I woke up the next morning feeling very confused. I had been through some very intense but interesting experiences over the past few weeks. It had all started with accepting Isabel's dare to try on the training bra with her.
I was amazed at how I felt completely transformed into this feminine, submissive creature just by trying on the bra. Isabel's transformation, from tomboy to girlie girl, was just as amazing. And, as Isabel became more feminine, my feelings for her evolved as well, from a best friend to, well, I did not know, but something more.
Mother's taking my trying on the bra as a cue for her to dress me in a sissyish way for our Thanksgiving dinner was even more traumatic. I mean, I loved that Mother was focusing all this attention on me, and I loved how I looked, even though I knew I looked like a sissy.
The burgundy velvet slacks, the gold silk blouse, the patent leather shoes, the panties, and the cami all made me feel special. But I did not want anyone else to see me that way. It was very embarrassing to appear that way in front of my family. I thought I would be ridiculed, especially by some of the older boy cousins.
Actually, at the time, I was kind of surprised that the reaction I received from everyone was relatively muted. Later, I found out why. Before the dinner, Mother had sent out an email to the family. This is what it said:
Dear All,
As all of you know, my son Jamie is a sweet, gentle boy. Sometimes I blame myself for not providing him with a male role model, but the truth is, he has always gravitated towards pursuits that most people would consider girlish, such as fashion.
I have not discouraged him because I want him to be happy, and in order for him to be happy, he needs to be himself. To that end, I have encouraged him to wear something special for Thanksgiving, something that would make his outer appearance reflect his inner self.
I have picked out an outfit for him that is just darling. I know he loves his outfit, even if he will not admit it, and is excited to be wearing it, but is very nervous that he will not receive a warm reception from the family. So, I am asking you all, please be your usual kind and welcoming selves to Jamie. He is the same person he has always been, the same one you have always loved.
Looking forward to seeing you all,
Love,
Emily
Isabel shared this email with me later, and it explained a lot. No wonder no one seemed freaked out by what I was wearing. Anyway, the trauma of Thanksgiving was soon followed by something even worse: Isabel's request and Mother's insistence that I wear a dress to Isabel's birthday party. Initially I refused, but Mother's disappointment in me and her withdrawal of affection towards me in the aftermath were devastating to me. So, ultimately, I acquiesced. Mother was thrilled to have a daughter for a while, and once I let myself go with the flow, I actually enjoyed being a girl for a day.
So, what did I learn from all of this?
I learned that the simple act of putting on a training bra could make me feel exquisitely feminine, a feeling I enjoyed beyond description.
I learned that I enjoyed having Mother dress me in a sissyish way.
I learned that, although I did not really realize it at the time, the embarrassment of being dressed that way was itself somehow enjoyable to me, some kind of odd combination of pleasure and pain.
I learned that I could not live without Mother's love and affection, and in return, I would do anything she asked of me.
I learned that dressing up as a girl, actually playing the part of a girl, was tremendously enjoyable but, in some way, felt less like the real me than the sissyish boy at Thanksgiving.
There were a lot of lessons for an eleven-year-old boy to learn in a short period of time. I felt like I needed a little bit of a break from everything to digest all of this.
And things did go back to normal for a while. Normal, except that Isabel, Auntie Anne, and Mother all looked at me differently after the party. I had been totally convincing as a girl, and that seemed to change how all of them looked at me, and therefore, my relationships with all of them changed as well.
For example, with Mother, she did not want to push things with me, but it was pretty obvious that she was the happiest I had ever seen her when she had me trying on dresses for the party. Also, it was hard to deny that in some ways, she had a newfound power; it was not just me who realized I would do anything for her. She realized it, too. I might resist, but at the end of the day, I would submit. And while it all came from a feeling of love on her part, I think there was no question that she enjoyed having this control.
Regarding Isabel, well, she had asked me for a huge favor, and even though I had initially said no, and even though I had agreed to wear the dress mostly to make Mother happy, all Isabel knew was that she wanted her best friend, a boy, to show up at her party wearing a pretty dress, and that is what I did.
So, Isabel felt gratitude towards me and affection and was protective of her younger, sissyish boy cousin. Did she feel attraction?
I was not sure. Did I feel attraction towards her? I was not sure of that either, but I think I did. Did it bother me that I might feel romantically towards my cousin? Not really. It did almost scare me how natural it felt for me to be playing the role of a girl at the party.
Actually, that is the wrong description. The whole point is, I did not feel like I was playing a role. It felt totally natural to be wearing a frilly dress and makeup and sitting and giggling with the other girls.
The only time I had felt a little awkward was when the conversation turned to boys, who had crushes on whom, and so on. At one point, they started talking about Justin Bieber. Someone said he was so cute. And someone else said he was more than cute; he was pretty. Did you see him performing on the Today Show the other day?
He had these gorgeous earrings in both ears. And did you see the lip gloss he was wearing? I would bet he would look adorable in a dress. And they all started giggling, and a third girl said, oh yes, it would be so much fun to dress him up. And I would bet he would love it. I think he secretly wants to dress like a girl.
Isabel shot me a look, and I stayed calm, but I thought I was going to die. They could just as easily have been talking about me. Anyway, it was a little tricky spending time with Isabel, because her new friends had just met her cousin from out of town, a girl named Jamie.
And if they met me in boy mode, they might or might not have made the connection, but I did not want to take a chance.
But we spent a lot of time emailing and texting each other, and I felt closer to her than ever. There were times when I would lie in bed at night, thinking of that moment when we had both tried on the training bras, and we had stood there looking at each other, like somehow the whole world had just changed. Which, I guess, it had.
Auntie Anne was another story. Even though I was not as close to her as Isabel or Mother, in some strange way, I felt like she knew me the best. It was almost like, when she looked at me with that little smile or made those teasing remarks, she was saying, Who are you kidding, sissy? You can protest to your mother or to Isabel all you want; you will never fool me. I know you are a little sissy who likes having his mommy paint his nails. It was like she could see right through me.
Like Mother, she seemed to see no contradiction between enjoying my embarrassment on the one hand and loving me on the other. Could she and Mother possibly have known that not only did I enjoy being a sissy, but also that in some strange way, I also enjoyed the embarrassment? It was all so complicated.
I could tell that Mother was encouraging me to be more girlish, and I did make some concessions to her. For one thing, we did keep both dresses, and she hung them up in my closet, so they were there staring at me every time I opened the closet door. It was as if they were saying to me, are you not tired of being a boring boy, when you could put me on and be fabulous? All glam and pretty and sexy? Go ahead, try me on.
I resisted the urge to do so, but I did make some other concessions. The biggest one was that I continued to wear the nightie Mother had gotten me the day of the party. It was like, in the evening, when it was just me and her, with no chance of there being anyone else around, even Auntie Anne, I could let my guard down a bit. We would put on our nighties and drink some hot cocoa and watch a little television, and then I would go up with her to her bedroom, and I would stand behind her while she sat at her vanity, and I would help her brush her hair with her beautiful antique silver hairbrush.
A hundred strokes, as she cooed and told me how good that felt. And then, even though my hair was relatively short, we would switch positions, and I would sit down and she would slowly, languorously brush mine, all the while softly talking away about this or that. It was always a dreamy time, when I felt closest to her. It was during those moments that I literally thought to myself, yes, I would do anything for her. Then she would take me by the hand, and I would get in bed, and she would tuck me in. I would close my eyes, and she would lean over and gently kiss me on the lips. There were times, during the day, when I would spend hours thinking about that one second of my day. And there were times, at night, when I would awake, sweaty, with my boy part hard, realizing that I had been dreaming about that one second as well.
And then the final concession. After my kiss, Mother would always say, goodnight, princess. And I would say, but mommie, I am a boy, I cannot be a princess. And she would say, only special boys can be a princess, sweetie. And you are the most special boy of all. Every night, the same routine. And then she would quietly walk out and shut the door.
Christmas was approaching. This meant a few things. First, the extended family had two big get-togethers a year. The first was Thanksgiving. The second was Christmas. I did not want to raise the subject with Mother because I was afraid to hear what she was thinking. But I was really hoping that we would not have a repeat of Thanksgiving. I mean, from my point of view, she made her point. We did not need to have me dressed like that again. On some level, I was hoping that my girlie concessions to her would have given her enough, and she would not push things with a public outing.
Second, I was wondering what I would get for Christmas. I had my eye on a new Xbox game. I was hoping Mother would go for that.
Third, I really wanted to get Mother something special. I really had no idea what to get, and I decided to ask Auntie Anne for some help. She was flattered that I had asked her and was excited to take me shopping.
One afternoon, I went over to her house as I normally would to hang out with Isabel, and off we went to the mall.
We went to Bloomingdale's and kind of browsed around until we got to the huge cosmetics area. It was really overwhelming, with all of the beautiful cosmetics on display, all the people working there, putting makeup on customers, and trying to spray them with perfume. Lots of very attractive women working there, and a number of guys who were clearly very feminine.
All of them had arched, thinly shaped brows and earrings, and a few of them were even wearing makeup. My mind wandered, and I wondered what it would be like to work there, spending my days putting makeup on the girls and women, and occasional boys, who came by. What a fun job that would be.
Auntie Anne said, You know how much your mother loves makeup. Maybe we can get her something special here.
I thought that was a great idea. We wandered over to the Chanel counter. I recognized the woman who was working there, an older woman who was impeccably dressed and made up. Unfortunately, she recognized me too.
Oh, look who is here, that sweet boy who helps his mommie pick out her makeup. Jamie, right? I blushed furiously. I knew that Auntie Anne would be amused at this. I said yes, that was me, and said hello. Auntie Anne said, Hi, I am Anne, his mother's sister.
So, Emily comes here to shop with Jamie? That is so sweet. Normally, that is something a mother loves to do with her daughter, but Emily does not have a daughter. It is so nice that Jamie can, well, almost be like a daughter to her as well.
I knew she was having fun teasing me, and I was pretty embarrassed. But Auntie Anne was not done. She leaned towards the lady and said in a mock stage whisper, So, just between us, was my sister only shopping for herself? Or did she ever buy anything for Jamie?
The lady weighed this question and then said, well, I am not sure if she ever bought anything for him, but he certainly is a good little helper. His mother would always ask his opinion on things. They both seem to have a special fondness for lipstick.
Like Mother, Auntie Anne seemed to really enjoy spending time looking at all the cosmetics. The lady graciously showed us all the latest offerings. She also told us that there was a special holiday offering: if we spent more than one hundred dollars, which was not hard to do at the Chanel counter, we would get a special gift, a sample-sized lipstick, mascara, and fragrance. Auntie Anne wanted me to make the choices. Finally, I decided on an eyeshadow palette, a lipstick, and a compact. When choosing the lipstick, the lady used lots of samples and drew little lines on the top of my hand to show me what the colors would look like.
I loved that. For the compact, she went even further. She told me how it gave the skin a luminous glow and smoothed imperfections. She said, Here, honey, let me show you, and she took the pad and put a little powder on my face. I was embarrassed, but also intoxicated. Here I was at a makeup counter with the woman demonstrating on me. In all the times I had been with Mother, we had never done that.
Auntie Anne looked quite pleased. When the Chanel lady gift-wrapped my selections for Mother, she gave me a separate package with the free gift. She said, here honey, this is for you. And I threw in a few extras because you are such a special boy. I hope you get to use them.
I was relieved to have gotten Mother her gift and excited because I knew she would love it. And I knew she would especially love it because it had come from me.
Finally, it was the night before Christmas. Mother and I were going to spend a quiet evening at home. The next day, we would open our presents, and in the afternoon, we would head over to Auntie Anne's, who was hosting the big Christmas dinner this year. Mother still had not said anything about what I would be wearing.
That evening we relaxed with our usual hot cocoa. Since it was now winter, and since the first nightie she had gotten me was silky and not very warm, she had gotten me a flannel nightgown. Actually, she had gotten us matching nightgowns. It was cuddly and warm and pretty, and best of all, it was the same as Mother's. I loved to wear it.
It got too cold for the silk nightie, so Mother got both of us these flannel nightgowns.
Christmas was here. Mother asked me to wait until after breakfast to open our gifts. I felt a little funny because there were a lot of boxes under the tree, but only one was for Mother, and the rest were for me.
Even though she only had one, I asked her to open hers first. She did, and she was thrilled. She said, oh, sweetie, I know you know how much I love makeup, and especially Chanel. How did you do this? I told her that Auntie Anne took me, and that the nice lady we had met before was there and helped me.
But I told her that I picked all the makeup out myself. She was so proud of me. She said, I will try all this makeup on as we are done with our presents. Maybe you would like to help me. I blushed and did not say anything.
Next, it was my turn. Mother handed me the first gift. It was the Xbox game I had wanted. She then handed me another box. It was small.
She looked at me expectantly, almost like she was a little nervous. Inside was a pair of small gold hoop earrings. They were beautiful, but I looked at her questioningly. I did not have pierced ears. She looked at me and said, Do you like them?
I will admit I was confused. I did not know what to say. Finally, she said, You know, honey, lots of guys have their ears pierced. I just thought that you might like to have yours done too. And these are so pretty and tasteful. You could wear them with almost everything.
Of course, once your ears are pierced, well, I have dozens of pairs of earrings which you could borrow. I thought maybe later this morning we could go and get your ears pierced. What do you say? Would you like to do that?
I was really not sure. I did not want to seem ungrateful. I said, They are beautiful, Mommy. Thank you. Okay, we can do that. She looked almost relieved and gave me a big hug. Once again, pleasing Mother was worth anything.
Before Mother handed me the next present, she said, Jamie, I got you some things that I would like you to wear to Christmas dinner tonight. Uh oh. I was waiting for that. I decided not to object until I saw what she got for me.
The first thing she handed me was a shoebox. I opened it up. Inside were a pair of UGGs. Well, they were definitely girls' boots, but they were not horrible. I mean, I knew they were part of the teenage girl's uniform, along with leggings and tunic-style tops, but still, I rationalized that boys wore UGGs too. Yeah, right.
These were the UGGs Mother got me to wear to Christmas dinner.
Speaking of the uniform, the next box I opened confirmed my suspicions. I had seen the groups of girls in the mall. I was amazed at how they all wore the same thing: UGG boots, black leggings, and a longish top that could have passed for an extremely short skirt if they were not wearing the leggings. I mean, they all looked adorable. I loved the look. It was perfect for teenage girls, with their slim, long legs and hips that were still not that wide. But I did not picture myself wearing it. Okay, okay, maybe once or twice while daydreaming, but still, those were daydreams.
Anyway, the box contained a beautiful cashmere top. I loved cashmere; it was so soft and luxurious. And this must have cost a small fortune. It really was beautiful, and by itself, it was not too feminine. But with the UGG boots, I hugged Mother and told her how beautiful they were. And I just hoped that the next box did not contain a pair of leggings.
The cashmere top that Mother got me to go with the UGGs.
Of course, that was exactly what the next box contained: a pair of skin-tight, black leggings from Victoria's Secret. I wanted to be careful. Mother had spent a lot of money on me, and I did not want her to be upset or to think that I was ungrateful. And while it was true that any one piece of this outfit could have been worn by a boy or a girl, well, maybe not the leggings, the bottom line was that the outfit, UGG boots, black leggings, and a long sweater top, was the standard outfit of a teenage girl.
So, I said, Mother, I love everything. Thank you so much. I cannot wait to try everything. But, Mommie, can't I just wear this outfit at home? You know this is what all the girls wear, right? I would be really embarrassed to be wearing this in front of other people.
Mother seemed like she was expecting this reply. She said, Now, honey, it is not like I am making you wear one of the pretty dresses you have hanging in your closet, although I would like you to get some more use out of them, and tonight would be a perfect opportunity."
But I am not going to ask you to do that, because I know you would be embarrassed. But there is nothing wrong with this outfit. I think you will look absolutely adorable in it. In fact, I want you to try it on right now, before we head to the jewelry store. And yes, I expect you to wear it to dinner tonight. Now, you do not want to disappoint mommie, do you?
I was beaten. I said, no, mommie, of course I do not want to disappoint you. I started collecting my things to take them to my room to get dressed, when Mother stopped me. One more thing, sweetie. And she handed me a training bra. I know you know how to wear this. Now be a good girl and put this on under your new top. I did not even object to her calling me a girl. What was the point? I went upstairs to get changed.