, just like a thin, filmy dress.
Mother helped me to put on the panties and bra, and then she dropped the slip over my head and arms, and it fluttered down around my body. Mother seemed blissfully happy.
And I was lost in a dream. I could have stayed in the house trying on dresses with Mother forever. As long as I did not think about the fact that the end result would be me wearing one out to Isabel's party. The only boy in a room full of girls, but all of us wearing dresses. Oh my.
I spent all afternoon modeling the dresses for Mother. She had me stand in front of her full length mirror, and we discussed the pros and cons of each one.
I loved this dress. I know it was a little grown up for an eleven year old, but it was so much fun.
I knew I was supposedly only doing this for Isabel and Mother, that I wanted nothing to do with wearing a dress, but I could not resist the seduction of wearing this feminine finery and discussing it all with Mother. So, at some point, I just dropped the pretense that I did not want to do this, and I just went with the flow.
When I tried on the first dress, Mother took out a pretty barrette. She said, you know, I was dying to have you wear this at Thanksgiving, but I thought it might be too much. I love a barrette with short hair. I think it looks especially girlish. I thanked my lucky stars that Mother had not made me wear it at Thanksgiving, and I let her put it in my hair. Even without a dress, just one simple barrette could transform a normal looking boy into a complete sissy. It was amazing.
This was Mother's favorite. She thought it was the most age appropriate, and she liked the fact that it was a little demure.
This was my favorite dress. It was a little grown up, and almost a little too dressy even for a fancy dress party, but it was the most heavenly, feminine dress I had ever seen. I just had to have it.
Finally, we narrowed it down to two dresses, the purple and the silver. Mother then looked at me and said, you know, we could keep both of them if you'd like. I looked at her and said, why would we do that?
As it is, I am only going to wear one of them just once. And Mother smiled and said, okay, if you say so. But I think I will hold onto both of them until after the party. I could not imagine that there would ever be a reason for me to wear a dress again.
The party was on a Saturday. Mother said we would have a little day of beauty getting ready beforehand. She was going to take me to her hair salon to have my hair and eyebrows done, and then she would do my nails.
But when I woke up in the morning, the reality of what was about to happen set in, and I was paralyzed. I could not get out of bed. What had I gotten myself into?
Mother came up to my room and walked over to my bed.
What's wrong, sweetie? I said, I'm scared, mommie. I don't think I can do it. And she said, of course you can. And then she stroked my hair and gave me gentle kisses all over my face, ending with a feathery but lingering kiss on my lips. Then she said, this is your chance to be a pretty girl for a whole day. Not too many boys get that chance.
I know you will love it, sweetie. And it will make mommie so happy. Don't you want to make mommie happy? Of course I did. So, I did as she said, and I got up out of bed.
As I got up out of bed, I realized belatedly that I had a little tent in my underwear. I tried to hide it but all I did was draw attention to it. Mother was in a playful and flirty mood. Well, it looks like someone may be trying on dresses, but is not all girl. Is someone excited because they are trying on dresses, or because they like it when their mother gives them kisses? Are you getting too old for me to give you kisses? I know that Mother was teasing, but the thought that she might stop kissing me made me panic. I did not know how to respond when Mother giggled and said, don't answer that. I am just teasing you. Now, one more thing.
Do you think you would like to go to the salon in your dress? It will help the stylist with your cut.
Once again, I was panic stricken. No, mommie, please. Just to the party. She said okay, and told me to get dressed in my regular clothes and to meet her downstairs.
We were off to Mother's salon. Mother had told her stylist what was going on. My hair was not very long, but I was due for a haircut, and there was enough there for the stylist to do something.
Originally, she was going to give me a short pixie cut, something that would make me look like a girl if I were wearing a dress, but that otherwise would make me look like a boy with a somewhat girlish haircut. But after a somewhat lengthy discussion with Mother, there was a change of plans. She would style and layer my hair a bit, but the big change was going to be extensions.
The stylist was thrilled to be working on me. For years, when I had accompanied Mother to the salon, she had told Mother how pretty I was, and that it was a shame I was not a girl. She had a look of satisfaction on her face that almost said, ha, I knew it was just a matter of time before I would be doing your hair.
After my cut, Mother asked her to shape my brows. It was nothing too extreme, but she thinned them and added a little arch. I was amazed at how the eyebrows made my face so much more feminine.
This is me. After my cut and the addition of my hair extensions, and having my brow shaped. This is an old dress of Mother's that I just threw on for the picture. Of course you can see that it is big on me, and loose in areas where it fit Mother just right. Also, after seeing this picture, I worried that my dark arm hair would give me away as a boy. I hoped no one would notice.
Finally, we were on our way home. Mother said, time for us to do our nails. Jamie, if you knew how many times I resisted the urge to paint your nails after I was done with mine. Don't you think I noticed how you would look at me when I was doing my nails? And all this time I thought I was being subtle.
We picked out a color together. I wanted grape, set match, a metallic purple that I thought would go with the dress. But my mother thought a pretty pink would nicely complement instead of match the dress, and also go with my pink lipstick. Of course, I listened to her. She said she especially loved the name. Princess pink for mommie's princess. Oh, my. I loved the fact that Mother and I would be wearing the same nail polish color. And as much as I loved the way my nails looked with the clear polish, it was no comparison to wearing colored polish. I could not stop looking at my nails.
Essie's princess pink for my nails. It matched my pink frosted lipstick. I thought it looked just like cotton candy.
While I was letting the polish dry, Mother ran a bath for me. She put in some lavender bath salts, which smelled yummy and made my skin nice and soft. Finally, I got out of the tub and headed to my bedroom to get dressed. Mother told me to yell when I had my panties on, and she would help me with everything else. First came the training bra. I held my arms straight out, and she slipped it through them and then fastened it around the back. Next, the slip. Oh my, such a feminine garment.
I felt like a princess. Finally, the dress. I thought Mother would take out a barrette, but instead, she had a headband with a big bow attached. So pretty. Mother had bought me new shoes, not high heels, she said that was not appropriate for a girl my age, but shoes with a kitten heel. She said they were like the shoe version of a training bra.
I thought I was ready to go, but not quite yet. Mother took me over to her vanity. You are too young to be wearing makeup, young lady, but this is a special occasion. I told you you would be the prettiest girl there, and I meant it. So I am going to put some makeup on you, okay? I promise you, all the girls are going to be jealous, including the birthday girl. With that, Mother put some mascara on me and some blush.
And then the best part, a little blue eye shadow. Finally, she took out the pink lipstick she had worn on Thanksgiving and applied it to my lips. She had me look in the mirror, and I really thought I was going to pass out. There staring back at me was a very pretty girl. With the makeup, I looked older than eleven, maybe thirteen or fourteen. I loved it.
But loving how I looked was not the same as wanting to go outside. Once again I panicked, and told Mother I really did not think I could do this. By this time, she was having none of it. She handed me a little purse, which had the lipstick and my cell phone, and she handed me a pretty little a line coat she had bought for me. She dragged me by my hand, and we were out the door.
It was only a few blocks, but she drove me to Isabel's. I thought Mother would get out of the car with me, but she did not. She waited in the car while I walked up and rang the bell. I really felt like I was going to my execution. I was seriously worried that I was so nervous I would wet my panties. The door opened, and there was Isabel, looking radiant.
Isabel, the birthday girl, looking adorable. Her mom let her wear lipstick.
She pulled me inside and said, oh my god, look at you. You are gorgeous. She hugged me, and kissed me, and whispered in my ear that having me there was the best present she could have. Then she turned and said, girls, I want you to meet Jamie, my cousin from out of town. Isn't she pretty? And by the way, even though she is a year younger than me, notice that her mother is letting her wear eye shadow. We are going to have to have a talk with our moms.
Once I got over my nervousness, the party was so much fun. Isabel never left my side. She really looked out for me, making sure I was okay, and that there were no questions from the other girls that I couldn't answer. If I paused, she would simply answer for me. The truth is, it was one of the most fun evenings of my life. I loved being girlish, hanging out with other girls, talking about makeup and music and fashion. When they talked about boys, it made me a little uncomfortable, but otherwise, I was always a part of the conversation.
I called Mother at the end of the party and told her I could walk the few blocks home. I could tell that Mother was surprised that I was willing to walk outside in my dress. But the truth was, I felt pretty, and I loved feeling pretty, and I just wanted to walk down the street feeling that way.
When I got home, Mother gave me a big hug and asked how it went. I said, oh, mommie, I had such a wonderful time. And then I started crying. Mother looked concerned and said, what's the matter, princess? And I said, oh, mommie, what am I going to do?
And she said, don't worry, we will figure it out together. Here, I bought you something that I had a feeling you might like. And she handed me the frilliest, silky nightgown. This is for you, sweetie. You can wear it to bed. Now, why don't you go upstairs and get changed? I will be up in a minute to help you take your makeup off.
Mother tucked me into bed wearing my new nightgown. She gently kissed me on the lips and said, sweet dreams, princess. With that, I fell soundly asleep and dreamt of what might be. As long as Mother was by my side, I knew everything would be okay.