One day, when I was ten and Isabel was eleven, we were upstairs in her bedroom hanging out. She didn't look too happy, and I asked her what was wrong. She took a bag out of her closet and tossed the bag at me. I caught the bag and looked inside. Inside were four training bras. There were two white ones and two pink ones. I literally felt my heart start racing just by looking at them.
They were the prettiest things I had ever seen. I was so jealous! Oh, what I would have given to have been her, to have my mother go shopping and bring me home some training bras!! But no, not Isabel. She was defiant. She wanted nothing to do with what was in that bag. This was crazy to me. I said, "Well, I think they're pretty, Isabel. You know, girls are lucky that they get to wear all kinds of different things. Boys just get to wear jeans and t-shirts." Even though we were best friends, and even though I was clearly not the most masculine of boys, it was the first time I had ever said anything like that.
Part of me wished I could take back what I had just said, but I knew it was too late. Isabel looked at me with a new, knowing look in her eyes.....She said, "Well, Jamie, if you think these bras are so great, maybe YOU should wear one!" I blushed and said, "You're a girl Isabel, and bras are for girls.
Like it or not, girls wear bras. You'd might as well enjoy it." Isabel paused for a moment, and then said, "I'll make you a deal. I'll try it on if you do too." I said that was silly, I wouldn't do it. But she persisted. "Please? I know my mom asked you to help make me more girlish. This is a perfect opportunity for you to do that!"
How did I let myself get talked into it? Well, I wanted to try that bra on more than anything in the world, so it was not that hard to persuade me. I just had to make it LOOK like it was hard. So, I grudgingly relented. After all, this was my best friend, and if it would make her happy....
The next thing I knew, we were both standing there with our shirts off, helping each other try on the bras. Isabel clearly felt was no embarrassment in standing in front of me with her top off. But even though I desperately wanted to, I was still very embarrassed about putting on a bra in front of her. Isabel made me wear the pink one, and she put on the white one. Lol as if a white bra were somehow less girly than a pink one!
It is hard to explain how the simple act of putting on a piece of clothing can be transformative, but it was. My whole body felt like it was tingling. And, while I had always felt attracted to girlish things and femininity, especially things associated with my mother, I had never before felt completely, utterly feminine.
It was as if, by putting on this one piece of clothing, I was transformed into another person. And that person, I was totally convinced, was the REAL me. Standing there wearing this tiny piece of clothing that was covering part of my chest, I felt soft, and sensuous, and submissive...
I was in my own world, in a bit of a fog, when I looked over at Isabel. And here was the crazy thing. It looked like she was having similar emotions! I couldn't be sure, but all of a sudden, everything about her seemed softer. It was as if by the act of putting this bra on, she finally let her guard down, let herself feel the pleasure of being girlish, and it was having a real impact on her. We both looked at each other in a funny way, kind of like, "Are you feeling what I'm feeling?" I spoke to her in a quiet voice. "See, not so bad, right?" She nodded. And she said, "You look cute." And I said, "So do you..."
I was not sure what would come next. We were in new territory, and things felt a little awkward. But I certainly did not expect what happened next. Suddenly, Isabel's door flung open, and Auntie Anne stood there, talking away. It took her a moment to digest what she was looking at, and then she stopped in mid-sentence. I tried to hide my chest by crossing my arms in front of me, which just made me look more girlish, if that were possible. Auntie Anne stood there with her mouth open.
Then she said, "Well, don't you two look adorable! Jamie, Honey, I always knew you would be a positive influence on Isabel. Isabel, I'm glad you have finally decided to try on one of the bras I bought you!" Auntie Anne made it sound as if it were natural for her nephew to be wearing her daughter's bra, but I was totally mortified.
Especially with all the teasing she had done in the past, I just had a feeling that I would never hear the end of it. It was one thing for Isabel to see me this way, but Auntie Anne was a different story.
She said, "You two, don't move a muscle. I will be right back!" Two seconds later, she was back with her mobile phone, and the next thing I knew, she had taken a picture of me and Isabel. "Wait til your mom sees this!" she said.
I begged her not to send it, and she laughed, "Oh Jamie, don't be silly. You think your mother doesn't know her son? The one who sits and watches adoringly while she puts on her makeup? I promise you, she will not be surprised. And if she IS surprised, she will not be upset." I said, "But, but Auntie Anne, I just did this so Isabel would put on the bra.
You told me to help her!" Even as I was saying this, I realized how lame it sounded. I was resigned to my fate. Mother would shortly receive an email from Auntie Anne, with a picture attached of her son wearing a training bra.....oh my, what would she think?
Isabel approached me. "Oh, Jamie, I'm so sorry! I didn't mean for my mom to see this. And for your mom to find out!" She hugged me. We were still both wearing nothing above our waists but our bras. In all the hundreds of hours we had spent together, I don't think we had ever hugged each other like this.
I don't know what I was feeling, but it felt like this embrace alone was worth the embarrassment I had just been through...something had changed between us...the only person I had ever felt truly close to had been my mother, but now I felt a real bond with Isabel...If you had asked me at the time, I could not have put it into words, but I somehow felt that with her trying on the bra, and with her approaching puberty, Isabel was now ready to explore her feminine side, and that I would somehow be her partner, maybe even her guide, in that process.
A moment later, my cell phone buzzed. I picked it up and saw that I had a message from my mother. I was afraid to look at it. Finally, I opened the message. All it said was, "So cute! :)"
My heart was still beating a mile a minute, and I was very nervous, but I felt my mother's love and acceptance coming right through that phone. And at that moment, I knew that everything was going to be ok....
I took the bra off and put my t-shirt back on. I came downstairs, and Auntie Anne said, "You know, Honey, you can keep that bra if you want!" Isabel came to my rescue and said, "Mom, stop teasing him!" Auntie Anne giggled and said, "I'm not teasing, I'm completely serious!"
I ran home, where Mother was waiting for me with her beautiful smile and her warm embrace. Talk about a merger - at the sight of her, I ran to her and just sank into her arms!! Yes, this was the place I most wanted to be!
While she was holding me, she said, "You know, Honey, if you ever want to talk about anything, I am here for you." I nodded my head, which was resting on her chest. And she said, "You know I love you more than life itself."
With that, I started not just crying, but sobbing. I managed to blurt out "I love you too, Mommie," in between sobs. It was the first time I had called her Mommie in years. Mother held me closer, and I could feel her crying too....
Nothing more was really said about the bra incident, and yet, it seemed that things had changed between Mother and me. I think she took it as a signal that she could be more open about sharing her feminine things with me. It wasn't that she was actually trying to make ME more feminine, but she was more open and enthusiastic about sharing that side of herself with me. It was little things.
Like, if she went shopping during the day while I was out at school, she was excited to show me what she bought and to ask my opinion.
She would be all girlishly enthusiastic about modeling some new outfit she had bought, and of course, I was the perfect audience. I always noticed, and would love how she would quietly put on a little makeup before modeling the new outfit for me!! Somehow, that made me feel special.
I would always tell her how I loved what she bought, and how beautiful I thought she looked in it! If she wanted someone to actually offer constructive criticism, she had the wrong person! (lol for that she could turn to Auntie Anne!)
She would then share her knowledge with me, explaining how this top went with that skirt, or how this dress flattered a certain type of figure. I could tell that she loved it when I asked questions, like whether boots looked better with a long skirt or shorts, or if silver jewelry went better with certain colors of clothes and gold with others. When were big hoop earrings appropriate, and when was it better to wear something more subtle?
Once, she launched into a whole dissertation on accessories and how important they were. It was as if I were a pupil in her finishing school. But finishing school for what? What was I being prepared for?
Sometimes she waited for me to get home from school, and she took me with her. On more than one occasion, we stopped by the cosmetics counter at Bloomingdale's, and she would try on some new makeup and ask my opinion. I was so flattered, because it was clear that my opinion mattered to her! The first time she did this, I was embarrassed, but soon I got used to it, and I became more forthcoming with my opinions. Every once in a while, she would pick up a lipstick, try it on, and ask me what I thought.
Once, almost absentmindedly, she said, "This would be a good color for you." There was an awkward pause, where we both realized what had happened. Instead of thinking of me as her gentle, somewhat feminine son, Mother had somehow subconsciously slipped into thinking of me as her daughter.
I kind of turned away, embarrassed, and she said, "I'm sorry, Honey, I don't know what I was thinking." I said, "That's ok, Mom, no biggie." And that was the end of it.
Thanksgiving was approaching.
The whole family was going to be going to my grandparents' for a big dinner. There were lots of aunts and uncles and cousins, including boys and girls who were both younger and older than me and Isabel (who was a year older than me.) I didn't really dislike anyone, but Isabel and Auntie Anne were really the only ones I was close with.
Anyway, as the day approached, Mother told me that she wanted me to look especially nice for dinner this year. I usually didn't spend too much time on my appearance, but if looking 'especially nice' pleased Mother, it was fine with me.
Little did I know what she had in mind. She said that she had bought me some new clothes. I thought that given how she loved to model her new clothes for me as soon as she bought them, it was a little odd that she did not show me what she had bought for me. But I really did not think too much about it.
The night before Thanksgiving, I was sitting with Mother in the living room watching TV.
She was doing her nails. Most women had their nails done at one of the many nail salons in the area, but not Mother. She loved to do her own nails. And I loved to watch. Of course, I tried to act like I wasn't watching, but I don't think I fooled her. She had dozens of bottles of nail polish, and if I was there while she was doing her nails, she usually asked me to help pick a color.
I always thought the nail polish color names were so much fun! Names like "I'm Not Really A Waitress" and "Pink A Doodle"! I wondered if someone could make a living being a professional nail polish namer!
If so, that was the job I wanted! This evening, Mother suggested that we pick something that had a bit of an orange color in it, in honor of Thanksgiving. We chose Bright Lights Big Color.
Mother finished up her nails. She called me over. "Honey, come over here and sit down next to me." I got up and came over. She picked up my hand and inspected it.
"You know, just because you are a boy doesn't mean you can't keep your nails nice and neat. Here, let me give you a little manicure." I started pulling my hand back, and she said, "Relax, Honey, I am not going to put any nail polish on. I just want to fix you up a bit. Trim your cuticles, file your nails, give them a nice shape.
And here, this is nail hardener to make them nice and strong." All this seemed ok with me, but then she took out a bottle of clear polish. I said, "But you said no polish!" And she said, "This is just clear, Honey. Men get that all the time when they get manicures! No one will even notice!" So I let her put the clear polish on me.
With the more oval shape she created, the cuticles pushed down, and the clear polish, my nails looked beautiful and very feminine! You could definitely see the clear polish every time the light hit the nails; they gleamed!
I had such mixed emotions! Trying on the bra was almost like playing a game - it was really because Isabel had dared me to. And while what Mother had said was right - men DID get manicures with clear polish, this still felt like an unmistakable step towards something more feminine.
On the other hand, I was in LOVE with the way my nails looked! I was secretly hoping that Mother would actually suggest a little color, just to see how it would look, but it was not to be....
The next morning was Thanksgiving. After lounging around for most of the morning, Mother told me it was time to get ready. She still had not shown me the clothes she had bought me. When she came into my room with a bunch of boxes and started opening them, I knew why. The outfit was totally girlish!
The pants were a burgundy velvet. They had no fly and had a zipper in the rear. They flared out at the bottom. There was no question that these were girls' pants!
I could not believe that Mother was making me wear these pants to Thanksgiving dinner!
The shirt well, it wasn't a shirt - it was a blouse - was gold silk. The sleeves were very blousy and were only half-length. It was beautiful, but very feminine. There was no way anyone would mistake this for a boy's shirt.
The shoes were low-heeled, shiny black patent leather, with a pretty gold buckle. I recognized the design from reading Mother's fashion magazines - it was Tory Burch.
For underneath, Mother gave me a new pair of white cotton panties, with a little bit of lace trim and a tiny pink bow in the front, a matching white cami, and sheer black knee-highs.
Except for that one incident with the bra, I had never worn any girls' clothes or makeup, even secretly. And even though this outfit could technically be worn by a boy - I mean, it was pants and a shirt, not a dress, it still screamed, well, what it really screamed was not girl, so much as "sissy". And Mother expected me to go out like this, to a big family dinner? I looked at her like she was crazy.
"Mother, I don't know what you were thinking, but I cannot go to Thanksgiving wearing these clothes! I will be laughed out of Grandma's house!" Mother said that was ridiculous, that no one would laugh at me, that there was nothing wrong with a boy looking nice, "well-groomed" as she put it. I resisted a little more, but it was no use. Mother was adamant, and I was not very good at opposing her in any event.
Mother helped me get dressed. I was conscious of my nails as I put my clothes on. I noticed how they shined, and how slim they made my fingers look. In my mind, I couldn't help thinking what nail polish color would go with the outfit.
Oh, my, that was not a good sign! As I got dressed, it felt like the outfit was doing to my body what Mother's manicure had done to my nails. I felt sleek and feminine. Feline.
Once again, I had conflicting emotions. On the one hand, the truth was, I loved how I looked, and I loved how the silk and velvet felt on my skin! Part of me loved the fact that it was hard to tell whether I was a boyish girl or a girlish boy!
For some reason, I found that ambiguity to be very exciting! On the other hand, I was dreading seeing my whole family like this! I was quite sure no other boy at the dinner would be dressed in a silk blouse and velvet pants! My only hope was that Isabel would come to my rescue!
Before we left the house, Mother gave me one of her slim gold watches to wear. It was beautiful, and I felt very grown up, but it was clearly a lady's watch. And then she said, "It's a shame your ears are not pierced; I have a perfect pair of earrings for this outfit!" OMG, my heart was racing! Pierced ears, and lovely earrings! But I knew that would never happen....
As we left the house, Mother said, "Oh, Honey, you look gorgeous! I know you are a little nervous to go out like this, but everything will be fine! You look fantastic!" And she kissed me, and we headed to the car.
We got to my grandparents' house, and parked the car. Before we left the car, Mother took her lipstick out of her purse and applied it. It was a pretty, light frosted pink. As always, I gazed at her while she did that. Looking at Mother applying her lipstick was something I had long ago given up trying to resist, because I knew I was simply unable to. After she finished with the lipstick, she took out a tube of lip gloss.
The color in the tube looked pink and sparkly, but Mother said that it went on almost clear. She put in on over her lips, and then turned to me. "Honey, face me and close your eyes." OMG, was Mother going to put the lip gloss on me? Wearing an androgynous outfit was one thing, but lip gloss? To a family dinner? I was upset, almost crying, and I begged her not to put it on me.
"Please, Mommie, I wore the outfit just like you asked me to. Please don't put the lip gloss on me!" But Mother had a vision of what she wanted me to look like, and she was not to be deterred. "Shh, Honey, I am just going to put a tiny bit on. No one will even notice!" And before I knew it, I felt the sticky pink wand gliding across my lower lip.
"Now press your lips together. That's it! Good girl!" As she said the last, I looked at her in horror. "Whoops," she said, "Sorry. Just kidding!" With that, I started crying again.
"Mommie, please! I'm not a girl!" Mother spoke soothingly to me. "I know you're not Honey. You're my sweet, special boy. But Mommie knows what's best. Mommie also knows that her sweet boy is upset, but that he is also thrilled that he is getting to wear Mommie's lip gloss. Isn't that right?"
I paused for a moment, thinking about what she had just said. "Couldn't I just wear things like this in the house, with just you and me?" Mother replied, "Well, I suppose you could, but I think you are just too precious to keep to yourself.
I want to show off my pretty boy to the whole family! Now be a good boy and stop crying, and let's go inside!"
We stepped inside. There were lots of people already there, and there was a general tumult. But after a few greetings, the room started getting quiet, as everyone started noticing me. I felt my face go flush. Mother spoke. "Doesn't Jamie look handsome? See, Honey, I told you everyone would like your outfit!" Handsome?
I might have looked pretty, but I didn't look handsome, and everyone in the room knew it. There was an awkward silence, when finally Isabel stepped in, grabbed my hand, and said, "Come on, Jamie, let's go exploring." And with that, we escaped the room.
We went upstairs to the attic, a favorite haunt of ours. She said, "Oh my God, look at you!! You look, well, you look pretty! Your outfit is gorgeous. And...lip gloss??" I groaned. I said, "I know, this was all my mother's idea. I am so embarrassed!" And she said, "Well, you shouldn't be.
I, for one, think you look awesome." And then I noticed for the first time that Isabel looked awesome herself. The old tomboy was gone.
She was wearing a pretty gray pleated skirt and a pink cashmere sweater set, with pearls, no less!! She looked like quite the young lady, and even in my girlish outfit, I felt a pang of envy! I was so confused! How could I be mortified at wearing girlish slacks and a blouse while at the same time be jealous of a girl's skirt and sweater set?!
"Oh, Isabel, you look gorgeous too! Look at you, all grown up and ladylike!" Isabel giggled and said, "If you behave yourself maybe I will let you borrow the outfit!" It was if my best friend had just read my mind!
I smiled, and we hugged each other. I wished we could spend the whole day up here in the attic, but I knew that sooner or later we would have to go downstairs and I would have to face the music, enduring the stares and smirks of my family members.
As we all sat around the dining room table, I felt like all my senses were heightened. I could feel the soft cami under my silk blouse. When I reached to pass the bowl of mashed potatoes, I could see Mother's slim gold watch on my wrist, and I could see the light from the chandelier reflecting off the clear polish on my nails.
At least my lip gloss had worn off! I was acutely aware of the furtive glances, especially from some of the older cousins. And Jimmy, one of my cousins who was a high school football player, couldn't hide his look of disgust. I saw his mother shooting him warning glances, and that seemed to be enough to have him not actually say anything.
Still, the day basically passed uneventfully, and shortly after dinner, Mother and I left to go home. I was pouting in the car, feeling as if I had somehow been punished, even though I had done nothing wrong. Mother tried to make me feel a little better.
"See, that wasn't so bad, was it?" But I was not to be mollified that easily.
"Yes, Mother, it WAS that bad! Everyone was staring at me, and Jimmy couldn't stop shaking his head at me! Mother smiled. "I don't know, Sweetie, I think some of those boys were jealous of how nice you looked! Maybe even Jimmie! He likes to think of himself as a tough guy, but I'll bet he would not have had the guts to dress so nicely!" To which I replied, "I didn't have guts either, Mother! You made me!" Which basically ended our conversation til we got home.
That night, Mother tucked me into bed. She gave me a gentle kiss on the lips, one that lasted just a fraction of a second longer than was appropriate. She had not taken her makeup off yet, and I could feel her lipstick on my lips. The brief kiss was enough to send my head spinning. Not only that, for the first time, I felt a stirring down in my boy part. Mother whispered to me, "Honey, I know today was a little hard for you, but I was very proud of you. I know you don't completely understand why I dressed you that way today.
All I can say is, I think it is important for you to be who you are, and not to be ashamed of who that is. Goodnight, Darling." I wondered what she meant as she turned off my light and closed my door.