Gratefully Feminized Sissy

I have always had effeminate mannerisms. Also, I have always had a feminine appearance. I grew up in the 1960's when it was acceptable, at least on some levels, for a boy to have long hair. So not wanting a son who was an outcast among his classmates, Mom let me grow my hair as long as I wanted. Also, Mom had blond hair as a child that turned brown when she hit puberty and was almost black by graduation. I had blond hair. On more than one occasion Mom lamented not having blond hair and hated that to achieve her early childhood shade she would have to spend a fortune at the salon. And on more than one occasion Mom had told me that she wished I was born a girl. So combine that with being slender, soft spoken and small for my age and an admittedly very pretty face, it was no wonder that Mom was eager to feminize me at every chance.

But I had mixed feelings. On one hand I had nightmares of waking up one day with facial hair, a buzz cut and a deep voice. On the other hand, I wanted to fit in with my peers and while long hair in the late sixties certainly did that, all the other aspects of being feminine did not. So I both embraced excitedly and hesitated fearfully every thing feminine that was imposed upon me.

I was four I think when Mom dressed me up as a fairy princess, butterfly wings, pink dress, pigtails, magic wand, tiara and all for Halloween. I took one look in the full length mirror in her bedroom after her masterpiece was complete and I was stunned. I was breath taking. My hair, which was about four inches longer than shoulder length and normally somewhat wavy was in big sausage curls held up as pigtails by big pink bows. I wore pink girl's shoes. Even my underwear was panties and Mom even spritzed me with a tiny amount of perfume. She handed me a pink pillow case for candy and put on a coat and took me around the neighborhood. I was so excited to show off my gorgeous self. I had no idea I could look so pretty and I had literally fallen into a sort of feminized trance blissfully unaware that I still had a dick and balls.

The first sucker punch to my gut was when a neighbor girl recognized me. She was in 2nd grade and had a baby brother a year younger than me and on occasion Mom had baby sat her and her Mom had baby sat me. She immediately broke out in laughter ridiculing me and I went flush with embarrassment and I wanted to go crawl under a rock. Then her mother came to the door, took one look at me, immediately recognized me as well, laughed as well but then went on for five minutes about how pretty I was and how I should have been born a girl and Mom agreed and she even suggested Mom send me to kindergarten like that. Mom said she would think about it and as the woman talked I was both scared and excited and insulted and complimented all at once and was very mixed up and confused.

We continued on until it got close to nine pm the town's trick-or-treat curfew and then returned home with my loot. I looked in my bag and that is when it hit me that this was the biggest bag of candy I had seen and Mom pointed out that a lot of people gave me extra just due to my lovely costume and how pretty I was. She sent me up to my room to change into my pajamas and when I got there I found a nightie on my bed instead and pink slippers that I had never seen. I looked in my dresser and could find no boy's pajamas so I stripped and got into the nightie and pink slippers and brushed my teeth and took my candy ration and glass of milk Mom gave me and climbed onto my bed waiting to be tucked in. Mom came in and said I looked pretty with the nightie and suggested I leave the pigtails in and she tucked me in and read me a story. It was a truncated version of Cinderella.

The next day Mom had me wear girl's panties and socks and t-shirt under my boys clothes. She brushed out my long hair the way she normally did playing down the length and feminine appearance by not having any accessories but she did spritz me with a tiny amount of perfume. She drove me to kindergarten dropping me off as usual and I went in and a couple of classmates remarked about my perfume smell but I explained it saying my Mom spilled it on herself accidentally prior to hugging me. They bought it for the time being. A few kids asked what I dressed up as and I didn't know enough to be too embarrassed to admit I was a fairy princess. A few kids laughed and one ridiculed but the subject changed quickly to something else, I forget what and the matter was dropped. One girl admitted to having dressed up as a soldier. Vietnam was in full swing by then and the war was not yet extremely unpopular as it later became.