Free to be a Sissyboy at Last
Dear Auntie Helga,

Per my mistress please find attached the opening stanza of the never ending saga of how I became involved in a life time of swishing skirts and tented panties, on the way to becoming a feminized sissy boy with an abiding desire for tight curly tresses and short prissy dresses. Albeit I have not always had a helpless penchant for sissy curls, forced enslavement in little girl's dresses and panty spanking discipline, nor the exciting fear and humiliation that accompanies them, but rather developed one over a hazy period of time.

I guess it first started in the sixth grade when I first realized the hidden green jealousy which led to my eventual desires for being sissified and humiliated. At that time I was a typical mouthy and arrogant boy, who loved all things manly, especially sports. One who additionally got great joy out of teasing the girls in my class. As such I got a special kick out of flicking up the back of the girls uniform skirts.

To digress my sister and I went to Saint John's Catholic school, which required white shirts and Ties, with pleated plaid skirts for the girls and uniform trousers for the boys. With the added distinction of the girl's blouses being soft and dainty, with short puffed sleeves, along with jaunty bow ties that bounced when they walked.

One day after several complaints I was brought to The principals office, a place I was quite familiar with. This time however in addition to the usual ear twisting and yard stick to the butt I was instructed to remove my uniform pants and tie. I got really scared as I thought they were going to expel me. Instead I was given a school skirt and clip on bow tie to put on.

When I laughingly objected, I was informed it was either go back to class in the skirt or go home in my skimpy underpants. Fearing my dad more then my friends laughter I went down the hall shaking with shame at the ridicule I knew was coming. However after the initial mocking insults, and being told to sit up next to the teachers desk where all could see me, I slowly realized that I was enjoying both the attention I was getting and the feeling of the way the pencil pleats of the skirt moved around my legs.

As I sat there it dawned on me that the only thing that was truly bothering me was that I didn't have a beanie to finish the look. It was at that moment that I realized I was jealous of the girl's hair. Not the run of the mill ones with their longer straight lady-like hair, but the ones with the short boyish pixie bobbed styles, permed into a prissy pot of bobbing curls, accented by the cute plaid beanie, which they saucily bobby pin on top.

Leaving for the next class I questioned the sister on my incomplete uniform. I guess she thought I was being a wise ass because the next thing I knew it was a bright yellow bow, not a nancy beanie, being bobby pinned to the top of my short school boy hair cut. This brought even more laughter then the skirt from the other boys, such that I found myself scurrying to sit with all the girls at my next class. I soon found myself however whispering and giggling with the best of them, having a grand old time.

The next day however, upon returning in my regulation pants and straight tie, I discovered when I tried to once again join their tittering, that I found myself getting the cold shoulder, which left me hurt and confused.

In anger I returned to my old rude actions which resulted in another trip to the office, where I was the recipient of a major bottom warming spanking and a further sentence in my borrowed pleated skirt, matching bow tie and frilly hair ribbon. Albeit this time it was to be for a full three days. In addition the good Sister added a pair of white satin like panties to my punishment, which caused the very first twinge ever in my adolescent gonads.

On top of that they decided it would be fitting if my punishment spanned my travels to and from school, to insure I got the full benefit of my angst. Little did they realize the extent of their decree, for my dad had a policy of whatever punishment I received at the hands of the good sisters must be justified, to wit he would double or repeat whatever it was. This in turn ended with my term in skirts not only being extended to six days, but would included all my off hours and weekend activities as well.

To wit be it the little league game the next night or church on Sunday, I found myself gracing the streets of Clark in all my feminine finery, to which my sister 'graciously' volunteered a pair of her patent leather red and white saddle-shoes.

Both the nuns and my dad thought that in so doing they would fix my arrogant wagon, but instead they had only provided me a chance to return to the company of my new found girlfriends.

In the back of my mind I even began scheming how I might be able to get my hair like theirs. To wit I subtly mentioned to my mom my desire to grow my hair longer like some of the other boys had recently started, a.k.a. the Beatles. In the meantime my bobbing satin hair bow became my crowning adornment.

Unfortunately after a couple of more rounds of returning to pants, which subsequently precipitated a replay of my old ways, the head sister decided the punishment was not working as planned, declaring it was time for a new punishment. Stupidly not wanting to lose my new friends nor the joy I got out of swishing skirts I panicked and cried out with the promise I'd be a good boy forever if she just kept me in a girl's uniform.

The second the words left my mouth I knew I had made a big mistake as I saw the look on her face. The next day, after a meeting with my parents, it was decided to switch me to a new class. Preceding my new punishment, of having to clean the convent after school each day for a month, I was ceremoniously taken to Frank's barber shop for the first of what would become a once a month ritual of getting my hair shorn into a crew cut.

On the outside I just as quickly returned to my old boisterous boyish ways, but on the inside I never lost my new found desire for swishing skirts and secreted soft panties, nor my equally burning longing for prissy girlish curls. In turn I eventually became a closet sissy, dressing in my mom's old nineteen forties style dresses stored in the attic, coupled with a curly Shirley Temple costume wig I found at a second hand store. It was not until years later however, when I finally got the chance to grow my hair long, that memories of my past petticoat disciplines came back to awaken my peculiar pansy libido. One that to this day sets my hips a wiggle and my knees a buckle, when ere the sweet siren swish of swaying skirts skim across the back of my thighs, sending my pantied loins into a vortex of turmoil. I leave you with a little ditty to remember me by. A song of freedom. Yours dearly, Sissy Gray.

FREE FROM TIES, FREE FROM PANTS FREE FROM ALL MY MACHO PAST! FREE IN PANTIES, FREE IN SKIRTS, FREE TO BE A SISSY BOY AT LAST!
Sissy Gray
Click to enlarge
Taking my skirt edges in hand, at Mistress's stern command, I salute you with a blown kiss from my pink hued lips. All the while stepping forward with a shy smile, whilst dropping a sweet curtsey at your commanding feet, I sing my theme song that lisps of my life in tight curly permed tresses and short frilly little girl dresses:

Boys in pretty party dresses with wide satin sashes, Puffy panties that dance when I'm getting my lashes. Shimmering pink petticoats that swish when I fling, These are a few of my frilly prissy effeminate things.

Lacey drops of sissy dew in my soft panty mittens, Tight curly permed tresses top off my little girl fixens. Short fluffy frocks which sway out when I swing, These are the reasons I'm a sweet nancified thing!

FINI


Thank you for your letter Sissy Gray. I'm sure you couldn't help but be influenced by the Sisters.

Auntie Helga

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